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

In the title compound, C(14)H(15)ClO(4)S, the S atom has a distorted trigonal-pyramidal coordination. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the benzofuran ring system. The crystal structure is stabilized by intermolecular aromatic π-π interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 4.057 (3) Å], and by C-H⋯π interactions between a methyl H atom and the benzene ring of an adjacent molecule.

Related literature

For the crystal structures of similar compounds, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C14H15ClO4S

M = 314.77

Triclinic,

a = 7.8824 (6) Å

b = 10.0352 (8) Å

c = 10.9004 (8) Å

α = 69.254 (1)°

β = 81.662 (1)°

γ = 67.703 (1)°

V = 745.98 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 298 (2) K

0.50 × 0.40 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.816, T max = 0.939

5508 measured reflections

2602 independent reflections

2354 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.124

S = 1.12

2602 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.29 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/S1600536808039937/ng2521sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039937/ng2521Isup2.hkl

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

C14H15ClO4S	Z = 2
Mr = 314.77	F(000) = 328
Triclinic, P1	Dx = 1.401 Mg m−3
Hall symbol: -P 1	Melting point = 422–423 K
a = 7.8824 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0352 (8) Å	Cell parameters from 4167 reflections
c = 10.9004 (8) Å	θ = 2.5–28.3°
α = 69.254 (1)°	µ = 0.41 mm−1
β = 81.662 (1)°	T = 298 K
γ = 67.703 (1)°	Plate, colorless
V = 745.98 (10) Å3	0.50 × 0.40 × 0.15 mm

Bruker SMART CCD diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	2354 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.5°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→11
Tmin = 0.816, Tmax = 0.939	l = −12→12
5508 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.125	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.4971P] where P = (Fo2 + 2Fc2)/3
2602 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.29 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	0.74726 (9)	0.60225 (8)	0.54010 (6)	0.0480 (2)
Cl	0.29574 (12)	0.21443 (10)	0.87346 (10)	0.0816 (3)
O1	0.8348 (2)	0.45903 (19)	0.91914 (16)	0.0435 (4)
O2	0.7488 (3)	0.4832 (3)	0.48756 (19)	0.0637 (6)
O3	1.0254 (3)	0.8446 (2)	0.7284 (2)	0.0582 (5)
O4	0.7414 (3)	0.8557 (2)	0.7070 (2)	0.0674 (6)
C1	0.7475 (3)	0.5246 (3)	0.7125 (2)	0.0393 (5)
C2	0.6447 (3)	0.4337 (3)	0.7973 (2)	0.0378 (5)
C3	0.5137 (3)	0.3799 (3)	0.7797 (3)	0.0462 (6)
H3	0.4686	0.4043	0.6972	0.055*
C4	0.4550 (4)	0.2888 (3)	0.8910 (3)	0.0510 (7)
C5	0.5171 (4)	0.2520 (3)	1.0159 (3)	0.0544 (7)
H5	0.4720	0.1905	1.0878	0.065*
C6	0.6450 (4)	0.3061 (3)	1.0341 (3)	0.0486 (6)
H6	0.6878	0.2832	1.1170	0.058*
C7	0.7062 (3)	0.3959 (3)	0.9229 (2)	0.0408 (5)
C8	0.8579 (3)	0.5352 (3)	0.7894 (2)	0.0409 (5)
C9	0.9910 (3)	0.6147 (3)	0.7601 (3)	0.0455 (6)
H9A	1.0667	0.5947	0.6856	0.055*
H9B	1.0708	0.5735	0.8347	0.055*
C10	0.9005 (4)	0.7845 (3)	0.7302 (2)	0.0437 (6)
C11	0.9615 (5)	1.0095 (3)	0.7059 (4)	0.0697 (9)
H11	0.8528	1.0642	0.6503	0.084*
C12	1.1212 (8)	1.0569 (5)	0.6388 (5)	0.1199 (18)
H12A	1.0856	1.1656	0.6142	0.180*
H12B	1.1570	1.0267	0.5619	0.180*
H12C	1.2226	1.0085	0.6979	0.180*
C13	0.9213 (8)	1.0315 (4)	0.8347 (5)	0.1195 (19)
H13A	0.8255	0.9938	0.8777	0.179*
H13B	0.8825	1.1381	0.8233	0.179*
H13C	1.0296	0.9770	0.8872	0.179*
C14	0.5183 (4)	0.7385 (4)	0.5211 (3)	0.0671 (8)
H14A	0.4977	0.7998	0.4304	0.101*
H14B	0.5018	0.8027	0.5728	0.101*
H14C	0.4327	0.6861	0.5499	0.101*

