# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/439 data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 I N O2 S' _chemical_formula_weight 419.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4512(19) _cell_length_b 10.550(4) _cell_length_c 19.373(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.569(18) _cell_angle_gamma 90.00 _cell_volume 1723.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11.41 _cell_measurement_theta_max 13.33 _exptl_crystal_description 'cut block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.983 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC7S _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.201 _diffrn_reflns_number 4217 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3956 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC Diffractometer control' _computing_cell_refinement 'MSC Diffractometer control' _computing_data_reduction 'texsan' _computing_structure_solution 'SIR' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'charon' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. CH2 backbone of 9 membered ring is disordered. Modeled over 2 sites for three isotropic atoms with refinement of an occupancy parameter. No hydrogen atoms were added to the minor component. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.3650P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens calc _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0087(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3956 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1195 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.10413(5) 0.10480(4) 0.38214(2) 0.06733(19) Uani 1 d . . . S1 S -0.40651(17) -0.05510(19) 0.37334(9) 0.0739(5) Uani 1 d . . . O1 O -0.5044(5) -0.1448(6) 0.4055(3) 0.1047(17) Uani 1 d . . . O2 O -0.4718(5) 0.0172(6) 0.3155(2) 0.0966(16) Uani 1 d . . . N1 N -0.2561(5) -0.1349(5) 0.3447(2) 0.0575(11) Uani 1 d . . . C1 C -0.3302(8) 0.0484(7) 0.4369(3) 0.0790(18) Uani 1 d . . . H1A H -0.4151 0.0967 0.4546 0.095 Uiso 1 calc R . . H1B H -0.2558 0.1048 0.4174 0.095 Uiso 1 calc R . . H1C H -0.2777 0.0008 0.4738 0.095 Uiso 1 calc R . . C2 C -0.1501(6) -0.2051(5) 0.3907(2) 0.0484(12) Uani 1 d . . . C3 C -0.1823(7) -0.2676(5) 0.4508(3) 0.0623(14) Uani 1 d . . . H3 H -0.2837 -0.2675 0.4669 0.075 Uiso 1 calc R . . C4 C -0.0583(9) -0.3305(5) 0.4863(3) 0.0703(17) Uani 1 d . . . H4 H -0.0773 -0.3744 0.5265 0.084 Uiso 1 calc R . . C5 C 0.0901(8) -0.3292(5) 0.4634(3) 0.0701(16) Uani 1 d . . . H5 H 0.1719 -0.3706 0.4886 0.084 Uiso 1 calc R . . C6 C 0.1207(6) -0.2667(5) 0.4025(3) 0.0591(13) Uani 1 d . . . H6 H 0.2223 -0.2665 0.3866 0.071 Uiso 1 calc R . . C7 C -0.0007(6) -0.2055(4) 0.3665(2) 0.0451(11) Uani 1 d . . . C8 C 0.0022(5) -0.1318(4) 0.2993(2) 0.0458(11) Uani 1 d . . . H8 H 0.0246 -0.1930 0.2631 0.055 Uiso 1 calc R . . C9 C -0.1709(5) -0.0869(5) 0.2843(2) 0.0508(12) Uani 1 d . . . H9 H -0.1746 0.0060 0.2833 0.061 Uiso 1 calc R . . C10 C -0.2545(7) -0.1405(8) 0.2177(3) 0.081(2) Uani 1 d . . . H10A H -0.3684 -0.1380 0.2214 0.097 Uiso 0.699(16) calc PR . . H10B H -0.2235 -0.2283 0.2120 0.097 Uiso 0.699(16) calc PR . . C11 C -0.2088(14) -0.0600(12) 0.1514(6) 0.083(3) Uiso 0.699(16) d P . . H11A H -0.1848 0.0266 0.1651 0.100 Uiso 0.699(16) calc PR . . H11B H -0.2983 -0.0584 0.1175 0.100 Uiso 0.699(16) calc PR . . C11A C -0.194(3) -0.150(3) 0.1515(13) 0.082(8) Uiso 0.301(16) d P . . C12 C -0.0562(13) -0.1222(12) 0.1170(6) 0.090(4) Uiso 0.699(16) d P . . H12A H -0.0283 -0.1990 0.1425 0.108 Uiso 0.699(16) calc PR . . H12B H -0.0893 -0.1473 0.0702 0.108 Uiso 0.699(16) calc PR . . C12A C -0.131(3) -0.040(2) 0.1233(12) 0.076(7) Uiso 0.301(16) d P . . C13A C 0.016(4) 0.000(3) 0.1071(15) 0.095(9) Uiso 0.301(16) d P . . C13 C 0.0918(17) -0.0442(15) 0.1137(7) 0.108(4) Uiso 0.699(16) d P . . H13A H 0.1516 -0.0772 0.0765 0.130 Uiso 0.699(16) calc PR . . H13B H 0.0607 0.0417 0.1013 0.130 Uiso 0.699(16) calc PR . . C14 C 0.1919(10) -0.0387(8) 0.1725(4) 0.095(2) Uani 1 d . . . H14A H 0.2939 -0.0089 0.1588 0.114 Uiso 0.699(16) calc PR . . H14B H 0.2073 -0.1248 0.1891 0.114 Uiso 0.699(16) calc PR . . C15 C 0.1481(8) 0.0409(6) 0.2329(3) 0.0689(16) Uani 1 d . . . H15A H 0.0482 0.0829 0.2206 0.083 Uiso 1 calc R . . H15B H 0.2279 0.1063 0.2408 0.083 Uiso 1 calc R . . C16 C 0.1326(5) -0.0308(5) 0.2997(3) 0.0501(12) Uani 1 d . . . H16 H 0.2337 -0.0743 0.3102 0.060 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0669(3) 0.0633(3) 0.0707(3) -0.0128(2) -0.00468(17) -0.0095(2) S1 0.0376(7) 0.1042(12) 0.0810(11) 0.0053(9) 0.0114(7) 0.0058(8) O1 0.058(3) 0.134(4) 0.126(4) 0.008(3) 0.037(3) -0.017(3) O2 0.054(3) 0.149(5) 0.086(3) 0.015(3) -0.003(2) 0.034(3) N1 0.037(2) 0.083(3) 0.053(2) 0.004(2) 0.0041(18) -0.001(2) C1 0.072(4) 0.093(5) 0.074(4) -0.007(4) 0.017(3) 0.019(4) C2 0.054(3) 0.046(3) 0.045(3) -0.006(2) 0.002(2) -0.007(2) C3 0.074(4) 0.056(3) 0.059(3) -0.004(3) 0.013(3) -0.009(3) C4 0.113(5) 0.046(3) 0.053(3) 0.004(3) 0.012(3) 0.000(3) C5 0.094(5) 0.053(3) 0.062(4) 0.005(3) -0.006(3) 0.021(3) C6 0.058(3) 0.053(3) 0.066(3) 0.003(3) 0.001(3) 0.011(3) C7 0.049(3) 0.041(3) 0.044(3) -0.004(2) -0.001(2) -0.001(2) C8 0.045(3) 0.047(3) 0.044(3) -0.003(2) 0.000(2) 0.001(2) C9 0.037(2) 0.069(3) 0.046(3) 0.000(2) -0.002(2) -0.002(2) C10 0.057(3) 0.127(6) 0.057(3) -0.018(4) -0.010(3) -0.013(4) C14 0.114(6) 0.095(5) 0.080(5) 0.005(4) 0.035(4) -0.011(5) C15 0.075(4) 0.071(4) 0.062(3) 0.008(3) 0.013(3) -0.022(3) C16 0.036(2) 0.057(3) 0.058(3) 0.002(2) 0.004(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C16 2.168(5) . ? S1 O1 1.426(5) . ? S1 O2 1.438(5) . ? S1 N1 1.649(5) . ? S1 C1 1.739(7) . ? N1 C2 1.430(6) . ? N1 C9 1.499(6) . ? C2 C7 1.374(7) . ? C2 C3 