Crystal structure of 5-chloro-2-(2-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10ClFO2S, the dihedral angle between the mean planes of the benzo-furan ring [r.m.s. deviation = 0.007 (1) Å] and the 2-fluoro-phenyl ring is 32.53 (5)°. In the crystal, mol-ecules related by inversion are paired into dimers via two different C-H⋯O hydrogen bonds. Further, Cl⋯O halogen bonds [3.114 (1) Å], and F⋯π [F-to-furan-centroid distance = 3.109 (1) Å] and S⋯F [3.1984 (9) Å] inter-actions link these into a three-dimensional network.

Related literature

For the pharmacological properties of benzo­furan compounds, see: Aslam et al. (2009 ▸); Galal et al. (2009 ▸); Howlett et al. (1999 ▸); Wahab Khan et al. (2005 ▸); Ono et al. (2002 ▸). For a related structure, see: Choi & Lee (2014 ▸). For further synthetic details, see: Choi et al. (1999 ▸). For a review of halogen bonding, see: Politzer et al. (2007 ▸).

Experimental

Crystal data

C15H10ClFO2S

M = 308.74

Triclinic,

a = 7.9626 (1) Å

b = 8.3518 (1) Å

c = 10.7127 (2) Å

α = 92.758 (1)°

β = 95.509 (1)°

γ = 112.373 (1)°

V = 652.97 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 173 K

0.45 × 0.36 × 0.32 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.690, T max = 0.746

12250 measured reflections

3263 independent reflections

3030 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.05

3263 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.26 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: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 1998 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015013948/fy2120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013948/fy2120Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013948/fy2120Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013948/fy2120fig1.tif

The mol­ecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.

x y z x y z x y z x y z x y z . DOI: 10.1107/S2056989015013948/fy2120fig2.tif

A view of the C–H⋯O, Cl⋯O, F⋯π and S⋯F inter­actions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 2, − y + 1, − z; (ii) − x + 1, − y + 1, − z; (iii) − x + 1, − y + 1, − z + 1; (iv) − x, − y, − z; (v) − x + 1, − y, − z.]

CCDC reference: 1414408

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

C15H10ClFO2S	Z = 2
Mr = 308.74	F(000) = 316
Triclinic, P1	Dx = 1.570 Mg m−3
a = 7.9626 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3518 (1) Å	Cell parameters from 6796 reflections
c = 10.7127 (2) Å	θ = 2.7–28.4°
α = 92.758 (1)°	µ = 0.46 mm−1
β = 95.509 (1)°	T = 173 K
γ = 112.373 (1)°	Block, colourless
V = 652.97 (2) Å3	0.45 × 0.36 × 0.32 mm

Bruker SMART APEXII CCD diffractometer	3263 independent reflections
Radiation source: rotating anode	3030 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm-1	Rint = 0.023
φ and ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.690, Tmax = 0.746	k = −11→11
12250 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2911P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3263 reflections	Δρmax = 0.34 e Å−3
183 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (3)

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.21 (d, J = 2.04 Hz, 1H), 7.66-7.71 (m, 1H), 7.50-7.57 (m, 2H), 7.32-7.41 (m, 2H), 7.21-7.26 (m, 1H), 3.15 (s, 3H).

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.

	x	y	z	Uiso*/Ueq
Cl1	0.80773 (5)	0.60679 (5)	0.52105 (3)	0.03134 (11)
S1	0.20658 (4)	0.19225 (4)	0.10339 (3)	0.02090 (10)
F1	0.22939 (12)	−0.06448 (11)	−0.07604 (8)	0.0324 (2)
O1	0.70194 (12)	0.36314 (12)	−0.00857 (8)	0.02229 (19)
O2	0.18502 (13)	0.32691 (13)	0.18956 (10)	0.0283 (2)
C1	0.44206 (16)	0.27158 (16)	0.08330 (11)	0.0198 (2)
C2	0.58981 (17)	0.37914 (16)	0.17693 (11)	0.0198 (2)
C3	0.60633 (18)	0.43369 (17)	0.30452 (12)	0.0220 (3)
H3	0.5032	0.4009	0.3498	0.026*
C4	0.77958 (18)	0.53749 (17)	0.36158 (12)	0.0231 (3)
C5	0.93409 (18)	0.58960 (18)	0.29751 (13)	0.0258 (3)
H5	1.0502	0.6620	0.3411	0.031*
C6	0.91896 (18)	0.53654 (18)	0.17133 (13)	0.0255 (3)
H6	1.0220	0.5701	0.1260	0.031*
C7	0.74560 (17)	0.43207 (16)	0.11491 (12)	0.0208 (2)
C8	0.51654 (17)	0.26585 (16)	−0.02553 (12)	0.0201 (2)
C9	0.44641 (17)	0.17903 (16)	−0.15243 (12)	0.0210 (2)
C10	0.30426 (18)	0.01690 (17)	−0.17542 (13)	0.0242 (3)
C11	0.2375 (2)	−0.06907 (19)	−0.29337 (14)	0.0304 (3)
H11	0.1390	−0.1796	−0.3049	0.036*
C12	0.3186 (2)	0.0106 (2)	−0.39495 (14)	0.0341 (3)
H12	0.2744	−0.0450	−0.4778	0.041*
C13	0.4640 (2)	0.1712 (2)	−0.37641 (13)	0.0311 (3)
H13	0.5198	0.2238	−0.4466	0.037*
C14	0.52834 (19)	0.25528 (17)	−0.25675 (12)	0.0244 (3)
H14	0.6282	0.3649	−0.2451	0.029*
C15	0.2029 (2)	0.02115 (19)	0.20017 (15)	0.0323 (3)
H15A	0.2950	0.0697	0.2741	0.048*
H15B	0.2302	−0.0665	0.1516	0.048*
H15C	0.0814	−0.0330	0.2276	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.02955 (19)	0.0403 (2)	0.02092 (16)	0.01176 (15)	−0.00124 (12)	−0.00425 (13)
S1	0.01618 (16)	0.02104 (16)	0.02386 (16)	0.00518 (12)	0.00408 (11)	0.00099 (11)
F1	0.0333 (5)	0.0245 (4)	0.0318 (4)	0.0018 (3)	0.0101 (4)	0.0004 (3)
O1	0.0179 (4)	0.0253 (4)	0.0208 (4)	0.0049 (4)	0.0045 (3)	0.0002 (3)
O2	0.0243 (5)	0.0265 (5)	0.0342 (5)	0.0092 (4)	0.0093 (4)	−0.0024 (4)
C1	0.0168 (6)	0.0198 (6)	0.0214 (6)	0.0054 (4)	0.0033 (4)	0.0016 (4)
C2	0.0176 (6)	0.0194 (6)	0.0223 (6)	0.0068 (4)	0.0031 (4)	0.0021 (4)
C3	0.0211 (6)	0.0247 (6)	0.0212 (6)	0.0095 (5)	0.0042 (5)	0.0024 (5)
C4	0.0245 (6)	0.0250 (6)	0.0199 (6)	0.0102 (5)	0.0007 (5)	0.0000 (5)
C5	0.0191 (6)	0.0268 (6)	0.0270 (6)	0.0054 (5)	−0.0012 (5)	−0.0009 (5)
C6	0.0185 (6)	0.0280 (7)	0.0274 (6)	0.0056 (5)	0.0054 (5)	0.0017 (5)
C7	0.0200 (6)	0.0216 (6)	0.0201 (5)	0.0069 (5)	0.0041 (4)	0.0014 (4)
C8	0.0174 (6)	0.0188 (5)	0.0232 (6)	0.0057 (4)	0.0032 (4)	0.0022 (4)
C9	0.0213 (6)	0.0221 (6)	0.0213 (6)	0.0104 (5)	0.0028 (5)	−0.0004 (4)
C10	0.0230 (6)	0.0235 (6)	0.0265 (6)	0.0092 (5)	0.0051 (5)	0.0009 (5)
C11	0.0286 (7)	0.0263 (7)	0.0319 (7)	0.0083 (6)	−0.0015 (6)	−0.0066 (5)
C12	0.0409 (9)	0.0368 (8)	0.0247 (7)	0.0177 (7)	−0.0020 (6)	−0.0067 (6)
C13	0.0395 (8)	0.0347 (7)	0.0221 (6)	0.0176 (6)	0.0047 (6)	0.0025 (5)
C14	0.0259 (6)	0.0244 (6)	0.0240 (6)	0.0106 (5)	0.0048 (5)	0.0027 (5)
C15	0.0310 (7)	0.0285 (7)	0.0386 (8)	0.0097 (6)	0.0134 (6)	0.0126 (6)

Cl1—C4	1.7425 (13)	C6—C7	1.3800 (18)
S1—O2	1.4913 (10)	C6—H6	0.9500
S1—C1	1.7739 (12)	C8—C9	1.4618 (17)
S1—C15	1.7983 (14)	C9—C10	1.3867 (18)
F1—C10	1.3542 (15)	C9—C14	1.4043 (18)
O1—C7	1.3741 (15)	C10—C11	1.3740 (19)
O1—C8	1.3762 (15)	C11—C12	1.386 (2)
C1—C8	1.3647 (17)	C11—H11	0.9500
C1—C2	1.4420 (17)	C12—C13	1.388 (2)
C2—C7	1.3945 (17)	C12—H12	0.9500
C2—C3	1.3976 (17)	C13—C14	1.3830 (19)
C3—C4	1.3802 (18)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.3990 (19)	C15—H15A	0.9800
C5—C6	1.3815 (19)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
O2—S1—C1	105.84 (6)	C1—C8—C9	135.10 (12)
O2—S1—C15	105.10 (7)	O1—C8—C9	114.01 (10)
C1—S1—C15	97.80 (6)	C10—C9—C14	117.07 (12)
C7—O1—C8	106.59 (9)	C10—C9—C8	122.54 (12)
C8—C1—C2	106.80 (11)	C14—C9—C8	120.32 (12)
C8—C1—S1	127.53 (10)	F1—C10—C11	117.65 (12)
C2—C1—S1	125.04 (9)	F1—C10—C9	118.49 (12)
C7—C2—C3	119.16 (11)	C11—C10—C9	123.83 (13)
C7—C2—C1	105.31 (11)	C10—C11—C12	117.90 (14)
C3—C2—C1	135.52 (12)	C10—C11—H11	121.1
C4—C3—C2	116.81 (12)	C12—C11—H11	121.0
C4—C3—H3	121.6	C11—C12—C13	120.39 (13)
C2—C3—H3	121.6	C11—C12—H12	119.8
C3—C4—C5	123.12 (12)	C13—C12—H12	119.8
C3—C4—Cl1	118.55 (10)	C14—C13—C12	120.60 (13)
C5—C4—Cl1	118.33 (10)	C14—C13—H13	119.7
C6—C5—C4	120.45 (12)	C12—C13—H13	119.7
C6—C5—H5	119.8	C13—C14—C9	120.18 (13)
C4—C5—H5	119.8	C13—C14—H14	119.9
C7—C6—C5	116.19 (12)	C9—C14—H14	119.9
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 (11)	H15A—C15—H15B	109.5
O1—C7—C2	110.42 (11)	S1—C15—H15C	109.5
C6—C7—C2	124.26 (12)	H15A—C15—H15C	109.5
C1—C8—O1	110.87 (11)	H15B—C15—H15C	109.5
O2—S1—C1—C8	−138.17 (12)	C1—C2—C7—C6	−179.34 (12)
C15—S1—C1—C8	113.63 (13)	C2—C1—C8—O1	−0.33 (14)
O2—S1—C1—C2	31.48 (12)	S1—C1—C8—O1	170.83 (9)
C15—S1—C1—C2	−76.71 (12)	C2—C1—C8—C9	178.19 (13)
C8—C1—C2—C7	0.43 (14)	S1—C1—C8—C9	−10.6 (2)
S1—C1—C2—C7	−171.01 (9)	C7—O1—C8—C1	0.10 (14)
C8—C1—C2—C3	−178.84 (14)	C7—O1—C8—C9	−178.76 (10)
S1—C1—C2—C3	9.7 (2)	C1—C8—C9—C10	−33.0 (2)
C7—C2—C3—C4	−0.38 (18)	O1—C8—C9—C10	145.51 (12)
C1—C2—C3—C4	178.82 (13)	C1—C8—C9—C14	150.06 (15)
C2—C3—C4—C5	0.61 (19)	O1—C8—C9—C14	−31.45 (17)
C2—C3—C4—Cl1	−179.26 (9)	C14—C9—C10—F1	176.27 (11)
C3—C4—C5—C6	−0.5 (2)	C8—C9—C10—F1	−0.78 (19)
Cl1—C4—C5—C6	179.35 (11)	C14—C9—C10—C11	−1.8 (2)
C4—C5—C6—C7	0.2 (2)	C8—C9—C10—C11	−178.88 (13)
C8—O1—C7—C6	179.14 (12)	F1—C10—C11—C12	−177.47 (13)
C8—O1—C7—C2	0.19 (14)	C9—C10—C11—C12	0.6 (2)
C5—C6—C7—O1	−178.76 (12)	C10—C11—C12—C13	0.8 (2)
C5—C6—C7—C2	0.0 (2)	C11—C12—C13—C14	−1.0 (2)
C3—C2—C7—O1	179.03 (11)	C12—C13—C14—C9	−0.2 (2)
C1—C2—C7—O1	−0.39 (14)	C10—C9—C14—C13	1.59 (19)
C3—C2—C7—C6	0.1 (2)	C8—C9—C14—C13	178.71 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.53	3.4756 (16)	176
C14—H14···O2ii	0.95	2.44	3.3591 (17)	163

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O1i	0.95	2.53	3.4756(16)	176
C14H14O2ii	0.95	2.44	3.3591(17)	163

Symmetry codes: (i) ; (ii) .