	U11	U22	U33	U12	U13	U23
S	0.0489 (4)	0.0589 (4)	0.0385 (4)	−0.0261 (3)	−0.0038 (3)	−0.0100 (3)
Cl	0.0694 (5)	0.0748 (6)	0.1092 (7)	−0.0480 (5)	−0.0073 (5)	−0.0132 (5)
O1	0.0486 (10)	0.0464 (9)	0.0398 (9)	−0.0184 (8)	−0.0057 (7)	−0.0154 (7)
O2	0.0685 (13)	0.0804 (14)	0.0515 (12)	−0.0250 (11)	−0.0047 (9)	−0.0322 (11)
O3	0.0622 (12)	0.0429 (10)	0.0740 (13)	−0.0240 (9)	−0.0176 (10)	−0.0120 (9)
O4	0.0501 (12)	0.0510 (11)	0.0946 (16)	−0.0161 (10)	−0.0120 (11)	−0.0139 (11)
C1	0.0427 (13)	0.0388 (12)	0.0383 (13)	−0.0157 (10)	−0.0035 (10)	−0.0124 (10)
C2	0.0390 (12)	0.0345 (12)	0.0401 (13)	−0.0113 (10)	−0.0023 (10)	−0.0134 (10)
C3	0.0438 (14)	0.0438 (14)	0.0532 (15)	−0.0174 (11)	−0.0051 (11)	−0.0146 (12)
C4	0.0428 (14)	0.0421 (14)	0.0682 (18)	−0.0179 (11)	−0.0002 (12)	−0.0153 (13)
C5	0.0541 (16)	0.0437 (14)	0.0553 (16)	−0.0172 (13)	0.0089 (13)	−0.0084 (12)
C6	0.0509 (15)	0.0428 (14)	0.0432 (14)	−0.0102 (12)	0.0007 (11)	−0.0111 (11)
C7	0.0404 (13)	0.0353 (12)	0.0457 (13)	−0.0099 (10)	−0.0016 (10)	−0.0155 (10)
C8	0.0430 (13)	0.0374 (12)	0.0434 (13)	−0.0130 (10)	−0.0041 (10)	−0.0145 (10)
C9	0.0443 (14)	0.0476 (14)	0.0509 (15)	−0.0201 (11)	−0.0050 (11)	−0.0176 (12)
C10	0.0484 (15)	0.0482 (14)	0.0384 (13)	−0.0223 (12)	−0.0030 (11)	−0.0121 (11)
C11	0.082 (2)	0.0406 (15)	0.085 (2)	−0.0242 (15)	−0.0304 (18)	−0.0055 (15)
C12	0.181 (5)	0.083 (3)	0.115 (4)	−0.086 (3)	0.035 (3)	−0.027 (3)
C13	0.159 (5)	0.056 (2)	0.121 (4)	−0.018 (3)	0.045 (3)	−0.042 (2)
C14	0.0657 (19)	0.0586 (18)	0.0640 (19)	−0.0112 (15)	−0.0194 (15)	−0.0095 (15)

S—O2	1.493 (2)	C6—C7	1.378 (4)
S—C1	1.761 (2)	C6—H6	0.9300
S—C14	1.790 (3)	C8—C9	1.482 (3)
Cl—C4	1.747 (3)	C9—C10	1.506 (4)
O1—C8	1.372 (3)	C9—H9A	0.9700
O1—C7	1.374 (3)	C9—H9B	0.9700
O3—C10	1.331 (3)	C11—C13	1.469 (6)
O3—C11	1.472 (3)	C11—C12	1.513 (6)
O4—C10	1.196 (3)	C11—H11	0.9800
C1—C8	1.348 (3)	C12—H12A	0.9600
C1—C2	1.445 (3)	C12—H12B	0.9600
C2—C7	1.392 (3)	C12—H12C	0.9600
C2—C3	1.396 (3)	C13—H13A	0.9600
C3—C4	1.376 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.390 (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	107.34 (12)	C10—C9—H9A	109.0
O2—S—C14	106.36 (14)	C8—C9—H9B	109.0
C1—S—C14	98.16 (14)	C10—C9—H9B	109.0
C8—O1—C7	106.25 (18)	H9A—C9—H9B	107.8
C10—O3—C11	117.8 (2)	O4—C10—O3	124.9 (2)
C8—C1—C2	107.3 (2)	O4—C10—C9	125.3 (2)
C8—C1—S	123.59 (19)	O3—C10—C9	109.8 (2)
C2—C1—S	129.04 (18)	C13—C11—O3	107.5 (3)
C7—C2—C3	119.7 (2)	C13—C11—C12	111.2 (4)
C7—C2—C1	104.6 (2)	O3—C11—C12	104.8 (3)
C3—C2—C1	135.7 (2)	C13—C11—H11	111.0
C4—C3—C2	116.3 (2)	O3—C11—H11	111.0
C4—C3—H3	121.8	C12—C11—H11	111.0
C2—C3—H3	121.8	C11—C12—H12A	109.5
C3—C4—C5	123.4 (2)	C11—C12—H12B	109.5
C3—C4—Cl	118.1 (2)	H12A—C12—H12B	109.5
C5—C4—Cl	118.5 (2)	C11—C12—H12C	109.5
C6—C5—C4	120.5 (2)	H12A—C12—H12C	109.5
C6—C5—H5	119.8	H12B—C12—H12C	109.5
C4—C5—H5	119.8	C11—C13—H13A	109.5
C5—C6—C7	116.4 (2)	C11—C13—H13B	109.5
C5—C6—H6	121.8	H13A—C13—H13B	109.5
C7—C6—H6	121.8	C11—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 (2)	S—C14—H14A	109.5
C1—C8—O1	111.2 (2)	S—C14—H14B	109.5
C1—C8—C9	132.5 (2)	H14A—C14—H14B	109.5
O1—C8—C9	116.3 (2)	S—C14—H14C	109.5
C8—C9—C10	113.1 (2)	H14A—C14—H14C	109.5
C8—C9—H9A	109.0	H14B—C14—H14C	109.5
O2—S—C1—C8	133.8 (2)	C3—C2—C7—O1	179.7 (2)
C14—S—C1—C8	−116.2 (2)	C1—C2—C7—O1	0.9 (3)
O2—S—C1—C2	−42.4 (3)	C3—C2—C7—C6	0.1 (4)
C14—S—C1—C2	67.7 (3)	C1—C2—C7—C6	−178.6 (2)
C8—C1—C2—C7	−0.3 (3)	C2—C1—C8—O1	−0.5 (3)
S—C1—C2—C7	176.39 (19)	S—C1—C8—O1	−177.37 (16)
C8—C1—C2—C3	−178.7 (3)	C2—C1—C8—C9	−178.7 (2)
S—C1—C2—C3	−2.1 (4)	S—C1—C8—C9	4.4 (4)
C7—C2—C3—C4	−0.9 (4)	C7—O1—C8—C1	1.1 (3)
C1—C2—C3—C4	177.4 (3)	C7—O1—C8—C9	179.6 (2)
C2—C3—C4—C5	1.1 (4)	C1—C8—C9—C10	75.3 (4)
C2—C3—C4—Cl	−178.30 (19)	O1—C8—C9—C10	−102.9 (2)
C3—C4—C5—C6	−0.5 (4)	C11—O3—C10—O4	4.8 (4)
Cl—C4—C5—C6	178.9 (2)	C11—O3—C10—C9	−177.6 (2)
C4—C5—C6—C7	−0.3 (4)	C8—C9—C10—O4	−13.6 (4)
C8—O1—C7—C6	178.3 (2)	C8—C9—C10—O3	168.8 (2)
C8—O1—C7—C2	−1.2 (3)	C10—O3—C11—C13	91.0 (4)
C5—C6—C7—O1	−179.0 (2)	C10—O3—C11—C12	−150.6 (3)
C5—C6—C7—C2	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···Cgi	0.96	2.78	3.515 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯Cgi	0.96	2.78	3.515 (3)	134

Symmetry code: (i) . Cg is the centroid of the C2–C7 benzene ring.