5-Bromo-7-methyl-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S160053681204682X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3464

doi:10.1107/S160053681204682X

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5-Bromo-7-methyl-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^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 7 November 2012; accepted 14 November 2012; online 28 November 2012)

In the title compound, C₁₇H₁₅BrO₂S, the 4-methylphenyl ring makes a dihedral angle of 14.46 (5)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by pairs of Br⋯O contacts [3.151 (2) Å] into centrosymmetric dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ); Seo et al. (2009 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₅BrO₂S
M_r = 363.26
Triclinic, $[P \overline 1]$
a = 7.6375 (2) Å
b = 9.5170 (2) Å
c = 11.2413 (2) Å
α = 75.513 (1)°
β = 84.848 (1)°
γ = 71.626 (1)°
V = 750.72 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.88 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.504, T_max = 0.568
14012 measured reflections
3716 independent reflections
3331 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.05
3716 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: 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 (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204682X/rz5021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204682X/rz5021Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204682X/rz5021Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-bromo-7-methyl-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010) and methyl (Seo et al., 2009) substituents in 2-position, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran ring is 14.46 (5)°. In the crystal structure, molecules are linked via pairs of Br···O halogen-bondings between the bromine and the oxygen of the S═O unit [Br1···O2ⁱ = 3.151 (2) Å, C4—Br1···O2ⁱ = 166.55 (6)°, symmetry code : (i) - x + 2, - y + 1, - z + 2] (Politzer et al., 2007) into centrosymmetric dimers.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010); Seo et al. (2009). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-7-methyl-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 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 column chromatography (hexane/ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 462–463 K; Rf = 0.53 (hexane/ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

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 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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.

5-Bromo-7-methyl-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₂S	Z = 2
M_r = 363.26	F(000) = 368
Triclinic, P1	D_x = 1.607 Mg m⁻³
Hall symbol: -P 1	Melting point = 462–463 K
a = 7.6375 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5170 (2) Å	Cell parameters from 6280 reflections
c = 11.2413 (2) Å	θ = 2.6–28.3°
α = 75.513 (1)°	µ = 2.88 mm⁻¹
β = 84.848 (1)°	T = 173 K
γ = 71.626 (1)°	Block, colourless
V = 750.72 (3) Å³	0.28 × 0.24 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3716 independent reflections
Radiation source: rotating anode	3331 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.040
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.9°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.504, T_max = 0.568	l = −14→14
14012 measured reflections

