C 16H21NO5S, triclinic, P1 (no. 2), a = 7.3395(9) Å, b = 11.103(1) Å, c = 11.391(1) Å, a = 107.933(9)°, b = 95.12(1)°, g = 99.96(1)°, V = 859.8 Å 3 , Z = 2, R gt(F) = 0.062, wRref(F 2 ) = 0.218, T = 293 K.
Source of materialFirstly, the 4-tert-butyl-2-(4-nitrophenylsulfanyl)cyclohexanone was obtained from the reaction of 2-bromo-4-tert-butyl-cyclohexanone and 4-nitrobenzenethiol [1], then to a solution of the product (2.0 g, 6.5 mmol) in methanol (10 mL) and CH2Cl2 (3 mL) at 273 K was added slowly a solution of hydrogen peroxide (30 %, 3.7 mL, 32.5 mmol) and selenium dioxide (0.72 g, 6.5 mmol) in methanol [2]. After stirring for 5 h, a saturated aqueous NaCl solution (40 mL) was added and the crude product was extracted with CH2Cl2 (3 × 30 mL). The organic layer was dried over anhydrous MgSO4. The solvent was removed and the amorphous yellow solid was recrystallized from ethanol giving 1.61 g of the title compound (4.74 mmol, 72 % yield, m.p. 405-406 K). Crystals were obtained by slow evaporation from anhydrous ethanol at 298 K. Elemental analysis: found C, 56.23 %; H, 6.03 %; N, 3.99 %; calc. for C16H21NO5S C, 56.62 %; H, 6.24 %; N, 4.13 %.
Experimental detailsThe high Uii values for C14 C16 can be ascribed to the rotational disorder of the tert-butyl group.
DiscussionThe cyclohexanone ring is in a slightly distorted chair conformation, the Cremer and Poples ring-puckering [3] parameters being: q2 = 0.0715 (6)