Isoamyl 2-(5-bromo-3-methyl­sulfin­yl-1-benzofuran-2-­yl)acetate

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

doi:10.1107/S1600536809020613

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1498

doi:10.1107/S1600536809020613

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Isoamyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

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 28 May 2009; accepted 30 May 2009; online 6 June 2009)

In the title compound, C₁₆H₁₉BrO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure exhibits aromatic π–π interactions between the benzene rings of adjacent molecules [centroid–centroid distance = 3.643 (2) Å] and nonclassical C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2009a ,b ). For the biological and pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ); Ward (1997 ).

Experimental

Crystal data

C₁₆H₁₉BrO₄S
M_r = 387.28
Triclinic, $[P \overline 1]$
a = 8.3704 (4) Å
b = 10.2956 (6) Å
c = 10.524 (1) Å
α = 99.977 (1)°
β = 105.230 (1)°
γ = 100.681 (1)°
V = 836.04 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 173 K
0.60 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan SADABS (Sheldrick, 1999 ) T_min = 0.302, T_max = 0.769
7179 measured reflections
3579 independent reflections
3304 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.04
3579 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.56	3.437 (2)	157
C5—H5⋯O3ⁱⁱ	0.93	2.51	3.383 (2)	157
C9—H9A⋯O4ⁱⁱⁱ	0.97	2.26	3.192 (2)	162
C9—H9B⋯O1^iv	0.97	2.61	3.541 (2)	160
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y, -z+1.

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 datablock I. DOI: 10.1107/S1600536809020613/cv2569sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020613/cv2569Isup2.hkl

checkCIF report

Comment top

The benzofuran ring system has attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Ward, 1997). This work is related to our communications on the synthesis and structures of alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. butyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2009a) and propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2009b). Here we report the crystal structure of the title compound, isoamyl 2-(5-bromo-3-methyllsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π···π interactions between the benzene rings from the adjacent molecules. The Cg···Cgⁱⁱ distance of 3.643 (2) Å (Cg is the centroid of C2-C7 benzene ring. symmetry code as in Fig. 2). The molecular packing is further stabilized by four different types of non-calssical C–H···O hydrogen bonds; the first between a benzene H atom and the S=O unit, the second between a benzene H atom and the C═O unit, the third between an H atom of the methylene group bonded to the carboxylate C atom and the S═O unit, the fourth between an H atom of the methylene group bonded to the carboxylate C atom and the furan O atom, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2009a,b). For the biological and pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Ward (1997).

Experimental top

The 77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of isoamyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (371 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, 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,1:2 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 387-388 K; Rf = 0.61 (hexane-ethyl acetate, 1;2 v/v )]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in ethyl acetate at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.91 (d, J = 6.6 Hz, 6H), 1.51-1.57 (m, 1H), 1.62-1.69 (m, 2H), 3.07 (s, 3H), 4.03 (s, 2H), 4.18 (t, J = 6.96 Hz, 2H), 7.39 (d, J = 8.8 Hz, 1H), 7.49 (dd, J = 8.8 Hz and J = 2.2 Hz, 1H), 8.09 (d, J = 1.84 Hz, 1H); EI-MS 388 [M+2], 386 [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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The π···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 + 1; (iii) -x + 2, -y + 1, -z + 1; (iv) -x + 2, -y, -z + 1.]

Isoamyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₆H₁₉BrO₄S	Z = 2
M_r = 387.28	F(000) = 396
Triclinic, P1	D_x = 1.538 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3704 (4) Å	Cell parameters from 5367 reflections
b = 10.2956 (6) Å	θ = 2.1–28.2°
c = 10.524 (1) Å	µ = 2.60 mm⁻¹
α = 99.977 (1)°	T = 173 K
β = 105.230 (1)°	Block, colourless
γ = 100.681 (1)°	0.60 × 0.40 × 0.10 mm
V = 836.04 (10) Å³

Data collection top

Bruker SMART CCD diffractometer	3579 independent reflections
Radiation source: fine-focus sealed tube	3304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.6°
ϕ– and ω–scans	h = −10→10
Absorption correction: multi-scan SADABS (Sheldrick, 1999)	k = −13→13
T_min = 0.302, T_max = 0.769	l = −13→13
7179 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)] = 0.027	Hydrogen site location: difference Fourier map
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0362P)² + 0.2834P] where P = (F_o² + 2F_c²)/3
3579 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₉BrO₄S	γ = 100.681 (1)°
M_r = 387.28	V = 836.04 (10) Å³
Triclinic, P1	Z = 2
a = 8.3704 (4) Å	Mo Kα radiation
b = 10.2956 (6) Å	µ = 2.60 mm⁻¹
c = 10.524 (1) Å	T = 173 K
α = 99.977 (1)°	0.60 × 0.40 × 0.10 mm
β = 105.230 (1)°

Data collection top

Bruker SMART CCD diffractometer	3579 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1999)	3304 reflections with I > 2σ(I)
T_min = 0.302, T_max = 0.769	R_int = 0.024
7179 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
3579 reflections	Δρ_min = −0.59 e Å⁻³
202 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	0.09369 (2)	0.119447 (19)	0.255278 (19)	0.03270 (8)
S	0.83063 (5)	0.46517 (4)	0.59651 (5)	0.02459 (11)
O1	0.81346 (14)	0.07754 (11)	0.46466 (12)	0.0215 (2)
O2	1.24425 (15)	0.21464 (13)	0.82349 (12)	0.0254 (3)
O3	1.00246 (16)	0.27962 (14)	0.82283 (14)	0.0330 (3)
O4	0.73464 (19)	0.52767 (13)	0.49185 (15)	0.0335 (3)
C1	0.7776 (2)	0.28864 (16)	0.52535 (17)	0.0202 (3)
C2	0.6130 (2)	0.20245 (16)	0.44185 (16)	0.0195 (3)
C3	0.4469 (2)	0.21889 (17)	0.39790 (17)	0.0222 (3)
H3	0.4214	0.3025	0.4195	0.027*
C4	0.3225 (2)	0.10378 (18)	0.32050 (17)	0.0230 (3)
C5	0.3554 (2)	−0.02394 (17)	0.28541 (18)	0.0244 (3)
H5	0.2667	−0.0978	0.2327	0.029*
C6	0.5200 (2)	−0.04033 (17)	0.32914 (18)	0.0237 (3)
H6	0.5453	−0.1240	0.3069	0.028*
C7	0.6445 (2)	0.07386 (16)	0.40746 (17)	0.0202 (3)
C8	0.8916 (2)	0.20979 (16)	0.53584 (17)	0.0203 (3)
C9	1.0744 (2)	0.23516 (17)	0.61405 (18)	0.0225 (3)
H9A	1.1371	0.3191	0.6023	0.027*
H9B	1.1206	0.1619	0.5790	0.027*
C10	1.0990 (2)	0.24522 (16)	0.76378 (18)	0.0226 (3)
C11	1.2757 (2)	0.2174 (2)	0.96764 (19)	0.0344 (4)
H11A	1.1845	0.1527	0.9803	0.041*
H11B	1.2802	0.3073	1.0174	0.041*
C12	1.4438 (2)	0.18093 (19)	1.01854 (19)	0.0301 (4)
H12A	1.4417	0.0973	0.9584	0.036*
H12B	1.4531	0.1625	1.1072	0.036*
C13	1.6038 (2)	0.28719 (19)	1.03000 (19)	0.0290 (4)
H13	1.5949	0.3064	0.9407	0.035*
C14	1.6262 (3)	0.4197 (2)	1.1307 (2)	0.0483 (6)
H14A	1.5316	0.4588	1.1004	0.072*
H14B	1.7304	0.4819	1.1373	0.072*
H14C	1.6307	0.4018	1.2180	0.072*
C15	1.7591 (3)	0.2284 (3)	1.0724 (2)	0.0476 (6)
H15A	1.8598	0.2922	1.0746	0.071*
H15B	1.7440	0.1449	1.0085	0.071*
H15C	1.7710	0.2111	1.1608	0.071*
C16	0.7171 (3)	0.4627 (2)	0.7195 (2)	0.0363 (5)
H16A	0.7307	0.5540	0.7680	0.055*
H16B	0.7619	0.4109	0.7819	0.055*
H16C	0.5982	0.4217	0.6743	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.01875 (11)	0.04364 (13)	0.03281 (12)	0.00906 (8)	0.00246 (8)	0.00820 (8)
S	0.0252 (2)	0.01788 (19)	0.0290 (2)	0.00410 (15)	0.00857 (18)	0.00199 (16)
O1	0.0193 (6)	0.0199 (5)	0.0249 (6)	0.0061 (4)	0.0063 (5)	0.0035 (5)
O2	0.0212 (6)	0.0340 (6)	0.0203 (6)	0.0080 (5)	0.0042 (5)	0.0061 (5)
O3	0.0244 (7)	0.0439 (8)	0.0290 (7)	0.0089 (6)	0.0098 (6)	0.0008 (6)
O4	0.0438 (8)	0.0243 (6)	0.0391 (8)	0.0130 (6)	0.0164 (6)	0.0136 (6)
C1	0.0208 (8)	0.0177 (7)	0.0213 (8)	0.0042 (6)	0.0060 (6)	0.0038 (6)
C2	0.0215 (8)	0.0201 (7)	0.0174 (8)	0.0050 (6)	0.0060 (6)	0.0055 (6)
C3	0.0231 (8)	0.0240 (8)	0.0213 (8)	0.0084 (6)	0.0067 (7)	0.0076 (6)
C4	0.0171 (8)	0.0325 (9)	0.0201 (8)	0.0066 (6)	0.0048 (6)	0.0086 (7)
C5	0.0221 (8)	0.0270 (8)	0.0207 (8)	0.0005 (6)	0.0060 (7)	0.0034 (7)
C6	0.0265 (9)	0.0201 (8)	0.0243 (9)	0.0047 (6)	0.0100 (7)	0.0020 (6)
C7	0.0196 (8)	0.0227 (8)	0.0200 (8)	0.0068 (6)	0.0072 (6)	0.0061 (6)
C8	0.0208 (8)	0.0192 (7)	0.0206 (8)	0.0039 (6)	0.0070 (6)	0.0037 (6)
C9	0.0190 (8)	0.0235 (8)	0.0250 (9)	0.0063 (6)	0.0063 (7)	0.0053 (6)
C10	0.0178 (8)	0.0192 (7)	0.0264 (9)	−0.0002 (6)	0.0053 (7)	0.0015 (6)
C11	0.0268 (10)	0.0529 (12)	0.0216 (9)	0.0053 (8)	0.0065 (7)	0.0102 (8)
C12	0.0317 (10)	0.0338 (9)	0.0228 (9)	0.0054 (7)	0.0037 (7)	0.0109 (7)
C13	0.0263 (9)	0.0348 (10)	0.0224 (9)	0.0052 (7)	0.0021 (7)	0.0080 (7)
C14	0.0529 (14)	0.0353 (11)	0.0417 (13)	0.0034 (10)	0.0010 (11)	−0.0012 (10)
C15	0.0338 (12)	0.0684 (16)	0.0400 (13)	0.0200 (11)	0.0044 (10)	0.0130 (11)
C16	0.0512 (12)	0.0335 (10)	0.0317 (11)	0.0175 (9)	0.0215 (10)	0.0054 (8)

Geometric parameters (Å, º) top

Br—C4	1.9047 (17)	C9—C10	1.517 (2)
S—O4	1.4984 (14)	C9—H9A	0.9700
S—C1	1.7651 (16)	C9—H9B	0.9700
S—C16	1.796 (2)	C11—C12	1.509 (3)
O1—C7	1.374 (2)	C11—H11A	0.9700
O1—C8	1.3791 (19)	C11—H11B	0.9700
O2—C10	1.335 (2)	C12—C13	1.527 (3)
O2—C11	1.464 (2)	C12—H12A	0.9700
O3—C10	1.208 (2)	C12—H12B	0.9700
C1—C8	1.358 (2)	C13—C14	1.523 (3)
C1—C2	1.449 (2)	C13—C15	1.528 (3)
C2—C3	1.397 (2)	C13—H13	0.9800
C2—C7	1.403 (2)	C14—H14A	0.9600
C3—C4	1.384 (2)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.400 (2)	C15—H15A	0.9600
C5—C6	1.385 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.381 (2)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C8—C9	1.484 (2)	C16—H16C	0.9600

O4—S—C1	106.60 (8)	O2—C10—C9	111.26 (14)
O4—S—C16	105.52 (9)	O2—C11—C12	107.96 (15)
C1—S—C16	98.25 (9)	O2—C11—H11A	110.1
C7—O1—C8	106.47 (12)	C12—C11—H11A	110.1
C10—O2—C11	114.98 (14)	O2—C11—H11B	110.1
C8—C1—C2	107.39 (14)	C12—C11—H11B	110.1
C8—C1—S	124.39 (13)	H11A—C11—H11B	108.4
C2—C1—S	128.16 (12)	C11—C12—C13	116.26 (16)
C3—C2—C7	119.64 (15)	C11—C12—H12A	108.2
C3—C2—C1	135.88 (15)	C13—C12—H12A	108.2
C7—C2—C1	104.44 (14)	C11—C12—H12B	108.2
C4—C3—C2	116.29 (15)	C13—C12—H12B	108.2
C4—C3—H3	121.9	H12A—C12—H12B	107.4
C2—C3—H3	121.9	C14—C13—C12	112.39 (18)
C3—C4—C5	123.73 (15)	C14—C13—C15	109.96 (18)
C3—C4—Br	118.49 (13)	C12—C13—C15	108.72 (17)
C5—C4—Br	117.77 (13)	C14—C13—H13	108.6
C6—C5—C4	120.00 (15)	C12—C13—H13	108.6
C6—C5—H5	120.0	C15—C13—H13	108.6
C4—C5—H5	120.0	C13—C14—H14A	109.5
C7—C6—C5	116.59 (15)	C13—C14—H14B	109.5
C7—C6—H6	121.7	H14A—C14—H14B	109.5
C5—C6—H6	121.7	C13—C14—H14C	109.5
O1—C7—C6	125.46 (15)	H14A—C14—H14C	109.5
O1—C7—C2	110.78 (14)	H14B—C14—H14C	109.5
C6—C7—C2	123.75 (15)	C13—C15—H15A	109.5
C1—C8—O1	110.91 (14)	C13—C15—H15B	109.5
C1—C8—C9	133.32 (15)	H15A—C15—H15B	109.5
O1—C8—C9	115.60 (14)	C13—C15—H15C	109.5
C8—C9—C10	111.79 (14)	H15A—C15—H15C	109.5
C8—C9—H9A	109.3	H15B—C15—H15C	109.5
C10—C9—H9A	109.3	S—C16—H16A	109.5
C8—C9—H9B	109.3	S—C16—H16B	109.5
C10—C9—H9B	109.3	H16A—C16—H16B	109.5
H9A—C9—H9B	107.9	S—C16—H16C	109.5
O3—C10—O2	123.95 (17)	H16A—C16—H16C	109.5
O3—C10—C9	124.76 (16)	H16B—C16—H16C	109.5

O4—S—C1—C8	137.41 (15)	C1—C2—C7—O1	0.44 (18)
C16—S—C1—C8	−113.60 (16)	C3—C2—C7—C6	1.1 (2)
O4—S—C1—C2	−39.41 (17)	C1—C2—C7—C6	179.05 (16)
C16—S—C1—C2	69.57 (17)	C2—C1—C8—O1	0.16 (19)
C8—C1—C2—C3	177.04 (18)	S—C1—C8—O1	−177.22 (11)
S—C1—C2—C3	−5.7 (3)	C2—C1—C8—C9	−174.86 (17)
C8—C1—C2—C7	−0.36 (18)	S—C1—C8—C9	7.8 (3)
S—C1—C2—C7	176.90 (13)	C7—O1—C8—C1	0.11 (18)
C7—C2—C3—C4	−0.5 (2)	C7—O1—C8—C9	176.10 (14)
C1—C2—C3—C4	−177.59 (18)	C1—C8—C9—C10	73.0 (2)
C2—C3—C4—C5	−0.2 (2)	O1—C8—C9—C10	−101.84 (16)
C2—C3—C4—Br	−179.23 (12)	C11—O2—C10—O3	3.6 (2)
C3—C4—C5—C6	0.3 (3)	C11—O2—C10—C9	−178.09 (14)
Br—C4—C5—C6	179.34 (13)	C8—C9—C10—O3	−26.2 (2)
C4—C5—C6—C7	0.3 (2)	C8—C9—C10—O2	155.53 (14)
C8—O1—C7—C6	−178.93 (16)	C10—O2—C11—C12	−179.92 (14)
C8—O1—C7—C2	−0.35 (17)	O2—C11—C12—C13	70.7 (2)
C5—C6—C7—O1	177.40 (15)	C11—C12—C13—C14	62.3 (2)
C5—C6—C7—C2	−1.0 (2)	C11—C12—C13—C15	−175.75 (17)
C3—C2—C7—O1	−177.47 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.56	3.437 (2)	157
C5—H5···O3ⁱⁱ	0.93	2.51	3.383 (2)	157
C9—H9A···O4ⁱⁱⁱ	0.97	2.26	3.192 (2)	162
C9—H9B···O1^iv	0.97	2.61	3.541 (2)	160

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉BrO₄S
M_r	387.28
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.3704 (4), 10.2956 (6), 10.524 (1)
α, β, γ (°)	99.977 (1), 105.230 (1), 100.681 (1)
V (Å³)	836.04 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.60
Crystal size (mm)	0.60 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1999)
T_min, T_max	0.302, 0.769
No. of measured, independent and observed [I > 2σ(I)] reflections	7179, 3579, 3304
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.072, 1.04
No. of reflections	3579
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.59

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
C3—H3···O4ⁱ	0.93	2.56	3.437 (2)	157.3
C5—H5···O3ⁱⁱ	0.93	2.51	3.383 (2)	157.0
C9—H9A···O4ⁱⁱⁱ	0.97	2.26	3.192 (2)	161.6
C9—H9B···O1^iv	0.97	2.61	3.541 (2)	159.7

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

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. (2009a). Acta Cryst. E65, o265. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o520. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1999). 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
Ward, R. S. (1997). Nat. Prod. Rep. 14, 43–74. CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 7| July 2009| Page o1498

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