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

In the title compound, C(14)H(15)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 is stabilized by C-H⋯π inter-actions between a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C14H15BrO4S

M = 359.23

Triclinic,

a = 7.947 (1) Å

b = 10.078 (1) Å

c = 10.868 (1) Å

α = 69.623 (2)°

β = 82.027 (2)°

γ = 67.409 (2)°

V = 753.33 (14) Å3

Z = 2

Mo Kα radiation

μ = 2.88 mm−1

T = 298 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.321, T max = 0.559

3979 measured reflections

2604 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.02

2604 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.46 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/S160053680803506X/sg2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803506X/sg2276Isup2.hkl

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

C14H15BrO4S	Z = 2
Mr = 359.23	F000 = 364
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P_1	Melting point = 429–430 K
a = 7.947 (1) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.078 (1) Å	Cell parameters from 2313 reflections
c = 10.868 (1) Å	θ = 2.8–28.2º
α = 69.623 (2)º	µ = 2.88 mm−1
β = 82.027 (2)º	T = 298 (2) K
γ = 67.409 (2)º	Block, colorless
V = 753.33 (14) Å3	0.40 × 0.40 × 0.20 mm

Bruker SMART CCD diffractometer	2604 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.011
Detector resolution: 10.0 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 2.3º
φ and ω scans	h = −9→5
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −11→11
Tmin = 0.321, Tmax = 0.559	l = −12→12
3979 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.042P)2 + 0.4644P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2604 reflections	Δρmax = 0.46 e Å−3
181 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br	0.70616 (5)	0.79293 (4)	0.62791 (4)	0.07083 (16)
S	0.25401 (10)	0.39786 (9)	0.96079 (7)	0.0469 (2)
O1	0.1648 (2)	0.5361 (2)	0.58148 (17)	0.0407 (4)
O2	0.2529 (3)	0.5174 (3)	1.0122 (2)	0.0624 (6)
O3	−0.0241 (3)	0.1540 (2)	0.7747 (2)	0.0532 (5)
O4	0.2603 (3)	0.1418 (3)	0.7888 (3)	0.0651 (6)
C1	0.2522 (4)	0.4734 (3)	0.7885 (3)	0.0377 (6)
C2	0.3526 (3)	0.5637 (3)	0.7033 (3)	0.0367 (6)
C3	0.4811 (4)	0.6187 (3)	0.7202 (3)	0.0422 (6)
H3	0.5264	0.5956	0.8026	0.051*
C4	0.5377 (4)	0.7090 (3)	0.6087 (3)	0.0457 (7)
C5	0.4752 (4)	0.7448 (3)	0.4839 (3)	0.0487 (7)
H5	0.5184	0.8063	0.4119	0.058*
C6	0.3495 (4)	0.6897 (3)	0.4662 (3)	0.0441 (7)
H6	0.3065	0.7116	0.3834	0.053*
C7	0.2906 (4)	0.6004 (3)	0.5777 (3)	0.0377 (6)
C8	0.1423 (4)	0.4614 (3)	0.7115 (3)	0.0389 (6)
C9	0.4813 (5)	0.2606 (4)	0.9795 (3)	0.0648 (9)
H9A	0.5068	0.2067	1.0711	0.097*
H9B	0.5660	0.3113	0.9426	0.097*
H9C	0.4930	0.1903	0.9350	0.097*
C10	0.0116 (4)	0.3821 (3)	0.7411 (3)	0.0437 (7)
H10A	−0.0696	0.4239	0.6671	0.052*
H10B	−0.0617	0.4014	0.8165	0.052*
C11	0.1016 (4)	0.2131 (3)	0.7692 (3)	0.0416 (6)
C12	0.0375 (5)	−0.0102 (4)	0.7976 (4)	0.0630 (9)
H12	0.1468	−0.0652	0.8524	0.076*
C13	0.0742 (7)	−0.0350 (4)	0.6682 (5)	0.0978 (16)
H13A	0.1649	0.0055	0.6220	0.117*
H13B	−0.0361	0.0153	0.6180	0.117*
H13C	0.1175	−0.1418	0.6810	0.117*
C14	−0.1201 (8)	−0.0562 (5)	0.8665 (4)	0.1008 (16)
H14A	−0.2254	−0.0017	0.8110	0.121*
H14B	−0.1470	−0.0329	0.9471	0.121*
H14C	−0.0881	−0.1633	0.8851	0.121*

	U11	U22	U33	U12	U13	U23
Br	0.0636 (2)	0.0633 (2)	0.0936 (3)	−0.04221 (19)	−0.00607 (19)	−0.0111 (2)
S	0.0499 (4)	0.0555 (5)	0.0372 (4)	−0.0265 (4)	−0.0032 (3)	−0.0078 (3)
O1	0.0454 (11)	0.0435 (11)	0.0376 (10)	−0.0190 (9)	−0.0054 (8)	−0.0131 (9)
O2	0.0709 (15)	0.0739 (16)	0.0505 (13)	−0.0259 (12)	−0.0048 (11)	−0.0285 (12)
O3	0.0584 (13)	0.0409 (11)	0.0657 (14)	−0.0251 (10)	−0.0142 (10)	−0.0103 (10)
O4	0.0492 (14)	0.0484 (13)	0.0931 (18)	−0.0181 (11)	−0.0084 (12)	−0.0138 (12)
C1	0.0402 (15)	0.0386 (15)	0.0379 (15)	−0.0181 (12)	−0.0022 (12)	−0.0113 (12)
C2	0.0382 (14)	0.0316 (14)	0.0398 (15)	−0.0117 (11)	−0.0041 (11)	−0.0105 (11)
C3	0.0416 (15)	0.0407 (15)	0.0462 (16)	−0.0164 (13)	−0.0063 (12)	−0.0123 (13)
C4	0.0419 (16)	0.0372 (15)	0.0593 (19)	−0.0181 (13)	0.0002 (13)	−0.0131 (14)
C5	0.0498 (17)	0.0399 (16)	0.0483 (17)	−0.0164 (14)	0.0071 (14)	−0.0075 (13)
C6	0.0486 (17)	0.0403 (16)	0.0373 (15)	−0.0116 (13)	−0.0008 (12)	−0.0103 (12)
C7	0.0403 (15)	0.0327 (14)	0.0400 (15)	−0.0114 (12)	−0.0035 (12)	−0.0125 (12)
C8	0.0414 (15)	0.0372 (14)	0.0405 (15)	−0.0154 (12)	−0.0024 (12)	−0.0132 (12)
C9	0.067 (2)	0.060 (2)	0.058 (2)	−0.0173 (18)	−0.0160 (17)	−0.0083 (17)
C10	0.0425 (16)	0.0459 (16)	0.0488 (16)	−0.0203 (13)	−0.0051 (13)	−0.0159 (13)
C11	0.0480 (18)	0.0459 (16)	0.0364 (15)	−0.0246 (14)	−0.0020 (12)	−0.0106 (12)
C12	0.078 (2)	0.0388 (17)	0.073 (2)	−0.0261 (17)	−0.0265 (19)	−0.0036 (16)
C13	0.119 (4)	0.051 (2)	0.111 (4)	−0.024 (2)	0.042 (3)	−0.036 (2)
C14	0.159 (5)	0.084 (3)	0.086 (3)	−0.086 (3)	0.024 (3)	−0.022 (2)

