5-Chloro-2-(4-fluoro­phen­yl)-7-methyl-3-methyl­sulfinyl-1-benzo­furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536813013172

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o920

doi:10.1107/S1600536813013172

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5-Chloro-2-(4-fluorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^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

(Received 13 May 2013; accepted 14 May 2013; online 18 May 2013)

In the title compound, C₁₆H₁₂ClFO₂S, the 4-fluorophenyl ring makes a dihedral angle of 16.43 (4)° with the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by pairs of Cl⋯O contacts [3.1839 (12) Å] into inversion dimers, which are further packed into stacks along the b axis by weak C—H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂ClFO₂S
M_r = 322.77
Triclinic, $[P \overline 1]$
a = 7.5374 (3) Å
b = 9.7388 (3) Å
c = 10.7979 (4) Å
α = 106.902 (2)°
β = 90.605 (2)°
γ = 110.598 (2)°
V = 704.24 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 173 K
0.34 × 0.29 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.669, T_max = 0.746
13230 measured reflections
3505 independent reflections
3025 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.093
S = 1.04
3505 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2ⁱ	0.98	2.52	3.2305 (17)	129
Symmetry code: (i) x, y-1, z.

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013172/xu5706sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013172/xu5706Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013172/xu5706Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-chloro-7-methyl-1-benzofuran derivatives containing [2-(4-chlorophenyl)-3-methylsulfinyl] (Choi et al., 2010a) and [3-ethylsulfinyl-2-(4-fluorophenyl)] (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.012 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 16.43 (4)°. In the crystal structure (Fig. 2), molecules are connected by pairs of Cl···O halogen-bondings between the chlorine atom and the O atom of the S═O unit [Cl1···O2ⁱⁱ = 3.1839 (12) Å, C4—Cl1···O2ⁱⁱ = 173.77 (6)°] (Politzer et al., 2007) into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H···O hydrogen bonds (Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 291 mg, 1.3 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-fluorophenyl)-7-methyl-3-methylsulfanyl-1-benzofuran (368 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5 h, the mixture was washed with saturated sodium bicarbonate solution 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 462–463 K; R_f = 0.51 (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 acetone 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 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.
	Fig. 2. A view of the C—H···O and Cl···O 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; (ii) - x, - y + 1, - z; (iii) x, y + 1, z; (iv) -x, - y, - z.]

5-Chloro-2-(4-fluorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₆H₁₂ClFO₂S	Z = 2
M_r = 322.77	F(000) = 332
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Melting point = 462–463 K
a = 7.5374 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7388 (3) Å	Cell parameters from 5632 reflections
c = 10.7979 (4) Å	θ = 2.4–28.4°
α = 106.902 (2)°	µ = 0.43 mm⁻¹
β = 90.605 (2)°	T = 173 K
γ = 110.598 (2)°	Block, colourless
V = 704.24 (4) Å³	0.34 × 0.29 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3505 independent reflections
Radiation source: rotating anode	3025 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.669, T_max = 0.746	l = −14→14
13230 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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0509P)² + 0.2009P] where P = (F_o² + 2F_c²)/3
3505 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₂ClFO₂S	γ = 110.598 (2)°
M_r = 322.77	V = 704.24 (4) Å³
Triclinic, P1	Z = 2
a = 7.5374 (3) Å	Mo Kα radiation
b = 9.7388 (3) Å	µ = 0.43 mm⁻¹
c = 10.7979 (4) Å	T = 173 K
α = 106.902 (2)°	0.34 × 0.29 × 0.17 mm
β = 90.605 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3505 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3025 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.746	R_int = 0.029
13230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	Δρ_max = 0.38 e Å⁻³
3505 reflections	Δρ_min = −0.30 e Å⁻³
192 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
Cl1	−0.06877 (6)	0.24551 (4)	−0.05566 (3)	0.03248 (11)
S1	0.31257 (5)	0.77726 (4)	0.43961 (3)	0.02701 (11)
F1	0.57470 (16)	0.77811 (14)	1.05273 (9)	0.0546 (3)
O1	0.18785 (14)	0.36631 (11)	0.48724 (9)	0.0232 (2)
O2	0.16474 (17)	0.78460 (13)	0.35249 (12)	0.0385 (3)
C1	0.25080 (19)	0.58204 (15)	0.43038 (13)	0.0224 (3)
C2	0.15601 (19)	0.45115 (15)	0.31599 (13)	0.0218 (3)
C3	0.0986 (2)	0.43012 (16)	0.18618 (13)	0.0243 (3)
H3	0.1224	0.5150	0.1538	0.029*
C4	0.0055 (2)	0.27967 (16)	0.10758 (13)	0.0247 (3)
C5	−0.0335 (2)	0.15197 (16)	0.15232 (13)	0.0248 (3)
H5	−0.1000	0.0510	0.0939	0.030*
C6	0.02366 (19)	0.17061 (15)	0.28075 (13)	0.0230 (3)
C7	0.11853 (19)	0.32240 (15)	0.35776 (13)	0.0213 (3)
C8	0.26620 (19)	0.52538 (16)	0.53022 (13)	0.0229 (3)
C9	−0.0088 (2)	0.03846 (16)	0.33323 (15)	0.0297 (3)
H9A	0.1114	0.0228	0.3428	0.045*
H9B	−0.1042	−0.0555	0.2728	0.045*
H9C	−0.0550	0.0617	0.4185	0.045*
C10	0.34642 (19)	0.59406 (16)	0.66751 (13)	0.0242 (3)
C11	0.4761 (2)	0.74628 (18)	0.71675 (15)	0.0308 (3)
H11	0.5137	0.8072	0.6601	0.037*
C12	0.5504 (2)	0.8094 (2)	0.84709 (16)	0.0356 (3)
H12	0.6359	0.9139	0.8813	0.043*
C13	0.4979 (2)	0.7178 (2)	0.92584 (14)	0.0351 (4)
C14	0.3715 (2)	0.5673 (2)	0.88172 (15)	0.0343 (3)
H14	0.3382	0.5069	0.9390	0.041*
C15	0.2938 (2)	0.50556 (18)	0.75203 (14)	0.0275 (3)
H15	0.2040	0.4023	0.7201	0.033*
C16	0.5173 (2)	0.79549 (19)	0.35447 (18)	0.0394 (4)
H16A	0.4814	0.7153	0.2691	0.059*
H16B	0.6164	0.7836	0.4052	0.059*
H16C	0.5665	0.8976	0.3424	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0459 (2)	0.0299 (2)	0.01946 (17)	0.01465 (16)	−0.00394 (14)	0.00412 (14)
S1	0.0368 (2)	0.01850 (17)	0.02544 (19)	0.01193 (14)	0.00111 (14)	0.00443 (14)
F1	0.0573 (7)	0.0654 (8)	0.0226 (5)	0.0083 (6)	−0.0117 (5)	0.0057 (5)
O1	0.0287 (5)	0.0202 (5)	0.0203 (5)	0.0094 (4)	−0.0008 (4)	0.0055 (4)
O2	0.0474 (7)	0.0327 (6)	0.0430 (7)	0.0214 (5)	−0.0013 (5)	0.0151 (5)
C1	0.0264 (6)	0.0189 (6)	0.0216 (6)	0.0099 (5)	0.0005 (5)	0.0041 (5)
C2	0.0237 (6)	0.0194 (6)	0.0227 (6)	0.0094 (5)	0.0014 (5)	0.0056 (5)
C3	0.0309 (7)	0.0220 (7)	0.0220 (6)	0.0120 (6)	0.0015 (5)	0.0074 (5)
C4	0.0295 (7)	0.0265 (7)	0.0193 (6)	0.0131 (6)	0.0005 (5)	0.0056 (5)
C5	0.0268 (7)	0.0200 (6)	0.0245 (7)	0.0086 (5)	0.0001 (5)	0.0030 (5)
C6	0.0248 (6)	0.0204 (6)	0.0254 (7)	0.0104 (5)	0.0038 (5)	0.0071 (5)
C7	0.0241 (6)	0.0220 (6)	0.0193 (6)	0.0106 (5)	0.0008 (5)	0.0062 (5)
C8	0.0233 (6)	0.0211 (6)	0.0236 (6)	0.0092 (5)	0.0015 (5)	0.0046 (5)
C9	0.0391 (8)	0.0206 (7)	0.0304 (7)	0.0110 (6)	0.0050 (6)	0.0094 (6)
C10	0.0232 (6)	0.0284 (7)	0.0214 (6)	0.0125 (5)	0.0009 (5)	0.0051 (5)
C11	0.0301 (7)	0.0312 (8)	0.0261 (7)	0.0066 (6)	−0.0005 (6)	0.0078 (6)
C12	0.0315 (8)	0.0346 (8)	0.0293 (8)	0.0058 (6)	−0.0039 (6)	0.0018 (7)
C13	0.0325 (8)	0.0472 (10)	0.0194 (7)	0.0135 (7)	−0.0043 (6)	0.0035 (6)
C14	0.0362 (8)	0.0429 (9)	0.0261 (7)	0.0151 (7)	0.0017 (6)	0.0136 (7)
C15	0.0287 (7)	0.0293 (7)	0.0250 (7)	0.0120 (6)	0.0014 (5)	0.0078 (6)
C16	0.0399 (9)	0.0303 (8)	0.0474 (10)	0.0098 (7)	0.0114 (7)	0.0153 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7432 (14)	C6—C9	1.4975 (18)
Cl1—O2ⁱ	3.1839 (12)	C8—C10	1.4597 (19)
S1—O2	1.4848 (11)	C9—H9A	0.9800
S1—C1	1.7628 (13)	C9—H9B	0.9800
S1—C16	1.7863 (17)	C9—H9C	0.9800
F1—C13	1.3541 (17)	C10—C11	1.395 (2)
O1—C7	1.3749 (15)	C10—C15	1.399 (2)
O1—C8	1.3771 (16)	C11—C12	1.382 (2)
C1—C8	1.3669 (18)	C11—H11	0.9500
C1—C2	1.4443 (19)	C12—C13	1.370 (2)
C2—C7	1.3920 (18)	C12—H12	0.9500
C2—C3	1.3971 (18)	C13—C14	1.373 (2)
C3—C4	1.379 (2)	C14—C15	1.382 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.4004 (19)	C15—H15	0.9500
C5—C6	1.3884 (19)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.3845 (19)	C16—H16C	0.9800

