3-(4-Methoxy­benz­yl)-1-benzothio­phene

Abstract

In the title compound, C₁₆H₁₄OS, the dihedral angle between the benzothio­phene ring system and the benzene ring is 72.41 (12)°. A weak inter­molecular C—H⋯π inter­action from the benzene ring to the benzothio­phene ring system is observed in the crystal structure.

Related literature

For the biological activity of thio­phene derivatives, see: Bonini et al. (2005 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶). For related structures, see: Gunasekaran et al. (2009 ▶); Umadevi et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

• C₁₆H₁₄OS

• M _r = 254.33

• Monoclinic,

• a = 8.0158 (6) Å

• b = 10.8230 (9) Å

• c = 8.1219 (6) Å

• β = 112.563 (4)°

• V = 650.68 (9) ų

• Z = 2

• Mo Kα radiation

• μ = 0.23 mm⁻¹

• T = 295 K

• 0.25 × 0.20 × 0.20 mm

Data collection

• Bruker SMART APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.946, T _max = 0.954

• 6033 measured reflections

• 2946 independent reflections

• 2721 reflections with I > 2σ(I)

• R _int = 0.171

Refinement

• R[F ² > 2σ(F ²)] = 0.066

• wR(F ²) = 0.176

• S = 1.06

• 2946 reflections

• 164 parameters

• 2 restraints

• H-atom parameters constrained

• Δρ_max = 0.35 e Å⁻³

• Δρ_min = −0.48 e Å⁻³

• Absolute structure: Flack (1983 ▶), 1337 Friedel pairs

• Flack parameter: −0.04 (11)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cgi	0.93	2.83	3.617 (2)	143

Symmetry code: (i) .

supplementary crystallographic information

Comment

Thiophene derivatives exhibit anti-HIV PR inhibitors (Bonini et al., 2005) and anti-breast cancer (Brault et al., 2005) activities. In addition, some of the benzo[b]thiophene derivatives shows significant antimicrobial and anti-inflammatory activities (Isloora et al., 2010).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Gunasekaran et al., 2009; Umadevi et al., 2009). The dihedral angle between the two benzene rings is 71.93 (8)°. The C1—S1 and C8—S1 bond distances are 1.738 (3) and 1.734 (3) Å respectively, which are comparable to the literature value of 1.712 (2) Å (Allen et al., 1987).

The crystal packing is stabilized by a weak C—H···π interaction [C14—H14···Cg (-1+x, y, -1+z), Table 1; Cg is the centroid of the ring defined by the atoms C1—C6] .

Experimental

To a solution of 1-(bromomethyl)-4-methoxybenzene (0.7 g, 3.48 mmol) in dry 1,2-dichloroethane (20 ml) ZnBr₂ (0.23 g, 1.02 mmol) and benzo[b]thiophene (0.7 g, 5.22 mmol) were added. It was then stirred at room temperature for 6 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by column chromatographic purification (n-hexane/ethyl acetate 94:6) afforded the product as a colourless crystal.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic C—H, C—H = 0.97 Å and U_iso(H) = 1.2U_eq(C) for CH₂, C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for CH₃.

Figures

Fig. 1.

The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C16H14OS	F(000) = 268
Mr = 254.33	Dx = 1.298 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4241 reflections
a = 8.0158 (6) Å	θ = 2.7–28.3°
b = 10.8230 (9) Å	µ = 0.23 mm−1
c = 8.1219 (6) Å	T = 295 K
β = 112.563 (4)°	Block, colourless
V = 650.68 (9) Å3	0.25 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEXII CCD diffractometer	2946 independent reflections
Radiation source: fine-focus sealed tube	2721 reflections with I > 2σ(I)
graphite	Rint = 0.171
Detector resolution: 0 pixels mm-1	θmax = 28.3°, θmin = 1.9°
ω and φ scans	h = −10→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→14
Tmin = 0.946, Tmax = 0.954	l = −10→10
6033 measured reflections

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.1211P)2 + 0.025P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2946 reflections	Δρmax = 0.35 e Å−3
164 parameters	Δρmin = −0.48 e Å−3
2 restraints	Absolute structure: Flack (1983), 1337 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (11)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9043 (4)	0.0721 (3)	0.6766 (3)	0.0493 (6)
C2	1.0778 (5)	0.0242 (3)	0.7621 (4)	0.0607 (7)
H2	1.0969	−0.0510	0.8219	0.073*
C3	1.2203 (5)	0.0925 (4)	0.7547 (5)	0.0671 (9)
H3	1.3374	0.0627	0.8111	0.081*
C4	1.1926 (5)	0.2048 (4)	0.6648 (5)	0.0616 (7)
H4	1.2912	0.2494	0.6634	0.074*
C5	1.0204 (4)	0.2504 (3)	0.5777 (4)	0.0513 (6)
H5	1.0025	0.3250	0.5165	0.062*
C6	0.8728 (3)	0.1837 (2)	0.5821 (3)	0.0423 (5)
C7	0.6844 (3)	0.2155 (2)	0.5029 (3)	0.0433 (5)
C8	0.5818 (4)	0.1302 (3)	0.5405 (4)	0.0488 (5)
H8	0.4568	0.1362	0.5004	0.059*
C9	0.6202 (4)	0.3311 (3)	0.3944 (4)	0.0557 (6)
H9A	0.6662	0.3315	0.3000	0.067*
H9B	0.6716	0.4018	0.4703	0.067*
C10	0.4183 (4)	0.3466 (3)	0.3119 (3)	0.0497 (6)
C11	0.3305 (4)	0.4346 (3)	0.3745 (4)	0.0532 (6)
H11	0.3975	0.4844	0.4704	0.064*
C12	0.1454 (4)	0.4492 (3)	0.2967 (4)	0.0542 (6)
H12	0.0899	0.5101	0.3387	0.065*
C13	0.0417 (4)	0.3743 (3)	0.1570 (3)	0.0470 (6)
C14	0.1274 (4)	0.2862 (3)	0.0923 (3)	0.0517 (6)
H14	0.0605	0.2357	−0.0028	0.062*
C15	0.3130 (4)	0.2744 (3)	0.1708 (4)	0.0563 (7)
H15	0.3690	0.2153	0.1265	0.068*
C16	−0.2496 (5)	0.3249 (5)	−0.0572 (6)	0.0793 (11)
H16A	−0.2253	0.3485	−0.1597	0.119*
H16B	−0.3746	0.3397	−0.0799	0.119*
H16C	−0.2233	0.2386	−0.0332	0.119*
O1	−0.1408 (3)	0.3948 (3)	0.0910 (3)	0.0653 (6)
S1	0.70297 (12)	0.00836 (7)	0.67020 (11)	0.0601 (2)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0614 (14)	0.0440 (15)	0.0452 (11)	−0.0010 (11)	0.0235 (10)	−0.0009 (10)
C2	0.0703 (18)	0.0529 (17)	0.0552 (15)	0.0134 (14)	0.0201 (12)	0.0062 (12)
C3	0.0586 (16)	0.074 (2)	0.0644 (16)	0.0158 (15)	0.0191 (13)	−0.0042 (15)
C4	0.0546 (14)	0.0643 (18)	0.0702 (15)	−0.0037 (14)	0.0286 (12)	−0.0104 (16)
C5	0.0569 (14)	0.0447 (14)	0.0579 (13)	−0.0035 (11)	0.0283 (11)	−0.0016 (10)
C6	0.0517 (12)	0.0365 (12)	0.0417 (9)	−0.0009 (9)	0.0213 (9)	−0.0032 (8)
C7	0.0511 (11)	0.0377 (12)	0.0430 (10)	−0.0007 (10)	0.0203 (8)	−0.0007 (9)
C8	0.0549 (13)	0.0414 (13)	0.0537 (11)	−0.0035 (11)	0.0250 (10)	−0.0008 (10)
C9	0.0563 (14)	0.0430 (15)	0.0645 (14)	0.0016 (12)	0.0196 (11)	0.0102 (12)
C10	0.0580 (14)	0.0403 (13)	0.0511 (12)	0.0057 (11)	0.0211 (10)	0.0068 (10)
C11	0.0699 (16)	0.0396 (14)	0.0490 (11)	−0.0006 (12)	0.0218 (11)	−0.0037 (10)
C12	0.0717 (17)	0.0425 (14)	0.0544 (12)	0.0106 (12)	0.0309 (12)	−0.0033 (11)
C13	0.0583 (14)	0.0412 (13)	0.0447 (10)	0.0112 (10)	0.0233 (10)	0.0049 (9)
C14	0.0597 (14)	0.0473 (15)	0.0442 (10)	0.0103 (12)	0.0155 (10)	−0.0068 (10)
C15	0.0633 (16)	0.0526 (17)	0.0528 (12)	0.0161 (12)	0.0221 (11)	−0.0033 (11)
C16	0.0594 (19)	0.078 (3)	0.090 (2)	0.0062 (16)	0.0179 (17)	−0.014 (2)
O1	0.0607 (12)	0.0675 (16)	0.0672 (12)	0.0173 (11)	0.0238 (9)	−0.0048 (11)
S1	0.0723 (4)	0.0462 (4)	0.0659 (4)	−0.0059 (3)	0.0312 (3)	0.0108 (3)

Geometric parameters (Å, °)

