3-Ethyl-sulfinyl-2-(3-fluoro-phen-yl)-5-phenyl-1-benzo-furan.

In the title compound, C22H17FO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo-furan ring system and the pendant 3-fluoro-phenyl and phenyl rings are 23.92 (5) and 32.44 (5)°, respectively. In the crystal, mol-ecules are linked by two weak C-H⋯O(sulfin-yl) hydrogen bonds and a C-H⋯π inter-action, forming a sheet, which lies in the ab plane. A π-π inter-action between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.976 (2) Å] links the mol-ecules into inversion dimers and connects adjacent sheets, resulting in a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2006 ▶, 2010 ▶).

Experimental

Crystal data

C22H17FO2S

M = 364.42

Monoclinic,

a = 12.6447 (3) Å

b = 7.1680 (2) Å

c = 19.2382 (5) Å

β = 100.592 (2)°

V = 1713.99 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.38 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.684, T max = 0.746

16390 measured reflections

4269 independent reflections

3406 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.04

4269 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.41 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015924/go2092sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015924/go2092Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015924/go2092Isup3.cml

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

C22H17FO2S	F(000) = 760
Mr = 364.42	Dx = 1.412 Mg m−3
Monoclinic, P21/n	Melting point: 445 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.6447 (3) Å	Cell parameters from 4233 reflections
b = 7.1680 (2) Å	θ = 2.2–28.0°
c = 19.2382 (5) Å	µ = 0.21 mm−1
β = 100.592 (2)°	T = 173 K
V = 1713.99 (8) Å3	Block, colourless
Z = 4	0.38 × 0.25 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	4269 independent reflections
Radiation source: rotating anode	3406 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.037
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→9
Tmin = 0.684, Tmax = 0.746	l = −25→25
16390 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F2) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0567P)2 + 1.1638P] where P = (Fo2 + 2Fc2)/3
4269 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.41 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	0.28388 (4)	0.20679 (7)	0.65076 (2)	0.02778 (14)
F1	−0.08545 (10)	0.2673 (2)	0.49260 (7)	0.0538 (4)
O1	0.37450 (10)	0.22928 (19)	0.46484 (6)	0.0258 (3)
O2	0.34178 (13)	0.0589 (2)	0.69642 (8)	0.0450 (4)
C1	0.34858 (14)	0.2327 (2)	0.57766 (9)	0.0218 (3)
C2	0.46328 (14)	0.2461 (2)	0.57892 (9)	0.0216 (3)
C3	0.55575 (14)	0.2587 (2)	0.63076 (9)	0.0224 (3)
H3	0.5509	0.2585	0.6795	0.027*
C4	0.65569 (14)	0.2718 (2)	0.61010 (9)	0.0221 (3)
C5	0.66128 (15)	0.2675 (3)	0.53742 (9)	0.0267 (4)
H5	0.7297	0.2752	0.5239	0.032*
C6	0.57064 (15)	0.2525 (3)	0.48550 (9)	0.0277 (4)
H6	0.5751	0.2484	0.4368	0.033*
C7	0.47340 (14)	0.2437 (2)	0.50788 (9)	0.0231 (4)
C8	0.29968 (14)	0.2219 (2)	0.50834 (9)	0.0234 (4)
C9	0.75598 (14)	0.2881 (2)	0.66393 (9)	0.0221 (3)
C10	0.84465 (15)	0.3880 (3)	0.64995 (9)	0.0265 (4)
H10	0.8411	0.4457	0.6051	0.032*
C11	0.93742 (15)	0.4040 (3)	0.70038 (10)	0.0301 (4)
H11	0.9968	0.4728	0.6899	0.036*
C12	0.94449 (16)	0.3206 (3)	0.76596 (10)	0.0304 (4)
H12	1.0082	0.3325	0.8006	0.037*
C13	0.85745 (16)	0.2192 (3)	0.78057 (10)	0.0278 (4)
H13	0.8617	0.1605	0.8253	0.033*
C14	0.76453 (15)	0.2037 (3)	0.73008 (9)	0.0249 (4)
H14	0.7055	0.1342	0.7407	0.030*
C15	0.18887 (15)	0.1985 (2)	0.47093 (9)	0.0243 (4)
C16	0.10093 (16)	0.2510 (3)	0.50082 (10)	0.0309 (4)
H16	0.1107	0.3089	0.5460	0.037*
C17	−0.00028 (16)	0.2166 (3)	0.46299 (11)	0.0339 (4)
C18	−0.01985 (16)	0.1354 (3)	0.39756 (11)	0.0353 (4)
H18	−0.0913	0.1122	0.3736	0.042*
C19	0.06749 (16)	0.0883 (3)	0.36737 (10)	0.0341 (4)
H19	0.0563	0.0333	0.3217	0.041*
C20	0.17108 (15)	0.1205 (3)	0.40320 (9)	0.0284 (4)
H20	0.2306	0.0895	0.3816	0.034*
C21	0.32241 (17)	0.4276 (3)	0.69310 (10)	0.0336 (4)
H21A	0.3068	0.4261	0.7417	0.040*
H21B	0.4008	0.4462	0.6965	0.040*
C22	0.26270 (18)	0.5865 (3)	0.65229 (12)	0.0397 (5)
H22A	0.2734	0.5820	0.6031	0.060*
H22B	0.2900	0.7052	0.6737	0.060*
H22C	0.1858	0.5758	0.6535	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0303 (3)	0.0299 (2)	0.0262 (2)	0.00221 (19)	0.01334 (18)	0.00413 (18)
F1	0.0266 (7)	0.0891 (12)	0.0475 (8)	0.0094 (7)	0.0112 (6)	−0.0037 (7)
O1	0.0228 (6)	0.0364 (7)	0.0189 (6)	−0.0008 (5)	0.0053 (5)	−0.0013 (5)
O2	0.0521 (10)	0.0453 (9)	0.0417 (8)	0.0148 (8)	0.0195 (7)	0.0176 (7)
C1	0.0214 (8)	0.0244 (8)	0.0203 (7)	0.0006 (7)	0.0061 (6)	0.0004 (6)
C2	0.0231 (9)	0.0229 (8)	0.0202 (7)	0.0005 (7)	0.0079 (6)	−0.0005 (6)
C3	0.0255 (9)	0.0243 (8)	0.0183 (7)	0.0006 (7)	0.0065 (6)	−0.0003 (6)
C4	0.0233 (9)	0.0220 (8)	0.0216 (8)	0.0017 (7)	0.0052 (7)	0.0002 (6)
C5	0.0235 (9)	0.0345 (10)	0.0242 (8)	0.0002 (7)	0.0101 (7)	0.0018 (7)
C6	0.0273 (9)	0.0387 (10)	0.0187 (8)	−0.0007 (8)	0.0088 (7)	−0.0005 (7)
C7	0.0231 (9)	0.0273 (9)	0.0188 (8)	−0.0001 (7)	0.0039 (6)	−0.0008 (6)
C8	0.0243 (9)	0.0238 (8)	0.0235 (8)	0.0016 (7)	0.0082 (7)	−0.0002 (6)
C9	0.0235 (8)	0.0217 (8)	0.0220 (8)	0.0012 (7)	0.0067 (6)	−0.0022 (6)
C10	0.0283 (9)	0.0270 (9)	0.0256 (8)	−0.0001 (7)	0.0091 (7)	0.0016 (7)
C11	0.0250 (9)	0.0299 (9)	0.0365 (10)	−0.0043 (8)	0.0085 (8)	−0.0018 (8)
C12	0.0260 (9)	0.0324 (10)	0.0310 (9)	0.0007 (8)	0.0002 (7)	−0.0042 (8)
C13	0.0302 (10)	0.0284 (9)	0.0243 (8)	0.0018 (8)	0.0034 (7)	0.0009 (7)
C14	0.0255 (9)	0.0255 (9)	0.0243 (8)	−0.0015 (7)	0.0058 (7)	−0.0002 (7)
C15	0.0253 (9)	0.0227 (8)	0.0245 (8)	0.0010 (7)	0.0038 (7)	0.0018 (7)
C16	0.0269 (10)	0.0389 (11)	0.0268 (9)	0.0027 (8)	0.0043 (7)	−0.0007 (8)
C17	0.0244 (9)	0.0425 (11)	0.0356 (10)	0.0052 (8)	0.0076 (8)	0.0047 (9)
C18	0.0269 (10)	0.0356 (11)	0.0393 (10)	−0.0013 (8)	−0.0044 (8)	0.0015 (9)
C19	0.0343 (11)	0.0340 (10)	0.0305 (9)	0.0032 (8)	−0.0033 (8)	−0.0045 (8)
C20	0.0291 (10)	0.0288 (9)	0.0266 (8)	0.0036 (8)	0.0033 (7)	−0.0026 (7)
C21	0.0339 (11)	0.0419 (11)	0.0260 (9)	0.0044 (9)	0.0083 (8)	−0.0070 (8)
C22	0.0455 (13)	0.0325 (11)	0.0445 (12)	0.0029 (9)	0.0172 (10)	−0.0007 (9)

S1—O2	1.4817 (15)	C11—C12	1.384 (3)
S1—C1	1.7620 (17)	C11—H11	0.9500
S1—C21	1.805 (2)	C12—C13	1.390 (3)
F1—C17	1.357 (2)	C12—H12	0.9500
O1—C7	1.371 (2)	C13—C14	1.385 (3)
O1—C8	1.375 (2)	C13—H13	0.9500
C1—C8	1.365 (2)	C14—H14	0.9500
C1—C2	1.449 (2)	C15—C16	1.394 (3)
C2—C3	1.393 (2)	C15—C20	1.397 (2)
C2—C7	1.396 (2)	C16—C17	1.373 (3)
C3—C4	1.396 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.368 (3)
C4—C5	1.413 (2)	C18—C19	1.381 (3)
C4—C9	1.487 (2)	C18—H18	0.9500
C5—C6	1.379 (3)	C19—C20	1.383 (3)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.377 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.506 (3)
C8—C15	1.462 (2)	C21—H21A	0.9900
C9—C14	1.395 (2)	C21—H21B	0.9900
C9—C10	1.397 (2)	C22—H22A	0.9800
C10—C11	1.383 (3)	C22—H22B	0.9800
C10—H10	0.9500	C22—H22C	0.9800
O2—S1—C1	107.30 (8)	C11—C12—H12	120.4
O2—S1—C21	107.26 (10)	C13—C12—H12	120.4
C1—S1—C21	98.12 (9)	C14—C13—C12	120.11 (17)
C7—O1—C8	106.78 (13)	C14—C13—H13	119.9
C8—C1—C2	107.00 (15)	C12—C13—H13	119.9
C8—C1—S1	125.46 (14)	C13—C14—C9	121.22 (17)
C2—C1—S1	127.14 (13)	C13—C14—H14	119.4
C3—C2—C7	119.06 (16)	C9—C14—H14	119.4
C3—C2—C1	136.21 (15)	C16—C15—C20	119.25 (17)
C7—C2—C1	104.74 (15)	C16—C15—C8	122.05 (16)
C2—C3—C4	119.01 (15)	C20—C15—C8	118.70 (16)
C2—C3—H3	120.5	C17—C16—C15	117.98 (18)
C4—C3—H3	120.5	C17—C16—H16	121.0
C3—C4—C5	119.53 (16)	C15—C16—H16	121.0
C3—C4—C9	120.51 (15)	F1—C17—C18	118.49 (18)
C5—C4—C9	119.96 (16)	F1—C17—C16	117.62 (19)
C6—C5—C4	122.15 (17)	C18—C17—C16	123.88 (19)
C6—C5—H5	118.9	C17—C18—C19	117.90 (18)
C4—C5—H5	118.9	C17—C18—H18	121.1
C7—C6—C5	116.63 (16)	C19—C18—H18	121.1
C7—C6—H6	121.7	C18—C19—C20	120.46 (18)
C5—C6—H6	121.7	C18—C19—H19	119.8
O1—C7—C6	125.62 (15)	C20—C19—H19	119.8
O1—C7—C2	110.77 (15)	C19—C20—C15	120.47 (18)
C6—C7—C2	123.60 (16)	C19—C20—H20	119.8
C1—C8—O1	110.71 (15)	C15—C20—H20	119.8
C1—C8—C15	135.10 (16)	C22—C21—S1	111.11 (14)
O1—C8—C15	114.15 (14)	C22—C21—H21A	109.4
C14—C9—C10	117.87 (16)	S1—C21—H21A	109.4
C14—C9—C4	120.94 (16)	C22—C21—H21B	109.4
C10—C9—C4	121.19 (15)	S1—C21—H21B	109.4
C11—C10—C9	120.98 (16)	H21A—C21—H21B	108.0
C11—C10—H10	119.5	C21—C22—H22A	109.5
C9—C10—H10	119.5	C21—C22—H22B	109.5
C10—C11—C12	120.53 (17)	H22A—C22—H22B	109.5
C10—C11—H11	119.7	C21—C22—H22C	109.5
C12—C11—H11	119.7	H22A—C22—H22C	109.5
C11—C12—C13	119.29 (18)	H22B—C22—H22C	109.5
O2—S1—C1—C8	125.48 (17)	C3—C4—C9—C14	31.9 (2)
C21—S1—C1—C8	−123.52 (17)	C5—C4—C9—C14	−147.46 (18)
O2—S1—C1—C2	−46.25 (18)	C3—C4—C9—C10	−148.25 (17)
C21—S1—C1—C2	64.74 (17)	C5—C4—C9—C10	32.4 (2)
C8—C1—C2—C3	−179.2 (2)	C14—C9—C10—C11	−0.6 (3)
S1—C1—C2—C3	−6.2 (3)	C4—C9—C10—C11	179.48 (16)
C8—C1—C2—C7	0.57 (19)	C9—C10—C11—C12	0.2 (3)
S1—C1—C2—C7	173.54 (14)	C10—C11—C12—C13	0.4 (3)
C7—C2—C3—C4	1.0 (2)	C11—C12—C13—C14	−0.6 (3)
C1—C2—C3—C4	−179.22 (19)	C12—C13—C14—C9	0.1 (3)
C2—C3—C4—C5	−1.5 (3)	C10—C9—C14—C13	0.5 (3)
C2—C3—C4—C9	179.17 (15)	C4—C9—C14—C13	−179.62 (16)
C3—C4—C5—C6	0.6 (3)	C1—C8—C15—C16	25.1 (3)
C9—C4—C5—C6	179.99 (17)	O1—C8—C15—C16	−157.38 (17)
C4—C5—C6—C7	0.6 (3)	C1—C8—C15—C20	−154.7 (2)
C8—O1—C7—C6	179.11 (18)	O1—C8—C15—C20	22.8 (2)
C8—O1—C7—C2	−0.12 (19)	C20—C15—C16—C17	2.5 (3)
C5—C6—C7—O1	179.75 (17)	C8—C15—C16—C17	−177.30 (18)
C5—C6—C7—C2	−1.1 (3)	C15—C16—C17—F1	179.68 (18)
C3—C2—C7—O1	179.53 (15)	C15—C16—C17—C18	−0.6 (3)
C1—C2—C7—O1	−0.28 (19)	F1—C17—C18—C19	178.58 (19)
C3—C2—C7—C6	0.3 (3)	C16—C17—C18—C19	−1.1 (3)
C1—C2—C7—C6	−179.53 (18)	C17—C18—C19—C20	0.9 (3)
C2—C1—C8—O1	−0.7 (2)	C18—C19—C20—C15	1.0 (3)
S1—C1—C8—O1	−173.79 (12)	C16—C15—C20—C19	−2.8 (3)
C2—C1—C8—C15	176.92 (19)	C8—C15—C20—C19	177.05 (17)
S1—C1—C8—C15	3.8 (3)	O2—S1—C21—C22	−176.95 (14)
C7—O1—C8—C1	0.5 (2)	C1—S1—C21—C22	72.02 (15)
C7—O1—C8—C15	−177.63 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.49	3.166 (3)	128
C21—H21A···O2ii	0.99	2.58	3.367 (3)	136
C14—H14···Cg1iii	0.95	2.66	3.466 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.49	3.166 (3)	128
C21—H21A⋯O2ii	0.99	2.58	3.367 (3)	136
C14—H14⋯Cg1iii	0.95	2.66	3.466 (3)	143

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