5-Chloro-3-ethyl-sulfinyl-7-methyl-2-(4-methyl-phen-yl)-1-benzo-furan.

In the title compound, C18H17ClO2S, the dihedral angle between the mean planes of the benzo-furan ring system and the methyl-phenyl ring is 14.50 (4)°. The centroid-centroid distances between the benzene and the methyl-phenyl rings are 3.827 (2) and 3.741 (2) Å, while the centroid-centroid distance between the furan and methyl-phenyl rings is 3.843 (2) Å. These distances indicate π-π inter-actions; on the other hand, the inter-planar angles between the benzene and methyl-phenyl rings, and between the furan and methyl-phenyl rings are 13.89 (4) and 15.53 (4)°, respectively. In the crystal, the mol-ecules stack along the a-axis direction.

Related literature

For background information about related compounds and their crystal structures, see Choi et al. (2010a ▶,b ▶). For π–π stacking in metal complexes with aromatic nitro­gen ligands, see: Janiak (2000 ▶).

Experimental

Crystal data

C18H17ClO2S

M = 332.83

Triclinic,

a = 7.3638 (5) Å

b = 10.2524 (6) Å

c = 11.8335 (7) Å

α = 68.949 (3)°

β = 89.362 (3)°

γ = 71.460 (3)°

V = 785.11 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 173 K

0.46 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.691, T max = 0.746

13937 measured reflections

3759 independent reflections

3348 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.100

S = 1.06

3759 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005601/fb2296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005601/fb2296Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005601/fb2296Isup3.cml

CCDC reference: 991267

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H17ClO2S	Z = 2
Mr = 332.83	F(000) = 348
Triclinic, P1	Dx = 1.408 Mg m−3
Hall symbol: -P 1	Melting point = 392–393 K
a = 7.3638 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2524 (6) Å	Cell parameters from 8286 reflections
c = 11.8335 (7) Å	θ = 2.3–28.4°
α = 68.949 (3)°	µ = 0.38 mm−1
β = 89.362 (3)°	T = 173 K
γ = 71.460 (3)°	Block, colourless
V = 785.11 (8) Å3	0.46 × 0.37 × 0.33 mm

Bruker SMART APEXII CCD diffractometer	3759 independent reflections
Radiation source: rotating anode	3348 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.0°, θmin = 2.3°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.691, Tmax = 0.746	l = −15→15
13937 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2412P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3759 reflections	Δρmax = 0.31 e Å−3
203 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (2)

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
Cl1	0.02297 (6)	0.70926 (4)	−0.07104 (3)	0.03932 (13)
S1	0.36271 (5)	0.19161 (4)	0.40911 (3)	0.02784 (11)
O1	0.19351 (14)	0.58273 (10)	0.44275 (8)	0.0265 (2)
O2	0.21419 (17)	0.18248 (12)	0.32973 (11)	0.0411 (3)
C1	0.29375 (19)	0.37881 (14)	0.39556 (12)	0.0251 (3)
C2	0.20899 (19)	0.50599 (14)	0.28375 (12)	0.0248 (3)
C3	0.1735 (2)	0.52797 (15)	0.16126 (13)	0.0279 (3)
H3	0.2128	0.4481	0.1335	0.033*
C4	0.0781 (2)	0.67216 (16)	0.08294 (13)	0.0290 (3)
C5	0.0153 (2)	0.79189 (15)	0.12135 (13)	0.0298 (3)
H5	−0.0515	0.8884	0.0634	0.036*
C7	0.14795 (19)	0.62695 (15)	0.31933 (12)	0.0251 (3)
C6	0.0489 (2)	0.77201 (15)	0.24256 (13)	0.0273 (3)
C8	0.28210 (19)	0.43087 (14)	0.48790 (12)	0.0249 (3)
C9	−0.0186 (2)	0.89610 (16)	0.28858 (15)	0.0343 (3)
H9A	−0.1057	0.9849	0.2243	0.052*
H9B	0.0929	0.9177	0.3116	0.052*
H9C	−0.0870	0.8668	0.3599	0.052*
C10	0.3426 (2)	0.36521 (15)	0.61893 (12)	0.0262 (3)
C11	0.2685 (2)	0.44896 (16)	0.69082 (13)	0.0299 (3)
H11	0.1763	0.5457	0.6543	0.036*
C12	0.3291 (2)	0.39130 (18)	0.81450 (14)	0.0343 (3)
H12	0.2787	0.4499	0.8615	0.041*
C13	0.4619 (2)	0.24959 (18)	0.87129 (13)	0.0339 (3)
C14	0.5333 (2)	0.16600 (17)	0.80041 (14)	0.0338 (3)
H14	0.6229	0.0683	0.8379	0.041*
C15	0.4761 (2)	0.22262 (16)	0.67607 (13)	0.0297 (3)
H15	0.5282	0.1639	0.6294	0.036*
C16	0.5257 (3)	0.1898 (2)	1.00639 (14)	0.0458 (4)
H16A	0.6069	0.0852	1.0331	0.069*
H16B	0.4121	0.1986	1.0509	0.069*
H16C	0.5994	0.2468	1.0229	0.069*
C17	0.5744 (2)	0.18473 (17)	0.32871 (14)	0.0336 (3)
H17A	0.6062	0.1004	0.3012	0.040*
H17B	0.5467	0.2772	0.2556	0.040*
C18	0.7460 (2)	0.16692 (17)	0.40993 (15)	0.0363 (3)
H18A	0.7127	0.2480	0.4401	0.054*
H18B	0.8561	0.1696	0.3630	0.054*
H18C	0.7798	0.0717	0.4791	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.0511 (3)	0.0362 (2)	0.02820 (19)	−0.01466 (18)	−0.00402 (16)	−0.00909 (15)
S1	0.0307 (2)	0.02136 (17)	0.03107 (19)	−0.00773 (14)	0.00090 (14)	−0.01020 (13)
O1	0.0277 (5)	0.0223 (5)	0.0278 (5)	−0.0054 (4)	0.0023 (4)	−0.0101 (4)
O2	0.0422 (7)	0.0359 (6)	0.0484 (7)	−0.0158 (5)	−0.0071 (5)	−0.0166 (5)
C1	0.0235 (6)	0.0218 (6)	0.0280 (6)	−0.0057 (5)	0.0031 (5)	−0.0089 (5)
C2	0.0210 (6)	0.0230 (6)	0.0296 (7)	−0.0065 (5)	0.0029 (5)	−0.0098 (5)
C3	0.0274 (7)	0.0263 (6)	0.0304 (7)	−0.0080 (5)	0.0016 (5)	−0.0119 (5)
C4	0.0283 (7)	0.0304 (7)	0.0275 (7)	−0.0106 (6)	−0.0006 (5)	−0.0092 (5)
C5	0.0274 (7)	0.0240 (6)	0.0334 (7)	−0.0067 (5)	−0.0010 (6)	−0.0070 (5)
C7	0.0225 (6)	0.0241 (6)	0.0280 (6)	−0.0068 (5)	0.0017 (5)	−0.0100 (5)
C6	0.0226 (6)	0.0236 (6)	0.0338 (7)	−0.0059 (5)	0.0019 (5)	−0.0103 (5)
C8	0.0222 (6)	0.0216 (6)	0.0304 (7)	−0.0068 (5)	0.0041 (5)	−0.0098 (5)
C9	0.0339 (8)	0.0237 (7)	0.0410 (8)	−0.0028 (6)	0.0020 (6)	−0.0130 (6)
C10	0.0258 (7)	0.0275 (6)	0.0275 (6)	−0.0121 (5)	0.0056 (5)	−0.0102 (5)
C11	0.0320 (7)	0.0292 (7)	0.0318 (7)	−0.0132 (6)	0.0080 (6)	−0.0129 (6)
C12	0.0398 (8)	0.0396 (8)	0.0318 (7)	−0.0199 (7)	0.0115 (6)	−0.0173 (6)
C13	0.0327 (8)	0.0441 (8)	0.0278 (7)	−0.0205 (7)	0.0064 (6)	−0.0104 (6)
C14	0.0294 (7)	0.0340 (7)	0.0315 (7)	−0.0097 (6)	0.0021 (6)	−0.0058 (6)
C15	0.0270 (7)	0.0313 (7)	0.0304 (7)	−0.0088 (6)	0.0042 (5)	−0.0121 (6)
C16	0.0473 (10)	0.0616 (11)	0.0283 (8)	−0.0238 (9)	0.0054 (7)	−0.0117 (7)
C17	0.0341 (8)	0.0309 (7)	0.0331 (7)	−0.0029 (6)	0.0056 (6)	−0.0160 (6)
C18	0.0332 (8)	0.0325 (7)	0.0451 (9)	−0.0107 (6)	0.0082 (6)	−0.0172 (7)

