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

In the title compound, C(14)H(15)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment which is essentially planar with a mean deviation of 0.008 (1) Å from its least-squares plane. The crystal structure stabilized by three different inter-molecular non-classical C-H⋯O hydrogen bonds. The crystal structure also exhibits aromatic π-π inter-actions between the benzene rings of adjacent benzofuran ring systems [centroid-centroid distance = 3.688 (2) Å].

Related literature

For the crystal structures of similar alkyl 2-(5-fluoro-3-methyl­sulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2009 ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶).

Experimental

Crystal data

C14H15FO4S

M = 298.32

Monoclinic,

a = 11.6332 (6) Å

b = 14.9522 (7) Å

c = 8.2333 (4) Å

β = 102.277 (1)°

V = 1399.36 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.25 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.940, T max = 0.961

12229 measured reflections

3173 independent reflections

2476 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.09

3173 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.39 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/S1600536809037003/bq2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037003/bq2158Isup2.hkl

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

C14H15FO4S	F(000) = 624
Mr = 298.32	Dx = 1.416 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5216 reflections
a = 11.6332 (6) Å	θ = 2.3–27.4°
b = 14.9522 (7) Å	µ = 0.25 mm−1
c = 8.2333 (4) Å	T = 173 K
β = 102.277 (1)°	Block, colorless
V = 1399.36 (12) Å3	0.25 × 0.20 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	3173 independent reflections
Radiation source: fine-focus sealed tube	2476 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −19→19
Tmin = 0.940, Tmax = 0.961	l = −10→10
12229 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.5417P] where P = (Fo2 + 2Fc2)/3
3173 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.39 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
S	0.16889 (4)	0.32823 (3)	0.59899 (5)	0.02546 (13)
F	0.53377 (11)	0.32123 (8)	0.19202 (14)	0.0427 (3)
O1	0.47612 (10)	0.43326 (8)	0.79555 (14)	0.0242 (3)
O2	0.19830 (10)	0.54133 (8)	1.03615 (14)	0.0264 (3)
O3	0.17889 (11)	0.53806 (9)	0.75830 (15)	0.0329 (3)
O4	0.17181 (12)	0.23235 (9)	0.54858 (18)	0.0393 (3)
C1	0.31410 (14)	0.36896 (11)	0.6411 (2)	0.0222 (3)
C2	0.40529 (14)	0.36553 (11)	0.5455 (2)	0.0222 (3)
C3	0.41420 (16)	0.33514 (12)	0.3875 (2)	0.0264 (4)
H3	0.3516	0.3078	0.3155	0.032*
C4	0.52168 (16)	0.34834 (12)	0.3458 (2)	0.0289 (4)
C5	0.61801 (16)	0.38849 (12)	0.4473 (2)	0.0284 (4)
H5	0.6880	0.3950	0.4111	0.034*
C6	0.60937 (14)	0.41885 (12)	0.6032 (2)	0.0257 (4)
H6	0.6722	0.4464	0.6744	0.031*
C7	0.50247 (14)	0.40604 (11)	0.6470 (2)	0.0224 (3)
C8	0.36106 (14)	0.40933 (11)	0.7872 (2)	0.0229 (4)
C9	0.31082 (15)	0.43478 (12)	0.9330 (2)	0.0252 (4)
H9A	0.3743	0.4524	1.0239	0.030*
H9B	0.2725	0.3831	0.9689	0.030*
C10	0.22306 (14)	0.51050 (12)	0.8949 (2)	0.0234 (4)
C11	0.11677 (16)	0.61749 (12)	1.0234 (2)	0.0298 (4)
H11	0.0555	0.6121	0.9218	0.036*
C12	0.06204 (17)	0.61224 (13)	1.1728 (2)	0.0340 (4)
H12A	0.0191	0.5572	1.1699	0.051*
H12B	0.0094	0.6618	1.1718	0.051*
H12C	0.1226	0.6143	1.2721	0.051*
C13	0.1857 (2)	0.70278 (14)	1.0176 (3)	0.0504 (6)
H13A	0.2183	0.7028	0.9199	0.076*
H13B	0.2482	0.7064	1.1146	0.076*
H13C	0.1344	0.7533	1.0147	0.076*
C14	0.11297 (18)	0.39058 (15)	0.4135 (2)	0.0397 (5)
H14A	0.1529	0.3725	0.3282	0.060*
H14B	0.1258	0.4532	0.4356	0.060*
H14C	0.0302	0.3794	0.3773	0.060*

