7-Bromo-2-methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan

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

doi:10.1107/S160053680801177X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o944

doi:10.1107/S160053680801177X

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7-Bromo-2-methyl-1-(phenylsulfonyl)naphtho[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 15 April 2008; accepted 24 April 2008; online 30 April 2008)

The title compound, C₁₉H₁₃BrO₃S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking interactions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring molecules; the centroid–centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked molecules exhibit C—H⋯π, inter- and intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 7-bromonaphtho[2,1-b]furan compounds, see: Choi et al. (2006 , 2007 ).

Experimental

Crystal data

C₁₉H₁₃BrO₃S
M_r = 401.26
Triclinic, $[P \overline 1]$
a = 7.8583 (7) Å
b = 8.0025 (7) Å
c = 13.278 (1) Å
α = 107.429 (1)°
β = 93.678 (1)°
γ = 90.417 (2)°
V = 794.72 (12) Å³
Z = 2
Mo Kα radiation
μ = 2.73 mm⁻¹
T = 173 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.381, T_max = 0.571
6371 measured reflections
3084 independent reflections
2874 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.078
S = 1.17
3084 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1ⁱ	0.95	2.85	3.764 (3)	161
C4—H4⋯O2	0.95	2.44	3.226 (3)	140
C16—H16⋯O3ⁱⁱ	0.95	2.56	3.257 (3)	130
C19—H19A⋯O3	0.98	2.28	2.926 (3)	122
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z. Cg1 is the centroid of the C13–C18 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/S160053680801177X/jh2063sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801177X/jh2063Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 7-bromonaphtho[2,1-b]furan analogues, viz. 7-bromo-1-methylsulfanyl-2-phenylnaphtho[2,1-b]furan (Choi et al., 2006) and 7-bromo-2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (Choi et al., 2007). Herein we report the molecular and crystal structure of the title compound, 7-bromo-2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.012 Å from the least-squares plane defined by the thirteen constituent atoms. The phenyl ring (C13—C18) makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal packing (Fig. 2) is stabilized by two π—π stacking interactions within each stack of molecules; one between the brominated benzene ring (Cg2) and the central benzene ring (Cg3ⁱ) of an adjacent naphthofuran unit {distance; 3.981 (3) Å}, and a second between the brominated benzene ring (Cg2) and the central benzene ring (Cg3ⁱⁱⁱ) of an adjacent naphthofuran unit {distance; 3.889 (3) Å} (Cg2 and Cg3 are the centroids of the C3—C8 benzene ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between a brominated benzene H atom and the phenyl ring of the phenylsulfonyl substituent, with a C7—H7···Cg1ⁱ separation of 2.85 Å (Fig. 2 and Table 1; Cg1 is the centroid of the C13–18 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 7-bromonaphtho[2,1-b]furan compounds, see: Choi et al. (2006, 2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 320 mg, 1.43 mmol) was added in small portions to a stirred solution of 7-bromo-2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (240 mg, 0.65 mmol) in dichloromethane (20 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 (hexane-ethyl acetate, 2: 1 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 483–484 K; R_f = 0.68 (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 benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.99 (s, 3H), 7.43–7.55 (m, 3H), 7.59–7.71 (m, 3H), 7.95 (d, J = 8.40 Hz, 2H), 8.03 (s, 1H), 8.89 (s, J = 9.16 Hz, 1H); EI—MS 402 [M+2], 400 [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 code: (i) -x + 1, -y + 1, -z + 1; (ii) x - 1, y, z; (iii)-x + 2,-y + 1,-z + 1.]

