In the title compound C16H14OS the dihedral angle between the benzothio-phene ring system and the benzene ring is 72. Monoclinic = 8.0158 (6) ? = 10.8230 (9) ? = 8.1219 (6) ? β = 112.563 (4)° = 650.68 (9) ?3 = 2 Mo = 295 K 0.25 × 0.20 × 0.20 mm Data collection Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (> 2σ(= 1.06 2946 reflections 164 parameters 2 restraints H-atom parameters constrained Δρmax = 0.35 e ??3 Δρmin = ?0.48 e ??3 Absolute structure: Flack (1983 ?) 1337 Friedel pairs Flack parameter: ?0.04 (11) Data collection: (Bruker 2004 ?); cell refinement: (Bruker 2004 ?); Ambrisentan data reduction: (Sheldrick 2008 ?); program(s) used to refine structure: (Sheldrick 2008 ?); molecular graphics: (Spek 2009 ?); software used to prepare material for publication: (-1+is usually 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 (20 ml) ZnBr2 (0.23 Ambrisentan g 1.02 mmol) and benzo[b]thiophene (0.7 g 5.22 mmol) were added. It was then stirred at room heat for 6 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) made up of 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 BMP2B H atoms were positioned geometrically and refined using driving model with C-H = 0.93 ? and = 254.33= 8.0158 (6) ?θ = 2.7-28.3°= 10.8230 (9) ?μ = 0.23 mm?1= 8.1219 (6) ?= 295 Kβ = Ambrisentan 112.563 (4)°Block colourless= 650.68 (9) ?30.25 × 0.20 × 0.20 mm= 2 View it in a separate window Data collection Bruker SMART APEXII CCD diffractometer2946 independent reflectionsRadiation source: fine-focus sealed tube2721 reflections with > 2σ(= ?10→9Absorption correction: multi-scan (= ?12→14= ?10→106033 measured reflections View it in a separate window Refinement Refinement on = 1/[σ2(= (= 1.06(Δ/σ)max < 0.0012946 reflectionsΔρmax = 0.35 e ??3164 parametersΔρmin = ?0.48 e ??32 restraintsAbsolute structure: Flack (1983) 1337 Friedel pairsPrimary atom site location: structure-invariant direct methodsFlack parameter: ?0.04 (11) View it in a separate windows Fractional atomic coordinates and isotropic or equivalent isotropic Ambrisentan displacement parameters (?2) xyzUiso*/UeqC10.9043 (4)0.0721 (3)0.6766 (3)0.0493 (6)C21.0778 (5)0.0242 (3)0.7621 (4)0.0607 (7)H21.0969?0.05100.82190.073*C31.2203 (5)0.0925 (4)0.7547 (5)0.0671 (9)H31.33740.06270.81110.081*C41.1926 (5)0.2048 (4)0.6648 (5)0.0616 (7)H41.29120.24940.66340.074*C51.0204 (4)0.2504 (3)0.5777 (4)0.0513 (6)H51.00250.32500.51650.062*C60.8728 (3)0.1837 (2)0.5821 (3)0.0423 (5)C70.6844 (3)0.2155 (2)0.5029 (3)0.0433 (5)C80.5818 (4)0.1302 (3)0.5405 (4)0.0488 (5)H80.45680.13620.50040.059*C90.6202 (4)0.3311 (3)0.3944 (4)0.0557 (6)H9A0.66620.33150.30000.067*H9B0.67160.40180.47030.067*C100.4183 (4)0.3466 (3)0.3119 (3)0.0497 (6)C110.3305 (4)0.4346 (3)0.3745 (4)0.0532 (6)H110.39750.48440.47040.064*C120.1454 (4)0.4492 (3)0.2967 (4)0.0542 (6)H120.08990.51010.33870.065*C130.0417 (4)0.3743 (3)0.1570 (3)0.0470 (6)C140.1274 (4)0.2862 (3)0.0923 (3)0.0517 (6)H140.06050.2357?0.00280.062*C150.3130 (4)0.2744 (3)0.1708 (4)0.0563 (7)H150.36900.21530.12650.068*C16?0.2496 (5)0.3249 (5)?0.0572 (6)0.0793 (11)H16A?0.22530.3485?0.15970.119*H16B?0.37460.3397?0.07990.119*H16C?0.22330.2386?0.03320.119*O1?0.1408 (3)0.3948 (3)0.0910 (3)0.0653 (6)S10.70297 (12)0.00836 (7)0.67020 (11)0.0601 (2) View it in a separate windows Atomic displacement parameters (?2) U11U22U33U12U13U23C10.0614 (14)0.0440 (15)0.0452 (11)?0.0010 (11)0.0235 (10)?0.0009 (10)C20.0703 (18)0.0529 (17)0.0552 (15)0.0134 (14)0.0201 (12)0.0062 (12)C30.0586 (16)0.074 (2)0.0644 (16)0.0158 (15)0.0191 (13)?0.0042 (15)C40.0546 (14)0.0643 (18)0.0702 (15)?0.0037 (14)0.0286 (12)?0.0104 (16)C50.0569 (14)0.0447 (14)0.0579 (13)?0.0035 (11)0.0283 (11)?0.0016 (10)C60.0517 (12)0.0365 (12)0.0417 (9)?0.0009 (9)0.0213 (9)?0.0032 (8)C70.0511 (11)0.0377.