# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mugesh, Govindasamy' _publ_contact_author_email mugesh@ipc.iisc.ernet.in loop_ _publ_author_name K.P.Bhabak G.P.Roy G.Mugesh data_compound20_ _database_code_depnum_ccdc_archive 'CCDC 765980' #TrackingRef 'Compound-20.cif' _Title_of_the_manuscript ; 'Mechanistic Investigations on the Efficient Catalytic Decomposition of Peroxynitrite by Ebselen Analogues' ; _Authors ; Krishna Pada Bhabak, Amit Ashok Vernekar, Surendar Reddy Jakka, Gouriprasanna Roy and Govindasamy Mugesh* ; _Journal_submitted ; Organic & Biomolecular Chemistry ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O4 Se' _chemical_formula_sum 'C16 H20 N2 O4 Se' _chemical_formula_weight 383.30 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9670(14) _cell_length_b 10.517(2) _cell_length_c 11.826(2) _cell_angle_alpha 87.388(3) _cell_angle_beta 73.485(3) _cell_angle_gamma 85.092(3) _cell_volume 827.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8636 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 26.01 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 2.290 _exptl_absorpt_correction_type ANALYTICAL _exptl_absorpt_correction_T_min 0.5466 _exptl_absorpt_correction_T_max 0.7251 _exptl_absorpt_process_details empirical _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 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8636 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3235 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0674P)^2^+0.4063P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3235 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _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 Se1 Se 0.66694(5) 0.22622(3) 0.54212(3) 0.03905(14) Uani 1 1 d . . . O1 O 0.9418(4) 0.3919(3) 0.2376(2) 0.0563(7) Uani 1 1 d . . . O2 O 0.4629(5) 0.4949(3) 0.8525(3) 0.0715(8) Uani 1 1 d . . . O3 O 1.1807(5) 0.0889(3) 0.3225(3) 0.0816(9) Uani 1 1 d . . . H3 H 1.1460 0.0267 0.3655 0.122 Uiso 1 1 calc R . . O4 O 0.8415(4) 0.1644(2) 0.6007(2) 0.0555(6) Uani 1 1 d . . . N1 N 0.7981(4) 0.2428(2) 0.3784(2) 0.0393(6) Uani 1 1 d . . . N2 N 0.4455(5) 0.3145(3) 0.7620(3) 0.0551(8) Uani 1 1 d . . . C1 C 0.6911(4) 0.4073(3) 0.5440(3) 0.0377(7) Uani 1 1 d . . . C2 C 0.7931(4) 0.4553(3) 0.4369(3) 0.0389(7) Uani 1 1 d . . . C3 C 0.8353(5) 0.5834(3) 0.4243(4) 0.0501(9) Uani 1 1 d . . . H3A H 0.9013 0.6179 0.3512 0.060 Uiso 1 1 calc R . . C4 C 0.7760(5) 0.6579(3) 0.5240(4) 0.0534(9) Uani 1 1 d . . . H4 H 0.8062 0.7428 0.5178 0.064 Uiso 1 1 calc R . . C5 C 0.6733(5) 0.6084(3) 0.6318(4) 0.0525(9) Uani 1 1 d . . . H5 H 0.6347 0.6607 0.6970 0.063 Uiso 1 1 calc R . . C6 C 0.6261(5) 0.4815(3) 0.6453(3) 0.0452(8) Uani 1 1 d . . . C7 C 0.5086(5) 0.4240(4) 0.7545(3) 0.0491(8) Uani 1 1 d . . . C8 C 0.3200(9) 0.4232(6) 0.9399(4) 0.0980(19) Uani 1 1 d . . . H8A H 0.1846 0.4622 0.9518 0.118 Uiso 1 1 calc R . . H8B H 0.3520 0.4188 1.0147 0.118 Uiso 1 1 calc R . . C9 C 0.3404(7) 0.2895(5) 0.8882(4) 0.0682(12) Uani 1 1 d . . . C10 C 0.1356(9) 0.2459(7) 0.9013(4) 0.099(2) Uani 1 1 d . . . H10A H 0.1484 0.1624 0.8693 0.149 Uiso 1 1 calc R . . H10B H 0.0650 0.3045 0.8597 0.149 Uiso 1 1 calc R . . H10C H 0.0623 0.2431 0.9834 0.149 Uiso 1 1 calc R . . C11 C 0.4725(12) 0.1924(9) 0.9375(6) 0.149(4) Uani 1 1 d . . . H11A H 0.6014 0.2246 0.9270 0.224 Uiso 1 1 calc R . . H11B H 0.4890 0.1137 0.8966 0.224 Uiso 1 1 calc R . . H11C H 0.4102 0.1777 1.0201 0.224 Uiso 1 1 calc R . . C12 C 0.8549(5) 0.3628(3) 0.3388(3) 0.0418(7) Uani 1 1 d . . . C13 C 0.8399(5) 0.1308(3) 0.2987(3) 0.0439(7) Uani 1 1 d . . . C14 C 0.7390(6) 0.1580(4) 0.2006(3) 0.0587(10) Uani 1 1 d . . . H14A H 0.7916 0.2317 0.1552 0.088 Uiso 1 1 calc R . . H14B H 0.5968 0.1737 0.2345 0.088 Uiso 1 1 calc R . . H14C H 0.7651 0.0857 0.1503 0.088 Uiso 1 1 calc R . . C15 C 0.7554(6) 0.0133(4) 0.3709(4) 0.0570(10) Uani 1 1 d . . . H15A H 0.8189 -0.0041 0.4328 0.085 Uiso 1 1 calc R . . H15B H 0.7811 -0.0589 0.3205 0.085 Uiso 1 1 calc R . . H15C H 0.6133 0.0293 0.4048 0.085 Uiso 1 1 calc R . . C16 C 1.0682(6) 0.1064(4) 0.2461(4) 0.0563(9) Uani 1 1 d . . . H16A H 1.0928 0.0314 0.1977 0.068 Uiso 1 1 calc R . . H16B H 1.1157 0.1780 0.1941 0.068 Uiso 1 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 Se1 0.0406(2) 0.0354(2) 0.0385(2) 0.00412(13) -0.00654(14) -0.00666(13) O1 0.0582(16) 0.0582(16) 0.0477(15) 0.0186(12) -0.0082(12) -0.0119(12) O2 0.0701(19) 0.090(2) 0.0546(17) -0.0282(15) -0.0108(14) -0.0156(16) O3 0.073(2) 0.072(2) 0.099(3) 0.0035(18) -0.0237(19) -0.0059(16) O4 0.0637(16) 0.0495(14) 0.0510(15) 0.0090(11) -0.0186(13) 0.0110(12) N1 0.0381(14) 0.0358(14) 0.0400(14) 0.0060(11) -0.0051(11) -0.0038(11) N2 0.060(2) 0.058(2) 0.0410(16) -0.0043(14) -0.0038(14) -0.0053(15) C1 0.0318(15) 0.0341(16) 0.0501(18) 0.0013(13) -0.0169(13) -0.0010(12) C2 0.0308(15) 0.0370(16) 0.0528(19) 0.0087(14) -0.0191(14) -0.0038(12) C3 0.0376(17) 0.0430(19) 0.077(3) 0.0155(17) -0.0284(17) -0.0069(14) C4 0.0444(19) 0.0359(18) 0.089(3) -0.0012(18) -0.033(2) -0.0032(14) C5 0.0405(18) 0.047(2) 0.077(3) -0.0126(18) -0.0280(18) 0.0044(15) C6 0.0320(16) 0.0461(19) 0.062(2) -0.0097(16) -0.0209(15) 0.0043(13) C7 0.0423(18) 0.058(2) 0.052(2) -0.0142(17) -0.0196(16) 0.0020(16) C8 0.094(4) 0.142(5) 0.055(3) -0.037(3) -0.005(3) -0.029(4) C9 0.070(3) 0.087(3) 0.041(2) -0.004(2) -0.0049(19) -0.009(2) C10 0.096(4) 0.137(5) 0.053(3) -0.013(3) 