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

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

doi:10.1107/S1600536812001791

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o480

doi:10.1107/S1600536812001791

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3-(4-Bromophenylsulfonyl)-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 26 December 2011; accepted 15 January 2012; online 21 January 2012)

In the title compound, C₂₁H₂₁BrO₃S, the cyclohexyl ring adopts a chair conformation. The 4-bromophenyl ring makes a dihedral angle of 80.88 (6)° with the mean plane of the benzofuran fragment. An intramolecular C—H⋯O hydrogen bond is formed between an O atom of the sulfonyl group and one H atom of the aromatic ring such that a five-membered ring is formed. The crystal packing is stabilized by an intermolecular C—H⋯O hydrogen bond, which links the molecules into chains with graph-set notation C(6) running parallel to the c axis, and π–π stacking interactions [centroid–centroid distance = 3.6129 (12) 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. (2011 ); Seo et al. (2011 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₂₁BrO₃S
M_r = 433.35
Monoclinic, P 2₁ /c
a = 16.8264 (3) Å
b = 8.7627 (1) Å
c = 13.3545 (2) Å
β = 104.248 (1)°
V = 1908.48 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.28 mm⁻¹
T = 173 K
0.31 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.543, T_max = 0.686
18100 measured reflections
4739 independent reflections
3566 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.03
4739 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2	0.98	2.40	3.125 (3)	131
C18—H18⋯O3ⁱ	0.95	2.48	3.120 (3)	125
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 PLATON (Spek,2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001791/bx2395sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001791/bx2395Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001791/bx2395Isup3.cml

checkCIF report

Comment top

Benzofuran derivatives have drawn much interest in view of 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-2-methyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfonyl) (Choi et al., 2011) or 3-phenylsulfonyl (Seo et al., 2011) 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form as shown by the Cremer & Pople (1975) puckering parameters: Q = 0.560 (3)Å, θ = 1.8 (3)°, and ϕ = 187 (39) °]. The dihedral angle formed by the 4-bromophenyl ring and the mean plane of the benzofurn fragment is 80.88 (6)°. An intramolecular C–H···O hydrogen bond is formed between an O atom of the sulfonyl group and one H atom of the aromatic ring such that a five-membered ring is formed. The crystal packing is stabilized by an intermolecular C—H···O hydrogen bond, which links the molecules into chains with graph-set notation C(6) (Bernstein et al., 1995) running parallel to c axis, Fig.2, Table 1 and π–π stacking interactions, Fig.3 , Table2.

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. (2011); Seo et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

77% 3-chloroperoxybenzoic acid (448 mg, 2 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-cyclohexyl-2-methyl-1-benzofuran (361 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 67%, m.p. 459–460 K; R_f = 0.51 (benzene)]. 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, 1997) and PLATON (Spek,2009); 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 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 + 1/2, z - 1/2; (iii) x, - y + 1/2, z + 1/2.]
	Fig. 3. A view of the π–π interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (ii) - x, - y + 1, - z + 1.]

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

Crystal data top

C₂₁H₂₁BrO₃S	F(000) = 888
M_r = 433.35	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5934 reflections
a = 16.8264 (3) Å	θ = 2.6–27.2°
b = 8.7627 (1) Å	µ = 2.28 mm⁻¹
c = 13.3545 (2) Å	T = 173 K
β = 104.248 (1)°	Block, colourless
V = 1908.48 (5) Å³	0.31 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4739 independent reflections
Radiation source: rotating anode	3566 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.3°
ϕ and ω scans	h = −18→22
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→7
T_min = 0.543, T_max = 0.686	l = −17→17
18100 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0533P)² + 0.5992P] where P = (F_o² + 2F_c²)/3
4739 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₂₁H₂₁BrO₃S	V = 1908.48 (5) Å³
M_r = 433.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8264 (3) Å	µ = 2.28 mm⁻¹
b = 8.7627 (1) Å	T = 173 K
c = 13.3545 (2) Å	0.31 × 0.19 × 0.18 mm
β = 104.248 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4739 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3566 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.686	R_int = 0.031
18100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.60 e Å⁻³
4739 reflections	Δρ_min = −0.71 e Å⁻³
236 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	0.472627 (17)	0.39062 (4)	0.30549 (2)	0.05789 (12)
S1	0.15069 (3)	0.28324 (5)	0.47083 (4)	0.02514 (12)
O1	0.04011 (9)	0.67903 (17)	0.41683 (12)	0.0338 (4)
O2	0.09589 (10)	0.18906 (17)	0.39712 (12)	0.0352 (4)
O3	0.17627 (9)	0.23523 (16)	0.57671 (11)	0.0311 (3)
C1	0.11029 (12)	0.4652 (2)	0.46944 (15)	0.0250 (4)
C2	0.13778 (12)	0.5779 (2)	0.54926 (16)	0.0250 (4)
C3	0.19440 (13)	0.5830 (2)	0.64531 (17)	0.0263 (4)
H3	0.2256	0.4951	0.6720	0.032*
C4	0.20449 (12)	0.7184 (2)	0.70136 (17)	0.0288 (5)
C5	0.15718 (14)	0.8459 (2)	0.6599 (2)	0.0368 (5)
H5	0.1644	0.9381	0.6985	0.044*
C6	0.10060 (14)	0.8430 (2)	0.5654 (2)	0.0378 (5)
H6	0.0691	0.9304	0.5385	0.045*
C7	0.09228 (13)	0.7077 (2)	0.51260 (17)	0.0302 (5)
C8	0.05259 (12)	0.5303 (2)	0.39189 (17)	0.0299 (5)
C9	0.26505 (13)	0.7263 (2)	0.80598 (17)	0.0308 (5)
H9	0.2646	0.8333	0.8320	0.037*
C10	0.35212 (14)	0.6904 (3)	0.79958 (18)	0.0404 (6)
H10A	0.3693	0.7654	0.7536	0.049*
H10B	0.3534	0.5878	0.7690	0.049*
C11	0.41288 (16)	0.6951 (3)	0.9066 (2)	0.0471 (6)
H11A	0.4680	0.6648	0.8998	0.057*
H11B	0.4166	0.8008	0.9335	0.057*
C12	0.38692 (19)	0.5901 (3)	0.9823 (2)	0.0506 (7)
H12A	0.4252	0.6013	1.0512	0.061*
H12B	0.3895	0.4830	0.9597	0.061*
C13	0.30039 (19)	0.6264 (4)	0.9898 (2)	0.0544 (7)
H13A	0.2994	0.7293	1.0200	0.065*
H13B	0.2835	0.5519	1.0362	0.065*
C14	0.23995 (16)	0.6211 (3)	0.88381 (19)	0.0438 (6)
H14A	0.1849	0.6511	0.8910	0.053*
H14B	0.2363	0.5151	0.8574	0.053*
C15	0.00326 (14)	0.4780 (3)	0.29081 (17)	0.0382 (5)
H15A	0.0170	0.3717	0.2798	0.057*
H15B	0.0151	0.5421	0.2361	0.057*
H15C	−0.0551	0.4855	0.2894	0.057*
C16	0.24026 (13)	0.3119 (2)	0.42616 (15)	0.0249 (4)
C17	0.23543 (13)	0.3041 (2)	0.32088 (15)	0.0282 (4)
H17	0.1846	0.2815	0.2737	0.034*
C18	0.30421 (15)	0.3291 (3)	0.28488 (17)	0.0338 (5)
H18	0.3012	0.3253	0.2130	0.041*
C19	0.37760 (14)	0.3597 (3)	0.35501 (19)	0.0336 (5)
C20	0.38350 (14)	0.3691 (3)	0.45991 (18)	0.0355 (5)
H20	0.4346	0.3913	0.5067	0.043*
C21	0.31415 (13)	0.3457 (3)	0.49569 (16)	0.0305 (5)
H21	0.3170	0.3527	0.5675	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03863 (18)	0.0885 (3)	0.0517 (2)	0.00045 (13)	0.02099 (14)	−0.00445 (14)
S1	0.0269 (3)	0.0250 (2)	0.0201 (2)	−0.0028 (2)	−0.0007 (2)	0.00023 (19)
O1	0.0247 (8)	0.0351 (8)	0.0382 (9)	0.0053 (6)	0.0014 (7)	0.0107 (7)
O2	0.0351 (9)	0.0351 (8)	0.0300 (8)	−0.0102 (7)	−0.0024 (7)	−0.0058 (7)
O3	0.0376 (8)	0.0300 (7)	0.0230 (8)	−0.0007 (6)	0.0019 (7)	0.0045 (6)
C1	0.0236 (10)	0.0275 (10)	0.0227 (10)	0.0008 (8)	0.0034 (8)	0.0042 (8)
C2	0.0218 (10)	0.0235 (9)	0.0308 (11)	0.0016 (7)	0.0087 (9)	0.0036 (8)
C3	0.0246 (11)	0.0238 (9)	0.0296 (11)	0.0018 (8)	0.0049 (9)	0.0003 (8)
C4	0.0234 (10)	0.0266 (10)	0.0379 (12)	−0.0027 (8)	0.0105 (9)	−0.0040 (9)
C5	0.0319 (12)	0.0247 (10)	0.0546 (15)	0.0010 (9)	0.0123 (12)	−0.0066 (10)
C6	0.0288 (12)	0.0266 (11)	0.0576 (16)	0.0083 (9)	0.0096 (12)	0.0052 (11)
C7	0.0211 (10)	0.0313 (11)	0.0377 (12)	0.0027 (8)	0.0065 (9)	0.0084 (9)
C8	0.0223 (10)	0.0365 (11)	0.0307 (11)	0.0000 (9)	0.0063 (9)	0.0084 (9)
C9	0.0303 (11)	0.0265 (10)	0.0347 (12)	−0.0040 (9)	0.0064 (10)	−0.0096 (9)
C10	0.0258 (12)	0.0608 (16)	0.0346 (13)	−0.0044 (11)	0.0075 (10)	−0.0037 (11)
C11	0.0308 (13)	0.0652 (18)	0.0415 (15)	−0.0023 (12)	0.0018 (11)	−0.0119 (13)
C12	0.0581 (18)	0.0480 (15)	0.0381 (15)	0.0051 (13)	−0.0026 (13)	−0.0055 (12)
C13	0.064 (2)	0.0674 (18)	0.0335 (14)	−0.0088 (15)	0.0159 (14)	−0.0057 (12)
C14	0.0414 (14)	0.0578 (16)	0.0359 (14)	−0.0108 (11)	0.0168 (12)	−0.0085 (11)
C15	0.0276 (11)	0.0559 (15)	0.0262 (11)	−0.0029 (11)	−0.0026 (9)	0.0109 (11)
C16	0.0267 (10)	0.0228 (9)	0.0228 (10)	0.0016 (8)	0.0013 (8)	−0.0004 (8)
C17	0.0287 (11)	0.0316 (11)	0.0191 (10)	0.0009 (9)	−0.0041 (9)	−0.0041 (8)
C18	0.0415 (13)	0.0364 (11)	0.0228 (11)	0.0034 (10)	0.0064 (10)	−0.0033 (9)
C19	0.0289 (12)	0.0365 (11)	0.0363 (13)	0.0022 (9)	0.0095 (10)	−0.0014 (10)
C20	0.0270 (12)	0.0450 (13)	0.0300 (12)	0.0003 (10)	−0.0018 (10)	−0.0028 (10)
C21	0.0314 (12)	0.0366 (11)	0.0195 (10)	0.0009 (9)	−0.0015 (9)	−0.0001 (9)

