# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Daniel Sole' 'Merce Font-Bardia' 'Xavier Solans' 'Lluis Vallverdu' _publ_contact_author_name 'Dr Daniel Sole' _publ_contact_author_address ; Laboratori de Quimica Org\`anica Universitat de Barcelona Facultat de Farmacia Av. Joan XXII s/n Barcelona 08028 SPAIN ; _publ_contact_author_email DSOLE@UB.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis of novel palladium OCN-pincer complexes: Unprecedented sequential C(sp3)-H activation and aerobic oxidation in the reaction of N,N-dialkyl-3-[(N,N-dimethylamino)methyl]-2-iodoanilines with Pd2(dba)3 ; data_soic8a _database_code_depnum_ccdc_archive 'CCDC 265336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 I N2 O Pd' _chemical_formula_sum 'C11 H15 I N2 O Pd' _chemical_formula_weight 424.55 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' I I -0.4742 1.8119 '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' Pd Pd -0.9988 1.0072 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.190(8) _cell_length_b 11.219(3) _cell_length_c 11.646(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.37(3) _cell_angle_gamma 90.00 _cell_volume 1309.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 3.756 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3977 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 29.96 _reflns_number_total 3767 _reflns_number_gt 3079 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0496P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3767 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 Pd Pd 0.198388(18) 0.545395(17) 0.771636(16) 0.03851(7) Uani 1 1 d . . . I I 0.12132(2) 0.312801(18) 0.73178(2) 0.06122(8) Uani 1 1 d . . . O O 0.1133(2) 0.54771(17) 0.91650(17) 0.0490(4) Uani 1 1 d . . . N1 N 0.2849(2) 0.5680(2) 0.6241(2) 0.0501(5) Uani 1 1 d . . . N2 N 0.0991(2) 0.7511(2) 0.94425(19) 0.0437(4) Uani 1 1 d . . . C1 C 0.2339(3) 0.7154(2) 0.7919(2) 0.0409(5) Uani 1 1 d . . . C2 C 0.1826(3) 0.7921(2) 0.8632(2) 0.0429(5) Uani 1 1 d . . . C3 C 0.2054(3) 0.9166(3) 0.8587(3) 0.0568(7) Uani 1 1 d . . . C4 C 0.2868(4) 0.9594(3) 0.7829(3) 0.0659(9) Uani 1 1 d . . . C5 C 0.3427(4) 0.8842(3) 0.7143(3) 0.0620(8) Uani 1 1 d . . . C6 C 0.3183(3) 0.7625(3) 0.7192(2) 0.0483(6) Uani 1 1 d . . . C7 C 0.3779(3) 0.6710(3) 0.6468(3) 0.0558(7) Uani 1 1 d . . . H7 H 0.3906 0.7063 0.5735 0.067 Uiso 1 1 calc R . . H7A H 0.4640 0.6447 0.6886 0.067 Uiso 1 1 calc R . . C8 C 0.3585(4) 0.4638(4) 0.5889(4) 0.0786(11) Uani 1 1 d . . . H8 H 0.4294 0.4426 0.6516 0.094 Uiso 1 1 calc R . . H8A H 0.3951 0.4838 0.5210 0.094 Uiso 1 1 calc R . . H8B H 0.2984 0.3977 0.5714 0.094 Uiso 1 1 calc R . . C9 C 0.1758(3) 0.6005(3) 0.5271(3) 0.0613(8) Uani 1 1 d . . . H9 H 0.2091 0.6012 0.4551 0.074 Uiso 1 1 calc R . . H9A H 0.1424 0.6781 0.5412 0.074 Uiso 1 1 calc R . . H9B H 0.1051 0.5431 0.5222 0.074 Uiso 1 1 calc R . . C10 C 0.0762(3) 0.6368(2) 0.9641(2) 0.0466(6) Uani 1 1 d . . . H10 H 0.0256 0.6221 1.0215 0.056 Uiso 1 1 calc R . . C11 C 0.0362(3) 0.8393(3) 1.0109(3) 0.0594(8) Uani 1 1 d . . . H11 H 0.0596 0.9182 0.9900 0.071 Uiso 1 1 calc R . . H11A H 0.0670 0.8271 1.0930 0.071 Uiso 1 1 calc R . . H11B H -0.0590 0.8301 0.9933 0.071 Uiso 1 1 calc R . . H3 H 0.188(3) 0.982(3) 0.910(3) 0.053(9) Uiso 1 1 d . . . H4 H 0.320(4) 1.043(3) 0.780(4) 0.078(12) Uiso 1 1 d . . . H5 H 0.405(4) 0.916(3) 0.675(4) 0.066(11) Uiso 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 Pd 0.03481(10) 0.04012(11) 0.04098(10) 0.00231(7) 0.00783(7) -0.00041(7) I 0.07113(15) 0.04443(12) 0.07240(15) -0.00863(9) 0.02451(11) -0.00652(8) O 0.0645(12) 0.0414(9) 0.0450(10) 0.0074(8) 0.0200(9) 0.0020(8) N1 0.0404(11) 0.0628(15) 0.0511(13) -0.0052(10) 0.0189(10) -0.0082(10) N2 0.0477(11) 0.0417(11) 0.0406(10) -0.0015(9) 0.0046(8) -0.0029(9) C1 0.0411(12) 0.0411(12) 0.0381(11) 0.0091(10) 0.0004(9) -0.0039(10) C2 0.0451(13) 0.0419(12) 0.0379(12) 0.0017(10) -0.0032(10) -0.0095(10) C3 0.0658(18) 0.0463(15) 0.0532(16) 0.0037(13) -0.0030(14) -0.0155(14) C4 0.079(2) 0.0504(17) 0.064(2) 0.0078(15) 0.0012(17) -0.0246(16) C5 0.0640(19) 0.0641(19) 0.0520(16) 0.0153(15) -0.0056(14) -0.0266(16) C6 0.0399(13) 0.0586(16) 0.0422(13) 0.0080(11) -0.0036(10) -0.0137(11) C7 0.0392(14) 0.076(2) 0.0538(16) 0.0055(14) 0.0117(12) -0.0130(13) C8 0.067(2) 0.086(3) 0.095(3) -0.013(2) 0.046(2) 0.0070(18) C9 0.0505(16) 0.090(2) 0.0449(14) -0.0048(15) 0.0114(12) -0.0165(16) C10 0.0548(15) 0.0474(14) 0.0384(12) 0.0039(10) 0.0111(11) -0.0042(11) C11 0.072(2) 0.0479(16) 0.0607(18) -0.0123(13) 0.0187(16) 0.0014(14) _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 Pd C1 1.948(3) . ? Pd O 2.031(2) . ? Pd N1 2.083(2) . ? Pd I 2.7405(7) . ? O C10 1.235(3) . ? N1 C9 1.481(4) . ? N1 C8 1.486(4) . ? N1 C7 1.488(4) . ? N2 C10 1.331(3) . ? N2 C2 1.455(4) . ? N2 C11 1.474(4) . ? C1 C2 1.363(4) . ? C1 C6 1.414(4) . ? C2 C3 1.418(4) . ? C3 C4 1.400(5) . ? C3 H3 0.98(3) . ? C4 C5 1.356(6) . ? C4 H4 1.00(4) . ? C5 C6 1.391(4) . ? C5 H5 0.92(4) . ? C6 C7 1.522(5) . ? C7 H7 0.9700 . ? C7 H7A 0.9700 . ? C8 H8 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C9 H9 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 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 Pd O 89.11(9) . . ? C1 Pd N1 83.32(10) . . ? O Pd N1 172.26(9) . . ? C1 Pd I 173.86(8) . . ? O Pd I 90.04(6) . . ? N1 Pd I 97.32(7) . . ? C10 O Pd 126.43(18) . . ? C9 N1 C8 109.3(3) . . ? C9 N1 C7 108.1(3) . . ? C8 N1 C7 108.9(3) . . ? C9 N1 Pd 106.73(17) . . ? C8 N1 Pd 116.2(2) . . ? C7 N1 Pd 107.41(18) . . ? C10 N2 C2 124.0(2) . . ? C10 N2 C11 116.7(2) . . ? C2 N2 C11 119.4(2) . . ? C2 C1 C6 118.0(3) . . ? C2 C1 Pd 127.52(19) . . ? C6 C1 Pd 114.4(2) . . ? C1 C2 C3 121.1(3) . . ? C1 C2 N2 121.9(2) . . ? C3 C2 N2 117.0(3) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 109(2) . . ? C2 C3 H3 132(2) . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 112(3) . . ? C3 C4 H4 126(3) . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 117(2) . . ? C6 C5 H5 123(2) . . ? C5 C6 C1 121.6(3) . . ? C5 C6 C7 123.1(3) . . ? C1 C6 C7 115.3(3) . . ? N1 C7 C6 108.5(2) . . ? N1 C7 H7 110.0 . . ? C6 C7 H7 110.0 . . ? N1 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? H7 C7 H7A 108.4 . . ? N1 C8 H8 109.5 . . ? N1 C8 H8A 109.5 . . ? H8 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C9 H9 109.5 . . ? N1 C9 H9A 109.5 . . ? H9 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O C10 N2 128.7(2) . . ? O C10 H10 115.7 . . ? N2 C10 H10 115.7 . . ? N2 C11 H11 109.5 . . ? N2 C11 H11A 109.5 . . ? H11 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.809 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.138