Butyl 2-(5-bromo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(15)H(17)BrO(4)S, the methyl-sulfinyl 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 inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.698 (4) Å], and by C-H⋯π inter-actions between a methyl-ene H atom of the butyl group and the benzene ring of the benzofuran system. Additionally, the crystal structure exhibits weak inter-molecular 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 = 373.26

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.14

3179 reflections

229 parameters

64 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.50 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043985/tk2347sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H17BrO4S	Z = 2
Mr = 373.26	F(000) = 380
Triclinic, P1	Dx = 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

Bruker SMART CCD diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	2645 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
Tmin = 0.353, Tmax = 0.451	l = −12→12
6560 measured reflections

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(Fo2) + (0.0442P)2 + 0.2004P] where P = (Fo2 + 2Fc2)/3
3179 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.30 e Å−3
64 restraints	Δρmin = −0.50 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .