Crystal structure of 5-chloro-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814017966

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o991-o992

doi:10.1107/S1600536814017966

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Crystal structure of 5-chloro-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi ^a 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

Edited by O. Blacque, University of Zürich, Switzerland (Received 24 July 2014; accepted 5 August 2014; online 9 August 2014)

In the title compound, C₁₅H₁₀ClFO₂S, the dihedral angle between the plane of the benzofuran ring system [r.m.s. deviation = 0.013 (1) Å] and that of the 3-fluorophenyl ring [r.m.s. deviation = 0.005 (1) Å] is 31.36 (5)°. In the crystal, molecules are linked by two different pairs of C—H⋯O hydrogen bonds, forming inversion dimers.

Keywords: crystal structure; benzofuran; 3-fluorophenyl; C—H⋯O hydrogen bonds.

CCDC reference: 1017893

1. Related literature

For the pharmaceutical properties of compounds containing the benzofuran moiety, see: Aslam et al. (2009 ); Choi et al. (2003 ); Galal et al. (2009 ); 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-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2009 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₀ClFO₂S
M_r = 308.74
Triclinic, $[P \overline 1]$
a = 8.0038 (1) Å
b = 8.4322 (1) Å
c = 10.6782 (2) Å
α = 88.933 (1)°
β = 81.008 (1)°
γ = 66.859 (1)°
V = 653.81 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 K
0.47 × 0.34 × 0.33 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.813, T_max = 0.863
11737 measured reflections
3124 independent reflections
2887 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.07
3124 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.57	3.3470 (18)	139
C14—H14⋯O2ⁱⁱ	0.95	2.59	3.4884 (17)	157
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1017893

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814017966/zq2226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017966/zq2226Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814017966/zq2226Isup3.cml

checkCIF report

Comment top

Recently, a number of benzofuran compounds have drawn much attention owing to their interesting pharmaceutical properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009; Galal et al., 2009; Khan et al., 2005), and potential inhibitors of β-amyloid formation (Choi et al., 2003, Ono et al., 2002). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing project of 2-aryl-5-chloro-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl substituent in 2-position (Choi et al., 2009), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-fluorophenyl ring is 31.36 (5)°. In the crystal structure (Fig. 2), molecules are linked by two different pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers.

Related literature top

For the pharmaceutical properties of compounds containing a benzofuran unit, see: Aslam et al. (2009); Choi et al. (2003); Galal et al. (2009); 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-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2009).

Experimental top

The starting material 5-chloro-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of the starting material (322 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution (2 X 20 mL) and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 73% (248 mg); m.p. 483–484 K; R_f = 0.48 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (120 mg) in acetone (20 mL) at room temperature.

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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. 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.
	Fig. 2. A view of the C—H···O hydrogen bonds (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 + 1, - y, - z + 1].

5-Chloro-2-(3-fluorophenyl)-3-methylsulfinyl-1- benzofuran top

Crystal data top

C₁₅H₁₀ClFO₂S	Z = 2
M_r = 308.74	F(000) = 316
Triclinic, P1	D_x = 1.568 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0038 (1) Å	Cell parameters from 6836 reflections
b = 8.4322 (1) Å	θ = 2.6–28.5°
c = 10.6782 (2) Å	µ = 0.46 mm⁻¹
α = 88.933 (1)°	T = 173 K
β = 81.008 (1)°	Block, colourless
γ = 66.859 (1)°	0.47 × 0.34 × 0.33 mm
V = 653.81 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3124 independent reflections
Radiation source: rotating anode	2887 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.022
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.0°, θ_min = 1.9°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.813, T_max = 0.863	l = −14→13
11737 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) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0458P)² + 0.2424P] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₅H₁₀ClFO₂S	γ = 66.859 (1)°
M_r = 308.74	V = 653.81 (2) Å³
Triclinic, P1	Z = 2
a = 8.0038 (1) Å	Mo Kα radiation
b = 8.4322 (1) Å	µ = 0.46 mm⁻¹
c = 10.6782 (2) Å	T = 173 K
α = 88.933 (1)°	0.47 × 0.34 × 0.33 mm
β = 81.008 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3124 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2887 reflections with I > 2σ(I)
T_min = 0.813, T_max = 0.863	R_int = 0.022
11737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
3124 reflections	Δρ_min = −0.44 e Å⁻³
182 parameters

Special details top

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.23 (d, J = 2.04 Hz, 1H), 7.62 (d, J = 7.88 Hz, 1H), 7.54-7.58 (m, 1H), 7.45-7.52 (m, 2H), 7.38 (dd, J = 8.88 and 2.04 Hz, 1H), 7.16-7.22 (m, 1H), 3.11 (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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.82187 (5)	−0.13963 (5)	−0.02027 (3)	0.03515 (11)
S1	0.21038 (4)	0.30346 (4)	0.39543 (3)	0.02300 (10)
F1	0.53226 (14)	0.29209 (13)	0.95736 (8)	0.0395 (2)
O1	0.70635 (13)	0.13881 (12)	0.49383 (9)	0.0234 (2)
O2	0.17787 (15)	0.16956 (13)	0.32625 (11)	0.0325 (2)
C1	0.44633 (17)	0.21871 (16)	0.40865 (12)	0.0210 (3)
C2	0.59652 (17)	0.10631 (16)	0.31628 (12)	0.0210 (3)
C3	0.61509 (18)	0.04393 (17)	0.19238 (13)	0.0231 (3)
H3	0.5120	0.0719	0.1499	0.028*
C4	0.79058 (19)	−0.06027 (18)	0.13484 (13)	0.0252 (3)
C5	0.94567 (19)	−0.10505 (18)	0.19490 (14)	0.0275 (3)
H5	1.0635	−0.1775	0.1510	0.033*
C6	0.92781 (19)	−0.04413 (18)	0.31773 (14)	0.0265 (3)
H6	1.0308	−0.0728	0.3605	0.032*
C7	0.75209 (18)	0.06058 (16)	0.37470 (13)	0.0221 (3)
C8	0.51944 (17)	0.23358 (16)	0.51261 (13)	0.0214 (3)
C9	0.44315 (18)	0.32961 (17)	0.63441 (12)	0.0216 (3)
C10	0.29269 (19)	0.48798 (18)	0.64645 (13)	0.0256 (3)
H10	0.2383	0.5349	0.5740	0.031*
C11	0.2218 (2)	0.57761 (18)	0.76298 (14)	0.0281 (3)
H11	0.1182	0.6846	0.7703	0.034*
C12	0.3016 (2)	0.51149 (19)	0.86908 (14)	0.0296 (3)
H12	0.2542	0.5717	0.9495	0.036*
C13	0.4517 (2)	0.35607 (19)	0.85427 (13)	0.0270 (3)
C14	0.52576 (18)	0.26207 (17)	0.74107 (13)	0.0235 (3)
H14	0.6293	0.1551	0.7350	0.028*
C15	0.2148 (2)	0.4624 (2)	0.28245 (17)	0.0365 (4)
H15A	0.3053	0.4062	0.2070	0.055*
H15B	0.2488	0.5481	0.3205	0.055*
H15C	0.0927	0.5199	0.2581	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0340 (2)	0.0413 (2)	0.02564 (19)	−0.01237 (16)	0.00258 (14)	−0.00911 (14)
S1	0.01657 (16)	0.02380 (17)	0.02762 (18)	−0.00635 (12)	−0.00525 (12)	0.00218 (12)
F1	0.0448 (6)	0.0467 (5)	0.0251 (4)	−0.0123 (4)	−0.0156 (4)	0.0027 (4)
O1	0.0190 (4)	0.0254 (5)	0.0236 (5)	−0.0056 (4)	−0.0057 (4)	−0.0006 (4)
O2	0.0296 (5)	0.0282 (5)	0.0451 (6)	−0.0133 (4)	−0.0166 (5)	0.0030 (4)
C1	0.0169 (6)	0.0214 (6)	0.0233 (6)	−0.0058 (5)	−0.0038 (5)	0.0009 (5)
C2	0.0181 (6)	0.0204 (6)	0.0238 (6)	−0.0069 (5)	−0.0034 (5)	0.0025 (5)
C3	0.0220 (6)	0.0244 (6)	0.0232 (6)	−0.0091 (5)	−0.0048 (5)	0.0016 (5)
C4	0.0268 (7)	0.0245 (6)	0.0236 (6)	−0.0104 (5)	−0.0008 (5)	−0.0017 (5)
C5	0.0206 (6)	0.0255 (6)	0.0316 (7)	−0.0058 (5)	0.0007 (5)	−0.0016 (5)
C6	0.0189 (6)	0.0257 (6)	0.0326 (7)	−0.0058 (5)	−0.0057 (5)	0.0008 (5)
C7	0.0213 (6)	0.0213 (6)	0.0233 (6)	−0.0077 (5)	−0.0045 (5)	0.0009 (5)
C8	0.0178 (6)	0.0201 (6)	0.0248 (6)	−0.0058 (5)	−0.0039 (5)	0.0021 (5)
C9	0.0205 (6)	0.0231 (6)	0.0226 (6)	−0.0099 (5)	−0.0044 (5)	0.0005 (5)
C10	0.0248 (7)	0.0250 (6)	0.0265 (7)	−0.0082 (5)	−0.0067 (5)	0.0018 (5)
C11	0.0252 (7)	0.0249 (6)	0.0306 (7)	−0.0065 (5)	−0.0026 (5)	−0.0036 (5)
C12	0.0303 (7)	0.0326 (7)	0.0259 (7)	−0.0132 (6)	−0.0019 (6)	−0.0052 (5)
C13	0.0296 (7)	0.0330 (7)	0.0231 (7)	−0.0155 (6)	−0.0095 (5)	0.0040 (5)
C14	0.0214 (6)	0.0246 (6)	0.0258 (7)	−0.0096 (5)	−0.0055 (5)	0.0017 (5)
C15	0.0326 (8)	0.0312 (7)	0.0499 (10)	−0.0138 (6)	−0.0176 (7)	0.0173 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7418 (14)	C6—C7	1.3800 (19)
S1—O2	1.4866 (11)	C6—H6	0.9500
S1—C1	1.7652 (13)	C8—C9	1.4568 (18)
S1—C15	1.7937 (15)	C9—C10	1.3943 (18)
F1—C13	1.3584 (16)	C9—C14	1.4049 (18)
O1—C7	1.3724 (16)	C10—C11	1.385 (2)
O1—C8	1.3745 (15)	C10—H10	0.9500
C1—C8	1.3625 (18)	C11—C12	1.388 (2)
C1—C2	1.4439 (17)	C11—H11	0.9500
C2—C7	1.3945 (18)	C12—C13	1.377 (2)
C2—C3	1.3972 (18)	C12—H12	0.9500
C3—C4	1.3794 (19)	C13—C14	1.372 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.402 (2)	C15—H15A	0.9800
C5—C6	1.383 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

