2-(4-Chloro-phen-yl)-3-ethyl-sulfinyl-5-fluoro-1-benzofuran.

In the title compound, C(16)H(12)ClFO(2)S, the 4-chloro-phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 19.79 (8)°. The crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the crystal structures of similar 3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010 ▶). For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶).

Experimental

Crystal data

C16H12ClFO2S

M = 322.77

Monoclinic,

a = 11.5257 (9) Å

b = 7.9655 (6) Å

c = 16.395 (1) Å

β = 106.518 (1)°

V = 1443.07 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 173 K

0.40 × 0.35 × 0.35 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.850, T max = 0.867

12345 measured reflections

3290 independent reflections

2713 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.05

3290 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 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/S1600536810008172/bh2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008172/bh2275Isup2.hkl

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

C16H12ClFO2S	F(000) = 664
Mr = 322.77	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Melting point = 405–406 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5257 (9) Å	Cell parameters from 5508 reflections
b = 7.9655 (6) Å	θ = 2.6–27.4°
c = 16.395 (1) Å	µ = 0.42 mm−1
β = 106.518 (1)°	T = 173 K
V = 1443.07 (18) Å3	Block, colourless
Z = 4	0.40 × 0.35 × 0.35 mm

Bruker SMART APEXII CCD diffractometer	3290 independent reflections
Radiation source: Rotating Anode	2713 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.850, Tmax = 0.867	l = −21→20
12345 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.7418P] where P = (Fo2 + 2Fc2)/3
3290 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cl	1.01429 (4)	0.47181 (6)	0.72194 (3)	0.03651 (13)
S	0.37916 (4)	0.44605 (5)	0.71678 (2)	0.02292 (11)
F	−0.02836 (9)	0.79231 (16)	0.49298 (7)	0.0447 (3)
O1	0.45081 (10)	0.71492 (14)	0.53223 (7)	0.0262 (3)
O2	0.30653 (12)	0.54333 (16)	0.76279 (8)	0.0335 (3)
C1	0.38345 (15)	0.56819 (19)	0.62737 (10)	0.0228 (3)
C2	0.28142 (15)	0.6562 (2)	0.57188 (10)	0.0242 (3)
C3	0.15813 (15)	0.6723 (2)	0.56551 (11)	0.0282 (4)
H3	0.1231	0.6178	0.6028	0.034*
C4	0.09200 (16)	0.7732 (2)	0.50110 (12)	0.0321 (4)
C5	0.13881 (17)	0.8572 (2)	0.44327 (11)	0.0328 (4)
H5	0.0886	0.9230	0.4008	0.039*
C6	0.26012 (17)	0.8427 (2)	0.44906 (11)	0.0292 (4)
H6	0.2942	0.8969	0.4112	0.035*
C7	0.32842 (15)	0.7429 (2)	0.51444 (10)	0.0249 (3)
C8	0.48285 (15)	0.6093 (2)	0.60191 (10)	0.0233 (3)
C9	0.61217 (15)	0.5719 (2)	0.63190 (10)	0.0236 (3)
C10	0.65770 (15)	0.4350 (2)	0.68435 (11)	0.0262 (4)
H10	0.6045	0.3628	0.7002	0.031*
C11	0.78105 (15)	0.4052 (2)	0.71314 (11)	0.0274 (4)
H11	0.8108	0.3149	0.7489	0.033*
C12	0.85925 (15)	0.5115 (2)	0.68801 (11)	0.0270 (4)
C13	0.81697 (16)	0.6470 (2)	0.63528 (11)	0.0308 (4)
H13	0.8706	0.7166	0.6183	0.037*
C14	0.69410 (16)	0.6776 (2)	0.60811 (11)	0.0288 (4)
H14	0.6653	0.7698	0.5735	0.035*
C15	0.28229 (16)	0.2801 (2)	0.66061 (11)	0.0285 (4)
H15A	0.2502	0.2179	0.7002	0.034*
H15B	0.2146	0.3287	0.6177	0.034*
C16	0.3499 (2)	0.1613 (2)	0.61849 (13)	0.0414 (5)
H16A	0.3808	0.2223	0.5786	0.062*
H16B	0.2959	0.0750	0.5891	0.062*
H16C	0.4159	0.1113	0.6610	0.062*

	U11	U22	U33	U12	U13	U23
Cl	0.0231 (2)	0.0483 (3)	0.0378 (3)	0.00038 (19)	0.00815 (18)	−0.0005 (2)
S	0.0255 (2)	0.0234 (2)	0.0200 (2)	0.00029 (16)	0.00665 (15)	0.00033 (15)
F	0.0275 (6)	0.0575 (8)	0.0458 (7)	0.0124 (5)	0.0052 (5)	0.0073 (6)
O1	0.0286 (6)	0.0259 (6)	0.0249 (6)	0.0006 (5)	0.0091 (5)	0.0030 (5)
O2	0.0433 (8)	0.0313 (7)	0.0311 (7)	0.0041 (6)	0.0192 (6)	−0.0023 (5)
C1	0.0251 (8)	0.0207 (8)	0.0223 (8)	0.0015 (6)	0.0065 (6)	0.0010 (6)
C2	0.0293 (9)	0.0213 (8)	0.0218 (8)	0.0021 (7)	0.0072 (7)	−0.0013 (6)
C3	0.0279 (9)	0.0302 (9)	0.0269 (9)	0.0025 (7)	0.0085 (7)	0.0007 (7)
C4	0.0275 (9)	0.0348 (10)	0.0315 (9)	0.0059 (8)	0.0043 (7)	−0.0031 (8)
C5	0.0400 (11)	0.0291 (9)	0.0246 (9)	0.0081 (8)	0.0017 (8)	0.0012 (7)
C6	0.0407 (10)	0.0249 (9)	0.0218 (8)	0.0019 (7)	0.0086 (7)	0.0001 (7)
C7	0.0284 (9)	0.0226 (8)	0.0240 (8)	0.0017 (7)	0.0077 (7)	−0.0024 (6)
C8	0.0292 (9)	0.0191 (8)	0.0218 (8)	−0.0012 (7)	0.0077 (7)	−0.0008 (6)
C9	0.0254 (8)	0.0234 (8)	0.0227 (8)	−0.0014 (6)	0.0080 (7)	−0.0040 (6)
C10	0.0264 (9)	0.0224 (8)	0.0322 (9)	−0.0027 (7)	0.0123 (7)	−0.0007 (7)
C11	0.0290 (9)	0.0233 (8)	0.0300 (9)	0.0030 (7)	0.0086 (7)	0.0006 (7)
C12	0.0221 (8)	0.0329 (9)	0.0260 (8)	−0.0008 (7)	0.0070 (7)	−0.0068 (7)
C13	0.0303 (9)	0.0343 (10)	0.0298 (9)	−0.0074 (8)	0.0115 (8)	0.0017 (8)
C14	0.0313 (9)	0.0293 (9)	0.0258 (9)	−0.0029 (7)	0.0082 (7)	0.0037 (7)
C15	0.0308 (9)	0.0234 (8)	0.0286 (9)	−0.0050 (7)	0.0038 (7)	0.0005 (7)
C16	0.0585 (13)	0.0296 (10)	0.0344 (11)	0.0016 (9)	0.0105 (9)	−0.0066 (8)

Cl—C12	1.7427 (17)	C8—C9	1.461 (2)
S—O2	1.4930 (12)	C9—C10	1.395 (2)
S—C1	1.7717 (16)	C9—C14	1.401 (2)
S—C15	1.8047 (17)	C10—C11	1.385 (2)
F—C4	1.364 (2)	C10—H10	0.9300
O1—C7	1.375 (2)	C11—C12	1.382 (2)
O1—C8	1.3820 (19)	C11—H11	0.9300
C1—C8	1.366 (2)	C12—C13	1.382 (2)
C1—C2	1.447 (2)	C13—C14	1.380 (2)
C2—C7	1.395 (2)	C13—H13	0.9300
C2—C3	1.401 (2)	C14—H14	0.9300
C3—C4	1.373 (2)	C15—C16	1.512 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.389 (3)	C15—H15B	0.9700
C5—C6	1.379 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.386 (2)	C16—H16C	0.9600
C6—H6	0.9300
O2—S—C1	106.53 (7)	C10—C9—C8	122.36 (15)
O2—S—C15	106.47 (8)	C14—C9—C8	119.21 (15)
C1—S—C15	97.97 (8)	C11—C10—C9	120.90 (16)
C7—O1—C8	106.91 (12)	C11—C10—H10	119.5
C8—C1—C2	107.11 (14)	C9—C10—H10	119.5
C8—C1—S	127.41 (13)	C12—C11—C10	119.14 (16)
C2—C1—S	125.26 (12)	C12—C11—H11	120.4
C7—C2—C3	118.97 (15)	C10—C11—H11	120.4
C7—C2—C1	105.19 (14)	C11—C12—C13	121.38 (16)
C3—C2—C1	135.83 (16)	C11—C12—Cl	119.38 (14)
C4—C3—C2	116.15 (16)	C13—C12—Cl	119.23 (14)
C4—C3—H3	121.9	C14—C13—C12	119.14 (16)
C2—C3—H3	121.9	C14—C13—H13	120.4
F—C4—C3	117.85 (16)	C12—C13—H13	120.4
F—C4—C5	117.48 (16)	C13—C14—C9	121.00 (16)
C3—C4—C5	124.67 (17)	C13—C14—H14	119.5
C6—C5—C4	119.71 (16)	C9—C14—H14	119.5
C6—C5—H5	120.1	C16—C15—S	111.53 (13)
C4—C5—H5	120.1	C16—C15—H15A	109.3
C5—C6—C7	116.30 (16)	S—C15—H15A	109.3
C5—C6—H6	121.8	C16—C15—H15B	109.3
C7—C6—H6	121.8	S—C15—H15B	109.3
O1—C7—C6	125.43 (15)	H15A—C15—H15B	108.0
O1—C7—C2	110.38 (14)	C15—C16—H16A	109.5
C6—C7—C2	124.18 (16)	C15—C16—H16B	109.5
C1—C8—O1	110.38 (14)	H16A—C16—H16B	109.5
C1—C8—C9	135.43 (15)	C15—C16—H16C	109.5
O1—C8—C9	114.16 (14)	H16A—C16—H16C	109.5
C10—C9—C14	118.43 (16)	H16B—C16—H16C	109.5
O2—S—C1—C8	130.71 (15)	C2—C1—C8—O1	−1.44 (18)
C15—S—C1—C8	−119.40 (16)	S—C1—C8—O1	−176.28 (11)
O2—S—C1—C2	−43.25 (16)	C2—C1—C8—C9	176.59 (17)
C15—S—C1—C2	66.64 (15)	S—C1—C8—C9	1.8 (3)
C8—C1—C2—C7	1.33 (18)	C7—O1—C8—C1	0.97 (17)
S—C1—C2—C7	176.32 (12)	C7—O1—C8—C9	−177.52 (13)
C8—C1—C2—C3	−177.60 (19)	C1—C8—C9—C10	20.4 (3)
S—C1—C2—C3	−2.6 (3)	O1—C8—C9—C10	−161.65 (14)
C7—C2—C3—C4	0.7 (2)	C1—C8—C9—C14	−158.99 (19)
C1—C2—C3—C4	179.52 (18)	O1—C8—C9—C14	19.0 (2)
C2—C3—C4—F	−179.86 (15)	C14—C9—C10—C11	0.8 (2)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C11	−178.60 (15)
F—C4—C5—C6	179.66 (16)	C9—C10—C11—C12	−1.2 (3)
C3—C4—C5—C6	−0.5 (3)	C10—C11—C12—C13	0.4 (3)
C4—C5—C6—C7	−0.3 (3)	C10—C11—C12—Cl	−178.48 (13)
C8—O1—C7—C6	179.89 (16)	C11—C12—C13—C14	0.8 (3)
C8—O1—C7—C2	−0.08 (17)	Cl—C12—C13—C14	179.64 (14)
C5—C6—C7—O1	−178.60 (15)	C12—C13—C14—C9	−1.2 (3)
C5—C6—C7—C2	1.4 (3)	C10—C9—C14—C13	0.4 (3)
C3—C2—C7—O1	178.38 (14)	C8—C9—C14—C13	179.81 (16)
C1—C2—C7—O1	−0.77 (18)	O2—S—C15—C16	−174.17 (12)
C3—C2—C7—C6	−1.6 (3)	C1—S—C15—C16	75.90 (14)
C1—C2—C7—C6	179.26 (15)

Cg is the centroid of the C9–C14 4-chlorophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.52	3.371 (2)	152
C11—H11···O2ii	0.93	2.53	3.116 (2)	121
C15—H15A···Cgii	0.97	2.66	3.560 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 4-chloro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.52	3.371 (2)	152
C11—H11⋯O2ii	0.93	2.53	3.116 (2)	121
C15—H15A⋯Cgii	0.97	2.66	3.560 (2)	155

Symmetry codes: (i) ; (ii) .