3-(4-Chloro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran

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

doi:10.1107/S1600536810035932

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2551

doi:10.1107/S1600536810035932

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3-(4-Chlorophenylsulfinyl)-2,5-dimethyl-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 13 August 2010; accepted 7 September 2010; online 11 September 2010)

In the crystal structure of the title compound, C₁₆H₁₃ClO₂S, the 4-chlorophenyl ring is oriented approximately perpendicular to the benzofuran ring plane [dihedral angle = 82.45 (5)°]. In the crystal, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the structures of related 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ).

Experimental

Crystal data

C₁₆H₁₃ClO₂S
M_r = 304.77
Monoclinic, P 2₁ /c
a = 12.7673 (19) Å
b = 11.0206 (18) Å
c = 11.1232 (17) Å
β = 113.674 (6)°
V = 1433.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 173 K
0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.654, T_max = 0.746
12779 measured reflections
3542 independent reflections
3118 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.124
S = 1.03
3542 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1, C2, C7, O1, C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2ⁱ	0.96	2.51	3.366 (2)	148
C15—H15⋯O2ⁱⁱ	0.93	2.60	3.353 (2)	139
C13—H13⋯Cg1ⁱⁱⁱ	0.93	2.85	3.566 (2)	135
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: 10.1107/S1600536810035932/nc2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035932/nc2196Isup2.hkl

checkCIF report

Comment top

As a part of our study on the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran analogues (Choi et al., 2010a, b/), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.004 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-chlorophenyl ring is nearly perpendicular to the benzofuran plane with a dihedral angle of 82.45 (5)°. In the crystal structure weak intermolecular C—H···O hydrogen bonding and C—H···π interaction are found (Fig. 2 and Table 1).

Related literature top

For the structures of related 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2,5-dimethyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 77%, m.p. 440–441 K; R/_f = 0.71 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the solvent from a solution of the title compound in ethyl acetate 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 (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 and H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 2, y + 1/2, - z + 3/2; (ii) - x + 2, y -1/2, - z +3/2.]

3-(4-Chlorophenylsulfinyl)-2,5-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₃ClO₂S	F(000) = 632
M_r = 304.77	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8210 reflections
a = 12.7673 (19) Å	θ = 2.5–28.3°
b = 11.0206 (18) Å	µ = 0.41 mm⁻¹
c = 11.1232 (17) Å	T = 173 K
β = 113.674 (6)°	Block, colourless
V = 1433.4 (4) Å³	0.50 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3542 independent reflections
Radiation source: rotating anode	3118 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 = 1.7°
ϕ and ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.654, T_max = 0.746	l = −14→13
12779 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0772P)² + 0.5141P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3542 reflections	Δρ_max = 0.31 e Å⁻³
184 parameters	Δρ_min = −0.31 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: 0.014 (2)

