data_2010314 _journal_name_full 'Acta Crystallographica' _journal_year 1994 _journal_volume C50 _journal_page_first 1916 _journal_page_last 1919 _publ_section_title ; 2-Ethylthio-5-methyl-6,7,8,9,10,11,12,13,14,15-decahydrocyclododeca[b]indole: an Unexpected Product from the Demethylation of an Indole Using Fujita's Reagent ; loop_ _publ_author_name 'Ianelli, Sandra' 'Nardelli*, Mario' 'Belletti, Daniele' 'Caub\`ere, Caterine' 'Caub\`ere, Paul' "Jamart-Gr\'egoire, Brigitte" _chemical_formula_sum 'C21 H31 N S' _chemical_formula_analytical 'C21 H31 N S' _chemical_formula_weight 329.54 _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.183(5) _cell_length_b 7.831(2) _cell_length_c 9.213(4) _cell_angle_alpha 90. _cell_angle_beta 95.11(2) _cell_angle_gamma 90. _cell_volume 947.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.155 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs 0.0326 _refine_ls_wR_factor_obs 0.0716 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S1 0.15738(7) 0.1232(2) 0.57240(10) 0.0769(4) aniso . . S N1 0.4803(2) 0.5903(4) 0.8176(3) 0.0470(9) aniso . . N C1 0.2535(3) 0.2575(5) 0.6587(4) 0.0547(11) aniso . . C C2 0.3548(3) 0.2393(5) 0.6297(4) 0.0500(11) aniso . . C C3 0.4276(2) 0.3555(4) 0.6900(3) 0.0413(9) aniso . . C C4 0.5335(2) 0.3805(4) 0.6733(3) 0.0408(10) aniso . . C C5 0.5944(3) 0.2678(5) 0.5820(4) 0.0472(11) aniso . . C C6 0.6241(3) 0.0969(5) 0.6513(4) 0.0543(12) aniso . . C C7 0.7100(2) 0.1085(6) 0.7730(4) 0.0498(11) aniso . . C C8 0.8149(3) 0.1243(8) 0.7186(4) 0.0621(15) aniso . . C C9 0.9031(3) 0.1505(6) 0.8357(6) 0.0685(16) aniso . . C C10 0.8931(3) 0.3087(6) 0.9308(4) 0.0584(14) aniso . . C C11 0.8922(3) 0.4790(6) 0.8484(5) 0.0633(16) aniso . . C C12 0.8379(3) 0.6226(7) 0.9190(5) 0.0603(12) aniso . . C C13 0.7225(3) 0.5967(6) 0.9200(4) 0.0532(11) aniso . . C C14 0.6657(3) 0.6075(6) 0.7678(4) 0.0485(11) aniso . . C C15 0.5637(2) 0.5239(4) 0.7509(3) 0.0419(10) aniso . . C C16 0.3963(2) 0.4896(5) 0.7781(3) 0.0460(10) aniso . . C C17 0.2957(3) 0.5070(6) 0.8102(4) 0.0551(12) aniso . . C C18 0.2256(3) 0.3906(6) 0.7488(4) 0.0618(14) aniso . . C C19 0.1683(4) -0.0681(7) 0.6743(6) 0.0750(16) aniso . . C C20 0.0791(4) -0.1836(9) 0.6374(8) 0.090(2) aniso . . C C21 0.4773(4) 0.7468(7) 0.9015(7) 0.0703(18) aniso . . C H2 0.378(2) 0.151(5) 0.565(3) 0.059(11) iso . C2 H H51 0.652(2) 0.328(5) 0.561(3) 0.047(9) iso . C5 H H52 0.556(3) 0.249(6) 0.489(4) 0.072(11) iso . C5 H H61 0.642(3) 0.022(5) 0.578(4) 0.066(12) iso . C6 H H62 0.556(3) 0.045(5) 0.685(4) 0.068(12) iso . C6 H H71 0.710(3) 0.005(7) 0.845(5) 0.089(15) iso . C7 H H72 0.697(3) 0.206(5) 0.837(4) 0.049(10) iso . C7 H H81 0.813(3) 0.212(6) 0.654(4) 0.058(13) iso . C8 H H82 0.829(3) 0.021(7) 0.665(5) 0.073(13) iso . C8 H H91 0.963(3) 0.167(6) 0.786(4) 0.075(13) iso . C9 H H92 0.902(3) 0.055(5) 0.894(4) 0.063(13) iso . C9 H H101 0.951(2) 0.306(5) 1.006(4) 0.055(9) iso . C10 H H102 0.834(3) 0.310(5) 0.977(3) 0.051(10) iso . C10 H H111 0.859(2) 0.454(5) 0.761(4) 0.051(10) iso . C11 H H112 0.965(3) 0.510(6) 0.852(4) 0.084(13) iso . C11 H H121 0.873(2) 0.639(6) 1.022(4) 0.067(10) iso . C12 H H122 0.847(3) 0.730(6) 0.865(4) 0.073(13) iso . C12 H H131 0.699(3) 0.692(5) 0.987(4) 0.059(11) iso . C13 H H132 0.702(3) 0.477(6) 0.965(4) 0.071(13) iso . C13 H H141 0.664(3) 0.709(5) 0.745(4) 0.051(11) iso . C14 H H142 0.710(3) 0.544(4) 0.694(4) 0.055(10) iso . C14 H H17 0.278(2) 0.595(5) 0.862(3) 0.042(9) iso . C17 H H18 0.148(3) 0.407(5) 0.769(4) 0.079(12) iso . C18 H H191 0.182(3) -0.048(6) 0.776(5) 0.080(14) iso . C19 H H192 0.229(4) -0.118(7) 0.666(5) 0.100(19) iso . C19 H H201 0.066(4) -0.219(8) 0.524(6) 0.129(19) iso . C20 H H202 0.022(6) -0.112(11) 0.643(8) 0.19(4) iso . C20 H H203 0.089(5) -0.293(11) 0.683(8) 0.19(4) iso . C20 H H211 0.471(4) 0.712(8) 0.988(6) 0.12(3) iso . C21 H H212 0.534(4) 0.812(8) 0.893(6) 0.13(2) iso . C21 H H213 0.417(4) 0.818(8) 0.865(5) 0.14(2) iso . C21 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0569(5) 0.0910(8) 0.0782(6) 0.0221(7) -0.0204(4) -0.0246(6) N1 0.0483(13) 0.0445(17) 0.0481(14) -0.0063(14) 0.0030(11) 0.0039(13) C1 0.0443(18) 0.061(3) 0.057(2) 0.016(2) -0.0079(15) -0.0078(18) C2 0.0489(18) 0.054(2) 0.0456(18) 0.0057(18) -0.0052(15) -0.0015(17) C3 0.0417(15) 0.0430(18) 0.0381(15) 0.0018(15) -0.0033(12) 0.0023(14) C4 0.0409(15) 0.0407(18) 0.0396(16) 0.0023(15) -0.0031(13) 0.0024(14) C5 0.0455(17) 0.052(2) 0.0435(18) -0.0064(17) -0.0011(15) 0.0033(16) C6 0.0553(19) 0.045(2) 0.061(2) -0.015(2) -0.0048(16) 0.0052(18) C7 0.0535(17) 0.0421(19) 0.0525(18) -0.007(2) -0.0033(14) 0.0038(19) C8 0.0502(18) 0.072(3) 0.064(2) -0.013(3) -0.0004(16) 0.012(2) C9 0.051(2) 0.067(3) 0.085(3) -0.003(3) -0.010(2) 0.012(2) C10 0.051(2) 0.063(3) 0.059(2) -0.000(2) -0.0087(18) 0.0022(19) C11 0.047(2) 0.065(3) 0.077(3) 0.009(2) 0.002(2) -0.002(2) C12 0.0484(16) 0.050(2) 0.080(3) -0.001(3) -0.0102(17) -0.0065(19) C13 0.0504(17) 0.052(2) 0.0548(19) -0.009(2) -0.0076(15) -0.0037(18) C14 0.0486(17) 0.041(2) 0.0551(19) 0.003(2) -0.0017(14) -0.0056(17) C15 0.0441(15) 0.0404(18) 0.0400(16) 0.0019(15) -0.0033(13) 0.0011(14) C16 0.0435(15) 0.048(2) 0.0449(17) 0.0057(16) -0.0032(14) 0.0033(15) C17 0.0514(19) 0.059(3) 0.056(2) -0.000(2) 0.0086(16) 0.0093(19) C18 0.0402(18) 0.077(3) 0.068(2) 0.016(2) 0.0057(17) 0.0007(19) C19 0.072(3) 0.072(3) 0.079(3) 0.003(3) -0.007(3) -0.016(3) C20 0.083(4) 0.077(4) 0.110(5) -0.022(4) 0.018(3) -0.024(3) C21 0.075(3) 0.053(3) 0.084(3) -0.025(3) 0.009(3) 0.000(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.779(4) no S1 C19 1.767(6) no N1 C15 1.406(4) no N1 C16 1.381(4) no N1 C21 1.452(6) no C1 C2 1.392(5) no C1 C18 1.402(6) no C2 C3 1.402(5) no C2 H2 0.99(3) no C3 C4 1.431(4) no C3 C16 1.411(5) no C4 C5 1.501(5) no C4 C15 1.372(4) no C5 C6 1.519(5) no C5 H51 0.93(3) no C5 H52 0.97(3) no C6 C7 1.523(5) no C6 H61 0.94(4) no C6 H62 1.05(3) no C7 C8 1.517(5) no C7 H71 1.05(5) no C7 H72 0.99(3) no C8 C9 1.527(6) no C8 H81 0.91(4) no C8 H82 0.97(4) no C9 C10 1.530(7) no C9 H91 0.96(3) no C9 H92 0.92(4) no C10 C11 1.535(6) no C10 H101 0.98(3) no C10 H102 0.92(3) no C11 C12 1.511(7) no C11 H111 0.91(3) no C11 H112 0.99(4) no C12 C13 1.536(5) no C12 H121 1.03(3) no C12 H122 0.99(4) no C13 C14 1.532(5) no C13 H131 1.03(3) no C13 H132 1.07(4) no C14 C15 1.491(5) no C14 H141 0.82(4) no C14 H142 1.06(3) no C16 C17 1.391(5) no C17 C18 1.383(6) no C17 H17 0.88(3) no C18 H18 1.07(4) no C19 C20 1.498(8) no C19 H191 0.95(4) no C19 H192 0.89(5) no C20 H201 1.08(5) no C20 H202 0.94(7) no C20 H203 0.96(8) no C21 H211 0.85(6) no C21 H212 0.92(5) no C21 H213 1.01(5) no