Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Carl Schiesser' _publ_contact_author_name 'Carl Schiesser' _publ_contact_author_address ; School of Chemistry The University of Melbourne Bio21 Institute 30 Flemington Road The University of Melbourne Victoria 3010 AUSTRALIA ; _publ_contact_author_email CARLHS@UNIMELB.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and Related Compounds by Free-Radical Means ; # Attachment 'B515385A-crystal28.cif' data_tahli _database_code_depnum_ccdc_archive 'CCDC 288081' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O3 Se' _chemical_formula_weight 376.30 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.8305(8) _cell_length_b 13.532(2) _cell_length_c 26.210(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1713.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2574 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 21.75 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 10646 _diffrn_reflns_av_R_equivalents 0.1020 _diffrn_reflns_av_sigmaI/netI 0.1034 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.58 _reflns_number_total 3892 _reflns_number_gt 2601 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'WinGX SHELXTL' _computing_structure_refinement 'WinGX SHELXTL' _computing_molecular_graphics 'WinGX Ortep3' _computing_publication_material 'WinGX 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^)+(0.0133P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(14) _refine_ls_number_reflns 3892 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_restrained_S_all 0.810 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8222(7) 0.4354(2) 0.26888(15) 0.0402(8) Uani 1 1 d . . . C2 C 0.6300(7) 0.4640(2) 0.23159(16) 0.0427(9) Uani 1 1 d . . . C3 C 0.4980(11) 0.5537(2) 0.24002(14) 0.0555(9) Uani 1 1 d . . . H3 H 0.3681 0.5762 0.2165 0.067 Uiso 1 1 calc R . . C4 C 0.5544(11) 0.6089(3) 0.28156(18) 0.0666(13) Uani 1 1 d . . . H4 H 0.4635 0.6685 0.2872 0.080 Uiso 1 1 calc R . . C5 C 0.7490(11) 0.5750(3) 0.31519(18) 0.0687(13) Uani 1 1 d . . . H5 H 0.7904 0.6139 0.3434 0.082 Uiso 1 1 calc R . . C6 C 0.5681(7) 0.4027(2) 0.18708(14) 0.0407(9) Uani 1 1 d . . . C7 C 0.3534(8) 0.4329(2) 0.14937(15) 0.0505(10) Uani 1 1 d . . . H7A H 0.4273 0.4851 0.1279 0.061 Uiso 1 1 calc R . . H7B H 0.1946 0.4593 0.1675 0.061 Uiso 1 1 calc R . . C8 C 0.2611(8) 0.3487(3) 0.11627(15) 0.0526(10) Uani 1 1 d . . . H8 H 0.1975 0.2951 0.1379 0.063 Uiso 1 1 calc R . . H9A H 0.1057 0.3702 0.0957 0.063 Uiso 1 1 calc R . . C9 C 0.4830(9) 0.3109(3) 0.08199(13) 0.0499(8) Uani 1 1 d . . . C10 C 0.6751(11) 0.1670(3) 0.0453(2) 0.0859(15) Uani 1 1 d . . . H10A H 0.6455 0.1869 0.0101 0.103 Uiso 1 1 calc R . . H10B H 0.8593 0.1878 0.0554 0.103 Uiso 1 1 calc R . . C11 C 0.6499(18) 