C4—Cl1—O2ⁱ	173.77 (6)	C6—C9—H9B	109.5
O2—S1—C1	107.35 (7)	H9A—C9—H9B	109.5
O2—S1—C16	106.18 (8)	C6—C9—H9C	109.5
C1—S1—C16	97.46 (7)	H9A—C9—H9C	109.5
C7—O1—C8	106.81 (10)	H9B—C9—H9C	109.5
C8—C1—C2	107.29 (12)	C11—C10—C15	118.93 (13)
C8—C1—S1	127.30 (11)	C11—C10—C8	121.50 (13)
C2—C1—S1	125.16 (10)	C15—C10—C8	119.56 (13)
C7—C2—C3	119.26 (12)	C12—C11—C10	120.69 (14)
C7—C2—C1	104.92 (12)	C12—C11—H11	119.7
C3—C2—C1	135.81 (12)	C10—C11—H11	119.7
C4—C3—C2	116.44 (12)	C13—C12—C11	118.45 (15)
C4—C3—H3	121.8	C13—C12—H12	120.8
C2—C3—H3	121.8	C11—C12—H12	120.8
C3—C4—C5	123.30 (13)	F1—C13—C12	118.53 (15)
C3—C4—Cl1	118.71 (10)	F1—C13—C14	118.54 (15)
C5—C4—Cl1	117.99 (11)	C12—C13—C14	122.93 (14)
C6—C5—C4	121.04 (13)	C13—C14—C15	118.52 (14)
C6—C5—H5	119.5	C13—C14—H14	120.7
C4—C5—H5	119.5	C15—C14—H14	120.7
C7—C6—C5	114.78 (12)	C14—C15—C10	120.46 (14)
C7—C6—C9	121.71 (12)	C14—C15—H15	119.8
C5—C6—C9	123.49 (13)	C10—C15—H15	119.8
O1—C7—C6	124.18 (11)	S1—C16—H16A	109.5
O1—C7—C2	110.65 (12)	S1—C16—H16B	109.5
C6—C7—C2	125.16 (12)	H16A—C16—H16B	109.5
C1—C8—O1	110.30 (12)	S1—C16—H16C	109.5
C1—C8—C10	134.92 (13)	H16A—C16—H16C	109.5
O1—C8—C10	114.78 (11)	H16B—C16—H16C	109.5
C6—C9—H9A	109.5

