# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Andrei Vedernikov' _publ_contact_author_email AVEDERNI@UMD.EDU _publ_section_title ; Catalytic Aerobic Oxidation of Substituted 8-Methylquinolines in PdII - 2,6-Pyridinedicarboxylic Acid Systems ; loop_ _publ_author_name 'Andrei Vedernikov' 'Nicholas P Anderson' 'Eugene Khaskin' 'Peter Zavalij' 'Jing Zhang.' # Attachment '1596-new.cif' data_1596 _database_code_depnum_ccdc_archive 'CCDC 679231' _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; Pd-complex ; _chemical_name_common Pd-complex _chemical_formula_moiety 'C21 H20 N2 O4 Pd, C H2 Cl2' _chemical_formula_sum 'C22 H22 Cl2 N2 O4 Pd' _chemical_formula_weight 555.72 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8530(3) _cell_length_b 10.5424(3) _cell_length_c 10.9053(3) _cell_angle_alpha 95.7794(4) _cell_angle_beta 96.0116(4) _cell_angle_gamma 100.7455(4) _cell_volume 1098.39(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13725 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.9 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.185 _exptl_crystal_size_mid 0.075 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 1.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.919 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 150(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 'three-circle diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 22144 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6360 _reflns_number_gt 5880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _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 'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+1.462P], P=(max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6360 _refine_ls_number_parameters 303 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0523 _refine_ls_wR_factor_gt 0.0514 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 Pd1 Pd 0.248127(13) 0.444647(12) 0.452622(11) 0.01600(4) Uani 1 1 d . . . N1 N 0.38860(14) 0.36307(13) 0.54569(13) 0.0188(3) Uani 1 1 d . . . C10 C 0.27885(19) 0.32214(18) 0.30782(16) 0.0235(3) Uani 1 1 d . . . H10A H 0.1904 0.2613 0.2749 0.034(6) Uiso 1 1 calc R . . H10B H 0.3103 0.3724 0.2405 0.035(6) Uiso 1 1 calc R . . C11 C 0.43614(19) 0.39366(18) 0.66515(16) 0.0238(3) Uani 1 1 d . . . H11 H 0.4002 0.4572 0.7129 0.026(5) Uiso 1 1 calc R . . C12 C 0.5385(2) 0.33479(19) 0.72353(17) 0.0271(4) Uani 1 1 d . . . H12 H 0.5703 0.3587 0.8095 0.027(6) Uiso 1 1 calc R . . C13 C 0.59186(19) 0.24344(18) 0.65657(17) 0.0252(4) Uani 1 1 d . . . H13 H 0.6599 0.2028 0.6960 0.027(6) Uiso 