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

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

doi:10.1107/S1600536808043985

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o265

doi:10.1107/S1600536808043985

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Butyl 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 18 December 2008; accepted 25 December 2008; online 8 January 2009)

In the title compound, C₁₅H₁₇BrO₄S, the methylsulfinyl O atom and the methyl substituents lie on opposite sides of the plane through the benzofuran fragment. The crystal structure is stabilized by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.698 (4) Å], and by C—H⋯π interactions between a methylene H atom of the butyl group and the benzene ring of the benzofuran system. Additionally, the crystal structure exhibits weak intermolecular C—H⋯O contacts. The butyl group is disordered over two positions, with site-occupancy factors, from refinement, of 0.720 (8) and 0.280 (8).

Related literature

For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₅H₁₇BrO₄S
M_r = 373.26
Triclinic, $[P \overline 1]$
a = 8.420 (1) Å
b = 10.255 (1) Å
c = 10.306 (1) Å
α = 97.503 (2)°
β = 99.711 (2)°
γ = 108.678 (2)°
V = 814.55 (15) Å³
Z = 2
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 298 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.353, T_max = 0.451
6560 measured reflections
3179 independent reflections
2645 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.14
3179 reflections
229 parameters
64 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12A—H12A⋯Cgⁱ	0.97	2.78	3.698 (5)	158
C5—H5⋯O3ⁱⁱ	0.93	2.55	3.405 (3)	153
C9—H9B⋯O4ⁱⁱⁱ	0.97	2.30	3.248 (3)	167
Symmetry codes: (i) x+1, y+1, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -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 datablocks global, I. DOI: 10.1107/S1600536808043985/tk2347sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043985/tk2347Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. isopropyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008b). Herein, we describe the crystal structure of the title compound, (I).

The benzofuran unit is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The butyl group is disordered over two positions with site-occupancy factors of 0.720 (8) (for atoms labelled B) and 0.280 (8) (B) in Fig. 1. The molecular packing is stabilized by intermolecular π—π interactions: the Cg···Cgⁱⁱ distance is 3.698 (4) Å, where Cg is the centroid of the C2–C7 ring, symmetry code as in Fig. 2. The molecular packing is further stabilized by C—H···π interactions between the methylene-H and the benzene ring of the benzofuran system, with a C12A—H12A···Cgⁱ separation of 2.78 Å, Table 1; Cg is the centroid of the C2–C7 benzene ring. In addition, weak intermolecular C—H···O contacts are observed, Table 1. One C-H···O contact occurs between a benzene-H and the O3-oxygen, and a second between a methylene-H and the O4-oxygen atom.

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. (2008a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (148 mg, 0.66 mmol) was added in small portions to a stirred solution of butyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (214 mg, 0.6 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer 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 (I) as a colorless solid [yield 80%, m.p. 381–382 K; R_f = 0.65 (hexane-ethyl acetate, 1;2 v/v)]. Single crystals were obtained by evaporation of an acetone solution of (I). Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.92 (t, J = 7.32 Hz, 3H), 1.31–1.41 (m, 2H), 1.59–1.67 (m, 2H), 3.07 (s, 3H), 4.04 (s, 2H), 4.15 (t, J = 6.6 Hz, 2H), 7.39 (d, J = 8.8 Hz, 1H), 7.49 (dd, J = 8.8 Hz and J = 2.2 Hz, 1H), 8.11 (d, J = 1.84 Hz, 1H); EI—MS 374 [M+2], 372 [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 (I), showing displacement ellipsoids drawn at the 30% probability level. The butyl group is disordered over two positions with the major component having a site occupancy = 0.720 (8).

Fig. 2. Diagram illustrating the π—π, C—H···π and C—H···O interactions (dotted lines) in the crystal structure of (I). Cg denotes a ring centroid. The disordered component of the butyl group, part B, has been omitted for clarity as have H atoms not involved in intermolecular contacts. Symmetry codes: (i) x + 1, y + 1, z; (ii) -x, 1 - y, -z; (iii) -x + 1, -y + 1, -z + 1; (iv) -x + 1, -y + 2, -z; (v) x - 1, y - 1, z.

