Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Francesco Paolo Fanizzi' _publ_contact_author_address ; Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali Universita` di Lecce Prov.le Lecce-Monteroni Lecce I-73100 ITALY ; _publ_contact_author_email FP.FANIZZI@UNILE.IT _publ_requested_category 'Full article' _publ_section_title ; Stereospecific metal mediated ortho-alkylation of phenol. First platinum containing organometallic chromane analogues ; _publ_section_title_footnote ? loop_ _publ_author_name _publ_author_address 'Francesco P. Fanizzi' ; Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali Universita' di Lecce Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy ; 'Francesco Capitelli' ; Istituto di Cristallografia-CNR Via Amendola 122/o, 70126 Bari, Italy ; 'Michele Benedetti' ; Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali Universita' di Lecce Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy ; 'Antonella Ciccarese' . ; S.A.De Pascali ; . 'Santo Marsigliante' . 'Danilo Migoni' . 'Vita M. Vecchio' . data_ben1 _database_code_depnum_ccdc_archive 'CCDC 603625' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N2 O Pt' _chemical_formula_sum 'C20 H16 N2 O Pt' _chemical_formula_weight 495.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Pt Pt -1.7033 8.3905 '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' 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' _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 7.5060(10) _cell_length_b 20.254(2) _cell_length_c 10.7330(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.473(6) _cell_angle_gamma 90.00 _cell_volume 1593.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 173 _cell_measurement_theta_min 3.87 _cell_measurement_theta_max 22.47 _exptl_crystal_description prisma _exptl_crystal_colour red _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.066 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 8.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5774 _exptl_absorpt_correction_T_max 0.8434 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction; Siemens Industrial Automation, Inc.: Madison, WI, 1996. ; _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 'Nonius kappa CCD' _diffrn_measurement_method 'phi and omega scans mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9761 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.04 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3471 _reflns_number_gt 2467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0248P)^2^+5.1749P] 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 3471 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 Pt1 Pt 0.89473(4) 0.096003(17) 0.66035(3) 0.04970(13) Uani 1 1 d . . . O1 O 0.9964(8) 0.1880(3) 0.6916(6) 0.0637(17) Uani 1 1 d . . . N1 N 0.7862(8) 0.0080(4) 0.6018(6) 0.0459(16) Uani 1 1 d . . . N2 N 0.8519(8) 0.1099(3) 0.4611(6) 0.0464(17) Uani 1 1 d . . . C1 C 0.7577(13) -0.0430(5) 0.6713(11) 0.058(2) Uani 1 1 d . . . C2 C 0.6741(13) -0.1008(5) 0.6177(12) 0.063(3) Uani 1 1 d . . . C3 C 0.6209(13) -0.1071(5) 0.4897(11) 0.062(3) Uani 1 1 d . . . C4 C 0.6524(11) -0.0544(5) 0.4114(9) 0.052(2) Uani 1 1 d . . . C5 C 0.7372(10) 0.0026(4) 0.4723(8) 0.046(2) Uani 1 1 d . . . C6 C 0.7729(10) 0.0555(4) 0.3971(8) 0.0449(19) Uani 1 1 d . . . C7 C 0.8946(11) 0.1606(5) 0.3955(10) 0.056(2) Uani 1 1 d . . . C8 C 0.8600(14) 0.1607(6) 0.2636(11) 0.064(3) Uani 1 1 d . . . C9 C 0.7772(13) 0.1073(6) 0.1975(11) 0.062(3) Uani 1 1 d . . . C10 C 0.7286(11) 0.0525(5) 0.2633(9) 0.055(2) Uani 1 1 d . . . C11 C 0.6022(13) -0.0565(6) 0.2751(11) 0.062(3) Uani 1 1 d . . . C12 C 0.6397(12) -0.0056(6) 0.2059(10) 0.061(3) Uani 1 1 d . . . C13 C 0.9385(14) 0.0766(6) 0.8512(9) 0.059(3) Uani 1 1 d . . . C14 C 1.0204(15) 0.1334(7) 0.9370(10) 0.068(3) Uani 1 1 d . . . C15 C 1.1817(12) 0.1653(5) 0.8987(8) 0.055(2) Uani 1 1 d . . . C16 C 1.1566(12) 0.1940(4) 0.7766(8) 0.053(2) Uani 1 1 d . . . C17 C 1.2994(14) 0.2260(5) 0.7422(11) 0.062(3) Uani 1 1 d . . . C18 C 1.4659(15) 0.2319(5) 0.8234(12) 0.073(3) Uani 1 1 d . . . C19 C 1.4953(15) 0.2061(6) 0.9415(11) 0.073(3) Uani 1 1 d . . . C20 C 1.3514(14) 0.1726(6) 0.9779(10) 0.067(3) Uani 1 1 d . . . H1 H 0.800(12) -0.039(5) 0.744(8) 0.06(3) Uiso 1 1 d . . . H2 H 0.654(8) -0.130(4) 0.670(6) 0.025(18) Uiso 1 1 d . . . H3 H 0.552(10) -0.150(4) 0.454(7) 0.05(2) Uiso 1 1 d . . . H7 H 0.945(9) 0.202(4) 0.447(7) 0.05(2) Uiso 1 1 d . . . H8 H 0.892(11) 0.193(5) 0.227(8) 0.05(3) Uiso 1 1 d . . . H9 H 0.755(14) 0.103(5) 0.117(10) 0.08(4) Uiso 1 1 d . . . H11 H 0.542(12) -0.089(5) 0.251(8) 0.05(3) Uiso 1 1 d . . . H12 H 0.610(11) -0.005(4) 0.119(9) 0.06(3) Uiso 1 1 d . . . H13A H 0.833(9) 0.066(4) 0.877(6) 0.028(18) Uiso 1 1 d . . . H13B H 0.960(14) 0.031(6) 0.872(10) 0.09(4) Uiso 1 1 d . . . H17A H 1.068(16) 0.112(6) 1.016(12) 0.11(4) Uiso 1 1 d . . . H17B H 0.914(14) 0.166(6) 0.930(9) 0.09(4) Uiso 1 1 d . . . H17 H 1.275(11) 0.235(4) 0.665(8) 0.05(3) Uiso 1 1 d . . . H18 H 1.563(13) 0.258(5) 0.801(9) 0.08(3) Uiso 1 1 d . . . H19 H 1.618(12) 0.215(5) 1.003(8) 0.07(3) Uiso 1 1 d . . . H20 H 1.378(9) 0.162(4) 1.052(7) 0.03(2) 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 Pt1 0.04410(19) 0.0486(2) 0.0572(2) 0.0005(2) 0.01255(13) 0.00423(17) O1 0.057(4) 0.056(4) 0.071(4) 0.003(3) -0.003(3) -0.003(3) N1 0.039(3) 0.050(4) 0.050(4) 0.004(4) 0.012(3) 0.005(3) N2 0.041(4) 0.046(5) 0.052(4) 0.004(3) 0.010(3) 0.004(3) C1 0.051(5) 0.061(7) 0.062(7) 0.011(6) 0.013(5) 0.009(5) C2 0.061(6) 0.044(6) 0.092(8) 0.019(6) 0.031(5) 0.005(5) C3 0.063(6) 0.044(6) 0.085(8) -0.002(5) 0.028(5) 0.005(4) C4 0.044(4) 0.059(6) 0.056(6) 0.002(5) 0.020(4) 0.016(4) C5 0.037(4) 0.044(5) 0.060(5) 0.002(4) 0.014(4) 0.008(3) C6 0.037(4) 0.039(5) 0.058(5) 0.001(4) 0.010(3) 0.012(3) C7 0.051(5) 0.050(6) 0.067(7) 0.006(5) 0.014(4) 0.000(4) C8 0.060(6) 0.066(8) 0.068(7) 0.023(6) 0.023(5) 0.009(5) C9 0.060(6) 0.070(8) 0.060(7) 0.007(6) 0.021(5) 0.012(5) C10 0.043(5) 0.061(6) 0.062(6) -0.008(5) 0.013(4) 0.013(4) C11 0.045(5) 0.053(7) 0.092(8) -0.011(6) 0.023(5) 0.003(5) C12 0.053(5) 0.081(8) 0.051(6) -0.019(6) 0.012(4) 0.004(5) C13 0.058(6) 0.066(7) 0.057(6) 0.010(5) 0.025(5) -0.007(5) C14 0.067(6) 0.089(9) 0.051(6) 0.001(6) 0.019(5) -0.003(6) C15 0.069(6) 0.048(6) 0.049(5) -0.006(4) 0.014(4) 0.004(4) C16 0.070(6) 0.041(5) 0.052(5) -0.010(4) 0.018(4) 0.005(4) C17 0.082(7) 0.052(6) 0.056(7) -0.001(5) 0.021(5) -0.003(5) C18 0.068(7) 0.052(7) 0.099(9) -0.007(6) 0.017(6) -0.009(5) C19 0.066(7) 0.065(7) 0.080(8) -0.008(6) -0.002(6) -0.005(5) C20 0.083(8) 0.072(8) 0.045(6) -0.006(5) 0.011(5) 0.008(6) _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 Pt1 N1 2.003(7) . ? Pt1 O1 2.013(6) . ? Pt1 C13 2.041(10) . ? Pt1 N2 2.111(7) . ? O1 C16 1.349(10) . ? N1 C1 1.318(11) . ? N1 C5 1.364(10) . ? N2 C7 1.324(11) . ? N2 C6 1.365(10) . ? C1 C2 1.393(14) . ? C1 H1 0.78(8) . ? C2 C3 1.351(14) . ? C2 H2 0.85(7) . ? C3 C4 1.409(13) . ? C3 H3 1.04(8) . ? C4 C5 1.409(12) . ? C4 C11 1.431(13) . ? C5 C6 1.402(11) . ? C6 C10 1.403(11) . ? C7 C8 1.383(14) . ? C7 H7 1.03(8) . ? C8 C9 1.367(15) . ? C8 H8 0.82(9) . ? C9 C10 1.406(14) . ? C9 H9 0.85(11) . ? C10 C12 1.425(13) . ? C11 C12 1.336(14) . ? C11 H11 0.81(9) . ? C12 H12 0.92(9) . ? C13 C14 1.517(15) . ? C13 H13A 0.92(7) . ? C13 H13B 0.95(12) . ? C14 C15 1.506(13) . ? C14 H17A 0.95(12) . ? C14 H17B 1.03(11) . ? C15 C20 1.378(13) . ? C15 C16 1.409(12) . ? C16 C17 1.370(13) . ? C17 C18 1.366(14) . ? C17 H17 0.83(8) . ? C18 C19 1.344(15) . ? C18 H18 0.97(10) . ? C19 C20 1.401(15) . ? C19 H19 1.02(9) . ? C20 H20 0.80(7) . ? 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 Pt1 O1 171.5(3) . . ? N1 Pt1 C13 96.3(4) . . ? O1 Pt1 C13 92.1(4) . . ? N1 Pt1 N2 80.7(3) . . ? O1 Pt1 N2 90.8(3) . . ? C13 Pt1 N2 176.5(4) . . ? C16 O1 Pt1 116.5(5) . . ? C1 N1 C5 118.2(8) . . ? C1 N1 Pt1 128.7(7) . . ? C5 N1 Pt1 113.2(6) . . ? C7 N2 C6 119.2(8) . . ? C7 N2 Pt1 129.9(6) . . ? C6 N2 Pt1 110.9(5) . . ? N1 C1 C2 122.6(10) . . ? N1 C1 H1 114(8) . . ? C2 C1 H1 124(8) . . ? C3 C2 C1 120.4(10) . . ? C3 C2 H2 123(5) . . ? C1 C2 H2 116(5) . . ? C2 C3 C4 119.0(10) . . ? C2 C3 H3 118(4) . . ? C4 C3 H3 123(4) . . ? C5 C4 C3 117.4(9) . . ? C5 C4 C11 119.4(9) . . ? C3 C4 C11 123.2(10) . . ? N1 C5 C6 118.8(8) . . ? N1 C5 C4 122.3(8) . . ? C6 C5 C4 118.9(8) . . ? N2 C6 C5 116.3(7) . . ? N2 C6 C10 122.1(8) . . ? C5 C6 C10 121.6(8) . . ? N2 C7 C8 122.1(10) . . ? N2 C7 H7 117(4) . . ? C8 C7 H7 121(4) . . ? C9 C8 C7 119.6(11) . . ? C9 C8 H8 122(6) . . ? C7 C8 H8 119(6) . . ? C8 C9 C10 120.1(10) . . ? C8 C9 H9 125(7) . . ? C10 C9 H9 115(7) . . ? C6 C10 C9 116.8(9) . . ? C6 C10 C12 117.6(9) . . ? C9 C10 C12 125.6(10) . . ? C12 C11 C4 120.4(11) . . ? C12 C11 H11 128(7) . . ? C4 C11 H11 111(6) . . ? C11 C12 C10 122.1(10) . . ? C11 C12 H12 123(6) . . ? C10 C12 H12 115(6) . . ? C14 C13 Pt1 114.8(8) . . ? C14 C13 H13A 104(4) . . ? Pt1 C13 H13A 113(4) . . ? C14 C13 H13B 124(7) . . ? Pt1 C13 H13B 114(7) . . ? H13A C13 H13B 80(7) . . ? C15 C14 C13 113.8(8) . . ? C15 C14 H17A 106(7) . . ? C13 C14 H17A 103(8) . . ? C15 C14 H17B 111(6) . . ? C13 C14 H17B 104(6) . . ? H17A C14 H17B 120(9) . . ? C20 C15 C16 116.7(9) . . ? C20 C15 C14 124.7(9) . . ? C16 C15 C14 118.5(8) . . ? O1 C16 C17 119.7(9) . . ? O1 C16 C15 120.8(8) . . ? C17 C16 C15 119.4(9) . . ? C18 C17 C16 122.1(11) . . ? C18 C17 H17 127(6) . . ? C16 C17 H17 111(6) . . ? C19 C18 C17 120.6(11) . . ? C19 C18 H18 118(6) . . ? C17 C18 H18 122(6) . . ? C18 C19 C20 118.2(10) . . ? C18 C19 H19 119(5) . . ? C20 C19 H19 123(5) . . ? C15 C20 C19 123.1(10) . . ? C15 C20 H20 125(5) . . ? C19 C20 H20 111(5) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 2.287 _refine_diff_density_min -1.020 _refine_diff_density_rms 0.133