# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Armando J. L. Pombeiro' _publ_contact_author_email POMBEIRO@IST.UTL.PT _publ_section_title ; Solvent-free microwave-assisted peroxidative oxidation of secondary alcohols to the corresponding ketones catalyzed by copper(II) 2,4-alkoxy-1,3,5-triazapentadienato complexes ; loop_ _publ_author_name 'Armando J. L. Pombeiro' 'M.F.C.G.da Silva' 'J.J.R.F.da Silva' 'Pawel J. Figiel' ; M.N.Kopylovich ; 'Jamal Lasri' # Attachment 'compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 752593' #TrackingRef 'compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 Cu N6 O4' _chemical_formula_sum 'C12 H20 Cu N6 O4' _chemical_formula_weight 375.88 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' Cu Cu 0.3201 1.2651 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.6923(13) _cell_length_b 8.2392(10) _cell_length_c 8.6199(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.190(2) _cell_angle_gamma 90.00 _cell_volume 901.42(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1712 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 28.80 _exptl_crystal_description rhombohedron _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 1.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7002 _exptl_absorpt_correction_T_max 0.8657 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 '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 5757 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 30.14 _reflns_number_total 2613 _reflns_number_gt 1556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0577P)^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 2613 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 Cu1 Cu 0.0000 0.0000 0.0000 0.03880(17) Uani 1 2 d S . . O1 O -0.27563(15) -0.2271(3) 0.1331(2) 0.0577(6) Uani 1 1 d . . . N3 N -0.18040(18) -0.0498(3) 0.2799(3) 0.0426(5) Uani 1 1 d . . . O2 O -0.09884(16) 0.1352(3) 0.4366(2) 0.0626(6) Uani 1 1 d . . . N2 N -0.02019(17) 0.0827(3) 0.2099(2) 0.0487(6) Uani 1 1 d . . . N1 N -0.12505(16) -0.1354(3) 0.0289(3) 0.0474(6) Uani 1 1 d . . . C2 C -0.0987(2) 0.0515(3) 0.3018(3) 0.0429(6) Uani 1 1 d . . . C1 C -0.18827(19) -0.1312(3) 0.1463(3) 0.0402(6) Uani 1 1 d . . . C3 C -0.3549(2) -0.2232(5) 0.2484(4) 0.0723(10) Uani 1 1 d . . . H3A H -0.3827 -0.1139 0.2570 0.087 Uiso 1 1 calc R . . H3B H -0.3246 -0.2529 0.3479 0.087 Uiso 1 1 calc R . . C4 C -0.1854(3) 0.1182(4) 0.5436(3) 0.0634(9) Uani 1 1 d . . . H4A H -0.1619 0.1464 0.6474 0.076 Uiso 1 1 calc R . . H4B H -0.2088 0.0061 0.5450 0.076 Uiso 1 1 calc R . . C5 C -0.4395(3) -0.3343(7) 0.2098(7) 0.151(3) Uani 1 1 d . . . H5A H -0.4926 -0.3294 0.2886 0.227 Uiso 1 1 calc R . . H5B H -0.4121 -0.4427 0.2036 0.227 Uiso 1 1 calc R . . H5C H -0.4696 -0.3043 0.1116 0.227 Uiso 1 1 calc R . . C6 C -0.2744(3) 0.2244(5) 0.4985(5) 0.0885(12) Uani 1 1 d . . . H6A H -0.3311 0.2107 0.5708 0.133 Uiso 1 1 calc R . . H6B H -0.2982 0.1957 0.3963 0.133 Uiso 1 1 calc R . . H6C H -0.2517 0.3355 0.4992 0.133 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 Cu1 0.0312(2) 0.0470(3) 0.0382(3) -0.0016(2) 0.00473(16) -0.0026(2) O1 0.0454(11) 0.0721(14) 0.0556(13) -0.0216(10) 0.0160(9) -0.0218(10) N3 0.0430(13) 0.0495(12) 0.0354(11) -0.0027(9) 0.0050(9) -0.0083(10) O2 0.0593(13) 0.0863(15) 0.0424(11) -0.0202(11) 0.0103(9) -0.0260(12) N2 0.0417(13) 0.0627(15) 0.0419(13) -0.0056(12) 0.0063(10) -0.0117(12) N1 0.0403(12) 0.0537(14) 0.0483(13) -0.0102(11) 0.0128(10) -0.0091(10) C2 0.0409(15) 0.0514(15) 0.0363(14) -0.0022(11) 0.0007(11) -0.0027(12) C1 0.0347(13) 0.0397(14) 0.0461(15) 0.0010(11) 0.0021(11) -0.0022(11) C3 0.0515(18) 0.101(3) 0.064(2) -0.0181(19) 0.0175(15) -0.0264(18) C4 0.069(2) 0.079(2) 0.0432(17) -0.0161(16) 0.0184(14) -0.0229(18) C5 0.089(3) 0.194(6) 0.171(5) -0.090(5) 0.073(3) -0.079(4) C6 0.084(3) 0.087(3) 0.095(3) -0.029(2) 0.023(2) -0.004(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 Cu1 N2 1.951(2) 3 ? Cu1 N2 1.951(2) . ? Cu1 N1 1.957(2) . ? Cu1 N1 1.957(2) 3 ? O1 C1 1.366(3) . ? O1 C3 1.417(3) . ? N3 C1 1.336(3) . ? N3 C2 1.344(4) . ? O2 C2 1.351(3) . ? O2 C4 1.444(3) . ? N2 C2 1.300(3) . ? N1 C1 1.294(3) . ? C3 C5 1.448(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.479(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 N2 Cu1 N2 180.00(13) 3 . ? N2 Cu1 N1 91.61(9) 3 . ? N2 Cu1 N1 88.39(9) . . ? N2 Cu1 N1 88.39(9) 3 3 ? N2 Cu1 N1 91.61(9) . 3 ? N1 Cu1 N1 180.00(13) . 3 ? C1 O1 C3 120.4(2) . . ? C1 N3 C2 119.2(2) . . ? C2 O2 C4 120.2(2) . . ? C2 N2 Cu1 126.8(2) . . ? C1 N1 Cu1 126.14(19) . . ? N2 C2 N3 129.0(3) . . ? N2 C2 O2 115.2(2) . . ? N3 C2 O2 115.7(2) . . ? N1 C1 N3 130.0(2) . . ? N1 C1 O1 115.1(2) . . ? N3 C1 O1 114.9(2) . . ? O1 C3 C5 110.6(3) . . ? O1 C3 H3A 109.5 . . ? C5 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? C5 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O2 C4 C6 110.9(3) . . ? O2 C4 H4A 109.5 . . ? C6 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? C6 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.14 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.465 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.068