organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3-(4-Bromo­phenyl­sulfin­yl)-2,5,6-tri­methyl-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

(Received 19 June 2013; accepted 27 June 2013; online 6 July 2013)

In the title compound, C17H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.003 (2) Å] of the benzo­furan ring system and the mean plane [r.m.s. deviation = 0.006 (2) Å] of the 4-bromo­phenyl ring is 83.09 (7)°. In the crystal, weak C—H⋯π inter­actions are observed.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o543.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2551.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o584.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15BrO2S

  • Mr = 363.26

  • Monoclinic, P 21 /c

  • a = 20.0084 (8) Å

  • b = 7.1890 (3) Å

  • c = 10.7804 (4) Å

  • β = 101.478 (2)°

  • V = 1519.65 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.84 mm−1

  • T = 173 K

  • 0.37 × 0.26 × 0.05 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.425, Tmax = 0.746

  • 26485 measured reflections

  • 3791 independent reflections

  • 2928 reflections with I > 2σ(I)

  • Rint = 0.071

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.05

  • 3791 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.75 e Å−3

  • Δρmin = −0.86 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9CCg1i 0.98 2.89 3.537 (4) 124
C11—H11CCg2ii 0.98 2.78 3.714 (4) 159
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our continuing study of 2,5-dimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi et al., 2010a), 4-chlorophenylsulfinyl (Choi et al., 2010b) and 4-bromophenylsulfinyl (Choi et al., 2012) substituents in 3-position, we report here the crystal structure of the title compound.

In the title molecule the benzofuran unit is essentially planar, with a mean deviation of 0.003 (2) Å from the least-squares plane defined by the nine constituent atoms (Fig. 1). The 4-bromophenyl ring is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle between the mean plane of the benzofuran ring system and the 4-bromophenyl ring is 83.09 (7)°. In the crystal structure the molecules are connected by weak C—H···π interactions (Table 1 and Fig. 2), Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively)

