# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jain, Vimal K.' _publ_contact_author_email jainvk@barc.gov.in _publ_section_title ; Synthesis, characterization and structures of 2-(3,5-dimethylpyrazol-1-yl)ethylseleno derivatives and their probable glutathione peroxidase (GPx) like activity ; loop_ _publ_author_name 'Ananda S. Hodage' 'Prasad P. Phadnis' 'Amey Wadwale' 'K. I. Priyadarsini' V.K.Jain # Attachment 'CIF-file-dmpzCH2CH2SeCH2COOH.cif' data_AH-06 _database_code_depnum_ccdc_archive 'CCDC 784803' #TrackingRef 'CIF-file-dmpzCH2CH2SeCH2COOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 N2 O2 Se' _chemical_formula_sum 'C9 H14 N2 O2 Se' _chemical_formula_weight 261.18 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 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 8.370(3) _cell_length_b 11.000(4) _cell_length_c 12.192(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1122.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 8.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 3.324 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.5561 _exptl_absorpt_correction_T_max 0.8514 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 1.74 _diffrn_reflns_number 1950 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1343 _reflns_number_gt 788 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ortep 3 for windows' _computing_publication_material 'WinGX 1.70.01' _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^)+(0.0531P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 1343 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.983 _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 0.55362(9) 0.11992(7) 0.70268(14) 0.0514(3) Uani 1 1 d . . . C2 C 0.6720(8) -0.1236(5) 0.7129(14) 0.0393(18) Uani 1 1 d . . . H2A H 0.7026 -0.1104 0.6371 0.047 Uiso 1 1 calc R . . H2B H 0.7586 -0.0948 0.7589 0.047 Uiso 1 1 calc R . . C5 C 0.5898(9) -0.4380(7) 0.6947(14) 0.043(2) Uani 1 1 d . . . N1 N 0.6509(7) -0.2545(6) 0.7312(5) 0.0434(18) Uani 1 1 d . . . C4 C 0.6255(10) -0.4341(9) 0.8046(7) 0.045(2) Uani 1 1 d . . . H4 H 0.6246 -0.4990 0.8535 0.054 Uiso 1 1 calc R . . N2 N 0.6029(9) -0.3275(8) 0.6479(6) 0.0453(18) Uani 1 1 d . . . C1 C 0.5277(9) -0.0516(7) 0.7367(7) 0.045(2) Uani 1 1 d . . . H1A H 0.5011 -0.0602 0.8137 0.053 Uiso 1 1 calc R . . H1B H 0.4391 -0.0838 0.6943 0.053 Uiso 1 1 calc R . . C3 C 0.6627(9) -0.3156(8) 0.8279(7) 0.042(2) Uani 1 1 d . . . C7 C 0.5489(12) -0.5453(8) 0.6237(9) 0.065(3) Uani 1 1 d . . . H7A H 0.5033 -0.5173 0.5561 0.098 Uiso 1 1 calc R . . H7B H 0.4733 -0.5961 0.6612 0.098 Uiso 1 1 calc R . . H7C H 0.6441 -0.5910 0.6086 0.098 Uiso 1 1 calc R . . C6 C 0.7178(11) -0.2528(8) 0.9302(8) 0.064(3) Uani 1 1 d . . . H6A H 0.8232 -0.2207 0.9189 0.097 Uiso 1 1 calc R . . H6B H 0.7197 -0.3099 0.9897 0.097 Uiso 1 1 calc R . . H6C H 0.6458 -0.1876 0.9474 0.097 Uiso 1 1 calc R . . C9 C 0.5916(11) 0.1695(9) 0.9307(8) 0.053(2) Uani 1 1 d . . . C8 C 0.6866(10) 0.1642(8) 0.8284(8) 0.054(2) Uani 1 1 d . . . H8A H 0.7716 0.1049 0.8367 0.065 Uiso 1 1 calc R . . H8B H 0.7354 0.2429 0.8152 0.065 Uiso 1 1 calc R . . O2 O 0.5478(8) 0.2817(5) 0.9572(5) 0.0632(18) Uani 1 1 d . . . H2 H 0.4984 0.2804 1.0153 0.095 Uiso 1 1 calc R . . O1 O 0.5559(10) 0.0798(7) 0.9821(6) 0.083(3) 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 0.0732(6) 0.0410(4) 0.0400(4) 0.0032(8) 0.0048(8) 0.0039(5) C2 0.046(4) 0.033(3) 0.040(5) -0.004(5) 0.010(6) -0.005(3) C5 0.037(4) 0.033(4) 0.059(7) 0.003(6) 0.002(6) 0.005(3) N1 0.043(4) 0.036(3) 0.051(5) -0.006(3) 0.008(3) 0.006(4) C4 0.043(5) 0.048(5) 0.045(5) 0.006(4) 0.010(4) 0.005(5) N2 0.046(4) 0.051(5) 0.039(4) -0.002(4) -0.003(4) 0.006(4) C1 0.044(4) 0.047(5) 0.043(5) -0.002(4) 0.008(4) -0.006(4) C3 0.041(5) 0.047(6) 0.038(5) 0.000(4) 0.006(4) 0.003(5) C7 0.079(7) 0.041(5) 0.076(7) -0.016(5) 0.009(6) 0.001(5) C6 0.078(7) 0.075(6) 0.040(4) 0.010(5) -0.010(5) -0.010(5) C9 0.069(7) 0.051(5) 0.039(5) -0.006(5) 0.001(5) -0.007(5) C8 0.059(6) 0.042(5) 0.060(6) -0.011(5) 0.005(5) -0.004(5) O2 0.097(5) 0.044(4) 0.049(4) -0.002(3) 0.019(4) 0.002(4) O1 0.155(9) 0.044(3) 0.051(4) -0.005(3) 0.024(5) -0.010(5) _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 1.944(8) . ? Se1 C8 1.956(9) . ? C2 N1 1.468(8) . ? C2 C1 1.473(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C5 N2 1.347(12) . ? C5 C4 1.373(18) . ? C5 C7 1.503(15) . ? N1 N2 1.356(9) . ? N1 C3 1.361(10) . ? C4 C3 1.370(13) . ? C4 H4 0.9300 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C6 1.498(12) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C9 O1 1.206(12) . ? C9 O2 1.328(11) . ? C9 C8 1.480(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O2 H2 0.8200 . ? 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 Se1 C8 98.0(4) . . ? N1 C2 C1 113.5(6) . . ? N1 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N2 C5 C4 111.6(10) . . ? N2 C5 C7 118.9(13) . . ? C4 C5 C7 129.5(10) . . ? N2 N1 C3 112.2(7) . . ? N2 N1 C2 120.2(9) . . ? C3 N1 C2 127.4(9) . . ? C3 C4 C5 106.4(9) . . ? C3 C4 H4 126.8 . . ? C5 C4 H4 126.8 . . ? C5 N2 N1 103.9(9) . . ? C2 C1 Se1 112.9(5) . . ? C2 C1 H1A 109.0 . . ? Se1 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? Se1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N1 C3 C4 105.9(7) . . ? N1 C3 C6 121.0(8) . . ? C4 C3 C6 133.0(8) . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O1 C9 O2 124.4(9) . . ? O1 C9 C8 122.7(9) . . ? O2 C9 C8 112.9(9) . . ? C9 C8 Se1 111.3(6) . . ? C9 C8 H8A 109.4 . . ? Se1 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? Se1 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C9 O2 H2 109.5 . . ? 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 C1 C2 N1 N2 91.6(13) . . . . ? C1 C2 N1 C3 -83.1(13) . . . . ? N2 C5 C4 C3 0.1(10) . . . . ? C7 C5 C4 C3 176.6(8) . . . . ? C4 C5 N2 N1 1.1(9) . . . . ? C7 C5 N2 N1 -175.8(7) . . . . ? C3 N1 N2 C5 -1.9(9) . . . . ? C2 N1 N2 C5 -177.4(6) . . . . ? N1 C2 C1 Se1 -176.2(8) . . . . ? C8 Se1 C1 C2 -75.2(9) . . . . ? N2 N1 C3 C4 2.0(9) . . . . ? C2 N1 C3 C4 177.0(7) . . . . ? N2 N1 C3 C6 178.5(7) . . . . ? C2 N1 C3 C6 -6.5(12) . . . . ? C5 C4 C3 N1 -1.2(9) . . . . ? C5 C4 C3 C6 -177.1(9) . . . . ? O1 C9 C8 Se1 80.2(11) . . . . ? O2 C9 C8 Se1 -98.3(8) . . . . ? C1 Se1 C8 C9 -74.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.447 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.086 # Attachment 'CIF-file-dmpzCH2CH2SeCH2CH2COOH.cif' data_AH-07 _database_code_depnum_ccdc_archive 'CCDC 784804' #TrackingRef 'CIF-file-dmpzCH2CH2SeCH2CH2COOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O2 Se' _chemical_formula_weight 275.21 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' 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' 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 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 13.200(5) _cell_length_b 11.169(5) _cell_length_c 7.993(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.12(4) _cell_angle_gamma 90.00 _cell_volume 1177.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 10.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 3.172 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.5695 _exptl_absorpt_correction_T_max 0.7421 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.23 _diffrn_reflns_number 3241 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2708 _reflns_number_gt 1595 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution 'SIR 2004' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep 3 for windows' _computing_publication_material 'WinGX 1.80.01' _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^)+(0.0249P)^2^+1.4004P] 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 SHELXL _refine_ls_extinction_coef 0.0026(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2708 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.03797(3) 0.85299(4) 0.11515(6) 0.04673(17) Uani 1 1 d . . . O1 O 0.1407(3) 0.4479(3) 0.1374(5) 0.0732(11) Uani 1 1 d . . . O2 O 0.2768(2) 0.4969(3) 0.0002(5) 0.0628(10) Uani 1 1 d . . . H2 H 0.2852 0.4241 -0.0003 0.094 Uiso 1 1 calc R . . N1 N -0.2796(2) 0.8407(3) 0.0357(4) 0.0380(8) Uani 1 1 d . . . N2 N -0.3285(2) 0.7342(3) 0.0472(4) 0.0378(8) Uani 1 1 d . . . C6 C -0.3042(3) 1.0603(4) 0.0728(7) 0.0595(13) Uani 1 1 d . . . H6A H -0.2464 1.0705 0.1479 0.089 Uiso 1 1 calc R . . H6B H -0.3579 1.1123 0.1058 0.089 Uiso 1 1 calc R . . H6C H -0.2859 1.0796 -0.0391 0.089 Uiso 1 1 calc R . . C8 C 0.0609(3) 0.6803(4) 0.1197(6) 0.0496(12) Uani 1 1 d . . . H8A H 0.0509 0.6498 0.2315 0.060 Uiso 1 1 calc R . . H8B H 0.0128 0.6410 0.0432 0.060 Uiso 1 1 calc R . . C4 C -0.4301(3) 0.8844(4) 0.1180(6) 0.0433(10) Uani 1 1 d . . . H4 H -0.4871 0.9253 0.1523 0.052 Uiso 1 1 calc R . . C3 C -0.3392(3) 0.9338(4) 0.0788(5) 0.0396(10) Uani 1 1 d . . . C5 C -0.4212(3) 0.7616(4) 0.0968(5) 0.0369(9) Uani 1 1 d . . . C9 C 0.1678(3) 0.6540(4) 0.0689(6) 0.0456(10) Uani 1 1 d . . . H9A H 0.1768 0.6843 -0.0434 0.055 Uiso 1 1 calc R . . H9B H 0.2152 0.6957 0.1440 0.055 Uiso 1 1 calc R . . C2 C -0.1721(3) 0.8432(4) -0.0012(5) 0.0398(9) Uani 1 1 d . . . H2A H -0.1588 0.9115 -0.0720 0.048 Uiso 1 1 calc R . . H2B H -0.1551 0.7713 -0.0622 0.048 Uiso 1 1 calc R . . C1 C -0.1063(3) 0.8509(4) 0.1559(5) 0.0456(10) Uani 1 1 d . . . H1A H -0.1208 0.7831 0.2269 0.055 Uiso 1 1 calc R . . H1B H -0.1236 0.9231 0.2160 0.055 Uiso 1 1 calc R . . C10 C 0.1916(3) 0.5222(4) 0.0727(6) 0.0433(10) Uani 1 1 d . . . C7 C -0.4984(3) 0.6652(4) 0.1163(6) 0.0523(12) Uani 1 1 d . . . H7A H -0.4848 0.6005 0.0414 0.078 Uiso 1 1 calc R . . H7B H -0.5648 0.6968 0.0904 0.078 Uiso 1 1 calc R . . H7C H -0.4953 0.6365 0.2295 0.078 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 