Structure of 9-oxo-l-thioxanthenecarbonitrile 10,10-dioxide

Abstract

C[subscript 14]H[subscript 7]NO[subscript 3]S , M[subscript r] = 269[middle dot]3, triclinic, P1, a = 8[middle dot]069 (3), b = 8[middle dot]654 (3), c = 8[middle dot]973 (3) Angstrom, [alpha] = 102[middle dot]12 (3), [beta] = 91[middle dot]16 (3), [gamma] = 108[middle dot]19 (3) °, V = 579[middle dot]5 (3) [Angstrom][superscript 3], [zeta] = 2, D[subscript x] = 1[middle dot]543 g cm[superscript -3], Mo [kappa alpha] ([lambda] = 0[middle dot]71073[Angstrom]), [mu] =2[middle dot]68 cm[superscript -1], F(000)=276, T = 298 K, R = 0[middle dot]0429 and wR = 0[middle dot]0494 for 1854 reflections [I_> 3[sigma](I)]. The bonding between C(9) and C(9a) and C(8a) is asymmetrical. C(9)---C(9a) [1[middle dot]499 (3)[Angstrom]] is longer than C(9)--C(8a) [1[middle dot]475 (3) [Angstrom]] due to the electron-withdrawing power of the cyano group. A considerable repulsion between the carbonyl and the cyano groups is accommodated by distortion of the cyano group and the geometry around C(1). Angle C(11)--C(1)--C(9a) [122[middle dot]4 (2) °] is larger than C(11)---C(1)--C(2) [116[middle dot]2 (2)°]. Additionally, angle C(1)---C(11)---N(11) is 174[middle dot]0(2) °, compared to an angle of 180 ° around an sp-hybridized carbon, and the N atom is pointing away from the carbonyl group. The dihedral angle between the two arene rings is 170[middle dot]1 (2) °.