C1—C2	1.394 (5)	C9—H9A	0.9700
C1—C6	1.401 (4)	C9—H9B	0.9700
C1—S1	1.738 (3)	C10—C15	1.376 (4)
C2—C3	1.381 (6)	C10—C11	1.392 (4)
C2—H2	0.9300	C11—C12	1.380 (4)
C3—C4	1.391 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.383 (4)
C4—C5	1.379 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—O1	1.369 (4)
C5—C6	1.398 (4)	C13—C14	1.391 (4)
C5—H5	0.9300	C14—C15	1.381 (4)
C6—C7	1.438 (4)	C14—H14	0.9300
C7—C8	1.347 (4)	C15—H15	0.9300
C7—C9	1.503 (4)	C16—O1	1.406 (5)
C8—S1	1.734 (3)	C16—H16A	0.9600
C8—H8	0.9300	C16—H16B	0.9600
C9—C10	1.504 (4)	C16—H16C	0.9600
C2—C1—C6	121.9 (3)	C10—C9—H9B	108.5
C2—C1—S1	127.2 (3)	H9A—C9—H9B	107.5
C6—C1—S1	110.9 (2)	C15—C10—C11	117.3 (3)
C3—C2—C1	117.6 (3)	C15—C10—C9	121.3 (3)
C3—C2—H2	121.2	C11—C10—C9	121.5 (3)
C1—C2—H2	121.2	C12—C11—C10	121.1 (3)
C2—C3—C4	121.5 (3)	C12—C11—H11	119.4
C2—C3—H3	119.2	C10—C11—H11	119.4
C4—C3—H3	119.2	C11—C12—C13	120.7 (2)
C5—C4—C3	120.6 (3)	C11—C12—H12	119.6
C5—C4—H4	119.7	C13—C12—H12	119.6
C3—C4—H4	119.7	O1—C13—C12	116.2 (2)
C4—C5—C6	119.5 (3)	O1—C13—C14	124.9 (3)
C4—C5—H5	120.2	C12—C13—C14	118.9 (3)
C6—C5—H5	120.2	C15—C14—C13	119.3 (3)
C5—C6—C1	118.9 (3)	C15—C14—H14	120.3
C5—C6—C7	128.2 (2)	C13—C14—H14	120.3
C1—C6—C7	112.9 (2)	C10—C15—C14	122.7 (3)
C8—C7—C6	111.2 (2)	C10—C15—H15	118.7
C8—C7—C9	127.0 (3)	C14—C15—H15	118.7
C6—C7—C9	121.8 (2)	O1—C16—H16A	109.5
C7—C8—S1	114.3 (2)	O1—C16—H16B	109.5
C7—C8—H8	122.9	H16A—C16—H16B	109.5
S1—C8—H8	122.9	O1—C16—H16C	109.5
C7—C9—C10	114.9 (2)	H16A—C16—H16C	109.5
C7—C9—H9A	108.5	H16B—C16—H16C	109.5
C10—C9—H9A	108.5	C13—O1—C16	117.8 (3)
C7—C9—H9B	108.5	C8—S1—C1	90.76 (14)
C6—C1—C2—C3	1.6 (4)	C6—C7—C9—C10	176.5 (2)
S1—C1—C2—C3	−178.0 (2)	C7—C9—C10—C15	−71.9 (4)
C1—C2—C3—C4	−0.3 (5)	C7—C9—C10—C11	108.3 (3)
C2—C3—C4—C5	−0.9 (5)	C15—C10—C11—C12	−0.6 (4)
C3—C4—C5—C6	0.8 (5)	C9—C10—C11—C12	179.2 (3)
C4—C5—C6—C1	0.5 (4)	C10—C11—C12—C13	1.7 (4)
C4—C5—C6—C7	179.1 (3)	C11—C12—C13—O1	179.0 (3)
C2—C1—C6—C5	−1.7 (4)	C11—C12—C13—C14	−1.9 (4)
S1—C1—C6—C5	177.95 (19)	O1—C13—C14—C15	−179.9 (3)
C2—C1—C6—C7	179.4 (3)	C12—C13—C14—C15	1.1 (4)
S1—C1—C6—C7	−0.9 (3)	C11—C10—C15—C14	−0.3 (5)
C5—C6—C7—C8	−178.0 (3)	C9—C10—C15—C14	179.9 (3)
C1—C6—C7—C8	0.8 (3)	C13—C14—C15—C10	0.0 (5)
C5—C6—C7—C9	1.7 (4)	C12—C13—O1—C16	176.7 (3)
C1—C6—C7—C9	−179.6 (2)	C14—C13—O1—C16	−2.4 (5)
C6—C7—C8—S1	−0.3 (3)	C7—C8—S1—C1	−0.2 (2)
C9—C7—C8—S1	−179.9 (2)	C2—C1—S1—C8	−179.7 (3)
C8—C7—C9—C10	−3.9 (4)	C6—C1—S1—C8	0.6 (2)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cgi	0.93	2.83	3.617 (2)	143

Symmetry codes: (i) x−1, y, z−1.