2-(4-Fluoro-phen-yl)-5-iodo-7-methyl-3-phenyl-sulfinyl-1-benzo-furan.

In the title compound, C21H14FIO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzo-furan fragment and the pendant 4-fluoro-phenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal, mol-ecules are linked by pairs of C-H⋯I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C-H⋯O hydrogen bonds. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [2.9627 (14) Å] involving the sulfinyl groups.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶, 2012 ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008 ▶) and for a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C21H14FIO2S

M = 476.28

Triclinic,

a = 8.1060 (3) Å

b = 10.7771 (4) Å

c = 11.2639 (4) Å

α = 71.814 (2)°

β = 74.496 (2)°

γ = 79.038 (2)°

V = 894.69 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.93 mm−1

T = 173 K

0.36 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.562, T max = 0.746

16292 measured reflections

4404 independent reflections

4125 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.062

S = 1.05

4404 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.63 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011793/ld2102sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011793/ld2102Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011793/ld2102Isup3.cml

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

C21H14FIO2S	Z = 2
Mr = 476.28	F(000) = 468
Triclinic, P1	Dx = 1.768 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1060 (3) Å	Cell parameters from 6652 reflections
b = 10.7771 (4) Å	θ = 2.6–28.4°
c = 11.2639 (4) Å	µ = 1.93 mm−1
α = 71.814 (2)°	T = 173 K
β = 74.496 (2)°	Block, colourless
γ = 79.038 (2)°	0.36 × 0.28 × 0.19 mm
V = 894.69 (6) Å3

Bruker SMART APEXII CCD diffractometer	4404 independent reflections
Radiation source: rotating anode	4125 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.562, Tmax = 0.746	l = −14→14
16292 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)] = 0.023	Hydrogen site location: difference Fourier map
wR(F2) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0291P)2 + 0.4238P] where P = (Fo2 + 2Fc2)/3
4404 reflections	(Δ/σ)max = 0.002
236 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.63 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
I1	1.038283 (17)	0.207761 (13)	1.022854 (12)	0.03450 (6)
S1	0.88164 (6)	0.15272 (4)	0.52014 (4)	0.02267 (9)
F1	0.52793 (19)	0.62193 (14)	0.03604 (12)	0.0432 (3)
O1	0.76006 (17)	0.52135 (12)	0.54415 (12)	0.0240 (3)
O2	1.03200 (17)	0.08292 (13)	0.57680 (14)	0.0297 (3)
C1	0.8377 (2)	0.30667 (17)	0.55547 (17)	0.0219 (3)
C2	0.8726 (2)	0.32977 (17)	0.66597 (17)	0.0226 (3)
C3	0.9380 (2)	0.25313 (18)	0.77187 (18)	0.0256 (4)
H3	0.9754	0.1619	0.7836	0.031*
C4	0.9455 (2)	0.31737 (19)	0.85932 (18)	0.0263 (4)
C5	0.8945 (3)	0.45161 (19)	0.84379 (18)	0.0274 (4)
H5	0.9038	0.4903	0.9065	0.033*
C6	0.8304 (2)	0.52953 (18)	0.73849 (18)	0.0256 (4)
C7	0.8216 (2)	0.46343 (17)	0.65298 (17)	0.0232 (3)
C8	0.7708 (2)	0.42461 (17)	0.48521 (17)	0.0224 (3)
C9	0.7725 (3)	0.67397 (19)	0.7182 (2)	0.0336 (4)
H9A	0.7783	0.7163	0.6267	0.050*
H9B	0.8479	0.7132	0.7480	0.050*
H9C	0.6536	0.6868	0.7665	0.050*
C10	0.7072 (2)	0.47139 (17)	0.36758 (17)	0.0234 (3)
C11	0.7151 (3)	0.39187 (19)	0.28875 (19)	0.0285 (4)
H11	0.7626	0.3024	0.3120	0.034*
C12	0.6542 (3)	0.4420 (2)	0.17688 (19)	0.0313 (4)
H12	0.6595	0.3880	0.1233	0.038*
C13	0.5866 (3)	0.5714 (2)	0.14591 (18)	0.0305 (4)
C14	0.5757 (3)	0.6538 (2)	0.22019 (19)	0.0315 (4)
H14	0.5279	0.7431	0.1958	0.038*
C15	0.6363 (3)	0.60277 (19)	0.33112 (18)	0.0287 (4)
H15	0.6298	0.6580	0.3839	0.034*
C16	0.6935 (2)	0.08351 (17)	0.62724 (19)	0.0253 (4)
C17	0.7012 (3)	0.0107 (2)	0.7511 (2)	0.0351 (4)
H17	0.8053	−0.0028	0.7794	0.042*
C18	0.5561 (3)	−0.0422 (2)	0.8336 (3)	0.0457 (6)
H18	0.5598	−0.0921	0.9191	0.055*
C19	0.4053 (3)	−0.0223 (2)	0.7911 (3)	0.0484 (6)
H19	0.3053	−0.0579	0.8481	0.058*
C20	0.3990 (3)	0.0487 (3)	0.6670 (3)	0.0465 (6)
H20	0.2952	0.0611	0.6385	0.056*
C21	0.5442 (3)	0.1020 (2)	0.5834 (2)	0.0343 (4)
H21	0.5411	0.1505	0.4975	0.041*

	U11	U22	U33	U12	U13	U23
I1	0.03624 (9)	0.04058 (9)	0.02868 (8)	−0.00585 (6)	−0.01368 (6)	−0.00611 (6)
S1	0.0228 (2)	0.01980 (19)	0.0283 (2)	0.00242 (16)	−0.00949 (17)	−0.01045 (16)
F1	0.0501 (8)	0.0477 (7)	0.0309 (6)	−0.0013 (6)	−0.0206 (6)	−0.0025 (5)
O1	0.0290 (7)	0.0186 (6)	0.0250 (6)	−0.0013 (5)	−0.0063 (5)	−0.0078 (5)
O2	0.0234 (6)	0.0282 (7)	0.0422 (8)	0.0057 (5)	−0.0148 (6)	−0.0153 (6)
C1	0.0216 (8)	0.0206 (8)	0.0248 (8)	−0.0013 (6)	−0.0050 (7)	−0.0091 (6)
C2	0.0213 (8)	0.0227 (8)	0.0259 (8)	−0.0038 (6)	−0.0048 (7)	−0.0092 (7)
C3	0.0254 (9)	0.0249 (8)	0.0288 (9)	−0.0039 (7)	−0.0085 (7)	−0.0077 (7)
C4	0.0248 (9)	0.0311 (9)	0.0241 (9)	−0.0067 (7)	−0.0074 (7)	−0.0056 (7)
C5	0.0277 (9)	0.0314 (9)	0.0269 (9)	−0.0091 (8)	−0.0030 (7)	−0.0126 (7)
C6	0.0275 (9)	0.0243 (8)	0.0264 (9)	−0.0079 (7)	−0.0016 (7)	−0.0098 (7)
C7	0.0235 (8)	0.0226 (8)	0.0237 (8)	−0.0042 (7)	−0.0031 (7)	−0.0076 (7)
C8	0.0218 (8)	0.0217 (8)	0.0246 (8)	−0.0024 (6)	−0.0025 (7)	−0.0099 (7)
C9	0.0434 (12)	0.0249 (9)	0.0352 (10)	−0.0051 (8)	−0.0064 (9)	−0.0135 (8)
C10	0.0221 (8)	0.0227 (8)	0.0237 (8)	−0.0007 (7)	−0.0031 (7)	−0.0067 (7)
C11	0.0322 (10)	0.0255 (9)	0.0281 (9)	0.0015 (7)	−0.0095 (8)	−0.0083 (7)
C12	0.0342 (10)	0.0354 (10)	0.0260 (9)	−0.0029 (8)	−0.0076 (8)	−0.0110 (8)
C13	0.0279 (9)	0.0365 (10)	0.0236 (9)	−0.0027 (8)	−0.0078 (8)	−0.0022 (8)
C14	0.0312 (10)	0.0271 (9)	0.0303 (10)	0.0030 (8)	−0.0073 (8)	−0.0031 (8)
C15	0.0312 (10)	0.0255 (9)	0.0273 (9)	0.0001 (7)	−0.0050 (8)	−0.0076 (7)
C16	0.0244 (9)	0.0195 (8)	0.0358 (10)	0.0003 (7)	−0.0100 (8)	−0.0121 (7)
C17	0.0366 (11)	0.0256 (9)	0.0420 (12)	−0.0042 (8)	−0.0141 (9)	−0.0031 (8)
C18	0.0474 (14)	0.0339 (11)	0.0486 (14)	−0.0100 (10)	−0.0034 (11)	−0.0043 (10)
C19	0.0365 (12)	0.0406 (13)	0.0661 (17)	−0.0133 (10)	0.0050 (12)	−0.0207 (12)
C20	0.0274 (11)	0.0477 (13)	0.0755 (18)	−0.0037 (9)	−0.0134 (11)	−0.0312 (13)
C21	0.0285 (10)	0.0350 (10)	0.0471 (12)	0.0010 (8)	−0.0162 (9)	−0.0186 (9)

I1—C4	2.0974 (19)	C9—H9C	0.9800
S1—O2i	2.9627 (14)	C10—C11	1.397 (3)
S1—O2	1.4920 (14)	C10—C15	1.399 (3)
S1—C1	1.7748 (17)	C11—C12	1.389 (3)
S1—C16	1.796 (2)	C11—H11	0.9500
F1—C13	1.360 (2)	C12—C13	1.369 (3)
O1—C7	1.368 (2)	C12—H12	0.9500
O1—C8	1.379 (2)	C13—C14	1.375 (3)
C1—C8	1.369 (2)	C14—C15	1.379 (3)
C1—C2	1.449 (2)	C14—H14	0.9500
C2—C7	1.393 (2)	C15—H15	0.9500
C2—C3	1.394 (3)	C16—C17	1.382 (3)
C3—C4	1.388 (3)	C16—C21	1.383 (3)
C3—H3	0.9500	C17—C18	1.383 (3)
C4—C5	1.396 (3)	C17—H17	0.9500
C5—C6	1.387 (3)	C18—C19	1.385 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.387 (2)	C19—C20	1.378 (4)
C6—C9	1.501 (3)	C19—H19	0.9500
C8—C10	1.458 (3)	C20—C21	1.390 (3)
C9—H9A	0.9800	C20—H20	0.9500
C9—H9B	0.9800	C21—H21	0.9500
O2—S1—C1	105.04 (8)	C11—C10—C15	118.34 (17)
O2—S1—C16	106.95 (9)	C11—C10—C8	123.24 (16)
C1—S1—C16	97.02 (8)	C15—C10—C8	118.41 (16)
O2—S1—O2i	78.36 (6)	C12—C11—C10	120.83 (18)
C1—S1—O2i	172.01 (7)	C12—C11—H11	119.6
C16—S1—O2i	88.76 (6)	C10—C11—H11	119.6
C7—O1—C8	107.21 (13)	C13—C12—C11	118.25 (19)
C8—C1—C2	107.21 (15)	C13—C12—H12	120.9
C8—C1—S1	127.99 (14)	C11—C12—H12	120.9
C2—C1—S1	124.78 (13)	F1—C13—C12	118.80 (19)
C7—C2—C3	119.35 (17)	F1—C13—C14	117.99 (18)
C7—C2—C1	104.84 (16)	C12—C13—C14	123.21 (19)
C3—C2—C1	135.81 (17)	C13—C14—C15	117.99 (18)
C4—C3—C2	116.34 (17)	C13—C14—H14	121.0
C4—C3—H3	121.8	C15—C14—H14	121.0
C2—C3—H3	121.8	C14—C15—C10	121.38 (18)
C3—C4—C5	123.24 (18)	C14—C15—H15	119.3
C3—C4—I1	118.53 (14)	C10—C15—H15	119.3
C5—C4—I1	118.23 (14)	C17—C16—C21	121.16 (19)
C6—C5—C4	121.18 (17)	C17—C16—S1	119.54 (15)
C6—C5—H5	119.4	C21—C16—S1	119.29 (16)
C4—C5—H5	119.4	C16—C17—C18	119.5 (2)
C5—C6—C7	114.83 (17)	C16—C17—H17	120.3
C5—C6—C9	123.14 (17)	C18—C17—H17	120.3
C7—C6—C9	122.02 (18)	C17—C18—C19	119.7 (2)
O1—C7—C6	124.22 (16)	C17—C18—H18	120.1
O1—C7—C2	110.72 (15)	C19—C18—H18	120.1
C6—C7—C2	125.06 (18)	C20—C19—C18	120.6 (2)
C1—C8—O1	110.02 (16)	C20—C19—H19	119.7
C1—C8—C10	136.31 (16)	C18—C19—H19	119.7
O1—C8—C10	113.67 (15)	C19—C20—C21	120.1 (2)
C6—C9—H9A	109.5	C19—C20—H20	120.0
C6—C9—H9B	109.5	C21—C20—H20	120.0
H9A—C9—H9B	109.5	C16—C21—C20	119.0 (2)
C6—C9—H9C	109.5	C16—C21—H21	120.5
H9A—C9—H9C	109.5	C20—C21—H21	120.5
H9B—C9—H9C	109.5
O2—S1—C1—C8	149.12 (17)	S1—C1—C8—C10	2.6 (3)
C16—S1—C1—C8	−101.17 (18)	C7—O1—C8—C1	0.17 (19)
O2—S1—C1—C2	−28.97 (18)	C7—O1—C8—C10	179.24 (15)
C16—S1—C1—C2	80.74 (17)	C1—C8—C10—C11	−5.0 (3)
C8—C1—C2—C7	0.3 (2)	O1—C8—C10—C11	176.23 (17)
S1—C1—C2—C7	178.71 (13)	C1—C8—C10—C15	175.6 (2)
C8—C1—C2—C3	179.5 (2)	O1—C8—C10—C15	−3.1 (2)
S1—C1—C2—C3	−2.1 (3)	C15—C10—C11—C12	0.1 (3)
C7—C2—C3—C4	0.8 (3)	C8—C10—C11—C12	−179.26 (18)
C1—C2—C3—C4	−178.3 (2)	C10—C11—C12—C13	0.1 (3)
C2—C3—C4—C5	−1.2 (3)	C11—C12—C13—F1	179.46 (18)
C2—C3—C4—I1	178.91 (13)	C11—C12—C13—C14	−0.1 (3)
C3—C4—C5—C6	0.7 (3)	F1—C13—C14—C15	−179.55 (18)
I1—C4—C5—C6	−179.40 (14)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	0.2 (3)	C13—C14—C15—C10	0.1 (3)
C4—C5—C6—C9	179.44 (18)	C11—C10—C15—C14	−0.2 (3)
C8—O1—C7—C6	−179.63 (17)	C8—C10—C15—C14	179.19 (18)
C8—O1—C7—C2	0.02 (19)	O2—S1—C16—C17	16.79 (18)
C5—C6—C7—O1	178.99 (16)	C1—S1—C16—C17	−91.31 (16)
C9—C6—C7—O1	−0.2 (3)	O2—S1—C16—C21	−162.03 (15)
C5—C6—C7—C2	−0.6 (3)	C1—S1—C16—C21	89.87 (16)
C9—C6—C7—C2	−179.84 (18)	C21—C16—C17—C18	−1.4 (3)
C3—C2—C7—O1	−179.54 (16)	S1—C16—C17—C18	179.85 (17)
C1—C2—C7—O1	−0.2 (2)	C16—C17—C18—C19	0.3 (3)
C3—C2—C7—C6	0.1 (3)	C17—C18—C19—C20	0.7 (4)
C1—C2—C7—C6	179.46 (17)	C18—C19—C20—C21	−0.6 (4)
C2—C1—C8—O1	−0.3 (2)	C17—C16—C21—C20	1.5 (3)
S1—C1—C8—O1	−178.64 (13)	S1—C16—C21—C20	−179.72 (16)
C2—C1—C8—C10	−179.0 (2)	C19—C20—C21—C16	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ii	0.95	2.36	3.314 (3)	177
C17—H17···I1iii	0.95	2.97	3.705 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.95	2.36	3.314 (3)	177
C17—H17⋯I1ii	0.95	2.97	3.705 (2)	135

Symmetry codes: (i) ; (ii) .