Geometric parameters (Å, º) top

Br1—C19	1.894 (2)	C10—H10B	0.9900
S1—O2	1.4330 (15)	C11—C12	1.509 (4)
S1—O3	1.4360 (15)	C11—H11A	0.9900
S1—C1	1.731 (2)	C11—H11B	0.9900
S1—C16	1.770 (2)	C12—C13	1.517 (4)
O1—C8	1.374 (3)	C12—H12A	0.9900
O1—C7	1.385 (3)	C12—H12B	0.9900
C1—C8	1.359 (3)	C13—C14	1.526 (4)
C1—C2	1.444 (3)	C13—H13A	0.9900
C2—C7	1.391 (3)	C13—H13B	0.9900
C2—C3	1.398 (3)	C14—H14A	0.9900
C3—C4	1.391 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.405 (3)	C15—H15B	0.9800
C4—C9	1.515 (3)	C15—H15C	0.9800
C5—C6	1.381 (3)	C16—C21	1.388 (3)
C5—H5	0.9500	C16—C17	1.390 (3)
C6—C7	1.369 (3)	C17—C18	1.376 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.473 (3)	C18—C19	1.380 (3)
C9—C10	1.521 (3)	C18—H18	0.9500
C9—C14	1.525 (3)	C19—C20	1.382 (3)
C9—H9	1.0000	C20—C21	1.381 (3)
C10—C11	1.540 (3)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500

O2—S1—O3	119.59 (9)	C12—C11—H11B	109.3
O2—S1—C1	109.78 (10)	C10—C11—H11B	109.3
O3—S1—C1	107.58 (9)	H11A—C11—H11B	107.9
O2—S1—C16	107.91 (10)	C11—C12—C13	110.9 (2)
O3—S1—C16	107.43 (9)	C11—C12—H12A	109.5
C1—S1—C16	103.33 (9)	C13—C12—H12A	109.5
C8—O1—C7	107.22 (15)	C11—C12—H12B	109.5
C8—C1—C2	108.29 (18)	C13—C12—H12B	109.5
C8—C1—S1	126.89 (17)	H12A—C12—H12B	108.0
C2—C1—S1	124.67 (15)	C12—C13—C14	111.3 (2)
C7—C2—C3	119.29 (19)	C12—C13—H13A	109.4
C7—C2—C1	104.56 (18)	C14—C13—H13A	109.4
C3—C2—C1	136.16 (18)	C12—C13—H13B	109.4
C4—C3—C2	119.09 (19)	C14—C13—H13B	109.4
C4—C3—H3	120.5	H13A—C13—H13B	108.0
C2—C3—H3	120.5	C13—C14—C9	112.3 (2)
C3—C4—C5	119.0 (2)	C13—C14—H14A	109.1
C3—C4—C9	120.07 (18)	C9—C14—H14A	109.1
C5—C4—C9	120.93 (19)	C13—C14—H14B	109.1
C6—C5—C4	122.8 (2)	C9—C14—H14B	109.1
C6—C5—H5	118.6	H14A—C14—H14B	107.9
C4—C5—H5	118.6	C8—C15—H15A	109.5
C7—C6—C5	116.5 (2)	C8—C15—H15B	109.5
C7—C6—H6	121.7	H15A—C15—H15B	109.5
C5—C6—H6	121.7	C8—C15—H15C	109.5
C6—C7—O1	126.46 (19)	H15A—C15—H15C	109.5
C6—C7—C2	123.3 (2)	H15B—C15—H15C	109.5
O1—C7—C2	110.23 (18)	C21—C16—C17	120.5 (2)
C1—C8—O1	109.70 (18)	C21—C16—S1	120.10 (16)
C1—C8—C15	134.7 (2)	C17—C16—S1	119.43 (16)
O1—C8—C15	115.61 (18)	C18—C17—C16	120.06 (19)
C4—C9—C10	112.16 (18)	C18—C17—H17	120.0
C4—C9—C14	111.38 (18)	C16—C17—H17	120.0
C10—C9—C14	110.2 (2)	C17—C18—C19	118.9 (2)
C4—C9—H9	107.6	C17—C18—H18	120.6
C10—C9—H9	107.6	C19—C18—H18	120.6
C14—C9—H9	107.6	C18—C19—C20	121.9 (2)
C9—C10—C11	111.8 (2)	C18—C19—Br1	118.82 (18)
C9—C10—H10A	109.3	C20—C19—Br1	119.28 (18)
C11—C10—H10A	109.3	C21—C20—C19	119.1 (2)
C9—C10—H10B	109.3	C21—C20—H20	120.5
C11—C10—H10B	109.3	C19—C20—H20	120.5
H10A—C10—H10B	107.9	C20—C21—C16	119.6 (2)
C12—C11—C10	111.7 (2)	C20—C21—H21	120.2
C12—C11—H11A	109.3	C16—C21—H21	120.2
C10—C11—H11A	109.3

O2—S1—C1—C8	−21.0 (2)	C7—O1—C8—C15	−178.98 (18)
O3—S1—C1—C8	−152.62 (18)	C3—C4—C9—C10	59.7 (3)
C16—S1—C1—C8	93.9 (2)	C5—C4—C9—C10	−121.0 (2)
O2—S1—C1—C2	164.01 (17)	C3—C4—C9—C14	−64.3 (3)
O3—S1—C1—C2	32.4 (2)	C5—C4—C9—C14	115.0 (2)
C16—S1—C1—C2	−81.09 (18)	C4—C9—C10—C11	−178.6 (2)
C8—C1—C2—C7	0.4 (2)	C14—C9—C10—C11	−53.9 (3)
S1—C1—C2—C7	176.20 (16)	C9—C10—C11—C12	55.4 (3)
C8—C1—C2—C3	−179.7 (2)	C10—C11—C12—C13	−55.3 (3)
S1—C1—C2—C3	−3.9 (4)	C11—C12—C13—C14	55.3 (3)
C7—C2—C3—C4	−0.7 (3)	C12—C13—C14—C9	−55.6 (3)
C1—C2—C3—C4	179.4 (2)	C4—C9—C14—C13	179.6 (2)
C2—C3—C4—C5	0.3 (3)	C10—C9—C14—C13	54.5 (3)
C2—C3—C4—C9	179.58 (18)	O2—S1—C16—C21	−155.16 (16)
C3—C4—C5—C6	0.1 (3)	O3—S1—C16—C21	−24.96 (19)
C9—C4—C5—C6	−179.2 (2)	C1—S1—C16—C21	88.60 (18)
C4—C5—C6—C7	0.0 (4)	O2—S1—C16—C17	26.52 (19)
C5—C6—C7—O1	−179.5 (2)	O3—S1—C16—C17	156.72 (16)
C5—C6—C7—C2	−0.5 (3)	C1—S1—C16—C17	−89.71 (17)
C8—O1—C7—C6	178.8 (2)	C21—C16—C17—C18	0.4 (3)
C8—O1—C7—C2	−0.3 (2)	S1—C16—C17—C18	178.71 (16)
C3—C2—C7—C6	0.9 (3)	C16—C17—C18—C19	0.8 (3)
C1—C2—C7—C6	−179.2 (2)	C17—C18—C19—C20	−1.4 (3)
C3—C2—C7—O1	−179.99 (18)	C17—C18—C19—Br1	178.92 (16)
C1—C2—C7—O1	−0.1 (2)	C18—C19—C20—C21	0.6 (3)
C2—C1—C8—O1	−0.6 (2)	Br1—C19—C20—C21	−179.67 (17)
S1—C1—C8—O1	−176.28 (15)	C19—C20—C21—C16	0.6 (3)
C2—C1—C8—C15	178.8 (2)	C17—C16—C21—C20	−1.2 (3)
S1—C1—C8—C15	3.1 (4)	S1—C16—C21—C20	−179.45 (17)
C7—O1—C8—C1	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.40	3.125 (3)	131
C18—H18···O3ⁱ	0.95	2.48	3.120 (3)	125

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁BrO₃S
M_r	433.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.8264 (3), 8.7627 (1), 13.3545 (2)
β (°)	104.248 (1)
V (Å³)	1908.48 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.28
Crystal size (mm)	0.31 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.543, 0.686
No. of measured, independent and observed [I > 2σ(I)] reflections	18100, 4739, 3566
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.03
No. of reflections	4739
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.71

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.40	3.125 (3)	131
C18—H18···O3ⁱ	0.95	2.48	3.120 (3)	125

Symmetry code: (i) x, −y+1/2, z−1/2.

π-π stacking interaction in (I) top

Cg1 is the centroid of the O1/C7/C2/C1/C8 ring, ϕ is the dihedral angle (°) between the planes of the rings, d is the distance (Å) between the ring centroids and Δ is the displacement (Å) of the centroid of ring 2 relative to the intersection point of the normal to the centroid of ring 1 and the least-squares plane of ring 2

Ring 1	Ring 2	ϕ	d	Δ
O1/C7/C2/C1/C8	(O1/C7/C2/C1/C8)ⁱⁱ	0.0	3.6129 (12)	0.938

Symmetry code: (ii)-x,1-y,1-z

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

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1496. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar