2-(4-Chloro­phen­yl)-5-fluoro-3-methyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536810001157

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o364

https://doi.org/10.1107/S1600536810001157

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2-(4-Chlorophenyl)-5-fluoro-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 4 January 2010; accepted 10 January 2010; online 16 January 2010)

In the title compound, C₁₅H₁₀ClFO₂S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-chlorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 21.04 (4)°. The crystal structure exhibits a weak intermolecular C—H⋯O hydrogen bond and a Cl⋯O halogen bond [Cl⋯O = 3.254 (1) Å].

Related literature

For the crystal structures of similar 5-fluoro-2-(4-halophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ,b ,c ). For the biological properties of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Howlett et al. (1999 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₀ClFO₂S
M_r = 308.74
Triclinic, $[P \overline 1]$
a = 7.7088 (5) Å
b = 8.5241 (5) Å
c = 11.6369 (7) Å
α = 74.572 (3)°
β = 70.893 (3)°
γ = 67.109 (3)°
V = 657.13 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 100 K
0.25 × 0.22 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.895, T_max = 0.942
10607 measured reflections
3020 independent reflections
2629 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.03
3020 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.52	3.347 (2)	148
Symmetry code: (i) -x, -y+1, -z+1.

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, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810001157/vm2017sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001157/vm2017Isup2.hkl

checkCIF report

Comment top

Benzofuran ring systems have drawn considerable interest in view of their biological properties (Aslam et al., 2006; Galal et al., 2009; Howlett et al. 1999) and their occurrence as natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 5-fluoro-2-(4-halophenyl)-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the plane of the benzofuran and the 4-chlorophenyl ring is 21.04 (4)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C–H···O hydrogen bond between the 4-chlorophenyl H atom and the oxygen of the S═O unit (Table 1). The molecular packing (Fig. 2) is further stabilized by a Cl···O halogen bond between the chlorine and the oxygen of the S═O unit [Cl···O2ⁱⁱ = 3.254 (1) Å; C–Cl···O2 = 163.42 (6)°] (Politzer et al., 2007).

Related literature top

For the crystal structures of similar 5-fluoro-2-(4-halophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b,c). For the biological properties of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Howlett et al. (1999). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2-(4-chlorophenyl)-5-fluoro-3-methylsulfanyl-1-benzofuran (351 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 81 %, m.p. 442-443 K; R_f = 0.41 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Structure description top

For the crystal structures of similar 5-fluoro-2-(4-halophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b,c). For the biological properties of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Howlett et al. (1999). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For a review of halogen bonding, see: Politzer et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. 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 a small spheres of arbitrary radius.
	Fig. 2. C–H···O and C–Cl···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x, - y + 1, - z + 1; (ii) x, y, z + 1; (iii) x, y, z - 1.]

2-(4-Chlorophenyl)-5-fluoro-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₅H₁₀ClFO₂S	Z = 2
M_r = 308.74	F(000) = 316
Triclinic, P1	D_x = 1.560 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7088 (5) Å	Cell parameters from 6597 reflections
b = 8.5241 (5) Å	θ = 2.6–27.6°
c = 11.6369 (7) Å	µ = 0.46 mm⁻¹
α = 74.572 (3)°	T = 100 K
β = 70.893 (3)°	Block, colourless
γ = 67.109 (3)°	0.25 × 0.22 × 0.13 mm
V = 657.13 (7) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3020 independent reflections
Radiation source: Rotating Anode	2629 reflections with I > 2σ(I)
HELIOS monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 1.9°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.895, T_max = 0.942	l = −15→15
10607 measured reflections

Refinement top

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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0428P)² + 0.2892P] where P = (F_o² + 2F_c²)/3
3020 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₀ClFO₂S	γ = 67.109 (3)°
M_r = 308.74	V = 657.13 (7) Å³
Triclinic, P1	Z = 2
a = 7.7088 (5) Å	Mo Kα radiation
b = 8.5241 (5) Å	µ = 0.46 mm⁻¹
c = 11.6369 (7) Å	T = 100 K
α = 74.572 (3)°	0.25 × 0.22 × 0.13 mm
β = 70.893 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3020 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2629 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.942	R_int = 0.032
10607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
3020 reflections	Δρ_min = −0.27 e Å⁻³
182 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl	0.33113 (7)	0.22955 (5)	1.02698 (4)	0.03627 (12)
S	0.35910 (5)	0.20350 (5)	0.40485 (3)	0.02555 (11)
F	0.16308 (18)	0.76845 (15)	0.01238 (10)	0.0474 (3)
O1	0.17250 (15)	0.67346 (13)	0.48816 (10)	0.0258 (2)
O2	0.25799 (18)	0.18174 (15)	0.32408 (12)	0.0356 (3)
C1	0.2811 (2)	0.42581 (18)	0.41217 (13)	0.0232 (3)
C2	0.2278 (2)	0.56740 (19)	0.31515 (14)	0.0243 (3)
C3	0.2310 (2)	0.5825 (2)	0.19235 (14)	0.0299 (3)
H3	0.2760	0.4867	0.1534	0.036*
C4	0.1632 (3)	0.7478 (2)	0.13242 (15)	0.0325 (4)
C5	0.0958 (3)	0.8951 (2)	0.18489 (16)	0.0339 (4)
H5	0.0520	1.0032	0.1387	0.041*
C6	0.0940 (2)	0.8808 (2)	0.30654 (15)	0.0302 (3)
H6	0.0506	0.9771	0.3446	0.036*
C7	0.1604 (2)	0.7151 (2)	0.36803 (13)	0.0248 (3)
C8	0.2452 (2)	0.49619 (18)	0.51340 (13)	0.0231 (3)
C9	0.2682 (2)	0.42787 (18)	0.63814 (13)	0.0225 (3)
C10	0.1603 (2)	0.52936 (19)	0.73078 (14)	0.0251 (3)
H10	0.0727	0.6383	0.7124	0.030*
C12	0.3088 (2)	0.3053 (2)	0.87660 (13)	0.0258 (3)
C11	0.1826 (2)	0.4693 (2)	0.84935 (14)	0.0277 (3)
H11	0.1134	0.5386	0.9102	0.033*
C13	0.4161 (2)	0.2011 (2)	0.78744 (14)	0.0277 (3)
H13	0.4990	0.0903	0.8073	0.033*
C14	0.3979 (2)	0.2645 (2)	0.66813 (14)	0.0269 (3)
H14	0.4734	0.1971	0.6067	0.032*
C15	0.6025 (2)	0.1816 (2)	0.31476 (18)	0.0396 (4)
H15A	0.6681	0.0656	0.2979	0.059*
H15B	0.6705	0.2072	0.3594	0.059*
H15C	0.5994	0.2603	0.2385	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0509 (3)	0.0319 (2)	0.0236 (2)	−0.00862 (18)	−0.01631 (17)	0.00016 (15)
S	0.0298 (2)	0.01997 (19)	0.0270 (2)	−0.00747 (15)	−0.00886 (15)	−0.00284 (14)
F	0.0699 (8)	0.0475 (7)	0.0278 (5)	−0.0194 (6)	−0.0255 (5)	0.0055 (4)
O1	0.0325 (6)	0.0201 (5)	0.0237 (5)	−0.0059 (4)	−0.0107 (4)	−0.0013 (4)
O2	0.0393 (6)	0.0307 (6)	0.0433 (7)	−0.0091 (5)	−0.0178 (5)	−0.0107 (5)
C1	0.0264 (7)	0.0195 (7)	0.0237 (7)	−0.0073 (6)	−0.0084 (5)	−0.0009 (5)
C2	0.0262 (7)	0.0227 (7)	0.0254 (7)	−0.0095 (6)	−0.0095 (6)	0.0003 (6)
C3	0.0373 (8)	0.0306 (8)	0.0252 (7)	−0.0135 (7)	−0.0111 (6)	−0.0025 (6)
C4	0.0391 (9)	0.0381 (9)	0.0227 (7)	−0.0154 (7)	−0.0151 (6)	0.0046 (6)
C5	0.0374 (9)	0.0282 (8)	0.0347 (9)	−0.0110 (7)	−0.0181 (7)	0.0087 (6)
C6	0.0335 (8)	0.0219 (7)	0.0340 (8)	−0.0065 (6)	−0.0135 (6)	−0.0006 (6)
C7	0.0267 (7)	0.0255 (7)	0.0234 (7)	−0.0093 (6)	−0.0100 (6)	−0.0003 (6)
C8	0.0230 (7)	0.0195 (7)	0.0256 (7)	−0.0058 (5)	−0.0080 (5)	−0.0013 (5)
C9	0.0245 (7)	0.0223 (7)	0.0224 (7)	−0.0092 (6)	−0.0081 (5)	−0.0013 (5)
C10	0.0261 (7)	0.0216 (7)	0.0258 (7)	−0.0060 (6)	−0.0079 (6)	−0.0019 (5)
C12	0.0301 (7)	0.0279 (8)	0.0211 (7)	−0.0114 (6)	−0.0099 (6)	0.0005 (6)
C11	0.0304 (8)	0.0274 (8)	0.0240 (7)	−0.0091 (6)	−0.0046 (6)	−0.0055 (6)
C13	0.0307 (8)	0.0229 (7)	0.0276 (8)	−0.0043 (6)	−0.0130 (6)	−0.0010 (6)
C14	0.0295 (8)	0.0248 (7)	0.0253 (7)	−0.0049 (6)	−0.0090 (6)	−0.0058 (6)
C15	0.0306 (8)	0.0324 (9)	0.0527 (11)	−0.0088 (7)	−0.0035 (8)	−0.0131 (8)

