# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Andrei I. Khlebnikov' _publ_contact_author_address ;Prof. Andrei I. Khlebnikov Department of Chemistry Altai State Technical University Barnaul 656038, Russia ; _publ_contact_author_email aikhl@chem.org.ru _publ_contact_author_phone 7(3852)245513 _publ_contact_author_fax 7(3852)367864 loop_ _publ_author_name _publ_author_address A.I.Khlebnikov ;Department of Chemistry Altai State Technical University Barnaul 656038, Russia ; A.S.Potapov ;Department of Chemistry Altai State Technical University Barnaul 656038, Russia ; E.A.Nudnova ;Department of Chemistry Altai State Technical University Barnaul 656038, Russia ; G.A.Domina ;Department of Chemistry Altai State Technical University Barnaul 656038, Russia ; ; I.A.Schepetkin ; ;Veterinary Molecular Biology Montana State University Bozeman, MT 59717 ; L.N.Kirpotina ;Veterinary Molecular Biology Montana State University Bozeman, MT 59717 ; M.T.Quinn ;Veterinary Molecular Biology Montana State University Bozeman, MT 59717 ; _publ_section_title ;Synthesis, characterization and potent superoxide dismutase like activity of novel bis(pyrazole) - 2,2'-bipyridyl mixed ligand copper(II) complexes ; data_cpl _database_code_depnum_ccdc_archive 'CCDC 713520' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[2-(3,5-dimethylpyrazol-1-yl)ethyl]etherdinitratocopper ; _chemical_name_common Bis(2-(3,5-dimethylpyrazol-1-yl)ethyl)etherdinitratocopper _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cu N6 O7' _chemical_formula_sum 'C14 H22 Cu N6 O7' _chemical_formula_weight 449.92 _exptl_crystal_recrystallization_method acetone 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 17.4261(7) _cell_length_b 10.3459(3) _cell_length_c 11.1392(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.1200(10) _cell_angle_gamma 90.00 _cell_volume 1919.29(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8268 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.188 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6413 _exptl_absorpt_correction_T_max 0.7175 _exptl_absorpt_process_details 'Higashi, T. (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-spider' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9186 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2202 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_cell_refinement 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_data_reduction 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'Crystal Structure' _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^)+(0.0281P)^2^+1.3954P] 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 2202 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0222 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 Cu Cu 0.0000 0.32730(2) 0.2500 0.01803(8) Uani 1 2 d S . . O1 O 0.0000 0.55018(13) 0.2500 0.0233(3) Uani 1 2 d S . . O2 O -0.07395(6) 0.31693(9) 0.35784(9) 0.0245(2) Uani 1 1 d . . . O3 O -0.16100(7) 0.18453(11) 0.39483(12) 0.0370(3) Uani 1 1 d . . . O4 O -0.08541(7) 0.12169(10) 0.28233(10) 0.0309(2) Uani 1 1 d . . . N1 N 0.09430(7) 0.33652(11) 0.40514(10) 0.0207(2) Uani 1 1 d . . . N2 N 0.14507(7) 0.44051(11) 0.43282(10) 0.0203(2) Uani 1 1 d . . . N5 N -0.10810(7) 0.20399(12) 0.34393(11) 0.0248(3) Uani 1 1 d . . . C1 C 0.07571(10) 0.13372(14) 0.51290(14) 0.0287(3) Uani 1 1 d . . . H1A H 0.0578 0.0933 0.4297 0.043 Uiso 1 1 calc R . . H1B H 0.0291 0.1512 0.5426 0.043 Uiso 1 1 calc R . . H1C H 0.1126 0.0753 0.5718 0.043 Uiso 1 1 calc R . . C2 C 0.11771(8) 0.25750(13) 0.50469(12) 0.0219(3) Uani 1 1 d . . . C3 C 0.18352(8) 0.31107(14) 0.59454(13) 0.0236(3) Uani 1 1 d . . . H3A H 0.2118 0.2743 0.6733 0.028 Uiso 1 1 calc R . . C4 C 0.19950(8) 0.42760(14) 0.54693(12) 0.0219(3) Uani 1 1 d . . . C5 C 0.26063(9) 0.52849(16) 0.60251(14) 0.0299(3) Uani 1 1 d . . . H5A H 0.2943 0.5022 0.6865 0.036 Uiso 1 1 d R . . H5B H 0.2326 0.6098 0.6119 0.036 Uiso 1 1 d R . . H5C H 0.2937 0.5436 0.5479 0.036 Uiso 1 1 d R . . C6 C 0.14198(8) 0.54207(14) 0.34089(13) 0.0233(3) Uani 1 1 d . . . H6A H 0.1437 0.5018 0.2611 0.028 Uiso 1 1 calc R . . H6B H 0.1902 0.5973 0.3714 0.028 Uiso 1 1 calc R . . C7 C 0.06801(8) 0.62613(13) 0.31529(13) 0.0234(3) Uani 1 1 d . . . H7A H 0.0613 0.6582 0.3954 0.028 Uiso 1 1 calc R . . H7B H 0.0733 0.7015 0.2636 0.028 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 Cu 0.02290(13) 0.01689(12) 0.01481(12) 0.000 0.00632(8) 0.000 O1 0.0215(7) 0.0160(6) 0.0285(7) 0.000 0.0014(5) 0.000 O2 0.0300(5) 0.0231(5) 0.0224(5) -0.0007(4) 0.0108(4) -0.0065(4) O3 0.0304(6) 0.0391(6) 0.0468(7) 0.0129(5) 0.0195(5) -0.0028(5) O4 0.0400(6) 0.0239(5) 0.0286(5) -0.0019(4) 0.0097(5) -0.0040(4) N1 0.0247(6) 0.0188(5) 0.0189(5) 0.0018(4) 0.0068(4) -0.0007(4) N2 0.0201(5) 0.0211(5) 0.0196(5) 0.0023(4) 0.0059(4) 0.0005(4) N5 0.0241(6) 0.0256(6) 0.0233(6) 0.0065(5) 0.0046(5) -0.0025(5) C1 0.0387(8) 0.0217(7) 0.0249(7) 0.0063(6) 0.0080(6) 0.0016(6) C2 0.0273(7) 0.0211(6) 0.0188(6) 0.0029(5) 0.0090(5) 0.0055(5) C3 0.0252(7) 0.0272(7) 0.0184(6) 0.0036(5) 0.0063(5) 0.0079(5) C4 0.0191(6) 0.0269(7) 0.0203(6) -0.0003(5) 0.0067(5) 0.0047(5) C5 0.0228(7) 0.0352(8) 0.0286(7) 0.0011(6) 0.0028(6) -0.0017(6) C6 0.0238(7) 0.0235(7) 0.0228(6) 0.0052(5) 0.0071(5) -0.0021(5) C7 0.0259(7) 0.0179(6) 0.0239(6) 0.0005(5) 0.0034(5) -0.0027(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 Cu N1 2.0060(11) . ? Cu N1 2.0060(11) 2 ? Cu O2 2.0067(10) 2 ? Cu O2 2.0067(10) . ? Cu O1 2.3059(13) . ? O1 C7 1.4295(15) . ? O1 C7 1.4295(15) 2 ? O2 N5 1.2996(15) . ? O3 N5 1.2329(16) . ? O4 N5 1.2296(17) . ? N1 C2 1.3409(17) . ? N1 N2 1.3691(15) . ? N2 C4 1.3504(17) . ? N2 C6 1.4571(17) . ? C1 C2 1.491(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.396(2) . ? C3 C4 1.378(2) . ? C3 H3A 0.9500 . ? C4 C5 1.490(2) . ? C5 H5A 0.9853 . ? C5 H5B 0.9941 . ? C5 H5C 0.9669 . ? C6 C7 1.5108(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 Cu N1 174.55(6) . 