Crystal data top

C₁₆H₁₃ClO₂S	V = 1433.4 (4) Å³
M_r = 304.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7673 (19) Å	µ = 0.41 mm⁻¹
b = 11.0206 (18) Å	T = 173 K
c = 11.1232 (17) Å	0.50 × 0.30 × 0.20 mm
β = 113.674 (6)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3542 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3118 reflections with I > 2σ(I)
T_min = 0.654, T_max = 0.746	R_int = 0.029
12779 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
3542 reflections	Δρ_min = −0.31 e Å⁻³
184 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	0.76980 (4)	0.23428 (4)	0.27031 (4)	0.04162 (15)
S	0.92673 (3)	0.68708 (4)	0.64073 (4)	0.02874 (14)
O1	0.66438 (10)	0.90669 (11)	0.50482 (12)	0.0371 (3)
O2	0.95961 (10)	0.64186 (13)	0.77732 (11)	0.0398 (3)
C1	0.79481 (13)	0.76039 (14)	0.59101 (14)	0.0261 (3)
C2	0.69064 (12)	0.71954 (15)	0.60000 (14)	0.0264 (3)
C3	0.65623 (13)	0.61696 (16)	0.64794 (15)	0.0303 (3)
H3	0.7071	0.5536	0.6850	0.036*
C4	0.54444 (14)	0.61099 (19)	0.63938 (17)	0.0386 (4)
C5	0.47007 (15)	0.7081 (2)	0.5827 (2)	0.0485 (5)
H5	0.3956	0.7033	0.5772	0.058*
C6	0.50216 (16)	0.8100 (2)	0.5347 (2)	0.0477 (5)
H6	0.4514	0.8734	0.4970	0.057*
C7	0.61371 (14)	0.81344 (16)	0.54552 (16)	0.0333 (4)
C8	0.77512 (14)	0.87155 (15)	0.53477 (15)	0.0315 (3)
C9	0.50414 (17)	0.5015 (2)	0.6895 (2)	0.0520 (5)
H9A	0.5632	0.4410	0.7170	0.078*
H9B	0.4368	0.4692	0.6209	0.078*
H9C	0.4867	0.5245	0.7627	0.078*
C10	0.84732 (19)	0.95889 (18)	0.50136 (19)	0.0452 (4)
H10A	0.8743	1.0205	0.5679	0.068*
H10B	0.8031	0.9958	0.4181	0.068*
H10C	0.9114	0.9170	0.4964	0.068*
C11	0.87780 (11)	0.55732 (14)	0.53501 (14)	0.0253 (3)
C12	0.82630 (14)	0.57394 (16)	0.40013 (15)	0.0319 (3)
H12	0.8142	0.6517	0.3646	0.038*
C13	0.79335 (14)	0.47361 (16)	0.31949 (15)	0.0324 (3)
H13	0.7581	0.4831	0.2289	0.039*
C14	0.81304 (12)	0.35892 (15)	0.37406 (15)	0.0272 (3)
C16	0.89862 (12)	0.44303 (15)	0.58916 (15)	0.0293 (3)
H16	0.9347	0.4336	0.6797	0.035*
C15	0.86562 (14)	0.34154 (16)	0.50817 (16)	0.0314 (3)
H15	0.8787	0.2637	0.5435	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0453 (3)	0.0364 (3)	0.0423 (3)	−0.00681 (17)	0.0167 (2)	−0.01106 (18)
S	0.0214 (2)	0.0302 (2)	0.0333 (2)	−0.00229 (13)	0.00965 (15)	−0.00328 (15)
O1	0.0419 (6)	0.0266 (6)	0.0358 (6)	0.0078 (5)	0.0084 (5)	−0.0007 (5)
O2	0.0369 (6)	0.0435 (7)	0.0287 (6)	0.0039 (5)	0.0025 (5)	−0.0033 (5)
C1	0.0274 (7)	0.0247 (7)	0.0260 (7)	0.0000 (5)	0.0106 (5)	−0.0024 (6)
C2	0.0236 (6)	0.0305 (8)	0.0239 (6)	0.0025 (5)	0.0084 (5)	−0.0040 (6)
C3	0.0254 (7)	0.0368 (9)	0.0285 (7)	−0.0012 (6)	0.0106 (6)	−0.0007 (6)
C4	0.0296 (8)	0.0552 (12)	0.0337 (8)	−0.0072 (7)	0.0155 (6)	−0.0082 (8)
C5	0.0261 (8)	0.0683 (14)	0.0529 (11)	0.0017 (8)	0.0177 (8)	−0.0129 (10)
C6	0.0315 (8)	0.0547 (12)	0.0513 (11)	0.0167 (8)	0.0106 (8)	−0.0075 (9)
C7	0.0323 (8)	0.0319 (9)	0.0326 (8)	0.0053 (6)	0.0097 (6)	−0.0066 (6)
C8	0.0389 (8)	0.0262 (8)	0.0264 (7)	−0.0010 (6)	0.0099 (6)	−0.0048 (6)
C9	0.0408 (10)	0.0737 (15)	0.0464 (10)	−0.0196 (10)	0.0226 (8)	−0.0039 (10)
C10	0.0619 (12)	0.0323 (10)	0.0402 (9)	−0.0122 (8)	0.0193 (8)	0.0001 (8)
C11	0.0206 (6)	0.0290 (7)	0.0289 (7)	0.0005 (5)	0.0128 (5)	−0.0009 (6)
C12	0.0385 (8)	0.0286 (8)	0.0291 (7)	0.0031 (6)	0.0141 (6)	0.0056 (6)
C13	0.0361 (8)	0.0362 (9)	0.0252 (7)	0.0021 (6)	0.0125 (6)	0.0028 (6)
C14	0.0238 (6)	0.0300 (8)	0.0300 (7)	−0.0009 (5)	0.0132 (6)	−0.0027 (6)
C16	0.0285 (7)	0.0326 (8)	0.0257 (7)	0.0035 (6)	0.0097 (6)	0.0048 (6)
C15	0.0325 (7)	0.0276 (8)	0.0331 (8)	0.0020 (6)	0.0122 (6)	0.0035 (6)

