3-(4-Chloro-phenyl-sulfin-yl)-2,5-dimethyl-1-benzofuran.

In the crystal structure of the title compound, C(16)H(13)ClO(2)S, the 4-chloro-phenyl ring is oriented approximately perpendicular to the benzofuran ring plane [dihedral angle = 82.45 (5)°]. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the structures of related 3-(4-fluoro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C16H13ClO2S

M = 304.77

Monoclinic,

a = 12.7673 (19) Å

b = 11.0206 (18) Å

c = 11.1232 (17) Å

β = 113.674 (6)°

V = 1433.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 173 K

0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.654, T max = 0.746

12779 measured reflections

3542 independent reflections

3118 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.124

S = 1.03

3542 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.31 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035932/nc2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035932/nc2196Isup2.hkl

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

C16H13ClO2S	F(000) = 632
Mr = 304.77	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8210 reflections
a = 12.7673 (19) Å	θ = 2.5–28.3°
b = 11.0206 (18) Å	µ = 0.41 mm−1
c = 11.1232 (17) Å	T = 173 K
β = 113.674 (6)°	Block, colourless
V = 1433.4 (4) Å3	0.50 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3542 independent reflections
Radiation source: rotating anode	3118 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.7°
φ and ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.654, Tmax = 0.746	l = −14→13
12779 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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0772P)2 + 0.5141P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3542 reflections	Δρmax = 0.31 e Å−3
184 parameters	Δρmin = −0.31 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: 0.014 (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
Cl	0.76980 (4)	0.23428 (4)	0.27031 (4)	0.04162 (15)
S	0.92673 (3)	0.68708 (4)	0.64073 (4)	0.02874 (14)
O1	0.66438 (10)	0.90669 (11)	0.50482 (12)	0.0371 (3)
O2	0.95961 (10)	0.64186 (13)	0.77732 (11)	0.0398 (3)
C1	0.79481 (13)	0.76039 (14)	0.59101 (14)	0.0261 (3)
C2	0.69064 (12)	0.71954 (15)	0.60000 (14)	0.0264 (3)
C3	0.65623 (13)	0.61696 (16)	0.64794 (15)	0.0303 (3)
H3	0.7071	0.5536	0.6850	0.036*
C4	0.54444 (14)	0.61099 (19)	0.63938 (17)	0.0386 (4)
C5	0.47007 (15)	0.7081 (2)	0.5827 (2)	0.0485 (5)
H5	0.3956	0.7033	0.5772	0.058*
C6	0.50216 (16)	0.8100 (2)	0.5347 (2)	0.0477 (5)
H6	0.4514	0.8734	0.4970	0.057*
C7	0.61371 (14)	0.81344 (16)	0.54552 (16)	0.0333 (4)
C8	0.77512 (14)	0.87155 (15)	0.53477 (15)	0.0315 (3)
C9	0.50414 (17)	0.5015 (2)	0.6895 (2)	0.0520 (5)
H9A	0.5632	0.4410	0.7170	0.078*
H9B	0.4368	0.4692	0.6209	0.078*
H9C	0.4867	0.5245	0.7627	0.078*
C10	0.84732 (19)	0.95889 (18)	0.50136 (19)	0.0452 (4)
H10A	0.8743	1.0205	0.5679	0.068*
H10B	0.8031	0.9958	0.4181	0.068*
H10C	0.9114	0.9170	0.4964	0.068*
C11	0.87780 (11)	0.55732 (14)	0.53501 (14)	0.0253 (3)
C12	0.82630 (14)	0.57394 (16)	0.40013 (15)	0.0319 (3)
H12	0.8142	0.6517	0.3646	0.038*
C13	0.79335 (14)	0.47361 (16)	0.31949 (15)	0.0324 (3)
H13	0.7581	0.4831	0.2289	0.039*
C14	0.81304 (12)	0.35892 (15)	0.37406 (15)	0.0272 (3)
C16	0.89862 (12)	0.44303 (15)	0.58916 (15)	0.0293 (3)
H16	0.9347	0.4336	0.6797	0.035*
C15	0.86562 (14)	0.34154 (16)	0.50817 (16)	0.0314 (3)
H15	0.8787	0.2637	0.5435	0.038*

	U11	U22	U33	U12	U13	U23
Cl	0.0453 (3)	0.0364 (3)	0.0423 (3)	−0.00681 (17)	0.0167 (2)	−0.01106 (18)
S	0.0214 (2)	0.0302 (2)	0.0333 (2)	−0.00229 (13)	0.00965 (15)	−0.00328 (15)
O1	0.0419 (6)	0.0266 (6)	0.0358 (6)	0.0078 (5)	0.0084 (5)	−0.0007 (5)
O2	0.0369 (6)	0.0435 (7)	0.0287 (6)	0.0039 (5)	0.0025 (5)	−0.0033 (5)
C1	0.0274 (7)	0.0247 (7)	0.0260 (7)	0.0000 (5)	0.0106 (5)	−0.0024 (6)
C2	0.0236 (6)	0.0305 (8)	0.0239 (6)	0.0025 (5)	0.0084 (5)	−0.0040 (6)
C3	0.0254 (7)	0.0368 (9)	0.0285 (7)	−0.0012 (6)	0.0106 (6)	−0.0007 (6)
C4	0.0296 (8)	0.0552 (12)	0.0337 (8)	−0.0072 (7)	0.0155 (6)	−0.0082 (8)
C5	0.0261 (8)	0.0683 (14)	0.0529 (11)	0.0017 (8)	0.0177 (8)	−0.0129 (10)
C6	0.0315 (8)	0.0547 (12)	0.0513 (11)	0.0167 (8)	0.0106 (8)	−0.0075 (9)
C7	0.0323 (8)	0.0319 (9)	0.0326 (8)	0.0053 (6)	0.0097 (6)	−0.0066 (6)
C8	0.0389 (8)	0.0262 (8)	0.0264 (7)	−0.0010 (6)	0.0099 (6)	−0.0048 (6)
C9	0.0408 (10)	0.0737 (15)	0.0464 (10)	−0.0196 (10)	0.0226 (8)	−0.0039 (10)
C10	0.0619 (12)	0.0323 (10)	0.0402 (9)	−0.0122 (8)	0.0193 (8)	0.0001 (8)
C11	0.0206 (6)	0.0290 (7)	0.0289 (7)	0.0005 (5)	0.0128 (5)	−0.0009 (6)
C12	0.0385 (8)	0.0286 (8)	0.0291 (7)	0.0031 (6)	0.0141 (6)	0.0056 (6)
C13	0.0361 (8)	0.0362 (9)	0.0252 (7)	0.0021 (6)	0.0125 (6)	0.0028 (6)
C14	0.0238 (6)	0.0300 (8)	0.0300 (7)	−0.0009 (5)	0.0132 (6)	−0.0027 (6)
C16	0.0285 (7)	0.0326 (8)	0.0257 (7)	0.0035 (6)	0.0097 (6)	0.0048 (6)
C15	0.0325 (7)	0.0276 (8)	0.0331 (8)	0.0020 (6)	0.0122 (6)	0.0035 (6)

Cl—C14	1.7355 (16)	C8—C10	1.480 (2)
S—O2	1.4902 (13)	C9—H9A	0.9600
S—C1	1.7457 (15)	C9—H9B	0.9600
S—C11	1.7966 (16)	C9—H9C	0.9600
O1—C8	1.372 (2)	C10—H10A	0.9600
O1—C7	1.384 (2)	C10—H10B	0.9600
C1—C8	1.352 (2)	C10—H10C	0.9600
C1—C2	1.445 (2)	C11—C16	1.375 (2)
C2—C7	1.387 (2)	C11—C12	1.387 (2)
C2—C3	1.394 (2)	C12—C13	1.379 (2)
C3—C4	1.393 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.381 (2)
C4—C5	1.401 (3)	C13—H13	0.9300
C4—C9	1.504 (3)	C14—C15	1.381 (2)
C5—C6	1.375 (3)	C16—C15	1.391 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.381 (3)	C15—H15	0.9300
C6—H6	0.9300
O2—S—C1	108.59 (7)	C4—C9—H9B	109.5
O2—S—C11	106.42 (8)	H9A—C9—H9B	109.5
C1—S—C11	97.08 (7)	C4—C9—H9C	109.5
C8—O1—C7	106.41 (13)	H9A—C9—H9C	109.5
C8—C1—C2	107.99 (14)	H9B—C9—H9C	109.5
C8—C1—S	122.84 (12)	C8—C10—H10A	109.5
C2—C1—S	129.17 (12)	C8—C10—H10B	109.5
C7—C2—C3	119.70 (14)	H10A—C10—H10B	109.5
C7—C2—C1	104.31 (14)	C8—C10—H10C	109.5
C3—C2—C1	135.99 (14)	H10A—C10—H10C	109.5
C4—C3—C2	118.93 (16)	H10B—C10—H10C	109.5
C4—C3—H3	120.5	C16—C11—C12	121.26 (15)
C2—C3—H3	120.5	C16—C11—S	119.15 (11)
C3—C4—C5	119.02 (18)	C12—C11—S	119.47 (12)
C3—C4—C9	120.41 (18)	C13—C12—C11	119.08 (15)
C5—C4—C9	120.57 (17)	C13—C12—H12	120.5
C6—C5—C4	123.03 (17)	C11—C12—H12	120.5
C6—C5—H5	118.5	C12—C13—C14	119.60 (14)
C4—C5—H5	118.5	C12—C13—H13	120.2
C5—C6—C7	116.50 (17)	C14—C13—H13	120.2
C5—C6—H6	121.8	C13—C14—C15	121.69 (15)
C7—C6—H6	121.8	C13—C14—Cl	118.62 (12)
C6—C7—O1	126.38 (17)	C15—C14—Cl	119.68 (13)
C6—C7—C2	122.83 (18)	C11—C16—C15	119.85 (14)
O1—C7—C2	110.79 (14)	C11—C16—H16	120.1
C1—C8—O1	110.50 (14)	C15—C16—H16	120.1
C1—C8—C10	133.36 (16)	C14—C15—C16	118.51 (15)
O1—C8—C10	116.14 (16)	C14—C15—H15	120.7
C4—C9—H9A	109.5	C16—C15—H15	120.7
O2—S—C1—C8	131.30 (14)	C1—C2—C7—O1	0.08 (17)
C11—S—C1—C8	−118.68 (14)	C2—C1—C8—O1	−0.52 (17)
O2—S—C1—C2	−48.63 (16)	S—C1—C8—O1	179.54 (10)
C11—S—C1—C2	61.39 (15)	C2—C1—C8—C10	179.19 (17)
C8—C1—C2—C7	0.26 (17)	S—C1—C8—C10	−0.7 (3)
S—C1—C2—C7	−179.80 (12)	C7—O1—C8—C1	0.56 (17)
C8—C1—C2—C3	−179.12 (17)	C7—O1—C8—C10	−179.21 (14)
S—C1—C2—C3	0.8 (3)	O2—S—C11—C16	−13.00 (13)
C7—C2—C3—C4	0.3 (2)	C1—S—C11—C16	−124.81 (12)
C1—C2—C3—C4	179.60 (16)	O2—S—C11—C12	171.00 (12)
C2—C3—C4—C5	0.1 (2)	C1—S—C11—C12	59.20 (13)
C2—C3—C4—C9	179.73 (16)	C16—C11—C12—C13	1.4 (2)
C3—C4—C5—C6	−0.1 (3)	S—C11—C12—C13	177.30 (12)
C9—C4—C5—C6	−179.70 (19)	C11—C12—C13—C14	−0.6 (2)
C4—C5—C6—C7	−0.3 (3)	C12—C13—C14—C15	−0.3 (2)
C5—C6—C7—O1	−179.62 (17)	C12—C13—C14—Cl	179.56 (12)
C5—C6—C7—C2	0.8 (3)	C12—C11—C16—C15	−1.3 (2)
C8—O1—C7—C6	179.97 (17)	S—C11—C16—C15	−177.26 (12)
C8—O1—C7—C2	−0.38 (17)	C13—C14—C15—C16	0.3 (2)
C3—C2—C7—C6	−0.7 (2)	Cl—C14—C15—C16	−179.50 (11)
C1—C2—C7—C6	179.74 (16)	C11—C16—C15—C14	0.5 (2)
C3—C2—C7—O1	179.58 (13)

Cg1 is the centroid of the C1, C2, C7, O1, C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2i	0.96	2.51	3.366 (2)	148
C15—H15···O2ii	0.93	2.60	3.353 (2)	139
C13—H13···Cg1iii	0.93	2.85	3.566 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1, C2, C7, O1, C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2i	0.96	2.51	3.366 (2)	148
C15—H15⋯O2ii	0.93	2.60	3.353 (2)	139
C13—H13⋯Cg1iii	0.93	2.85	3.566 (2)	135

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