5-Chloro-3-(4-fluoro-phenyl-sulfon-yl)-2,7-dimethyl-1-benzo-furan.

In the title compound, C16H12ClFO3S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.007 (1) Å] and that of the 4-fluoro-phenyl ring is 76.11 (5)°. In the crystal, mol-ecules are linked into [010] chains via two different inversion-generated pairs of C-H⋯O hydrogen bonds. The crystal structure also exhibits weak π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.820 (2) Å].

Related literature

For the pharmaceutical properties of compounds containing benzo­furan moieties, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Howlett et al. (1999 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzo­furan ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material 5-chloro-3-(4-fluoro­phenyl­sulfan­yl)-2,7-dimethyl-1-benzo­furan, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2014 ▶).

Experimental

Crystal data

C16H12ClFO3S

M = 338.77

Triclinic,

a = 8.4338 (3) Å

b = 9.9171 (3) Å

c = 10.1059 (3) Å

α = 73.988 (2)°

β = 66.155 (2)°

γ = 73.629 (2)°

V = 729.02 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 173 K

0.47 × 0.31 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.825, T max = 0.939

13460 measured reflections

3614 independent reflections

3163 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.03

3614 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.37 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/S1600536814019114/mw2126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019114/mw2126Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019114/mw2126Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019114/mw2126fig1.tif

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

Click here for additional data file.

x y z x y z . DOI: 10.1107/S1600536814019114/mw2126fig2.tif

A view of the C—H⋯O and π–π inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x, − y + 1, − z + 1; (ii) − x, − y + 2, − z.]

CCDC reference: 1020842

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

C16H12ClFO3S	Z = 2
Mr = 338.77	F(000) = 348
Triclinic, P1	Dx = 1.543 Mg m−3
Hall symbol: -P 1	Melting point = 469–468 K
a = 8.4338 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9171 (3) Å	Cell parameters from 5949 reflections
c = 10.1059 (3) Å	θ = 2.2–28.3°
α = 73.988 (2)°	µ = 0.43 mm−1
β = 66.155 (2)°	T = 173 K
γ = 73.629 (2)°	Block, colourless
V = 729.02 (4) Å3	0.47 × 0.31 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	3614 independent reflections
Radiation source: rotating anode	3163 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.825, Tmax = 0.939	l = −13→13
13460 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.4675P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3614 reflections	Δρmax = 0.34 e Å−3
202 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.98-8.03 (m, 2H), 7.67 (d, J = 2.04 Hz, 1H), 7.17-7.22 (m, 2H), 7.10 (s, 1H), 2.80 (s, 3H), 2.43 (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.

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
Cl1	0.51698 (6)	0.19310 (5)	0.47396 (5)	0.03701 (14)
S1	0.13342 (5)	0.69006 (4)	0.14183 (4)	0.02143 (12)
F1	0.70966 (17)	0.98587 (15)	−0.25209 (14)	0.0518 (4)
O1	0.04838 (15)	0.74576 (13)	0.53640 (13)	0.0263 (3)
O2	0.18910 (16)	0.54497 (12)	0.11860 (13)	0.0272 (3)
O3	−0.02442 (16)	0.77606 (13)	0.11823 (13)	0.0291 (3)
C1	0.1165 (2)	0.68330 (17)	0.32016 (17)	0.0215 (3)
C2	0.2069 (2)	0.56854 (17)	0.40420 (17)	0.0217 (3)
C3	0.3177 (2)	0.43625 (17)	0.38227 (18)	0.0235 (3)
H3	0.3506	0.4013	0.2943	0.028*
C4	0.3767 (2)	0.35884 (18)	0.49555 (19)	0.0260 (3)
C5	0.3304 (2)	0.40691 (19)	0.62598 (19)	0.0285 (4)
H5	0.3761	0.3492	0.6996	0.034*
C6	0.2188 (2)	0.53740 (19)	0.65043 (18)	0.0267 (4)
C7	0.1604 (2)	0.61368 (18)	0.53606 (18)	0.0236 (3)
C8	0.0241 (2)	0.78571 (18)	0.40404 (18)	0.0240 (3)
C9	0.1674 (3)	0.5919 (2)	0.78961 (19)	0.0361 (4)
H9A	0.1210	0.6950	0.7737	0.054*
H9B	0.2713	0.5730	0.8175	0.054*
H9C	0.0764	0.5431	0.8685	0.054*
C10	−0.0915 (2)	0.92612 (19)	0.3815 (2)	0.0322 (4)
H10A	−0.0361	1.0018	0.3790	0.048*
H10B	−0.2059	0.9286	0.4625	0.048*
H10C	−0.1092	0.9411	0.2881	0.048*
C11	0.3084 (2)	0.78021 (17)	0.02639 (17)	0.0224 (3)
C12	0.4815 (2)	0.70757 (19)	0.0003 (2)	0.0306 (4)
H12	0.5062	0.6108	0.0468	0.037*
C13	0.6181 (3)	0.7776 (2)	−0.0943 (2)	0.0374 (4)
H13	0.7379	0.7301	−0.1138	0.045*
C14	0.5764 (3)	0.9174 (2)	−0.1594 (2)	0.0339 (4)
C15	0.4069 (3)	0.9914 (2)	−0.1352 (2)	0.0348 (4)
H15	0.3834	1.0880	−0.1825	0.042*
C16	0.2703 (2)	0.92165 (19)	−0.03976 (19)	0.0299 (4)
H16	0.1511	0.9706	−0.0198	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0373 (3)	0.0245 (2)	0.0429 (3)	−0.00018 (18)	−0.0175 (2)	0.00258 (18)
S1	0.0238 (2)	0.0211 (2)	0.01966 (19)	−0.00243 (15)	−0.00994 (15)	−0.00263 (14)
F1	0.0438 (7)	0.0607 (9)	0.0443 (7)	−0.0292 (7)	0.0018 (5)	−0.0068 (6)
O1	0.0261 (6)	0.0302 (6)	0.0231 (6)	−0.0035 (5)	−0.0074 (5)	−0.0100 (5)
O2	0.0366 (7)	0.0233 (6)	0.0244 (6)	−0.0044 (5)	−0.0133 (5)	−0.0062 (5)
O3	0.0253 (6)	0.0319 (7)	0.0299 (6)	−0.0029 (5)	−0.0148 (5)	−0.0005 (5)
C1	0.0220 (7)	0.0222 (8)	0.0199 (7)	−0.0032 (6)	−0.0077 (6)	−0.0042 (6)
C2	0.0229 (7)	0.0233 (8)	0.0186 (7)	−0.0066 (6)	−0.0072 (6)	−0.0015 (6)
C3	0.0250 (8)	0.0225 (8)	0.0216 (8)	−0.0042 (6)	−0.0082 (6)	−0.0025 (6)
C4	0.0252 (8)	0.0218 (8)	0.0285 (8)	−0.0057 (6)	−0.0106 (6)	0.0022 (6)
C5	0.0307 (9)	0.0319 (9)	0.0234 (8)	−0.0122 (7)	−0.0135 (7)	0.0063 (7)
C6	0.0280 (8)	0.0350 (9)	0.0190 (7)	−0.0138 (7)	−0.0076 (6)	−0.0010 (6)
C7	0.0221 (8)	0.0264 (8)	0.0217 (8)	−0.0063 (6)	−0.0053 (6)	−0.0056 (6)
C8	0.0224 (8)	0.0262 (8)	0.0245 (8)	−0.0045 (6)	−0.0086 (6)	−0.0062 (6)
C9	0.0388 (10)	0.0529 (12)	0.0211 (8)	−0.0162 (9)	−0.0100 (7)	−0.0075 (8)
C10	0.0290 (9)	0.0281 (9)	0.0395 (10)	0.0031 (7)	−0.0131 (8)	−0.0134 (8)
C11	0.0243 (8)	0.0240 (8)	0.0188 (7)	−0.0036 (6)	−0.0079 (6)	−0.0042 (6)
C12	0.0262 (9)	0.0245 (9)	0.0385 (10)	0.0002 (7)	−0.0105 (7)	−0.0084 (7)
C13	0.0257 (9)	0.0379 (11)	0.0455 (11)	−0.0041 (8)	−0.0049 (8)	−0.0168 (9)
C14	0.0347 (10)	0.0410 (11)	0.0260 (9)	−0.0166 (8)	−0.0031 (7)	−0.0084 (8)
C15	0.0421 (11)	0.0321 (10)	0.0291 (9)	−0.0124 (8)	−0.0145 (8)	0.0045 (7)
C16	0.0299 (9)	0.0277 (9)	0.0290 (9)	−0.0034 (7)	−0.0131 (7)	0.0012 (7)

Cl1—C4	1.7440 (18)	C6—C9	1.501 (2)
S1—O3	1.4356 (12)	C8—C10	1.477 (2)
S1—O2	1.4361 (12)	C9—H9A	0.9800
S1—C1	1.7332 (16)	C9—H9B	0.9800
S1—C11	1.7648 (16)	C9—H9C	0.9800
F1—C14	1.353 (2)	C10—H10A	0.9800
O1—C8	1.368 (2)	C10—H10B	0.9800
O1—C7	1.382 (2)	C10—H10C	0.9800
C1—C8	1.361 (2)	C11—C16	1.386 (2)
C1—C2	1.448 (2)	C11—C12	1.386 (2)
C2—C7	1.392 (2)	C12—C13	1.385 (3)
C2—C3	1.395 (2)	C12—H12	0.9500
C3—C4	1.382 (2)	C13—C14	1.374 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.394 (3)	C14—C15	1.366 (3)
C5—C6	1.387 (3)	C15—C16	1.385 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.385 (2)	C16—H16	0.9500
O3—S1—O2	119.75 (8)	C6—C9—H9A	109.5
O3—S1—C1	109.59 (8)	C6—C9—H9B	109.5
O2—S1—C1	106.33 (7)	H9A—C9—H9B	109.5
O3—S1—C11	107.27 (8)	C6—C9—H9C	109.5
O2—S1—C11	107.36 (8)	H9A—C9—H9C	109.5
C1—S1—C11	105.71 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.05 (12)	C8—C10—H10A	109.5
C8—C1—C2	107.60 (14)	C8—C10—H10B	109.5
C8—C1—S1	126.93 (13)	H10A—C10—H10B	109.5
C2—C1—S1	125.40 (12)	C8—C10—H10C	109.5
C7—C2—C3	119.54 (15)	H10A—C10—H10C	109.5
C7—C2—C1	104.59 (14)	H10B—C10—H10C	109.5
C3—C2—C1	135.87 (15)	C16—C11—C12	121.04 (16)
C4—C3—C2	116.27 (15)	C16—C11—S1	119.36 (13)
C4—C3—H3	121.9	C12—C11—S1	119.58 (13)
C2—C3—H3	121.9	C13—C12—C11	119.27 (17)
C3—C4—C5	123.25 (16)	C13—C12—H12	120.4
C3—C4—Cl1	118.38 (14)	C11—C12—H12	120.4
C5—C4—Cl1	118.37 (13)	C14—C13—C12	118.39 (18)
C6—C5—C4	121.29 (16)	C14—C13—H13	120.8
C6—C5—H5	119.4	C12—C13—H13	120.8
C4—C5—H5	119.4	F1—C14—C15	118.07 (18)
C7—C6—C5	114.81 (15)	F1—C14—C13	118.47 (18)
C7—C6—C9	122.84 (17)	C15—C14—C13	123.45 (17)
C5—C6—C9	122.34 (16)	C14—C15—C16	118.13 (18)
O1—C7—C6	124.81 (15)	C14—C15—H15	120.9
O1—C7—C2	110.37 (14)	C16—C15—H15	120.9
C6—C7—C2	124.83 (16)	C15—C16—C11	119.71 (17)
C1—C8—O1	110.39 (15)	C15—C16—H16	120.1
C1—C8—C10	133.98 (16)	C11—C16—H16	120.1
O1—C8—C10	115.63 (14)
O3—S1—C1—C8	−29.69 (17)	C1—C2—C7—O1	0.51 (17)
O2—S1—C1—C8	−160.47 (15)	C3—C2—C7—C6	1.2 (2)
C11—S1—C1—C8	85.62 (16)	C1—C2—C7—C6	−179.20 (15)
O3—S1—C1—C2	153.51 (13)	C2—C1—C8—O1	0.14 (18)
O2—S1—C1—C2	22.72 (16)	S1—C1—C8—O1	−177.13 (11)
C11—S1—C1—C2	−91.19 (15)	C2—C1—C8—C10	179.67 (18)
C8—C1—C2—C7	−0.40 (18)	S1—C1—C8—C10	2.4 (3)
S1—C1—C2—C7	176.93 (12)	C7—O1—C8—C1	0.18 (18)
C8—C1—C2—C3	179.10 (17)	C7—O1—C8—C10	−179.45 (14)
S1—C1—C2—C3	−3.6 (3)	O3—S1—C11—C16	13.38 (16)
C7—C2—C3—C4	−1.0 (2)	O2—S1—C11—C16	143.30 (14)
C1—C2—C3—C4	179.57 (17)	C1—S1—C11—C16	−103.50 (15)
C2—C3—C4—C5	0.2 (2)	O3—S1—C11—C12	−164.96 (14)
C2—C3—C4—Cl1	−179.55 (12)	O2—S1—C11—C12	−35.04 (16)
C3—C4—C5—C6	0.6 (3)	C1—S1—C11—C12	78.15 (15)
Cl1—C4—C5—C6	−179.72 (13)	C16—C11—C12—C13	−0.5 (3)
C4—C5—C6—C7	−0.4 (2)	S1—C11—C12—C13	177.85 (14)
C4—C5—C6—C9	−179.76 (16)	C11—C12—C13—C14	−0.2 (3)
C8—O1—C7—C6	179.28 (15)	C12—C13—C14—F1	−179.88 (17)
C8—O1—C7—C2	−0.44 (17)	C12—C13—C14—C15	0.4 (3)
C5—C6—C7—O1	179.86 (14)	F1—C14—C15—C16	−179.67 (17)
C9—C6—C7—O1	−0.8 (3)	C13—C14—C15—C16	0.1 (3)
C5—C6—C7—C2	−0.5 (2)	C14—C15—C16—C11	−0.7 (3)
C9—C6—C7—C2	178.89 (16)	C12—C11—C16—C15	0.9 (3)
C3—C2—C7—O1	−179.08 (13)	S1—C11—C16—C15	−177.40 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O2i	0.98	2.57	3.331 (2)	135
C16—H16···O3ii	0.95	2.53	3.230 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O2i	0.98	2.57	3.331 (2)	135
C16—H16⋯O3ii	0.95	2.53	3.230 (2)	130

Symmetry codes: (i) ; (ii) .