Isoamyl 2-(5-bromo-3-methyl-sulfin-yl-1-benzofuran-2--yl)acetate.

In the title compound, C(16)H(19)BrO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure exhibits aromatic π-π inter-actions between the benzene rings of adjacent mol-ecules [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 = 387.28

Triclinic,

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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.04

3579 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.59 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 I. DOI: 10.1107/S1600536809020613/cv2569sup1.cif

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

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

C16H19BrO4S	Z = 2
Mr = 387.28	F(000) = 396
Triclinic, P1	Dx = 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

Bruker SMART CCD diffractometer	3579 independent reflections
Radiation source: fine-focus sealed tube	3304 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.6°
φ– and ω–scans	h = −10→10
Absorption correction: multi-scan SADABS (Sheldrick, 1999)	k = −13→13
Tmin = 0.302, Tmax = 0.769	l = −13→13
7179 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)] = 0.027	Hydrogen site location: difference Fourier map
wR(F2) = 0.072	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2834P] where P = (Fo2 + 2Fc2)/3
3579 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O1iv	0.97	2.61	3.541 (2)	160

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⋯O1iv	0.97	2.61	3.541 (2)	160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .