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

In the title compound, C16H12ClFO2S, the dihedral angle between the mean planes of the benzo-furan and 2-fluoro-phenyl rings is 34.85 (6)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming zigzag chains along [001]. The chains are linked by C-H⋯π inter-actions, forming a three-dimensional structure.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2013 ▶).

Experimental

Crystal data

C16H12ClFO2S

M = 322.77

Monoclinic,

a = 11.3980 (2) Å

b = 15.7819 (4) Å

c = 16.7231 (4) Å

β = 104.370 (1)°

V = 2914.07 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 173 K

0.55 × 0.35 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.678, T max = 0.746

13530 measured reflections

3601 independent reflections

3105 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

3601 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 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/S1600536814011635/cv5456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011635/cv5456Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011635/cv5456Isup3.cml

CCDC reference: 1004137

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

C16H12ClFO2S	F(000) = 1328
Mr = 322.77	Dx = 1.471 Mg m−3
Monoclinic, C2/c	Melting point = 420–419 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.3980 (2) Å	Cell parameters from 6112 reflections
b = 15.7819 (4) Å	θ = 2.3–28.3°
c = 16.7231 (4) Å	µ = 0.42 mm−1
β = 104.370 (1)°	T = 173 K
V = 2914.07 (11) Å3	Block, colourless
Z = 8	0.55 × 0.35 × 0.33 mm

Bruker SMART APEXII CCD diffractometer	3601 independent reflections
Radiation source: rotating anode	3105 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.3°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→13
Tmin = 0.678, Tmax = 0.746	l = −22→22
13530 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0488P)2 + 2.3447P] where P = (Fo2 + 2Fc2)/3
3601 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.37 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
S1	0.32997 (4)	0.67149 (3)	0.68519 (2)	0.02744 (11)
Cl1	0.08168 (4)	0.41662 (3)	0.42374 (3)	0.03932 (13)
F1	0.41414 (9)	0.83843 (6)	0.64599 (7)	0.0411 (3)
O1	0.48466 (9)	0.65185 (7)	0.49830 (6)	0.0241 (2)
O2	0.29800 (12)	0.58583 (8)	0.71083 (7)	0.0400 (3)
C1	0.37028 (13)	0.65573 (9)	0.59058 (8)	0.0234 (3)
C2	0.31849 (13)	0.59295 (9)	0.52894 (8)	0.0229 (3)
C3	0.22012 (13)	0.53726 (10)	0.51473 (9)	0.0257 (3)
H3	0.1677	0.5342	0.5508	0.031*
C4	0.20354 (13)	0.48715 (10)	0.44560 (9)	0.0265 (3)
C5	0.27923 (13)	0.48869 (10)	0.39107 (9)	0.0258 (3)
H5	0.2627	0.4524	0.3443	0.031*
C6	0.37786 (13)	0.54272 (10)	0.40503 (8)	0.0235 (3)
C7	0.39325 (12)	0.59329 (9)	0.47455 (9)	0.0223 (3)
C8	0.46851 (13)	0.68894 (10)	0.56957 (8)	0.0239 (3)
C9	0.55823 (13)	0.75389 (10)	0.60357 (9)	0.0254 (3)
C10	0.52975 (15)	0.82705 (10)	0.64050 (9)	0.0301 (3)
C11	0.61223 (17)	0.89018 (11)	0.67021 (10)	0.0364 (4)
H11	0.5891	0.9393	0.6954	0.044*
C12	0.72974 (17)	0.88051 (12)	0.66256 (11)	0.0392 (4)
H12	0.7884	0.9231	0.6829	0.047*
C13	0.76166 (16)	0.80876 (12)	0.62528 (11)	0.0397 (4)
H13	0.8423	0.8025	0.6200	0.048*
C14	0.67724 (14)	0.74612 (11)	0.59571 (10)	0.0324 (3)
H14	0.7002	0.6974	0.5699	0.039*
C15	0.46317 (14)	0.54748 (11)	0.34986 (9)	0.0279 (3)
H15A	0.4437	0.5025	0.3083	0.042*
H15B	0.5465	0.5403	0.3829	0.042*
H15C	0.4550	0.6028	0.3223	0.042*
C16	0.18856 (15)	0.72430 (12)	0.64558 (11)	0.0373 (4)
H16A	0.1382	0.6906	0.6008	0.056*
H16B	0.2033	0.7802	0.6244	0.056*
H16C	0.1468	0.7310	0.6898	0.056*

	U11	U22	U33	U12	U13	U23
S1	0.0348 (2)	0.0279 (2)	0.02088 (18)	0.00321 (16)	0.00929 (14)	0.00125 (14)
Cl1	0.0300 (2)	0.0385 (2)	0.0518 (3)	−0.01287 (17)	0.01449 (17)	−0.01152 (19)
F1	0.0430 (6)	0.0310 (5)	0.0536 (6)	0.0006 (4)	0.0199 (5)	−0.0065 (5)
O1	0.0255 (5)	0.0245 (5)	0.0229 (5)	−0.0035 (4)	0.0071 (4)	−0.0021 (4)
O2	0.0598 (8)	0.0311 (7)	0.0356 (6)	0.0043 (6)	0.0243 (6)	0.0098 (5)
C1	0.0282 (7)	0.0225 (7)	0.0200 (6)	0.0016 (6)	0.0067 (5)	0.0014 (6)
C2	0.0252 (7)	0.0221 (7)	0.0220 (6)	0.0023 (6)	0.0071 (5)	0.0024 (6)
C3	0.0245 (7)	0.0262 (8)	0.0279 (7)	0.0001 (6)	0.0096 (5)	0.0017 (6)
C4	0.0223 (7)	0.0244 (8)	0.0327 (8)	−0.0039 (6)	0.0068 (6)	0.0001 (6)
C5	0.0270 (7)	0.0242 (7)	0.0261 (7)	−0.0004 (6)	0.0062 (5)	−0.0031 (6)
C6	0.0251 (7)	0.0230 (7)	0.0230 (6)	0.0015 (6)	0.0073 (5)	0.0009 (6)
C7	0.0226 (6)	0.0215 (7)	0.0227 (6)	−0.0016 (6)	0.0057 (5)	0.0015 (6)
C8	0.0284 (7)	0.0224 (7)	0.0203 (6)	0.0008 (6)	0.0050 (5)	0.0005 (6)
C9	0.0306 (7)	0.0230 (7)	0.0212 (6)	−0.0030 (6)	0.0042 (5)	0.0022 (6)
C10	0.0371 (8)	0.0279 (8)	0.0260 (7)	−0.0014 (7)	0.0092 (6)	0.0022 (6)
C11	0.0528 (10)	0.0258 (8)	0.0301 (8)	−0.0062 (8)	0.0090 (7)	−0.0024 (7)
C12	0.0448 (10)	0.0337 (9)	0.0352 (9)	−0.0146 (8)	0.0026 (7)	−0.0003 (7)
C13	0.0329 (8)	0.0390 (10)	0.0452 (10)	−0.0094 (8)	0.0061 (7)	0.0005 (8)
C14	0.0321 (8)	0.0291 (8)	0.0353 (8)	−0.0034 (7)	0.0071 (6)	−0.0016 (7)
C15	0.0287 (7)	0.0310 (8)	0.0266 (7)	−0.0007 (6)	0.0119 (6)	−0.0030 (6)
C16	0.0358 (8)	0.0336 (9)	0.0448 (9)	0.0079 (7)	0.0140 (7)	0.0015 (8)

S1—O2	1.4906 (13)	C8—C9	1.460 (2)
S1—C1	1.7712 (14)	C9—C10	1.385 (2)
S1—C16	1.7892 (17)	C9—C14	1.400 (2)
Cl1—C4	1.7464 (15)	C10—C11	1.375 (2)
F1—C10	1.3554 (19)	C11—C12	1.385 (3)
O1—C7	1.3755 (17)	C11—H11	0.9500
O1—C8	1.3805 (17)	C12—C13	1.384 (3)
C1—C8	1.359 (2)	C12—H12	0.9500
C1—C2	1.446 (2)	C13—C14	1.383 (2)
C2—C7	1.3922 (19)	C13—H13	0.9500
C2—C3	1.398 (2)	C14—H14	0.9500
C3—C4	1.375 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.402 (2)	C15—H15C	0.9800
C5—C6	1.384 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.385 (2)	C16—H16C	0.9800
C6—C15	1.4992 (19)
O2—S1—C1	105.41 (7)	C10—C9—C8	122.68 (14)
O2—S1—C16	105.47 (8)	C14—C9—C8	120.21 (14)
C1—S1—C16	98.30 (8)	F1—C10—C11	117.93 (15)
C7—O1—C8	106.28 (11)	F1—C10—C9	118.68 (14)
C8—C1—C2	107.26 (12)	C11—C10—C9	123.37 (16)
C8—C1—S1	126.15 (11)	C10—C11—C12	118.47 (16)
C2—C1—S1	125.63 (11)	C10—C11—H11	120.8
C7—C2—C3	119.11 (13)	C12—C11—H11	120.8
C7—C2—C1	104.79 (12)	C13—C12—C11	120.00 (16)
C3—C2—C1	136.09 (13)	C13—C12—H12	120.0
C4—C3—C2	116.22 (13)	C11—C12—H12	120.0
C4—C3—H3	121.9	C14—C13—C12	120.57 (17)
C2—C3—H3	121.9	C14—C13—H13	119.7
C3—C4—C5	123.95 (14)	C12—C13—H13	119.7
C3—C4—Cl1	118.62 (12)	C13—C14—C9	120.54 (16)
C5—C4—Cl1	117.43 (12)	C13—C14—H14	119.7
C6—C5—C4	120.40 (14)	C9—C14—H14	119.7
C6—C5—H5	119.8	C6—C15—H15A	109.5
C4—C5—H5	119.8	C6—C15—H15B	109.5
C5—C6—C7	115.15 (13)	H15A—C15—H15B	109.5
C5—C6—C15	123.42 (13)	C6—C15—H15C	109.5
C7—C6—C15	121.43 (13)	H15A—C15—H15C	109.5
O1—C7—C6	123.96 (13)	H15B—C15—H15C	109.5
O1—C7—C2	110.89 (12)	S1—C16—H16A	109.5
C6—C7—C2	125.15 (14)	S1—C16—H16B	109.5
C1—C8—O1	110.77 (12)	H16A—C16—H16B	109.5
C1—C8—C9	135.43 (14)	S1—C16—H16C	109.5
O1—C8—C9	113.79 (12)	H16A—C16—H16C	109.5
C10—C9—C14	117.03 (14)	H16B—C16—H16C	109.5
O2—S1—C1—C8	−134.26 (14)	C3—C2—C7—C6	0.8 (2)
C16—S1—C1—C8	117.09 (15)	C1—C2—C7—C6	−179.82 (14)
O2—S1—C1—C2	33.03 (14)	C2—C1—C8—O1	−0.17 (16)
C16—S1—C1—C2	−75.62 (14)	S1—C1—C8—O1	169.04 (10)
C8—C1—C2—C7	0.49 (16)	C2—C1—C8—C9	179.06 (16)
S1—C1—C2—C7	−168.79 (11)	S1—C1—C8—C9	−11.7 (3)
C8—C1—C2—C3	179.68 (16)	C7—O1—C8—C1	−0.23 (16)
S1—C1—C2—C3	10.4 (3)	C7—O1—C8—C9	−179.64 (12)
C7—C2—C3—C4	−1.2 (2)	C1—C8—C9—C10	−36.0 (3)
C1—C2—C3—C4	179.75 (16)	O1—C8—C9—C10	143.19 (14)
C2—C3—C4—C5	0.7 (2)	C1—C8—C9—C14	147.49 (18)
C2—C3—C4—Cl1	−179.56 (11)	O1—C8—C9—C14	−33.30 (19)
C3—C4—C5—C6	0.1 (2)	C14—C9—C10—F1	177.23 (13)
Cl1—C4—C5—C6	−179.61 (11)	C8—C9—C10—F1	0.6 (2)
C4—C5—C6—C7	−0.5 (2)	C14—C9—C10—C11	−1.0 (2)
C4—C5—C6—C15	179.58 (14)	C8—C9—C10—C11	−177.64 (15)
C8—O1—C7—C6	179.74 (13)	F1—C10—C11—C12	−177.97 (15)
C8—O1—C7—C2	0.56 (15)	C9—C10—C11—C12	0.3 (2)
C5—C6—C7—O1	−179.04 (13)	C10—C11—C12—C13	0.4 (3)
C15—C6—C7—O1	0.9 (2)	C11—C12—C13—C14	−0.3 (3)
C5—C6—C7—C2	0.0 (2)	C12—C13—C14—C9	−0.5 (3)
C15—C6—C7—C2	179.97 (14)	C10—C9—C14—C13	1.1 (2)
C3—C2—C7—O1	179.99 (12)	C8—C9—C14—C13	177.80 (15)
C1—C2—C7—O1	−0.65 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.44	3.2916 (19)	149
C15—H15A···O2i	0.98	2.45	3.347 (2)	152
C16—H16B···Cg1ii	0.98	2.92	3.641 (2)	131

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
C5—H5⋯O2i	0.95	2.44	3.2916 (19)	149
C15—H15A⋯O2i	0.98	2.45	3.347 (2)	152
C16—H16B⋯Cg1ii	0.98	2.92	3.641 (2)	131

Symmetry codes: (i) ; (ii) .