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

In the title compound, C21H14F2O2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzo-furan ring system and the pendant 4-fluoro-phenyl and phenyl rings are 5.93 (9) and 80.23 (5)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C21H14F2O2S

M = 368.38

Monoclinic,

a = 12.3698 (8) Å

b = 7.9967 (5) Å

c = 17.4195 (10) Å

β = 100.323 (4)°

V = 1695.20 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.30 × 0.26 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.655, T max = 0.746

30145 measured reflections

4267 independent reflections

3147 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.04

4267 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.29 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/S1600536813017583/gg2118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017583/gg2118Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017583/gg2118Isup3.cml

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

C21H14F2O2S	F(000) = 760
Mr = 368.38	Dx = 1.443 Mg m−3
Monoclinic, P21/n	Melting point = 466–467 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.3698 (8) Å	Cell parameters from 6581 reflections
b = 7.9967 (5) Å	θ = 2.2–27.5°
c = 17.4195 (10) Å	µ = 0.22 mm−1
β = 100.323 (4)°	T = 173 K
V = 1695.20 (18) Å3	Block, colourless
Z = 4	0.30 × 0.26 × 0.10 mm

Bruker SMART APEXII CCD diffractometer	4267 independent reflections
Radiation source: rotating anode	3147 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.065
Detector resolution: 10.0 pixels mm-1	θmax = 28.5°, θmin = 1.9°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.655, Tmax = 0.746	l = −23→23
30145 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.6509P] where P = (Fo2 + 2Fc2)/3
4267 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.29 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	0.75286 (4)	0.76155 (6)	0.66805 (2)	0.02982 (13)
F1	0.88756 (12)	1.08879 (19)	0.40581 (8)	0.0604 (4)
F2	0.24627 (11)	0.3963 (2)	0.67822 (8)	0.0594 (4)
O1	0.52531 (10)	0.79604 (17)	0.47682 (6)	0.0331 (3)
O2	0.82873 (12)	0.90671 (18)	0.68234 (8)	0.0421 (4)
C1	0.66892 (15)	0.7947 (2)	0.57601 (9)	0.0293 (4)
C2	0.70298 (15)	0.8786 (2)	0.51067 (9)	0.0308 (4)
C3	0.79965 (17)	0.9521 (3)	0.49652 (11)	0.0368 (4)
H3	0.8643	0.9575	0.5352	0.044*
C4	0.79512 (19)	1.0161 (3)	0.42283 (12)	0.0420 (5)
C5	0.70310 (19)	1.0131 (3)	0.36455 (11)	0.0426 (5)
H5	0.7061	1.0612	0.3151	0.051*
C6	0.60661 (18)	0.9404 (3)	0.37787 (10)	0.0372 (5)
C7	0.61135 (16)	0.8754 (2)	0.45189 (10)	0.0317 (4)
C8	0.56166 (15)	0.7471 (2)	0.55269 (9)	0.0295 (4)
C9	0.50397 (19)	0.9291 (3)	0.31700 (11)	0.0468 (6)
H9A	0.4979	0.8165	0.2944	0.070*
H9B	0.5074	1.0114	0.2759	0.070*
H9C	0.4397	0.9519	0.3411	0.070*
C10	0.48089 (15)	0.6561 (2)	0.58759 (10)	0.0310 (4)
C11	0.49926 (16)	0.6069 (3)	0.66553 (11)	0.0388 (5)
H11	0.5674	0.6330	0.6980	0.047*
C12	0.42033 (17)	0.5211 (3)	0.69639 (12)	0.0433 (5)
H12	0.4332	0.4885	0.7497	0.052*
C13	0.32297 (17)	0.4839 (3)	0.64853 (12)	0.0412 (5)
C14	0.30143 (17)	0.5288 (3)	0.57126 (12)	0.0448 (5)
H14	0.2335	0.5001	0.5392	0.054*
C15	0.37990 (16)	0.6160 (3)	0.54113 (11)	0.0374 (5)
H15	0.3654	0.6496	0.4880	0.045*
C16	0.83023 (15)	0.5900 (2)	0.64087 (9)	0.0285 (4)
C17	0.92867 (16)	0.6178 (3)	0.61585 (11)	0.0404 (5)
H17	0.9549	0.7281	0.6105	0.049*
C18	0.9876 (2)	0.4805 (4)	0.59885 (13)	0.0560 (7)
H18	1.0550	0.4967	0.5809	0.067*
C19	0.9509 (2)	0.3218 (4)	0.60738 (13)	0.0593 (7)
H19	0.9931	0.2291	0.5957	0.071*
C20	0.8531 (2)	0.2952 (3)	0.63286 (12)	0.0502 (6)
H20	0.8274	0.1846	0.6382	0.060*
C21	0.79281 (17)	0.4303 (2)	0.65049 (10)	0.0346 (4)
H21	0.7260	0.4136	0.6691	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0319 (2)	0.0365 (3)	0.01842 (18)	−0.0017 (2)	−0.00255 (15)	−0.00149 (16)
F1	0.0605 (9)	0.0742 (10)	0.0490 (7)	−0.0177 (8)	0.0169 (7)	0.0140 (7)
F2	0.0472 (8)	0.0810 (11)	0.0534 (8)	−0.0180 (7)	0.0181 (6)	−0.0046 (7)
O1	0.0336 (7)	0.0419 (8)	0.0206 (5)	0.0028 (6)	−0.0039 (5)	0.0011 (5)
O2	0.0475 (9)	0.0385 (8)	0.0342 (7)	−0.0110 (7)	−0.0085 (6)	−0.0043 (6)
C1	0.0323 (9)	0.0332 (10)	0.0203 (7)	0.0009 (8)	−0.0009 (7)	0.0005 (6)
C2	0.0355 (10)	0.0335 (10)	0.0220 (7)	0.0032 (8)	0.0010 (7)	−0.0006 (7)
C3	0.0402 (11)	0.0401 (11)	0.0291 (8)	−0.0035 (9)	0.0038 (8)	0.0001 (8)
C4	0.0492 (13)	0.0424 (12)	0.0364 (10)	−0.0045 (10)	0.0131 (9)	0.0019 (9)
C5	0.0597 (14)	0.0422 (12)	0.0262 (8)	0.0027 (11)	0.0089 (9)	0.0048 (8)
C6	0.0512 (12)	0.0358 (11)	0.0226 (8)	0.0083 (9)	0.0009 (8)	−0.0005 (7)
C7	0.0365 (10)	0.0335 (10)	0.0237 (8)	0.0025 (8)	0.0017 (7)	−0.0010 (7)
C8	0.0319 (9)	0.0346 (10)	0.0195 (7)	0.0048 (8)	−0.0020 (6)	−0.0018 (7)
C9	0.0606 (15)	0.0510 (13)	0.0233 (8)	0.0095 (11)	−0.0073 (9)	0.0016 (8)
C10	0.0282 (9)	0.0351 (10)	0.0282 (8)	0.0040 (8)	0.0010 (7)	−0.0048 (7)
C11	0.0316 (10)	0.0525 (13)	0.0297 (9)	−0.0033 (9)	−0.0020 (7)	0.0011 (8)
C12	0.0386 (12)	0.0578 (14)	0.0330 (9)	−0.0011 (10)	0.0050 (8)	0.0044 (9)
C13	0.0334 (11)	0.0481 (13)	0.0445 (11)	−0.0044 (9)	0.0135 (9)	−0.0064 (9)
C14	0.0311 (11)	0.0622 (15)	0.0398 (10)	−0.0052 (10)	0.0031 (8)	−0.0127 (10)
C15	0.0307 (10)	0.0519 (13)	0.0276 (8)	0.0014 (9)	−0.0003 (7)	−0.0071 (8)
C16	0.0269 (9)	0.0384 (10)	0.0177 (7)	−0.0006 (8)	−0.0030 (6)	0.0017 (7)
C17	0.0341 (11)	0.0562 (13)	0.0297 (9)	−0.0007 (10)	0.0021 (8)	0.0097 (9)
C18	0.0421 (13)	0.091 (2)	0.0365 (11)	0.0184 (13)	0.0116 (9)	0.0080 (12)
C19	0.0697 (17)	0.0669 (18)	0.0392 (11)	0.0320 (15)	0.0044 (11)	−0.0020 (11)
C20	0.0690 (16)	0.0418 (13)	0.0359 (10)	0.0090 (12)	−0.0012 (10)	−0.0012 (9)
C21	0.0385 (11)	0.0374 (11)	0.0253 (8)	−0.0025 (9)	−0.0010 (7)	0.0021 (7)