	U11	U22	U33	U12	U13	U23
S	0.0205 (2)	0.0281 (2)	0.0274 (2)	−0.00173 (17)	0.00402 (16)	−0.00285 (18)
F	0.0481 (7)	0.0526 (8)	0.0320 (6)	−0.0002 (6)	0.0189 (5)	−0.0125 (5)
O1	0.0211 (6)	0.0286 (6)	0.0221 (6)	−0.0011 (5)	0.0031 (5)	−0.0028 (5)
O2	0.0283 (6)	0.0295 (7)	0.0213 (6)	0.0066 (5)	0.0046 (5)	−0.0010 (5)
O3	0.0323 (7)	0.0439 (8)	0.0226 (6)	0.0096 (6)	0.0062 (5)	0.0042 (6)
O4	0.0339 (7)	0.0291 (7)	0.0529 (9)	−0.0065 (6)	0.0048 (6)	−0.0116 (6)
C1	0.0203 (8)	0.0202 (8)	0.0253 (8)	0.0012 (6)	0.0030 (6)	0.0000 (7)
C2	0.0222 (8)	0.0196 (8)	0.0241 (8)	0.0022 (6)	0.0033 (6)	0.0002 (7)
C3	0.0281 (9)	0.0243 (9)	0.0258 (8)	0.0002 (7)	0.0037 (7)	−0.0046 (7)
C4	0.0359 (10)	0.0275 (9)	0.0254 (9)	0.0052 (8)	0.0113 (8)	−0.0022 (7)
C5	0.0256 (9)	0.0279 (9)	0.0339 (9)	0.0044 (7)	0.0108 (7)	0.0028 (8)
C6	0.0200 (8)	0.0263 (9)	0.0298 (9)	0.0015 (7)	0.0029 (7)	0.0005 (7)
C7	0.0241 (8)	0.0213 (8)	0.0217 (8)	0.0028 (7)	0.0042 (6)	0.0000 (6)
C8	0.0198 (8)	0.0233 (8)	0.0251 (8)	0.0009 (6)	0.0037 (6)	0.0026 (7)
C9	0.0263 (9)	0.0283 (9)	0.0205 (8)	0.0009 (7)	0.0037 (7)	0.0005 (7)
C10	0.0215 (8)	0.0274 (9)	0.0214 (8)	−0.0046 (7)	0.0052 (6)	−0.0015 (7)
C11	0.0299 (9)	0.0320 (10)	0.0269 (9)	0.0098 (8)	0.0049 (7)	0.0021 (8)
C12	0.0301 (9)	0.0382 (11)	0.0359 (10)	0.0079 (8)	0.0119 (8)	0.0019 (9)
C13	0.0648 (15)	0.0322 (11)	0.0636 (15)	0.0043 (10)	0.0345 (13)	0.0087 (11)
C14	0.0302 (10)	0.0517 (13)	0.0329 (10)	0.0040 (9)	−0.0030 (8)	0.0067 (9)

S—O4	1.4949 (14)	C6—C7	1.380 (2)
S—C1	1.7595 (17)	C6—H6	0.9300
S—C14	1.7894 (19)	C8—C9	1.491 (2)
F—C4	1.365 (2)	C9—C10	1.512 (2)
O1—C8	1.3731 (19)	C9—H9A	0.9700
O1—C7	1.384 (2)	C9—H9B	0.9700
O2—C10	1.338 (2)	C11—C12	1.502 (2)
O2—C11	1.472 (2)	C11—C13	1.513 (3)
O3—C10	1.205 (2)	C11—H11	0.9800
C1—C8	1.353 (2)	C12—H12A	0.9600
C1—C2	1.450 (2)	C12—H12B	0.9600
C2—C7	1.394 (2)	C12—H12C	0.9600
C2—C3	1.402 (2)	C13—H13A	0.9600
C3—C4	1.380 (2)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.384 (3)	C14—H14A	0.9600
C5—C6	1.385 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O4—S—C1	108.00 (8)	C10—C9—H9A	109.0
O4—S—C14	106.75 (10)	C8—C9—H9B	109.0
C1—S—C14	98.47 (9)	C10—C9—H9B	109.0
C8—O1—C7	106.03 (12)	H9A—C9—H9B	107.8
C10—O2—C11	117.35 (13)	O3—C10—O2	124.43 (16)
C8—C1—C2	107.15 (14)	O3—C10—C9	125.76 (15)
C8—C1—S	121.23 (13)	O2—C10—C9	109.79 (14)
C2—C1—S	131.57 (13)	O2—C11—C12	106.27 (14)
C7—C2—C3	119.14 (15)	O2—C11—C13	108.45 (16)
C7—C2—C1	104.64 (14)	C12—C11—C13	112.95 (17)
C3—C2—C1	136.21 (16)	O2—C11—H11	109.7
C4—C3—C2	115.75 (16)	C12—C11—H11	109.7
C4—C3—H3	122.1	C13—C11—H11	109.7
C2—C3—H3	122.1	C11—C12—H12A	109.5
F—C4—C3	117.80 (16)	C11—C12—H12B	109.5
F—C4—C5	117.32 (16)	H12A—C12—H12B	109.5
C3—C4—C5	124.87 (16)	C11—C12—H12C	109.5
C4—C5—C6	119.52 (16)	H12A—C12—H12C	109.5
C4—C5—H5	120.2	H12B—C12—H12C	109.5
C6—C5—H5	120.2	C11—C13—H13A	109.5
C7—C6—C5	116.35 (16)	C11—C13—H13B	109.5
C7—C6—H6	121.8	H13A—C13—H13B	109.5
C5—C6—H6	121.8	C11—C13—H13C	109.5
C6—C7—O1	124.87 (15)	H13A—C13—H13C	109.5
C6—C7—C2	124.37 (16)	H13B—C13—H13C	109.5
O1—C7—C2	110.75 (14)	S—C14—H14A	109.5
C1—C8—O1	111.43 (14)	S—C14—H14B	109.5
C1—C8—C9	132.54 (16)	H14A—C14—H14B	109.5
O1—C8—C9	115.98 (14)	S—C14—H14C	109.5
C8—C9—C10	112.79 (14)	H14A—C14—H14C	109.5
C8—C9—H9A	109.0	H14B—C14—H14C	109.5
O4—S—C1—C8	−126.67 (15)	C3—C2—C7—C6	0.0 (3)
C14—S—C1—C8	122.54 (15)	C1—C2—C7—C6	−178.66 (16)
O4—S—C1—C2	50.55 (18)	C3—C2—C7—O1	178.64 (14)
C14—S—C1—C2	−60.23 (18)	C1—C2—C7—O1	0.01 (18)
C8—C1—C2—C7	−0.17 (18)	C2—C1—C8—O1	0.27 (19)
S—C1—C2—C7	−177.69 (14)	S—C1—C8—O1	178.10 (11)
C8—C1—C2—C3	−178.44 (19)	C2—C1—C8—C9	177.57 (17)
S—C1—C2—C3	4.0 (3)	S—C1—C8—C9	−4.6 (3)
C7—C2—C3—C4	0.1 (2)	C7—O1—C8—C1	−0.26 (18)
C1—C2—C3—C4	178.20 (18)	C7—O1—C8—C9	−178.05 (14)
C2—C3—C4—F	−178.87 (15)	C1—C8—C9—C10	−69.4 (2)
C2—C3—C4—C5	0.0 (3)	O1—C8—C9—C10	107.82 (16)
F—C4—C5—C6	178.67 (16)	C11—O2—C10—O3	−3.7 (2)
C3—C4—C5—C6	−0.2 (3)	C11—O2—C10—C9	178.11 (14)
C4—C5—C6—C7	0.3 (3)	C8—C9—C10—O3	13.5 (2)
C5—C6—C7—O1	−178.66 (15)	C8—C9—C10—O2	−168.35 (14)
C5—C6—C7—C2	−0.2 (3)	C10—O2—C11—C12	154.84 (15)
C8—O1—C7—C6	178.81 (16)	C10—O2—C11—C13	−83.45 (19)
C8—O1—C7—C2	0.15 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3i	0.93	2.50	3.370 (2)	155
C6—H6···O2ii	0.93	2.54	3.369 (2)	149
C9—H9B···O4iii	0.97	2.26	3.228 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3i	0.93	2.50	3.370 (2)	155
C6—H6⋯O2ii	0.93	2.54	3.369 (2)	149
C9—H9B⋯O4iii	0.97	2.26	3.228 (2)	176

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