Geometric parameters (Å, º) top

Cl—O2ⁱ	3.254 (1)	C6—C7	1.382 (2)
Cl—C12	1.737 (2)	C6—H6	0.9300
S—O2	1.487 (1)	C8—C9	1.455 (2)
S—C1	1.768 (2)	C9—C14	1.396 (2)
S—C15	1.788 (2)	C9—C10	1.397 (2)
F—C4	1.361 (2)	C10—C11	1.381 (2)
O1—C7	1.373 (2)	C10—H10	0.9300
O1—C8	1.377 (2)	C12—C13	1.381 (2)
C1—C8	1.363 (2)	C12—C11	1.382 (2)
C1—C2	1.447 (2)	C11—H11	0.9300
C2—C7	1.388 (2)	C13—C14	1.381 (2)
C2—C3	1.393 (2)	C13—H13	0.9300
C3—C4	1.374 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.382 (3)	C15—H15B	0.9600
C5—C6	1.384 (2)	C15—H15C	0.9600
C5—H5	0.9300

C12—Cl—O2ⁱ	163.42 (6)	C1—C8—C9	134.98 (14)
O2—S—C1	107.93 (7)	O1—C8—C9	114.44 (12)
O2—S—C15	105.99 (8)	C14—C9—C10	118.63 (13)
C1—S—C15	97.60 (8)	C14—C9—C8	122.01 (13)
C7—O1—C8	106.67 (11)	C10—C9—C8	119.35 (13)
C8—C1—C2	106.99 (13)	C11—C10—C9	120.57 (14)
C8—C1—S	126.32 (11)	C11—C10—H10	119.7
C2—C1—S	126.50 (11)	C9—C10—H10	119.7
C7—C2—C3	119.55 (14)	C13—C12—C11	121.54 (14)
C7—C2—C1	105.05 (13)	C13—C12—Cl	119.65 (12)
C3—C2—C1	135.40 (14)	C11—C12—Cl	118.80 (12)
C4—C3—C2	115.73 (15)	C10—C11—C12	119.31 (14)
C4—C3—H3	122.1	C10—C11—H11	120.3
C2—C3—H3	122.1	C12—C11—H11	120.3
F—C4—C3	117.68 (15)	C12—C13—C14	118.74 (14)
F—C4—C5	117.49 (15)	C12—C13—H13	120.6
C3—C4—C5	124.84 (15)	C14—C13—H13	120.6
C4—C5—C6	119.63 (15)	C13—C14—C9	121.16 (14)
C4—C5—H5	120.2	C13—C14—H14	119.4
C6—C5—H5	120.2	C9—C14—H14	119.4
C7—C6—C5	116.06 (15)	S—C15—H15A	109.5
C7—C6—H6	122.0	S—C15—H15B	109.5
C5—C6—H6	122.0	H15A—C15—H15B	109.5
O1—C7—C6	125.09 (14)	S—C15—H15C	109.5
O1—C7—C2	110.71 (13)	H15A—C15—H15C	109.5
C6—C7—C2	124.19 (14)	H15B—C15—H15C	109.5
C1—C8—O1	110.57 (13)

O2—S—C1—C8	141.66 (14)	C1—C2—C7—C6	180.00 (14)
C15—S—C1—C8	−108.75 (15)	C2—C1—C8—O1	−0.06 (17)
O2—S—C1—C2	−32.73 (15)	S—C1—C8—O1	−175.34 (10)
C15—S—C1—C2	76.86 (15)	C2—C1—C8—C9	−179.09 (16)
C8—C1—C2—C7	−0.66 (16)	S—C1—C8—C9	5.6 (3)
S—C1—C2—C7	174.61 (11)	C7—O1—C8—C1	0.77 (16)
C8—C1—C2—C3	179.28 (17)	C7—O1—C8—C9	−179.99 (12)
S—C1—C2—C3	−5.5 (3)	C1—C8—C9—C14	22.0 (3)
C7—C2—C3—C4	−0.5 (2)	O1—C8—C9—C14	−156.97 (14)
C1—C2—C3—C4	179.56 (16)	C1—C8—C9—C10	−159.18 (17)
C2—C3—C4—F	−179.79 (14)	O1—C8—C9—C10	21.82 (19)
C2—C3—C4—C5	0.5 (3)	C14—C9—C10—C11	0.3 (2)
F—C4—C5—C6	−179.70 (15)	C8—C9—C10—C11	−178.49 (13)
C3—C4—C5—C6	0.0 (3)	C9—C10—C11—C12	−1.9 (2)
C4—C5—C6—C7	−0.5 (2)	C13—C12—C11—C10	1.3 (2)
C8—O1—C7—C6	179.96 (14)	Cl—C12—C11—C10	−178.53 (12)
C8—O1—C7—C2	−1.21 (16)	C11—C12—C13—C14	0.9 (2)
C5—C6—C7—O1	179.14 (14)	Cl—C12—C13—C14	−179.24 (12)
C5—C6—C7—C2	0.5 (2)	C12—C13—C14—C9	−2.6 (2)
C3—C2—C7—O1	−178.79 (13)	C10—C9—C14—C13	1.9 (2)
C1—C2—C7—O1	1.16 (16)	C8—C9—C14—C13	−179.25 (14)
C3—C2—C7—C6	0.0 (2)

Symmetry code: (i) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱ	0.93	2.52	3.347 (2)	148

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClFO₂S
M_r	308.74
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.7088 (5), 8.5241 (5), 11.6369 (7)
α, β, γ (°)	74.572 (3), 70.893 (3), 67.109 (3)
V (Å³)	657.13 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.25 × 0.22 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.895, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	10607, 3020, 2629
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.03
No. of reflections	3020
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.52	3.347 (2)	148.2

Symmetry code: (i) −x, −y+1, −z+1.

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