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

Crystal data top

C₁₅H₁₇BrO₄S	Z = 2
M_r = 373.26	F(000) = 380
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.420 (1) Å	Cell parameters from 3446 reflections
b = 10.255 (1) Å	θ = 2.6–27.0°
c = 10.306 (1) Å	µ = 2.66 mm⁻¹
α = 97.503 (2)°	T = 298 K
β = 99.711 (2)°	Block, colorless
γ = 108.678 (2)°	0.40 × 0.40 × 0.30 mm
V = 814.55 (15) Å³

Data collection top

Bruker SMART CCD diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	2645 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
T_min = 0.353, T_max = 0.451	l = −12→12
6560 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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F²) = 0.089	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0442P)² + 0.2004P] where P = (F_o² + 2F_c²)/3
3179 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.30 e Å⁻³
64 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₅H₁₇BrO₄S	γ = 108.678 (2)°
M_r = 373.26	V = 814.55 (15) Å³
Triclinic, P1	Z = 2
a = 8.420 (1) Å	Mo Kα radiation
b = 10.255 (1) Å	µ = 2.66 mm⁻¹
c = 10.306 (1) Å	T = 298 K
α = 97.503 (2)°	0.40 × 0.40 × 0.30 mm
β = 99.711 (2)°

Data collection top

Bruker SMART CCD diffractometer	3179 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2645 reflections with I > 2σ(I)
T_min = 0.353, T_max = 0.451	R_int = 0.017
6560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	64 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.14	Δρ_max = 0.30 e Å⁻³
3179 reflections	Δρ_min = −0.50 e Å⁻³
229 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	Occ. (<1)
Br	−0.42599 (4)	0.24082 (3)	0.12584 (3)	0.06775 (14)
S	0.32177 (9)	0.58854 (7)	0.45871 (6)	0.04988 (17)
O1	0.3033 (2)	0.46045 (17)	0.07725 (15)	0.0442 (4)
O2	0.7594 (3)	0.8276 (2)	0.2120 (2)	0.0686 (6)
O3	0.5174 (3)	0.8291 (2)	0.2711 (2)	0.0721 (6)
O4	0.2197 (3)	0.4784 (2)	0.52321 (18)	0.0618 (5)
C1	0.2665 (3)	0.5195 (2)	0.2849 (2)	0.0413 (5)
C2	0.0997 (3)	0.4347 (2)	0.2012 (2)	0.0401 (5)
C3	−0.0682 (3)	0.3882 (3)	0.2186 (2)	0.0447 (5)
H3	−0.0941	0.4108	0.3010	0.054*
C4	−0.1944 (3)	0.3070 (3)	0.1078 (3)	0.0472 (6)
C5	−0.1604 (4)	0.2716 (3)	−0.0175 (3)	0.0509 (6)
H5	−0.2500	0.2159	−0.0889	0.061*
C6	0.0052 (3)	0.3188 (3)	−0.0354 (2)	0.0478 (6)
H6	0.0307	0.2966	−0.1181	0.057*
C7	0.1318 (3)	0.4008 (2)	0.0749 (2)	0.0414 (5)
C8	0.3827 (3)	0.5320 (2)	0.2067 (2)	0.0417 (5)
C9	0.5701 (3)	0.6117 (3)	0.2310 (3)	0.0460 (6)
H9A	0.6150	0.5767	0.1586	0.055*
H9B	0.6281	0.5959	0.3140	0.055*
C10	0.6090 (3)	0.7675 (3)	0.2403 (3)	0.0506 (6)
C11A	0.8140 (8)	0.9810 (14)	0.2252 (11)	0.087 (3)	0.720 (8)
H11A	0.8117	1.0245	0.3139	0.104*	0.720 (8)
H11B	0.7375	1.0053	0.1590	0.104*	0.720 (8)
C12A	0.9913 (6)	1.0302 (6)	0.2033 (6)	0.0749 (16)	0.720 (8)
H12A	1.0207	1.1232	0.1821	0.090*	0.720 (8)
H12B	1.0036	0.9664	0.1307	0.090*	0.720 (8)
C13A	1.1021 (6)	1.0324 (8)	0.3331 (7)	0.098 (2)	0.720 (8)
