# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Shengming Ma' 'Xueshi Hao' 'Xian Huang' _publ_contact_author_name 'Dr Shengming Ma' _publ_contact_author_address ; 354 Fenglin Lu Shanghai 200032 CHINA ; _publ_contact_author_email MASM@PUB.SIOC.AC.CN _publ_requested_journal 'Chemical Communications' _publ_section_title ; Highly Regio- and Stereoselective Four-Component Iodoamination of Se-Substituted Allenes. An Efficient Synthesis of N-(3-Organoseleno-2-iodo-2(Z)-propenyl) acetamides ; data_cd21142 _database_code_CSD 186925 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 N O Se I' _chemical_formula_weight 380.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9005(10) _cell_length_b 13.2791(12) _cell_length_c 9.8573(9) _cell_angle_alpha 90.00 _cell_angle_beta 114.263(2) _cell_angle_gamma 90.00 _cell_volume 1300.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2160 _cell_measurement_theta_min 5.120 _cell_measurement_theta_max 47.733 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.435 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.164 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 5.236 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.5625 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7761 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.22 _reflns_number_total 3019 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3019 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.827 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.002 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se Se 0.67003(5) 1.00119(4) 0.30201(6) 0.06958(18) Uani 1 1 d . . . I I 0.90349(3) 1.03472(2) 0.14285(3) 0.05992(13) Uani 1 1 d . . . O1 O 0.8730(3) 0.7980(2) -0.2209(3) 0.0552(7) Uani 1 1 d . . . C1 C 0.6655(4) 0.9216(4) 0.1397(5) 0.0557(11) Uani 1 1 d . . . C2 C 0.7464(4) 0.9291(3) 0.0740(4) 0.0476(10) Uani 1 1 d . . . C3 C 0.7356(5) 0.8607(4) -0.0521(5) 0.0565(12) Uani 1 1 d . . . N1 N 0.8450(4) 0.7896(3) -0.0085(4) 0.0508(9) Uani 1 1 d . . . C5 C 0.9029(4) 0.7614(3) -0.0984(5) 0.0453(10) Uani 1 1 d . . . C6 C 1.0088(4) 0.6806(3) -0.0374(5) 0.0702(13) Uani 1 1 d . . . H6A H 0.9670 0.6156 -0.0621 0.105 Uiso 1 1 calc R . . H6B H 1.0535 0.6871 0.0688 0.105 Uiso 1 1 calc R . . H6C H 1.0732 0.6877 -0.0800 0.105 Uiso 1 1 calc R . . C7 C 0.5471(4) 0.9208(3) 0.3511(5) 0.0473(10) Uani 1 1 d . . . C8 C 0.5870(4) 0.8862(3) 0.4941(5) 0.0539(11) Uani 1 1 d . . . H8 H 0.6733 0.8998 0.5649 0.065 Uiso 1 1 calc R . . C9 C 0.4996(5) 0.8315(3) 0.5325(5) 0.0644(13) Uani 1 1 d . . . H9 H 0.5263 0.8089 0.6298 0.077 Uiso 1 1 calc R . . C10 C 0.3757(6) 0.8104(4) 0.4305(6) 0.0767(15) Uani 1 1 d . . . H10 H 0.3174 0.7724 0.4574 0.092 Uiso 1 1 calc R . . C11 C 0.3339(5) 0.8443(4) 0.2863(6) 0.0798(15) Uani 1 1 d . . . H11 H 0.2478 0.8297 0.2159 0.096 Uiso 1 1 calc R . . C12 C 0.4205(4) 0.9000(3) 0.2475(5) 0.0632(12) Uani 1 1 d . . . H12 H 0.3930 0.9235 0.1506 0.076 Uiso 1 1 calc R . . H1 H 0.600(4) 0.872(3) 0.112(5) 0.087(17) Uiso 1 1 d . . . H2 H 0.739(4) 0.894(3) -0.129(4) 0.049(12) Uiso 1 1 d . . . H3 H 0.643(4) 0.823(3) -0.094(5) 0.070(13) Uiso 1 1 d . . . H4 H 0.872(4) 0.763(3) 0.077(5) 0.065(14) Uiso 1 1 d . . . 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 Se 0.0922(4) 0.0631(3) 0.0792(4) -0.0276(3) 0.0612(3) -0.0221(3) I 0.0733(2) 0.0595(2) 0.0589(2) -0.00360(14) 0.03923(17) -0.01128(15) O1 0.076(2) 0.0660(19) 0.0317(17) 0.0002(14) 0.0302(16) -0.0006(15) C1 0.067(3) 0.055(3) 0.055(3) -0.010(2) 0.035(3) -0.010(2) C2 0.064(3) 0.046(2) 0.042(2) -0.0033(19) 0.031(2) 0.001(2) C3 0.072(3) 0.063(3) 0.045(3) -0.006(2) 0.035(3) -0.005(3) N1 0.076(3) 0.051(2) 0.034(2) 0.0010(17) 0.032(2) 0.0030(18) C5 0.059(3) 0.040(2) 0.042(3) -0.0110(19) 0.025(2) -0.014(2) C6 0.084(3) 0.071(3) 0.061(3) -0.007(3) 0.035(3) 0.010(3) C7 0.051(3) 0.049(2) 0.050(3) -0.005(2) 0.029(2) 0.007(2) C8 0.062(3) 0.052(3) 0.046(3) -0.006(2) 0.020(2) 0.012(2) C9 0.091(4) 0.056(3) 0.056(3) 0.004(2) 0.040(3) 0.009(3) C10 0.098(4) 0.068(3) 0.091(4) -0.003(3) 0.067(4) -0.007(3) C11 0.059(3) 0.101(4) 0.083(4) -0.003(3) 0.033(3) -0.013(3) C12 0.065(3) 0.077(3) 0.050(3) 0.009(2) 0.025(3) 0.006(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 Se C1 1.902(4) . ? Se C7 1.923(4) . ? I C2 2.099(4) . ? O1 C5 1.215(4) . ? C1 C2 1.295(5) . ? C2 C3 1.504(6) . ? C3 N1 1.441(6) . ? N1 C5 1.336(5) . ? C5 C6 1.508(5) . ? C7 C12 1.366(5) . ? C7 C8 1.373(5) . ? C8 C9 1.369(6) . ? C9 C10 1.341(6) . ? C10 C11 1.379(7) . ? C11 C12 1.371(6) . ? 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 C1 Se C7 97.08(18) . . ? C2 C1 Se 126.2(4) . . ? C1 C2 C3 121.9(4) . . ? C1 C2 I 121.5(3) . . ? C3 C2 I 116.6(3) . . ? N1 C3 C2 112.0(4) . . ? C5 N1 C3 123.0(4) . . ? O1 C5 N1 122.7(4) . . ? O1 C5 C6 121.9(4) . . ? N1 C5 C6 115.3(4) . . ? C12 C7 C8 119.7(4) . . ? C12 C7 Se 121.3(3) . . ? C8 C7 Se 119.0(3) . . ? C9 C8 C7 119.9(4) . . ? C10 C9 C8 120.3(5) . . ? C9 C10 C11 120.6(5) . . ? C12 C11 C10 119.4(5) . . ? C7 C12 C11 120.1(4) . . ? 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 C7 Se C1 C2 -168.1(4) . . . . ? Se C1 C2 C3 178.8(3) . . . . ? Se C1 C2 I 0.8(6) . . . . ? C1 C2 C3 N1 -108.7(5) . . . . ? I C2 C3 N1 69.4(4) . . . . ? C2 C3 N1 C5 -142.4(4) . . . . ? C3 N1 C5 O1 4.4(6) . . . . ? C3 N1 C5 C6 -175.6(4) . . . . ? C1 Se C7 C12 -56.0(4) . . . . ? C1 Se C7 C8 125.6(3) . . . . ? C12 C7 C8 C9 -0.4(6) . . . . ? Se C7 C8 C9 178.0(3) . . . . ? C7 C8 C9 C10 0.9(6) . . . . ? C8 C9 C10 C11 -0.8(7) . . . . ? C9 C10 C11 C12 0.1(8) . . . . ? C8 C7 C12 C11 -0.2(6) . . . . ? Se C7 C12 C11 -178.6(3) . . . . ? C10 C11 C12 C7 0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 1.048 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.125