# Electronic Supplementary Material (ESI) for Organic & 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_email mugesh@ipc.iisc.ernet.in _publ_contact_author_name 'G. Mugesh' loop_ _publ_author_name 'Govindasamy Mugesh' K.Bhabak 'Kandhan Satheeshkumar' S.Jayavelu data_kpb3se_0m _database_code_depnum_ccdc_archive 'CCDC 800370' #TrackingRef 'kpb3se_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 N4 Se2' _chemical_formula_sum 'C11 H16 N4 Se2' _chemical_formula_weight 362.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 6.9814(2) _cell_length_b 20.5732(6) _cell_length_c 9.8023(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.6430(10) _cell_angle_gamma 90.00 _cell_volume 1355.75(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 26.4 _exptl_crystal_description rectangular _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 5.439 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.3112 _exptl_absorpt_correction_T_max 0.6123 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 11591 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2776 _reflns_number_gt 2207 _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^)+(0.0282P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2776 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.646 _refine_ls_restrained_S_all 1.646 _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 Se1 Se 0.43832(5) 0.732985(18) -0.19754(4) 0.04337(14) Uani 1 1 d . . . Se2 Se 1.12131(5) 0.502181(18) 0.28396(4) 0.04922(15) Uani 1 1 d . . . C1 C 0.6799(5) 0.77093(15) -0.1084(3) 0.0310(7) Uani 1 1 d . . . C7 C 0.8797(5) 0.54093(16) 0.2061(3) 0.0325(7) Uani 1 1 d . . . C4 C 0.9095(5) 0.67785(16) -0.1238(3) 0.0367(8) Uani 1 1 d . . . H4A H 0.9637 0.6778 -0.2051 0.044 Uiso 1 1 calc R . . H4B H 0.7870 0.6530 -0.1485 0.044 Uiso 1 1 calc R . . C6 C 0.9998(5) 0.64637(16) 0.1391(3) 0.0393(8) Uani 1 1 d . . . H6A H 1.1173 0.6371 0.2158 0.047 Uiso 1 1 calc R . . H6B H 0.9555 0.6898 0.1539 0.047 Uiso 1 1 calc R . . C10 C 0.5509(5) 0.87657(18) -0.0388(4) 0.0497(10) Uani 1 1 d . . . H10A H 0.4492 0.8787 -0.1269 0.075 Uiso 1 1 calc R . . H10B H 0.6061 0.9191 -0.0143 0.075 Uiso 1 1 calc R . . H10C H 0.4944 0.8611 0.0343 0.075 Uiso 1 1 calc R . . C9 C 0.6426(5) 0.61123(18) 0.1028(4) 0.0454(9) Uani 1 1 d . . . H9 H 0.5804 0.6486 0.0586 0.055 Uiso 1 1 calc R . . C3 C 1.0059(5) 0.79196(17) -0.0272(3) 0.0372(8) Uani 1 1 d . . . H3 H 1.1432 0.7868 -0.0043 0.045 Uiso 1 1 calc R . . C2 C 0.9090(5) 0.84532(17) -0.0043(4) 0.0382(8) Uani 1 1 d . . . H2 H 0.9659 0.8840 0.0366 0.046 Uiso 1 1 calc R . . C11 C 0.6634(6) 0.45408(18) 0.2582(4) 0.0525(10) Uani 1 1 d . . . H11A H 0.7313 0.4204 0.2219 0.079 Uiso 1 1 calc R . . H11B H 0.5233 0.4451 0.2326 0.079 Uiso 1 1 calc R . . H11C H 0.7127 0.4557 0.3596 0.079 Uiso 1 1 calc R . . C8 C 0.5523(5) 0.55879(19) 0.1347(4) 0.0477(10) Uani 1 1 d . . . H8 H 0.4159 0.5525 0.1167 0.057 Uiso 1 1 calc R . . C5 C 1.0570(5) 0.64530(16) 0.0005(4) 0.0365(8) Uani 1 1 d . . . H5A H 1.0732 0.6004 -0.0245 0.044 Uiso 1 1 calc R . . H5B H 1.1850 0.6665 0.0150 0.044 Uiso 1 1 calc R . . N1 N 0.7084(4) 0.83192(13) -0.0531(3) 0.0340(6) Uani 1 1 d . . . N2 N 0.8650(4) 0.74552(13) -0.0914(3) 0.0314(6) Uani 1 1 d . . . N4 N 0.8446(4) 0.60047(13) 0.1467(3) 0.0331(6) Uani 1 1 d . . . N3 N 0.6980(4) 0.51593(14) 0.1990(3) 0.0370(7) 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 Se1 0.0318(2) 0.0419(2) 0.0499(3) -0.00044(17) -0.00017(17) -0.00298(15) Se2 0.0317(2) 0.0439(3) 0.0696(3) 0.01666(19) 0.0095(2) 0.00405(15) C1 0.0333(18) 0.0333(19) 0.0251(16) 0.0049(14) 0.0057(14) 0.0018(14) C7 0.0341(18) 0.0307(18) 0.0338(18) 0.0045(15) 0.0113(15) 0.0011(14) C4 0.042(2) 0.036(2) 0.0347(19) -0.0020(15) 0.0145(16) 0.0048(15) C6 0.046(2) 0.033(2) 0.036(2) 0.0026(15) 0.0055(16) -0.0054(16) C10 0.047(2) 0.042(2) 0.060(3) -0.0060(19) 0.014(2) 0.0118(17) C9 0.041(2) 0.048(2) 0.048(2) 0.0135(18) 0.0130(18) 0.0161(18) C3 0.0283(18) 0.043(2) 0.039(2) 0.0022(16) 0.0064(16) -0.0061(15) C2 0.037(2) 0.037(2) 0.0372(19) -0.0016(15) 0.0046(16) -0.0070(16) C11 0.045(2) 0.050(2) 0.067(3) 0.014(2) 0.021(2) -0.0096(18) C8 0.0305(19) 0.057(3) 0.055(2) 0.012(2) 0.0118(17) 0.0047(17) C5 0.0297(18) 0.0334(19) 0.047(2) 0.0020(15) 0.0117(16) 0.0025(14) N1 0.0351(15) 0.0307(16) 0.0339(15) -0.0002(12) 0.0052(13) 0.0014(12) N2 0.0302(16) 0.0334(15) 0.0299(15) 0.0020(12) 0.0069(12) 0.0016(12) N4 0.0311(15) 0.0331(16) 0.0353(16) 0.0052(12) 0.0093(12) 0.0009(12) N3 0.0311(16) 0.0377(16) 0.0431(17) 0.0085(13) 0.0118(14) 0.0007(13) _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 C1 1.850(3) . ? Se2 C7 1.835(3) . ? C1 N1 1.360(4) . ? C1 N2 1.362(4) . ? C7 N4 1.350(4) . ? C7 N3 1.353(4) . ? C4 N2 1.479(4) . ? C4 C5 1.522(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 N4 1.454(4) . ? C6 C5 1.516(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C10 N1 1.468(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C9 C8 1.329(5) . ? C9 N4 1.377(4) . ? C9 H9 0.9300 . ? C3 C2 1.340(5) . ? C3 N2 1.394(4) . ? C3 H3 0.9300 . ? C2 N1 1.380(4) . ? C2 H2 0.9300 . ? C11 N3 1.446(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C8 N3 1.365(4) . ? C8 H8 0.9300 . ? C5 H5A 0.9700 . ? C5 H5B 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 N1 C1 N2 105.9(3) . . ? N1 C1 Se1 126.5(2) . . ? N2 C1 Se1 127.6(2) . . ? N4 C7 N3 105.3(3) . . ? N4 C7 Se2 127.8(2) . . ? N3 C7 Se2 126.9(2) . . ? N2 C4 C5 112.2(3) . . ? N2 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N4 C6 C5 114.6(3) . . ? N4 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? N4 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 N4 107.9(3) . . ? C8 C9 H9 126.1 . . ? N4 C9 H9 126.1 . . ? C2 C3 N2 108.1(3) . . ? C2 C3 H3 126.0 . . ? N2 C3 H3 126.0 . . ? C3 C2 N1 106.8(3) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C8 N3 107.0(3) . . ? C9 C8 H8 126.5 . . ? N3 C8 H8 126.5 . . ? C6 C5 C4 115.2(3) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C1 N1 C2 110.4(3) . . ? C1 N1 C10 125.6(3) . . ? C2 N1 C10 123.9(3) . . ? C1 N2 C3 108.8(3) . . ? C1 N2 C4 125.6(3) . . ? C3 N2 C4 125.3(3) . . ? C7 N4 C9 109.4(3) . . ? C7 N4 C6 124.1(3) . . ? C9 N4 C6 126.4(3) . . ? C7 N3 C8 110.5(3) . . ? C7 N3 C11 124.7(3) . . ? C8 N3 C11 124.