Refinement top

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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.039P)² + 0.174P] where P = (F_o² + 2F_c²)/3
3716 reflections	(Δ/σ)_max = 0.002
193 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₂S	γ = 71.626 (1)°
M_r = 363.26	V = 750.72 (3) Å³
Triclinic, P1	Z = 2
a = 7.6375 (2) Å	Mo Kα radiation
b = 9.5170 (2) Å	µ = 2.88 mm⁻¹
c = 11.2413 (2) Å	T = 173 K
α = 75.513 (1)°	0.28 × 0.24 × 0.22 mm
β = 84.848 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3716 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3331 reflections with I > 2σ(I)
T_min = 0.504, T_max = 0.568	R_int = 0.040
14012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	Δρ_max = 0.48 e Å⁻³
3716 reflections	Δρ_min = −0.56 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Br1	1.01640 (2)	0.25733 (2)	1.044940 (18)	0.03262 (8)
S1	0.65991 (7)	0.79517 (5)	0.61463 (5)	0.03608 (13)
O1	0.80729 (16)	0.39887 (14)	0.52060 (12)	0.0266 (3)
O2	0.7824 (3)	0.80345 (17)	0.70610 (17)	0.0516 (4)
C1	0.7300 (2)	0.60520 (19)	0.60028 (18)	0.0262 (4)
C2	0.8166 (2)	0.47429 (19)	0.69618 (17)	0.0247 (3)
C3	0.8598 (2)	0.44924 (19)	0.81916 (18)	0.0270 (4)
H3	0.8304	0.5300	0.8601	0.032*
C6	0.9504 (2)	0.2018 (2)	0.69871 (19)	0.0278 (4)
C10	0.6566 (2)	0.6248 (2)	0.37333 (17)	0.0258 (3)
C4	0.9481 (2)	0.3001 (2)	0.87834 (18)	0.0265 (4)
C14	0.6396 (3)	0.6087 (2)	0.16459 (19)	0.0339 (4)
H14	0.6760	0.5516	0.1034	0.041*
C5	0.9929 (2)	0.1788 (2)	0.82077 (18)	0.0285 (4)
H5	1.0535	0.0787	0.8661	0.034*
C8	0.7269 (2)	0.55446 (19)	0.49709 (17)	0.0251 (3)
C7	0.8620 (2)	0.35210 (19)	0.64087 (17)	0.0244 (3)
C12	0.4659 (3)	0.8359 (2)	0.22513 (19)	0.0322 (4)
H12	0.3837	0.9368	0.2061	0.039*
C13	0.5173 (2)	0.7551 (2)	0.13389 (19)	0.0315 (4)
C11	0.5323 (3)	0.7721 (2)	0.34314 (19)	0.0310 (4)
H11	0.4931	0.8286	0.4045	0.037*
C15	0.7097 (3)	0.5440 (2)	0.28117 (19)	0.0306 (4)
H15	0.7943	0.4441	0.2990	0.037*
C16	0.4439 (3)	0.8233 (3)	0.0066 (2)	0.0401 (5)
H16A	0.3579	0.9255	0.0027	0.060*
H16B	0.3794	0.7591	−0.0149	0.060*
H16C	0.5464	0.8300	−0.0514	0.060*
C9	0.9909 (3)	0.0770 (2)	0.6320 (2)	0.0389 (5)
H9A	1.0309	−0.0220	0.6908	0.058*
H9B	1.0890	0.0862	0.5708	0.058*
H9C	0.8793	0.0850	0.5907	0.058*
C17	0.4442 (3)	0.7945 (3)	0.6906 (2)	0.0482 (6)
H17A	0.4645	0.7094	0.7633	0.072*
H17B	0.3613	0.7832	0.6344	0.072*
H17C	0.3884	0.8906	0.7158	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04139 (12)	0.03114 (11)	0.02435 (12)	−0.01163 (8)	−0.01237 (8)	0.00023 (8)
S1	0.0551 (3)	0.0203 (2)	0.0333 (3)	−0.01144 (19)	−0.0163 (2)	−0.00163 (19)
O1	0.0316 (6)	0.0258 (6)	0.0205 (7)	−0.0063 (5)	−0.0039 (5)	−0.0037 (5)
O2	0.0753 (11)	0.0340 (8)	0.0538 (11)	−0.0211 (7)	−0.0298 (9)	−0.0090 (7)
C1	0.0327 (8)	0.0213 (7)	0.0247 (10)	−0.0096 (6)	−0.0067 (7)	−0.0014 (7)
C2	0.0276 (8)	0.0232 (8)	0.0234 (10)	−0.0095 (6)	−0.0055 (7)	−0.0016 (7)
C3	0.0328 (8)	0.0251 (8)	0.0247 (10)	−0.0104 (7)	−0.0067 (7)	−0.0042 (7)
C6	0.0272 (8)	0.0256 (8)	0.0288 (10)	−0.0046 (6)	−0.0037 (7)	−0.0062 (7)
C10	0.0283 (8)	0.0292 (8)	0.0202 (9)	−0.0124 (7)	−0.0042 (7)	−0.0004 (7)
C4	0.0289 (8)	0.0295 (8)	0.0211 (9)	−0.0106 (7)	−0.0076 (7)	−0.0013 (7)
C14	0.0405 (10)	0.0418 (10)	0.0217 (10)	−0.0152 (8)	−0.0013 (8)	−0.0078 (8)
C5	0.0294 (8)	0.0248 (8)	0.0283 (10)	−0.0066 (6)	−0.0069 (7)	−0.0008 (7)
C8	0.0261 (8)	0.0243 (8)	0.0243 (10)	−0.0089 (6)	−0.0033 (7)	−0.0018 (7)
C7	0.0260 (8)	0.0261 (8)	0.0209 (9)	−0.0081 (6)	−0.0034 (6)	−0.0038 (7)
C12	0.0337 (9)	0.0334 (9)	0.0261 (11)	−0.0093 (7)	−0.0065 (8)	0.0000 (8)
C13	0.0312 (9)	0.0429 (10)	0.0215 (10)	−0.0172 (8)	−0.0055 (7)	0.0001 (8)
C11	0.0362 (9)	0.0313 (9)	0.0238 (10)	−0.0088 (7)	−0.0048 (7)	−0.0037 (8)
C15	0.0331 (9)	0.0319 (9)	0.0256 (10)	−0.0098 (7)	−0.0019 (7)	−0.0042 (8)
C16	0.0398 (10)	0.0549 (13)	0.0250 (11)	−0.0181 (9)	−0.0075 (8)	−0.0009 (10)
C9	0.0461 (11)	0.0272 (9)	0.0374 (13)	0.0001 (8)	−0.0038 (9)	−0.0103 (9)
C17	0.0543 (13)	0.0416 (12)	0.0459 (15)	−0.0019 (10)	−0.0051 (11)	−0.0202 (11)