Br—C4	1.904 (3)	C6—C7	1.380 (4)
S—O2	1.492 (2)	C6—H6	0.9300
S—C1	1.759 (3)	C8—C10	1.479 (4)
S—C9	1.790 (4)	C9—H9A	0.9600
O1—C8	1.374 (3)	C9—H9B	0.9600
O1—C7	1.375 (3)	C9—H9C	0.9600
O3—C11	1.331 (3)	C10—C11	1.506 (4)
O3—C12	1.471 (4)	C10—H10A	0.9700
O4—C11	1.193 (3)	C10—H10B	0.9700
C1—C8	1.352 (4)	C12—C13	1.483 (5)
C1—C2	1.445 (4)	C12—C14	1.513 (6)
C2—C7	1.392 (4)	C12—H12	0.9800
C2—C3	1.394 (4)	C13—H13A	0.9600
C3—C4	1.376 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.387 (4)	C14—H14A	0.9600
C5—C6	1.378 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O2—S—C1	107.21 (13)	H9A—C9—H9B	109.5
O2—S—C9	106.82 (16)	S—C9—H9C	109.5
C1—S—C9	98.00 (15)	H9A—C9—H9C	109.5
C8—O1—C7	106.32 (19)	H9B—C9—H9C	109.5
C11—O3—C12	118.0 (2)	C8—C10—C11	113.5 (2)
C8—C1—C2	107.3 (2)	C8—C10—H10A	108.9
C8—C1—S	123.7 (2)	C11—C10—H10A	108.9
C2—C1—S	129.0 (2)	C8—C10—H10B	108.9
C7—C2—C3	119.5 (2)	C11—C10—H10B	108.9
C7—C2—C1	104.7 (2)	H10A—C10—H10B	107.7
C3—C2—C1	135.9 (2)	O4—C11—O3	125.0 (3)
C4—C3—C2	116.6 (3)	O4—C11—C10	125.3 (3)
C4—C3—H3	121.7	O3—C11—C10	109.6 (2)
C2—C3—H3	121.7	O3—C12—C13	108.1 (3)
C3—C4—C5	123.6 (3)	O3—C12—C14	105.3 (3)
C3—C4—Br	118.0 (2)	C13—C12—C14	110.8 (3)
C5—C4—Br	118.4 (2)	O3—C12—H12	110.8
C6—C5—C4	120.2 (3)	C13—C12—H12	110.8
C6—C5—H5	119.9	C14—C12—H12	110.8
C4—C5—H5	119.9	C12—C13—H13A	109.5
C5—C6—C7	116.6 (3)	C12—C13—H13B	109.5
C5—C6—H6	121.7	H13A—C13—H13B	109.5
C7—C6—H6	121.7	C12—C13—H13C	109.5
O1—C7—C6	125.7 (2)	H13A—C13—H13C	109.5
O1—C7—C2	110.7 (2)	H13B—C13—H13C	109.5
C6—C7—C2	123.6 (3)	C12—C14—H14A	109.5
C1—C8—O1	111.0 (2)	C12—C14—H14B	109.5
C1—C8—C10	132.5 (3)	H14A—C14—H14B	109.5
O1—C8—C10	116.5 (2)	C12—C14—H14C	109.5
S—C9—H9A	109.5	H14A—C14—H14C	109.5
S—C9—H9B	109.5	H14B—C14—H14C	109.5
O2—S—C1—C8	−134.2 (2)	C3—C2—C7—O1	−179.9 (2)
C9—S—C1—C8	115.3 (3)	C1—C2—C7—O1	−1.4 (3)
O2—S—C1—C2	41.9 (3)	C3—C2—C7—C6	0.1 (4)
C9—S—C1—C2	−68.5 (3)	C1—C2—C7—C6	178.5 (3)
C8—C1—C2—C7	0.5 (3)	C2—C1—C8—O1	0.7 (3)
S—C1—C2—C7	−176.2 (2)	S—C1—C8—O1	177.55 (18)
C8—C1—C2—C3	178.5 (3)	C2—C1—C8—C10	178.8 (3)
S—C1—C2—C3	1.8 (5)	S—C1—C8—C10	−4.3 (5)
C7—C2—C3—C4	0.6 (4)	C7—O1—C8—C1	−1.5 (3)
C1—C2—C3—C4	−177.2 (3)	C7—O1—C8—C10	180.0 (2)
C2—C3—C4—C5	−0.7 (4)	C1—C8—C10—C11	−76.4 (4)
C2—C3—C4—Br	177.7 (2)	O1—C8—C10—C11	101.6 (3)
C3—C4—C5—C6	0.1 (5)	C12—O3—C11—O4	−4.5 (4)
Br—C4—C5—C6	−178.3 (2)	C12—O3—C11—C10	178.3 (3)
C4—C5—C6—C7	0.6 (4)	C8—C10—C11—O4	12.3 (4)
C8—O1—C7—C6	−178.1 (3)	C8—C10—C11—O3	−170.5 (2)
C8—O1—C7—C2	1.8 (3)	C11—O3—C12—C13	−89.9 (4)
C5—C6—C7—O1	179.3 (3)	C11—O3—C12—C14	151.6 (3)
C5—C6—C7—C2	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.50	3.392 (4)	160
C10—H10B···O2ii	0.97	2.40	3.365 (4)	173
C13—H13C···Cgiii	0.96	2.78	3.526 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.50	3.392 (4)	160
C10—H10B⋯O2ii	0.97	2.40	3.365 (4)	173
C13—H13C⋯Cgiii	0.96	2.78	3.526 (4)	136

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C2–C7 benzene ring.