0.0618(3) 0.0498(3) 0.153(3) Uani 1 1 d . . . H11A H 0.4606 0.0429 0.0444 0.229 Uiso 1 1 calc R . . H11B H 0.7068 0.0417 0.0834 0.229 Uiso 1 1 calc R . . H11C H 0.7653 0.0304 0.0248 0.229 Uiso 1 1 calc R . . C12 C 1.2207(8) 0.3171(3) 0.32831(14) 0.0563(10) Uani 1 1 d . . . H12A H 1.4020 0.2879 0.3232 0.068 Uiso 1 1 calc R . . H12B H 1.2474 0.3857 0.3379 0.068 Uiso 1 1 calc R . . C13 C 1.0805(7) 0.2650(3) 0.37057(15) 0.0519(11) Uani 1 1 d . . . C14 C 1.1367(11) 0.1696(3) 0.38208(18) 0.0804(15) Uani 1 1 d . . . H14 H 1.2690 0.1356 0.3632 0.096 Uiso 1 1 calc R . . C15 C 1.0027(18) 0.1222(3) 0.4209(2) 0.1010(18) Uani 1 1 d . . . H15 H 1.0411 0.0561 0.4275 0.121 Uiso 1 1 calc R . . C16 C 0.8176(14) 0.1700(6) 0.4495(2) 0.109(2) Uani 1 1 d . . . H16 H 0.7267 0.1376 0.4760 0.131 Uiso 1 1 calc R . . C17 C 0.7636(13) 0.2662(6) 0.4394(2) 0.111(2) Uani 1 1 d . . . H17 H 0.6365 0.3004 0.4594 0.134 Uiso 1 1 calc R . . C18 C 0.8944(10) 0.3135(4) 0.40010(19) 0.0837(15) Uani 1 1 d . . . H18 H 0.8553 0.3796 0.3936 0.100 Uiso 1 1 calc R . . N1 N 0.8835(7) 0.4891(2) 0.30983(12) 0.0552(9) Uani 1 1 d . . . O1 O 0.6965(5) 0.32617(17) 0.18061(9) 0.0475(6) Uani 1 1 d . . . O3 O 0.6440(6) 0.3610(2) 0.05946(11) 0.0653(8) Uani 1 1 d . . . O4 O 0.4710(7) 0.21251(17) 0.07780(10) 0.0647(7) Uani 1 1 d . . . Se1 Se 1.01488(8) 0.31194(2) 0.263961(13) 0.04692(12) Uani 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 C1 0.042(2) 0.0346(17) 0.044(2) 0.0024(18) 0.0099(19) -0.0032(15) C2 0.042(2) 0.0268(16) 0.059(2) 0.0051(17) 0.009(2) -0.0039(15) C3 0.054(2) 0.0396(17) 0.072(2) -0.0002(19) 0.003(4) 0.006(2) C4 0.076(4) 0.0366(19) 0.087(3) -0.007(2) 0.012(3) 0.003(2) C5 0.095(4) 0.046(2) 0.066(3) -0.018(2) 0.003(3) -0.009(3) C6 0.037(2) 0.0345(16) 0.050(2) 0.0067(16) 0.0066(16) -0.0006(17) C7 0.044(2) 0.045(2) 0.062(3) 0.004(2) 0.004(2) 0.0029(18) C8 0.043(2) 0.054(2) 0.060(3) 0.002(2) -0.005(2) -0.0034(19) C9 0.045(2) 0.060(2) 0.0446(19) 0.0065(17) -0.007(2) -0.004(3) C10 0.088(4) 0.086(3) 0.084(4) -0.016(3) 0.018(3) 0.011(3) C11 0.188(8) 0.079(4) 0.191(8) -0.036(4) 0.057(6) 0.020(4) C12 0.044(2) 0.060(2) 0.065(3) 0.001(2) -0.0025(18) 0.003(2) C13 0.042(3) 0.065(2) 0.049(2) -0.003(2) -0.0121(18) 0.0020(19) C14 0.124(4) 0.052(3) 0.065(3) 0.006(2) -0.001(3) 0.004(3) C15 0.152(6) 0.069(3) 0.082(4) 0.012(3) -0.019(5) -0.017(5) C16 0.112(5) 0.146(6) 0.069(4) 0.038(4) -0.013(4) -0.051(5) C17 0.081(4) 0.179(7) 0.074(4) 0.021(5) 0.014(3) 0.026(4) C18 0.090(4) 0.091(3) 0.069(3) 0.019(3) 0.007(3) 0.021(3) N1 0.064(2) 0.0392(16) 0.062(2) -0.0086(16) 0.0018(17) -0.0012(16) O1 0.0490(15) 0.0404(13) 0.0530(16) -0.0023(12) 0.0025(12) 0.0066(13) O3 0.0593(19) 0.0736(18) 0.063(2) 0.0103(15) 0.0075(15) -0.0139(15) O4 0.072(2) 0.0578(16) 0.0643(17) -0.0051(12) 0.0124(17) -0.0010(19) Se1 0.0461(2) 0.04190(17) 0.0527(2) -0.00088(16) 0.0029(2) 0.0038(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 C1 N1 1.330(4) . ? C1 C2 1.403(5) . ? C1 Se1 1.917(3) . ? C2 C3 1.389(4) . ? C2 C6 1.462(5) . ? C3 C4 1.348(6) . ? C4 C5 1.368(6) . ? C5 N1 1.339(5) . ? C6 O1 1.219(3) . ? C6 C7 1.490(5) . ? C7 C8 1.500(5) . ? C8 C9 1.489(6) . ? C9 O3 1.188(4) . ? C9 O4 1.338(4) . ? C10 C11 1.434(5) . ? C10 O4 1.441(5) . ? C12 C13 1.477(5) . ? C12 Se1 1.959(4) . ? C13 C14 1.353(5) . ? C13 C18 1.356(6) . ? C14 C15 1.366(7) . ? C15 C16 1.333(8) . ? C16 C17 1.354(7) . ? C17 C18 1.368(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 N1 C1 C2 124.0(3) . . ? N1 C1 Se1 115.0(3) . . ? C2 C1 Se1 121.0(3) . . ? C3 C2 C1 115.7(4) . . ? C3 C2 C6 121.9(3) . . ? C1 C2 C6 122.3(3) . . ? C4 C3 C2 121.3(5) . . ? C3 C4 C5 118.3(4) . . ? N1 C5 C4 123.8(4) . . ? O1 C6 C2 119.3(3) . . ? O1 C6 C7 119.7(3) . . ? C2 C6 C7 121.1(3) . . ? C6 C7 C8 112.5(3) . . ? C9 C8 C7 113.3(3) . . ? O3 C9 O4 123.7(4) . . ? O3 C9 C8 125.1(4) . . ? O4 C9 C8 111.1(4) . . ? C11 C10 O4 108.5(5) . . ? C13 C12 Se1 113.3(3) . . ? C14 C13 C18 117.9(5) . . ? C14 C13 C12 122.0(4) . . ? C18 C13 C12 120.1(4) . . ? C13 C14 C15 121.2(5) . . ? C16 C15 C14 120.6(5) . . ? C15 C16 C17 119.0(6) . . ? C16 C17 C18 120.6(6) . . ? C13 C18 C17 120.6(5) . . ? C1 N1 C5 116.8(3) . . ? C9 O4 C10 116.4(3) . . ? C1 Se1 C12 99.06(17) . . ? 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 N1 C1 C2 C3 -1.0(5) . . . . ? Se1 C1 C2 C3 178.3(3) . . . . ? N1 C1 C2 C6 -180.0(3) . . . . ? Se1 C1 C2 C6 -0.7(5) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C6 C2 C3 C4 179.2(4) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 N1 -1.3(7) . . . . ? C3 C2 C6 O1 177.6(3) . . . . ? C1 C2 C6 O1 -3.5(5) . . . . ? C3 C2 C6 C7 -1.8(5) . . . . ? C1 C2 C6 C7 177.1(3) . . . . ? O1 C6 C7 C8 17.9(5) . . . . ? C2 C6 C7 C8 -162.7(3) . . . . ? C6 C7 C8 C9 -65.9(4) . . . . ? C7 C8 C9 O3 -40.9(5) . . . . ? C7 C8 C9 O4 141.9(3) . . . . ? Se1 C12 C13 C14 93.7(4) . . . . ? Se1 C12 C13 C18 -88.1(4) . . . . ? C18 C13 C14 C15 2.5(7) . . . . ? C12 C13 C14 C15 -179.2(5) . . . . ? C13 C14 C15 C16 -1.8(9) . . . . ? C14 C15 C16 C17 0.1(10) . . . . ? C15 C16 C17 C18 0.8(10) . . . . ? C14 C13 C18 C17 -1.6(7) . . . . ? C12 C13 C18 C17 -179.9(5) . . . . ? C16 C17 C18 C13 -0.1(9) . . . . ? C2 C1 N1 C5 0.6(5) . . . . ? Se1 C1 N1 C5 -178.7(3) . . . . ? C4 C5 N1 C1 0.6(6) . . . . ? O3 C9 O4 C10 2.4(6) . . . . ? C8 C9 O4 C10 179.7(4) . . . . ? C11 C10 O4 C9 173.8(5) . . . . ? N1 C1 Se1 C12 2.7(3) . . . . ? C2 C1 Se1 C12 -176.6(3) . . . . ? C13 C12 Se1 C1 95.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.552 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.064