Geometric parameters (Å, º) top

Br1—C4	1.8987 (19)	C14—C15	1.377 (3)
Br1—O2ⁱ	3.1514 (17)	C14—C13	1.389 (3)
S1—O2	1.4825 (16)	C14—H14	0.9500
S1—C1	1.7611 (17)	C5—H5	0.9500
S1—C17	1.787 (3)	C12—C11	1.382 (3)
O1—C7	1.372 (2)	C12—C13	1.389 (3)
O1—C8	1.378 (2)	C12—H12	0.9500
C1—C8	1.368 (3)	C13—C16	1.494 (3)
C1—C2	1.445 (2)	C11—H11	0.9500
C2—C7	1.388 (2)	C15—H15	0.9500
C2—C3	1.395 (3)	C16—H16A	0.9800
C3—C4	1.385 (2)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C6—C5	1.386 (3)	C9—H9A	0.9800
C6—C7	1.389 (2)	C9—H9B	0.9800
C6—C9	1.497 (3)	C9—H9C	0.9800
C10—C15	1.398 (3)	C17—H17A	0.9800
C10—C11	1.401 (3)	C17—H17B	0.9800
C10—C8	1.454 (3)	C17—H17C	0.9800
C4—C5	1.398 (3)

C4—Br1—O2ⁱ	166.55 (6)	O1—C7—C6	123.97 (16)
O2—S1—C1	106.92 (9)	C2—C7—C6	124.96 (18)
O2—S1—C17	106.93 (12)	C11—C12—C13	121.09 (18)
C1—S1—C17	97.14 (10)	C11—C12—H12	119.5
C7—O1—C8	106.78 (13)	C13—C12—H12	119.5
C8—C1—C2	107.54 (15)	C12—C13—C14	117.90 (18)
C8—C1—S1	127.55 (14)	C12—C13—C16	121.17 (18)
C2—C1—S1	124.74 (14)	C14—C13—C16	120.94 (19)
C7—C2—C3	119.56 (16)	C12—C11—C10	120.76 (19)
C7—C2—C1	104.61 (16)	C12—C11—H11	119.6
C3—C2—C1	135.82 (17)	C10—C11—H11	119.6
C4—C3—C2	116.29 (16)	C14—C15—C10	120.27 (18)
C4—C3—H3	121.9	C14—C15—H15	119.9
C2—C3—H3	121.9	C10—C15—H15	119.9
C5—C6—C7	114.80 (16)	C13—C16—H16A	109.5
C5—C6—C9	124.04 (17)	C13—C16—H16B	109.5
C7—C6—C9	121.14 (18)	H16A—C16—H16B	109.5
C15—C10—C11	118.12 (18)	C13—C16—H16C	109.5
C15—C10—C8	120.06 (16)	H16A—C16—H16C	109.5
C11—C10—C8	121.81 (17)	H16B—C16—H16C	109.5
C3—C4—C5	123.18 (18)	C6—C9—H9A	109.5
C3—C4—Br1	118.81 (14)	C6—C9—H9B	109.5
C5—C4—Br1	118.00 (13)	H9A—C9—H9B	109.5
C15—C14—C13	121.86 (19)	C6—C9—H9C	109.5
C15—C14—H14	119.1	H9A—C9—H9C	109.5
C13—C14—H14	119.1	H9B—C9—H9C	109.5
C6—C5—C4	121.20 (16)	S1—C17—H17A	109.5
C6—C5—H5	119.4	S1—C17—H17B	109.5
C4—C5—H5	119.4	H17A—C17—H17B	109.5
C1—C8—O1	109.99 (15)	S1—C17—H17C	109.5
C1—C8—C10	135.25 (16)	H17A—C17—H17C	109.5
O1—C8—C10	114.74 (15)	H17B—C17—H17C	109.5
O1—C7—C2	111.07 (15)