0.010(3) -0.048(4) C11 0.120(6) 0.207(9) 0.084(4) 0.064(5) 0.007(4) 0.040(6) C12 0.0330(16) 0.0454(18) 0.0467(19) 0.0111(14) -0.0120(14) -0.0057(13) C13 0.0445(18) 0.0435(18) 0.0390(17) -0.0005(14) -0.0043(14) -0.0026(14) C14 0.064(2) 0.060(2) 0.053(2) -0.0063(18) -0.0187(19) 0.0029(19) C15 0.064(2) 0.044(2) 0.054(2) -0.0057(16) 0.0011(18) -0.0126(17) C16 0.046(2) 0.059(2) 0.055(2) 0.0049(18) -0.0033(17) 0.0027(17) _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 Se1 O4 1.638(2) . ? Se1 N1 1.899(3) . ? Se1 C1 1.928(3) . ? O1 C12 1.215(4) . ? O2 C7 1.353(4) . ? O2 C8 1.449(6) . ? O3 C16 1.352(5) . ? O3 H3 0.8200 . ? N1 C12 1.377(4) . ? N1 C13 1.499(4) . ? N2 C7 1.258(5) . ? N2 C9 1.485(5) . ? C1 C2 1.362(5) . ? C1 C6 1.401(5) . ? C2 C3 1.396(5) . ? C2 C12 1.491(5) . ? C3 C4 1.388(6) . ? C3 H3A 0.9300 . ? C4 C5 1.376(6) . ? C4 H4 0.9300 . ? C5 C6 1.394(5) . ? C5 H5 0.9300 . ? C6 C7 1.455(5) . ? C8 C9 1.538(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.500(7) . ? C9 C11 1.523(8) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C13 C14 1.523(5) . ? C13 C15 1.532(5) . ? C13 C16 1.537(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 O4 Se1 N1 104.95(13) . . ? O4 Se1 C1 103.33(13) . . ? N1 Se1 C1 84.68(13) . . ? C7 O2 C8 104.3(3) . . ? C16 O3 H3 109.5 . . ? C12 N1 C13 122.6(3) . . ? C12 N1 Se1 115.8(2) . . ? C13 N1 Se1 121.5(2) . . ? C7 N2 C9 107.3(3) . . ? C2 C1 C6 122.6(3) . . ? C2 C1 Se1 112.6(2) . . ? C6 C1 Se1 124.6(3) . . ? C1 C2 C3 120.1(3) . . ? C1 C2 C12 115.8(3) . . ? C3 C2 C12 124.0(3) . . ? C4 C3 C2 118.2(4) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.3(4) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 116.5(3) . . ? C5 C6 C7 124.6(3) . . ? C1 C6 C7 118.8(3) . . ? N2 C7 O2 118.9(4) . . ? N2 C7 C6 124.0(3) . . ? O2 C7 C6 117.1(3) . . ? O2 C8 C9 104.7(4) . . ? O2 C8 H8A 110.8 . . ? C9 C8 H8A 110.8 . . ? O2 C8 H8B 110.8 . . ? C9 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? N2 C9 C10 110.7(4) . . ? N2 C9 C11 108.0(4) . . ? C10 C9 C11 112.7(6) . . ? N2 C9 C8 101.7(4) . . ? C10 C9 C8 109.5(4) . . ? C11 C9 C8 113.7(6) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 N1 125.5(3) . . ? O1 C12 C2 123.6(3) . . ? N1 C12 C2 110.9(3) . . ? N1 C13 C14 109.8(3) . . ? N1 C13 C15 108.9(3) . . ? C14 C13 C15 109.3(3) . . ? N1 C13 C16 109.0(3) . . ? C14 C13 C16 110.2(3) . . ? C15 C13 C16 109.6(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 C13 117.3(3) . . ? O3 C16 H16A 108.0 . . ? C13 C16 H16A 108.0 . . ? O3 C16 H16B 108.0 . . ? C13 C16 H16B 108.0 . . ? H16A C16 H16B 107.2 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.361 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.085