3-(4-Methoxy­benz­yl)-1-benzothio­phene

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.066
• wR factor = 0.176
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.170
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          5
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................      83.61 Perc.
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               2946
           Count of symmetry unique reflns         1613
           Completeness (_total/calc)            182.64%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1333
           Fraction of Friedel pairs measured     0.826
           Are heavy atom types Z>Si present        yes
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.12
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.20

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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] .

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).

S2. 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.

S3. 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.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

3-(4-Methoxybenzyl)-1-benzothiophene

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) Å^3	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 monochromator	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 F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.1211P)^2 + 0.025P] where P = (Fo^2 + 2Fc^2)/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	Absolute structure 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)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

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, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg^i	0.93	2.83	3.617 (2)	143

Symmetry code: (i) x−1, y, z−1.