O2—S1—C1—C8	−146.49 (17)	C15—C10—C8—C1	166.89 (19)
C17—S1—C1—C8	103.34 (18)	C11—C10—C8—C1	−14.6 (3)
O2—S1—C1—C2	28.10 (19)	C15—C10—C8—O1	−14.8 (2)
C17—S1—C1—C2	−82.07 (17)	C11—C10—C8—O1	163.75 (15)
C8—C1—C2—C7	0.78 (19)	C8—O1—C7—C2	0.72 (18)
S1—C1—C2—C7	−174.73 (13)	C8—O1—C7—C6	−179.55 (16)
C8—C1—C2—C3	−179.73 (19)	C3—C2—C7—O1	179.48 (14)
S1—C1—C2—C3	4.8 (3)	C1—C2—C7—O1	−0.92 (19)
C7—C2—C3—C4	0.3 (2)	C3—C2—C7—C6	−0.2 (3)
C1—C2—C3—C4	−179.18 (19)	C1—C2—C7—C6	179.35 (16)
C2—C3—C4—C5	−0.2 (3)	C5—C6—C7—O1	−179.58 (15)
C2—C3—C4—Br1	178.66 (12)	C9—C6—C7—O1	−0.8 (3)
O2ⁱ—Br1—C4—C3	−92.2 (3)	C5—C6—C7—C2	0.1 (3)
O2ⁱ—Br1—C4—C5	86.6 (3)	C9—C6—C7—C2	178.91 (18)
C7—C6—C5—C4	0.0 (3)	C11—C12—C13—C14	−0.9 (3)
C9—C6—C5—C4	−178.76 (18)	C11—C12—C13—C16	179.26 (18)
C3—C4—C5—C6	0.0 (3)	C15—C14—C13—C12	−0.2 (3)
Br1—C4—C5—C6	−178.79 (13)	C15—C14—C13—C16	179.66 (18)
C2—C1—C8—O1	−0.37 (19)	C13—C12—C11—C10	1.4 (3)
S1—C1—C8—O1	174.97 (13)	C15—C10—C11—C12	−0.8 (3)
C2—C1—C8—C10	178.02 (18)	C8—C10—C11—C12	−179.30 (16)
S1—C1—C8—C10	−6.6 (3)	C13—C14—C15—C10	0.8 (3)
C7—O1—C8—C1	−0.20 (18)	C11—C10—C15—C14	−0.3 (3)
C7—O1—C8—C10	−178.95 (14)	C8—C10—C15—C14	178.27 (16)

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₂S
M_r	363.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.6375 (2), 9.5170 (2), 11.2413 (2)
α, β, γ (°)	75.513 (1), 84.848 (1), 71.626 (1)
V (Å³)	750.72 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.88
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.504, 0.568
No. of measured, independent and observed [I > 2σ(I)] reflections	14012, 3716, 3331
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.05
No. of reflections	3716
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.56

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

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.

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