5-Chloro-2,7-dimethyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C17H15ClO3S, the dihedral angle between the mean planes of the benzo-furan and 3-methyl-phenyl rings is 76.99 (4)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into chains along the b-axis direction. These chains are linked by π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.976 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2013 ▶). For the pharmacological activity of benzo­furan compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶).

Experimental

Crystal data

C17H15ClO3S

M = 334.80

Monoclinic,

a = 8.8707 (2) Å

b = 6.5281 (2) Å

c = 26.3574 (6) Å

β = 96.998 (1)°

V = 1514.96 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 173 K

0.39 × 0.37 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.379, T max = 0.746

25926 measured reflections

3785 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.04

3785 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.36 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/S1600536814007892/im2452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007892/im2452Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007892/im2452Isup3.cml

CCDC reference: 996302

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

C17H15ClO3S	F(000) = 696
Mr = 334.80	Dx = 1.468 Mg m−3
Monoclinic, P21/c	Melting point = 427–426 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8707 (2) Å	Cell parameters from 9774 reflections
b = 6.5281 (2) Å	θ = 2.3–28.2°
c = 26.3574 (6) Å	µ = 0.40 mm−1
β = 96.998 (1)°	T = 173 K
V = 1514.96 (7) Å3	Block, colourless
Z = 4	0.39 × 0.37 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	3785 independent reflections
Radiation source: rotating anode	3252 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.379, Tmax = 0.746	l = −35→35
25926 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.5625P] where P = (Fo2 + 2Fc2)/3
3785 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.36 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
Cl1	0.46121 (5)	0.19905 (8)	0.429671 (15)	0.04483 (13)
S1	0.26452 (4)	0.26977 (6)	0.640843 (13)	0.02803 (11)
O1	0.10204 (12)	0.71057 (17)	0.54903 (4)	0.0332 (2)
O2	0.28126 (13)	0.07207 (17)	0.61832 (4)	0.0362 (3)
O3	0.16362 (12)	0.29082 (19)	0.67929 (4)	0.0375 (3)
C1	0.20875 (16)	0.4421 (2)	0.59217 (5)	0.0287 (3)
C2	0.25155 (16)	0.4327 (2)	0.54104 (5)	0.0293 (3)
C3	0.33886 (17)	0.3021 (3)	0.51474 (5)	0.0319 (3)
H3	0.3865	0.1836	0.5303	0.038*
C4	0.35222 (18)	0.3548 (3)	0.46470 (6)	0.0341 (3)
C5	0.28443 (18)	0.5286 (3)	0.44089 (6)	0.0372 (4)
H5	0.2989	0.5579	0.4065	0.045*
C6	0.19629 (18)	0.6592 (3)	0.46656 (6)	0.0349 (4)
C7	0.18327 (17)	0.6027 (3)	0.51659 (5)	0.0312 (3)
C8	0.11908 (17)	0.6100 (2)	0.59483 (5)	0.0309 (3)
C9	0.1233 (2)	0.8500 (3)	0.44321 (7)	0.0446 (4)
H9A	0.0190	0.8598	0.4516	0.067*
H9B	0.1221	0.8448	0.4060	0.067*
H9C	0.1813	0.9700	0.4567	0.067*
C10	0.0382 (2)	0.7033 (3)	0.63504 (6)	0.0372 (4)
H10A	0.0465	0.6131	0.6650	0.056*
H10B	−0.0691	0.7220	0.6219	0.056*
H10C	0.0837	0.8365	0.6448	0.056*
C11	0.44638 (16)	0.3512 (2)	0.66842 (5)	0.0278 (3)
C12	0.56259 (17)	0.2089 (3)	0.67374 (5)	0.0311 (3)
H12	0.5468	0.0759	0.6595	0.037*
C13	0.70350 (17)	0.2617 (3)	0.70020 (6)	0.0367 (4)
C14	0.72140 (19)	0.4592 (3)	0.71960 (6)	0.0439 (4)
H14	0.8165	0.4980	0.7376	0.053*
C15	0.6050 (2)	0.6008 (3)	0.71351 (6)	0.0429 (4)
H15	0.6211	0.7349	0.7271	0.052*
C16	0.46468 (19)	0.5483 (3)	0.68772 (6)	0.0351 (3)
H16	0.3837	0.6443	0.6834	0.042*
C17	0.82931 (19)	0.1065 (4)	0.70778 (7)	0.0511 (5)
H17A	0.9268	0.1745	0.7057	0.077*
H17B	0.8128	0.0013	0.6812	0.077*
H17C	0.8304	0.0424	0.7415	0.077*

	U11	U22	U33	U12	U13	U23
Cl1	0.0518 (3)	0.0524 (3)	0.0326 (2)	−0.0124 (2)	0.01411 (17)	−0.00595 (18)
S1	0.02839 (18)	0.0322 (2)	0.02295 (17)	−0.00829 (14)	0.00096 (13)	0.00455 (13)
O1	0.0371 (6)	0.0327 (6)	0.0284 (5)	−0.0061 (5)	−0.0012 (4)	0.0043 (4)
O2	0.0403 (6)	0.0312 (6)	0.0350 (6)	−0.0092 (5)	−0.0041 (4)	0.0018 (5)
O3	0.0322 (5)	0.0509 (7)	0.0306 (5)	−0.0060 (5)	0.0078 (4)	0.0114 (5)
C1	0.0315 (7)	0.0314 (8)	0.0224 (6)	−0.0078 (6)	0.0004 (5)	0.0034 (6)
C2	0.0317 (7)	0.0327 (8)	0.0224 (6)	−0.0120 (6)	−0.0007 (5)	0.0025 (6)
C3	0.0352 (7)	0.0346 (8)	0.0255 (7)	−0.0095 (6)	0.0010 (6)	0.0012 (6)
C4	0.0354 (8)	0.0416 (9)	0.0252 (7)	−0.0142 (7)	0.0035 (6)	−0.0027 (6)
C5	0.0414 (8)	0.0472 (10)	0.0220 (7)	−0.0186 (7)	−0.0006 (6)	0.0044 (6)
C6	0.0381 (8)	0.0377 (9)	0.0266 (7)	−0.0159 (7)	−0.0054 (6)	0.0065 (6)
C7	0.0327 (7)	0.0339 (8)	0.0256 (7)	−0.0106 (6)	−0.0022 (5)	0.0011 (6)
C8	0.0327 (7)	0.0331 (8)	0.0257 (7)	−0.0099 (6)	−0.0008 (5)	0.0034 (6)
C9	0.0520 (10)	0.0433 (10)	0.0357 (8)	−0.0131 (8)	−0.0065 (7)	0.0141 (8)
C10	0.0398 (8)	0.0368 (9)	0.0351 (8)	−0.0045 (7)	0.0045 (6)	0.0006 (7)
C11	0.0291 (7)	0.0374 (8)	0.0171 (6)	−0.0102 (6)	0.0031 (5)	0.0007 (6)
C12	0.0312 (7)	0.0407 (9)	0.0218 (6)	−0.0072 (6)	0.0057 (5)	0.0023 (6)
C13	0.0288 (7)	0.0585 (11)	0.0236 (7)	−0.0089 (7)	0.0058 (5)	0.0071 (7)
C14	0.0363 (8)	0.0699 (13)	0.0248 (7)	−0.0221 (9)	0.0005 (6)	−0.0006 (8)
C15	0.0510 (10)	0.0486 (10)	0.0291 (8)	−0.0212 (9)	0.0045 (7)	−0.0085 (7)
C16	0.0407 (8)	0.0394 (9)	0.0257 (7)	−0.0081 (7)	0.0063 (6)	−0.0026 (6)
C17	0.0306 (8)	0.0782 (14)	0.0450 (10)	−0.0011 (9)	0.0062 (7)	0.0143 (10)

