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 'Prasenjit Ghosh' _publ_contact_author_address ; Deaprtment of Chemistry Indian Institute of Technology Bombay Powai Mumbai Maharastra 400076 INDIA ; _publ_contact_author_email PGHOSH@CHEM.IITB.AC.IN _publ_section_title ; Air-Stable, Convenient to Handle Pd Based PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) Themed Precatalysts of N/O-Functionalized N-Heterocyclic Carbenes and its Utility in Suzuki-Miyaura Cross-Coupling Reaction ; loop_ _publ_author_name 'Prasenjit Ghosh' 'Lipika Ray' 'Mobin M. Shaikh' data_pg058 _database_code_depnum_ccdc_archive 'CCDC 623095' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 Br2 N3 O Pd' _chemical_formula_weight 589.65 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' Br Br -0.2901 2.4595 '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' 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 12.9252(3) _cell_length_b 10.8313(3) _cell_length_c 16.0613(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.569(2) _cell_angle_gamma 90.00 _cell_volume 2194.64(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11110 _cell_measurement_theta_min 3.2012 _cell_measurement_theta_max 32.1955 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 4.501 _exptl_absorpt_correction_T_min 0.3018 _exptl_absorpt_correction_T_max 0.3655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15160 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3840 _reflns_number_gt 3024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.1298P)^2^+18.3588P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3840 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.2319 _refine_ls_wR_factor_gt 0.2190 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _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 Pd1 Pd 0.27053(5) 0.07651(6) 0.08143(4) 0.0279(3) Uani 1 1 d . . . Br1 Br 0.40549(10) 0.20422(14) 0.04456(8) 0.0621(4) Uani 1 1 d . . . Br2 Br 0.13629(11) -0.03616(12) 0.13075(9) 0.0619(4) Uani 1 1 d . . . O1 O 0.2047(6) 0.5421(8) 0.0613(5) 0.0518(19) Uani 1 1 d . . . N1 N 0.3428(6) 0.1675(7) 0.2644(5) 0.0322(16) Uani 1 1 d . . . N2 N 0.2213(6) 0.2769(7) 0.1846(4) 0.0331(17) Uani 1 1 d . . . N3 N 0.2475(6) -0.0253(7) -0.0324(5) 0.0307(16) Uani 1 1 d . . . C1 C 0.2826(6) 0.1771(8) 0.1840(5) 0.0293(18) Uani 1 1 d . . . C2 C 0.3157(8) 0.2657(9) 0.3127(6) 0.039(2) Uani 1 1 d . . . H2 H 0.3448 0.2813 0.3699 0.047 Uiso 1 1 calc R . . C3 C 0.2425(9) 0.3311(8) 0.2632(6) 0.041(2) Uani 1 1 d . . . H3 H 0.2105 0.4019 0.2787 0.050 Uiso 1 1 calc R . . C4 C 0.4244(7) 0.0730(9) 0.3016(6) 0.036(2) Uani 1 1 d . . . C5 C 0.4409(13) -0.0226(14) 0.2371(8) 0.076(5) Uani 1 1 d . . . H5A H 0.3771 -0.0699 0.2190 0.114 Uiso 1 1 calc R . . H5B H 0.4980 -0.0765 0.2626 0.114 Uiso 1 1 calc R . . H5C H 0.4580 0.0180 0.1887 0.114 Uiso 1 1 calc R . . C6 C 0.3876(12) 0.0145(13) 0.3740(9) 0.069(4) Uani 1 1 d . . . H6A H 0.3750 0.0773 0.4128 0.104 Uiso 1 1 calc R . . H6B H 0.4410 -0.0414 0.4033 0.104 Uiso 1 1 calc R . . H6C H 0.3232 -0.0302 0.3525 0.104 Uiso 1 1 calc R . . C7 C 0.5289(10) 0.1384(15) 0.3346(12) 0.084(5) Uani 1 1 d . . . H7A H 0.5389 0.2006 0.2946 0.127 Uiso 1 1 calc R . . H7B H 0.5858 0.0797 0.3418 0.127 Uiso 1 1 calc R . . H7C H 0.5282 0.1763 0.3885 0.127 Uiso 1 1 calc R . . C8 C 0.1381(9) 0.3150(9) 0.1078(7) 0.048(3) Uani 1 1 d . . . H8A H 0.1715 0.3246 0.0596 0.057 Uiso 1 1 calc R . . H8B H 0.0861 0.2494 0.0941 0.057 Uiso 1 1 calc R . . C9 C 0.0825(9) 0.4313(9) 0.1194(6) 0.042(2) Uani 1 1 d . . . C10 C 0.1117(8) 0.5437(9) 0.0912(6) 0.037(2) Uani 1 1 d . . . C11 C 0.2336(11) 0.6517(14) 0.0237(8) 0.065(3) Uani 1 1 d . . . H11A H 0.1757 0.6783 -0.0208 0.097 Uiso 1 1 calc R . . H11B H 0.2946 0.6360 0.0002 0.097 Uiso 1 1 calc R . . H11C H 0.2501 0.7151 0.0664 0.097 Uiso 1 1 calc R . . C12 C 0.0539(8) 0.6490(10) 0.0942(6) 0.042(2) Uani 1 1 d . . . H12 H 0.0745 0.7236 0.0741 0.050 Uiso 1 1 calc R . . C13 C -0.0358(9) 0.6416(14) 0.1277(8) 0.061(3) Uani 1 1 d . . . H13 H -0.0756 0.7127 0.1295 0.073 Uiso 1 1 calc R . . C14 C -0.0678(10) 0.5351(15) 0.1582(8) 0.064(4) Uani 1 1 d . . . H14 H -0.1277 0.5321 0.1815 0.077 Uiso 1 1 calc R . . C15 C -0.0087(9) 0.4324(12) 0.1532(8) 0.056(3) Uani 1 1 d . . . H15 H -0.0301 0.3583 0.1735 0.067 Uiso 1 1 calc R . . C16 C 0.1490(8) -0.0395(9) -0.0797(6) 0.036(2) Uani 1 1 d . . . H16 H 0.0925 -0.0028 -0.0618 0.043 Uiso 1 1 calc R . . C17 C 0.1293(8) -0.1086(9) -0.1556(6) 0.038(2) Uani 1 1 d . . . H17 H 0.0609 -0.1145 -0.1888 0.046 Uiso 1 1 calc R . . C18 C 0.2106(9) -0.1667(9) -0.1800(6) 0.042(2) Uani 1 1 d . . . H18 H 0.1982 -0.2160 -0.2286 0.050 Uiso 1 1 calc R . . C19 C 0.3119(8) -0.1517(9) -0.1320(6) 0.040(2) Uani 1 1 d . . . H19 H 0.3692 -0.1889 -0.1484 0.048 Uiso 1 1 calc R . . C20 C 0.3273(8) -0.0804(9) -0.0587(6) 0.039(2) Uani 1 1 d . . . H20 H 0.3958 -0.0705 -0.0265 0.047 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 Pd1 0.0317(4) 0.0272(4) 0.0242(4) -0.0036(3) 0.0050(3) -0.0028(3) Br1 0.0615(8) 0.0752(9) 0.0492(7) -0.0008(6) 0.0110(6) -0.0177(6) Br2 0.0666(8) 0.0553(8) 0.0699(9) -0.0132(6) 0.0281(6) -0.0119(6) O1 0.053(4) 0.058(5) 0.046(4) 0.005(4) 0.013(3) 0.008(4) N1 0.038(4) 0.031(4) 0.024(4) 0.000(3) 0.000(3) 0.004(3) N2 0.049(4) 0.027(4) 0.019(3) 0.000(3) -0.001(3) 0.001(3) N3 0.031(4) 0.032(4) 0.030(4) -0.002(3) 0.008(3) -0.004(3) C1 0.030(4) 0.027(4) 0.030(4) 0.003(4) 0.005(3) -0.001(3) C2 0.057(6) 0.031(5) 0.025(4) -0.008(4) 0.001(4) 0.007(4) C3 0.067(6) 0.021(4) 0.029(5) -0.006(4) -0.004(4) 0.014(4) C4 0.038(5) 0.036(5) 0.031(5) -0.002(4) 0.003(4) 0.008(4) C5 0.103(11) 0.073(9) 0.045(7) -0.008(6) 0.000(7) 0.060(9) C6 0.096(10) 0.055(8) 0.060(8) 0.029(7) 0.026(7) 0.035(7) C7 0.041(6) 0.075(10) 0.130(14) 0.000(10) 0.001(7) 0.007(7) C8 0.070(7) 0.024(5) 0.035(5) -0.006(4) -0.020(5) 0.015(5) C9 0.058(6) 0.030(5) 0.027(5) 0.000(4) -0.012(4) 0.002(4) C10 0.051(5) 0.029(5) 0.024(4) 0.001(4) -0.006(4) 0.009(4) C11 0.069(8) 0.075(9) 0.051(7) 0.014(7) 0.016(6) -0.014(7) C12 0.053(6) 0.032(5) 0.035(5) 0.002(4) -0.001(4) 0.008(4) C13 0.052(7) 0.074(9) 0.049(6) -0.009(6) -0.006(5) 0.027(6) C14 0.044(6) 0.096(11) 0.047(7) 0.004(7) 0.001(5) -0.016(7) C15 0.046(6) 0.064(8) 0.051(7) 0.006(6) -0.005(5) -0.017(6) C16 0.040(5) 0.031(5) 0.034(5) 0.000(4) 0.005(4) -0.005(4) C17 0.049(6) 0.037(5) 0.027(4) 0.002(4) 0.003(4) -0.011(4) C18 0.067(7) 0.031(5) 0.029(5) -0.008(4) 0.016(5) -0.011(5) C19 0.056(6) 0.033(5) 0.032(5) -0.008(4) 0.014(4) -0.001(4) C20 0.041(5) 0.041(5) 0.034(5) 0.000(4) 0.008(4) -0.005(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 C1 1.953(9) . ? Pd1 N3 2.100(7) . ? Pd1 Br2 2.3929(13) . ? Pd1 Br1 2.3993(13) . ? O1 C10 1.388(13) . ? O1 C11 1.418(15) . ? N1 C1 1.359(11) . ? N1 C2 1.404(12) . ? N1 C4 1.498(12) . ? N2 C1 1.341(12) . ? N2 C3 1.365(12) . ? N2 C8 1.506(11) . ? N3 C20 1.337(13) . ? N3 C16 1.342(12) . ? C2 C3 1.304(14) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C6 1.490(16) . ? C4 C5 1.512(15) . ? C4 C7 1.515(17) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.482(14) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.380(15) . ? C9 C15 1.401(17) . ? C10 C12 1.369(14) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.382(17) . ? C12 H12 0.9300 . ? C13 C14 1.35(2) . ? C13 H13 0.9300 . ? C14 C15 1.36(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.406(14) . ? C16 H16 0.9300 . ? C17 C18 1.354(15) . ? C17 H17 0.9300 . ? C18 C19 1.378(15) . ? C18 H18 0.9300 . ? C19 C20 1.385(14) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 Pd1 N3 176.0(3) . . ? C1 Pd1 Br2 86.3(2) . . ? N3 Pd1 Br2 92.58(19) . . ? C1 Pd1 Br1 87.6(2) . . ? N3 Pd1 Br1 93.5(2) . . ? Br2 Pd1 Br1 173.87(5) . . ? C10 O1 C11 117.7(9) . . ? C1 N1 C2 107.9(7) . . ? C1 N1 C4 129.7(8) . . ? C2 N1 C4 122.4(7) . . ? C1 N2 C3 110.6(7) . . ? C1 N2 C8 122.2(7) . . ? C3 N2 C8 127.1(8) . . ? C20 N3 C16 118.2(8) . . ? C20 N3 Pd1 122.4(6) . . ? C16 N3 Pd1 119.3(6) . . ? N2 C1 N1 105.8(8) . . ? N2 C1 Pd1 121.1(6) . . ? N1 C1 Pd1 133.1(7) . . ? C3 C2 N1 108.0(8) . . ? C3 C2 H2 126.0 . . ? N1 C2 H2 126.0 . . ? C2 C3 N2 107.7(8) . . ? C2 C3 H3 126.2 . . ? N2 C3 H3 126.2 . . ? C6 C4 N1 106.6(8) . . ? C6 C4 C5 111.1(11) . . ? N1 C4 C5 112.7(8) . . ? C6 C4 C7 109.7(12) . . ? N1 C4 C7 108.5(9) . . ? C5 C4 C7 108.2(11) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 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 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 N2 114.1(8) . . ? C9 C8 H8A 108.7 . . ? N2 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? N2 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C15 115.7(10) . . ? C10 C9 C8 122.3(11) . . ? C15 C9 C8 121.8(11) . . ? C12 C10 C9 122.2(11) . . ? C12 C10 O1 122.9(10) . . ? C9 C10 O1 114.9(9) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 C13 118.4(11) . . ? C10 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 122.6(12) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C13 C14 C15 117.1(12) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? C14 C15 C9 124.0(12) . . ? C14 C15 H15 118.0 . . ? C9 C15 H15 118.0 . . ? N3 C16 C17 121.5(9) . . ? N3 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 119.6(9) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 119.1(9) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 119.0(9) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? N3 C20 C19 122.7(9) . . ? N3 C20 H20 118.7 . . ? C19 C20 H20 118.7 . . ? 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 C1 Pd1 N3 C20 158(4) . . . . ? Br2 Pd1 N3 C20 -127.8(7) . . . . ? Br1 Pd1 N3 C20 53.2(7) . . . . ? C1 Pd1 N3 C16 -24(5) . . . . ? Br2 Pd1 N3 C16 49.9(7) . . . . ? Br1 Pd1 N3 C16 -129.1(7) . . . . ? C3 N2 C1 N1 0.7(11) . . . . ? C8 N2 C1 N1 -176.5(9) . . . . ? C3 N2 C1 Pd1 179.0(7) . . . . ? C8 N2 C1 Pd1 1.8(12) . . . . ? C2 N1 C1 N2 -0.4(10) . . . . ? C4 N1 C1 N2 179.0(8) . . . . ? C2 N1 C1 Pd1 -178.4(7) . . . . ? C4 N1 C1 Pd1 1.0(15) . . . . ? N3 Pd1 C1 N2 -14(5) . . . . ? Br2 Pd1 C1 N2 -88.0(7) . . . . ? Br1 Pd1 C1 N2 91.4(7) . . . . ? N3 Pd1 C1 N1 164(4) . . . . ? Br2 Pd1 C1 N1 89.7(8) . . . . ? Br1 Pd1 C1 N1 -90.8(8) . . . . ? C1 N1 C2 C3 -0.1(12) . . . . ? C4 N1 C2 C3 -179.6(9) . . . . ? N1 C2 C3 N2 0.5(12) . . . . ? C1 N2 C3 C2 -0.8(12) . . . . ? C8 N2 C3 C2 176.3(10) . . . . ? C1 N1 C4 C6 -120.8(11) . . . . ? C2 N1 C4 C6 58.6(13) . . . . ? C1 N1 C4 C5 1.3(15) . . . . ? C2 