0.0340(2) 0.0354(2) 0.0709(3) -0.0010(3) 0.00317(18) 0.0018(2) O1 0.071(2) 0.0385(17) 0.113(3) 0.004(2) 0.048(2) -0.0012(17) O2 0.0512(19) 0.0359(16) 0.104(3) 0.0097(18) 0.0321(18) 0.0111(15) N1 0.0304(16) 0.0315(17) 0.053(2) -0.0025(17) 0.0070(14) 0.0008(14) N2 0.0337(18) 0.0301(16) 0.050(2) -0.0020(16) 0.0052(15) -0.0005(14) C6 0.051(3) 0.032(2) 0.095(4) -0.006(3) -0.005(3) 0.006(2) C8 0.046(3) 0.032(2) 0.071(3) -0.001(2) 0.010(2) 0.0055(18) C4 0.033(2) 0.044(2) 0.054(3) -0.005(2) 0.0067(19) 0.0089(17) C3 0.038(2) 0.034(2) 0.047(3) -0.0045(19) 0.0002(19) 0.0037(18) C5 0.034(2) 0.039(2) 0.038(2) 0.0011(19) 0.0040(18) 0.0001(17) C9 0.044(2) 0.036(2) 0.058(3) -0.001(2) 0.008(2) 0.001(2) C2 0.034(2) 0.037(2) 0.049(2) -0.001(2) 0.0108(18) 0.0041(18) C1 0.036(2) 0.049(2) 0.052(3) -0.002(2) 0.0103(18) 0.002(2) C10 0.039(2) 0.037(2) 0.054(3) -0.003(2) 0.006(2) -0.0004(19) C7 0.043(2) 0.054(3) 0.061(3) 0.005(2) 0.008(2) -0.007(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 1.944(4) . ? Se1 C8 1.952(4) . ? O1 C10 1.197(5) . ? O2 C10 1.315(5) . ? O2 H2 0.8200 . ? N1 C3 1.356(5) . ? N1 N2 1.358(4) . ? N1 C2 1.461(4) . ? N2 C5 1.336(5) . ? C6 C3 1.487(6) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C8 C9 1.512(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 C3 1.368(5) . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C7 1.495(5) . ? C9 C10 1.506(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C2 C1 1.503(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 Se1 C8 97.90(18) . . ? C10 O2 H2 109.5 . . ? C3 N1 N2 111.9(3) . . ? C3 N1 C2 127.9(3) . . ? N2 N1 C2 119.8(3) . . ? C5 N2 N1 105.2(3) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C8 Se1 109.4(3) . . ? C9 C8 H8A 109.8 . . ? Se1 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? Se1 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C3 C4 C5 107.0(4) . . ? C3 C4 H4 126.5 . . ? C5 C4 H4 126.5 . . ? N1 C3 C4 105.7(3) . . ? N1 C3 C6 122.5(4) . . ? C4 C3 C6 131.8(4) . . ? N2 C5 C4 110.2(4) . . ? N2 C5 C7 120.1(4) . . ? C4 C5 C7 129.6(4) . . ? C10 C9 C8 112.4(3) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? N1 C2 C1 111.6(3) . . ? N1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C1 Se1 113.6(3) . . ? C2 C1 H1A 108.8 . . ? Se1 C1 H1A 108.8 . . ? C2 C1 H1B 108.8 . . ? Se1 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? O1 C10 O2 123.0(4) . . ? O1 C10 C9 124.5(4) . . ? O2 C10 C9 112.5(4) . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 C3 N1 N2 C5 0.8(4) . . . . ? C2 N1 N2 C5 174.4(3) . . . . ? C1 Se1 C8 C9 172.9(3) . . . . ? N2 N1 C3 C4 -0.6(5) . . . . ? C2 N1 C3 C4 -173.5(4) . . . . ? N2 N1 C3 C6 -178.5(4) . . . . ? C2 N1 C3 C6 8.5(7) . . . . ? C5 C4 C3 N1 0.2(5) . . . . ? C5 C4 C3 C6 177.8(5) . . . . ? N1 N2 C5 C4 -0.6(5) . . . . ? N1 N2 C5 C7 177.5(4) . . . . ? C3 C4 C5 N2 0.3(5) . . . . ? C3 C4 C5 C7 -177.6(4) . . . . ? Se1 C8 C9 C10 178.9(3) . . . . ? C3 N1 C2 C1 77.4(5) . . . . ? N2 N1 C2 C1 -95.1(4) . . . . ? N1 C2 C1 Se1 179.4(3) . . . . ? C8 Se1 C1 C2 -89.2(3) . . . . ? C8 C9 C10 O1 -13.3(7) . . . . ? C8 C9 C10 O2 168.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.436 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.087