7-Bromo-2-methyl-1-tosyl­naphtho[2,1-b]furan

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808015286

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1158

doi:10.1107/S1600536808015286

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7-Bromo-2-methyl-1-tosylnaphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b 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 16 May 2008; accepted 21 May 2008; online 24 May 2008)

The title compound, C₂₀H₁₅BrO₃S, was prepared by the oxidation of 7-bromo-2-methyl-1-(4-tolylsulfanyl)naphtho[2,1-b]furan with 3-chloroperoxybenzoic acid. The 4-tolyl ring makes a dihedral angle of 70.96 (6)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking interactions, with centroid–centroid distances of 3.672 (3) and 3.858 (3) Å between the central benzene and furan rings, and between the brominated benzene and central benzene rings of the naphthofuran system of neighbouring molecules, respectively. In addition, the stacked molecules exhibit C—H⋯π and inter- and intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan compounds, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₂₀H₁₅BrO₃S
M_r = 415.29
Monoclinic, P 2₁ /n
a = 14.026 (2) Å
b = 8.225 (1) Å
c = 15.185 (2) Å
β = 102.826 (2)°
V = 1708.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.54 mm⁻¹
T = 173 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.480, T_max = 0.608
10014 measured reflections
3704 independent reflections
3368 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.09
3704 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.95	2.57	3.485 (3)	163
C4—H4⋯O2	0.95	2.21	3.035 (2)	145
C15—H15⋯O3ⁱⁱ	0.95	2.42	3.303 (2)	155
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z. Cg1 is the centroid of the C13–C18 benzene ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536808015286/at2569sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015286/at2569Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan analogues, viz. 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Choi et al., 2008a) and 7-bromo-2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Choi et al., 2008b). Here we report the crystal structure of the title compound, 7-bromo-2-methyl-1-tosylnaphtho[2,1-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.01 Å from the least-squares plane defined by the thirteen constituent atoms. The 4-tolyl ring (C13-C18) makes a dihedral angle of 70.96 (6)° with the plane of the naphthofuran fragment. The molecular packing (Fig. 2) is stabilized by two different π—π interactions within each stack of molecule; one between the central benzene ring (Cg3) and the furan ring (Cg4ⁱⁱ) of the adjacent naphthofuran fragments {distance; 3.672 (3) Å}, and a second between the brominated benzene ring (Cg2) and the central benzene ring (Cg3ⁱⁱⁱ) of the adjacent naphthofuran fragments {distance; 3.858 (3) Å} (Fig. 2; Cg2, Cg3 and Cg4 are the centroids of the C3-C8 benzene, the C2/C3/C8/C9/C10/C11 benzene, and the O1/C12/C1/C2/C11 furan rings, respectively, symmetry code as in Fig. 2). The crystal packing is further stabilized by C—H···π interaction between a central benzene H atom of naphthofuran unit and the 4-tolyl ring of the tosyl substituent, with a C10—H10···Cg1ⁱ separation of 2.57 Å (Fig. 2 and Table 1; Cg1 is the centroid of the C13-C18 phenyl ring; symmetry code as in Fig. 2). Additionally, inter- and intramolecular C—H···O interactions in the structure were observed (Fig. 2 and Table 1; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan compounds, see: Choi et al. (2008a,b). Cg1 is the centroid of the C13–C18 benzene ring

Experimental top

3-Chloroperoxybenzoic acid (77%, 377 mg, 1.68 mmol) was added in small portions to a stirred solution of 7-bromo-2-methyl-1-(4-tolylsulfanyl)naphtho[2,1-b]furan (306 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 4 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (chloroform) to afford the title compound as a colourless solid [yield 79%, m.p. 480-481 K; R_f = 0.51 (chloroform)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in chloroform at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.35 (s, 3H), 2.99 (s, 3H), 7.27 (s, 2H), 7.59-7.68 (m, 3H), 7.83 (d, J = 8.08 Hz, 2H), 8.03 (s, 1H), 8.91 (s, J = 9.16 Hz, 1H); EI-MS 416 [M+2], 414 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. π···π, C—H···π and C—H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry codes: (i) x-1/2, -y+3/2, z-1/2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z+1; (iv) x, y+1, z; (v) x, y-1, z; (vi) x+1/2, -y+3/2, z+1/2.]

7-Bromo-2-methyl-1-tosylnaphtho[2,1-b]furan top

Crystal data top

C₂₀H₁₅BrO₃S	F(000) = 840
M_r = 415.29	D_x = 1.615 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 480–481 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.026 (2) Å	Cell parameters from 6484 reflections
b = 8.225 (1) Å	θ = 2.2–28.3°
c = 15.185 (2) Å	µ = 2.55 mm⁻¹
β = 102.826 (2)°	T = 173 K
V = 1708.1 (4) Å³	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3704 independent reflections
Radiation source: fine-focus sealed tube	3368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10 pixels mm^-1	θ_max = 27.0°, θ_min = 2.8°
ϕ and ω scans	h = −17→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −10→9
T_min = 0.480, T_max = 0.608	l = −19→19
10014 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0373P)² + 1.421P] where P = (F_o² + 2F_c²)/3
3704 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

C₂₀H₁₅BrO₃S	V = 1708.1 (4) Å³
M_r = 415.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.026 (2) Å	µ = 2.55 mm⁻¹
b = 8.225 (1) Å	T = 173 K
c = 15.185 (2) Å	0.30 × 0.30 × 0.20 mm
β = 102.826 (2)°

Data collection top

Bruker SMART CCD diffractometer	3704 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3368 reflections with I > 2σ(I)
T_min = 0.480, T_max = 0.608	R_int = 0.024
10014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.09	Δρ_max = 0.61 e Å⁻³
3704 reflections	Δρ_min = −1.04 e Å⁻³
228 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
Br	0.307602 (17)	1.04128 (3)	0.664085 (18)	0.04012 (10)
S	0.79201 (3)	0.59282 (6)	0.62949 (3)	0.01860 (11)
O1	0.64155 (11)	0.52776 (18)	0.38321 (9)	0.0264 (3)
O2	0.74469 (10)	0.61119 (18)	0.70363 (9)	0.0248 (3)
O3	0.85357 (11)	0.45249 (17)	0.62854 (11)	0.0276 (3)
C1	0.70375 (14)	0.5926 (2)	0.52785 (12)	0.0190 (4)
C2	0.60466 (14)	0.6593 (2)	0.50343 (12)	0.0184 (4)
C3	0.53912 (13)	0.7504 (2)	0.54485 (12)	0.0177 (4)
C4	0.56078 (14)	0.8095 (2)	0.63474 (13)	0.0214 (4)
H4	0.6233	0.7883	0.6723	0.026*
C5	0.49378 (15)	0.8966 (3)	0.66890 (14)	0.0245 (4)
H5	0.5102	0.9368	0.7290	0.029*
C6	0.40102 (15)	0.9256 (3)	0.61444 (15)	0.0249 (4)
C7	0.37592 (15)	0.8727 (3)	0.52738 (14)	0.0250 (4)
H7	0.3125	0.8947	0.4917	0.030*
C8	0.44413 (14)	0.7849 (2)	0.48995 (13)	0.0209 (4)
C9	0.41645 (15)	0.7306 (3)	0.39838 (14)	0.0266 (4)
H9	0.3529	0.7550	0.3638	0.032*
C10	0.47904 (16)	0.6451 (3)	0.35995 (13)	0.0264 (4)
H10	0.4611	0.6088	0.2991	0.032*
C11	0.57167 (15)	0.6128 (2)	0.41433 (13)	0.0219 (4)
C12	0.72149 (16)	0.5171 (2)	0.45281 (14)	0.0241 (4)
C13	0.86530 (13)	0.7660 (2)	0.62557 (12)	0.0181 (4)
C14	0.82844 (14)	0.9193 (2)	0.63701 (13)	0.0207 (4)
H14	0.7635	0.9315	0.6449	0.025*
C15	0.88778 (15)	1.0550 (2)	0.63683 (14)	0.0229 (4)
H15	0.8626	1.1602	0.6441	0.027*
C16	0.98325 (16)	1.0390 (2)	0.62625 (15)	0.0249 (4)
C17	1.01851 (17)	0.8839 (3)	0.61549 (19)	0.0361 (5)
H17	1.0837	0.8713	0.6083	0.043*
C18	0.96049 (16)	0.7473 (3)	0.61504 (17)	0.0309 (5)
H18	0.9856	0.6421	0.6076	0.037*
C19	0.80537 (19)	0.4294 (3)	0.43022 (17)	0.0359 (5)
H19A	0.8032	0.3148	0.4473	0.054*
H19B	0.8667	0.4782	0.4633	0.054*
H19C	0.8017	0.4374	0.3652	0.054*
C20	1.04846 (17)	1.1859 (3)	0.62979 (18)	0.0360 (5)
H20A	1.0081	1.2836	0.6153	0.054*
H20B	1.0896	1.1731	0.5858	0.054*
H20C	1.0901	1.1963	0.6906	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.03043 (14)	0.04477 (17)	0.04947 (17)	0.01043 (10)	0.01810 (11)	−0.00261 (11)
S	0.0176 (2)	0.0165 (2)	0.0206 (2)	0.00131 (16)	0.00179 (17)	0.00252 (17)
O1	0.0320 (8)	0.0272 (8)	0.0197 (7)	0.0013 (6)	0.0050 (6)	−0.0045 (6)
O2	0.0238 (7)	0.0306 (8)	0.0191 (7)	−0.0015 (6)	0.0029 (5)	0.0053 (6)
O3	0.0259 (8)	0.0169 (7)	0.0370 (8)	0.0048 (6)	0.0009 (6)	0.0022 (6)
C1	0.0194 (9)	0.0179 (9)	0.0191 (9)	0.0000 (7)	0.0030 (7)	−0.0002 (7)
C2	0.0204 (9)	0.0149 (8)	0.0183 (9)	−0.0019 (7)	0.0008 (7)	0.0014 (7)
C3	0.0180 (9)	0.0155 (8)	0.0187 (8)	−0.0011 (7)	0.0021 (7)	0.0026 (7)
C4	0.0187 (9)	0.0241 (10)	0.0201 (9)	−0.0014 (7)	0.0015 (7)	−0.0001 (7)
C5	0.0242 (10)	0.0264 (10)	0.0233 (10)	−0.0020 (8)	0.0061 (8)	−0.0034 (8)
C6	0.0219 (10)	0.0225 (10)	0.0324 (11)	0.0021 (8)	0.0107 (8)	0.0020 (8)
C7	0.0189 (9)	0.0252 (10)	0.0288 (10)	0.0024 (8)	0.0009 (8)	0.0058 (8)
C8	0.0206 (9)	0.0189 (9)	0.0211 (9)	−0.0016 (7)	0.0003 (7)	0.0040 (7)
C9	0.0244 (10)	0.0276 (10)	0.0227 (10)	−0.0006 (8)	−0.0056 (8)	0.0040 (8)
C10	0.0323 (11)	0.0268 (10)	0.0159 (9)	−0.0024 (8)	−0.0041 (8)	−0.0007 (8)
C11	0.0259 (10)	0.0193 (9)	0.0205 (9)	−0.0012 (8)	0.0048 (8)	−0.0005 (7)
C12	0.0263 (10)	0.0219 (10)	0.0243 (10)	−0.0001 (8)	0.0059 (8)	0.0005 (8)
C13	0.0176 (9)	0.0179 (9)	0.0184 (8)	0.0008 (7)	0.0029 (7)	−0.0005 (7)
C14	0.0157 (9)	0.0213 (9)	0.0245 (9)	0.0040 (7)	0.0029 (7)	0.0011 (7)
C15	0.0224 (10)	0.0177 (9)	0.0274 (10)	0.0041 (7)	0.0030 (8)	0.0005 (7)
C16	0.0248 (10)	0.0216 (10)	0.0295 (10)	−0.0020 (8)	0.0085 (8)	−0.0016 (8)
C17	0.0246 (11)	0.0275 (12)	0.0625 (16)	0.0002 (9)	0.0231 (11)	−0.0077 (11)
C18	0.0260 (11)	0.0201 (10)	0.0507 (13)	0.0019 (8)	0.0170 (10)	−0.0063 (9)
C19	0.0361 (13)	0.0377 (13)	0.0379 (12)	0.0065 (10)	0.0166 (10)	−0.0062 (10)
C20	0.0276 (11)	0.0271 (11)	0.0563 (15)	−0.0058 (9)	0.0158 (11)	−0.0028 (10)

Geometric parameters (Å, º) top

Br—C6	1.905 (2)	C9—H9	0.9500
S—O2	1.436 (2)	C10—C11	1.401 (3)
S—O3	1.443 (2)	C10—H10	0.9500
S—C1	1.751 (2)	C12—C19	1.483 (3)
S—C13	1.765 (2)	C13—C18	1.388 (3)
O1—C12	1.362 (3)	C13—C14	1.388 (3)
O1—C11	1.371 (3)	C14—C15	1.392 (3)
C1—C12	1.368 (3)	C14—H14	0.9500
C1—C2	1.463 (3)	C15—C16	1.390 (3)
C2—C11	1.383 (3)	C15—H15	0.9500
C2—C3	1.435 (3)	C16—C17	1.391 (3)
C3—C4	1.417 (3)	C16—C20	1.509 (3)
C3—C8	1.434 (3)	C17—C18	1.387 (3)
C4—C5	1.372 (3)	C17—H17	0.9500
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.399 (3)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.362 (3)	C19—H19C	0.9800
C7—C8	1.415 (3)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.430 (3)	C20—H20C	0.9800
C9—C10	1.354 (3)

O2—S—O3	118.26 (9)	O1—C11—C2	111.6 (2)
O2—S—C1	109.37 (9)	O1—C11—C10	122.3 (2)
O3—S—C1	107.33 (9)	C2—C11—C10	126.1 (2)
O2—S—C13	108.39 (9)	O1—C12—C1	110.3 (2)
O3—S—C13	106.92 (9)	O1—C12—C19	114.2 (2)
C1—S—C13	105.90 (9)	C1—C12—C19	135.5 (2)
C12—O1—C11	107.1 (2)	C18—C13—C14	120.7 (2)
C12—C1—C2	107.3 (2)	C18—C13—S	119.8 (2)
C12—C1—S	120.7 (2)	C14—C13—S	119.5 (1)
C2—C1—S	132.0 (2)	C13—C14—C15	119.2 (2)
C11—C2—C3	117.7 (2)	C13—C14—H14	120.4
C11—C2—C1	103.7 (2)	C15—C14—H14	120.4
C3—C2—C1	138.6 (2)	C16—C15—C14	121.1 (2)
C4—C3—C8	117.7 (2)	C16—C15—H15	119.5
C4—C3—C2	125.5 (2)	C14—C15—H15	119.5
C8—C3—C2	116.8 (2)	C15—C16—C17	118.5 (2)
C5—C4—C3	121.7 (2)	C15—C16—C20	120.8 (2)
C5—C4—H4	119.2	C17—C16—C20	120.7 (2)
C3—C4—H4	119.2	C18—C17—C16	121.4 (2)
C4—C5—C6	119.4 (2)	C18—C17—H17	119.3
C4—C5—H5	120.3	C16—C17—H17	119.3
C6—C5—H5	120.3	C17—C18—C13	119.2 (2)
C7—C6—C5	121.7 (2)	C17—C18—H18	120.4
C7—C6—Br	119.5 (2)	C13—C18—H18	120.4
C5—C6—Br	118.9 (2)	C12—C19—H19A	109.5
C6—C7—C8	120.1 (2)	C12—C19—H19B	109.5
C6—C7—H7	120.0	H19A—C19—H19B	109.5
C8—C7—H7	120.0	C12—C19—H19C	109.5
C7—C8—C9	119.2 (2)	H19A—C19—H19C	109.5
C7—C8—C3	119.4 (2)	H19B—C19—H19C	109.5
C9—C8—C3	121.4 (2)	C16—C20—H20A	109.5
C10—C9—C8	121.3 (2)	C16—C20—H20B	109.5
C10—C9—H9	119.4	H20A—C20—H20B	109.5
C8—C9—H9	119.4	C16—C20—H20C	109.5
C9—C10—C11	116.7 (2)	H20A—C20—H20C	109.5
C9—C10—H10	121.6	H20B—C20—H20C	109.5
C11—C10—H10	121.6

O2—S—C1—C12	−154.52 (16)	C12—O1—C11—C2	0.4 (2)
O3—S—C1—C12	−25.06 (19)	C12—O1—C11—C10	−179.39 (19)
C13—S—C1—C12	88.88 (18)	C3—C2—C11—O1	179.65 (16)
O2—S—C1—C2	23.9 (2)	C1—C2—C11—O1	−0.9 (2)
O3—S—C1—C2	153.39 (18)	C3—C2—C11—C10	−0.6 (3)
C13—S—C1—C2	−92.7 (2)	C1—C2—C11—C10	178.83 (19)
C12—C1—C2—C11	1.1 (2)	C9—C10—C11—O1	−179.86 (19)
S—C1—C2—C11	−177.49 (16)	C9—C10—C11—C2	0.4 (3)
C12—C1—C2—C3	−179.6 (2)	C11—O1—C12—C1	0.4 (2)
S—C1—C2—C3	1.8 (4)	C11—O1—C12—C19	−179.30 (18)
C11—C2—C3—C4	−179.21 (18)	C2—C1—C12—O1	−1.0 (2)
C1—C2—C3—C4	1.6 (4)	S—C1—C12—O1	177.83 (14)
C11—C2—C3—C8	0.3 (3)	C2—C1—C12—C19	178.7 (2)
C1—C2—C3—C8	−178.8 (2)	S—C1—C12—C19	−2.5 (4)
C8—C3—C4—C5	0.1 (3)	O2—S—C13—C18	133.70 (17)
C2—C3—C4—C5	179.65 (19)	O3—S—C13—C18	5.2 (2)
C3—C4—C5—C6	1.2 (3)	C1—S—C13—C18	−109.04 (18)
C4—C5—C6—C7	−1.5 (3)	O2—S—C13—C14	−43.50 (17)
C4—C5—C6—Br	178.18 (16)	O3—S—C13—C14	−172.00 (15)
C5—C6—C7—C8	0.4 (3)	C1—S—C13—C14	73.77 (17)
Br—C6—C7—C8	−179.22 (15)	C18—C13—C14—C15	0.7 (3)
C6—C7—C8—C9	−179.87 (19)	S—C13—C14—C15	177.89 (15)
C6—C7—C8—C3	0.9 (3)	C13—C14—C15—C16	−0.6 (3)
C4—C3—C8—C7	−1.1 (3)	C14—C15—C16—C17	0.2 (3)
C2—C3—C8—C7	179.28 (17)	C14—C15—C16—C20	−177.6 (2)
C4—C3—C8—C9	179.64 (18)	C15—C16—C17—C18	0.1 (4)
C2—C3—C8—C9	0.1 (3)	C20—C16—C17—C18	177.9 (2)
C7—C8—C9—C10	−179.5 (2)	C16—C17—C18—C13	0.0 (4)
C3—C8—C9—C10	−0.2 (3)	C14—C13—C18—C17	−0.4 (3)
C8—C9—C10—C11	0.0 (3)	S—C13—C18—C17	−177.58 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.95	2.57	3.485 (3)	163
C4—H4···O2	0.95	2.21	3.035 (2)	145
C15—H15···O3ⁱⁱ	0.95	2.42	3.303 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅BrO₃S
M_r	415.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	14.026 (2), 8.225 (1), 15.185 (2)
β (°)	102.826 (2)
V (Å³)	1708.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.55
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.480, 0.608
No. of measured, independent and observed [I > 2σ(I)] reflections	10014, 3704, 3368
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.09
No. of reflections	3704
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −1.04

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.95	2.57	3.485 (3)	163.0
C4—H4···O2	0.95	2.21	3.035 (2)	144.5
C15—H15···O3ⁱⁱ	0.95	2.42	3.303 (2)	155.2

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o944. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1158

doi:10.1107/S1600536808015286

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