N1 C4 C5 -179.3(11) . . . . ? C1 N1 C4 C7 121.1(12) . . . . ? C2 N1 C4 C7 -59.5(13) . . . . ? C1 N2 C8 C9 -176.9(9) . . . . ? C3 N2 C8 C9 6.3(16) . . . . ? N2 C8 C9 C10 97.1(12) . . . . ? N2 C8 C9 C15 -88.5(13) . . . . ? C15 C9 C10 C12 -1.4(14) . . . . ? C8 C9 C10 C12 173.3(9) . . . . ? C15 C9 C10 O1 177.4(8) . . . . ? C8 C9 C10 O1 -7.9(13) . . . . ? C11 O1 C10 C12 -7.2(14) . . . . ? C11 O1 C10 C9 174.0(9) . . . . ? C9 C10 C12 C13 0.8(15) . . . . ? O1 C10 C12 C13 -177.9(9) . . . . ? C10 C12 C13 C14 0.5(17) . . . . ? C12 C13 C14 C15 -1.2(18) . . . . ? C13 C14 C15 C9 0.5(18) . . . . ? C10 C9 C15 C14 0.8(16) . . . . ? C8 C9 C15 C14 -174.0(10) . . . . ? C20 N3 C16 C17 -1.0(13) . . . . ? Pd1 N3 C16 C17 -178.8(7) . . . . ? N3 C16 C17 C18 2.8(14) . . . . ? C16 C17 C18 C19 -3.1(14) . . . . ? C17 C18 C19 C20 1.8(15) . . . . ? C16 N3 C20 C19 -0.4(14) . . . . ? Pd1 N3 C20 C19 177.3(7) . . . . ? C18 C19 C20 N3 0.1(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.825 _refine_diff_density_min -2.134 _refine_diff_density_rms 0.213 # Attachment 'pg059.cif' data_pg059 _database_code_depnum_ccdc_archive 'CCDC 623546' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Cl N3 O' _chemical_formula_weight 307.82 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0741(3) _cell_length_b 10.996(3) _cell_length_c 12.313(4) _cell_angle_alpha 82.75(2) _cell_angle_beta 83.452(14) _cell_angle_gamma 81.642(13) _cell_volume 803.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4690 _cell_measurement_theta_min 3.3472 _cell_measurement_theta_max 29.9972 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_min 0.9248 _exptl_absorpt_correction_T_max 0.9356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6529 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2819 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0569P)^2^+0.2414P] 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 2819 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _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 Cl1 Cl 0.41260(8) 0.60531(5) 0.80219(4) 0.03027(19) Uani 1 1 d . . . O1 O 0.8526(2) 0.94171(13) 0.89632(12) 0.0296(4) Uani 1 1 d . . . N1 N 1.0366(3) 0.62286(15) 1.17009(13) 0.0224(4) Uani 1 1 d . . . N2 N 0.9577(3) 0.70430(16) 1.00788(14) 0.0230(4) Uani 1 1 d . . . N3 N 0.5979(3) 0.86900(17) 0.80644(14) 0.0237(4) Uani 1 1 d . . . C1 C 0.9043(3) 0.62144(18) 1.09153(16) 0.0215(4) Uani 1 1 d . . . H1 H 0.7931 0.5709 1.0945 0.026 Uiso 1 1 calc R . . C2 C 1.1794(4) 0.7095(2) 1.13499(18) 0.0289(5) Uani 1 1 d . . . H2 H 1.2894 0.7291 1.1740 0.035 Uiso 1 1 calc R . . C3 C 1.1304(3) 0.7605(2) 1.03394(18) 0.0289(5) Uani 1 1 d . . . H3 H 1.1999 0.8220 0.9901 0.035 Uiso 1 1 calc R . . C4 C 1.0389(3) 0.53917(19) 1.27434(16) 0.0248(5) Uani 1 1 d . . . H4A H 1.1711 0.4781 1.2705 0.030 Uiso 1 1 calc R . . H4B H 0.9088 0.4957 1.2836 0.030 Uiso 1 1 calc R . . C5 C 1.0379(3) 0.60865(18) 1.37225(16) 0.0232(4) Uani 1 1 d . . . C6 C 0.8434(4) 0.6775(2) 1.41339(18) 0.0297(5) Uani 1 1 d . . . H6 H 0.7135 0.6828 1.3787 0.036 Uiso 1 1 calc R . . C7 C 0.8405(4) 0.7384(2) 1.50547(19) 0.0348(5) Uani 1 1 d . . . H7 H 0.7097 0.7849 1.5321 0.042 Uiso 1 1 calc R . . C8 C 1.0326(4) 0.7300(2) 1.55762(18) 0.0338(5) Uani 1 1 d . . . H8 H 1.0309 0.7704 1.6197 0.041 Uiso 1 1 calc R . . C9 C 1.2266(4) 0.6618(2) 1.51776(18) 0.0314(5) Uani 1 1 d . . . H9 H 1.3557 0.6563 1.5530 0.038 Uiso 1 1 calc R . . C10 C 1.2301(4) 0.6014(2) 1.42518(17) 0.0275(5) Uani 1 1 d . . . H10 H 1.3618 0.5558 1.3984 0.033 Uiso 1 1 calc R . . C11 C 0.8592(3) 0.72207(19) 0.90318(16) 0.0251(5) Uani 1 1 d . . . H11A H 0.7392 0.6715 0.9087 0.030 Uiso 1 1 calc R . . H11B H 0.9719 0.6941 0.8461 0.030 Uiso 1 1 calc R . . C12 C 0.7668(3) 0.85696(19) 0.87015(16) 0.0225(4) Uani 1 1 d . . . C13 C 0.4957(3) 0.98781(19) 0.75090(17) 0.0251(5) Uani 1 1 d . . . C14 C 0.3855(4) 1.0725(2) 0.83733(19) 0.0326(5) Uani 1 1 d . . . H14A H 0.2673 1.0347 0.8812 0.049 Uiso 1 1 calc R . . H14B H 0.3253 1.1507 0.8011 0.049 Uiso 1 1 calc R . . H14C H 0.4951 1.0851 0.8837 0.049 Uiso 1 1 calc R . . C15 C 0.3178(4) 0.9559(2) 0.68560(19) 0.0310(5) Uani 1 1 d . . . H15A H 0.3867 0.9020 0.6322 0.046 Uiso 1 1 calc R . . H15B H 0.2444 1.0303 0.6487 0.046 Uiso 1 1 calc R . . H15C H 0.2100 0.9151 0.7347 0.046 Uiso 1 1 calc R . . C16 C 0.6735(4) 1.0487(2) 0.67409(18) 0.0300(5) Uani 1 1 d . . . H16A H 0.7864 1.0663 0.7162 0.045 Uiso 1 1 calc R . . H16B H 0.6057 1.1243 0.6365 0.045 Uiso 1 1 calc R . . H16C H 0.7404 0.9937 0.6212 0.045 Uiso 1 1 calc R . . H3N H 0.547(4) 0.802(2) 0.8004(19) 0.030(6) 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 Cl1 0.0273(3) 0.0283(3) 0.0373(3) -0.0052(2) -0.0043(2) -0.0081(2) O1 0.0343(8) 0.0266(8) 0.0307(8) -0.0034(6) -0.0080(7) -0.0093(7) N1 0.0240(9) 0.0231(9) 0.0203(9) -0.0015(7) -0.0024(7) -0.0043(7) N2 0.0235(9) 0.0238(9) 0.0223(9) -0.0019(7) -0.0032(7) -0.0048(7) N3 0.0255(9) 0.0192(9) 0.0271(10) -0.0014(7) -0.0045(7) -0.0056(7) C1 0.0216(10) 0.0201(10) 0.0239(10) -0.0034(8) -0.0029(8) -0.0045(8) C2 0.0274(11) 0.0334(12) 0.0284(12) -0.0004(9) -0.0059(9) -0.0128(9) C3 0.0274(11) 0.0336(12) 0.0276(12) 0.0026(9) -0.0047(9) -0.0134(9) C4 0.0284(11) 0.0215(11) 0.0243(11) -0.0004(9) -0.0053(8) -0.0022(8) C5 0.0281(11) 0.0195(10) 0.0214(10) 0.0028(8) -0.0024(8) -0.0053(8) C6 0.0286(11) 0.0294(12) 0.0314(12) -0.0037(9) -0.0048(9) -0.0028(9) C7 0.0389(13) 0.0273(12) 0.0363(13) -0.0081(10) 0.0045(10) -0.0006(10) C8 0.0506(14) 0.0307(12) 0.0229(11) -0.0046(9) -0.0029(10) -0.0137(10) C9 0.0358(12) 0.0344(13) 0.0268(11) 0.0028(10) -0.0118(9) -0.0124(10) C10 0.0280(11) 0.0269(11) 0.0270(11) 0.0003(9) -0.0037(9) -0.0040(9) C11 0.0272(11) 0.0279(11) 0.0213(10) -0.0043(9) -0.0064(8) -0.0031(9) C12 0.0248(10) 0.0240(11) 0.0186(10) -0.0038(8) 0.0008(8) -0.0043(8) C13 0.0271(11) 0.0206(11) 0.0263(11) -0.0010(9) -0.0035(9) -0.0003(8) C14 0.0351(13) 0.0270(12) 0.0339(12) -0.0036(10) 0.0009(10) -0.0017(9) C15 0.0290(12) 0.0311(12) 0.0332(12) -0.0019(10) -0.0084(9) -0.0023(9) C16 0.0309(12) 0.0271(12) 0.0303(12) 0.0008(9) 0.0000(9) -0.0043(9) _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 O1 C12 1.224(2) . ? N1 C1 1.329(3) . ? N1 C2 1.377(3) . ? N1 C4 1.482(3) . ? N2 C1 1.330(3) . ? N2 C3 1.379(3) . ? N2 C11 1.462(3) . ? N3 C12 1.343(3) . ? N3 C13 1.482(3) . ? N3 H3N 0.86(3) . ? C1 H1 0.9300 . ? C2 C3 1.346(3) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.506(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.388(3) . ? C5 C6 1.388(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 C8 1.380(3) . ? C7 H7 0.9300 . ? C8 C9 1.377(3) . ? C8 H8 0.9300 . ? C9 C10 1.387(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.529(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C15 1.523(3) . ? C13 C16 1.525(3) . ? C13 C14 1.534(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 N1 C2 108.41(17) . . ? C1 N1 C4 125.36(17) . . ? C2 N1 C4 126.11(17) . . ? C1 N2 C3 108.64(17) . . ? C1 N2 C11 124.13(17) . . ? C3 N2 C11 127.02(18) . . ? C12 N3 C13 124.75(18) . . ? C12 N3 H3N 115.4(16) . . ? C13 N3 H3N 119.9(16) . . ? N1 C1 N2 108.60(17) . . ? N1 C1 H1 125.7 . . ? N2 C1 H1 125.7 . . ? C3 C2 N1 107.45(18) . . ? C3 C2 H2 126.3 . . ? N1 C2 H2 126.3 . . ? C2 C3 N2 106.89(19) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N1 C4 C5 111.87(16) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C10 C5 C6 118.88(19) . . ? C10 C5 C4 120.43(19) . . ? C6 C5 C4 120.65(18) . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 120.3(2) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? N2 C11 C12 112.74(16) . . ? N2 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N2 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? O1 C12 N3 125.90(19) . . ? O1 C12 C11 120.96(18) . . ? N3 C12 C11 113.02(17) . . ? N3 C13 C15 106.14(17) . . ? N3 C13 C16 109.77(16) . . ? C15 C13 C16 110.44(18) . . ? N3 C13 C14 109.67(17) . . ? C15 C13 C14 109.58(17) . . ? C16 C13 C14 111.11(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C2 N1 C1 N2 -0.1(2) . . . . ? C4 N1 C1 N2 -176.43(17) . . . . ? C3 N2 C1 N1 0.1(2) . . . . ? C11 N2 C1 N1 175.11(17) . . . . ? C1 N1 C2 C3 0.2(2) . . . . ? C4 N1 C2 C3 176.40(18) . . . . ? N1 C2 C3 N2 -0.1(2) . . . . ? C1 N2 C3 C2 0.0(2) . . . . ? C11 N2 C3 C2 -174.82(19) . . . . ? C1 N1 C4 C5 -133.2(2) . . . . ? C2 N1 C4 C5 51.2(3) . . . . ? N1 C4 C5 C10 -106.4(2) . . . . ? N1 C4 C5 C6 75.8(2) . . . . ? C10 C5 C6 C7 0.2(3) . . . . ? C4 C5 C6 C7 178.0(2) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C5 -0.3(3) . . . . ? C6 C5 C10 C9 0.2(3) . . . . ? C4 C5 C10 C9 -177.64(19) . . . . ? C1 N2 C11 C12 127.9(2) . . . . ? C3 N2 C11 C12 -58.0(3) . . . . ? C13 N3 C12 O1 4.1(3) . . . . ? C13 N3 C12 C11 -171.93(17) . . . . ? N2 C11 C12 O1 31.3(3) . . . . ? N2 C11 C12 N3 -152.46(17) . . . . ? C12 N3 C13 C15 178.20(18) . . . . ? C12 N3 C13 C16 58.8(2) . . . . ? C12 N3 C13 C14 -63.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.232 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.055 # Attachment 'pg070.cif' data_pg070 _database_code_depnum_ccdc_archive 'CCDC 627573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Cl2 N3 O Pd' _chemical_formula_weight 512.74 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9556(10) _cell_length_b 9.830(2) _cell_length_c 14.552(2) _cell_angle_alpha 71.923(17) _cell_angle_beta 75.819(10) _cell_angle_gamma 64.689(16) _cell_volume 1091.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9851 _cell_measurement_theta_min 3.0948 _cell_measurement_theta_max 32.1699 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.111 _exptl_absorpt_correction_T_min 0.6775 _exptl_absorpt_correction_T_max 0.7245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11035 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3827 _reflns_number_gt 3407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0251P)^2^+3.8693P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3827 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.002 _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 0.79004(4) 0.25538(3) 0.17283(2) 0.02777(11) Uani 1 1 d . . . Cl1 Cl 0.73055(13) 0.22356(12) 0.03712(7) 0.0359(2) Uani 1 1 d . . . Cl2 Cl 0.84044(14) 0.28523(12) 0.31200(7) 0.0366(2) Uani 1 1 d . . . O1 O 0.7298(4) -0.0037(4) 0.4509(2) 0.0475(8) Uani 1 1 d . . . H1 H 0.7128 0.0823 0.4142 0.071 Uiso 1 1 calc R . . N1 N 0.4298(4) 0.3778(4) 0.2443(2) 0.0332(8) Uani 1 1 d . . . N2 N 0.5345(5) 0.1295(4) 0.2927(3) 0.0390(8) Uani 1 1 d . . . N3 N 1.0216(4) 0.2580(4) 0.0990(2) 0.0327(8) Uani 1 1 d . . . C1 C 0.5724(5) 0.2526(4) 0.2414(3) 0.0291(8) Uani 1 1 d . . . C2 C 0.3681(7) 0.1763(6) 0.3269(3) 0.0515(13) Uani 1 1 d . . . H2 H 0.3116 0.1127 0.3639 0.062 Uiso 1 1 calc R . . C3 C 0.3015(6) 0.3311(6) 0.2971(3) 0.0477(12) Uani 1 1 d . . . H3 H 0.1904 0.3949 0.3095 0.057 Uiso 1 1 calc R . . C4 C 0.4176(6) 0.5371(5) 0.1990(3) 0.0430(11) Uani 1 1 d . . . H4A H 0.3507 0.5796 0.1460 0.052 Uiso 1 1 calc R . . H4B H 0.5282 0.5362 0.1716 0.052 Uiso 1 1 calc R . . C5 C 0.3410(5) 0.6409(5) 0.2702(3) 0.0332(9) Uani 1 1 d . . . C6 C 0.3674(6) 0.5874(5) 0.3670(3) 0.0423(10) Uani 1 1 d . . . H6 H 0.4308 0.4837 0.3909 0.051 Uiso 1 1 calc R . . C7 C 0.2994(6) 0.6883(6) 0.4280(3) 0.0430(11) Uani 1 1 d . . . H7 H 0.3174 0.6521 0.4931 0.052 Uiso 1 1 calc R . . C8 C 0.2052(6) 0.8422(5) 0.3933(4) 0.0434(11) Uani 1 1 d . . . H8 H 0.1584 0.9090 0.4351 0.052 Uiso 1 1 calc R . . C9 C 0.1805(5) 0.8971(5) 0.2967(4) 0.0405(10) Uani 1 1 d . . . H9 H 0.1196 1.0015 0.2727 0.049 Uiso 1 1 calc R . . C10 C 0.2468(5) 0.7959(5) 0.2352(3) 0.0351(9) Uani 1 1 d . . . H10 H 0.2280 0.8322 0.1703 0.042 Uiso 1 1 calc R . . C11 C 0.6601(8) -0.0333(5) 0.3099(4) 0.0606(15) Uani 1 1 d . . . H11 H 0.7612 -0.0202 0.2710 0.073 Uiso 1 1 calc R . . C12 C 0.7078(8) -0.0984(6) 0.4052(5) 0.075(2) Uani 1 1 d . . . H12 H 0.6077 -0.1134 0.4442 0.090 Uiso 1 1 calc R . . C13 C 0.8348(6) -0.2603(5) 0.4185(4) 0.0451(11) Uani 1 1 d . . . H13A H 0.8408 -0.3047 0.4877 0.054 Uiso 1 1 calc R . . H13B H 0.9428 -0.2568 0.3882 0.054 Uiso 1 1 calc R . . C14 C 0.8014(9) -0.3652(7) 0.3769(5) 0.079(2) Uani 1 1 d . . . H14A H 0.8993 -0.4603 0.3772 0.094 Uiso 1 1 calc R . . H14B H 0.7101 -0.3916 0.4181 0.094 Uiso 1 1 calc R . . C15 C 0.7592(9) -0.2937(5) 0.2762(4) 0.0688(18) Uani 1 1 d . . . H15A H 0.7177 -0.3574 0.2586 0.083 Uiso 1 1 calc R . . H15B H 0.8608 -0.2954 0.2327 0.083 Uiso 1 1 calc R . . C16 C 0.6306(6) -0.1273(6) 0.2585(4) 0.0463(11) Uani 1 1 d . . . H16A H 0.6369 -0.0805 0.1891 0.056 Uiso 1 1 calc R . . H16B H 0.5197 -0.1281 0.2814 0.056 Uiso 1 1 calc R . . C17 C 1.1201(5) 0.1495(5) 0.0482(3) 0.0386(10) Uani 1 1 d . . . H17 H 1.0796 0.0790 0.0443 0.046 Uiso 1 1 calc R . . C18 C 1.2772(6) 0.1381(6) 0.0018(4) 0.0489(12) Uani 1 1 d . . . H18 H 1.3430 0.0593 -0.0304 0.059 Uiso 1 1 calc R . . C19 C 1.3340(7) 0.2458(7) 0.0043(4) 0.0564(14) Uani 1 1 d . . . H19 H 1.4390 0.2415 -0.0273 0.068 Uiso 1 1 calc R . . C20 C 1.2373(7) 0.3590(7) 0.0527(4) 0.0586(15) Uani 1 1 d . . . H20 H 1.2748 0.4333 0.0537 0.070 Uiso 1 1 calc R . . C21 C 1.0795(6) 0.3621(6) 0.1015(4) 0.0482(12) Uani 1 1 d . . . H21 H 1.0141 0.4378 0.1360 0.058 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 Pd1 0.03203(18) 0.02321(16) 0.02932(17) -0.00995(12) -0.00424(12) -0.00896(12) Cl1 0.0379(5) 0.0465(6) 0.0307(5) -0.0131(4) -0.0057(4) -0.0196(5) Cl2 0.0525(6) 0.0327(5) 0.0319(5) -0.0130(4) -0.0071(4) -0.0184(5) O1 0.064(2) 0.0394(18) 0.0467(19) -0.0090(14) -0.0110(16) -0.0261(16) N1 0.0354(19) 0.0254(17) 0.0296(18) -0.0067(14) 0.0020(14) -0.0063(15) N2 0.053(2) 0.0280(18) 0.037(2) -0.0057(15) -0.0050(17) -0.0193(17) N3 0.0376(19) 0.0327(18) 0.0314(18) -0.0031(14) -0.0121(15) -0.0156(15) C1 0.039(2) 0.0217(19) 0.027(2) -0.0078(15) -0.0071(16) -0.0091(17) C2 0.070(3) 0.062(3) 0.038(3) -0.012(2) 0.006(2) -0.046(3) C3 0.036(2) 0.066(3) 0.039(3) -0.022(2) 0.012(2) -0.020(2) C4 0.054(3) 0.024(2) 0.031(2) -0.0057(17) 0.001(2) -0.001(2) C5 0.029(2) 0.029(2) 0.035(2) -0.0099(17) -0.0008(17) -0.0047(17) C6 0.040(2) 0.041(2) 0.036(2) -0.0081(19) -0.0063(19) -0.005(2) C7 0.044(3) 0.057(3) 0.037(2) -0.018(2) -0.002(2) -0.024(2) C8 0.043(3) 0.046(3) 0.056(3) -0.030(2) 0.006(2) -0.024(2) C9 0.038(2) 0.027(2) 0.055(3) -0.016(2) -0.004(2) -0.0086(18) C10 0.033(2) 0.029(2) 0.037(2) -0.0090(18) -0.0029(18) -0.0067(18) C11 0.106(5) 0.023(2) 0.052(3) -0.005(2) -0.026(3) -0.018(3) C12 0.080(4) 0.046(3) 0.107(5) -0.043(3) -0.053(4) 0.007(3) C13 0.041(3) 0.037(2) 0.057(3) -0.011(2) -0.006(2) -0.014(2) C14 0.087(5) 0.040(3) 0.107(5) -0.032(3) -0.035(4) 0.000(3) C15 0.133(6) 0.026(2) 0.049(3) -0.013(2) 0.007(3) -0.039(3) C16 0.045(3) 0.051(3) 0.054(3) -0.028(2) 0.001(2) -0.022(2) C17 0.036(2) 0.043(3) 0.036(2) -0.0114(19) -0.0055(18) -0.013(2) C18 0.038(3) 0.059(3) 0.043(3) -0.008(2) -0.005(2) -0.015(2) C19 0.048(3) 0.074(4) 0.045(3) 0.000(3) -0.007(2) -0.030(3) C20 0.067(4) 0.064(4) 0.061(3) 0.006(3) -0.026(3) -0.046(3) C21 0.058(3) 0.046(3) 0.049(3) -0.006(2) -0.018(2) -0.026(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 Pd1 C1 1.967(4) . ? Pd1 N3 2.096(3) . ? Pd1 Cl2 2.3068(10) . ? Pd1 Cl1 2.3071(10) . ? O1 C12 1.397(6) . ? O1 H1 0.8200 . ? N1 C1 1.345(5) . ? N1 C3 1.386(6) . ? N1 C4 1.466(5) . ? N2 C1 1.343(5) . ? N2 C2 1.368(6) . ? N2 C11 1.496(6) . ? N3 C21 1.343(6) . ? N3 C17 1.352(5) . ? C2 C3 1.342(7) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.515(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.382(6) . ? C5 C10 1.386(6) . ? C6 C7 1.382(6) . ? C6 H6 0.9300 . ? C7 C8 1.378(7) . ? C7 H7 0.9300 . ? C8 C9 1.377(7) . ? C8 H8 0.9300 . ? C9 C10 1.389(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.421(8) . ? C11 C16 1.490(6) . ? C11 H11 0.9800 . ? C12 C13 1.494(7) . ? C12 H12 0.9800 . ? C13 C14 1.503(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.479(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.530(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.376(6) . ? C17 H17 0.9300 . ? C18 C19 1.368(8) . ? C18 H18 0.9300 . ? C19 C20 1.360(8) . ? C19 H19 0.9300 . ? C20 C21 1.409(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 Pd1 N3 179.66(14) . . ? C1 Pd1 Cl2 88.70(11) . . ? N3 Pd1 Cl2 91.64(9) . . ? C1 Pd1 Cl1 89.07(11) . . ? N3 Pd1 Cl1 90.59(9) . . ? Cl2 Pd1 Cl1 177.74(4) . . ? C12 O1 H1 109.5 . . ? C1 N1 C3 109.3(4) . . ? C1 N1 C4 123.9(4) . . ? C3 N1 C4 126.8(4) . . ? C1 N2 C2 110.1(4) . . ? C1 N2 C11 123.6(4) . . ? C2 N2 C11 126.3(4) . . ? C21 N3 C17 117.7(4) . . ? C21 N3 Pd1 122.6(3) . . ? C17 N3 Pd1 119.7(3) . . ? N2 C1 N1 106.4(4) . . ? N2 C1 Pd1 128.1(3) . . ? N1 C1 Pd1 125.5(3) . . ? C3 C2 N2 107.3(4) . . ? C3 C2 H2 126.4 . . ? N2 C2 H2 126.4 . . ? C2 C3 N1 107.0(4) . . ? C2 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? N1 C4 C5 112.8(3) . . ? N1 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N1 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C10 119.6(4) . . ? C6 C5 C4 122.3(4) . . ? C10 C5 C4 118.1(4) . . ? C7 C6 C5 119.9(4) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 120.0(4) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.7(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C5 C10 C9 120.3(4) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C16 120.4(5) . . ? C12 C11 N2 115.7(4) . . ? C16 C11 N2 111.2(4) . . ? C12 C11 H11 102.0 . . ? C16 C11 H11 102.0 . . ? N2 C11 H11 102.0 . . ? O1 C12 C11 117.9(5) . . ? O1 C12 C13 115.1(4) . . ? C11 C12 C13 113.8(5) . . ? O1 C12 H12 102.3 . . ? C11 C12 H12 102.3 . . ? C13 C12 H12 102.3 . . ? C12 C13 C14 114.7(4) . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 112.5(5) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 116.0(4) . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C11 C16 C15 111.1(4) . . ? C11 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C11 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N3 C17 C18 123.4(4) . . ? N3 C17 H17 118.3 . . ? C18 C17 H17 118.3 . . ? C19 C18 C17 118.2(5) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C20 C19 C18 120.3(5) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.1(5) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? N3 C21 C20 121.3(5) . . ? N3 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? 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 C1 Pd1 N3 C21 139(27) . . . . ? Cl2 Pd1 N3 C21 -45.6(3) . . . . ? Cl1 Pd1 N3 C21 134.8(3) . . . . ? C1 Pd1 N3 C17 -43(27) . . . . ? Cl2 Pd1 N3 C17 132.9(3) . . . . ? Cl1 Pd1 N3 C17 -46.7(3) . . . . ? C2 N2 C1 N1 0.7(5) . . . . ? C11 N2 C1 N1 -178.2(4) . . . . ? C2 N2 C1 Pd1 -178.4(3) . . . . ? C11 N2 C1 Pd1 2.7(6) . . . . ? C3 N1 C1 N2 -0.8(5) . . . . ? C4 N1 C1 N2 178.4(4) . . . . ? C3 N1 C1 Pd1 178.4(3) . . . . ? C4 N1 C1 Pd1 -2.5(6) . . . . ? N3 Pd1 C1 N2 83(27) . . . . ? Cl2 Pd1 C1 N2 -92.3(4) . . . . ? Cl1 Pd1 C1 N2 87.3(4) . . . . ? N3 Pd1 C1 N1 -96(27) . . . . ? Cl2 Pd1 C1 N1 88.8(3) . . . . ? Cl1 Pd1 C1 N1 -91.6(3) . . . . ? C1 N2 C2 C3 -0.4(5) . . . . ? C11 N2 C2 C3 178.4(4) . . . . ? N2 C2 C3 N1 0.0(5) . . . . ? C1 N1 C3 C2 0.5(5) . . . . ? C4 N1 C3 C2 -178.6(4) . . . . ? C1 N1 C4 C5 -125.0(4) . . . . ? C3 N1 C4 C5 54.0(6) . . . . ? N1 C4 C5 C6 34.7(6) . . . . ? N1 C4 C5 C10 -147.8(4) . . . . ? C10 C5 C6 C7 0.2(7) . . . . ? C4 C5 C6 C7 177.7(4) . . . . ? C5 C6 C7 C8 0.0(7) . . . . ? C6 C7 C8 C9 -1.1(7) . . . . ? C7 C8 C9 C10 1.8(7) . . . . ? C6 C5 C10 C9 0.5(6) . . . . ? C4 C5 C10 C9 -177.0(4) . . . . ? C8 C9 C10 C5 -1.6(6) . . . . ? C1 N2 C11 C12 105.0(6) . . . . ? C2 N2 C11 C12 -73.7(7) . . . . ? C1 N2 C11 C16 -112.8(5) . . . . ? C2 N2 C11 C16 68.5(6) . . . . ? C16 C11 C12 O1 -178.5(5) . . . . ? N2 C11 C12 O1 -40.0(9) . . . . ? C16 C11 C12 C13 42.1(9) . . . . ? N2 C11 C12 C13 -179.3(5) . . . . ? O1 C12 C13 C14 174.7(6) . . . . ? C11 C12 C13 C14 -44.7(8) . . . . ? C12 C13 C14 C15 47.7(8) . . . . ? C13 C14 C15 C16 -46.8(8) . . . . ? C12 C11 C16 C15 -39.8(8) . . . . ? N2 C11 C16 C15 -180.0(4) . . . . ? C14 C15 C16 C11 41.4(7) . . . . ? C21 N3 C17 C18 2.0(6) . . . . ? Pd1 N3 C17 C18 -176.6(3) . . . . ? N3 C17 C18 C19 -2.5(7) . . . . ? C17 C18 C19 C20 0.9(7) . . . . ? C18 C19 C20 C21 1.0(8) . . . . ? C17 N3 C21 C20 0.1(6) . . . . ? Pd1 N3 C21 C20 178.6(3) . . . . ? C19 C20 C21 N3 -1.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.515 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.089 # Attachment 'pg082.cif' data_pg082 _database_code_depnum_ccdc_archive 'CCDC 630834' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 Cl2 N4 O Pd' _chemical_formula_weight 527.76 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.829(2) _cell_length_b 11.2668(15) _cell_length_c 11.429(2) _cell_angle_alpha 107.068(14) _cell_angle_beta 111.852(19) _cell_angle_gamma 100.997(14) _cell_volume 1164.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8313 _cell_measurement_theta_min 3.0515 _cell_measurement_theta_max 32.5065 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_T_min 0.7111 _exptl_absorpt_correction_T_max 0.7801 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9996 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4090 _reflns_number_gt 3400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0724P)^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 4090 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Pd1 Pd 0.25456(3) 0.48867(2) 1.14091(2) 0.02347(12) Uani 1 1 d . . . Cl2 Cl 0.32817(10) 0.31721(8) 1.17038(9) 0.0358(2) Uani 1 1 d . . . Cl1 Cl 0.17521(9) 0.65904(8) 1.11361(8) 0.0309(2) Uani 1 1 d . . . O1 O 0.0202(3) 0.3198(3) 1.3703(3) 0.0517(8) Uani 1 1 d . . . N1 N 0.3936(3) 0.6216(2) 1.4464(3) 0.0232(6) Uani 1 1 d . . . N2 N 0.1688(3) 0.5472(2) 1.3644(3) 0.0235(6) Uani 1 1 d . . . N3 N -0.1314(3) 0.2512(3) 1.1457(3) 0.0295(7) Uani 1 1 d . . . N4 N 0.2391(3) 0.4239(3) 0.9433(3) 0.0255(6) Uani 1 1 d . . . C1 C 0.2724(3) 0.5533(3) 1.3272(3) 0.0224(7) Uani 1 1 d . . . C2 C 0.3613(4) 0.6585(3) 1.5553(3) 0.0273(7) Uani 1 1 d . . . H2 H 0.4257 0.7072 1.6474 0.033 Uiso 1 1 calc R . . C3 C 0.2216(4) 0.6116(3) 1.5039(3) 0.0266(7) Uani 1 1 d . . . H3 H 0.1698 0.6207 1.5531 0.032 Uiso 1 1 calc R . . C4 C 0.5365(3) 0.6556(3) 1.4587(3) 0.0261(7) Uani 1 1 d . . . H4A H 0.5335 0.6012 1.3736 0.031 Uiso 1 1 calc R . . H4B H 0.5966 0.6349 1.5317 0.031 Uiso 1 1 calc R . . C5 C 0.6008(3) 0.7973(3) 1.4886(3) 0.0259(7) Uani 1 1 d . . . C6 C 0.7121(4) 0.8814(3) 1.6150(4) 0.0340(8) Uani 1 1 d . . . H6 H 0.7471 0.8498 1.6828 0.041 Uiso 1 1 calc R . . C7 C 0.7719(4) 1.0122(3) 1.6417(4) 0.0411(10) Uani 1 1 d . . . H7 H 0.8475 1.0676 1.7272 0.049 Uiso 1 1 calc R . . C8 C 0.7215(4) 1.0613(4) 1.5440(4) 0.0411(9) Uani 1 1 d . . . H8 H 0.7627 1.1493 1.5627 0.049 Uiso 1 1 calc R . . C9 C 0.6100(4) 0.9796(4) 1.4188(4) 0.0420(10) Uani 1 1 d . . . H9 H 0.5743 1.0125 1.3524 0.050 Uiso 1 1 calc R . . C10 C 0.5500(4) 0.8478(3) 1.3903(4) 0.0347(8) Uani 1 1 d . . . H10 H 0.4749 0.7928 1.3045 0.042 Uiso 1 1 calc R . . C11 C 0.0204(3) 0.4773(3) 1.2690(4) 0.0278(7) Uani 1 1 d . . . H11A H 0.0047 0.4699 1.1775 0.033 Uiso 1 1 calc R . . H11B H -0.0354 0.5273 1.2956 0.033 Uiso 1 1 calc R . . C12 C -0.0283(3) 0.3399(3) 1.2661(3) 0.0264(7) Uani 1 1 d . . . C13 C -0.1991(4) 0.1115(3) 1.1087(4) 0.0352(9) Uani 1 1 d . . . C14 C -0.3088(6) 0.0527(4) 0.9596(4) 0.0714(16) Uani 1 1 d . . . H14A H -0.3746 0.0996 0.9477 0.107 Uiso 1 1 calc R . . H14B H -0.3583 -0.0385 0.9334 0.107 Uiso 1 1 calc R . . H14C H -0.2630 0.0595 0.9031 0.107 Uiso 1 1 calc R . . C15 C -0.0917(6) 0.0450(5) 1.1236(8) 0.114(3) Uani 1 1 d . . . H15A H -0.0441 0.0616 1.0710 0.171 Uiso 1 1 calc R . . H15B H -0.1374 -0.0483 1.0907 0.171 Uiso 1 1 calc R . . H15C H -0.0242 0.0786 1.2188 0.171 Uiso 1 1 calc R . . C16 C -0.2675(8) 0.0955(6) 1.1974(6) 0.111(3) Uani 1 1 d . . . H16A H -0.1963 0.1276 1.2910 0.166 Uiso 1 1 calc R . . H16B H -0.3191 0.0039 1.1664 0.166 Uiso 1 1 calc R . . H16C H -0.3312 0.1447 1.1920 0.166 Uiso 1 1 calc R . . C17 C 0.3168(4) 0.5007(4) 0.9091(4) 0.0318(8) Uani 1 1 d . . . H17 H 0.3787 0.5837 0.9754 0.038 Uiso 1 1 calc R . . C18 C 0.3097(4) 0.4629(4) 0.7807(4) 0.0398(9) Uani 1 1 d . . . H18 H 0.3662 0.5188 0.7607 0.048 Uiso 1 1 calc R . . C19 C 0.2173(4) 0.3403(4) 0.6817(4) 0.0418(10) Uani 1 1 d . . . H19 H 0.2092 0.3122 0.5933 0.050 Uiso 1 1 calc R . . C20 C 0.1386(4) 0.2618(4) 0.7163(4) 0.0399(9) Uani 1 1 d . . . H20 H 0.0758 0.1786 0.6513 0.048 Uiso 1 1 calc R . . C21 C 0.1511(4) 0.3047(3) 0.8474(4) 0.0350(8) Uani 1 1 d . . . H21 H 0.0969 0.2492 0.8697 0.042 Uiso 1 1 calc R . . H3N H -0.144(4) 0.275(3) 1.092(4) 0.020(10) 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 Pd1 0.02689(17) 0.01725(16) 0.01677(16) 0.00398(11) 0.00508(12) 0.00241(11) Cl2 0.0481(5) 0.0241(4) 0.0259(5) 0.0083(4) 0.0080(4) 0.0139(4) Cl1 0.0413(5) 0.0230(4) 0.0224(4) 0.0087(3) 0.0086(4) 0.0115(4) O1 0.0596(19) 0.0335(14) 0.0276(14) 0.0154(12) -0.0030(13) -0.0126(13) N1 0.0227(14) 0.0191(13) 0.0191(14) 0.0057(11) 0.0042(12) 0.0037(11) N2 0.0207(14) 0.0203(13) 0.0245(14) 0.0087(11) 0.0077(12) 0.0022(11) N3 0.0341(17) 0.0229(15) 0.0216(16) 0.0093(13) 0.0060(14) 0.0022(13) N4 0.0251(15) 0.0212(14) 0.0232(15) 0.0069(12) 0.0064(12) 0.0061(12) C1 0.0241(17) 0.0149(15) 0.0226(17) 0.0079(13) 0.0053(14) 0.0054(12) C2 0.0303(19) 0.0254(16) 0.0173(16) 0.0067(14) 0.0060(15) 0.0041(14) C3 0.0293(18) 0.0267(17) 0.0202(17) 0.0085(14) 0.0089(15) 0.0080(14) C4 0.0249(17) 0.0206(16) 0.0238(17) 0.0040(14) 0.0071(14) 0.0054(13) C5 0.0226(17) 0.0224(16) 0.0261(18) 0.0056(14) 0.0096(14) 0.0039(13) C6 0.033(2) 0.0262(18) 0.0288(19) 0.0084(15) 0.0060(16) 0.0006(15) C7 0.039(2) 0.0221(18) 0.036(2) 0.0038(16) 0.0042(18) -0.0043(16) C8 0.041(2) 0.0249(18) 0.057(3) 0.0179(18) 0.023(2) 0.0053(16) C9 0.044(2) 0.040(2) 0.049(2) 0.029(2) 0.020(2) 0.0111(18) C10 0.0293(19) 0.0300(18) 0.0283(19) 0.0078(16) 0.0051(16) -0.0014(15) C11 0.0198(17) 0.0239(17) 0.0314(19) 0.0105(15) 0.0049(15) 0.0049(13) C12 0.0224(17) 0.0244(17) 0.0238(18) 0.0070(14) 0.0069(15) 0.0020(13) C13 0.040(2) 0.0211(17) 0.0295(19) 0.0050(15) 0.0103(17) -0.0016(15) C14 0.083(4) 0.035(2) 0.036(3) 0.005(2) -0.006(2) -0.020(2) C15 0.059(3) 0.027(2) 0.179(7) 0.008(3) 0.002(4) 0.015(2) C16 0.145(6) 0.061(3) 0.061(3) -0.018(3) 0.061(4) -0.062(4) C17 0.0253(18) 0.0343(19) 0.032(2) 0.0130(16) 0.0088(16) 0.0113(15) C18 0.038(2) 0.059(3) 0.034(2) 0.023(2) 0.0213(18) 0.0237(19) C19 0.043(2) 0.063(3) 0.026(2) 0.0143(19) 0.0182(18) 0.030(2) C20 0.041(2) 0.038(2) 0.0245(19) 0.0019(16) 0.0074(17) 0.0143(17) C21 0.037(2) 0.0288(18) 0.031(2) 0.0075(16) 0.0121(17) 0.0083(16) _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 C1 1.957(3) . ? Pd1 N4 2.089(3) . ? Pd1 Cl2 2.2913(9) . ? Pd1 Cl1 2.3026(9) . ? O1 C12 1.218(4) . ? N1 C1 1.356(4) . ? N1 C2 1.385(4) . ? N1 C4 1.463(4) . ? N2 C1 1.337(4) . ? N2 C3 1.371(4) . ? N2 C11 1.449(4) . ? N3 C12 1.328(5) . ? N3 C13 1.461(5) . ? N3 H3N 0.72(3) . ? N4 C17 1.333(5) . ? N4 C21 1.336(4) . ? C2 C3 1.328(5) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.493(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.380(5) . ? C5 C10 1.387(5) . ? C6 C7 1.382(5) . ? C6 H6 0.9300 . ? C7 C8 1.369(6) . ? C7 H7 0.9300 . ? C8 C9 1.368(6) . ? C8 H8 0.9300 . ? C9 C10 1.387(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.524(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C15 1.484(7) . ? C13 C16 1.491(6) . ? C13 C14 1.511(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.370(5) . ? C17 H17 0.9300 . ? C18 C19 1.379(6) . ? C18 H18 0.9300 . ? C19 C20 1.355(6) . ? C19 H19 0.9300 . ? C20 C21 1.376(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 Pd1 N4 178.63(11) . . ? C1 Pd1 Cl2 91.24(9) . . ? N4 Pd1 Cl2 89.44(8) . . ? C1 Pd1 Cl1 87.62(9) . . ? N4 Pd1 Cl1 91.74(8) . . ? Cl2 Pd1 Cl1 178.14(3) . . ? C1 N1 C2 109.4(3) . . ? C1 N1 C4 125.6(3) . . ? C2 N1 C4 124.9(3) . . ? C1 N2 C3 111.3(3) . . ? C1 N2 C11 123.8(3) . . ? C3 N2 C11 124.8(3) . . ? C12 N3 C13 127.7(3) . . ? C12 N3 H3N 113(3) . . ? C13 N3 H3N 118(3) . . ? C17 N4 C21 117.9(3) . . ? C17 N4 Pd1 120.9(2) . . ? C21 N4 Pd1 121.2(2) . . ? N2 C1 N1 105.1(3) . . ? N2 C1 Pd1 127.9(2) . . ? N1 C1 Pd1 126.9(2) . . ? C3 C2 N1 107.5(3) . . ? C3 C2 H2 126.3 . . ? N1 C2 H2 126.3 . . ? C2 C3 N2 106.7(3) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N1 C4 C5 113.7(3) . . ? N1 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N1 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C10 118.3(3) . . ? C6 C5 C4 120.7(3) . . ? C10 C5 C4 120.9(3) . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 120.7(3) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? N2 C11 C12 111.5(3) . . ? N2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N2 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? O1 C12 N3 124.9(3) . . ? O1 C12 C11 120.7(3) . . ? N3 C12 C11 114.3(3) . . ? N3 C13 C15 109.2(4) . . ? N3 C13 C16 110.4(4) . . ? C15 C13 C16 110.6(5) . . ? N3 C13 C14 107.5(3) . . ? C15 C13 C14 108.9(4) . . ? C16 C13 C14 110.2(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N4 C17 C18 123.0(3) . . ? N4 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C17 C18 C19 118.8(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 118.4(4) . . ? C20 C19 H19 120.8 . . ? C18 C19 H19 120.8 . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? N4 C21 C20 121.7(4) . . ? N4 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? 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 C1 Pd1 N4 C17 1(5) . . . . ? Cl2 Pd1 N4 C17 -118.9(2) . . . . ? Cl1 Pd1 N4 C17 62.6(2) . . . . ? C1 Pd1 N4 C21 -179(100) . . . . ? Cl2 Pd1 N4 C21 61.2(3) . . . . ? Cl1 Pd1 N4 C21 -117.3(3) . . . . ? C3 N2 C1 N1 0.9(3) . . . . ? C11 N2 C1 N1 -177.2(3) . . . . ? C3 N2 C1 Pd1 -175.5(2) . . . . ? C11 N2 C1 Pd1 6.4(4) . . . . ? C2 N1 C1 N2 -1.2(3) . . . . ? C4 N1 C1 N2 -179.1(3) . . . . ? C2 N1 C1 Pd1 175.3(2) . . . . ? C4 N1 C1 Pd1 -2.7(4) . . . . ? N4 Pd1 C1 N2 133(5) . . . . ? Cl2 Pd1 C1 N2 -107.3(3) . . . . ? Cl1 Pd1 C1 N2 71.3(3) . . . . ? N4 Pd1 C1 N1 -42(5) . . . . ? Cl2 Pd1 C1 N1 77.1(3) . . . . ? Cl1 Pd1 C1 N1 -104.4(3) . . . . ? C1 N1 C2 C3 1.0(4) . . . . ? C4 N1 C2 C3 179.0(3) . . . . ? N1 C2 C3 N2 -0.4(4) . . . . ? C1 N2 C3 C2 -0.3(4) . . . . ? C11 N2 C3 C2 177.8(3) . . . . ? C1 N1 C4 C5 105.2(3) . . . . ? C2 N1 C4 C5 -72.4(4) . . . . ? N1 C4 C5 C6 110.3(4) . . . . ? N1 C4 C5 C10 -69.4(4) . . . . ? C10 C5 C6 C7 -0.8(6) . . . . ? C4 C5 C6 C7 179.5(3) . . . . ? C5 C6 C7 C8 0.5(6) . . . . ? C6 C7 C8 C9 0.3(6) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? C8 C9 C10 C5 0.8(6) . . . . ? C6 C5 C10 C9 0.1(5) . . . . ? C4 C5 C10 C9 179.9(4) . . . . ? C1 N2 C11 C12 97.0(4) . . . . ? C3 N2 C11 C12 -80.9(4) . . . . ? C13 N3 C12 O1 -5.7(6) . . . . ? C13 N3 C12 C11 178.8(3) . . . . ? N2 C11 C12 O1 35.0(5) . . . . ? N2 C11 C12 N3 -149.3(3) . . . . ? C12 N3 C13 C15 -61.4(6) . . . . ? C12 N3 C13 C16 60.5(6) . . . . ? C12 N3 C13 C14 -179.3(4) . . . . ? C21 N4 C17 C18 0.3(5) . . . . ? Pd1 N4 C17 C18 -179.6(3) . . . . ? N4 C17 C18 C19 0.5(5) . . . . ? C17 C18 C19 C20 -0.8(6) . . . . ? C18 C19 C20 C21 0.2(6) . . . . ? C17 N4 C21 C20 -0.9(5) . . . . ? Pd1 N4 C21 C20 179.0(3) . . . . ? C19 C20 C21 N4 0.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.088 _refine_diff_density_min -0.728 _refine_diff_density_rms 0.100