1 1 calc R . . C14 C 0.54519(17) 0.20971(16) 0.52813(16) 0.0208(3) Uani 1 1 d . . . C15 C 0.59381(19) 0.11842(17) 0.44805(18) 0.0251(4) Uani 1 1 d . . . H15 H 0.6642 0.0754 0.4794 0.027(6) Uiso 1 1 calc R . . C16 C 0.5392(2) 0.09237(18) 0.32555(18) 0.0266(4) Uani 1 1 d . . . H16 H 0.5717 0.0304 0.2727 0.028(6) Uiso 1 1 calc R . . C17 C 0.43550(19) 0.15559(18) 0.27591(17) 0.0250(4) Uani 1 1 d . . . H17 H 0.3988 0.1351 0.1906 0.031(6) Uiso 1 1 calc R . . C18 C 0.38688(18) 0.24687(16) 0.34987(16) 0.0204(3) Uani 1 1 d . . . C19 C 0.44212(17) 0.27237(16) 0.47573(15) 0.0184(3) Uani 1 1 d . . . O1 O 0.21353(13) 0.56376(12) 0.61164(11) 0.0217(2) Uani 1 1 d . . . O2 O 0.10053(13) 0.72284(12) 0.66225(11) 0.0215(2) Uani 1 1 d . . . O3 O 0.00873(13) 0.33520(12) 0.14463(11) 0.0218(2) Uani 1 1 d . . . H3 H -0.0213 0.3287 0.2135 0.054(8) Uiso 1 1 calc R . . O4 O 0.15883(14) 0.47812(13) 0.06620(11) 0.0263(3) Uani 1 1 d . . . N2 N 0.11720(14) 0.55279(13) 0.36700(12) 0.0162(2) Uani 1 1 d . A . C21 C 0.14017(17) 0.64570(16) 0.58544(15) 0.0182(3) Uani 1 1 d . . . C22 C 0.09384(16) 0.64997(15) 0.44917(15) 0.0171(3) Uani 1 1 d . . . C23 C 0.02942(17) 0.74870(16) 0.41382(15) 0.0194(3) Uani 1 1 d . A . H23 H 0.0126 0.8122 0.4756 0.019(5) Uiso 1 1 calc R . . C24 C -0.01133(18) 0.75648(16) 0.28868(16) 0.0204(3) Uani 1 1 d . . . C25 C 0.01091(18) 0.65565(17) 0.20537(15) 0.0214(3) Uani 1 1 d . A . H25 H -0.0161 0.6546 0.1190 0.025(5) Uiso 1 1 calc R . . C26 C 0.07189(17) 0.55668(16) 0.24666(15) 0.0182(3) Uani 1 1 d . . . C27 C 0.08620(18) 0.45138(16) 0.14662(15) 0.0195(3) Uani 1 1 d . A . C28 C -0.0697(2) 0.87054(18) 0.24455(18) 0.0266(4) Uani 0.820(14) 1 d PD A 1 C29 C -0.1577(5) 0.9221(5) 0.3383(3) 0.0342(8) Uani 0.820(14) 1 d PD A 1 H29A H -0.1856 1.0009 0.3126 0.051 Uiso 0.820(14) 1 calc PR A 1 H29B H -0.1029 0.9425 0.4206 0.051 Uiso 0.820(14) 1 calc PR A 1 H29C H -0.2410 0.8558 0.3416 0.051 Uiso 0.820(14) 1 calc PR A 1 C30 C 0.0548(4) 0.9795(4) 0.2376(8) 0.0745(19) Uani 0.820(14) 1 d PD A 1 H30A H 0.1045 0.9548 0.1685 0.112 Uiso 0.820(14) 1 calc PR A 1 H30B H 0.1178 0.9936 0.3156 0.112 Uiso 0.820(14) 1 calc PR A 1 H30C H 0.0218 1.0597 0.2242 0.112 Uiso 0.820(14) 1 calc PR A 1 C31 C -0.1633(6) 0.8326(6) 0.1203(4) 0.0719(17) Uani 0.820(14) 1 d PD A 1 H31A H -0.1070 0.8473 0.0522 0.108 Uiso 0.820(14) 1 calc PR A 1 H31B H -0.2349 0.8858 0.1164 0.108 Uiso 0.820(14) 1 calc PR A 1 H31C H -0.2079 0.7405 0.1127 0.108 Uiso 0.820(14) 1 calc PR A 1 C28A C -0.0697(2) 0.87054(18) 0.24455(18) 0.0266(4) Uani 0.180(14) 1 d PD A 2 C29A C -0.119(2) 0.9596(16) 0.3409(13) 0.0342(8) Uani 