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)-5-chloro-2,7-di­methyl-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 3 April 2013; accepted 11 April 2013; online 17 April 2013)

In the title compound, C16H12BrClO2S, the 4-bromo­phenyl ring makes a dihedral angle of 88.84 (5)° with the mean plane [r.m.s. deviation = 0.009 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—S⋯π [3.386 (2) Å] inter­actions, forming a chain perpendicular to the bc plane.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012a[Choi, H. D., Seo, P. J. & Lee, U. (2012a). Acta Cryst. E68, o2027.],b[Choi, H. D., Seo, P. J. & Lee, U. (2012b). Acta Cryst. E68, o2080.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12BrClO2S

  • Mr = 383.68

  • Triclinic, [P \overline 1]

  • a = 6.1266 (3) Å

  • b = 10.0247 (5) Å

  • c = 12.6630 (7) Å

  • α = 84.749 (3)°

  • β = 79.235 (2)°

  • γ = 86.443 (3)°

  • V = 760.03 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.02 mm−1

  • T = 173 K

  • 0.33 × 0.23 × 0.16 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 = 0.506, Tmax = 0.746

  • 13853 measured reflections

  • 3794 independent reflections

  • 3209 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.082

  • S = 1.05

  • 3794 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O2i 0.95 2.50 3.249 (2) 136
Symmetry code: (i) -x, -y+1, -z+1.

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 5-chloro-2-methyl-1-benzofuran derivatives containing 4-bromophenylsulfonyl (Choi et al., 2012a) and 4-bromophenylsulfinyl (Choi et al., 2012b) substituents in 3-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 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran ring is 88.84 (5)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1), and by intermolecular C—S···π interactions between the sulfur atom and the 4-bromophenyl ring of an adjacent molecule, with a S1···Cgii being 3.386 (2) Å (Cg is the centroid of the C11/C16 ring).

Related literature top

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

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2,7-dimethyl-1-benzofuran (331 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5 h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 442–443 K; Rf = 0.78 (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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 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 rotationally.

Structure description top

As a part of our continuing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 4-bromophenylsulfonyl (Choi et al., 2012a) and 4-bromophenylsulfinyl (Choi et al., 2012b) substituents in 3-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 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran ring is 88.84 (5)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1), and by intermolecular C—S···π interactions between the sulfur atom and the 4-bromophenyl ring of an adjacent molecule, with a S1···Cgii being 3.386 (2) Å (Cg is the centroid of the C11/C16 ring).

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

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. A view of the C—H···O and C—S···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x, - y + 1, - z + 1; (ii) - x + 1, - y + 1 , - z + 1.]
3-(4-Bromophenylsulfinyl)-5-chloro-2,7-dimethyl-1-benzofuran top
Crystal data top
C16H12BrClO2SZ = 2
Mr = 383.68F(000) = 384
Triclinic, P1Dx = 1.677 Mg m3
Hall symbol: -P 1Melting point = 442–443 K
a = 6.1266 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0247 (5) ÅCell parameters from 6958 reflections
c = 12.6630 (7) Åθ = 2.5–28.5°
α = 84.749 (3)°µ = 3.02 mm1
β = 79.235 (2)°T = 173 K
γ = 86.443 (3)°Block, colourless
V = 760.03 (7) Å30.33 × 0.23 × 0.16 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3794 independent reflections
Radiation source: rotating anode3209 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.041
Detector resolution: 10.0 pixels mm-1θmax = 28.5°, θmin = 1.6°
φ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.506, Tmax = 0.746l = 1616
13853 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)] = 0.031Hydrogen site location: difference Fourier map
wR(F2) = 0.082H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2147P]
where P = (Fo2 + 2Fc2)/3
3794 reflections(Δ/σ)max = 0.002
192 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.72 e Å3
Crystal data top
C16H12BrClO2Sγ = 86.443 (3)°
Mr = 383.68V = 760.03 (7) Å3
Triclinic, P1Z = 2
a = 6.1266 (3) ÅMo Kα radiation
b = 10.0247 (5) ŵ = 3.02 mm1
c = 12.6630 (7) ÅT = 173 K
α = 84.749 (3)°0.33 × 0.23 × 0.16 mm
β = 79.235 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3794 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3209 reflections with I > 2σ(I)
Tmin = 0.506, Tmax = 0.746Rint = 0.041
13853 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.05Δρmax = 0.38 e Å3
3794 reflectionsΔρmin = 0.72 e Å3
192 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
Br10.60695 (4)0.00462 (2)0.662469 (16)0.03820 (9)
Cl10.07539 (9)0.08106 (6)0.16204 (5)0.03950 (14)
S10.38584 (8)0.50904 (4)0.34160 (3)0.02363 (11)
O10.7066 (2)0.40065 (13)0.06063 (10)0.0251 (3)
O20.1390 (2)0.52341 (15)0.35333 (11)0.0326 (3)
C10.4874 (3)0.43659 (18)0.21924 (14)0.0226 (4)
C20.3886 (3)0.33547 (18)0.17248 (14)0.0218 (4)
C30.1985 (3)0.26119 (19)0.20141 (15)0.0253 (4)
H30.09810.27090.26740.030*
C40.1635 (3)0.17304 (19)0.12968 (16)0.0266 (4)
C50.3103 (3)0.15431 (19)0.03288 (15)0.0288 (4)
H50.27940.09080.01300.035*
C60.5011 (3)0.22733 (19)0.00283 (14)0.0266 (4)
C70.5301 (3)0.31709 (18)0.07481 (14)0.0228 (4)
C80.6746 (3)0.47297 (19)0.14948 (14)0.0235 (4)
C90.6643 (4)0.2110 (2)0.10013 (16)0.0366 (5)
H9A0.67920.29760.14290.055*
H9B0.61080.14580.14140.055*
H9C0.80920.17910.08320.055*
C100.8461 (3)0.5696 (2)0.15219 (16)0.0301 (4)
H10A0.79060.63080.20830.045*
H10B0.88000.62110.08200.045*
H10C0.98130.52080.16810.045*
C110.4447 (3)0.36641 (18)0.43057 (14)0.0219 (4)
C120.2744 (3)0.3133 (2)0.50722 (15)0.0258 (4)
H120.12670.35040.51210.031*
C130.3225 (3)0.2049 (2)0.57709 (15)0.0290 (4)
H130.20750.16620.62970.035*
C140.5385 (4)0.15413 (19)0.56925 (15)0.0267 (4)
C150.7110 (3)0.2096 (2)0.49468 (16)0.0292 (4)
H150.85920.17380.49120.035*
C160.6637 (3)0.3177 (2)0.42569 (16)0.0285 (4)
H160.77990.35850.37520.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05595 (17)0.03092 (13)0.03054 (13)0.00131 (10)0.01697 (10)0.00087 (8)
Cl10.0293 (3)0.0376 (3)0.0541 (3)0.0073 (2)0.0115 (2)0.0046 (2)
S10.0255 (2)0.0252 (2)0.0202 (2)0.00279 (19)0.00371 (18)0.00560 (17)
O10.0249 (7)0.0283 (7)0.0209 (6)0.0009 (6)0.0012 (5)0.0026 (5)
O20.0245 (7)0.0433 (8)0.0296 (7)0.0106 (6)0.0056 (6)0.0079 (6)
C10.0237 (9)0.0257 (9)0.0181 (8)0.0025 (8)0.0034 (7)0.0038 (7)
C20.0227 (9)0.0225 (8)0.0201 (8)0.0033 (7)0.0050 (7)0.0013 (7)
C30.0214 (9)0.0266 (9)0.0266 (9)0.0029 (8)0.0026 (7)0.0012 (7)
C40.0249 (10)0.0228 (9)0.0336 (10)0.0008 (8)0.0105 (8)0.0002 (7)
C50.0364 (11)0.0251 (9)0.0278 (9)0.0004 (8)0.0127 (8)0.0051 (7)
C60.0330 (11)0.0259 (9)0.0212 (9)0.0044 (8)0.0069 (8)0.0029 (7)
C70.0229 (9)0.0240 (9)0.0211 (8)0.0010 (7)0.0047 (7)0.0002 (7)
C80.0247 (9)0.0253 (9)0.0202 (8)0.0013 (8)0.0045 (7)0.0014 (7)
C90.0482 (14)0.0354 (11)0.0245 (10)0.0002 (10)0.0000 (9)0.0088 (8)
C100.0284 (10)0.0311 (10)0.0305 (10)0.0049 (9)0.0046 (8)0.0003 (8)
C110.0229 (9)0.0257 (9)0.0178 (8)0.0010 (7)0.0040 (7)0.0051 (7)
C120.0193 (9)0.0328 (10)0.0255 (9)0.0011 (8)0.0021 (7)0.0075 (8)
C130.0301 (11)0.0334 (10)0.0232 (9)0.0079 (9)0.0012 (8)0.0032 (8)
C140.0357 (11)0.0247 (9)0.0220 (9)0.0024 (8)0.0097 (8)0.0036 (7)
C150.0234 (10)0.0351 (10)0.0296 (10)0.0038 (8)0.0073 (8)0.0044 (8)
C160.0218 (9)0.0355 (11)0.0263 (9)0.0015 (8)0.0010 (8)0.0014 (8)
Geometric parameters (Å, º) top
Br1—C141.8972 (19)C8—C101.480 (3)
Cl1—C41.742 (2)C9—H9A0.9800
S1—O21.4907 (15)C9—H9B0.9800
S1—C11.7622 (17)C9—H9C0.9800
S1—C111.7990 (19)C10—H10A0.9800
O1—C81.371 (2)C10—H10B0.9800
O1—C71.384 (2)C10—H10C0.9800
C1—C81.358 (3)C11—C121.382 (3)
C1—C21.437 (3)C11—C161.392 (3)
C2—C71.392 (2)C12—C131.390 (3)
C2—C31.394 (3)C12—H120.9500
C3—C41.377 (3)C13—C141.377 (3)
C3—H30.9500C13—H130.9500
C4—C51.399 (3)C14—C151.386 (3)
C5—C61.391 (3)C15—C161.380 (3)
C5—H50.9500C15—H150.9500
C6—C71.379 (3)C16—H160.9500
C6—C91.503 (3)
O2—S1—C1107.21 (9)C6—C9—H9B109.5
O2—S1—C11106.44 (9)H9A—C9—H9B109.5
C1—S1—C1197.25 (8)C6—C9—H9C109.5
C8—O1—C7106.52 (13)H9A—C9—H9C109.5
C8—C1—C2107.65 (16)H9B—C9—H9C109.5
C8—C1—S1124.42 (15)C8—C10—H10A109.5
C2—C1—S1127.88 (14)C8—C10—H10B109.5
C7—C2—C3119.18 (18)H10A—C10—H10B109.5
C7—C2—C1104.93 (17)C8—C10—H10C109.5
C3—C2—C1135.88 (17)H10A—C10—H10C109.5
C4—C3—C2116.76 (17)H10B—C10—H10C109.5
C4—C3—H3121.6C12—C11—C16121.24 (18)
C2—C3—H3121.6C12—C11—S1119.47 (14)
C3—C4—C5123.07 (18)C16—C11—S1119.13 (14)
C3—C4—Cl1117.96 (15)C11—C12—C13119.01 (18)
C5—C4—Cl1118.97 (16)C11—C12—H12120.5
C6—C5—C4120.94 (18)C13—C12—H12120.5
C6—C5—H5119.5C14—C13—C12119.35 (18)
C4—C5—H5119.5C14—C13—H13120.3
C7—C6—C5114.94 (16)C12—C13—H13120.3
C7—C6—C9121.98 (19)C13—C14—C15121.87 (18)
C5—C6—C9123.08 (18)C13—C14—Br1120.01 (15)
C6—C7—O1124.64 (16)C15—C14—Br1118.11 (15)
C6—C7—C2125.08 (19)C16—C15—C14118.83 (18)
O1—C7—C2110.28 (16)C16—C15—H15120.6
C1—C8—O1110.62 (17)C14—C15—H15120.6
C1—C8—C10133.30 (17)C15—C16—C11119.59 (18)
O1—C8—C10116.07 (16)C15—C16—H16120.2
C6—C9—H9A109.5C11—C16—H16120.2
O2—S1—C1—C8140.11 (16)C1—C2—C7—C6179.24 (18)
C11—S1—C1—C8110.13 (17)C3—C2—C7—O1179.36 (15)
O2—S1—C1—C237.03 (19)C1—C2—C7—O10.1 (2)
C11—S1—C1—C272.73 (18)C2—C1—C8—O10.9 (2)
C8—C1—C2—C70.5 (2)S1—C1—C8—O1178.55 (13)
S1—C1—C2—C7178.04 (14)C2—C1—C8—C10179.3 (2)
C8—C1—C2—C3178.6 (2)S1—C1—C8—C103.1 (3)
S1—C1—C2—C31.1 (3)C7—O1—C8—C10.9 (2)
C7—C2—C3—C40.1 (3)C7—O1—C8—C10179.63 (16)
C1—C2—C3—C4179.0 (2)O2—S1—C11—C1213.18 (18)
C2—C3—C4—C51.3 (3)C1—S1—C11—C12123.58 (16)
C2—C3—C4—Cl1178.72 (14)O2—S1—C11—C16171.25 (15)
C3—C4—C5—C61.2 (3)C1—S1—C11—C1660.86 (17)
Cl1—C4—C5—C6178.83 (14)C16—C11—C12—C133.2 (3)
C4—C5—C6—C70.2 (3)S1—C11—C12—C13178.65 (15)
C4—C5—C6—C9179.95 (19)C11—C12—C13—C140.8 (3)
C5—C6—C7—O1179.37 (16)C12—C13—C14—C151.2 (3)
C9—C6—C7—O10.5 (3)C12—C13—C14—Br1179.12 (15)
C5—C6—C7—C21.6 (3)C13—C14—C15—C160.8 (3)
C9—C6—C7—C2178.61 (18)Br1—C14—C15—C16179.46 (15)
C8—O1—C7—C6179.79 (18)C14—C15—C16—C111.5 (3)
C8—O1—C7—C20.60 (19)C12—C11—C16—C153.5 (3)
C3—C2—C7—C61.5 (3)S1—C11—C16—C15179.03 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.952.503.249 (2)136
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H12BrClO2S
Mr383.68
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.1266 (3), 10.0247 (5), 12.6630 (7)
α, β, γ (°)84.749 (3), 79.235 (2), 86.443 (3)
V3)760.03 (7)
Z2
Radiation typeMo Kα
µ (mm1)3.02
Crystal size (mm)0.33 × 0.23 × 0.16
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.506, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
13853, 3794, 3209
Rint0.041
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.082, 1.05
No. of reflections3794
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.72

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
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.952.503.249 (2)135.6
Symmetry code: (i) x, y+1, z+1.
 

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

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChoi, H. D., Seo, P. J. & Lee, U. (2012a). Acta Cryst. E68, o2027.  CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J. & Lee, U. (2012b). Acta Cryst. E68, o2080.  CSD CrossRef IUCr Journals Google Scholar
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