2 ? N1 Cu O2 90.61(4) . 2 ? N1 Cu O2 89.68(4) 2 2 ? N1 Cu O2 89.68(4) . . ? N1 Cu O2 90.61(4) 2 . ? O2 Cu O2 173.87(6) 2 . ? N1 Cu O1 87.28(3) . . ? N1 Cu O1 87.28(3) 2 . ? O2 Cu O1 93.07(3) 2 . ? O2 Cu O1 93.07(3) . . ? C7 O1 C7 113.31(14) . 2 ? C7 O1 Cu 123.34(7) . . ? C7 O1 Cu 123.34(7) 2 . ? N5 O2 Cu 109.20(8) . . ? C2 N1 N2 105.89(11) . . ? C2 N1 Cu 131.00(10) . . ? N2 N1 Cu 122.85(8) . . ? C4 N2 N1 111.25(11) . . ? C4 N2 C6 127.10(12) . . ? N1 N2 C6 121.38(11) . . ? O4 N5 O3 123.39(13) . . ? O4 N5 O2 118.56(12) . . ? O3 N5 O2 118.04(12) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.67(12) . . ? N1 C2 C1 122.61(12) . . ? C3 C2 C1 127.71(12) . . ? C4 C3 C2 106.73(12) . . ? C4 C3 H3A 126.6 . . ? C2 C3 H3A 126.6 . . ? N2 C4 C3 106.45(12) . . ? N2 C4 C5 122.69(13) . . ? C3 C4 C5 130.83(13) . . ? C4 C5 H5A 110.8 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.9 . . ? C4 C5 H5C 109.8 . . ? H5A C5 H5C 110.1 . . ? H5B C5 H5C 109.4 . . ? N2 C6 C7 113.63(11) . . ? N2 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N2 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O1 C7 C6 108.25(11) . . ? O1 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu O1 C7 19.92(8) . . . . ? N1 Cu O1 C7 -160.08(8) 2 . . . ? O2 Cu O1 C7 -70.55(8) 2 . . . ? O2 Cu O1 C7 109.45(8) . . . . ? N1 Cu O1 C7 -160.08(8) . . . 2 ? N1 Cu O1 C7 19.92(8) 2 . . 2 ? O2 Cu O1 C7 109.45(8) 2 . . 2 ? O2 Cu O1 C7 -70.55(8) . . . 2 ? N1 Cu O2 N5 -113.56(9) . . . . ? N1 Cu O2 N5 71.88(9) 2 . . . ? O1 Cu O2 N5 159.19(8) . . . . ? O2 Cu N1 C2 -118.73(12) 2 . . . ? O2 Cu N1 C2 55.14(12) . . . . ? O1 Cu N1 C2 148.23(12) . . . . ? O2 Cu N1 N2 67.96(10) 2 . . . ? O2 Cu N1 N2 -118.17(10) . . . . ? O1 Cu N1 N2 -25.08(9) . . . . ? C2 N1 N2 C4 0.19(14) . . . . ? Cu N1 N2 C4 174.95(9) . . . . ? C2 N1 N2 C6 174.67(12) . . . . ? Cu N1 N2 C6 -10.58(16) . . . . ? Cu O2 N5 O4 7.24(14) . . . . ? Cu O2 N5 O3 -173.70(10) . . . . ? N2 N1 C2 C3 -0.48(15) . . . . ? Cu N1 C2 C3 -174.64(9) . . . . ? N2 N1 C2 C1 178.30(12) . . . . ? Cu N1 C2 C1 4.1(2) . . . . ? N1 C2 C3 C4 0.59(15) . . . . ? C1 C2 C3 C4 -178.12(13) . . . . ? N1 N2 C4 C3 0.17(14) . . . . ? C6 N2 C4 C3 -173.92(12) . . . . ? N1 N2 C4 C5 -178.14(12) . . . . ? C6 N2 C4 C5 7.8(2) . . . . ? C2 C3 C4 N2 -0.45(14) . . . . ? C2 C3 C4 C5 177.67(14) . . . . ? C4 N2 C6 C7 -115.69(14) . . . . ? N1 N2 C6 C7 70.77(16) . . . . ? C7 O1 C7 C6 -160.47(13) 2 . . . ? Cu O1 C7 C6 19.53(13) . . . . ? N2 C6 C7 O1 -69.07(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.317 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.052