H13A	1.0712	1.0833	0.4050	0.117*	0.720 (8)
H13B	1.0766	0.9366	0.3464	0.117*	0.720 (8)
C14A	1.2899 (7)	1.0964 (9)	0.3450 (10)	0.134 (3)	0.720 (8)
H14A	1.3499	1.0967	0.4330	0.202*	0.720 (8)
H14B	1.3173	1.1911	0.3309	0.202*	0.720 (8)
H14C	1.3243	1.0429	0.2788	0.202*	0.720 (8)
C11B	0.806 (2)	0.973 (3)	0.183 (2)	0.070 (5)	0.280 (8)
H11C	0.7231	1.0153	0.2025	0.084*	0.280 (8)
H11D	0.8138	0.9721	0.0903	0.084*	0.280 (8)
C12B	0.9768 (19)	1.049 (2)	0.275 (3)	0.127 (7)	0.280 (8)
H12C	0.9614	1.0361	0.3645	0.153*	0.280 (8)
H12D	1.0003	1.1475	0.2746	0.153*	0.280 (8)
C13B	1.1377 (19)	1.0231 (18)	0.2628 (16)	0.087 (5)	0.280 (8)
H13C	1.1320	0.9270	0.2622	0.105*	0.280 (8)
H13D	1.1884	1.0601	0.1915	0.105*	0.280 (8)
C14B	1.207 (3)	1.117 (2)	0.3964 (16)	0.124 (6)	0.280 (8)
H14D	1.3305	1.1547	0.4133	0.186*	0.280 (8)
H14E	1.1729	1.0655	0.4643	0.186*	0.280 (8)
H14F	1.1634	1.1931	0.3985	0.186*	0.280 (8)
C15	0.2192 (5)	0.7173 (3)	0.4576 (3)	0.0679 (8)
H15A	0.0971	0.6710	0.4266	0.102*
H15B	0.2615	0.7788	0.3987	0.102*
H15C	0.2442	0.7710	0.5468	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04457 (17)	0.0686 (2)	0.0882 (3)	0.01726 (14)	0.01642 (15)	0.01369 (16)
S	0.0507 (4)	0.0625 (4)	0.0376 (3)	0.0229 (3)	0.0092 (3)	0.0067 (3)
O1	0.0471 (9)	0.0509 (10)	0.0400 (9)	0.0212 (8)	0.0158 (7)	0.0093 (7)
O2	0.0515 (11)	0.0466 (11)	0.1135 (17)	0.0178 (9)	0.0256 (11)	0.0246 (11)
O3	0.0637 (13)	0.0590 (12)	0.1004 (16)	0.0315 (11)	0.0233 (12)	0.0072 (11)
O4	0.0721 (13)	0.0801 (14)	0.0466 (10)	0.0348 (11)	0.0218 (9)	0.0265 (9)
C1	0.0462 (13)	0.0449 (13)	0.0361 (12)	0.0191 (10)	0.0103 (10)	0.0099 (10)
C2	0.0474 (13)	0.0399 (12)	0.0393 (12)	0.0203 (10)	0.0129 (10)	0.0123 (10)
C3	0.0474 (13)	0.0471 (13)	0.0471 (14)	0.0220 (11)	0.0160 (11)	0.0146 (11)
C4	0.0448 (13)	0.0421 (13)	0.0588 (15)	0.0192 (11)	0.0119 (11)	0.0135 (11)
C5	0.0537 (15)	0.0468 (14)	0.0504 (14)	0.0221 (12)	0.0019 (12)	0.0044 (11)
C6	0.0561 (15)	0.0515 (14)	0.0400 (13)	0.0261 (12)	0.0099 (11)	0.0061 (11)
C7	0.0449 (13)	0.0420 (12)	0.0440 (12)	0.0211 (10)	0.0134 (10)	0.0117 (10)
C8	0.0462 (13)	0.0441 (13)	0.0399 (12)	0.0209 (10)	0.0111 (10)	0.0112 (10)
C9	0.0447 (13)	0.0512 (14)	0.0480 (14)	0.0215 (11)	0.0144 (11)	0.0132 (11)
C10	0.0463 (14)	0.0517 (15)	0.0531 (15)	0.0191 (12)	0.0068 (11)	0.0085 (12)
C11A	0.072 (4)	0.059 (4)	0.137 (7)	0.029 (3)	0.019 (4)	0.032 (5)
C12A	0.075 (3)	0.044 (2)	0.105 (4)	0.013 (2)	0.022 (3)	0.028 (3)
C13A	0.072 (3)	0.080 (4)	0.117 (5)	0.002 (3)	0.004 (3)	0.024 (4)
C14A	0.077 (4)	0.120 (5)	0.175 (7)	−0.001 (4)	0.024 (4)	0.018 (5)
C11B	0.072 (7)	0.040 (8)	0.096 (9)	0.008 (5)	0.016 (6)	0.034 (7)
C12B	0.110 (8)	0.109 (10)	0.162 (12)	0.054 (8)	−0.005 (7)	0.028 (9)
C13B	0.085 (7)	0.086 (8)	0.089 (8)	0.028 (6)	0.022 (6)	0.012 (6)
C14B	0.122 (10)	0.135 (10)	0.109 (9)	0.053 (8)	0.012 (7)	0.000 (7)
C15	0.087 (2)	0.0654 (19)	0.0637 (18)	0.0394 (17)	0.0291 (16)	0.0087 (15)

Geometric parameters (Å, º) top

Br—C4	1.899 (3)	C11A—H11A	0.9700
S—O4	1.491 (2)	C11A—H11B	0.9700
S—C1	1.762 (2)	C12A—C13A	1.489 (2)
S—C15	1.794 (3)	C12A—H12A	0.9700
O1—C7	1.370 (3)	C12A—H12B	0.9700
O1—C8	1.376 (3)	C13A—C14A	1.482 (2)
O2—C10	1.319 (3)	C13A—H13A	0.9700
O2—C11A	1.471 (14)	C13A—H13B	0.9700
O2—C11B	1.50 (3)	C14A—H14A	0.9600
O3—C10	1.199 (3)	C14A—H14B	0.9600
C1—C8	1.355 (3)	C14A—H14C	0.9600
C1—C2	1.444 (3)	C11B—C12B	1.481 (2)
C2—C3	1.391 (3)	C11B—H11C	0.9700
C2—C7	1.396 (3)	C11B—H11D	0.9700
C3—C4	1.380 (4)	C12B—C13B	1.483 (2)
C3—H3	0.9300	C12B—H12C	0.9700
C4—C5	1.396 (4)	C12B—H12D	0.9700
C5—C6	1.376 (4)	C13B—C14B	1.481 (2)
C5—H5	0.9300	C13B—H13C	0.9700
C6—C7	1.380 (3)	C13B—H13D	0.9700
C6—H6	0.9300	C14B—H14D	0.9600
C8—C9	1.486 (3)	C14B—H14E	0.9600
C9—C10	1.511 (4)	C14B—H14F	0.9600
C9—H9A	0.9700	C15—H15A	0.9600
C9—H9B	0.9700	C15—H15B	0.9600
C11A—C12A	1.482 (2)	C15—H15C	0.9600

O4—S—C1	106.92 (12)	C11A—C12A—H12A	110.8
O4—S—C15	105.78 (14)	C13A—C12A—H12A	110.8
C1—S—C15	98.46 (13)	C11A—C12A—H12B	110.8
C7—O1—C8	106.62 (17)	C13A—C12A—H12B	110.8
C10—O2—C11A	115.2 (3)	H12A—C12A—H12B	108.9
C10—O2—C11B	120.0 (10)	C14A—C13A—C12A	115.7 (6)
C11A—O2—C11B	16.2 (11)	C14A—C13A—H13A	108.4
C8—C1—C2	107.4 (2)	C12A—C13A—H13A	108.4
C8—C1—S	123.77 (19)	C14A—C13A—H13B	108.4
C2—C1—S	128.70 (18)	C12A—C13A—H13B	108.4
C3—C2—C7	119.5 (2)	H13A—C13A—H13B	107.4
C3—C2—C1	135.8 (2)	C13A—C14A—H14A	109.5
C7—C2—C1	104.6 (2)	C13A—C14A—H14B	109.5
C4—C3—C2	116.8 (2)	H14A—C14A—H14B	109.5
C4—C3—H3	121.6	C13A—C14A—H14C	109.5
C2—C3—H3	121.6	H14A—C14A—H14C	109.5
C3—C4—C5	123.2 (2)	H14B—C14A—H14C	109.5
C3—C4—Br	118.51 (19)	O2—C11B—C12B	104 (2)
C5—C4—Br	118.29 (19)	O2—C11B—H11C	111.1
C6—C5—C4	120.2 (2)	C12B—C11B—H11C	111.1
C6—C5—H5	119.9	O2—C11B—H11D	111.1
C4—C5—H5	119.9	C12B—C11B—H11D	111.1
C5—C6—C7	116.8 (2)	H11C—C11B—H11D	109.0
C5—C6—H6	121.6	C11B—C12B—C13B	125 (2)
C7—C6—H6	121.6	C11B—C12B—H12C	106.1
O1—C7—C6	125.9 (2)	C13B—C12B—H12C	106.1
O1—C7—C2	110.7 (2)	C11B—C12B—H12D	106.1
C6—C7—C2	123.5 (2)	C13B—C12B—H12D	106.1
C1—C8—O1	110.7 (2)	H12C—C12B—H12D	106.3
C1—C8—C9	133.3 (2)	C14B—C13B—C12B	83.6 (14)
O1—C8—C9	115.9 (2)	C14B—C13B—H13C	114.7
C8—C9—C10	112.3 (2)	C12B—C13B—H13C	114.7
C8—C9—H9A	109.1	C14B—C13B—H13D	114.7
C10—C9—H9A	109.1	C12B—C13B—H13D	114.7
C8—C9—H9B	109.1	H13C—C13B—H13D	111.8
C10—C9—H9B	109.1	C13B—C14B—H14D	109.5
H9A—C9—H9B	107.9	C13B—C14B—H14E	109.5
O3—C10—O2	124.3 (3)	H14D—C14B—H14E	109.5
O3—C10—C9	124.9 (3)	C13B—C14B—H14F	109.5
O2—C10—C9	110.8 (2)	H14D—C14B—H14F	109.5
O2—C11A—C12A	107.2 (8)	H14E—C14B—H14F	109.5
O2—C11A—H11A	110.3	S—C15—H15A	109.5
C12A—C11A—H11A	110.3	S—C15—H15B	109.5
O2—C11A—H11B	110.3	H15A—C15—H15B	109.5
C12A—C11A—H11B	110.3	S—C15—H15C	109.5
H11A—C11A—H11B	108.5	H15A—C15—H15C	109.5
C11A—C12A—C13A	104.5 (6)	H15B—C15—H15C	109.5