1.379(7) . ? C3 C4 1.386(8) . ? C4 C5 1.356(9) . ? C5 C6 1.389(8) . ? C6 C7 1.367(7) . ? C7 C8 1.517(6) . ? C8 C16 1.533(7) . ? C8 C9 1.548(6) . ? C9 C10 1.540(7) . ? C10 C11 1.608(13) . ? C11 C12 1.626(18) . ? C11A C12A 1.40(4) . ? C12 C13 1.502(16) . ? C12A C13A 1.36(4) . ? C13 C14 1.376(14) . ? C14 C15 1.505(9) . ? C15 C16 1.512(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.3(3) . . ? O1 S1 N1 106.8(3) . . ? O2 S1 N1 106.0(3) . . ? O1 S1 C1 107.8(3) . . ? O2 S1 C1 109.1(4) . . ? N1 S1 C1 107.4(3) . . ? C2 N1 C9 110.4(4) . . ? C2 N1 S1 121.4(3) . . ? C9 N1 S1 120.5(4) . . ? C7 C2 C3 121.4(5) . . ? C7 C2 N1 110.0(4) . . ? C3 C2 N1 128.6(5) . . ? C2 C3 C4 117.7(5) . . ? C5 C4 C3 121.3(5) . . ? C4 C5 C6 120.5(5) . . ? C7 C6 C5 119.0(5) . . ? C6 C7 C2 120.2(5) . . ? C6 C7 C8 129.0(5) . . ? C2 C7 C8 110.8(4) . . ? C7 C8 C16 113.7(4) . . ? C7 C8 C9 104.6(4) . . ? C16 C8 C9 117.3(4) . . ? N1 C9 C10 108.2(4) . . ? N1 C9 C8 104.1(4) . . ? C10 C9 C8 115.0(5) . . ? C9 C10 C11 110.8(6) . . ? C10 C11 C12 110.5(9) . . ? C13 C12 C11 118.7(11) . . ? C13A C12A C11A 136(3) . . ? C14 C13 C12 117.3(11) . . ? C13 C14 C15 119.9(10) . . ? C14 C15 C16 115.2(6) . . ? C15 C16 C8 116.3(4) . . ? C15 C16 I1 108.7(4) . . ? C8 C16 I1 110.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C2 -60.0(5) . . . . ? O2 S1 N1 C2 171.9(4) . . . . ? C1 S1 N1 C2 55.5(5) . . . . ? O1 S1 N1 C9 153.6(4) . . . . ? O2 S1 N1 C9 25.5(5) . . . . ? C1 S1 N1 C9 -91.0(4) . . . . ? C9 N1 C2 C7 1.2(6) . . . . ? S1 N1 C2 C7 -148.3(4) . . . . ? C9 N1 C2 C3 -177.9(5) . . . . ? S1 N1 C2 C3 32.6(7) . . . . ? C7 C2 C3 C4 0.4(8) . . . . ? N1 C2 C3 C4 179.4(5) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C3 C4 C5 C6 -1.4(9) . . . . ? C4 C5 C6 C7 0.6(9) . . . . ? C5 C6 C7 C2 0.7(8) . . . . ? C5 C6 C7 C8 -179.7(5) . . . . ? C3 C2 C7 C6 -1.2(7) . . . . ? N1 C2 C7 C6 179.6(4) . . . . ? C3 C2 C7 C8 179.2(4) . . . . ? N1 C2 C7 C8 0.0(5) . . . . ? C6 C7 C8 C16 -51.5(7) . . . . ? C2 C7 C8 C16 128.1(4) . . . . ? C6 C7 C8 C9 179.3(5) . . . . ? C2 C7 C8 C9 -1.1(5) . . . . ? C2 N1 C9 C10 121.1(5) . . . . ? S1 N1 C9 C10 -89.2(5) . . . . ? C2 N1 C9 C8 -1.7(5) . . . . ? S1 N1 C9 C8 148.0(4) . . . . ? C7 C8 C9 N1 1.6(5) . . . . ? C16 C8 C9 N1 -125.4(4) . . . . ? C7 C8 C9 C10 -116.6(5) . . . . ? C16 C8 C9 C10 116.4(5) . . . . ? N1 C9 C10 C11 161.5(6) . . . . ? C8 C9 C10 C11 -82.5(8) . . . . ? C9 C10 C11 C12 92.1(9) . . . . ? C10 C11 C12 C13 -118.9(11) . . . . ? C11 C12 C13 C14 81.6(15) . . . . ? C12 C13 C14 C15 -74.8(15) . . . . ? C13 C14 C15 C16 120.1(9) . . . . ? C14 C15 C16 C8 -62.9(7) . . . . ? C14 C15 C16 I1 171.7(5) . . . . ? C7 C8 C16 C15 176.5(4) . . . . ? C9 C8 C16 C15 -61.0(6) . . . . ? C7 C8 C16 I1 -59.0(5) . . . . ? C9 C8 C16 I1 63.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.667 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.090 #===END