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.459 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.072 # Attachment 'kpb3s_m.cif' data_kpb3s_m _database_code_depnum_ccdc_archive 'CCDC 800371' #TrackingRef 'kpb3s_m.cif' _Title_of_the_manuscript ; 'Inhibition of Peroxynitrite-Mediated Protein Tyrosine Nitration by some Selones and Thiones: ; _Authors ; Krishna Pada Bhabak, Kandhan Satheeshkumar, Subramaniam Jeyavelu, 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 'C11 H16 N4 S2' _chemical_formula_sum 'C11 H16 N4 S2' _chemical_formula_weight 268.40 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' S S 0.1246 0.1234 '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/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 6.893(2) _cell_length_b 20.222(6) _cell_length_c 9.776(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.617(5) _cell_angle_gamma 90.00 _cell_volume 1305.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3094 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.6 _exptl_crystal_description Rectangular _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9188 _exptl_absorpt_correction_T_max 0.9619 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 11215 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.60 _reflns_number_total 3094 _reflns_number_gt 2354 _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^)+(0.0565P)^2^+0.2541P] 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 3094 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 S1 S 1.05815(7) 0.26417(2) 0.68683(5) 0.04416(16) Uani 1 1 d . . . S2 S 0.39211(7) 0.49614(3) 0.22026(6) 0.04775(17) Uani 1 1 d . . . N2 N 0.6435(2) 0.25349(7) 0.59715(14) 0.0309(3) Uani 1 1 d . . . C1 C 0.8316(3) 0.22827(8) 0.61111(17) 0.0306(4) Uani 1 1 d . . . N1 N 0.7993(2) 0.16671(7) 0.55351(15) 0.0341(3) Uani 1 1 d . . . N3 N 0.6559(2) 0.39962(7) 0.35720(15) 0.0333(3) Uani 1 1 d . . . N4 N 0.8031(2) 0.48503(8) 0.29822(16) 0.0373(4) Uani 1 1 d . . . C8 C 0.6185(3) 0.46003(8) 0.29309(18) 0.0320(4) Uani 1 1 d . . . C7 C 0.4978(3) 0.35313(9) 0.36650(19) 0.0380(4) Uani 1 1 d . . . H7A H 0.5408 0.3087 0.3512 0.046 Uiso 1 1 calc R . . H7B H 0.3760 0.3628 0.2902 0.046 Uiso 1 1 calc R . . C5 C 0.6010(3) 0.32140(9) 0.63146(19) 0.0367(4) Uani 1 1 d . . . H5A H 0.7257 0.3467 0.6557 0.044 Uiso 1 1 calc R . . H5B H 0.5499 0.3211 0.7142 0.044 Uiso 1 1 calc R . . C3 C 0.5950(3) 0.15338(9) 0.50796(19) 0.0388(4) Uani 1 1 d . . . H3 H 0.5355 0.1142 0.4666 0.047 Uiso 1 1 calc R . . C9 C 0.8613(3) 0.38773(10) 0.4000(2) 0.0440(5) Uani 1 1 d . . . H9 H 0.9248 0.3498 0.4452 0.053 Uiso 1 1 calc R . . C2 C 0.4978(3) 0.20689(9) 0.53384(19) 0.0378(4) Uani 1 1 d . . . H2 H 0.3583 0.2120 0.5132 0.045 Uiso 1 1 calc R . . C10 C 0.9524(3) 0.44068(11) 0.3647(2) 0.0461(5) Uani 1 1 d . . . H10 H 1.0911 0.4466 0.3818 0.055 Uiso 1 1 calc R . . C4 C 0.9577(3) 0.12359(10) 0.5339(2) 0.0504(5) Uani 1 1 d . . . H4A H 1.0155 0.1426 0.4644 0.076 Uiso 1 1 calc R . . H4B H 0.9013 0.0811 0.5012 0.076 Uiso 1 1 calc R . . H4C H 1.0611 0.1186 0.6230 0.076 Uiso 1 1 calc R . . C11 C 0.8365(3) 0.54744(10) 0.2348(2) 0.0520(5) Uani 1 1 d . . . H11A H 0.7785 0.5454 0.1332 0.078 Uiso 1 1 calc R . . H11B H 0.9793 0.5557 0.2565 0.078 Uiso 1 1 calc R . . H11C H 0.7737 0.5826 0.2729 0.078 Uiso 1 1 calc R . . C6 C 0.4468(3) 0.35467(9) 0.5074(2) 0.0375(4) Uani 1 1 d . . . H6A H 0.3167 0.3334 0.4943 0.045 Uiso 1 1 calc R . . H6B H 0.4326 0.4004 0.5327 0.045 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 S1 0.0306(3) 0.0415(3) 0.0530(3) 0.0001(2) 0.0001(2) -0.00303(19) S2 0.0308(3) 0.0421(3) 0.0667(4) 0.0151(2) 0.0081(2) 0.00446(19) N2 0.0294(7) 0.0304(7) 0.0328(8) 0.0025(6) 0.0086(6) 0.0012(6) C1 0.0324(9) 0.0315(9) 0.0264(8) 0.0031(6) 0.0062(7) 0.0014(7) N1 0.0342(8) 0.0317(8) 0.0350(8) -0.0006(6) 0.0076(6) 0.0023(6) N3 0.0323(8) 0.0323(8) 0.0352(8) 0.0053(6) 0.0093(6) 0.0013(6) N4 0.0295(8) 0.0397(9) 0.0433(9) 0.0091(7) 0.0111(6) -0.0013(6) C8 0.0324(9) 0.0317(9) 0.0318(9) 0.0028(7) 0.0089(7) -0.0001(7) C7 0.0417(10) 0.0316(9) 0.0369(10) 0.0043(7) 0.0054(8) -0.0059(7) C5 0.0425(10) 0.0341(9) 0.0359(9) -0.0017(7) 0.0151(8) 0.0044(8) C3 0.0377(10) 0.0349(10) 0.0403(10) -0.0003(8) 0.0053(8) -0.0071(8) C9 0.0364(10) 0.0477(11) 0.0465(11) 0.0142(9) 0.0095(8) 0.0105(8) C2 0.0294(9) 0.0400(10) 0.0425(10) 0.0039(8) 0.0078(7) -0.0048(7) C10 0.0293(9) 0.0571(13) 0.0517(12) 0.0126(10) 0.0114(8) 0.0052(9) C4 0.0466(12) 0.0423(11) 0.0611(13) -0.0063(9) 0.0134(10) 0.0099(9) C11 0.0434(11) 0.0477(12) 0.0661(14) 0.0173(10) 0.0177(10) -0.0067(9) C6 0.0312(9) 0.0333(9) 0.0502(11) 0.0059(8) 0.0150(8) 0.0051(7) _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 S1 C1 1.6887(18) . ? S2 C8 1.6854(18) . ? N2 C1 1.364(2) . ? N2 C2 1.387(2) . ? N2 C5 1.463(2) . ? C1 N1 1.358(2) . ? N1 C3 1.377(2) . ? N1 C4 1.453(2) . ? N3 C8 1.364(2) . ? N3 C9 1.378(2) . ? N3 C7 1.461(2) . ? N4 C8 1.357(2) . ? N4 C10 1.380(2) . ? N4 C11 1.453(2) . ? C7 C6 1.516(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 C6 1.522(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C3 C2 1.334(3) . ? C3 H3 0.9300 . ? C9 C10 1.335(3) . ? C9 H9 0.9300 . ? C2 H2 0.9300 . ? C10 H10 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C6 H6A 0.9700 . ? C6 H6B 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 C1 N2 C2 109.68(14) . . ? C1 N2 C5 125.12(14) . . ? C2 N2 C5 124.97(15) . . ? N1 C1 N2 105.22(14) . . ? N1 C1 S1 126.69(13) . . ? N2 C1 S1 128.07(13) . . ? C1 N1 C3 110.19(15) . . ? C1 N1 C4 124.35(15) . . ? C3 N1 C4 125.31(15) . . ? C8 N3 C9 109.79(15) . . ? C8 N3 C7 123.96(14) . . ? C9 N3 C7 126.05(15) . . ? C8 N4 C10 109.89(15) . . ? C8 N4 C11 124.69(15) . . ? C10 N4 C11 125.31(16) . . ? N4 C8 N3 105.37(14) . . ? N4 C8 S2 126.83(13) . . ? N3 C8 S2 127.79(13) . . ? N3 C7 C6 114.46(15) . . ? N3 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? N3 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N2 C5 C6 111.86(15) . . ? N2 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N2 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C2 C3 N1 107.59(16) . . ? C2 C3 H3 126.2 . . ? N1 C3 H3 126.2 . . ? C10 C9 N3 107.46(16) . . ? C10 C9 H9 126.3 . . ? N3 C9 H9 126.3 . . ? C3 C2 N2 107.29(16) . . ? C3 C2 H2 126.4 . . ? N2 C2 H2 126.4 . . ? C9 C10 N4 107.48(16) . . ? C9 C10 H10 126.3 . . ? N4 C10 H10 126.3 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C6 C5 115.09(15) . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.077 # Attachment 'kpb4se_0m.cif' data_kpb4se _database_code_depnum_ccdc_archive 'CCDC 800372' #TrackingRef 'kpb4se_0m.cif' _Title_of_the_manuscript ; 'Inhibition of Peroxynitrite-Mediated Protein Tyrosine Nitration by some Selones and Thiones: ; _Authors ; Krishna Pada Bhabak, Kandhan Satheeshkumar, Subramaniam Jeyavelu, 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 'C12 H18 N4 Se2' _chemical_formula_sum 'C12 H18 N4 Se2' _chemical_formula_weight 376.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.5510(6) _cell_length_b 8.8676(4) _cell_length_c 14.6690(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.566(3) _cell_angle_gamma 90.00 _cell_volume 1432.48(13) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1328 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 25.5 _exptl_crystal_description Rectangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 5.151 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.3368 _exptl_absorpt_correction_T_max 0.5769 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 6011 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.45 _reflns_number_total 1328 _reflns_number_gt 1027 _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^)+(0.0688P)^2^+1.2198P] 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 1328 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.24350(4) 0.15095(5) 0.64148(3) 0.0439(2) Uani 1 1 d . . . N1 N 0.0107(3) 0.2791(4) 0.6290(2) 0.0313(8) Uani 1 1 d . . . N2 N 0.0063(3) 0.0359(4) 0.6251(2) 0.0358(8) Uani 1 1 d . . . C1 C 0.0803(4) 0.1559(4) 0.6313(3) 0.0286(8) Uani 1 1 d . . . C4 C 0.0535(4) 0.4349(5) 0.6326(3) 0.0371(10) Uani 1 1 d . . . H4A H 0.1330 0.4418 0.6797 0.045 Uiso 1 1 calc R . . H4B H -0.0013 0.4994 0.6537 0.045 Uiso 1 1 calc R . . C2 C -0.1089(4) 0.0849(5) 0.6197(3) 0.0454(11) Uani 1 1 d . . . H2 H -0.1759 0.0242 0.6155 0.055 Uiso 1 1 calc R . . C5 C 0.0620(3) 0.4931(4) 0.5377(3) 0.0335(9) Uani 1 1 d . . . H5A H 0.1125 0.4252 0.5143 0.040 Uiso 1 1 calc R . . H5B H 0.1010 0.5912 0.5474 0.040 Uiso 1 1 calc R . . C3 C -0.1067(4) 0.2346(5) 0.6216(3) 0.0413(10) Uani 1 1 d . . . H3 H -0.1720 0.2979 0.6185 0.050 Uiso 1 1 calc R . . C6 C 0.0430(5) -0.1211(5) 0.6244(4) 0.0489(12) Uani 1 1 d . . . H6A H 0.0892 -0.1331 0.5804 0.073 Uiso 1 1 calc R . . H6B H -0.0279 -0.1839 0.6049 0.073 Uiso 1 1 calc R . . H6C H 0.0918 -0.1497 0.6874 0.073 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 0.0251(3) 0.0402(3) 0.0667(4) 0.0068(2) 0.0140(2) 0.00563(17) N1 0.0260(18) 0.0316(18) 0.0354(19) 0.0002(14) 0.0078(14) 0.0040(14) N2 0.0289(18) 0.0327(18) 0.044(2) 0.0070(15) 0.0076(15) -0.0013(14) C1 0.029(2) 0.027(2) 0.030(2) 0.0048(16) 0.0087(17) 0.0025(15) C4 0.035(2) 0.029(2) 0.044(2) -0.0051(18) 0.0059(19) 0.0050(17) C2 0.029(2) 0.051(3) 0.056(3) 0.010(2) 0.012(2) -0.004(2) C5 0.025(2) 0.0243(18) 0.050(3) 0.0009(17) 0.0083(18) 0.0004(15) C3 0.022(2) 0.050(3) 0.052(3) 0.003(2) 0.0116(19) 0.0077(19) C6 0.050(3) 0.033(2) 0.060(3) 0.005(2) 0.011(2) -0.002(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 Se1 C1 1.846(4) . ? N1 C1 1.352(5) . ? N1 C3 1.384(5) . ? N1 C4 1.463(5) . ? N2 C1 1.351(5) . ? N2 C2 1.379(5) . ? N2 C6 1.456(5) . ? C4 C5 1.515(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C2 C3 1.328(7) . ? C2 H2 0.9300 . ? C5 C5 1.527(7) 5_566 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C3 H3 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 N1 C3 109.4(3) . . ? C1 N1 C4 124.8(3) . . ? C3 N1 C4 125.8(3) . . ? C1 N2 C2 109.6(3) . . ? C1 N2 C6 125.0(4) . . ? C2 N2 C6 125.4(4) . . ? N2 C1 N1 106.0(3) . . ? N2 C1 Se1 126.7(3) . . ? N1 C1 Se1 127.4(3) . . ? N1 C4 C5 113.8(3) . . ? N1 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N1 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C3 C2 N2 107.6(4) . . ? C3 C2 H2 126.2 . . ? N2 C2 H2 126.2 . . ? C4 C5 C5 112.7(4) . 5_566 ? C4 C5 H5A 109.0 . . ? C5 C5 H5A 109.0 5_566 . ? C4 C5 H5B 109.0 . . ? C5 C5 H5B 109.0 5_566 . ? H5A C5 H5B 107.8 . . ? C2 C3 N1 107.4(4) . . ? C2 C3 H3 126.3 . . ? N1 C3 H3 126.3 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.866 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.119 # Attachment 'kpb5se.cif' data_kpb5se _database_code_depnum_ccdc_archive 'CCDC 800373' #TrackingRef 'kpb5se.cif' _Title_of_the_manuscript ; 'Inhibition of Peroxynitrite-Mediated Protein Tyrosine Nitration by some Selones and Thiones: ; _Authors ; Krishna Pada Bhabak, Kandhan Satheeshkumar, Subramaniam Jeyavelu, 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 'C13 H20 N4 Se2' _chemical_formula_sum 'C13 H20 N4 Se2' _chemical_formula_weight 390.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 11.7252(9) _cell_length_b 8.7848(7) _cell_length_c 33.465(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3447.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4216 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 28.6 _exptl_crystal_description Rectangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 4.284 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.4139 _exptl_absorpt_correction_T_max 0.6501 _exptl_absorpt_process_details SADABS # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.502 0.069 0.097 26 11 ' ' 2 0.001 0.069 0.403 26 11 ' ' 3 -0.002 -0.069 0.597 26 11 ' ' 4 0.498 -0.069 0.903 26 11 ' ' 5 0.502 0.431 0.597 26 11 ' ' 6 1.002 0.431 0.903 26 11 ' ' 7 -0.002 0.569 0.097 26 11 ' ' 8 0.498 0.569 0.403 26 11 ' ' _platon_squeeze_details ; ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 28285 _diffrn_reflns_av_R_equivalents 0.1570 _diffrn_reflns_av_sigmaI/netI 0.1214 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.65 _reflns_number_total 4216 _reflns_number_gt 1877 _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^)+(0.0655P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4216 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1313 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 0.837 _refine_ls_restrained_S_all 0.837 _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 Se2 Se 0.57068(5) 0.10392(7) 0.563284(16) 0.0616(2) Uani 1 1 d . . . C1 C 0.4195(4) 0.1135(5) 0.54681(14) 0.0432(11) Uani 1 1 d . . . N1 N 0.3304(3) 0.0424(4) 0.56353(10) 0.0434(9) Uani 1 1 d . . . N2 N 0.3785(3) 0.1947(4) 0.51594(10) 0.0452(10) Uani 1 1 d . . . C7 C 0.3119(4) -0.0526(5) 0.67398(13) 0.0499(12) Uani 1 1 d . . . H7A H 0.3828 -0.1091 0.6759 0.060 Uiso 1 1 calc R . . H7B H 0.2503 -0.1259 0.6718 0.060 Uiso 1 1 calc R . . C5 C 0.3332(4) -0.0495(5) 0.59950(14) 0.0532(13) Uani 1 1 d . . . H5A H 0.4065 -0.1002 0.6013 0.064 Uiso 1 1 calc R . . H5B H 0.2747 -0.1274 0.5978 0.064 Uiso 1 1 calc R . . C6 C 0.3145(4) 0.0432(6) 0.63651(13) 0.0483(12) Uani 1 1 d . . . H6A H 0.2429 0.0977 0.6341 0.058 Uiso 1 1 calc R . . H6B H 0.3750 0.1179 0.6388 0.058 Uiso 1 1 calc R . . C8 C 0.2955(4) 0.0396(5) 0.71252(13) 0.0417(11) Uani 1 1 d . . . H8A H 0.3608 0.1061 0.7161 0.050 Uiso 1 1 calc R . . H8B H 0.2284 0.1033 0.7097 0.050 Uiso 1 1 calc R . . C4 C 0.4442(4) 0.2870(6) 0.48845(14) 0.0596(14) Uani 1 1 d . . . H4A H 0.4962 0.3500 0.5032 0.089 Uiso 1 1 calc R . . H4B H 0.3935 0.3502 0.4732 0.089 Uiso 1 1 calc R . . H4C H 0.4863 0.2221 0.4707 0.089 Uiso 1 1 calc R . . C2 C 0.2627(4) 0.1726(6) 0.51356(15) 0.0549(13) Uani 1 1 d . . . H2 H 0.2145 0.2142 0.4944 0.066 Uiso 1 1 calc R . . C3 C 0.2313(4) 0.0817(6) 0.54335(14) 0.0526(13) Uani 1 1 d . . . H3 H 0.1575 0.0507 0.5495 0.063 Uiso 1 1 calc R . . C10 C 0.2823(4) -0.0576(5) 0.74907(12) 0.0485(13) Uani 1 1 d . . . H10A H 0.2233 -0.1328 0.7442 0.058 Uiso 1 1 calc R . . H10B H 0.3531 -0.1114 0.7540 0.058 Uiso 1 1 calc R . . Se1 Se 0.48400(4) 0.07277(8) 0.809657(17) 0.0728(2) Uani 1 1 d . . . C12 C 0.3273(4) 0.0924(5) 0.81031(13) 0.0407(11) Uani 1 1 d . . . N4 N 0.2648(3) 0.1707(4) 0.83646(11) 0.0494(10) Uani 1 1 d . . . C11 C 0.1440(4) 0.0735(6) 0.79432(15) 0.0559(14) Uani 1 1 d . . . H11 H 0.0772 0.0475 0.7810 0.067 Uiso 1 1 calc R . . N3 N 0.2529(3) 0.0292(4) 0.78403(10) 0.0425(9) Uani 1 1 d . . . C13 C 0.1523(4) 0.1610(7) 0.82696(15) 0.0613(15) Uani 1 1 d . . . H13 H 0.0923 0.2067 0.8406 0.074 Uiso 1 1 calc R . . C14 C 0.3096(5) 0.2599(7) 0.86981(15) 0.0739(17) Uani 1 1 d . . . H14A H 0.3619 0.1988 0.8850 0.111 Uiso 1 1 calc R . . H14B H 0.2478 0.2915 0.8867 0.111 Uiso 1 1 calc R . . H14C H 0.3485 0.3480 0.8597 0.111 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 Se2 0.0448(3) 0.0823(4) 0.0577(4) 0.0031(3) -0.0073(2) 0.0007(3) C1 0.046(3) 0.048(3) 0.035(3) -0.008(2) -0.002(2) -0.004(2) N1 0.047(2) 0.056(2) 0.027(2) 0.0015(19) 0.0018(18) -0.0049(19) N2 0.043(2) 0.059(3) 0.033(2) 0.0087(19) 0.0027(18) -0.003(2) C7 0.056(3) 0.051(3) 0.043(3) 0.001(2) -0.003(2) 0.003(2) C5 0.061(3) 0.052(3) 0.046(3) 0.001(3) 0.005(2) -0.002(3) C6 0.047(3) 0.057(3) 0.041(3) 0.001(2) 0.000(2) 0.000(2) C8 0.038(3) 0.044(3) 0.043(3) -0.002(2) 0.000(2) 0.005(2) C4 0.064(3) 0.064(4) 0.051(3) 0.014(3) 0.008(3) -0.006(3) C2 0.041(3) 0.072(4) 0.052(3) -0.001(3) -0.008(2) 0.003(3) C3 0.047(3) 0.067(3) 0.044(3) -0.001(3) -0.001(2) -0.008(3) C10 0.063(3) 0.051(3) 0.032(3) -0.002(2) -0.004(2) 0.004(2) Se1 0.0398(3) 0.1093(6) 0.0692(4) -0.0088(4) 0.0063(3) -0.0136(3) C12 0.049(3) 0.045(3) 0.029(2) -0.003(2) 0.007(2) -0.007(2) N4 0.052(3) 0.060(3) 0.036(2) -0.005(2) 0.003(2) -0.009(2) C11 0.039(3) 0.078(4) 0.050(3) 0.008(3) 0.001(2) -0.002(3) N3 0.042(2) 0.052(2) 0.034(2) 0.0028(19) 0.0034(19) -0.0041(19) C13 0.049(3) 0.092(4) 0.043(3) 0.007(3) 0.012(3) 0.009(3) C14 0.079(4) 0.081(4) 0.061(4) -0.022(3) 0.009(3) -0.012(3) _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 Se2 C1 1.858(5) . ? C1 N1 1.340(6) . ? C1 N2 1.344(5) . ? N1 C3 1.387(6) . ? N1 C5 1.450(5) . ? N2 C2 1.374(6) . ? N2 C4 1.448(6) . ? C7 C6 1.510(6) . ? C7 C8 1.535(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 C6 1.498(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C10 1.500(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C2 C3 1.329(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C10 N3 1.438(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Se1 C12 1.846(5) . ? C12 N4 1.332(5) . ? C12 N3 1.357(5) . ? N4 C13 1.359(6) . ? N4 C14 1.462(6) . ? C11 C13 1.339(6) . ? C11 N3 1.378(6) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 N2 106.8(4) . . ? N1 C1 Se2 126.8(4) . . ? N2 C1 Se2 126.4(4) . . ? C1 N1 C3 109.5(4) . . ? C1 N1 C5 126.0(4) . . ? C3 N1 C5 124.2(4) . . ? C1 N2 C2 108.8(4) . . ? C1 N2 C4 126.5(4) . . ? C2 N2 C4 124.6(4) . . ? C6 C7 C8 114.0(4) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N1 C5 C6 112.3(4) . . ? N1 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N1 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 112.7(4) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C10 C8 C7 113.4(4) . . ? C10 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C10 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C2 N2 108.4(4) . . ? C3 C2 H2 125.8 . . ? N2 C2 H2 125.8 . . ? C2 C3 N1 106.4(4) . . ? C2 C3 H3 126.8 . . ? N1 C3 H3 126.8 . . ? N3 C10 C8 112.8(4) . . ? N3 C10 H10A 109.0 . . ? C8 C10 H10A 109.0 . . ? N3 C10 H10B 109.0 . . ? C8 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N4 C12 N3 106.5(4) . . ? N4 C12 Se1 127.1(3) . . ? N3 C12 Se1 126.4(3) . . ? C12 N4 C13 110.4(4) . . ? C12 N4 C14 125.5(4) . . ? C13 N4 C14 124.1(4) . . ? C13 C11 N3 107.4(4) . . ? C13 C11 H11 126.3 . . ? N3 C11 H11 126.3 . . ? C12 N3 C11 108.5(4) . . ? C12 N3 C10 126.2(4) . . ? C11 N3 C10 125.1(4) . . ? C11 C13 N4 107.3(4) . . ? C11 C13 H13 126.4 . . ? N4 C13 H13 126.4 . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.703 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.140