Geometric parameters (Å, º) top

Cl—C14	1.7355 (16)	C8—C10	1.480 (2)
S—O2	1.4902 (13)	C9—H9A	0.9600
S—C1	1.7457 (15)	C9—H9B	0.9600
S—C11	1.7966 (16)	C9—H9C	0.9600
O1—C8	1.372 (2)	C10—H10A	0.9600
O1—C7	1.384 (2)	C10—H10B	0.9600
C1—C8	1.352 (2)	C10—H10C	0.9600
C1—C2	1.445 (2)	C11—C16	1.375 (2)
C2—C7	1.387 (2)	C11—C12	1.387 (2)
C2—C3	1.394 (2)	C12—C13	1.379 (2)
C3—C4	1.393 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.381 (2)
C4—C5	1.401 (3)	C13—H13	0.9300
C4—C9	1.504 (3)	C14—C15	1.381 (2)
C5—C6	1.375 (3)	C16—C15	1.391 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.381 (3)	C15—H15	0.9300
C6—H6	0.9300

O2—S—C1	108.59 (7)	C4—C9—H9B	109.5
O2—S—C11	106.42 (8)	H9A—C9—H9B	109.5
C1—S—C11	97.08 (7)	C4—C9—H9C	109.5
C8—O1—C7	106.41 (13)	H9A—C9—H9C	109.5
C8—C1—C2	107.99 (14)	H9B—C9—H9C	109.5
C8—C1—S	122.84 (12)	C8—C10—H10A	109.5
C2—C1—S	129.17 (12)	C8—C10—H10B	109.5
C7—C2—C3	119.70 (14)	H10A—C10—H10B	109.5
C7—C2—C1	104.31 (14)	C8—C10—H10C	109.5
C3—C2—C1	135.99 (14)	H10A—C10—H10C	109.5
C4—C3—C2	118.93 (16)	H10B—C10—H10C	109.5
C4—C3—H3	120.5	C16—C11—C12	121.26 (15)
C2—C3—H3	120.5	C16—C11—S	119.15 (11)
C3—C4—C5	119.02 (18)	C12—C11—S	119.47 (12)
C3—C4—C9	120.41 (18)	C13—C12—C11	119.08 (15)
C5—C4—C9	120.57 (17)	C13—C12—H12	120.5
C6—C5—C4	123.03 (17)	C11—C12—H12	120.5
C6—C5—H5	118.5	C12—C13—C14	119.60 (14)
C4—C5—H5	118.5	C12—C13—H13	120.2
C5—C6—C7	116.50 (17)	C14—C13—H13	120.2
C5—C6—H6	121.8	C13—C14—C15	121.69 (15)
C7—C6—H6	121.8	C13—C14—Cl	118.62 (12)
C6—C7—O1	126.38 (17)	C15—C14—Cl	119.68 (13)
C6—C7—C2	122.83 (18)	C11—C16—C15	119.85 (14)
O1—C7—C2	110.79 (14)	C11—C16—H16	120.1
C1—C8—O1	110.50 (14)	C15—C16—H16	120.1
C1—C8—C10	133.36 (16)	C14—C15—C16	118.51 (15)
O1—C8—C10	116.14 (16)	C14—C15—H15	120.7
C4—C9—H9A	109.5	C16—C15—H15	120.7

O2—S—C1—C8	131.30 (14)	C1—C2—C7—O1	0.08 (17)
C11—S—C1—C8	−118.68 (14)	C2—C1—C8—O1	−0.52 (17)
O2—S—C1—C2	−48.63 (16)	S—C1—C8—O1	179.54 (10)
C11—S—C1—C2	61.39 (15)	C2—C1—C8—C10	179.19 (17)
C8—C1—C2—C7	0.26 (17)	S—C1—C8—C10	−0.7 (3)
S—C1—C2—C7	−179.80 (12)	C7—O1—C8—C1	0.56 (17)
C8—C1—C2—C3	−179.12 (17)	C7—O1—C8—C10	−179.21 (14)
S—C1—C2—C3	0.8 (3)	O2—S—C11—C16	−13.00 (13)
C7—C2—C3—C4	0.3 (2)	C1—S—C11—C16	−124.81 (12)
C1—C2—C3—C4	179.60 (16)	O2—S—C11—C12	171.00 (12)
C2—C3—C4—C5	0.1 (2)	C1—S—C11—C12	59.20 (13)
C2—C3—C4—C9	179.73 (16)	C16—C11—C12—C13	1.4 (2)
C3—C4—C5—C6	−0.1 (3)	S—C11—C12—C13	177.30 (12)
C9—C4—C5—C6	−179.70 (19)	C11—C12—C13—C14	−0.6 (2)
C4—C5—C6—C7	−0.3 (3)	C12—C13—C14—C15	−0.3 (2)
C5—C6—C7—O1	−179.62 (17)	C12—C13—C14—Cl	179.56 (12)
C5—C6—C7—C2	0.8 (3)	C12—C11—C16—C15	−1.3 (2)
C8—O1—C7—C6	179.97 (17)	S—C11—C16—C15	−177.26 (12)
C8—O1—C7—C2	−0.38 (17)	C13—C14—C15—C16	0.3 (2)
C3—C2—C7—C6	−0.7 (2)	Cl—C14—C15—C16	−179.50 (11)
C1—C2—C7—C6	179.74 (16)	C11—C16—C15—C14	0.5 (2)
C3—C2—C7—O1	179.58 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1, C2, C7, O1, C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2ⁱ	0.96	2.51	3.366 (2)	148
C15—H15···O2ⁱⁱ	0.93	2.60	3.353 (2)	139
C13—H13···Cg1ⁱⁱⁱ	0.93	2.85	3.566 (2)	135

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO₂S
M_r	304.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.7673 (19), 11.0206 (18), 11.1232 (17)
β (°)	113.674 (6)
V (Å³)	1433.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.654, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12779, 3542, 3118
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.124, 1.03
No. of reflections	3542
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

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

Cg1 is the centroid of the C1, C2, C7, O1, C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2ⁱ	0.96	2.51	3.366 (2)	147.9
C15—H15···O2ⁱⁱ	0.93	2.60	3.353 (2)	138.9
C13—H13···Cg1ⁱⁱⁱ	0.93	2.85	3.566 (2)	134.6

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+3/2, z−1/2.

Acknowledgements

This work was supported by Blue-Bio Industry RIC at Dongeui University as a RIC program under the Ministry of Knowledge Economy and Busan city.

References

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Volume 66| Part 10| October 2010| Page o2551

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