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran (278 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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 column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 446–447 K; Rf = 0.41 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the solvent from a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically (methyl H atoms allowed to rotate but not to tip) and refined with Uiso(H) = 1.2Ueq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.95 Å for aryl and 0.98Å for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Fig. 2. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms that does not participate in this interaction are omitted for clarity.Symmetry codes: (i) x, - y + 1/2, z - 1/2; (ii) x, - y + 3/2, z + 1/2; (iii) x, - y +1/2, z + 1/2; (iv) x, - y + 3/2, z - 1/2.]
3-(4-Bromophenylsulfinyl)-2,5,6-trimethyl-1-benzofuran top
Crystal data top
C17H15BrO2SF(000) = 736
Mr = 363.26Dx = 1.588 Mg m3
Monoclinic, P21/cMelting point = 446–447 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 20.0084 (8) ÅCell parameters from 6275 reflections
b = 7.1890 (3) Åθ = 3.1–27.2°
c = 10.7804 (4) ŵ = 2.84 mm1
β = 101.478 (2)°T = 173 K
V = 1519.65 (10) Å3Block, colourless
Z = 40.37 × 0.26 × 0.05 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3791 independent reflections
Radiation source: rotating anode2928 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.071
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.1°
ϕ and ω scansh = 2626
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 79
Tmin = 0.425, Tmax = 0.746l = 1414
26485 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.114H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.8553P]
where P = (Fo2 + 2Fc2)/3
3791 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.86 e Å3
Crystal data top
C17H15BrO2SV = 1519.65 (10) Å3
Mr = 363.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.0084 (8) ŵ = 2.84 mm1
b = 7.1890 (3) ÅT = 173 K
c = 10.7804 (4) Å0.37 × 0.26 × 0.05 mm
β = 101.478 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3791 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2928 reflections with I > 2σ(I)
Tmin = 0.425, Tmax = 0.746Rint = 0.071
26485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.05Δρmax = 0.75 e Å3
3791 reflectionsΔρmin = 0.86 e Å3
193 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.471187 (16)0.90385 (6)0.33352 (3)0.06164 (16)
S10.30484 (3)0.38470 (9)0.64879 (6)0.02963 (16)
O10.11729 (8)0.5558 (2)0.62907 (13)0.0245 (4)
O20.30702 (10)0.1917 (3)0.5990 (2)0.0456 (5)
C10.22159 (11)0.4684 (3)0.60389 (19)0.0230 (5)
C20.17882 (11)0.4857 (3)0.47877 (19)0.0218 (4)
C30.18654 (12)0.4633 (3)0.35339 (19)0.0240 (5)
H30.22920.42670.33540.029*
C40.13130 (12)0.4951 (3)0.25574 (19)0.0242 (5)
C50.06756 (12)0.5501 (3)0.28199 (19)0.0230 (4)
C60.06000 (11)0.5739 (3)0.40622 (19)0.0230 (5)
H60.01780.61240.42530.028*
C70.11582 (11)0.5398 (3)0.50083 (18)0.0220 (4)
C80.18216 (12)0.5111 (3)0.68885 (19)0.0245 (5)
C90.13935 (14)0.4700 (4)0.1205 (2)0.0327 (6)
H9A0.18750.44770.11870.049*
H9B0.12380.58260.07200.049*
H9C0.11200.36350.08310.049*
C100.00712 (13)0.5824 (4)0.1766 (2)0.0302 (5)
H10A0.03250.61670.21230.045*
H10B0.00300.46830.12650.045*
H10C0.01740.68310.12210.045*
C110.19543 (14)0.5183 (4)0.82940 (19)0.0313 (5)
H11A0.24250.47950.86330.047*
H11B0.16390.43440.86070.047*
H11C0.18870.64560.85690.047*
C120.34419 (11)0.5327 (4)0.5498 (2)0.0270 (5)
C130.38253 (14)0.4501 (4)0.4718 (3)0.0407 (7)
H130.38380.31860.46440.049*
C140.41911 (14)0.5619 (5)0.4046 (3)0.0469 (8)
H140.44510.50780.34920.056*
C150.41750 (12)0.7519 (5)0.4186 (2)0.0379 (7)
C160.37837 (13)0.8355 (4)0.4953 (2)0.0354 (6)
H160.37680.96710.50220.042*
C170.34162 (12)0.7238 (4)0.5615 (2)0.0302 (5)
H170.31460.77820.61510.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04327 (19)0.1047 (4)0.03699 (18)0.03020 (17)0.00810 (13)0.01789 (15)
S10.0254 (3)0.0305 (4)0.0322 (3)0.0010 (2)0.0038 (2)0.0074 (2)
O10.0278 (8)0.0287 (10)0.0182 (7)0.0021 (7)0.0074 (6)0.0007 (6)
O20.0385 (10)0.0257 (12)0.0747 (14)0.0058 (9)0.0161 (9)0.0068 (9)
C10.0266 (11)0.0214 (13)0.0213 (10)0.0025 (9)0.0052 (8)0.0014 (8)
C20.0257 (10)0.0181 (12)0.0222 (10)0.0018 (9)0.0059 (8)0.0016 (8)
C30.0291 (11)0.0215 (13)0.0231 (10)0.0034 (10)0.0094 (8)0.0024 (8)
C40.0351 (12)0.0189 (12)0.0199 (9)0.0002 (10)0.0088 (8)0.0002 (8)
C50.0286 (11)0.0179 (12)0.0220 (10)0.0026 (9)0.0039 (8)0.0016 (7)
C60.0242 (10)0.0223 (13)0.0234 (10)0.0005 (9)0.0067 (8)0.0009 (8)
C70.0294 (11)0.0198 (13)0.0188 (9)0.0017 (9)0.0094 (8)0.0007 (7)
C80.0299 (11)0.0223 (13)0.0208 (10)0.0014 (10)0.0042 (8)0.0004 (8)
C90.0476 (14)0.0308 (15)0.0208 (10)0.0117 (12)0.0095 (10)0.0008 (9)
C100.0330 (12)0.0322 (15)0.0234 (11)0.0006 (11)0.0006 (9)0.0014 (9)
C110.0427 (14)0.0321 (15)0.0186 (10)0.0015 (12)0.0052 (9)0.0006 (8)
C120.0225 (10)0.0335 (15)0.0242 (10)0.0014 (10)0.0030 (8)0.0001 (9)
C130.0395 (15)0.0385 (18)0.0480 (15)0.0000 (13)0.0185 (12)0.0072 (12)
C140.0393 (16)0.063 (2)0.0438 (16)0.0047 (14)0.0222 (13)0.0116 (13)
C150.0257 (12)0.059 (2)0.0288 (12)0.0102 (12)0.0057 (9)0.0066 (11)
C160.0296 (12)0.0378 (16)0.0376 (13)0.0048 (12)0.0040 (10)0.0070 (11)
C170.0272 (11)0.0325 (15)0.0322 (11)0.0010 (10)0.0086 (9)0.0005 (9)
Geometric parameters (Å, º) top
Br1—C151.892 (3)C9—H9A0.9800
S1—O21.492 (2)C9—H9B0.9800
S1—C11.746 (2)C9—H9C0.9800
S1—C121.796 (2)C10—H10A0.9800
O1—C81.368 (3)C10—H10B0.9800
O1—C71.382 (2)C10—H10C0.9800
C1—C81.358 (3)C11—H11A0.9800
C1—C21.452 (3)C11—H11B0.9800
C2—C71.384 (3)C11—H11C0.9800
C2—C31.400 (3)C12—C131.380 (3)
C3—C41.385 (3)C12—C171.382 (4)
C3—H30.9500C13—C141.385 (4)
C4—C51.417 (3)C13—H130.9500
C4—C91.509 (3)C14—C151.375 (5)
C5—C61.388 (3)C14—H140.9500
C5—C101.504 (3)C15—C161.384 (4)
C6—C71.376 (3)C16—C171.380 (3)
C6—H60.9500C16—H160.9500
C8—C111.486 (3)C17—H170.9500
O2—S1—C1108.38 (11)H9A—C9—H9C109.5
O2—S1—C12106.81 (11)H9B—C9—H9C109.5
C1—S1—C1297.93 (11)C5—C10—H10A109.5
C8—O1—C7106.33 (16)C5—C10—H10B109.5
C8—C1—C2107.05 (19)H10A—C10—H10B109.5
C8—C1—S1122.76 (16)C5—C10—H10C109.5
C2—C1—S1129.82 (16)H10A—C10—H10C109.5
C7—C2—C3118.5 (2)H10B—C10—H10C109.5
C7—C2—C1104.66 (18)C8—C11—H11A109.5
C3—C2—C1136.8 (2)C8—C11—H11B109.5
C4—C3—C2119.4 (2)H11A—C11—H11B109.5
C4—C3—H3120.3C8—C11—H11C109.5
C2—C3—H3120.3H11A—C11—H11C109.5
C3—C4—C5120.54 (18)H11B—C11—H11C109.5
C3—C4—C9119.5 (2)C13—C12—C17121.3 (2)
C5—C4—C9120.0 (2)C13—C12—S1118.0 (2)
C6—C5—C4120.2 (2)C17—C12—S1120.38 (17)
C6—C5—C10119.0 (2)C12—C13—C14119.0 (3)
C4—C5—C10120.84 (19)C12—C13—H13120.5
C7—C6—C5117.7 (2)C14—C13—H13120.5
C7—C6—H6121.1C15—C14—C13119.5 (2)
C5—C6—H6121.1C15—C14—H14120.3
C6—C7—O1125.39 (19)C13—C14—H14120.3
C6—C7—C2123.72 (19)C14—C15—C16121.7 (2)
O1—C7—C2110.88 (19)C14—C15—Br1119.5 (2)
C1—C8—O1111.08 (18)C16—C15—Br1118.8 (2)
C1—C8—C11133.3 (2)C17—C16—C15118.7 (3)
O1—C8—C11115.63 (19)C17—C16—H16120.7
C4—C9—H9A109.5C15—C16—H16120.7
C4—C9—H9B109.5C16—C17—C12119.8 (2)
H9A—C9—H9B109.5C16—C17—H17120.1
C4—C9—H9C109.5C12—C17—H17120.1
O2—S1—C1—C8115.6 (2)C1—C2—C7—C6179.3 (2)
C12—S1—C1—C8133.6 (2)C3—C2—C7—O1179.8 (2)
O2—S1—C1—C256.5 (3)C1—C2—C7—O10.2 (3)
C12—S1—C1—C254.3 (2)C2—C1—C8—O10.3 (3)
C8—C1—C2—C70.3 (3)S1—C1—C8—O1174.01 (17)
S1—C1—C2—C7173.37 (19)C2—C1—C8—C11179.6 (3)
C8—C1—C2—C3179.8 (3)S1—C1—C8—C116.0 (4)
S1—C1—C2—C37.1 (4)C7—O1—C8—C10.2 (3)
C7—C2—C3—C40.2 (3)C7—O1—C8—C11179.7 (2)
C1—C2—C3—C4179.7 (3)O2—S1—C12—C1315.3 (2)
C2—C3—C4—C50.1 (4)C1—S1—C12—C13127.3 (2)
C2—C3—C4—C9179.7 (2)O2—S1—C12—C17171.18 (18)
C3—C4—C5—C60.4 (4)C1—S1—C12—C1759.2 (2)
C9—C4—C5—C6179.8 (2)C17—C12—C13—C140.1 (4)
C3—C4—C5—C10179.2 (2)S1—C12—C13—C14173.3 (2)
C9—C4—C5—C100.6 (3)C12—C13—C14—C151.2 (4)
C4—C5—C6—C70.9 (3)C13—C14—C15—C162.2 (4)
C10—C5—C6—C7178.7 (2)C13—C14—C15—Br1176.7 (2)
C5—C6—C7—O1179.7 (2)C14—C15—C16—C171.7 (4)
C5—C6—C7—C20.8 (4)Br1—C15—C16—C17177.17 (18)
C8—O1—C7—C6179.5 (2)C15—C16—C17—C120.4 (4)
C8—O1—C7—C20.0 (3)C13—C12—C17—C160.5 (4)
C3—C2—C7—C60.3 (4)S1—C12—C17—C16172.77 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cg1i0.982.893.537 (4)124
C11—H11C···Cg2ii0.982.783.714 (4)159
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H15BrO2S
Mr363.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)20.0084 (8), 7.1890 (3), 10.7804 (4)
β (°) 101.478 (2)
V3)1519.65 (10)
Z4
Radiation typeMo Kα
µ (mm1)2.84
Crystal size (mm)0.37 × 0.26 × 0.05
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.425, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
26485, 3791, 2928
Rint0.071
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.114, 1.05
No. of reflections3791
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.75, 0.86

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cg1i0.982.893.537 (4)124.4
C11—H11C···Cg2ii0.982.783.714 (4)159.0
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+3/2, z+1/2.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

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