Cl1—C4	1.7432 (17)	C9—H9B	0.9800
S1—O2	1.4358 (12)	C9—H9C	0.9800
S1—O3	1.4381 (11)	C10—H10A	0.9800
S1—C1	1.7323 (15)	C10—H10B	0.9800
S1—C11	1.7684 (14)	C10—H10C	0.9800
O1—C8	1.3663 (17)	C11—C12	1.382 (2)
O1—C7	1.3770 (19)	C11—C16	1.386 (2)
C1—C8	1.361 (2)	C12—C13	1.398 (2)
C1—C2	1.4453 (19)	C12—H12	0.9500
C2—C7	1.385 (2)	C13—C14	1.389 (3)
C2—C3	1.393 (2)	C13—C17	1.503 (3)
C3—C4	1.382 (2)	C14—C15	1.380 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.396 (2)	C15—C16	1.386 (2)
C5—C6	1.387 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.387 (2)	C17—H17A	0.9800
C6—C9	1.501 (2)	C17—H17B	0.9800
C8—C10	1.481 (2)	C17—H17C	0.9800
C9—H9A	0.9800
O2—S1—O3	118.80 (7)	C6—C9—H9C	109.5
O2—S1—C1	108.19 (7)	H9A—C9—H9C	109.5
O3—S1—C1	108.28 (7)	H9B—C9—H9C	109.5
O2—S1—C11	107.75 (7)	C8—C10—H10A	109.5
O3—S1—C11	107.25 (7)	C8—C10—H10B	109.5
C1—S1—C11	105.85 (7)	H10A—C10—H10B	109.5
C8—O1—C7	107.04 (12)	C8—C10—H10C	109.5
C8—C1—C2	107.67 (13)	H10A—C10—H10C	109.5
C8—C1—S1	126.92 (11)	H10B—C10—H10C	109.5
C2—C1—S1	125.41 (12)	C12—C11—C16	122.28 (14)
C7—C2—C3	119.83 (13)	C12—C11—S1	118.15 (12)
C7—C2—C1	104.51 (14)	C16—C11—S1	119.34 (12)
C3—C2—C1	135.67 (14)	C11—C12—C13	119.72 (16)
C4—C3—C2	116.10 (15)	C11—C12—H12	120.1
C4—C3—H3	122.0	C13—C12—H12	120.1
C2—C3—H3	122.0	C14—C13—C12	117.86 (16)
C3—C4—C5	123.30 (16)	C14—C13—C17	121.82 (16)
C3—C4—Cl1	118.52 (14)	C12—C13—C17	120.31 (17)
C5—C4—Cl1	118.18 (11)	C15—C14—C13	121.88 (15)
C6—C5—C4	121.16 (14)	C15—C14—H14	119.1
C6—C5—H5	119.4	C13—C14—H14	119.1
C4—C5—H5	119.4	C14—C15—C16	120.38 (17)
C5—C6—C7	114.67 (15)	C14—C15—H15	119.8
C5—C6—C9	123.41 (14)	C16—C15—H15	119.8
C7—C6—C9	121.90 (16)	C11—C16—C15	117.87 (17)
O1—C7—C2	110.66 (12)	C11—C16—H16	121.1
O1—C7—C6	124.40 (15)	C15—C16—H16	121.1
C2—C7—C6	124.94 (16)	C13—C17—H17A	109.5
C1—C8—O1	110.12 (13)	C13—C17—H17B	109.5
C1—C8—C10	134.83 (14)	H17A—C17—H17B	109.5
O1—C8—C10	115.05 (14)	C13—C17—H17C	109.5
C6—C9—H9A	109.5	H17A—C17—H17C	109.5
C6—C9—H9B	109.5	H17B—C17—H17C	109.5
H9A—C9—H9B	109.5
O2—S1—C1—C8	148.58 (13)	C9—C6—C7—O1	1.2 (2)
O3—S1—C1—C8	18.60 (15)	C5—C6—C7—C2	0.7 (2)
C11—S1—C1—C8	−96.14 (14)	C9—C6—C7—C2	−177.79 (15)
O2—S1—C1—C2	−32.04 (14)	C2—C1—C8—O1	−0.48 (16)
O3—S1—C1—C2	−162.03 (12)	S1—C1—C8—O1	178.99 (11)
C11—S1—C1—C2	83.23 (14)	C2—C1—C8—C10	179.12 (16)
C8—C1—C2—C7	0.71 (16)	S1—C1—C8—C10	−1.4 (3)
S1—C1—C2—C7	−178.77 (11)	C7—O1—C8—C1	0.05 (16)
C8—C1—C2—C3	−179.82 (16)	C7—O1—C8—C10	−179.64 (13)
S1—C1—C2—C3	0.7 (3)	O2—S1—C11—C12	−12.65 (13)
C7—C2—C3—C4	0.6 (2)	O3—S1—C11—C12	116.33 (12)
C1—C2—C3—C4	−178.85 (15)	C1—S1—C11—C12	−128.22 (12)
C2—C3—C4—C5	0.4 (2)	O2—S1—C11—C16	172.73 (11)
C2—C3—C4—Cl1	179.49 (11)	O3—S1—C11—C16	−58.29 (13)
C3—C4—C5—C6	−0.9 (2)	C1—S1—C11—C16	57.16 (13)
Cl1—C4—C5—C6	−179.97 (12)	C16—C11—C12—C13	1.2 (2)
C4—C5—C6—C7	0.3 (2)	S1—C11—C12—C13	−173.25 (11)
C4—C5—C6—C9	178.77 (15)	C11—C12—C13—C14	−1.0 (2)
C8—O1—C7—C2	0.43 (16)	C11—C12—C13—C17	177.98 (14)
C8—O1—C7—C6	−178.69 (14)	C12—C13—C14—C15	0.3 (2)
C3—C2—C7—O1	179.73 (13)	C17—C13—C14—C15	−178.72 (15)
C1—C2—C7—O1	−0.69 (16)	C13—C14—C15—C16	0.4 (2)
C3—C2—C7—C6	−1.2 (2)	C12—C11—C16—C15	−0.6 (2)
C1—C2—C7—C6	178.42 (14)	S1—C11—C16—C15	173.82 (11)
C5—C6—C7—O1	179.67 (13)	C14—C15—C16—C11	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O2i	0.98	2.49	3.297 (2)	139
C17—H17A···O3ii	0.98	2.41	3.369 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O2i	0.98	2.49	3.297 (2)	139
C17—H17A⋯O3ii	0.98	2.41	3.369 (2)	165

Symmetry codes: (i) ; (ii) .