7-Bromo-2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₃BrO₃S	Z = 2
M_r = 401.26	F(000) = 404
Triclinic, P1	D_x = 1.677 Mg m⁻³
Hall symbol: -p 1	Melting point = 483–484 K
a = 7.8583 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0025 (7) Å	Cell parameters from 4679 reflections
c = 13.278 (1) Å	θ = 2.6–28.2°
α = 107.429 (1)°	µ = 2.73 mm⁻¹
β = 93.678 (1)°	T = 173 K
γ = 90.417 (2)°	Block, colorless
V = 794.72 (12) Å³	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −9→9
T_min = 0.381, T_max = 0.571	l = −16→16
6371 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0451P)² + 0.2317P] where P = (F_o² + 2F_c²)/3
3084 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₃BrO₃S	γ = 90.417 (2)°
M_r = 401.26	V = 794.72 (12) Å³
Triclinic, P1	Z = 2
a = 7.8583 (7) Å	Mo Kα radiation
b = 8.0025 (7) Å	µ = 2.73 mm⁻¹
c = 13.278 (1) Å	T = 173 K
α = 107.429 (1)°	0.40 × 0.30 × 0.20 mm
β = 93.678 (1)°

Data collection top

Bruker SMART CCD diffractometer	3084 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2874 reflections with I > 2σ(I)
T_min = 0.381, T_max = 0.571	R_int = 0.016
6371 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.17	Δρ_max = 0.44 e Å⁻³
3084 reflections	Δρ_min = −0.35 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.56455 (3)	0.99911 (3)	0.696889 (17)	0.03340 (10)
S	0.82852 (6)	0.36218 (7)	0.16782 (4)	0.02320 (13)
O1	0.91789 (19)	0.0602 (2)	0.34760 (12)	0.0280 (3)
O2	0.9034 (2)	0.5362 (2)	0.20422 (12)	0.0303 (3)
O3	0.8886 (2)	0.2407 (2)	0.07411 (12)	0.0330 (4)
C1	0.8504 (3)	0.2648 (3)	0.26930 (16)	0.0228 (4)
C2	0.8191 (2)	0.3362 (3)	0.38127 (16)	0.0216 (4)
C3	0.7591 (2)	0.4950 (3)	0.45075 (16)	0.0212 (4)
C4	0.7119 (3)	0.6446 (3)	0.42140 (17)	0.0248 (4)
H4	0.7201	0.6435	0.3501	0.030*
C5	0.6545 (3)	0.7918 (3)	0.49309 (17)	0.0265 (4)
H5	0.6230	0.8911	0.4717	0.032*
C6	0.6432 (3)	0.7931 (3)	0.59824 (17)	0.0245 (4)
C7	0.6885 (3)	0.6539 (3)	0.63190 (17)	0.0256 (4)
H7	0.6804	0.6593	0.7039	0.031*
C8	0.7476 (3)	0.5013 (3)	0.55938 (16)	0.0229 (4)
C9	0.7963 (3)	0.3570 (3)	0.59591 (17)	0.0265 (4)
H9	0.7877	0.3654	0.6683	0.032*
C10	0.8549 (3)	0.2078 (3)	0.52932 (17)	0.0269 (5)
H10	0.8883	0.1115	0.5533	0.032*
C11	0.8634 (3)	0.2034 (3)	0.42350 (17)	0.0241 (4)
C12	0.9097 (3)	0.0997 (3)	0.25436 (18)	0.0265 (4)
C13	0.6075 (3)	0.3813 (3)	0.14109 (15)	0.0238 (4)
C14	0.5417 (3)	0.5444 (3)	0.14748 (17)	0.0294 (5)
H14	0.6117	0.6475	0.1741	0.035*
C15	0.3714 (3)	0.5544 (4)	0.11432 (19)	0.0372 (6)
H15	0.3246	0.6649	0.1178	0.045*
C16	0.2704 (3)	0.4035 (4)	0.07638 (19)	0.0404 (6)
H16	0.1546	0.4108	0.0531	0.049*
C17	0.3368 (3)	0.2418 (4)	0.0720 (2)	0.0395 (6)
H17	0.2657	0.1392	0.0473	0.047*
C18	0.5066 (3)	0.2292 (3)	0.10354 (17)	0.0310 (5)
H18	0.5533	0.1183	0.0995	0.037*
C19	0.9685 (3)	−0.0435 (3)	0.1644 (2)	0.0379 (6)
H19A	0.9215	−0.0285	0.0975	0.057*
H19B	0.9292	−0.1568	0.1697	0.057*
H19C	1.0933	−0.0395	0.1665	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04740 (16)	0.02425 (14)	0.02669 (14)	0.00861 (10)	0.00501 (10)	0.00413 (9)
S	0.0219 (2)	0.0270 (3)	0.0203 (2)	0.00089 (19)	0.00223 (19)	0.0063 (2)
O1	0.0319 (8)	0.0226 (8)	0.0282 (8)	0.0070 (6)	−0.0002 (6)	0.0061 (6)
O2	0.0302 (8)	0.0308 (8)	0.0310 (8)	−0.0054 (6)	0.0006 (6)	0.0116 (7)
O3	0.0325 (8)	0.0402 (10)	0.0247 (8)	0.0068 (7)	0.0088 (6)	0.0058 (7)
C1	0.0225 (10)	0.0231 (10)	0.0213 (10)	0.0004 (8)	−0.0009 (8)	0.0052 (8)
C2	0.0205 (9)	0.0222 (10)	0.0218 (10)	−0.0009 (8)	−0.0013 (8)	0.0065 (8)
C3	0.0191 (9)	0.0224 (10)	0.0218 (10)	−0.0016 (7)	−0.0017 (7)	0.0067 (8)
C4	0.0300 (11)	0.0240 (10)	0.0215 (10)	0.0013 (8)	0.0002 (8)	0.0086 (8)
C5	0.0331 (11)	0.0215 (10)	0.0254 (11)	0.0017 (8)	−0.0008 (9)	0.0083 (8)
C6	0.0278 (10)	0.0207 (10)	0.0227 (10)	0.0015 (8)	0.0013 (8)	0.0031 (8)
C7	0.0297 (11)	0.0265 (11)	0.0208 (10)	−0.0003 (9)	0.0024 (8)	0.0070 (8)
C8	0.0231 (10)	0.0233 (10)	0.0225 (10)	−0.0010 (8)	−0.0007 (8)	0.0075 (8)
C9	0.0291 (11)	0.0290 (11)	0.0239 (10)	0.0002 (9)	0.0005 (8)	0.0119 (9)
C10	0.0285 (11)	0.0255 (11)	0.0298 (11)	0.0030 (8)	−0.0018 (9)	0.0140 (9)
C11	0.0231 (10)	0.0202 (10)	0.0269 (11)	0.0016 (8)	−0.0017 (8)	0.0047 (8)
C12	0.0239 (10)	0.0276 (11)	0.0262 (10)	0.0025 (8)	−0.0014 (8)	0.0059 (9)
C13	0.0236 (10)	0.0322 (12)	0.0162 (9)	0.0012 (8)	0.0026 (8)	0.0080 (8)
C14	0.0333 (11)	0.0326 (12)	0.0209 (10)	0.0051 (9)	0.0016 (9)	0.0060 (9)
C15	0.0355 (12)	0.0495 (15)	0.0257 (11)	0.0166 (11)	0.0050 (9)	0.0091 (11)
C16	0.0230 (11)	0.0736 (19)	0.0263 (12)	0.0053 (11)	0.0022 (9)	0.0172 (12)
C17	0.0310 (12)	0.0577 (17)	0.0314 (12)	−0.0138 (11)	−0.0041 (10)	0.0174 (12)
C18	0.0332 (12)	0.0355 (13)	0.0261 (11)	−0.0044 (10)	−0.0010 (9)	0.0128 (10)
C19	0.0454 (14)	0.0306 (13)	0.0327 (13)	0.0122 (10)	0.0012 (11)	0.0022 (10)

Geometric parameters (Å, º) top

Br—C6	1.908 (2)	C8—C9	1.425 (3)
S—O2	1.4378 (16)	C9—C10	1.359 (3)
S—O3	1.4400 (16)	C9—H9	0.9500
S—C1	1.748 (2)	C10—C11	1.401 (3)
S—C13	1.767 (2)	C10—H10	0.9500
O1—C12	1.364 (3)	C12—C19	1.487 (3)
O1—C11	1.372 (3)	C13—C14	1.388 (3)
C1—C12	1.366 (3)	C13—C18	1.390 (3)
C1—C2	1.462 (3)	C14—C15	1.392 (3)
C2—C11	1.379 (3)	C14—H14	0.9500
C2—C3	1.432 (3)	C15—C16	1.383 (4)
C3—C4	1.410 (3)	C15—H15	0.9500
C3—C8	1.437 (3)	C16—C17	1.385 (4)
C4—C5	1.375 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.386 (3)
C5—C6	1.402 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.360 (3)	C19—H19A	0.9800
C7—C8	1.413 (3)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

O2—S—O3	118.45 (10)	C9—C10—C11	116.5 (2)
O2—S—C1	109.45 (10)	C9—C10—H10	121.8
O3—S—C1	107.55 (10)	C11—C10—H10	121.8
O2—S—C13	107.64 (10)	O1—C11—C2	111.29 (18)
O3—S—C13	106.29 (10)	O1—C11—C10	122.57 (19)
C1—S—C13	106.88 (10)	C2—C11—C10	126.1 (2)
C12—O1—C11	107.28 (17)	O1—C12—C1	110.04 (19)
C12—C1—C2	107.30 (19)	O1—C12—C19	113.40 (19)
C12—C1—S	122.87 (17)	C1—C12—C19	136.5 (2)
C2—C1—S	129.79 (16)	C14—C13—C18	121.4 (2)
C11—C2—C3	118.02 (18)	C14—C13—S	119.76 (17)
C11—C2—C1	104.08 (18)	C18—C13—S	118.51 (17)
C3—C2—C1	137.90 (19)	C13—C14—C15	119.0 (2)
C4—C3—C2	125.47 (19)	C13—C14—H14	120.5
C4—C3—C8	117.87 (19)	C15—C14—H14	120.5
C2—C3—C8	116.67 (19)	C16—C15—C14	120.0 (2)
C5—C4—C3	121.8 (2)	C16—C15—H15	120.0
C5—C4—H4	119.1	C14—C15—H15	120.0
C3—C4—H4	119.1	C15—C16—C17	120.5 (2)
C4—C5—C6	118.9 (2)	C15—C16—H16	119.7
C4—C5—H5	120.5	C17—C16—H16	119.7
C6—C5—H5	120.5	C16—C17—C18	120.3 (2)
C7—C6—C5	122.2 (2)	C16—C17—H17	119.9
C7—C6—Br	119.45 (16)	C18—C17—H17	119.9
C5—C6—Br	118.36 (16)	C17—C18—C13	118.9 (2)
C6—C7—C8	119.7 (2)	C17—C18—H18	120.6
C6—C7—H7	120.1	C13—C18—H18	120.6
C8—C7—H7	120.1	C12—C19—H19A	109.5
C7—C8—C9	119.17 (19)	C12—C19—H19B	109.5
C7—C8—C3	119.49 (19)	H19A—C19—H19B	109.5
C9—C8—C3	121.34 (19)	C12—C19—H19C	109.5
C10—C9—C8	121.4 (2)	H19A—C19—H19C	109.5
C10—C9—H9	119.3	H19B—C19—H19C	109.5
C8—C9—H9	119.3

O2—S—C1—C12	−131.89 (18)	C8—C9—C10—C11	−0.4 (3)
O3—S—C1—C12	−2.0 (2)	C12—O1—C11—C2	0.2 (2)
C13—S—C1—C12	111.81 (19)	C12—O1—C11—C10	179.8 (2)
O2—S—C1—C2	45.6 (2)	C3—C2—C11—O1	179.89 (17)
O3—S—C1—C2	175.49 (18)	C1—C2—C11—O1	0.0 (2)
C13—S—C1—C2	−70.7 (2)	C3—C2—C11—C10	0.3 (3)
C12—C1—C2—C11	−0.1 (2)	C1—C2—C11—C10	−179.6 (2)
S—C1—C2—C11	−177.90 (16)	C9—C10—C11—O1	−179.10 (19)
C12—C1—C2—C3	180.0 (2)	C9—C10—C11—C2	0.4 (3)
S—C1—C2—C3	2.2 (4)	C11—O1—C12—C1	−0.3 (2)
C11—C2—C3—C4	178.60 (19)	C11—O1—C12—C19	178.94 (19)
C1—C2—C3—C4	−1.5 (4)	C2—C1—C12—O1	0.2 (2)
C11—C2—C3—C8	−1.0 (3)	S—C1—C12—O1	178.21 (14)
C1—C2—C3—C8	178.9 (2)	C2—C1—C12—C19	−178.7 (3)
C2—C3—C4—C5	179.6 (2)	S—C1—C12—C19	−0.7 (4)
C8—C3—C4—C5	−0.8 (3)	O2—S—C13—C14	5.9 (2)
C3—C4—C5—C6	0.2 (3)	O3—S—C13—C14	−121.94 (17)
C4—C5—C6—C7	0.5 (3)	C1—S—C13—C14	123.41 (17)
C4—C5—C6—Br	179.61 (16)	O2—S—C13—C18	179.40 (16)
C5—C6—C7—C8	−0.6 (3)	O3—S—C13—C18	51.54 (19)
Br—C6—C7—C8	−179.70 (15)	C1—S—C13—C18	−63.10 (19)
C6—C7—C8—C9	179.35 (19)	C18—C13—C14—C15	−0.7 (3)
C6—C7—C8—C3	0.0 (3)	S—C13—C14—C15	172.57 (17)
C4—C3—C8—C7	0.7 (3)	C13—C14—C15—C16	0.4 (3)
C2—C3—C8—C7	−179.67 (18)	C14—C15—C16—C17	0.7 (4)
C4—C3—C8—C9	−178.63 (19)	C15—C16—C17—C18	−1.4 (4)
C2—C3—C8—C9	1.0 (3)	C16—C17—C18—C13	1.1 (4)
C7—C8—C9—C10	−179.6 (2)	C14—C13—C18—C17	0.0 (3)
C3—C8—C9—C10	−0.3 (3)	S—C13—C18—C17	−173.39 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1ⁱ	0.95	2.85	3.764 (3)	161
C4—H4···O2	0.95	2.44	3.226 (3)	140
C16—H16···O3ⁱⁱ	0.95	2.56	3.257 (3)	130
C19—H19A···O3	0.98	2.28	2.926 (3)	122

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrO₃S
M_r	401.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.8583 (7), 8.0025 (7), 13.278 (1)
α, β, γ (°)	107.429 (1), 93.678 (1), 90.417 (2)
V (Å³)	794.72 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.381, 0.571
No. of measured, independent and observed [I > 2σ(I)] reflections	6371, 3084, 2874
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.078, 1.17
No. of reflections	3084
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.35

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
C7—H7···Cg1ⁱ	0.95	2.85	3.764 (3)	161.2
C4—H4···O2	0.95	2.44	3.226 (3)	140.2
C16—H16···O3ⁱⁱ	0.95	2.56	3.257 (3)	130.3
C19—H19A···O3	0.98	2.28	2.926 (3)	122.4

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, 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. (2006). Acta Cryst. E62, o5876–o5877. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o4102. 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 5| May 2008| Page o944

doi:10.1107/S160053680801177X

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