O4—S—C1—C8	−136.3 (2)	C2—C1—C8—O1	−0.3 (3)
C15—S—C1—C8	114.3 (2)	S—C1—C8—O1	176.29 (16)
O4—S—C1—C2	39.5 (2)	C2—C1—C8—C9	175.7 (2)
C15—S—C1—C2	−69.9 (2)	S—C1—C8—C9	−7.8 (4)
C8—C1—C2—C3	−177.6 (3)	C7—O1—C8—C1	−0.3 (2)
S—C1—C2—C3	6.1 (4)	C7—O1—C8—C9	−177.00 (19)
C8—C1—C2—C7	0.7 (3)	C1—C8—C9—C10	−73.0 (3)
S—C1—C2—C7	−175.63 (18)	O1—C8—C9—C10	102.8 (2)
C7—C2—C3—C4	1.4 (3)	C11A—O2—C10—O3	2.1 (6)
C1—C2—C3—C4	179.5 (2)	C11B—O2—C10—O3	−15.4 (11)
C2—C3—C4—C5	−0.3 (3)	C11A—O2—C10—C9	−176.9 (5)
C2—C3—C4—Br	−179.94 (16)	C11B—O2—C10—C9	165.7 (10)
C3—C4—C5—C6	−0.5 (4)	C8—C9—C10—O3	24.4 (4)
Br—C4—C5—C6	179.14 (18)	C8—C9—C10—O2	−156.7 (2)
C4—C5—C6—C7	0.1 (4)	C10—O2—C11A—C12A	174.3 (5)
C8—O1—C7—C6	−179.6 (2)	C11B—O2—C11A—C12A	−74 (4)
C8—O1—C7—C2	0.8 (2)	O2—C11A—C12A—C13A	−78.9 (8)
C5—C6—C7—O1	−178.5 (2)	C11A—C12A—C13A—C14A	−172.1 (9)
C5—C6—C7—C2	1.1 (4)	C10—O2—C11B—C12B	128.1 (15)
C3—C2—C7—O1	177.69 (19)	C11A—O2—C11B—C12B	51 (3)
C1—C2—C7—O1	−0.9 (2)	O2—C11B—C12B—C13B	69 (3)
C3—C2—C7—C6	−1.9 (3)	C11B—C12B—C13B—C14B	−171 (3)
C1—C2—C7—C6	179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12A···Cgⁱ	0.97	2.78	3.698 (5)	158
C5—H5···O3ⁱⁱ	0.93	2.55	3.405 (3)	153
C9—H9B···O4ⁱⁱⁱ	0.97	2.30	3.248 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇BrO₄S
M_r	373.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.420 (1), 10.255 (1), 10.306 (1)
α, β, γ (°)	97.503 (2), 99.711 (2), 108.678 (2)
V (Å³)	814.55 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.66
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.353, 0.451
No. of measured, independent and observed [I > 2σ(I)] reflections	6560, 3179, 2645
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.089, 1.14
No. of reflections	3179
No. of parameters	229
No. of restraints	64
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.50

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
C12A—H12A···Cgⁱ	0.97	2.78	3.698 (5)	158
C5—H5···O3ⁱⁱ	0.93	2.55	3.405 (3)	153
C9—H9B···O4ⁱⁱⁱ	0.97	2.30	3.248 (3)	167

Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −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. (2008a). Acta Cryst. E64, o2250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2397. 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. (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

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Volume 65| Part 2| February 2009| Page o265

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