Cl1—C4	1.7465 (15)	C10—C15	1.397 (2)
S1—O2	1.4962 (12)	C10—C11	1.4054 (19)
S1—C1	1.7686 (13)	C11—C12	1.384 (2)
S1—C17	1.8129 (16)	C11—H11	0.9500
O1—C7	1.3746 (16)	C12—C13	1.389 (2)
O1—C8	1.3782 (15)	C12—H12	0.9500
C1—C8	1.3689 (19)	C13—C14	1.391 (2)
C1—C2	1.4498 (18)	C13—C16	1.510 (2)
C2—C7	1.3905 (18)	C14—C15	1.387 (2)
C2—C3	1.3988 (19)	C14—H14	0.9500
C3—C4	1.3811 (19)	C15—H15	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.401 (2)	C16—H16B	0.9800
C5—C6	1.388 (2)	C16—H16C	0.9800
C5—H5	0.9500	C17—C18	1.519 (2)
C7—C6	1.3868 (18)	C17—H17A	0.9900
C6—C9	1.5006 (19)	C17—H17B	0.9900
C8—C10	1.4597 (19)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800
O2—S1—C1	106.72 (6)	C15—C10—C8	122.50 (13)
O2—S1—C17	106.62 (7)	C11—C10—C8	119.29 (12)
C1—S1—C17	98.27 (7)	C12—C11—C10	120.40 (14)
C7—O1—C8	107.00 (10)	C12—C11—H11	119.8
C8—C1—C2	107.17 (12)	C10—C11—H11	119.8
C8—C1—S1	127.41 (10)	C11—C12—C13	121.40 (14)
C2—C1—S1	124.75 (10)	C11—C12—H12	119.3
C7—C2—C3	119.38 (12)	C13—C12—H12	119.3
C7—C2—C1	104.93 (12)	C12—C13—C14	118.17 (14)
C3—C2—C1	135.63 (13)	C12—C13—C16	120.22 (15)
C4—C3—C2	116.30 (13)	C14—C13—C16	121.61 (15)
C4—C3—H3	121.8	C15—C14—C13	121.24 (14)
C2—C3—H3	121.8	C15—C14—H14	119.4
C3—C4—C5	123.25 (13)	C13—C14—H14	119.4
C3—C4—Cl1	119.41 (11)	C14—C15—C10	120.58 (14)
C5—C4—Cl1	117.29 (11)	C14—C15—H15	119.7
C6—C5—C4	121.19 (13)	C10—C15—H15	119.7
C6—C5—H5	119.4	C13—C16—H16A	109.5
C4—C5—H5	119.4	C13—C16—H16B	109.5
O1—C7—C6	124.11 (12)	H16A—C16—H16B	109.5
O1—C7—C2	110.69 (11)	C13—C16—H16C	109.5
C6—C7—C2	125.17 (13)	H16A—C16—H16C	109.5
C7—C6—C5	114.68 (12)	H16B—C16—H16C	109.5
C7—C6—C9	122.11 (13)	C18—C17—S1	111.08 (10)
C5—C6—C9	123.20 (13)	C18—C17—H17A	109.4
C1—C8—O1	110.19 (12)	S1—C17—H17A	109.4
C1—C8—C10	135.60 (12)	C18—C17—H17B	109.4
O1—C8—C10	114.20 (11)	S1—C17—H17B	109.4
C6—C9—H9A	109.5	H17A—C17—H17B	108.0
C6—C9—H9B	109.5	C17—C18—H18A	109.5
H9A—C9—H9B	109.5	C17—C18—H18B	109.5
C6—C9—H9C	109.5	H18A—C18—H18B	109.5
H9A—C9—H9C	109.5	C17—C18—H18C	109.5
H9B—C9—H9C	109.5	H18A—C18—H18C	109.5
C15—C10—C11	118.19 (13)	H18B—C18—H18C	109.5
O2—S1—C1—C8	131.72 (13)	C4—C5—C6—C7	0.2 (2)
C17—S1—C1—C8	−118.07 (13)	C4—C5—C6—C9	−178.83 (14)
O2—S1—C1—C2	−37.66 (13)	C2—C1—C8—O1	0.68 (15)
C17—S1—C1—C2	72.54 (13)	S1—C1—C8—O1	−170.20 (10)
C8—C1—C2—C7	−1.27 (15)	C2—C1—C8—C10	−178.15 (15)
S1—C1—C2—C7	169.92 (10)	S1—C1—C8—C10	11.0 (2)
C8—C1—C2—C3	−178.44 (15)	C7—O1—C8—C1	0.20 (14)
S1—C1—C2—C3	−7.3 (2)	C7—O1—C8—C10	179.30 (11)
C7—C2—C3—C4	0.1 (2)	C1—C8—C10—C15	15.7 (2)
C1—C2—C3—C4	176.96 (15)	O1—C8—C10—C15	−163.06 (12)
C2—C3—C4—C5	−1.2 (2)	C1—C8—C10—C11	−165.94 (15)
C2—C3—C4—Cl1	−178.57 (10)	O1—C8—C10—C11	15.27 (18)
C3—C4—C5—C6	1.0 (2)	C15—C10—C11—C12	0.8 (2)
Cl1—C4—C5—C6	178.51 (11)	C8—C10—C11—C12	−177.59 (13)
C8—O1—C7—C6	176.97 (13)	C10—C11—C12—C13	−0.8 (2)
C8—O1—C7—C2	−1.06 (14)	C11—C12—C13—C14	0.0 (2)
C3—C2—C7—O1	179.17 (11)	C11—C12—C13—C16	179.84 (14)
C1—C2—C7—O1	1.44 (15)	C12—C13—C14—C15	0.9 (2)
C3—C2—C7—C6	1.2 (2)	C16—C13—C14—C15	−179.02 (14)
C1—C2—C7—C6	−176.57 (13)	C13—C14—C15—C10	−0.8 (2)
O1—C7—C6—C5	−179.01 (12)	C11—C10—C15—C14	0.0 (2)
C2—C7—C6—C5	−1.3 (2)	C8—C10—C15—C14	178.34 (13)
O1—C7—C6—C9	0.0 (2)	O2—S1—C17—C18	−170.38 (10)
C2—C7—C6—C9	177.75 (13)	C1—S1—C17—C18	79.34 (11)