O2—S1—C1	107.08 (6)	C1—C8—C9	133.92 (12)
O2—S1—C15	105.95 (7)	O1—C8—C9	115.20 (11)
C1—S1—C15	97.48 (7)	C10—C9—C14	119.61 (12)
C7—O1—C8	106.62 (10)	C10—C9—C8	121.37 (12)
C8—C1—C2	106.92 (11)	C14—C9—C8	119.01 (12)
C8—C1—S1	126.40 (10)	C11—C10—C9	120.64 (13)
C2—C1—S1	126.42 (10)	C11—C10—H10	119.7
C7—C2—C3	119.41 (12)	C9—C10—H10	119.7
C7—C2—C1	105.03 (11)	C10—C11—C12	120.19 (13)
C3—C2—C1	135.54 (12)	C10—C11—H11	119.9
C4—C3—C2	116.67 (12)	C12—C11—H11	119.9
C4—C3—H3	121.7	C13—C12—C11	118.02 (13)
C2—C3—H3	121.7	C13—C12—H12	121.0
C3—C4—C5	123.22 (13)	C11—C12—H12	121.0
C3—C4—Cl1	118.56 (11)	F1—C13—C14	117.86 (13)
C5—C4—Cl1	118.22 (11)	F1—C13—C12	118.28 (13)
C6—C5—C4	120.30 (13)	C14—C13—C12	123.86 (13)
C6—C5—H5	119.8	C13—C14—C9	117.67 (12)
C4—C5—H5	119.8	C13—C14—H14	121.2
C7—C6—C5	116.25 (12)	C9—C14—H14	121.2
C7—C6—H6	121.9	S1—C15—H15A	109.5
C5—C6—H6	121.9	S1—C15—H15B	109.5
O1—C7—C6	125.27 (12)	H15A—C15—H15B	109.5
O1—C7—C2	110.56 (11)	S1—C15—H15C	109.5
C6—C7—C2	124.14 (13)	H15A—C15—H15C	109.5
C1—C8—O1	110.86 (11)	H15B—C15—H15C	109.5

O2—S1—C1—C8	−138.71 (12)	C1—C2—C7—C6	−178.69 (13)
C15—S1—C1—C8	112.01 (13)	C2—C1—C8—O1	0.06 (15)
O2—S1—C1—C2	34.63 (13)	S1—C1—C8—O1	174.46 (9)
C15—S1—C1—C2	−74.66 (13)	C2—C1—C8—C9	178.33 (14)
C8—C1—C2—C7	0.43 (14)	S1—C1—C8—C9	−7.3 (2)
S1—C1—C2—C7	−173.96 (10)	C7—O1—C8—C1	−0.54 (14)
C8—C1—C2—C3	−178.15 (15)	C7—O1—C8—C9	−179.16 (11)
S1—C1—C2—C3	7.5 (2)	C1—C8—C9—C10	−30.9 (2)
C7—C2—C3—C4	−0.39 (19)	O1—C8—C9—C10	147.27 (12)
C1—C2—C3—C4	178.04 (14)	C1—C8—C9—C14	150.28 (15)
C2—C3—C4—C5	0.4 (2)	O1—C8—C9—C14	−31.51 (17)
C2—C3—C4—Cl1	−179.30 (10)	C14—C9—C10—C11	−1.3 (2)
C3—C4—C5—C6	−0.2 (2)	C8—C9—C10—C11	179.97 (13)
Cl1—C4—C5—C6	179.54 (11)	C9—C10—C11—C12	0.9 (2)
C4—C5—C6—C7	−0.1 (2)	C10—C11—C12—C13	0.1 (2)
C8—O1—C7—C6	178.70 (13)	C11—C12—C13—F1	178.95 (13)
C8—O1—C7—C2	0.83 (14)	C11—C12—C13—C14	−0.6 (2)
C5—C6—C7—O1	−177.52 (12)	F1—C13—C14—C9	−179.35 (12)
C5—C6—C7—C2	0.1 (2)	C12—C13—C14—C9	0.2 (2)
C3—C2—C7—O1	178.08 (11)	C10—C9—C14—C13	0.7 (2)
C1—C2—C7—O1	−0.78 (15)	C8—C9—C14—C13	179.52 (12)
C3—C2—C7—C6	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.57	3.3470 (18)	139
C14—H14···O2ⁱⁱ	0.95	2.59	3.4884 (17)	157

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.57	3.3470 (18)	138.9
C14—H14···O2ⁱⁱ	0.95	2.59	3.4884 (17)	156.8

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

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Volume 70| Part 9| September 2014| Pages o991-o992

doi:10.1107/S1600536814017966

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 5-chloro-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 5-chloro-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran