Crystal structure of 3-(4-bromo­phenyl­sulfon­yl)-2,5,6-trimethyl-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814022119

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages 325-327

doi:10.1107/S1600536814022119

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Crystal structure of 3-(4-bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran

Hong Dae Choi ^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

Edited by G. M. Rosair, Heriot-Watt University, Scotland (Received 25 September 2014; accepted 7 October 2014; online 11 October 2014)

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-bromophenyl ring is 89.29 (6)°. In the crystal, molecules are linked into a chain along the b-axis direction by C—H⋯π hydrogen bonds and C—Br⋯π [3.626 (1) Å] interactions.

Keywords: crystal structure; benzofuran; 4-bromophenyl; Br⋯π contacts and and C—H⋯π hydrogen bonds..

CCDC reference: 1027923

1. Chemical context

Molecules containing a benzofuran ring show significant biological properties, such as antibacterial and antifungal (Aslam et al., 2009 ), antitumor and antiviral (Galal et al., 2009 ) and antimicrobial activities (Wahab Khan et al., 2005 ), and are potential inhibitors of β-amyloid aggregation (Ono et al., 2002 ). Benzofuran compounds occur widely in nature (Akgul & Anil, 2003 ; Soekamto et al., 2003 ). As a part of our continuing project concerning 3-(arylsulfonyl)-2,5,7-trimethyl-1-benzofuran derivatives, we report herein on the synthesis and crystal structure of the title compound.

2. Structural commentary

In the title molecule (Fig. 1), the benzofuran unit (O1/C1–C8) is essentially planar, with a mean deviation of 0.015 (2) Å from the mean plane defined by the nine constituent atoms. The 4-bromophenyl ring (C12–C17) is inclined to the benzofuran ring by 89.29 (6)°. The title compound crystallized in the non-centrosymmetric space group Pc in spite of having no asymmetric C atoms.

Figure 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 shown as small spheres of arbitrary radius.

3. Supramolecular features

In the crystal, molecules are linked into a chain along the b-axis direction by C—H⋯π hydrogen bonds (Fig. 2 and Table 1), and by C15—Br1⋯π interactions between the Br atom and the benzene ring of a neighbouring molecule with a Br1⋯Cg1ⁱⁱ separation of 3.626 (1) Å [illustrated in Fig. 2; Cg1 is the centroid of the C2–C7 benzene ring; symmetry code: (ii) x + 1, y, z].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1ⁱ	0.98	2.89	3.504 (3)	122
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
A view of the C—H⋯π and C—Br⋯π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) x, −y + 1, z + $[{1\over 2}]$ ; (ii) x + 1, y, z; (iii) x, −y + 1, z − $[{1\over 2}]$ ; (iv) x − 1, y, z.]

4. Database survey

A search of the Cambridge Structural Database (Version 5.35, last update May 2014; Groom & Allen, 2014 ) for 3-(arylsulfonyl)benzofuran gave 66 hits. Six of these are 3-arylsulfonyl-2,5,7-trimethyl-1-benzofuran derivatives whose structures are closely related to that of the title compound. In these six compounds, the dihedral angle between the arylsulfonyl ring and the benzofuran ring varies from ca 72.67° in 3-(4-fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran (Choi et al., 2010 ) to 87.61° in 3-(2-fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran (Choi et al., 2014 ). These dihedral angles are slightly smaller than the same angle of the title compound [89.29 (6)°].

5. Synthesis and crystallization

The starting material 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran was prepared by a literature method (Choi et al., 1999 ). 3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 10 h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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 77%, 263 mg; m.p. 452–453 K; R_F = 0.58 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (24 mg) in ethyl acetate (20 ml) at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 for aryl and 0.98 Å for methyl H atoms, and with U_iso(H) = 1.2U_eq(C) for aryl and 1.5U_eq(C) for methyl H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₃S
M_r	379.26
Crystal system, space group	Monoclinic, Pc
Temperature (K)	173
a, b, c (Å)	11.3395 (3), 8.0093 (2), 9.0439 (2)
β (°)	108.800 (1)
V (Å³)	777.56 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.79
Crystal size (mm)	0.21 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.643, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12777, 3392, 3136
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.056, 1.00
No. of reflections	3392
No. of parameters	202
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.37
Absolute structure	Flack (1983 ), 1710 Friedel pairs
Absolute structure parameter	−0.001 (6)
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ).

Supporting information

CCDC reference: 1027923

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814022119/rn2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022119/rn2128Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022119/rn2128Isup3.cml

checkCIF report

Chemical context top

Molecules containing a benzofuran ring show significant biological properties, such as antibacterial and antifungal (Aslam et al., 2009), antitumor and antiviral (Galal et al., 2009) and antimicrobial activities (Wahab Khan et al., 2005), and are potential inhibitors of β-amyloid aggregation (Ono et al., 2002). Benzofuran compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing project concerning 3-(arylsulfonyl)-2,5,7-trimethyl-1-benzofuran derivatives, we report herein on the synthesis and crystal structure of the title compound.

Structural commentary top

In the title molecule (Fig. 1), the benzofuran unit (O1/C1–C8) is essentially planar, with a mean deviation of 0.015 (2) Å from the mean plane defined by the nine constituent atoms. The 4-bromophenyl ring (C12–C17) is inclined to the benzofuran ring by 89.29 (6)°. The title compound is crystallized in the non-centrosymmetric space group Pc in spite of having no asymmetric C atoms.

Supramolecular features top

In the crystal, molecules are linked into a chain along the b-axis direction by C—H···π hydrogen bonds (Fig. 2 and Table 1), and by C15—Br1···π interactions between the Br atom and the benzene ring of a neighbouring molecule with a Br1···Cg1ⁱⁱ separation of 3.626 (1) Å [illustrated in Fig. 2; Cg1 is the centroid of the C2–C7 benzene ring; symmetry code: (ii) x+1, y, z].

Database survey top

A search of the Cambridge Structural Database (Version 5.35, last update May 2014; Groom & Allen, 2014) for 3-(arylsulfonyl)benzofuran gave 66 hits. Six of these involve 3-arylsulfonyl-2,5,7-trimethyl-1-benzofuran derivatives whose structures are closely related to that of the title compound. In these six compounds, the dihedral angle between the arylsulfonyl ring and the benzofuran ring varies from ca 72.67° in 3-(4-fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran (Choi et al., 2010) to 87.61° in 3-(2-fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran (Choi et al., 2014). These dihedral angles are slightly smaller than the same angle of the title compound [89.29 (6)°].

Synthesis and crystallization top

The starting material 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran was prepared by a literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,5,6-trimethyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 10 h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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 77%, 263 mg; m.p. 452–453 K; R_F = 0.58 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (24 mg) in ethyl acetate (20 ml) at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 for aryl and 0.98 Å for methyl H atoms. U_iso(H) = 1.2U_eq(C) for aryl and 1.5U_eq(C)) for methyl H atoms. The positions of methyl hydrogens were optimized using the AFIX137 command in SHELXL97 (Sheldrick, 2008).

Related literature top

For related literature, see: Akgul & Anil (2003); Allen (2002); Aslam et al. (2009); Choi et al. (1999, 2010, 2014); Galal et al. (2009); Wahab Khan et al. (2005); Ono et al. (2002); Sheldrick (2008); Soekamto et al. (2003).

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

The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

A view of the C—H···π and C—Br···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding are omitted for clarity. [Symmetry codes: (i) x, -y+1, z+1/2; (ii) x+1, y, z; (iii) x, -y+1, z-1/2; (iv) x-1, y, z.]

3-(4-Bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₃S	F(000) = 384
M_r = 379.26	D_x = 1.620 Mg m⁻³
Monoclinic, Pc	Melting point = 453–452 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.3395 (3) Å	Cell parameters from 6185 reflections
b = 8.0093 (2) Å	θ = 2.5–27.5°
c = 9.0439 (2) Å	µ = 2.79 mm⁻¹
β = 108.800 (1)°	T = 173 K
V = 777.56 (3) Å³	Block, colourless
Z = 2	0.21 × 0.17 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3392 independent reflections
Radiation source: rotating anode	3136 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.643, T_max = 0.746	l = −11→11
12777 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0201P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3392 reflections	Δρ_max = 0.32 e Å⁻³
202 parameters	Δρ_min = −0.37 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1710 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.001 (6)

Crystal data top

C₁₇H₁₅BrO₃S	V = 777.56 (3) Å³
M_r = 379.26	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 11.3395 (3) Å	µ = 2.79 mm⁻¹
b = 8.0093 (2) Å	T = 173 K
c = 9.0439 (2) Å	0.21 × 0.17 × 0.15 mm
β = 108.800 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3392 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3136 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.746	R_int = 0.030
12777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.056	Δρ_max = 0.32 e Å⁻³
S = 1.00	Δρ_min = −0.37 e Å⁻³
3392 reflections	Absolute structure: Flack (1983), 1710 Friedel pairs
202 parameters	Absolute structure parameter: −0.001 (6)
2 restraints

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl₃, 400 Hz): 7.85 (d, J = 8.56 Hz, 2H), 7.63 (d, J = 8.21 Hz, 2H), 7.58 (s, 1H), 7.20(s, 1H), 2.76 (s, 3H), 2.34 (s, 3H), 2.32 (s, 3H)).

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	0.89314 (3)	0.76274 (4)	0.54426 (3)	0.04023 (8)
S1	0.49513 (5)	0.71962 (7)	0.90695 (6)	0.02534 (13)
O1	0.27996 (15)	0.39863 (18)	0.61667 (18)	0.0275 (4)
O2	0.44621 (15)	0.8818 (2)	0.92194 (19)	0.0325 (4)
O3	0.54542 (16)	0.6177 (2)	1.04338 (19)	0.0357 (4)
C1	0.3808 (2)	0.6097 (2)	0.7663 (2)	0.0212 (4)
C2	0.2883 (2)	0.6820 (3)	0.6333 (2)	0.0229 (4)
C3	0.2506 (2)	0.8416 (3)	0.5766 (3)	0.0256 (5)
H3	0.2894	0.9370	0.6343	0.031*
C4	0.1567 (2)	0.8602 (3)	0.4364 (3)	0.0278 (5)
C5	0.0994 (2)	0.7185 (3)	0.3471 (3)	0.0301 (6)
C6	0.1362 (2)	0.5613 (3)	0.4028 (3)	0.0305 (5)
H6	0.0986	0.4653	0.3451	0.037*
C7	0.22934 (19)	0.5462 (3)	0.5449 (3)	0.0239 (5)
C8	0.3733 (2)	0.4408 (3)	0.7508 (3)	0.0258 (5)
C9	0.1161 (3)	1.0346 (3)	0.3779 (3)	0.0373 (6)
H9A	0.1698	1.1164	0.4489	0.056*
H9B	0.0295	1.0520	0.3740	0.056*
H9C	0.1224	1.0485	0.2731	0.056*
C10	−0.0008 (3)	0.7398 (3)	0.1912 (3)	0.0429 (7)
H10A	−0.0211	0.6310	0.1397	0.064*
H10B	0.0289	0.8152	0.1255	0.064*
H10C	−0.0755	0.7872	0.2071	0.064*
C11	0.4438 (3)	0.3001 (3)	0.8427 (3)	0.0360 (6)
H11A	0.4959	0.3405	0.9453	0.054*
H11B	0.4968	0.2505	0.7876	0.054*
H11C	0.3856	0.2157	0.8564	0.054*
C12	0.6123 (2)	0.7434 (3)	0.8190 (3)	0.0238 (5)
C13	0.6082 (2)	0.8757 (3)	0.7190 (3)	0.0303 (5)
H12	0.5469	0.9605	0.7046	0.036*
C14	0.6935 (2)	0.8833 (3)	0.6407 (3)	0.0334 (6)
H13	0.6915	0.9737	0.5719	0.040*
C15	0.7818 (3)	0.7605 (3)	0.6615 (3)	0.0293 (5)
C16	0.7893 (2)	0.6306 (3)	0.7645 (3)	0.0349 (6)
H15	0.8527	0.5485	0.7810	0.042*
C17	0.7032 (2)	0.6216 (3)	0.8436 (3)	0.0303 (5)
H16	0.7065	0.5325	0.9141	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03614 (13)	0.05357 (16)	0.03812 (15)	−0.01553 (15)	0.02190 (11)	−0.01138 (13)
S1	0.0241 (3)	0.0324 (3)	0.0203 (3)	0.0013 (3)	0.0082 (2)	−0.0013 (2)
O1	0.0323 (9)	0.0210 (8)	0.0336 (9)	−0.0030 (7)	0.0169 (8)	−0.0009 (6)
O2	0.0313 (9)	0.0347 (9)	0.0323 (9)	0.0021 (7)	0.0112 (7)	−0.0124 (7)
O3	0.0357 (9)	0.0502 (11)	0.0226 (8)	0.0051 (8)	0.0114 (7)	0.0069 (7)
C1	0.0213 (11)	0.0242 (10)	0.0208 (10)	0.0003 (9)	0.0103 (9)	0.0011 (8)
C2	0.0228 (11)	0.0243 (11)	0.0255 (12)	−0.0008 (9)	0.0133 (9)	0.0007 (8)
C3	0.0251 (11)	0.0244 (11)	0.0317 (12)	0.0005 (9)	0.0153 (9)	0.0010 (9)
C4	0.0250 (12)	0.0338 (13)	0.0299 (13)	0.0008 (9)	0.0161 (10)	0.0038 (9)
C5	0.0234 (13)	0.0464 (14)	0.0242 (13)	0.0020 (10)	0.0129 (11)	0.0049 (10)
C6	0.0252 (12)	0.0384 (13)	0.0309 (14)	−0.0081 (10)	0.0134 (11)	−0.0089 (10)
C7	0.0238 (11)	0.0229 (11)	0.0296 (13)	−0.0006 (9)	0.0148 (10)	−0.0005 (9)
C8	0.0270 (12)	0.0294 (11)	0.0273 (12)	0.0029 (9)	0.0174 (10)	0.0043 (9)
C9	0.0347 (13)	0.0419 (16)	0.0367 (13)	0.0083 (12)	0.0133 (11)	0.0108 (11)
C10	0.0337 (15)	0.0618 (19)	0.0312 (16)	0.0002 (12)	0.0075 (13)	0.0040 (12)
C11	0.0455 (15)	0.0251 (12)	0.0447 (16)	0.0075 (11)	0.0245 (13)	0.0107 (10)
C12	0.0223 (11)	0.0286 (11)	0.0198 (12)	−0.0025 (9)	0.0058 (10)	−0.0033 (8)
C13	0.0296 (12)	0.0283 (12)	0.0331 (13)	0.0018 (10)	0.0105 (10)	0.0006 (10)
C14	0.0346 (14)	0.0358 (14)	0.0305 (13)	−0.0040 (11)	0.0117 (11)	0.0044 (10)
C15	0.0241 (12)	0.0400 (13)	0.0256 (13)	−0.0092 (10)	0.0107 (10)	−0.0073 (9)
C16	0.0268 (12)	0.0400 (14)	0.0399 (14)	0.0035 (11)	0.0135 (11)	0.0043 (11)
C17	0.0280 (12)	0.0338 (13)	0.0308 (13)	0.0070 (10)	0.0115 (10)	0.0095 (10)

Geometric parameters (Å, º) top

Br1—C15	1.892 (3)	C9—H9A	0.9800
S1—O3	1.4354 (17)	C9—H9B	0.9800
S1—O2	1.4360 (17)	C9—H9C	0.9800
S1—C1	1.735 (2)	C10—H10A	0.9800
S1—C12	1.765 (3)	C10—H10B	0.9800
O1—C8	1.371 (3)	C10—H10C	0.9800
O1—C7	1.381 (2)	C11—H11A	0.9800
C1—C8	1.360 (3)	C11—H11B	0.9800
C1—C2	1.439 (3)	C11—H11C	0.9800
C2—C7	1.388 (3)	C12—C17	1.384 (3)
C2—C3	1.392 (3)	C12—C13	1.384 (3)
C3—C4	1.376 (3)	C13—C14	1.372 (3)
C3—H3	0.9500	C13—H12	0.9500
C4—C5	1.423 (3)	C14—C15	1.372 (4)
C4—C9	1.512 (3)	C14—H13	0.9500
C5—C6	1.370 (3)	C15—C16	1.381 (4)
C5—C10	1.508 (4)	C16—C17	1.386 (3)
C6—C7	1.381 (3)	C16—H15	0.9500
C6—H6	0.9500	C17—H16	0.9500
C8—C11	1.473 (3)

O3—S1—O2	119.46 (10)	C4—C9—H9C	109.5
O3—S1—C1	109.74 (10)	H9A—C9—H9C	109.5
O2—S1—C1	107.95 (10)	H9B—C9—H9C	109.5
O3—S1—C12	107.50 (11)	C5—C10—H10A	109.5
O2—S1—C12	108.34 (11)	C5—C10—H10B	109.5
C1—S1—C12	102.55 (11)	H10A—C10—H10B	109.5
C8—O1—C7	106.92 (16)	C5—C10—H10C	109.5
C8—C1—C2	108.04 (19)	H10A—C10—H10C	109.5
C8—C1—S1	125.97 (18)	H10B—C10—H10C	109.5
C2—C1—S1	125.47 (16)	C8—C11—H11A	109.5
C7—C2—C3	118.3 (2)	C8—C11—H11B	109.5
C7—C2—C1	104.63 (19)	H11A—C11—H11B	109.5
C3—C2—C1	137.1 (2)	C8—C11—H11C	109.5
C4—C3—C2	119.6 (2)	H11A—C11—H11C	109.5
C4—C3—H3	120.2	H11B—C11—H11C	109.5
C2—C3—H3	120.2	C17—C12—C13	120.7 (2)
C3—C4—C5	120.8 (2)	C17—C12—S1	118.77 (18)
C3—C4—C9	118.7 (2)	C13—C12—S1	120.39 (19)
C5—C4—C9	120.4 (2)	C14—C13—C12	119.4 (2)
C6—C5—C4	119.7 (2)	C14—C13—H12	120.3
C6—C5—C10	119.8 (2)	C12—C13—H12	120.3
C4—C5—C10	120.6 (2)	C15—C14—C13	120.1 (2)
C5—C6—C7	118.3 (2)	C15—C14—H13	119.9
C5—C6—H6	120.8	C13—C14—H13	119.9
C7—C6—H6	120.8	C14—C15—C16	121.1 (3)
O1—C7—C6	126.2 (2)	C14—C15—Br1	120.3 (2)
O1—C7—C2	110.48 (19)	C16—C15—Br1	118.5 (2)
C6—C7—C2	123.3 (2)	C15—C16—C17	119.1 (2)
C1—C8—O1	109.9 (2)	C15—C16—H15	120.4
C1—C8—C11	134.3 (2)	C17—C16—H15	120.4
O1—C8—C11	115.8 (2)	C12—C17—C16	119.5 (2)
C4—C9—H9A	109.5	C12—C17—H16	120.2
C4—C9—H9B	109.5	C16—C17—H16	120.2
H9A—C9—H9B	109.5

O3—S1—C1—C8	−26.6 (2)	C1—C2—C7—O1	0.4 (2)
O2—S1—C1—C8	−158.29 (18)	C3—C2—C7—C6	0.7 (3)
C12—S1—C1—C8	87.4 (2)	C1—C2—C7—C6	−177.6 (2)
O3—S1—C1—C2	162.75 (18)	C2—C1—C8—O1	−0.9 (2)
O2—S1—C1—C2	31.0 (2)	S1—C1—C8—O1	−172.93 (15)
C12—S1—C1—C2	−83.2 (2)	C2—C1—C8—C11	177.4 (3)
C8—C1—C2—C7	0.3 (2)	S1—C1—C8—C11	5.4 (4)
S1—C1—C2—C7	172.36 (16)	C7—O1—C8—C1	1.2 (2)
C8—C1—C2—C3	−177.5 (2)	C7—O1—C8—C11	−177.5 (2)
S1—C1—C2—C3	−5.4 (4)	O3—S1—C12—C17	25.8 (2)
C7—C2—C3—C4	0.3 (3)	O2—S1—C12—C17	156.21 (19)
C1—C2—C3—C4	177.8 (2)	C1—S1—C12—C17	−89.8 (2)
C2—C3—C4—C5	−1.3 (3)	O3—S1—C12—C13	−158.47 (19)
C2—C3—C4—C9	179.2 (2)	O2—S1—C12—C13	−28.1 (2)
C3—C4—C5—C6	1.4 (4)	C1—S1—C12—C13	85.9 (2)
C9—C4—C5—C6	−179.1 (2)	C17—C12—C13—C14	1.6 (4)
C3—C4—C5—C10	−178.2 (2)	S1—C12—C13—C14	−173.97 (18)
C9—C4—C5—C10	1.3 (4)	C12—C13—C14—C15	0.1 (4)
C4—C5—C6—C7	−0.4 (4)	C13—C14—C15—C16	−2.1 (4)
C10—C5—C6—C7	179.2 (2)	C13—C14—C15—Br1	176.07 (19)
C8—O1—C7—C6	177.0 (2)	C14—C15—C16—C17	2.3 (4)
C8—O1—C7—C2	−1.0 (2)	Br1—C15—C16—C17	−175.84 (18)
C5—C6—C7—O1	−178.3 (2)	C13—C12—C17—C16	−1.4 (4)
C5—C6—C7—C2	−0.6 (3)	S1—C12—C17—C16	174.32 (19)
C3—C2—C7—O1	178.70 (17)	C15—C16—C17—C12	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.98	2.89	3.504 (3)	122

Symmetry code: (i) x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.98	2.89	3.504 (3)	121.6

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₃S
M_r	379.26
Crystal system, space group	Monoclinic, Pc
Temperature (K)	173
a, b, c (Å)	11.3395 (3), 8.0093 (2), 9.0439 (2)
β (°)	108.800 (1)
V (Å³)	777.56 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.79
Crystal size (mm)	0.21 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.643, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12777, 3392, 3136
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.056, 1.00
No. of reflections	3392
No. of parameters	202
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.37
Absolute structure	Flack (1983), 1710 Friedel pairs
Absolute structure parameter	−0.001 (6)

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

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

References

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Volume 70| Part 11| November 2014| Pages 325-327

doi:10.1107/S1600536814022119

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 3-(4-bromo­phenyl­sulfon­yl)-2,5,6-tri­methyl-1-benzo­furan

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of 3-(4-bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran

3. Supramolecular features