O2—S1—C1—C8	−140.84 (13)	C1—C2—C7—O1	−1.49 (15)
C16—S1—C1—C8	109.57 (14)	C3—C2—C7—C6	−1.2 (2)
O2—S1—C1—C2	32.66 (14)	C1—C2—C7—C6	178.13 (13)
C16—S1—C1—C2	−76.94 (13)	C2—C1—C8—O1	0.18 (15)
C8—C1—C2—C7	0.79 (15)	S1—C1—C8—O1	174.61 (10)
S1—C1—C2—C7	−173.79 (10)	C2—C1—C8—C10	179.48 (14)
C8—C1—C2—C3	179.96 (15)	S1—C1—C8—C10	−6.1 (2)
S1—C1—C2—C3	5.4 (2)	C7—O1—C8—C1	−1.10 (14)
C7—C2—C3—C4	0.47 (19)	C7—O1—C8—C10	179.45 (11)
C1—C2—C3—C4	−178.61 (15)	C1—C8—C10—C11	−17.7 (2)
C2—C3—C4—C5	0.6 (2)	O1—C8—C10—C11	161.60 (13)
C2—C3—C4—Cl1	−179.68 (10)	C1—C8—C10—C15	162.80 (15)
C3—C4—C5—C6	−1.1 (2)	O1—C8—C10—C15	−17.93 (18)
Cl1—C4—C5—C6	179.22 (10)	C15—C10—C11—C12	−0.5 (2)
C4—C5—C6—C7	0.36 (19)	C8—C10—C11—C12	179.93 (14)
C4—C5—C6—C9	−178.16 (13)	C10—C11—C12—C13	1.8 (2)
C8—O1—C7—C6	−178.00 (13)	C11—C12—C13—F1	178.17 (15)
C8—O1—C7—C2	1.63 (14)	C11—C12—C13—C14	−1.5 (3)
C5—C6—C7—O1	−179.67 (12)	F1—C13—C14—C15	−179.72 (14)
C9—C6—C7—O1	−1.1 (2)	C12—C13—C14—C15	0.0 (2)
C5—C6—C7—C2	0.8 (2)	C13—C14—C15—C10	1.3 (2)
C9—C6—C7—C2	179.31 (13)	C11—C10—C15—C14	−1.0 (2)
C3—C2—C7—O1	179.17 (11)	C8—C10—C15—C14	178.50 (13)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱⁱ	0.98	2.52	3.2305 (17)	129

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClFO₂S
M_r	322.77
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.5374 (3), 9.7388 (3), 10.7979 (4)
α, β, γ (°)	106.902 (2), 90.605 (2), 110.598 (2)
V (Å³)	704.24 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.34 × 0.29 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13230, 3505, 3025
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.093, 1.04
No. of reflections	3505
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱ	0.98	2.52	3.2305 (17)	129.3

Symmetry code: (i) x, y−1, z.

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

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