S1—O2	1.4855 (14)	C10—C11	1.392 (2)
S1—C1	1.7671 (17)	C10—C15	1.399 (3)
S1—C16	1.7846 (19)	C11—C12	1.379 (3)
F1—C4	1.362 (2)	C11—H11	0.9500
F2—C13	1.354 (2)	C12—C13	1.369 (3)
O1—C8	1.3745 (19)	C12—H12	0.9500
O1—C7	1.375 (2)	C13—C14	1.372 (3)
C1—C8	1.370 (3)	C14—C15	1.374 (3)
C1—C2	1.447 (2)	C14—H14	0.9500
C2—C7	1.385 (2)	C15—H15	0.9500
C2—C3	1.393 (3)	C16—C21	1.378 (3)
C3—C4	1.374 (3)	C16—C17	1.383 (3)
C3—H3	0.9500	C17—C18	1.379 (3)
C4—C5	1.383 (3)	C17—H17	0.9500
C5—C6	1.384 (3)	C18—C19	1.365 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.382 (2)	C19—C20	1.378 (4)
C6—C9	1.504 (3)	C19—H19	0.9500
C8—C10	1.454 (3)	C20—C21	1.379 (3)
C9—H9A	0.9800	C20—H20	0.9500
C9—H9B	0.9800	C21—H21	0.9500
C9—H9C	0.9800
O2—S1—C1	106.59 (8)	C11—C10—C8	122.99 (16)
O2—S1—C16	107.00 (9)	C15—C10—C8	118.84 (16)
C1—S1—C16	97.50 (8)	C12—C11—C10	121.16 (18)
C8—O1—C7	107.27 (14)	C12—C11—H11	119.4
C8—C1—C2	107.38 (15)	C10—C11—H11	119.4
C8—C1—S1	127.41 (14)	C13—C12—C11	118.55 (19)
C2—C1—S1	125.21 (14)	C13—C12—H12	120.7
C7—C2—C3	119.46 (16)	C11—C12—H12	120.7
C7—C2—C1	104.94 (16)	F2—C13—C12	118.68 (19)
C3—C2—C1	135.60 (17)	F2—C13—C14	118.93 (19)
C4—C3—C2	115.45 (18)	C12—C13—C14	122.4 (2)
C4—C3—H3	122.3	C13—C14—C15	118.77 (19)
C2—C3—H3	122.3	C13—C14—H14	120.6
F1—C4—C3	117.86 (19)	C15—C14—H14	120.6
F1—C4—C5	117.40 (18)	C14—C15—C10	120.96 (18)
C3—C4—C5	124.7 (2)	C14—C15—H15	119.5
C4—C5—C6	120.34 (18)	C10—C15—H15	119.5
C4—C5—H5	119.8	C21—C16—C17	121.41 (19)
C6—C5—H5	119.8	C21—C16—S1	118.17 (14)
C7—C6—C5	114.88 (18)	C17—C16—S1	120.28 (16)
C7—C6—C9	121.7 (2)	C18—C17—C16	118.0 (2)
C5—C6—C9	123.46 (17)	C18—C17—H17	121.0
O1—C7—C6	124.24 (17)	C16—C17—H17	121.0
O1—C7—C2	110.63 (15)	C19—C18—C17	121.2 (2)
C6—C7—C2	125.12 (19)	C19—C18—H18	119.4
C1—C8—O1	109.77 (15)	C17—C18—H18	119.4
C1—C8—C10	135.78 (15)	C18—C19—C20	120.5 (2)
O1—C8—C10	114.43 (15)	C18—C19—H19	119.8
C6—C9—H9A	109.5	C20—C19—H19	119.8
C6—C9—H9B	109.5	C19—C20—C21	119.5 (2)
H9A—C9—H9B	109.5	C19—C20—H20	120.3
C6—C9—H9C	109.5	C21—C20—H20	120.3
H9A—C9—H9C	109.5	C16—C21—C20	119.5 (2)
H9B—C9—H9C	109.5	C16—C21—H21	120.3
C11—C10—C15	118.17 (18)	C20—C21—H21	120.3
O2—S1—C1—C8	−147.60 (17)	S1—C1—C8—C10	−1.9 (3)
C16—S1—C1—C8	102.09 (18)	C7—O1—C8—C1	0.2 (2)
O2—S1—C1—C2	32.64 (19)	C7—O1—C8—C10	−178.35 (15)
C16—S1—C1—C2	−77.66 (17)	C1—C8—C10—C11	6.8 (4)
C8—C1—C2—C7	0.2 (2)	O1—C8—C10—C11	−175.11 (18)
S1—C1—C2—C7	−179.97 (14)	C1—C8—C10—C15	−173.3 (2)
C8—C1—C2—C3	−178.9 (2)	O1—C8—C10—C15	4.8 (3)
S1—C1—C2—C3	0.9 (3)	C15—C10—C11—C12	0.0 (3)
C7—C2—C3—C4	−0.3 (3)	C8—C10—C11—C12	179.87 (19)
C1—C2—C3—C4	178.7 (2)	C10—C11—C12—C13	0.4 (3)
C2—C3—C4—F1	−179.76 (18)	C11—C12—C13—F2	178.5 (2)
C2—C3—C4—C5	0.6 (3)	C11—C12—C13—C14	0.1 (4)
F1—C4—C5—C6	179.68 (19)	F2—C13—C14—C15	−179.3 (2)
C3—C4—C5—C6	−0.7 (4)	C12—C13—C14—C15	−0.8 (4)
C4—C5—C6—C7	0.4 (3)	C13—C14—C15—C10	1.2 (3)
C4—C5—C6—C9	−178.7 (2)	C11—C10—C15—C14	−0.7 (3)
C8—O1—C7—C6	179.07 (18)	C8—C10—C15—C14	179.34 (19)
C8—O1—C7—C2	−0.1 (2)	O2—S1—C16—C21	157.93 (13)
C5—C6—C7—O1	−179.11 (18)	C1—S1—C16—C21	−92.11 (14)
C9—C6—C7—O1	0.0 (3)	O2—S1—C16—C17	−17.86 (15)
C5—C6—C7—C2	−0.1 (3)	C1—S1—C16—C17	92.11 (15)
C9—C6—C7—C2	179.01 (19)	C21—C16—C17—C18	1.5 (3)
C3—C2—C7—O1	179.17 (17)	S1—C16—C17—C18	177.18 (15)
C1—C2—C7—O1	−0.1 (2)	C16—C17—C18—C19	−0.9 (3)
C3—C2—C7—C6	0.0 (3)	C17—C18—C19—C20	0.4 (3)
C1—C2—C7—C6	−179.23 (18)	C18—C19—C20—C21	−0.6 (3)
C2—C1—C8—O1	−0.3 (2)	C17—C16—C21—C20	−1.8 (3)
S1—C1—C8—O1	179.93 (13)	S1—C16—C21—C20	−177.49 (14)
C2—C1—C8—C10	177.8 (2)	C19—C20—C21—C16	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2i	0.95	2.35	3.252 (3)	158
C9—H9B···Cg1ii	0.98	2.79	3.519 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.95	2.35	3.252 (3)	158
C9—H9B⋯Cg1ii	0.98	2.79	3.519 (2)	132

Symmetry codes: (i) ; (ii) .