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

In the title compound, C15H10F2O2S, the dihedral angle between the plane of the benzo-furan ring system (r.m.s. deviation = 0.015 Å) and that of the 2-fluoro-phenyl ring is 28.53 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, and by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.625 (2) Å], forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C15H10F2O2S

M = 292.29

Monoclinic,

a = 8.6184 (2) Å

b = 16.8358 (4) Å

c = 9.4019 (2) Å

β = 111.254 (1)°

V = 1271.40 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.55 × 0.27 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.863, T max = 0.937

12086 measured reflections

3118 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.07

3118 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.40 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/S1600536814014810/bt6985sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014810/bt6985Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014810/bt6985Isup3.cml

CCDC reference: 1009826

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

C15H10F2O2S	F(000) = 600
Mr = 292.29	Dx = 1.527 Mg m−3
Monoclinic, P21/c	Melting point = 413–412 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6184 (2) Å	Cell parameters from 4357 reflections
b = 16.8358 (4) Å	θ = 2.4–27.8°
c = 9.4019 (2) Å	µ = 0.28 mm−1
β = 111.254 (1)°	T = 173 K
V = 1271.40 (5) Å3	Block, colourless
Z = 4	0.55 × 0.27 × 0.24 mm

Bruker SMART APEXII CCD diffractometer	3118 independent reflections
Radiation source: rotating anode	2650 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.4°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→19
Tmin = 0.863, Tmax = 0.937	l = −12→12
12086 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.100	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.3389P] where P = (Fo2 + 2Fc2)/3
3118 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.40 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	0.71915 (5)	0.69054 (2)	0.61445 (4)	0.02927 (12)
F1	1.13845 (13)	0.42819 (7)	0.91201 (11)	0.0485 (3)
F2	0.38183 (11)	0.67630 (6)	0.41827 (10)	0.0374 (2)
O1	0.67546 (12)	0.49850 (6)	0.36067 (11)	0.0281 (2)
O2	0.89953 (15)	0.70691 (7)	0.69905 (14)	0.0431 (3)
C1	0.71116 (17)	0.59444 (8)	0.53646 (16)	0.0234 (3)
C2	0.82307 (17)	0.53035 (9)	0.60821 (17)	0.0250 (3)
C3	0.94153 (18)	0.51622 (10)	0.75344 (17)	0.0299 (3)
H3	0.9632	0.5534	0.8344	0.036*
C4	1.02416 (19)	0.44539 (10)	0.77150 (18)	0.0336 (4)
C5	1.0016 (2)	0.38969 (10)	0.6577 (2)	0.0361 (4)
H5	1.0650	0.3421	0.6785	0.043*
C6	0.8859 (2)	0.40384 (9)	0.5134 (2)	0.0330 (3)
H6	0.8681	0.3673	0.4320	0.040*
C7	0.79767 (17)	0.47404 (9)	0.49421 (17)	0.0267 (3)
C8	0.62565 (17)	0.57246 (9)	0.38947 (16)	0.0242 (3)
C9	0.49420 (17)	0.60820 (9)	0.25958 (16)	0.0254 (3)
C10	0.37363 (18)	0.65773 (9)	0.27581 (17)	0.0271 (3)
C11	0.24304 (19)	0.68798 (10)	0.15475 (19)	0.0324 (3)
H11	0.1626	0.7215	0.1713	0.039*
C12	0.2317 (2)	0.66846 (11)	0.00904 (19)	0.0382 (4)
H12	0.1426	0.6886	−0.0764	0.046*
C13	0.3500 (2)	0.61954 (12)	−0.01285 (19)	0.0417 (4)
H13	0.3418	0.6064	−0.1136	0.050*
C14	0.4797 (2)	0.58969 (11)	0.10995 (18)	0.0351 (4)
H14	0.5601	0.5562	0.0930	0.042*
C15	0.6325 (2)	0.66632 (12)	0.7563 (2)	0.0435 (4)
H15A	0.6984	0.6239	0.8221	0.065*
H15B	0.5173	0.6484	0.7060	0.065*
H15C	0.6347	0.7135	0.8181	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0313 (2)	0.0205 (2)	0.0279 (2)	0.00149 (14)	0.00106 (15)	−0.00264 (14)
F1	0.0421 (6)	0.0544 (7)	0.0399 (6)	0.0162 (5)	0.0039 (5)	0.0204 (5)
F2	0.0311 (5)	0.0469 (6)	0.0322 (5)	0.0074 (4)	0.0092 (4)	−0.0046 (4)
O1	0.0285 (5)	0.0232 (5)	0.0278 (5)	0.0023 (4)	0.0045 (4)	−0.0042 (4)
O2	0.0356 (6)	0.0315 (7)	0.0463 (7)	−0.0063 (5)	−0.0041 (5)	−0.0079 (5)
C1	0.0240 (7)	0.0200 (7)	0.0239 (7)	−0.0001 (5)	0.0060 (5)	0.0002 (5)
C2	0.0239 (7)	0.0225 (7)	0.0278 (7)	0.0003 (5)	0.0085 (6)	0.0026 (6)
C3	0.0289 (7)	0.0308 (8)	0.0271 (8)	0.0014 (6)	0.0068 (6)	0.0047 (6)
C4	0.0273 (7)	0.0373 (9)	0.0332 (8)	0.0043 (6)	0.0073 (6)	0.0148 (7)
C5	0.0333 (8)	0.0262 (8)	0.0509 (10)	0.0080 (6)	0.0177 (7)	0.0123 (7)
C6	0.0354 (8)	0.0223 (8)	0.0426 (9)	0.0026 (6)	0.0155 (7)	0.0013 (7)
C7	0.0256 (7)	0.0234 (7)	0.0293 (8)	0.0004 (6)	0.0079 (6)	0.0026 (6)
C8	0.0233 (7)	0.0207 (7)	0.0269 (7)	−0.0001 (5)	0.0071 (6)	−0.0013 (6)
C9	0.0229 (7)	0.0235 (7)	0.0251 (7)	−0.0021 (5)	0.0029 (5)	−0.0002 (6)
C10	0.0250 (7)	0.0253 (7)	0.0277 (7)	−0.0033 (6)	0.0056 (6)	−0.0001 (6)
C11	0.0247 (7)	0.0280 (8)	0.0398 (9)	0.0000 (6)	0.0059 (6)	0.0058 (7)
C12	0.0305 (8)	0.0389 (10)	0.0333 (9)	−0.0031 (7)	−0.0027 (7)	0.0103 (7)
C13	0.0409 (9)	0.0522 (11)	0.0237 (8)	−0.0017 (8)	0.0020 (7)	0.0002 (7)
C14	0.0332 (8)	0.0390 (10)	0.0286 (8)	0.0031 (7)	0.0059 (6)	−0.0041 (7)
C15	0.0510 (11)	0.0494 (11)	0.0300 (9)	0.0126 (9)	0.0143 (8)	−0.0051 (8)

S1—O2	1.4930 (12)	C6—C7	1.381 (2)
S1—C1	1.7675 (14)	C6—H6	0.9500
S1—C15	1.7952 (18)	C8—C9	1.461 (2)
F1—C4	1.3623 (18)	C9—C10	1.383 (2)
F2—C10	1.3521 (17)	C9—C14	1.402 (2)
O1—C8	1.3757 (17)	C10—C11	1.376 (2)
O1—C7	1.3772 (18)	C11—C12	1.377 (2)
C1—C8	1.3606 (19)	C11—H11	0.9500
C1—C2	1.441 (2)	C12—C13	1.383 (3)
C2—C7	1.388 (2)	C12—H12	0.9500
C2—C3	1.397 (2)	C13—C14	1.378 (2)
C3—C4	1.368 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.383 (3)	C15—H15A	0.9800
C5—C6	1.382 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
O2—S1—C1	105.45 (7)	C1—C8—C9	135.03 (14)
O2—S1—C15	106.22 (8)	O1—C8—C9	114.27 (12)
C1—S1—C15	97.82 (8)	C10—C9—C14	116.59 (14)
C8—O1—C7	106.33 (11)	C10—C9—C8	122.83 (13)
C8—C1—C2	107.22 (13)	C14—C9—C8	120.49 (14)
C8—C1—S1	126.55 (11)	F2—C10—C11	117.86 (14)
C2—C1—S1	124.91 (11)	F2—C10—C9	118.49 (13)
C7—C2—C3	119.55 (14)	C11—C10—C9	123.63 (14)
C7—C2—C1	104.98 (13)	C10—C11—C12	118.45 (15)
C3—C2—C1	135.45 (14)	C10—C11—H11	120.8
C4—C3—C2	115.65 (15)	C12—C11—H11	120.8
C4—C3—H3	122.2	C11—C12—C13	119.99 (15)
C2—C3—H3	122.2	C11—C12—H12	120.0
F1—C4—C3	117.82 (15)	C13—C12—H12	120.0
F1—C4—C5	117.12 (14)	C14—C13—C12	120.69 (16)
C3—C4—C5	125.06 (15)	C14—C13—H13	119.7
C6—C5—C4	119.46 (15)	C12—C13—H13	119.7
C6—C5—H5	120.3	C13—C14—C9	120.65 (16)
C4—C5—H5	120.3	C13—C14—H14	119.7
C7—C6—C5	116.30 (15)	C9—C14—H14	119.7
C7—C6—H6	121.9	S1—C15—H15A	109.5
C5—C6—H6	121.9	S1—C15—H15B	109.5
O1—C7—C6	125.31 (14)	H15A—C15—H15B	109.5
O1—C7—C2	110.75 (12)	S1—C15—H15C	109.5
C6—C7—C2	123.93 (14)	H15A—C15—H15C	109.5
C1—C8—O1	110.69 (12)	H15B—C15—H15C	109.5
O2—S1—C1—C8	−131.06 (13)	C1—C2—C7—C6	177.33 (14)
C15—S1—C1—C8	119.65 (14)	C2—C1—C8—O1	−0.41 (16)
O2—S1—C1—C2	34.10 (14)	S1—C1—C8—O1	166.89 (10)
C15—S1—C1—C2	−75.19 (14)	C2—C1—C8—C9	178.28 (15)
C8—C1—C2—C7	1.30 (15)	S1—C1—C8—C9	−14.4 (2)
S1—C1—C2—C7	−166.26 (11)	C7—O1—C8—C1	−0.67 (15)
C8—C1—C2—C3	179.85 (16)	C7—O1—C8—C9	−179.65 (12)
S1—C1—C2—C3	12.3 (2)	C1—C8—C9—C10	−31.3 (3)
C7—C2—C3—C4	−0.5 (2)	O1—C8—C9—C10	147.36 (14)
C1—C2—C3—C4	−178.85 (16)	C1—C8—C9—C14	152.31 (17)
C2—C3—C4—F1	−178.67 (13)	O1—C8—C9—C14	−29.0 (2)
C2—C3—C4—C5	1.7 (2)	C14—C9—C10—F2	179.21 (13)
F1—C4—C5—C6	179.35 (14)	C8—C9—C10—F2	2.7 (2)
C3—C4—C5—C6	−1.0 (3)	C14—C9—C10—C11	0.7 (2)
C4—C5—C6—C7	−0.9 (2)	C8—C9—C10—C11	−175.83 (14)
C8—O1—C7—C6	−177.54 (14)	F2—C10—C11—C12	−178.95 (14)
C8—O1—C7—C2	1.55 (16)	C9—C10—C11—C12	−0.4 (2)
C5—C6—C7—O1	−178.87 (14)	C10—C11—C12—C13	0.0 (3)
C5—C6—C7—C2	2.2 (2)	C11—C12—C13—C14	0.2 (3)
C3—C2—C7—O1	179.41 (12)	C12—C13—C14—C9	0.1 (3)
C1—C2—C7—O1	−1.76 (16)	C10—C9—C14—C13	−0.5 (2)
C3—C2—C7—C6	−1.5 (2)	C8—C9—C14—C13	176.09 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.52	3.343 (2)	145
C12—H12···O2ii	0.95	2.39	3.326 (2)	166
C15—H15A···F1iii	0.98	2.54	3.419 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.52	3.343 (2)	145
C12—H12⋯O2ii	0.95	2.39	3.326 (2)	166
C15—H15A⋯F1iii	0.98	2.54	3.419 (2)	149

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