0.180(14) 1 d PD A 2 H29D H -0.1536 0.9097 0.4063 0.051 Uiso 0.180(14) 1 calc PR A 2 H29E H -0.1942 0.9965 0.3013 0.051 Uiso 0.180(14) 1 calc PR A 2 H29F H -0.0414 1.0300 0.3774 0.051 Uiso 0.180(14) 1 calc PR A 2 C30A C 0.047(2) 0.949(2) 0.186(3) 0.0745(19) Uani 0.180(14) 1 d PD A 2 H30D H 0.1364 0.9271 0.2155 0.112 Uiso 0.180(14) 1 calc PR A 2 H30E H 0.0517 1.0423 0.2083 0.112 Uiso 0.180(14) 1 calc PR A 2 H30F H 0.0294 0.9285 0.0949 0.112 Uiso 0.180(14) 1 calc PR A 2 C31A C -0.1943(19) 0.810(2) 0.147(2) 0.0719(17) Uani 0.180(14) 1 d PD A 2 H31D H -0.1801 0.7265 0.1077 0.108 Uiso 0.180(14) 1 calc PR A 2 H31E H -0.2034 0.8687 0.0840 0.108 Uiso 0.180(14) 1 calc PR A 2 H31F H -0.2794 0.7957 0.1874 0.108 Uiso 0.180(14) 1 calc PR A 2 C1 C 0.3252(2) 0.7045(2) 0.9200(2) 0.0343(4) Uani 1 1 d . . . H1A H 0.3005 0.7094 0.8304 0.049(8) Uiso 1 1 calc R . . H1B H 0.2472 0.6461 0.9486 0.050(8) Uiso 1 1 calc R . . Cl1 Cl 0.47693(6) 0.63945(6) 0.94085(5) 0.04269(13) Uani 1 1 d . . . Cl2 Cl 0.34858(9) 0.86023(7) 1.00256(7) 0.06165(19) 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 Pd1 0.01675(6) 0.01678(6) 0.01496(6) 0.00032(4) 0.00242(4) 0.00525(4) N1 0.0185(7) 0.0185(6) 0.0193(6) 0.0019(5) 0.0021(5) 0.0041(5) C10 0.0261(9) 0.0267(9) 0.0187(8) -0.0031(6) 0.0002(6) 0.0126(7) C11 0.0254(9) 0.0255(9) 0.0204(8) 0.0012(6) 0.0013(6) 0.0064(7) C12 0.0281(9) 0.0321(10) 0.0208(8) 0.0048(7) -0.0015(7) 0.0070(7) C13 0.0207(8) 0.0275(9) 0.0284(9) 0.0100(7) 0.0002(7) 0.0051(7) C14 0.0170(8) 0.0196(8) 0.0268(8) 0.0070(6) 0.0037(6) 0.0035(6) C15 0.0213(8) 0.0227(8) 0.0346(10) 0.0080(7) 0.0074(7) 0.0087(6) C16 0.0276(9) 0.0225(8) 0.0333(10) 0.0028(7) 0.0110(7) 0.0107(7) C17 0.0264(9) 0.0254(9) 0.0246(8) 0.0006(7) 0.0060(7) 0.0087(7) C18 0.0204(8) 0.0199(8) 0.0212(8) 0.0010(6) 0.0036(6) 0.0053(6) C19 0.0166(7) 0.0173(7) 0.0216(8) 0.0031(6) 0.0039(6) 0.0032(6) O1 0.0265(6) 0.0235(6) 0.0163(5) 0.0001(4) 0.0022(4) 0.0099(5) O2 0.0268(6) 0.0205(6) 0.0176(5) -0.0019(4) 0.0058(5) 0.0061(5) O3 0.0262(6) 0.0222(6) 0.0163(5) -0.0029(4) 0.0035(5) 0.0051(5) O4 0.0325(7) 0.0287(7) 0.0191(6) 0.0017(5) 0.0085(5) 0.0079(5) N2 0.0156(6) 0.0165(6) 0.0164(6) -0.0002(5) 0.0030(5) 0.0033(5) C21 0.0177(7) 0.0178(7) 0.0175(7) -0.0004(6) 0.0035(6) 0.0001(6) C22 0.0164(7) 0.0169(7) 0.0173(7) -0.0007(6) 0.0030(5) 0.0028(5) C23 0.0203(8) 0.0175(7) 0.0200(7) -0.0024(6) 0.0024(6) 0.0054(6) C24 0.0202(8) 0.0189(8) 0.0226(8) 0.0013(6) 0.0014(6) 0.0063(6) C25 0.0255(8) 0.0218(8) 0.0168(7) 0.0006(6) -0.0007(6) 0.0069(6) C26 0.0186(7) 0.0186(7) 0.0168(7) -0.0010(6) 0.0023(6) 0.0040(6) C27 0.0233(8) 0.0217(8) 0.0143(7) -0.0003(6) -0.0001(6) 0.0094(6) C28 0.0312(10) 0.0227(8) 0.0288(9) 0.0043(7) 0.0023(7) 0.0128(7) C29 0.042(2) 0.0261(18) 0.0388(12) 0.0037(12) 0.0052(13) 0.0180(15) C30 0.0532(19) 0.039(2) 0.154(6) 0.051(3) 0.051(3) 0.0245(16) C31 0.131(4) 0.064(3) 0.0296(19) -0.0093(19) -0.030(2) 0.072(3) C28A 0.0312(10) 0.0227(8) 0.0288(9) 0.0043(7) 0.0023(7) 0.0128(7) C29A 0.042(2) 0.0261(18) 0.0388(12) 0.0037(12) 0.0052(13) 0.0180(15) C30A 0.0532(19) 0.039(2) 0.154(6) 0.051(3) 0.051(3) 0.0245(16) C31A 0.131(4) 0.064(3) 0.0296(19) -0.0093(19) -0.030(2) 0.072(3) C1 0.0319(11) 0.0395(11) 0.0306(10) 0.0083(8) 0.0006(8) 0.0043(9) Cl1 0.0515(3) 0.0547(3) 0.0289(2) 0.0089(2) 0.0077(2) 0.0250(3) Cl2 0.0823(5) 0.0467(4) 0.0599(4) -0.0020(3) 0.0083(4) 0.0279(4) _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 Pd1 N1 2.0027(14) . ? Pd1 C10 2.0220(16) . ? Pd1 N2 2.0848(13) . ? Pd1 O1 2.1319(12) . ? N1 C11 1.324(2) . ? N1 C19 1.378(2) . ? C10 C18 1.503(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.409(2) . ? C11 H11 0.9500 . ? C12 C13 1.366(3) . ? C12 H12 0.9500 . ? C13 C14 1.416(3) . ? C13 H13 0.9500 . ? C14 C19 1.414(2) . ? C14 C15 1.417(2) . ? C15 C16 1.368(3) . ? C15 H15 0.9500 . ? C16 C17 1.411(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(2) . ? C17 H17 0.9500 . ? C18 C19 1.402(2) . ? O1 C21 1.261(2) . ? O2 C21 1.2510(19) . ? O3 C27 1.314(2) . ? O3 H3 0.8400 . ? O4 C27 1.211(2) . ? N2 C26 1.348(2) . ? N2 C22 1.361(2) . ? C21 C22 1.516(2) . ? C22 C23 1.382(2) . ? C23 C24 1.397(2) . ? C23 H23 0.9500 . ? C24 C25 1.392(2) . ? C24 C28 1.525(2) . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 C27 1.513(2) . ? C28 C31 1.529(3) . ? C28 C30 1.530(4) . ? C28 C29 1.530(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 0.9800 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C1 Cl2 1.754(2) . ? C1 Cl1 1.761(2) . ? C1 H1A 0.9900 . ? C1 H1B 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 Pd1 C10 82.90(6) . . ? N1 Pd1 N2 172.51(5) . . ? C10 Pd1 N2 102.15(6) . . ? N1 Pd1 O1 94.89(5) . . ? C10 Pd1 O1 176.45(6) . . ? N2 Pd1 O1 80.33(5) . . ? C11 N1 C19 119.12(15) . . ? C11 N1 Pd1 125.16(12) . . ? C19 N1 Pd1 115.66(11) . . ? C18 C10 Pd1 109.59(11) . . ? C18 C10 H10A 109.8 . . ? Pd1 C10 H10A 109.8 . . ? C18 C10 H10B 109.8 . . ? Pd1 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C12 121.96(17) . . ? N1 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? C13 C12 C11 120.04(17) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.63(16) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C19 C14 C13 117.30(16) . . ? C19 C14 C15 117.52(16) . . ? C13 C14 C15 125.18(16) . . ? C16 C15 C14 119.87(16) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.42(16) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 120.72(17) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 117.70(16) . . ? C17 C18 C10 125.79(16) . . ? C19 C18 C10 116.50(14) . . ? N1 C19 C18 115.30(14) . . ? N1 C19 C14 121.94(15) . . ? C18 C19 C14 122.75(15) . . ? C21 O1 Pd1 113.37(10) . . ? C27 O3 H3 109.5 . . ? C26 N2 C22 115.93(14) . . ? C26 N2 Pd1 132.14(11) . . ? C22 N2 Pd1 110.98(10) . . ? O2 C21 O1 125.70(15) . . ? O2 C21 C22 116.97(15) . . ? O1 C21 C22 117.32(14) . . ? N2 C22 C23 123.17(15) . . ? N2 C22 C21 116.96(14) . . ? C23 C22 C21 119.87(14) . . ? C22 C23 C24 120.96(15) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 115.48(15) . . ? C25 C24 C28 121.70(15) . . ? C23 C24 C28 122.75(15) . . ? C26 C25 C24 120.95(15) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? N2 C26 C25 123.39(15) . . ? N2 C26 C27 121.17(14) . . ? C25 C26 C27 115.43(14) . . ? O4 C27 O3 122.08(15) . . ? O4 C27 C26 119.89(16) . . ? O3 C27 C26 117.77(14) . . ? C24 C28 C31 112.2(2) . . ? C24 C28 C30 107.0(2) . . ? C31 C28 C30 112.0(3) . . ? C24 C28 C29 110.9(2) . . ? C31 C28 C29 107.0(2) . . ? C30 C28 C29 107.6(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? H29D C29A H29E 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? H30D C30A H30E 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? Cl2 C1 Cl1 111.39(12) . . ? Cl2 C1 H1A 109.3 . . ? Cl1 C1 H1A 109.3 . . ? Cl2 C1 H1B 109.3 . . ? Cl1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? 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 C10 Pd1 N1 C11 179.18(16) . . . . ? O1 Pd1 N1 C11 -3.61(15) . . . . ? C10 Pd1 N1 C19 2.10(12) . . . . ? O1 Pd1 N1 C19 179.31(11) . . . . ? N1 Pd1 C10 C18 -1.58(12) . . . . ? N2 Pd1 C10 C18 172.81(12) . . . . ? C19 N1 C11 C12 -1.0(3) . . . . ? Pd1 N1 C11 C12 -177.97(13) . . . . ? N1 C11 C12 C13 0.2(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C19 -1.0(3) . . . . ? C12 C13 C14 C15 178.87(17) . . . . ? C19 C14 C15 C16 -1.1(3) . . . . ? C13 C14 C15 C16 179.02(17) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C19 -1.2(3) . . . . ? C16 C17 C18 C10 178.99(17) . . . . ? Pd1 C10 C18 C17 -179.17(15) . . . . ? Pd1 C10 C18 C19 1.0(2) . . . . ? C11 N1 C19 C18 -179.36(16) . . . . ? Pd1 N1 C19 C18 -2.09(19) . . . . ? C11 N1 C19 C14 0.8(2) . . . . ? Pd1 N1 C19 C14 178.07(12) . . . . ? C17 C18 C19 N1 -179.18(15) . . . . ? C10 C18 C19 N1 0.7(2) . . . . ? C17 C18 C19 C14 0.7(3) . . . . ? C10 C18 C19 C14 -179.49(16) . . . . ? C13 C14 C19 N1 0.2(2) . . . . ? C15 C14 C19 N1 -179.69(15) . . . . ? C13 C14 C19 C18 -179.65(16) . . . . ? C15 C14 C19 C18 0.5(2) . . . . ? N1 Pd1 O1 C21 171.09(12) . . . . ? N2 Pd1 O1 C21 -3.10(11) . . . . ? C10 Pd1 N2 C26 -6.58(16) . . . . ? O1 Pd1 N2 C26 176.01(15) . . . . ? C10 Pd1 N2 C22 -174.68(11) . . . . ? O1 Pd1 N2 C22 7.91(10) . . . . ? Pd1 O1 C21 O2 176.89(13) . . . . ? Pd1 O1 C21 C22 -2.08(18) . . . . ? C26 N2 C22 C23 -0.8(2) . . . . ? Pd1 N2 C22 C23 169.43(13) . . . . ? C26 N2 C22 C21 178.34(14) . . . . ? Pd1 N2 C22 C21 -11.45(17) . . . . ? O2 C21 C22 N2 -169.58(14) . . . . ? O1 C21 C22 N2 9.5(2) . . . . ? O2 C21 C22 C23 9.6(2) . . . . ? O1 C21 C22 C23 -171.36(15) . . . . ? N2 C22 C23 C24 -2.4(3) . . . . ? C21 C22 C23 C24 178.52(15) . . . . ? C22 C23 C24 C25 3.2(2) . . . . ? C22 C23 C24 C28 -173.88(16) . . . . ? C23 C24 C25 C26 -1.0(3) . . . . ? C28 C24 C25 C26 176.05(17) . . . . ? C22 N2 C26 C25 3.0(2) . . . . ? Pd1 N2 C26 C25 -164.60(13) . . . . ? C22 N2 C26 C27 -177.50(14) . . . . ? Pd1 N2 C26 C27 14.9(2) . . . . ? C24 C25 C26 N2 -2.2(3) . . . . ? C24 C25 C26 C27 178.35(16) . . . . ? N2 C26 C27 O4 -116.37(18) . . . . ? C25 C26 C27 O4 63.1(2) . . . . ? N2 C26 C27 O3 69.4(2) . . . . ? C25 C26 C27 O3 -111.10(18) . . . . ? C25 C24 C28 C31 28.5(4) . . . . ? C23 C24 C28 C31 -154.6(3) . . . . ? C25 C24 C28 C30 -94.8(4) . . . . ? C23 C24 C28 C30 82.1(4) . . . . ? C25 C24 C28 C29 148.1(3) . . . . ? C23 C24 C28 C29 -35.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.84 1.72 2.5412(17) 165.9 2_566 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.691 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.073 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 -0.0037118 _diffrn_orient_matrix_UB_12 0.0943382 _diffrn_orient_matrix_UB_13 0.0021909 _diffrn_orient_matrix_UB_21 0.0011757 _diffrn_orient_matrix_UB_22 -0.0066522 _diffrn_orient_matrix_UB_23 -0.0919907 _diffrn_orient_matrix_UB_31 -0.1040649 _diffrn_orient_matrix_UB_32 -0.0228229 _diffrn_orient_matrix_UB_33 -0.0128651 _symmetry_space_group_name_Hall '-P 1' _exptl_crystal_id 'Vedern/JZhang jz-540a #2 @150K' _diffrn_measurement_frame_width-CCD 0.3 _diffrn_measurement_details 610,610,610,1200,1200 _diffrn_measurement_total_frames-CCD 4230 _diffrn_measurement_frame_time-CCD 10 _diffrn_measurement_total_time-CCD 18.8 _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_detector_distance-CCD 5.2 _diffrn_measurement_frame_size-CCD 512 _diffrn_measurement_specimen_support 'glass capillary' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ;