3-(4-Bromo­phenyl­sulfin­yl)-5-cyclo­hexyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811054158

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o205

doi:10.1107/S1600536811054158

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3-(4-Bromophenylsulfinyl)-5-cyclohexyl-2-methyl-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 14 December 2011; accepted 15 December 2011; online 21 December 2011)

In the title compound, C₂₁H₂₁BrO₂S, the cyclohexyl ring adopts a chair conformation. The 4-bromophenyl ring makes a dihedral angle of 81.62 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distances = 3.540 (3) Å, interplanar distance = 3.481 (3) Å and slippage = 0.644 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the crystal structures of related compounds, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₂₁H₂₁BrO₂S
M_r = 417.35
Monoclinic, P 2₁ /c
a = 16.7340 (4) Å
b = 8.8290 (2) Å
c = 13.0178 (3) Å
β = 105.197 (1)°
V = 1856.05 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 173 K
0.25 × 0.23 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.561, T_max = 0.746
17836 measured reflections
4653 independent reflections
3467 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.04
4653 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.95	2.47	3.112 (3)	125
C15—H15B⋯Cg2ⁱⁱ	0.98	3.06	3.532 (3)	111
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

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, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054158/ff2048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054158/ff2048Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054158/ff2048Isup3.cml

checkCIF report

Comment top

Substituted benzofuran derivatives have drawn much interest due to their valuable biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of 5-cyclohexyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfinyl) (Choi et al., 2011a) or 3-phenylsulfinyl (Choi et al., 2011b) substituents, 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 0.004 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has the chair form. The dihedral angle formed by the 4-bromophenyl ring and the mean plane of the benzofuran fragment is 81.62 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1; first entry) and intermolecular C—H···π interactions (Table 1; second entry, Cg2 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) is further stabilized by a weak slipped π···π interaction between the furan rings of adjacent molecules, with a Cg1···Cg1ⁱⁱ distance of 3.540 (3) Å and an interplanar distance of 3.481 (3) Å resulting in a slippage of 0.644 (3) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the crystal structures of related compounds, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-cyclohexyl-2-methyl-1-benzofuran (321 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 6h, 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 71%, m.p. 461–462 K; R_f = 0.47 (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.

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, 1997) 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.
	Fig. 2. A view of the C—H···O, C—H···π and π···π interactions (dotted lines). H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x, - y + 3/2, z - 1/2; (ii) - x, - y + 1, - z + 1; (iii) x, - y + 3/2, z + 1/2 .]

3-(4-Bromophenylsulfinyl)-5-cyclohexyl-2-methyl-1-benzofuran top

Crystal data top

C₂₁H₂₁BrO₂S	F(000) = 856
M_r = 417.35	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6823 reflections
a = 16.7340 (4) Å	θ = 2.5–25.9°
b = 8.8290 (2) Å	µ = 2.34 mm⁻¹
c = 13.0178 (3) Å	T = 173 K
β = 105.197 (1)°	Block, colourless
V = 1856.05 (7) Å³	0.25 × 0.23 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4653 independent reflections
Radiation source: rotating anode	3467 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.039
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.3°
ϕ and ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→11
T_min = 0.561, T_max = 0.746	l = −17→15
17836 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0422P)² + 0.7692P] where P = (F_o² + 2F_c²)/3
4653 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₂₁H₂₁BrO₂S	V = 1856.05 (7) Å³
M_r = 417.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.7340 (4) Å	µ = 2.34 mm⁻¹
b = 8.8290 (2) Å	T = 173 K
c = 13.0178 (3) Å	0.25 × 0.23 × 0.11 mm
β = 105.197 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4653 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3467 reflections with I > 2σ(I)
T_min = 0.561, T_max = 0.746	R_int = 0.039
17836 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	Δρ_max = 0.52 e Å⁻³
4653 reflections	Δρ_min = −0.61 e Å⁻³
227 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	0.468766 (17)	0.59993 (4)	0.30483 (2)	0.06137 (12)
S1	0.13569 (3)	0.72783 (5)	0.44840 (4)	0.03017 (13)
O1	0.03213 (8)	0.32472 (16)	0.40283 (11)	0.0312 (3)
O2	0.15901 (10)	0.78663 (16)	0.55882 (12)	0.0384 (4)
C1	0.10321 (12)	0.5392 (2)	0.45372 (15)	0.0259 (4)
C2	0.13294 (12)	0.4289 (2)	0.53755 (16)	0.0246 (4)
C3	0.19099 (12)	0.4260 (2)	0.63618 (16)	0.0253 (4)
H3	0.2228	0.5135	0.6625	0.030*
C4	0.20162 (12)	0.2931 (2)	0.69560 (16)	0.0267 (4)
C5	0.15359 (13)	0.1661 (2)	0.65496 (18)	0.0328 (5)
H5	0.1613	0.0759	0.6962	0.039*
C6	0.09542 (13)	0.1663 (2)	0.55754 (18)	0.0335 (5)
H6	0.0635	0.0790	0.5309	0.040*
C7	0.08631 (12)	0.2995 (2)	0.50145 (16)	0.0279 (4)
C8	0.04359 (12)	0.4725 (2)	0.37654 (16)	0.0285 (4)
C9	0.26423 (12)	0.2852 (2)	0.80359 (16)	0.0287 (4)
H9	0.2630	0.1795	0.8308	0.034*
C10	0.35211 (13)	0.3162 (3)	0.79681 (18)	0.0404 (5)
H10A	0.3547	0.4182	0.7663	0.048*
H10B	0.3675	0.2412	0.7487	0.048*
C11	0.41427 (14)	0.3071 (3)	0.90723 (19)	0.0435 (6)
H11A	0.4164	0.2018	0.9340	0.052*
H11B	0.4702	0.3341	0.9008	0.052*
C12	0.39071 (16)	0.4119 (3)	0.9856 (2)	0.0460 (6)
H12A	0.3950	0.5181	0.9633	0.055*
H12B	0.4298	0.3982	1.0566	0.055*
C13	0.30362 (16)	0.3820 (3)	0.99321 (19)	0.0480 (6)
H13A	0.2887	0.4573	1.0414	0.058*
H13B	0.3009	0.2801	1.0238	0.058*
C14	0.24169 (15)	0.3912 (3)	0.88407 (19)	0.0409 (5)
H14A	0.1859	0.3648	0.8911	0.049*
H14B	0.2397	0.4966	0.8575	0.049*
C15	−0.00823 (13)	0.5249 (3)	0.27284 (17)	0.0374 (5)
H15A	−0.0039	0.6352	0.2681	0.056*
H15B	−0.0660	0.4967	0.2660	0.056*
H15C	0.0108	0.4774	0.2154	0.056*
C16	0.22978 (13)	0.6877 (2)	0.41199 (15)	0.0275 (4)
C17	0.22676 (14)	0.6868 (2)	0.30470 (16)	0.0320 (5)
H17	0.1759	0.7059	0.2532	0.038*
C18	0.29773 (15)	0.6579 (2)	0.27262 (17)	0.0358 (5)
H18	0.2960	0.6548	0.1991	0.043*
C19	0.37075 (15)	0.6337 (3)	0.34865 (19)	0.0374 (5)
C20	0.37513 (14)	0.6356 (3)	0.45633 (19)	0.0388 (5)
H20	0.4263	0.6186	0.5076	0.047*
C21	0.30379 (13)	0.6628 (2)	0.48822 (17)	0.0337 (5)
H21	0.3055	0.6644	0.5617	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04820 (18)	0.0874 (2)	0.0565 (2)	−0.00961 (14)	0.02786 (14)	−0.00300 (14)
S1	0.0388 (3)	0.0241 (2)	0.0259 (3)	0.0038 (2)	0.0053 (2)	0.0013 (2)
O1	0.0262 (7)	0.0341 (8)	0.0312 (8)	−0.0033 (6)	0.0036 (6)	−0.0058 (6)
O2	0.0513 (9)	0.0334 (8)	0.0294 (8)	−0.0014 (7)	0.0086 (7)	−0.0065 (6)
C1	0.0268 (10)	0.0256 (10)	0.0244 (10)	0.0022 (8)	0.0050 (8)	−0.0019 (8)
C2	0.0238 (9)	0.0232 (9)	0.0277 (10)	0.0023 (7)	0.0083 (8)	−0.0011 (8)
C3	0.0250 (10)	0.0229 (9)	0.0278 (10)	−0.0009 (7)	0.0068 (8)	−0.0013 (8)
C4	0.0245 (9)	0.0268 (10)	0.0295 (11)	0.0028 (8)	0.0079 (8)	0.0023 (8)
C5	0.0322 (11)	0.0257 (10)	0.0412 (13)	0.0000 (8)	0.0110 (9)	0.0056 (9)
C6	0.0292 (11)	0.0263 (10)	0.0445 (13)	−0.0068 (8)	0.0089 (9)	−0.0030 (9)
C7	0.0215 (9)	0.0319 (11)	0.0302 (11)	−0.0005 (8)	0.0065 (8)	−0.0048 (8)
C8	0.0260 (10)	0.0318 (10)	0.0286 (11)	0.0031 (8)	0.0085 (8)	−0.0037 (8)
C9	0.0278 (10)	0.0243 (10)	0.0323 (11)	0.0014 (8)	0.0051 (8)	0.0069 (8)
C10	0.0278 (11)	0.0626 (15)	0.0306 (12)	0.0051 (10)	0.0074 (9)	0.0004 (11)
C11	0.0280 (11)	0.0610 (16)	0.0385 (13)	0.0035 (11)	0.0034 (10)	0.0069 (11)
C12	0.0514 (15)	0.0446 (14)	0.0345 (13)	−0.0050 (11)	−0.0023 (11)	0.0016 (10)
C13	0.0556 (16)	0.0619 (16)	0.0264 (12)	0.0096 (12)	0.0105 (11)	0.0013 (11)
C14	0.0390 (13)	0.0524 (14)	0.0341 (13)	0.0105 (10)	0.0145 (10)	0.0074 (10)
C15	0.0310 (11)	0.0516 (14)	0.0268 (11)	0.0063 (10)	0.0022 (9)	−0.0037 (10)
C16	0.0378 (11)	0.0208 (9)	0.0232 (10)	−0.0040 (8)	0.0067 (9)	0.0006 (7)
C17	0.0428 (12)	0.0264 (10)	0.0238 (10)	−0.0037 (9)	0.0033 (9)	0.0026 (8)
C18	0.0509 (14)	0.0330 (11)	0.0247 (11)	−0.0086 (10)	0.0120 (10)	0.0007 (9)
C19	0.0391 (12)	0.0377 (12)	0.0382 (13)	−0.0088 (10)	0.0151 (10)	−0.0013 (10)
C20	0.0341 (12)	0.0480 (13)	0.0311 (12)	−0.0070 (10)	0.0026 (9)	−0.0006 (10)
C21	0.0403 (12)	0.0374 (11)	0.0212 (10)	−0.0064 (9)	0.0040 (9)	−0.0003 (9)

Geometric parameters (Å, º) top

Br1—C19	1.896 (2)	C11—C12	1.505 (4)
S1—O2	1.4812 (15)	C11—H11A	0.9900
S1—C1	1.759 (2)	C11—H11B	0.9900
S1—C16	1.795 (2)	C12—C13	1.510 (4)
O1—C8	1.375 (3)	C12—H12A	0.9900
O1—C7	1.382 (2)	C12—H12B	0.9900
C1—C8	1.351 (3)	C13—C14	1.525 (3)
C1—C2	1.450 (3)	C13—H13A	0.9900
C2—C3	1.392 (3)	C13—H13B	0.9900
C2—C7	1.394 (3)	C14—H14A	0.9900
C3—C4	1.391 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.400 (3)	C15—H15B	0.9800
C4—C9	1.519 (3)	C15—H15C	0.9800
C5—C6	1.382 (3)	C16—C17	1.384 (3)
C5—H5	0.9500	C16—C21	1.386 (3)
C6—C7	1.372 (3)	C17—C18	1.382 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.475 (3)	C18—C19	1.373 (3)
C9—C10	1.521 (3)	C18—H18	0.9500
C9—C14	1.524 (3)	C19—C20	1.384 (3)
C9—H9	1.0000	C20—C21	1.384 (3)
C10—C11	1.540 (3)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900

O2—S1—C1	107.40 (9)	C10—C11—H11B	109.3
O2—S1—C16	107.42 (9)	H11A—C11—H11B	108.0
C1—S1—C16	97.18 (9)	C11—C12—C13	111.4 (2)
C8—O1—C7	106.49 (15)	C11—C12—H12A	109.3
C8—C1—C2	107.95 (17)	C13—C12—H12A	109.3
C8—C1—S1	123.96 (16)	C11—C12—H12B	109.3
C2—C1—S1	128.09 (15)	C13—C12—H12B	109.3
C3—C2—C7	119.31 (18)	H12A—C12—H12B	108.0
C3—C2—C1	136.49 (18)	C12—C13—C14	111.2 (2)
C7—C2—C1	104.20 (17)	C12—C13—H13A	109.4
C4—C3—C2	119.01 (18)	C14—C13—H13A	109.4
C4—C3—H3	120.5	C12—C13—H13B	109.4
C2—C3—H3	120.5	C14—C13—H13B	109.4
C3—C4—C5	119.23 (18)	H13A—C13—H13B	108.0
C3—C4—C9	120.69 (17)	C9—C14—C13	112.17 (19)
C5—C4—C9	120.08 (17)	C9—C14—H14A	109.2
C6—C5—C4	122.86 (19)	C13—C14—H14A	109.2
C6—C5—H5	118.6	C9—C14—H14B	109.2
C4—C5—H5	118.6	C13—C14—H14B	109.2
C7—C6—C5	116.29 (19)	H14A—C14—H14B	107.9
C7—C6—H6	121.9	C8—C15—H15A	109.5
C5—C6—H6	121.9	C8—C15—H15B	109.5
C6—C7—O1	125.95 (18)	H15A—C15—H15B	109.5
C6—C7—C2	123.30 (19)	C8—C15—H15C	109.5
O1—C7—C2	110.74 (17)	H15A—C15—H15C	109.5
C1—C8—O1	110.62 (17)	H15B—C15—H15C	109.5
C1—C8—C15	133.38 (19)	C17—C16—C21	120.7 (2)
O1—C8—C15	115.99 (17)	C17—C16—S1	117.72 (16)
C4—C9—C10	112.38 (17)	C21—C16—S1	121.55 (16)
C4—C9—C14	111.90 (17)	C18—C17—C16	119.9 (2)
C10—C9—C14	110.29 (18)	C18—C17—H17	120.0
C4—C9—H9	107.3	C16—C17—H17	120.0
C10—C9—H9	107.3	C19—C18—C17	118.9 (2)
C14—C9—H9	107.3	C19—C18—H18	120.5
C9—C10—C11	111.30 (18)	C17—C18—H18	120.5
C9—C10—H10A	109.4	C18—C19—C20	121.9 (2)
C11—C10—H10A	109.4	C18—C19—Br1	118.97 (18)
C9—C10—H10B	109.4	C20—C19—Br1	119.09 (18)
C11—C10—H10B	109.4	C21—C20—C19	119.0 (2)
H10A—C10—H10B	108.0	C21—C20—H20	120.5
C12—C11—C10	111.59 (19)	C19—C20—H20	120.5
C12—C11—H11A	109.3	C20—C21—C16	119.5 (2)
C10—C11—H11A	109.3	C20—C21—H21	120.3
C12—C11—H11B	109.3	C16—C21—H21	120.3

O2—S1—C1—C8	146.84 (17)	C7—O1—C8—C15	179.75 (17)
C16—S1—C1—C8	−102.33 (18)	C3—C4—C9—C10	−60.3 (2)
O2—S1—C1—C2	−32.9 (2)	C5—C4—C9—C10	119.9 (2)
C16—S1—C1—C2	77.98 (19)	C3—C4—C9—C14	64.4 (2)
C8—C1—C2—C3	−178.9 (2)	C5—C4—C9—C14	−115.3 (2)
S1—C1—C2—C3	0.8 (4)	C4—C9—C10—C11	−179.87 (18)
C8—C1—C2—C7	0.1 (2)	C14—C9—C10—C11	54.5 (3)
S1—C1—C2—C7	179.79 (15)	C9—C10—C11—C12	−55.4 (3)
C7—C2—C3—C4	0.8 (3)	C10—C11—C12—C13	55.4 (3)
C1—C2—C3—C4	179.7 (2)	C11—C12—C13—C14	−55.1 (3)
C2—C3—C4—C5	−0.2 (3)	C4—C9—C14—C13	179.11 (19)
C2—C3—C4—C9	−179.96 (17)	C10—C9—C14—C13	−55.0 (3)
C3—C4—C5—C6	0.0 (3)	C12—C13—C14—C9	55.4 (3)
C9—C4—C5—C6	179.74 (19)	O2—S1—C16—C17	−156.18 (15)
C4—C5—C6—C7	−0.3 (3)	C1—S1—C16—C17	92.99 (16)
C5—C6—C7—O1	179.92 (18)	O2—S1—C16—C21	21.95 (19)
C5—C6—C7—C2	0.9 (3)	C1—S1—C16—C21	−88.88 (18)
C8—O1—C7—C6	−179.9 (2)	C21—C16—C17—C18	1.2 (3)
C8—O1—C7—C2	−0.8 (2)	S1—C16—C17—C18	179.39 (15)
C3—C2—C7—C6	−1.2 (3)	C16—C17—C18—C19	−1.4 (3)
C1—C2—C7—C6	179.60 (19)	C17—C18—C19—C20	0.8 (3)
C3—C2—C7—O1	179.69 (17)	C17—C18—C19—Br1	−178.19 (15)
C1—C2—C7—O1	0.5 (2)	C18—C19—C20—C21	−0.1 (3)
C2—C1—C8—O1	−0.6 (2)	Br1—C19—C20—C21	178.94 (17)
S1—C1—C8—O1	179.68 (13)	C19—C20—C21—C16	−0.1 (3)
C2—C1—C8—C15	−179.2 (2)	C17—C16—C21—C20	−0.5 (3)
S1—C1—C8—C15	1.1 (3)	S1—C16—C21—C20	−178.55 (17)
C7—O1—C8—C1	0.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.95	2.47	3.112 (3)	125
C15—H15B···Cg2ⁱⁱ	0.98	3.06	3.532 (3)	111

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁BrO₂S
M_r	417.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.7340 (4), 8.8290 (2), 13.0178 (3)
β (°)	105.197 (1)
V (Å³)	1856.05 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
Crystal size (mm)	0.25 × 0.23 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.561, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	17836, 4653, 3467
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.04
No. of reflections	4653
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.61

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.95	2.47	3.112 (3)	124.7
C15—H15B···Cg2ⁱⁱ	0.98	3.06	3.532 (3)	110.7

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, −y+1, −z+1.

Acknowledgements

This work was supported by 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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