# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Wen Hua Sun' _publ_contact_author_email whsun@iccas.ac.cn _publ_section_title ; 2-(N-Alkylcarboxamide)-6-iminopyridyl palladium and nickel complexes: Coordination chemistry and catalysis ; loop_ _publ_author_name 'Wenjuan Zhang' 'Yonghong Wang' 'Jiangang Yu' C.Redshaw 'Xiang Hao' 'Wen Hua Sun' # Attachment '- CIF.CIF' data_C3 _database_code_depnum_ccdc_archive 'CCDC 828935' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H32 Cl N3 O Pd' _chemical_formula_weight 520.38 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 Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.403(3) _cell_length_b 14.090(3) _cell_length_c 12.618(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.67(3) _cell_angle_gamma 90.00 _cell_volume 2355.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9432 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.921 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6766 _exptl_absorpt_correction_T_max 0.7570 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9432 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4332 _reflns_number_gt 4207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELX97 (Sheldrick, 1997)' _computing_publication_material 'SHELX97 (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^)+(0.0647P)^2^+1.8157P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 4332 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 1.00780(3) 0.818089(19) 0.74931(3) 0.02378(11) Uani 1 1 d . . . N2 N 1.1178(3) 0.8968(3) 0.7181(3) 0.0247(8) Uani 1 1 d . . . N3 N 1.0012(3) 0.9203(3) 0.8601(4) 0.0298(9) Uani 1 1 d . . . C2 C 1.1300(4) 0.7821(3) 0.5856(4) 0.0259(10) Uani 1 1 d . . . C3 C 1.1699(4) 0.8703(3) 0.6398(4) 0.0269(10) Uani 1 1 d . . . C1 C 1.1771(4) 0.7440(4) 0.4949(4) 0.0325(11) Uani 1 1 d . . . H1A H 1.1423 0.6857 0.4680 0.049 Uiso 1 1 calc R . . H1B H 1.2485 0.7301 0.5197 0.049 Uiso 1 1 calc R . . H1C H 1.1716 0.7912 0.4372 0.049 Uiso 1 1 calc R . . C4 C 1.2508(4) 0.9249(4) 0.6199(4) 0.0326(11) Uani 1 1 d . . . H4A H 1.2899 0.9064 0.5665 0.039 Uiso 1 1 calc R . . Cl1 Cl 0.87706(10) 0.72463(10) 0.78620(11) 0.0378(3) Uani 1 1 d . . . O1 O 1.0806(3) 1.0599(3) 0.9201(3) 0.0387(9) Uani 1 1 d . . . C23 C 0.7547(7) 0.7454(8) 0.4918(8) 0.0601(18) Uani 1 1 d . . . H23A H 0.7489 0.7225 0.5640 0.090 Uiso 1 1 calc R . . H23B H 0.7217 0.7003 0.4386 0.090 Uiso 1 1 calc R . . H23C H 0.7220 0.8075 0.4805 0.090 Uiso 1 1 calc R . . C6 C 1.2172(4) 1.0336(3) 0.7583(4) 0.0293(11) Uani 1 1 d . . . H6A H 1.2325 1.0899 0.7989 0.035 Uiso 1 1 calc R . . C5 C 1.2739(4) 1.0074(4) 0.6793(4) 0.0325(11) Uani 1 1 d . . . H5A H 1.3287 1.0461 0.6658 0.039 Uiso 1 1 calc R . . C19 C 1.1564(4) 0.5628(4) 0.6878(4) 0.0335(11) Uani 1 1 d . . . H19A H 1.1875 0.6274 0.6961 0.040 Uiso 1 1 calc R . . C17 C 0.8886(5) 0.5782(4) 0.4516(5) 0.0382(13) Uani 1 1 d . . . H17A H 0.8291 0.5803 0.4002 0.046 Uiso 1 1 calc R . . C14 C 1.0635(4) 0.5698(4) 0.6021(4) 0.0288(10) Uani 1 1 d . . . C13 C 1.0128(4) 0.6559(4) 0.5761(4) 0.0261(10) Uani 1 1 d . . . C18 C 0.9240(4) 0.6618(4) 0.5054(4) 0.0306(11) Uani 1 1 d . . . C20 C 1.1236(6) 0.5369(5) 0.7939(5) 0.0519(16) Uani 1 1 d . . . H20A H 1.1831 0.5323 0.8494 0.078 Uiso 1 1 calc R . . H20B H 1.0885 0.4757 0.7871 0.078 Uiso 1 1 calc R . . H20C H 1.0780 0.5859 0.8140 0.078 Uiso 1 1 calc R . . C7 C 1.1374(4) 0.9753(3) 0.7767(4) 0.0279(10) Uani 1 1 d . . . C15 C 1.0244(5) 0.4898(4) 0.5474(5) 0.0356(12) Uani 1 1 d . . . H15A H 1.0577 0.4307 0.5622 0.043 Uiso 1 1 calc R . . C16 C 0.9389(5) 0.4931(4) 0.4722(5) 0.0376(13) Uani 1 1 d . . . H16A H 0.9145 0.4373 0.4348 0.045 Uiso 1 1 calc R . . C22 C 0.8652(4) 0.7543(5) 0.4802(5) 0.0393(13) Uani 1 1 d . . . H22A H 0.8958 0.8033 0.5326 0.047 Uiso 1 1 calc R . . C8 C 1.0696(4) 0.9891(4) 0.8592(4) 0.0310(11) Uani 1 1 d . . . C24 C 0.8752(6) 0.7903(6) 0.3675(7) 0.063(2) Uani 1 1 d . . . H24A H 0.8370 0.8494 0.3534 0.095 Uiso 1 1 calc R . . H24B H 0.8484 0.7425 0.3143 0.095 Uiso 1 1 calc R . . H24C H 0.9465 0.8019 0.3628 0.095 Uiso 1 1 calc R . . N1 N 1.0546(3) 0.7428(3) 0.6230(3) 0.0251(8) Uani 1 1 d . . . C9 C 0.9335(5) 0.9260(4) 0.9415(5) 0.0355(12) Uani 1 1 d . . . H9A H 0.8737 0.8853 0.9195 0.043 Uiso 1 1 calc R . . H9B H 0.9097 0.9922 0.9460 0.043 Uiso 1 1 calc R . . C21 C 1.2352(5) 0.4963(5) 0.6599(6) 0.0505(16) Uani 1 1 d . . . H21A H 1.2925 0.4954 0.7181 0.076 Uiso 1 1 calc R . . H21B H 1.2581 0.5175 0.5936 0.076 Uiso 1 1 calc R . . H21C H 1.2067 0.4323 0.6496 0.076 Uiso 1 1 calc R . . C10 C 0.9864(5) 0.8942(4) 1.0529(5) 0.0395(13) Uani 1 1 d . . . H10A H 1.0547 0.9226 1.0660 0.047 Uiso 1 1 calc R . . H10B H 0.9481 0.9192 1.1081 0.047 Uiso 1 1 calc R . . C11 C 0.9960(5) 0.7888(5) 1.0661(6) 0.0467(15) Uani 1 1 d . . . H11A H 1.0292 0.7624 1.0075 0.056 Uiso 1 1 calc R . . H11C H 0.9279 0.7603 1.0605 0.056 Uiso 1 1 calc R . . C12 C 1.0583(6) 0.7617(5) 1.1755(5) 0.0520(16) Uani 1 1 d . . . H12D H 1.0630 0.6925 1.1815 0.078 Uiso 1 1 calc R . . H12A H 1.0249 0.7868 1.2336 0.078 Uiso 1 1 calc R . . H12B H 1.1262 0.7888 1.1807 0.078 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 0.02421(17) 0.02121(16) 0.02547(17) -0.00137(15) 0.00231(12) -0.00561(16) N2 0.027(2) 0.0166(17) 0.030(2) 0.0023(15) -0.0006(16) -0.0039(15) N3 0.030(2) 0.027(2) 0.032(2) -0.0058(18) 0.0024(18) -0.0029(17) C2 0.024(2) 0.023(2) 0.030(3) -0.0011(19) 0.0007(19) -0.0003(18) C3 0.028(3) 0.025(2) 0.027(2) 0.0017(19) -0.0009(19) -0.0041(19) C1 0.032(3) 0.028(2) 0.039(3) 0.003(2) 0.011(2) -0.002(2) C4 0.036(3) 0.028(2) 0.034(3) 0.007(2) 0.003(2) -0.006(2) Cl1 0.0389(7) 0.0350(7) 0.0422(7) -0.0066(6) 0.0142(6) -0.0180(6) O1 0.050(3) 0.0280(19) 0.037(2) -0.0073(16) 0.0036(18) -0.0069(17) C23 0.053(4) 0.072(4) 0.059(4) 0.014(3) 0.018(3) 0.015(3) C6 0.029(3) 0.020(2) 0.035(3) 0.0021(19) -0.008(2) -0.0057(19) C5 0.025(3) 0.032(3) 0.039(3) 0.009(2) -0.003(2) -0.010(2) C19 0.036(3) 0.025(2) 0.039(3) -0.001(2) 0.005(2) -0.002(2) C17 0.032(3) 0.047(3) 0.035(3) -0.010(2) 0.002(2) -0.010(2) C14 0.028(3) 0.028(2) 0.031(3) -0.002(2) 0.007(2) -0.006(2) C13 0.026(3) 0.028(2) 0.025(2) -0.007(2) 0.009(2) -0.006(2) C18 0.027(3) 0.037(3) 0.028(3) -0.006(2) 0.002(2) -0.006(2) C20 0.063(4) 0.060(4) 0.033(3) 0.000(3) 0.007(3) -0.002(3) C7 0.029(3) 0.025(2) 0.027(2) 0.0025(19) -0.0040(19) -0.0060(19) C15 0.040(3) 0.027(2) 0.043(3) -0.007(2) 0.016(3) -0.005(2) C16 0.040(3) 0.034(3) 0.042(3) -0.019(2) 0.014(3) -0.019(2) C22 0.030(3) 0.043(3) 0.040(3) -0.006(3) -0.010(2) -0.006(2) C8 0.032(3) 0.028(2) 0.030(3) -0.005(2) -0.002(2) -0.003(2) C24 0.052(5) 0.067(5) 0.073(5) 0.025(4) 0.019(4) 0.007(4) N1 0.027(2) 0.026(2) 0.022(2) -0.0001(16) 0.0029(16) -0.0057(16) C9 0.041(3) 0.030(3) 0.037(3) -0.007(2) 0.013(2) -0.002(2) C21 0.043(4) 0.052(4) 0.055(4) -0.005(3) 0.001(3) 0.007(3) C10 0.044(3) 0.045(3) 0.031(3) -0.010(3) 0.012(2) -0.002(3) C11 0.040(3) 0.042(3) 0.057(4) 0.003(3) 0.003(3) -0.003(3) C12 0.063(4) 0.054(4) 0.037(3) 0.002(3) 0.004(3) 0.004(3) _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 N2 1.932(4) . ? Pd1 N3 2.018(4) . ? Pd1 N1 2.088(4) . ? Pd1 Cl1 2.2951(13) . ? N2 C7 1.334(6) . ? N2 C3 1.346(7) . ? N3 C8 1.336(7) . ? N3 C9 1.472(7) . ? C2 N1 1.301(6) . ? C2 C3 1.480(7) . ? C2 C1 1.489(7) . ? C3 C4 1.382(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 C5 1.393(8) . ? C4 H4A 0.9500 . ? O1 C8 1.255(6) . ? C23 C22 1.516(11) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C6 C5 1.391(8) . ? C6 C7 1.395(7) . ? C6 H6A 0.9500 . ? C5 H5A 0.9500 . ? C19 C21 1.493(8) . ? C19 C20 1.517(8) . ? C19 C14 1.525(8) . ? C19 H19A 1.0000 . ? C17 C16 1.380(9) . ? C17 C18 1.406(8) . ? C17 H17A 0.9500 . ? C14 C15 1.383(7) . ? C14 C13 1.405(7) . ? C13 C18 1.378(8) . ? C13 N1 1.436(6) . ? C18 C22 1.532(9) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C7 C8 1.495(8) . ? C15 C16 1.374(9) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C22 C24 1.534(10) . ? C22 H22A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C9 C10 1.543(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C10 C11 1.497(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.550(9) . ? C11 H11A 0.9900 . ? C11 H11C 0.9900 . ? C12 H12D 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pd1 N3 81.19(18) . . ? N2 Pd1 N1 79.02(16) . . ? N3 Pd1 N1 160.20(16) . . ? N2 Pd1 Cl1 179.93(15) . . ? N3 Pd1 Cl1 98.87(13) . . ? N1 Pd1 Cl1 100.93(12) . . ? C7 N2 C3 123.7(4) . . ? C7 N2 Pd1 117.1(3) . . ? C3 N2 Pd1 119.2(3) . . ? C8 N3 C9 117.5(4) . . ? C8 N3 Pd1 114.2(4) . . ? C9 N3 Pd1 128.2(3) . . ? N1 C2 C3 115.9(4) . . ? N1 C2 C1 124.6(4) . . ? C3 C2 C1 119.5(4) . . ? N2 C3 C4 119.2(5) . . ? N2 C3 C2 112.3(4) . . ? C4 C3 C2 128.5(5) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 C6 C7 118.6(5) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C6 C5 C4 120.3(5) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C21 C19 C20 111.5(5) . . ? C21 C19 C14 113.9(5) . . ? C20 C19 C14 109.1(5) . . ? C21 C19 H19A 107.4 . . ? C20 C19 H19A 107.4 . . ? C14 C19 H19A 107.4 . . ? C16 C17 C18 121.2(6) . . ? C16 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? C15 C14 C13 117.0(5) . . ? C15 C14 C19 120.6(5) . . ? C13 C14 C19 122.4(5) . . ? C18 C13 C14 122.9(5) . . ? C18 C13 N1 117.4(5) . . ? C14 C13 N1 119.7(5) . . ? C13 C18 C17 117.2(6) . . ? C13 C18 C22 123.6(5) . . ? C17 C18 C22 119.2(5) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C7 C6 119.2(5) . . ? N2 C7 C8 113.8(4) . . ? C6 C7 C8 126.9(5) . . ? C16 C15 C14 122.0(5) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15 C16 C17 119.5(5) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C23 C22 C18 112.9(6) . . ? C23 C22 C24 109.9(6) . . ? C18 C22 C24 111.1(6) . . ? C23 C22 H22A 107.6 . . ? C18 C22 H22A 107.6 . . ? C24 C22 H22A 107.6 . . ? O1 C8 N3 126.2(5) . . ? O1 C8 C7 120.1(5) . . ? N3 C8 C7 113.7(4) . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2 N1 C13 119.3(4) . . ? C2 N1 Pd1 113.5(3) . . ? C13 N1 Pd1 127.2(3) . . ? N3 C9 C10 111.9(5) . . ? N3 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N3 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 C10 C9 114.2(5) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 111.6(6) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11C 109.3 . . ? C12 C11 H11C 109.3 . . ? H11A C11 H11C 108.0 . . ? C11 C12 H12D 109.5 . . ? C11 C12 H12A 109.5 . . ? H12D C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12D C12 H12B 109.5 . . ? H12A C12 H12B 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 N3 Pd1 N2 C7 -0.5(4) . . . . ? N1 Pd1 N2 C7 179.0(4) . . . . ? Cl1 Pd1 N2 C7 139(100) . . . . ? N3 Pd1 N2 C3 179.5(4) . . . . ? N1 Pd1 N2 C3 -0.9(4) . . . . ? Cl1 Pd1 N2 C3 -41(100) . . . . ? N2 Pd1 N3 C8 0.6(4) . . . . ? N1 Pd1 N3 C8 -0.7(8) . . . . ? Cl1 Pd1 N3 C8 -179.4(4) . . . . ? N2 Pd1 N3 C9 -177.5(5) . . . . ? N1 Pd1 N3 C9 -178.7(4) . . . . ? Cl1 Pd1 N3 C9 2.6(5) . . . . ? C7 N2 C3 C4 2.2(7) . . . . ? Pd1 N2 C3 C4 -177.8(4) . . . . ? C7 N2 C3 C2 -178.1(4) . . . . ? Pd1 N2 C3 C2 1.8(6) . . . . ? N1 C2 C3 N2 -2.0(7) . . . . ? C1 C2 C3 N2 178.4(4) . . . . ? N1 C2 C3 C4 177.6(5) . . . . ? C1 C2 C3 C4 -2.0(8) . . . . ? N2 C3 C4 C5 -2.0(8) . . . . ? C2 C3 C4 C5 178.4(5) . . . . ? C7 C6 C5 C4 0.2(8) . . . . ? C3 C4 C5 C6 0.9(8) . . . . ? C21 C19 C14 C15 39.5(7) . . . . ? C20 C19 C14 C15 -85.7(6) . . . . ? C21 C19 C14 C13 -141.6(5) . . . . ? C20 C19 C14 C13 93.2(6) . . . . ? C15 C14 C13 C18 4.5(8) . . . . ? C19 C14 C13 C18 -174.4(5) . . . . ? C15 C14 C13 N1 -174.5(4) . . . . ? C19 C14 C13 N1 6.6(7) . . . . ? C14 C13 C18 C17 -5.2(8) . . . . ? N1 C13 C18 C17 173.9(5) . . . . ? C14 C13 C18 C22 177.0(5) . . . . ? N1 C13 C18 C22 -3.9(8) . . . . ? C16 C17 C18 C13 2.5(8) . . . . ? C16 C17 C18 C22 -179.6(5) . . . . ? C3 N2 C7 C6 -1.1(7) . . . . ? Pd1 N2 C7 C6 179.0(4) . . . . ? C3 N2 C7 C8 -179.7(5) . . . . ? Pd1 N2 C7 C8 0.4(6) . . . . ? C5 C6 C7 N2 -0.2(8) . . . . ? C5 C6 C7 C8 178.2(5) . . . . ? C13 C14 C15 C16 -1.1(8) . . . . ? C19 C14 C15 C16 177.8(5) . . . . ? C14 C15 C16 C17 -1.3(9) . . . . ? C18 C17 C16 C15 0.6(9) . . . . ? C13 C18 C22 C23 -128.5(7) . . . . ? C17 C18 C22 C23 53.7(8) . . . . ? C13 C18 C22 C24 107.5(7) . . . . ? C17 C18 C22 C24 -70.3(7) . . . . ? C9 N3 C8 O1 -1.6(8) . . . . ? Pd1 N3 C8 O1 -179.9(5) . . . . ? C9 N3 C8 C7 177.7(5) . . . . ? Pd1 N3 C8 C7 -0.6(6) . . . . ? N2 C7 C8 O1 179.5(5) . . . . ? C6 C7 C8 O1 1.0(9) . . . . ? N2 C7 C8 N3 0.1(7) . . . . ? C6 C7 C8 N3 -178.3(5) . . . . ? C3 C2 N1 C13 -178.8(4) . . . . ? C1 C2 N1 C13 0.7(8) . . . . ? C3 C2 N1 Pd1 1.4(6) . . . . ? C1 C2 N1 Pd1 -179.1(4) . . . . ? C18 C13 N1 C2 -101.6(6) . . . . ? C14 C13 N1 C2 77.5(6) . . . . ? C18 C13 N1 Pd1 78.2(6) . . . . ? C14 C13 N1 Pd1 -102.7(5) . . . . ? N2 Pd1 N1 C2 -0.3(4) . . . . ? N3 Pd1 N1 C2 1.0(7) . . . . ? Cl1 Pd1 N1 C2 179.6(3) . . . . ? N2 Pd1 N1 C13 179.9(4) . . . . ? N3 Pd1 N1 C13 -178.8(5) . . . . ? Cl1 Pd1 N1 C13 -0.2(4) . . . . ? C8 N3 C9 C10 -77.7(6) . . . . ? Pd1 N3 C9 C10 100.3(5) . . . . ? N3 C9 C10 C11 -77.6(6) . . . . ? C9 C10 C11 C12 174.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.917 _refine_diff_density_min -0.718 _refine_diff_density_rms 0.146 #==END data_C4 _database_code_depnum_ccdc_archive 'CCDC 828936' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 Br Cl N3 O Pd' _chemical_formula_weight 543.18 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' Br Br -0.2901 2.4595 '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' 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 9.833(2) _cell_length_b 10.801(2) _cell_length_c 11.479(2) _cell_angle_alpha 117.58(3) _cell_angle_beta 94.67(3) _cell_angle_gamma 90.15(3) _cell_volume 1075.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9726 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 27.33 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 2.858 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR by T. Higashi, March, 2001' _exptl_absorpt_correction_T_min 0.4173 _exptl_absorpt_correction_T_max 0.6734 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid IP' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9726 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _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 2.01 _diffrn_reflns_theta_max 27.33 _reflns_number_total 4746 _reflns_number_gt 4057 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'rapid auto(Rigaku 2001)' _computing_cell_refinement 'rapid auto(Rigaku 2001)' _computing_data_reduction 'rapid auto(Rigaku 2001)' _computing_structure_solution 'Shelxs-97(Sheldrick, 1997)' _computing_structure_refinement 'Shelxl-97(Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0663P)^2^+0.3914P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4746 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Pd Pd 0.28486(2) 0.84685(3) 0.55274(3) 0.03833(10) Uani 1 1 d . . . Br Br -0.26623(5) 0.33400(5) 0.10487(6) 0.07681(18) Uani 1 1 d . . . Cl Cl 0.06352(9) 0.86396(11) 0.60500(11) 0.0584(3) Uani 1 1 d . . . O O 0.5818(3) 1.1313(3) 0.7953(3) 0.0630(8) Uani 1 1 d . . . N1 N 0.2616(3) 0.6753(3) 0.3690(3) 0.0405(6) Uani 1 1 d . . . N2 N 0.4705(3) 0.8298(3) 0.5058(3) 0.0407(6) Uani 1 1 d . . . N3 N 0.3731(3) 1.0111(3) 0.7140(3) 0.0476(7) Uani 1 1 d . . . C1 C 0.3835(4) 0.5301(5) 0.1740(4) 0.0610(11) Uani 1 1 d . . . H1A H 0.2954 0.4841 0.1362 0.092 Uiso 1 1 calc R . . H1B H 0.4467 0.4633 0.1759 0.092 Uiso 1 1 calc R . . H1C H 0.4153 0.5703 0.1216 0.092 Uiso 1 1 calc R . . C2 C 0.3726(4) 0.6423(4) 0.3109(4) 0.0440(8) Uani 1 1 d . . . C3 C 0.4973(3) 0.7262(4) 0.3889(4) 0.0418(8) Uani 1 1 d . . . C4 C 0.6305(4) 0.7086(4) 0.3562(4) 0.0504(9) Uani 1 1 d . . . H4A H 0.6514 0.6360 0.2763 0.061 Uiso 1 1 calc R . . C5 C 0.7322(4) 0.8007(4) 0.4441(4) 0.0516(9) Uani 1 1 d . . . H5A H 0.8222 0.7905 0.4231 0.062 Uiso 1 1 calc R . . C6 C 0.7004(4) 0.9078(4) 0.5628(4) 0.0491(9) Uani 1 1 d . . . H6A H 0.7686 0.9700 0.6222 0.059 Uiso 1 1 calc R . . C7 C 0.5654(4) 0.9214(4) 0.5924(4) 0.0420(7) Uani 1 1 d . . . C8 C 0.5076(4) 1.0326(4) 0.7129(4) 0.0463(8) Uani 1 1 d . . . C9 C 0.3050(4) 1.1063(4) 0.8282(4) 0.0554(10) Uani 1 1 d . . . H9A H 0.2146 1.1222 0.7986 0.066 Uiso 1 1 calc R . . H9B H 0.3561 1.1955 0.8720 0.066 Uiso 1 1 calc R . . C10 C 0.2926(7) 1.0519(6) 0.9234(5) 0.0854(17) Uani 1 1 d . . . H10A H 0.3835 1.0458 0.9595 0.103 Uiso 1 1 calc R . . H10B H 0.2516 0.9578 0.8764 0.103 Uiso 1 1 calc R . . C11 C 0.2105(8) 1.1364(6) 1.0345(6) 0.098(2) Uani 1 1 d . . . H11A H 0.2561 1.2278 1.0862 0.118 Uiso 1 1 calc R . . H11B H 0.1225 1.1498 0.9983 0.118 Uiso 1 1 calc R . . C12 C 0.1876(11) 1.0776(9) 1.1218(8) 0.145(4) Uani 1 1 d . . . H12A H 0.1558 1.1484 1.2017 0.218 Uiso 1 1 calc R . . H12B H 0.2716 1.0437 1.1424 0.218 Uiso 1 1 calc R . . H12C H 0.1203 1.0018 1.0794 0.218 Uiso 1 1 calc R . . C13 C 0.1354(3) 0.5956(4) 0.3054(3) 0.0409(7) Uani 1 1 d . . . C14 C 0.0494(4) 0.6329(4) 0.2264(4) 0.0433(8) Uani 1 1 d . . . C15 C -0.0709(4) 0.5530(4) 0.1670(4) 0.0496(9) Uani 1 1 d . . . H15A H -0.1296 0.5736 0.1111 0.059 Uiso 1 1 calc R . . C16 C -0.1029(4) 0.4435(4) 0.1910(4) 0.0501(9) Uani 1 1 d . . . C17 C -0.0196(4) 0.4097(4) 0.2723(4) 0.0537(10) Uani 1 1 d . . . H17A H -0.0448 0.3359 0.2876 0.064 Uiso 1 1 calc R . . C18 C 0.1028(4) 0.4858(4) 0.3322(4) 0.0476(8) Uani 1 1 d . . . C19 C 0.0816(4) 0.7572(4) 0.2059(5) 0.0585(10) Uani 1 1 d . . . H19A H 0.1772 0.7614 0.1958 0.088 Uiso 1 1 calc R . . H19B H 0.0590 0.8411 0.2809 0.088 Uiso 1 1 calc R . . H19C H 0.0292 0.7484 0.1279 0.088 Uiso 1 1 calc R . . C20 C 0.1952(5) 0.4522(6) 0.4225(6) 0.0704(13) Uani 1 1 d . . . H20A H 0.1527 0.3794 0.4346 0.106 Uiso 1 1 calc R . . H20B H 0.2122 0.5341 0.5063 0.106 Uiso 1 1 calc R . . H20C H 0.2800 0.4214 0.3847 0.106 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 Pd 0.02958(14) 0.03975(16) 0.03992(16) 0.01405(12) 0.00101(10) -0.00265(10) Br 0.0434(2) 0.0497(3) 0.1078(4) 0.0138(3) -0.0057(2) -0.01524(19) Cl 0.0344(4) 0.0653(6) 0.0617(6) 0.0170(5) 0.0096(4) -0.0019(4) O 0.0506(16) 0.0554(17) 0.0616(18) 0.0115(14) -0.0087(13) -0.0151(13) N1 0.0311(14) 0.0396(15) 0.0436(16) 0.0139(13) -0.0003(12) -0.0045(11) N2 0.0309(13) 0.0430(16) 0.0446(16) 0.0182(13) -0.0011(11) -0.0027(12) N3 0.0430(16) 0.0452(17) 0.0431(17) 0.0112(14) 0.0009(13) -0.0058(13) C1 0.045(2) 0.057(2) 0.053(2) 0.0023(19) 0.0062(17) -0.0037(18) C2 0.0358(17) 0.0439(19) 0.047(2) 0.0166(16) 0.0011(14) -0.0019(14) C3 0.0322(16) 0.0415(18) 0.0459(19) 0.0157(16) 0.0005(14) -0.0008(14) C4 0.0361(18) 0.059(2) 0.052(2) 0.0216(19) 0.0079(16) 0.0035(17) C5 0.0297(17) 0.062(2) 0.062(2) 0.029(2) 0.0018(16) -0.0013(16) C6 0.0324(17) 0.055(2) 0.058(2) 0.0271(19) -0.0051(15) -0.0084(16) C7 0.0365(17) 0.0440(18) 0.0443(19) 0.0206(16) -0.0029(14) -0.0051(14) C8 0.0428(19) 0.048(2) 0.045(2) 0.0210(17) -0.0047(15) -0.0034(16) C9 0.052(2) 0.046(2) 0.051(2) 0.0082(18) 0.0076(18) -0.0013(17) C10 0.122(5) 0.077(3) 0.060(3) 0.030(3) 0.029(3) 0.022(3) C11 0.140(6) 0.076(4) 0.080(4) 0.032(3) 0.043(4) 0.022(4) C12 0.217(10) 0.150(7) 0.104(6) 0.078(6) 0.082(6) 0.082(7) C13 0.0325(16) 0.0394(17) 0.0406(18) 0.0096(15) 0.0052(13) -0.0031(13) C14 0.0336(16) 0.0416(18) 0.0450(19) 0.0123(15) 0.0020(14) -0.0020(14) C15 0.0352(17) 0.045(2) 0.055(2) 0.0127(17) -0.0022(15) -0.0028(15) C16 0.0314(16) 0.0398(18) 0.057(2) 0.0037(16) 0.0034(15) -0.0061(14) C17 0.049(2) 0.0402(19) 0.066(3) 0.0183(19) 0.0112(19) -0.0051(16) C18 0.0435(19) 0.0438(19) 0.051(2) 0.0179(17) 0.0055(16) -0.0018(16) C19 0.042(2) 0.055(2) 0.078(3) 0.032(2) -0.0061(19) -0.0070(18) C20 0.068(3) 0.075(3) 0.079(3) 0.046(3) -0.002(2) -0.006(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 Pd N2 1.930(3) . ? Pd N3 2.004(3) . ? Pd N1 2.058(3) . ? Pd Cl 2.2898(11) . ? Br C16 1.898(4) . ? O C8 1.230(5) . ? N1 C2 1.290(5) . ? N1 C13 1.442(4) . ? N2 C7 1.332(4) . ? N2 C3 1.338(5) . ? N3 C8 1.344(5) . ? N3 C9 1.457(5) . ? C1 C2 1.488(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.480(5) . ? C3 C4 1.381(5) . ? C4 C5 1.381(6) . ? C4 H4A 0.9300 . ? C5 C6 1.380(6) . ? C5 H5A 0.9300 . ? C6 C7 1.389(5) . ? C6 H6A 0.9300 . ? C7 C8 1.507(5) . ? C9 C10 1.474(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.485(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.443(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.385(5) . ? C13 C18 1.398(5) . ? C14 C15 1.388(5) . ? C14 C19 1.503(5) . ? C15 C16 1.375(6) . ? C15 H15A 0.9300 . ? C16 C17 1.366(6) . ? C17 C18 1.390(5) . ? C17 H17A 0.9300 . ? C18 C20 1.493(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pd N3 80.86(13) . . ? N2 Pd N1 79.40(12) . . ? N3 Pd N1 160.23(13) . . ? N2 Pd Cl 179.02(9) . . ? N3 Pd Cl 100.11(10) . . ? N1 Pd Cl 99.62(9) . . ? C2 N1 C13 120.7(3) . . ? C2 N1 Pd 113.9(2) . . ? C13 N1 Pd 125.4(2) . . ? C7 N2 C3 123.5(3) . . ? C7 N2 Pd 118.0(3) . . ? C3 N2 Pd 118.5(2) . . ? C8 N3 C9 118.8(3) . . ? C8 N3 Pd 115.1(3) . . ? C9 N3 Pd 126.1(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 115.8(3) . . ? N1 C2 C1 125.4(3) . . ? C3 C2 C1 118.7(3) . . ? N2 C3 C4 119.3(3) . . ? N2 C3 C2 112.2(3) . . ? C4 C3 C2 128.6(3) . . ? C3 C4 C5 119.0(4) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C7 119.1(3) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? N2 C7 C6 118.9(3) . . ? N2 C7 C8 113.1(3) . . ? C6 C7 C8 128.0(3) . . ? O C8 N3 127.2(4) . . ? O C8 C7 120.0(4) . . ? N3 C8 C7 112.8(3) . . ? N3 C9 C10 112.4(4) . . ? N3 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C11 115.0(5) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 115.4(6) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 122.7(3) . . ? C14 C13 N1 119.9(3) . . ? C18 C13 N1 117.3(3) . . ? C13 C14 C15 117.9(4) . . ? C13 C14 C19 122.1(3) . . ? C15 C14 C19 120.0(3) . . ? C16 C15 C14 119.7(4) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C17 C16 C15 122.0(3) . . ? C17 C16 Br 119.4(3) . . ? C15 C16 Br 118.5(3) . . ? C16 C17 C18 120.0(4) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C13 117.5(4) . . ? C17 C18 C20 121.2(4) . . ? C13 C18 C20 121.4(4) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.33 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.229 _refine_diff_density_min -1.058 _refine_diff_density_rms 0.132 #==END data_C6 _database_code_depnum_ccdc_archive 'CCDC 828937' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 Cl N3 O Pd' _chemical_formula_weight 548.43 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 Rhombohedral _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 31.280(4) _cell_length_b 31.280(4) _cell_length_c 14.424(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 12222(3) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 34533 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5112 _exptl_absorpt_coefficient_mu 0.803 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR by T. Higashi, March, 2001' _exptl_absorpt_correction_T_min 0.4173 _exptl_absorpt_correction_T_max 0.6734 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid IP' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 34533 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3132 _reflns_number_gt 2424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'rapid auto(Rigaku 2001)' _computing_cell_refinement 'rapid auto(Rigaku 2001)' _computing_data_reduction 'rapid auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97(Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. 'TWIN' was used to refine a racemic twin of twinning. The atoms of "C12, C13, C16, C26" were isotropic for their severe disorder. ; _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^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(7) _refine_ls_number_reflns 3132 _refine_ls_number_parameters 270 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd 0.442506(19) 0.347704(17) 0.84033(4) 0.04871(15) Uani 1 1 d . . . Cl Cl 0.41501(11) 0.26528(7) 0.83560(14) 0.0942(9) Uani 1 1 d . . . N2 N 0.46462(19) 0.41685(18) 0.8438(3) 0.0453(12) Uani 1 1 d . . . N1 N 0.4612(2) 0.3631(2) 0.9797(4) 0.0511(13) Uani 1 1 d . . . N3 N 0.4327(2) 0.3574(2) 0.7059(4) 0.0548(14) Uani 1 1 d . . . O O 0.4455(2) 0.42001(19) 0.6045(3) 0.0698(14) Uani 1 1 d . . . C2 C 0.4781(3) 0.4089(2) 1.0022(4) 0.0509(15) Uani 1 1 d . . . C3 C 0.4800(2) 0.4414(2) 0.9247(4) 0.0456(13) Uani 1 1 d . . . C8 C 0.4459(3) 0.4036(3) 0.6839(5) 0.0543(16) Uani 1 1 d . . . C7 C 0.4625(2) 0.4376(2) 0.7654(4) 0.0472(14) Uani 1 1 d . . . C22 C 0.4174(3) 0.3117(3) 1.1127(5) 0.0609(19) Uani 1 1 d . . . C5 C 0.4925(3) 0.5134(2) 0.8471(5) 0.0618(18) Uani 1 1 d . . . H5A H 0.5016 0.5466 0.8483 0.074 Uiso 1 1 calc R . . C4 C 0.4949(3) 0.4906(2) 0.9283(4) 0.0557(16) Uani 1 1 d . . . H4A H 0.5063 0.5083 0.9833 0.067 Uiso 1 1 calc R . . C9 C 0.4155(4) 0.3204(3) 0.6330(6) 0.076(3) Uani 1 1 d . . . H9A H 0.4029 0.3312 0.5822 0.091 Uiso 1 1 calc R . . H9B H 0.3883 0.2899 0.6569 0.091 Uiso 1 1 calc R . . C17 C 0.4567(3) 0.3285(2) 1.0511(5) 0.0513(16) Uani 1 1 d . . . C6 C 0.4768(3) 0.4875(2) 0.7647(5) 0.0560(17) Uani 1 1 d . . . H6A H 0.4758 0.5029 0.7104 0.067 Uiso 1 1 calc R . . C19 C 0.4862(4) 0.2799(3) 1.1216(6) 0.079(2) Uani 1 1 d . . . H19A H 0.5087 0.2687 1.1251 0.094 Uiso 1 1 calc R . . C20 C 0.4481(4) 0.2631(3) 1.1856(6) 0.080(3) Uani 1 1 d . . . H20A H 0.4453 0.2409 1.2314 0.096 Uiso 1 1 calc R . . C18 C 0.4915(3) 0.3132(3) 1.0518(5) 0.068(2) Uani 1 1 d . . . C1 C 0.4951(3) 0.4304(3) 1.0954(5) 0.072(2) Uani 1 1 d . . . H1A H 0.4918 0.4052 1.1375 0.109 Uiso 1 1 calc R . . H1B H 0.4753 0.4441 1.1169 0.109 Uiso 1 1 calc R . . H1C H 0.5290 0.4560 1.0924 0.109 Uiso 1 1 calc R . . C21 C 0.4156(3) 0.2788(3) 1.1815(5) 0.073(2) Uani 1 1 d . . . H21A H 0.3907 0.2676 1.2259 0.087 Uiso 1 1 calc R . . C25 C 0.5324(4) 0.3320(4) 0.9833(8) 0.091(3) Uani 1 1 d . . . H25A H 0.5178 0.3281 0.9223 0.109 Uiso 1 1 calc R . . H25B H 0.5530 0.3672 0.9940 0.109 Uiso 1 1 calc R . . C23 C 0.3779(4) 0.3258(4) 1.1076(6) 0.081(2) Uani 1 1 d . . . H23A H 0.3628 0.3214 1.1682 0.098 Uiso 1 1 calc R . . H23B H 0.3930 0.3605 1.0916 0.098 Uiso 1 1 calc R . . C26 C 0.5651(7) 0.3110(7) 0.9792(14) 0.192(8) Uiso 1 1 d . . . H26A H 0.5896 0.3275 0.9319 0.289 Uiso 1 1 calc R . . H26B H 0.5461 0.2764 0.9650 0.289 Uiso 1 1 calc R . . H26C H 0.5812 0.3153 1.0380 0.289 Uiso 1 1 calc R . . C11 C 0.4930(7) 0.3450(5) 0.5348(9) 0.150(6) Uani 1 1 d . . . H11A H 0.5013 0.3775 0.5576 0.180 Uiso 1 1 calc R . . H11B H 0.5221 0.3419 0.5431 0.180 Uiso 1 1 calc R . . C10 C 0.4556(5) 0.3097(4) 0.5949(7) 0.098(3) Uani 1 1 d . . . H10A H 0.4720 0.3049 0.6476 0.118 Uiso 1 1 calc R . . H10B H 0.4388 0.2785 0.5619 0.118 Uiso 1 1 calc R . . C24 C 0.3392(4) 0.2967(5) 1.0395(8) 0.103(3) Uani 1 1 d . . . H24A H 0.3153 0.3075 1.0388 0.155 Uiso 1 1 calc R . . H24B H 0.3232 0.2624 1.0560 0.155 Uiso 1 1 calc R . . H24C H 0.3537 0.3012 0.9791 0.155 Uiso 1 1 calc R . . C14 C 0.5606(8) 0.3690(6) 0.3314(13) 0.170(8) Uani 1 1 d . . . H14A H 0.5431 0.3359 0.3060 0.204 Uiso 1 1 calc R . . H14B H 0.5823 0.3697 0.3801 0.204 Uiso 1 1 calc R . . C12 C 0.4853(9) 0.3448(9) 0.4429(17) 0.218(9) Uiso 1 1 d . . . H12A H 0.4564 0.3482 0.4357 0.261 Uiso 1 1 calc R . . H12B H 0.4759 0.3118 0.4216 0.261 Uiso 1 1 calc R . . C13 C 0.5249(8) 0.3818(8) 0.3703(14) 0.186(8) Uiso 1 1 d . . . H13A H 0.5070 0.3857 0.3191 0.223 Uiso 1 1 calc R . . H13B H 0.5434 0.4138 0.4001 0.223 Uiso 1 1 calc R . . C15 C 0.5905(7) 0.4050(7) 0.2567(10) 0.154(6) Uani 1 1 d . . . H15A H 0.5694 0.4021 0.2051 0.185 Uiso 1 1 calc R . . H15B H 0.6057 0.4385 0.2804 0.185 Uiso 1 1 calc R . . C16 C 0.6294(10) 0.3938(10) 0.2252(17) 0.234(11) Uiso 1 1 d . . . H16A H 0.6494 0.4171 0.1785 0.351 Uiso 1 1 calc R . . H16B H 0.6140 0.3610 0.2000 0.351 Uiso 1 1 calc R . . H16C H 0.6497 0.3960 0.2770 0.351 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 Pd 0.0627(3) 0.0288(2) 0.0478(2) 0.0052(2) 0.0111(2) 0.0178(2) Cl 0.161(2) 0.0325(9) 0.0691(12) 0.0078(8) 0.0290(14) 0.0340(12) N2 0.049(3) 0.034(3) 0.050(3) 0.004(2) 0.001(2) 0.019(2) N1 0.065(4) 0.036(3) 0.051(3) 0.010(3) 0.010(3) 0.025(3) N3 0.065(4) 0.038(3) 0.052(3) -0.003(2) 0.004(3) 0.019(3) O 0.088(4) 0.060(3) 0.056(3) 0.005(2) -0.011(3) 0.033(3) C2 0.060(4) 0.042(3) 0.048(3) 0.005(3) 0.009(3) 0.023(3) C3 0.047(3) 0.034(3) 0.048(3) -0.002(2) -0.001(3) 0.015(3) C8 0.060(4) 0.048(4) 0.050(3) 0.003(3) 0.002(3) 0.024(3) C7 0.045(3) 0.040(3) 0.053(3) 0.005(3) 0.006(3) 0.018(3) C22 0.072(5) 0.043(4) 0.052(4) 0.003(3) 0.004(3) 0.017(4) C5 0.074(5) 0.033(3) 0.073(4) 0.003(3) 0.005(4) 0.023(3) C4 0.069(4) 0.036(3) 0.055(4) 0.000(3) -0.002(3) 0.020(3) C9 0.093(6) 0.046(4) 0.061(4) -0.005(4) -0.006(5) 0.014(4) C17 0.069(4) 0.038(3) 0.044(3) 0.011(3) 0.010(3) 0.025(3) C6 0.068(5) 0.039(3) 0.060(4) 0.011(3) 0.004(4) 0.026(3) C19 0.095(6) 0.058(5) 0.082(5) 0.017(4) -0.006(5) 0.038(5) C20 0.100(7) 0.053(4) 0.074(5) 0.021(4) -0.010(5) 0.028(5) C18 0.082(5) 0.043(4) 0.070(4) 0.013(3) 0.007(4) 0.025(4) C1 0.094(6) 0.047(4) 0.058(4) -0.002(3) -0.009(4) 0.021(4) C21 0.086(6) 0.049(4) 0.050(4) 0.011(3) 0.013(4) 0.009(4) C25 0.094(7) 0.097(7) 0.109(7) 0.033(6) 0.028(6) 0.067(6) C23 0.090(6) 0.073(5) 0.075(5) 0.009(4) 0.032(5) 0.037(5) C11 0.200(17) 0.107(10) 0.104(9) -0.016(8) 0.002(10) 0.047(11) C10 0.130(9) 0.075(6) 0.078(6) -0.018(5) 0.011(6) 0.043(6) C24 0.095(7) 0.121(9) 0.109(7) -0.008(7) -0.008(7) 0.065(7) C14 0.206(19) 0.114(12) 0.155(13) -0.019(11) -0.084(14) 0.053(12) C15 0.158(14) 0.148(14) 0.105(9) 0.023(10) -0.015(10) 0.038(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd N2 1.914(5) . ? Pd N3 2.010(6) . ? Pd N1 2.082(6) . ? Pd Cl 2.2746(18) . ? N2 C7 1.321(8) . ? N2 C3 1.346(7) . ? N1 C2 1.295(8) . ? N1 C17 1.447(8) . ? N3 C8 1.326(9) . ? N3 C9 1.454(10) . ? O C8 1.258(8) . ? C2 C1 1.479(10) . ? C2 C3 1.493(9) . ? C3 C4 1.369(9) . ? C8 C7 1.494(9) . ? C7 C6 1.391(9) . ? C22 C17 1.388(11) . ? C22 C21 1.410(11) . ? C22 C23 1.510(13) . ? C5 C6 1.382(10) . ? C5 C4 1.392(9) . ? C9 C10 1.551(15) . ? C17 C18 1.395(11) . ? C19 C20 1.386(14) . ? C19 C18 1.396(11) . ? C20 C21 1.335(13) . ? C18 C25 1.484(12) . ? C25 C26 1.469(18) . ? C23 C24 1.468(14) . ? C11 C12 1.35(2) . ? C11 C10 1.431(17) . ? C14 C13 1.47(2) . ? C14 C15 1.50(2) . ? C12 C13 1.59(3) . ? C15 C16 1.50(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pd N3 81.4(2) . . ? N2 Pd N1 79.2(2) . . ? N3 Pd N1 160.59(19) . . ? N2 Pd Cl 179.10(19) . . ? N3 Pd Cl 98.21(18) . . ? N1 Pd Cl 101.20(16) . . ? C7 N2 C3 123.6(5) . . ? C7 N2 Pd 117.0(4) . . ? C3 N2 Pd 119.4(4) . . ? C2 N1 C17 118.7(6) . . ? C2 N1 Pd 114.2(4) . . ? C17 N1 Pd 127.1(4) . . ? C8 N3 C9 119.0(6) . . ? C8 N3 Pd 114.0(5) . . ? C9 N3 Pd 126.9(5) . . ? N1 C2 C1 126.0(6) . . ? N1 C2 C3 114.9(6) . . ? C1 C2 C3 119.2(6) . . ? N2 C3 C4 119.9(6) . . ? N2 C3 C2 112.3(5) . . ? C4 C3 C2 127.8(6) . . ? O C8 N3 126.9(7) . . ? O C8 C7 119.8(6) . . ? N3 C8 C7 113.3(6) . . ? N2 C7 C6 119.3(6) . . ? N2 C7 C8 114.1(6) . . ? C6 C7 C8 126.5(6) . . ? C17 C22 C21 115.7(8) . . ? C17 C22 C23 123.8(7) . . ? C21 C22 C23 120.5(8) . . ? C6 C5 C4 121.2(6) . . ? C3 C4 C5 117.9(6) . . ? N3 C9 C10 114.3(8) . . ? C22 C17 C18 124.0(6) . . ? C22 C17 N1 118.5(7) . . ? C18 C17 N1 117.5(6) . . ? C5 C6 C7 118.2(6) . . ? C20 C19 C18 121.6(9) . . ? C21 C20 C19 119.9(8) . . ? C17 C18 C19 116.1(8) . . ? C17 C18 C25 121.6(7) . . ? C19 C18 C25 122.3(8) . . ? C20 C21 C22 122.7(8) . . ? C26 C25 C18 120.2(11) . . ? C24 C23 C22 113.1(8) . . ? C12 C11 C10 121.1(18) . . ? C11 C10 C9 118.9(11) . . ? C13 C14 C15 110.0(17) . . ? C11 C12 C13 125(2) . . ? C14 C13 C12 118(2) . . ? C16 C15 C14 108.5(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.490 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.116 #==END data_C10 _database_code_depnum_ccdc_archive 'CCDC 828938' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H33 Cl2 N3 Ni O' _chemical_formula_weight 509.14 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.797(2) _cell_length_b 16.923(3) _cell_length_c 13.860(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.19(3) _cell_angle_gamma 90.00 _cell_volume 2530.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18044 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.998 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR by T. Higashi, March, 2001' _exptl_absorpt_correction_T_min 0.6567 _exptl_absorpt_correction_T_max 0.8178 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid IP' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18044 _diffrn_reflns_av_R_equivalents 0.0916 _diffrn_reflns_av_sigmaI/netI 0.1268 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5697 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'rapid auto(Rigaku 2001)' _computing_cell_refinement 'rapid auto(Rigaku 2001)' _computing_data_reduction 'rapid auto(Rigaku 2001)' _computing_structure_solution 'Shelxs-97(Sheldrick, 1997)' _computing_structure_refinement 'Shelxl-97(Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0794P)^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 5697 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 Ni Ni 0.82832(6) 0.17883(3) 0.08745(4) 0.0393(2) Uani 1 1 d . . . C8 C 0.8640(5) 0.3644(2) 0.1234(3) 0.0405(11) Uani 1 1 d . . . Cl2 Cl 0.97536(13) 0.12730(7) 0.19333(9) 0.0517(3) Uani 1 1 d . . . C17 C 1.0378(6) 0.3338(3) 0.2472(4) 0.0635(16) Uani 1 1 d . . . H17A H 1.0466 0.2883 0.2044 0.076 Uiso 1 1 calc R . . Cl1 Cl 0.65317(14) 0.20511(8) 0.15548(11) 0.0636(4) Uani 1 1 d . . . N2 N 0.9275(3) 0.1681(2) -0.0287(2) 0.0351(8) Uani 1 1 d . . . O1 O 0.7741(3) 0.06630(19) 0.0321(2) 0.0519(9) Uani 1 1 d . . . N1 N 0.8993(4) 0.2956(2) 0.0685(3) 0.0367(9) Uani 1 1 d . . . C7 C 0.9301(4) 0.0999(3) -0.0755(3) 0.0377(10) Uani 1 1 d . . . N3 N 0.8368(4) -0.0297(2) -0.0660(3) 0.0476(11) Uani 1 1 d . . . C2 C 0.9762(5) 0.3019(2) 0.0010(3) 0.0395(11) Uani 1 1 d . . . C3 C 0.9946(5) 0.2296(3) -0.0558(3) 0.0394(11) Uani 1 1 d . . . C6 C 1.0063(5) 0.0887(3) -0.1516(3) 0.0470(13) Uani 1 1 d . . . H6A H 1.0096 0.0401 -0.1828 0.056 Uiso 1 1 calc R . . C20 C 0.8410(5) 0.0432(3) -0.0329(3) 0.0423(11) Uani 1 1 d . . . C9 C 0.9296(5) 0.3823(3) 0.2087(4) 0.0461(12) Uani 1 1 d . . . C4 C 1.0726(5) 0.2221(3) -0.1321(3) 0.0446(12) Uani 1 1 d . . . H4A H 1.1212 0.2645 -0.1504 0.053 Uiso 1 1 calc R . . C13 C 0.7617(5) 0.4077(3) 0.0906(4) 0.0477(12) Uani 1 1 d . . . C12 C 0.7308(5) 0.4741(3) 0.1444(4) 0.0535(14) Uani 1 1 d . . . H12A H 0.6639 0.5049 0.1232 0.064 Uiso 1 1 calc R . . C5 C 1.0778(5) 0.1514(3) -0.1804(3) 0.0517(14) Uani 1 1 d . . . H5A H 1.1292 0.1459 -0.2323 0.062 Uiso 1 1 calc R . . C11 C 0.7948(6) 0.4951(3) 0.2263(4) 0.0623(16) Uani 1 1 d . . . H11A H 0.7730 0.5402 0.2601 0.075 Uiso 1 1 calc R . . C21 C 0.7503(5) -0.0881(3) -0.0310(4) 0.0530(13) Uani 1 1 d . . . H21A H 0.7366 -0.0779 0.0366 0.064 Uiso 1 1 calc R . . H21B H 0.7873 -0.1402 -0.0355 0.064 Uiso 1 1 calc R . . C1 C 1.0428(6) 0.3757(3) -0.0254(4) 0.0637(16) Uani 1 1 d . . . H1A H 1.0215 0.4175 0.0178 0.096 Uiso 1 1 calc R . . H1B H 1.0192 0.3905 -0.0904 0.096 Uiso 1 1 calc R . . H1C H 1.1306 0.3667 -0.0206 0.096 Uiso 1 1 calc R . . C14 C 0.6875(6) 0.3871(3) -0.0003(4) 0.0629(16) Uani 1 1 d . . . H14A H 0.7148 0.3351 -0.0221 0.075 Uiso 1 1 calc R . . C10 C 0.8927(6) 0.4489(3) 0.2590(4) 0.0572(14) Uani 1 1 d . . . H10A H 0.9353 0.4625 0.3162 0.069 Uiso 1 1 calc R . . C22 C 0.6299(6) -0.0881(4) -0.0848(4) 0.0622(15) Uani 1 1 d . . . H22A H 0.5930 -0.0361 -0.0799 0.075 Uiso 1 1 calc R . . H22B H 0.5753 -0.1255 -0.0547 0.075 Uiso 1 1 calc R . . C16 C 0.5503(6) 0.3821(4) 0.0181(5) 0.084(2) Uani 1 1 d . . . H16A H 0.5369 0.3439 0.0678 0.126 Uiso 1 1 calc R . . H16B H 0.5059 0.3664 -0.0401 0.126 Uiso 1 1 calc R . . H16C H 0.5210 0.4329 0.0383 0.126 Uiso 1 1 calc R . . C24 C 0.6784(7) -0.1896(4) -0.2113(6) 0.090(2) Uani 1 1 d . . . H24A H 0.6811 -0.1960 -0.2800 0.136 Uiso 1 1 calc R . . H24B H 0.6211 -0.2269 -0.1860 0.136 Uiso 1 1 calc R . . H24C H 0.7594 -0.1986 -0.1825 0.136 Uiso 1 1 calc R . . C23 C 0.6380(6) -0.1089(4) -0.1891(4) 0.0717(17) Uani 1 1 d . . . H23A H 0.5570 -0.1007 -0.2202 0.086 Uiso 1 1 calc R . . H23B H 0.6948 -0.0722 -0.2181 0.086 Uiso 1 1 calc R . . C15 C 0.7087(7) 0.4460(5) -0.0803(4) 0.091(2) Uani 1 1 d . . . H15A H 0.7954 0.4481 -0.0929 0.136 Uiso 1 1 calc R . . H15B H 0.6810 0.4973 -0.0610 0.136 Uiso 1 1 calc R . . H15C H 0.6630 0.4299 -0.1378 0.136 Uiso 1 1 calc R . . C18 C 1.1589(7) 0.3809(5) 0.2472(7) 0.114(3) Uani 1 1 d . . . H18A H 1.1730 0.3993 0.1830 0.114 Uiso 1 1 calc R . . H18B H 1.2264 0.3477 0.2688 0.114 Uiso 1 1 calc R . . H18C H 1.1532 0.4254 0.2899 0.114 Uiso 1 1 calc R . . C19 C 1.0183(10) 0.3033(5) 0.3468(5) 0.130(4) Uani 1 1 d . . . H19A H 1.0187 0.3466 0.3915 0.130 Uiso 1 1 calc R . . H19B H 1.0837 0.2671 0.3649 0.130 Uiso 1 1 calc R . . H19C H 0.9400 0.2764 0.3480 0.130 Uiso 1 1 calc R . . H3A H 0.874(4) -0.046(3) -0.109(3) 0.040(15) 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 Ni 0.0481(4) 0.0284(3) 0.0422(3) -0.0041(3) 0.0126(3) -0.0004(3) C8 0.055(3) 0.024(2) 0.044(3) -0.001(2) 0.009(2) 0.000(2) Cl2 0.0620(9) 0.0387(6) 0.0544(7) -0.0020(6) 0.0027(6) 0.0061(6) C17 0.080(4) 0.048(3) 0.061(4) -0.013(3) -0.011(3) 0.000(3) Cl1 0.0595(9) 0.0512(7) 0.0825(10) -0.0123(7) 0.0324(7) -0.0021(7) N2 0.043(2) 0.0290(19) 0.0332(19) 0.0011(16) 0.0029(16) 0.0009(17) O1 0.063(2) 0.0360(17) 0.058(2) -0.0126(17) 0.0187(18) -0.0095(17) N1 0.042(2) 0.0277(18) 0.041(2) -0.0006(16) 0.0048(17) 0.0032(16) C7 0.047(3) 0.029(2) 0.037(2) 0.001(2) -0.002(2) 0.003(2) N3 0.060(3) 0.031(2) 0.052(3) -0.011(2) 0.010(2) -0.001(2) C2 0.048(3) 0.026(2) 0.045(3) 0.000(2) 0.008(2) 0.002(2) C3 0.050(3) 0.033(2) 0.036(2) 0.003(2) 0.005(2) 0.004(2) C6 0.067(4) 0.037(3) 0.037(2) -0.008(2) 0.008(2) 0.013(3) C20 0.049(3) 0.035(2) 0.042(3) -0.002(2) 0.002(2) 0.005(2) C9 0.057(3) 0.028(2) 0.053(3) -0.006(2) 0.010(2) -0.007(2) C4 0.054(3) 0.036(2) 0.045(3) 0.003(2) 0.016(2) 0.000(2) C13 0.060(3) 0.032(2) 0.052(3) -0.001(2) 0.015(2) 0.001(2) C12 0.062(4) 0.030(2) 0.069(4) 0.002(3) 0.020(3) 0.008(2) C5 0.070(4) 0.046(3) 0.041(3) 0.002(2) 0.027(3) 0.007(3) C11 0.087(5) 0.036(3) 0.066(4) -0.019(3) 0.024(3) 0.000(3) C21 0.067(4) 0.033(3) 0.059(3) 0.002(2) 0.002(3) -0.006(2) C1 0.083(5) 0.037(3) 0.073(4) 0.000(3) 0.022(3) -0.013(3) C14 0.069(4) 0.048(3) 0.071(4) -0.017(3) -0.004(3) 0.023(3) C10 0.072(4) 0.044(3) 0.056(3) -0.017(3) 0.007(3) -0.008(3) C22 0.068(4) 0.052(3) 0.068(4) 0.004(3) 0.013(3) 0.001(3) C16 0.080(5) 0.069(4) 0.102(5) -0.006(4) -0.009(4) 0.012(4) C24 0.069(5) 0.091(5) 0.110(6) -0.038(5) -0.001(4) -0.008(4) C23 0.072(4) 0.073(4) 0.070(4) -0.011(4) 0.002(3) -0.015(4) C15 0.107(6) 0.107(6) 0.059(4) 0.008(4) 0.005(4) 0.024(5) C18 0.093(6) 0.081(5) 0.165(8) -0.021(6) -0.045(6) 0.004(5) C19 0.216(11) 0.101(6) 0.072(5) 0.011(5) -0.006(6) 0.057(7) _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 Ni N2 1.975(4) . ? Ni O1 2.127(3) . ? Ni N1 2.139(4) . ? Ni Cl1 2.1907(16) . ? Ni Cl2 2.2927(16) . ? C8 C13 1.388(7) . ? C8 C9 1.388(7) . ? C8 N1 1.450(5) . ? C17 C19 1.497(9) . ? C17 C9 1.508(8) . ? C17 C18 1.531(9) . ? C17 H17A 0.9800 . ? N2 C7 1.326(5) . ? N2 C3 1.330(6) . ? O1 C20 1.239(5) . ? N1 C2 1.280(6) . ? C7 C6 1.375(6) . ? C7 C20 1.497(7) . ? N3 C20 1.316(6) . ? N3 C21 1.456(7) . ? N3 H3A 0.78(5) . ? C2 C3 1.472(6) . ? C2 C1 1.494(6) . ? C3 C4 1.382(6) . ? C6 C5 1.381(7) . ? C6 H6A 0.9300 . ? C9 C10 1.391(7) . ? C4 C5 1.372(7) . ? C4 H4A 0.9300 . ? C13 C12 1.395(7) . ? C13 C14 1.508(7) . ? C12 C11 1.354(7) . ? C12 H12A 0.9300 . ? C5 H5A 0.9300 . ? C11 C10 1.378(8) . ? C11 H11A 0.9300 . ? C21 C22 1.474(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C14 C15 1.514(9) . ? C14 C16 1.515(8) . ? C14 H14A 0.9800 . ? C10 H10A 0.9300 . ? C22 C23 1.494(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C24 C23 1.468(9) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni O1 76.95(14) . . ? N2 Ni N1 77.12(14) . . ? O1 Ni N1 151.39(14) . . ? N2 Ni Cl1 150.82(12) . . ? O1 Ni Cl1 96.13(10) . . ? N1 Ni Cl1 100.62(11) . . ? N2 Ni Cl2 95.91(11) . . ? O1 Ni Cl2 93.70(11) . . ? N1 Ni Cl2 100.79(11) . . ? Cl1 Ni Cl2 112.94(6) . . ? C13 C8 C9 122.5(4) . . ? C13 C8 N1 118.4(4) . . ? C9 C8 N1 119.1(4) . . ? C19 C17 C9 112.4(6) . . ? C19 C17 C18 109.2(7) . . ? C9 C17 C18 111.5(5) . . ? C19 C17 H17A 107.9 . . ? C9 C17 H17A 107.9 . . ? C18 C17 H17A 107.9 . . ? C7 N2 C3 121.4(4) . . ? C7 N2 Ni 120.1(3) . . ? C3 N2 Ni 118.5(3) . . ? C20 O1 Ni 112.7(3) . . ? C2 N1 C8 120.5(4) . . ? C2 N1 Ni 114.3(3) . . ? C8 N1 Ni 125.1(3) . . ? N2 C7 C6 121.3(4) . . ? N2 C7 C20 109.8(4) . . ? C6 C7 C20 128.9(4) . . ? C20 N3 C21 122.3(5) . . ? C20 N3 H3A 125(4) . . ? C21 N3 H3A 112(4) . . ? N1 C2 C3 115.2(4) . . ? N1 C2 C1 125.5(4) . . ? C3 C2 C1 119.2(4) . . ? N2 C3 C4 119.9(4) . . ? N2 C3 C2 114.4(4) . . ? C4 C3 C2 125.7(4) . . ? C7 C6 C5 118.3(4) . . ? C7 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? O1 C20 N3 122.5(5) . . ? O1 C20 C7 119.1(4) . . ? N3 C20 C7 118.5(4) . . ? C8 C9 C10 117.2(5) . . ? C8 C9 C17 123.1(4) . . ? C10 C9 C17 119.7(5) . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C8 C13 C12 117.0(5) . . ? C8 C13 C14 122.8(4) . . ? C12 C13 C14 120.2(5) . . ? C11 C12 C13 122.4(5) . . ? C11 C12 H12A 118.8 . . ? C13 C12 H12A 118.8 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C12 C11 C10 119.1(5) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? N3 C21 C22 113.3(4) . . ? N3 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N3 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C13 C14 C15 111.7(5) . . ? C13 C14 C16 111.3(5) . . ? C15 C14 C16 109.6(5) . . ? C13 C14 H14A 108.0 . . ? C15 C14 H14A 108.0 . . ? C16 C14 H14A 108.0 . . ? C11 C10 C9 121.7(5) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C21 C22 C23 114.0(5) . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C24 C23 C22 116.8(6) . . ? C24 C23 H23A 108.1 . . ? C22 C23 H23A 108.1 . . ? C24 C23 H23B 108.1 . . ? C22 C23 H23B 108.1 . . ? H23A C23 H23B 107.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O1 Ni N2 C7 -8.9(3) . . . . ? N1 Ni N2 C7 -176.7(4) . . . . ? Cl1 Ni N2 C7 -87.9(4) . . . . ? Cl2 Ni N2 C7 83.5(3) . . . . ? O1 Ni N2 C3 173.8(4) . . . . ? N1 Ni N2 C3 6.0(3) . . . . ? Cl1 Ni N2 C3 94.7(4) . . . . ? Cl2 Ni N2 C3 -93.8(3) . . . . ? N2 Ni O1 C20 10.7(3) . . . . ? N1 Ni O1 C20 36.2(5) . . . . ? Cl1 Ni O1 C20 161.9(3) . . . . ? Cl2 Ni O1 C20 -84.5(3) . . . . ? C13 C8 N1 C2 90.5(6) . . . . ? C9 C8 N1 C2 -92.5(6) . . . . ? C13 C8 N1 Ni -87.7(5) . . . . ? C9 C8 N1 Ni 89.3(5) . . . . ? N2 Ni N1 C2 -5.6(3) . . . . ? O1 Ni N1 C2 -31.0(5) . . . . ? Cl1 Ni N1 C2 -155.9(3) . . . . ? Cl2 Ni N1 C2 88.1(3) . . . . ? N2 Ni N1 C8 172.6(4) . . . . ? O1 Ni N1 C8 147.2(4) . . . . ? Cl1 Ni N1 C8 22.4(4) . . . . ? Cl2 Ni N1 C8 -93.7(4) . . . . ? C3 N2 C7 C6 2.8(7) . . . . ? Ni N2 C7 C6 -174.5(3) . . . . ? C3 N2 C7 C20 -176.9(4) . . . . ? Ni N2 C7 C20 5.8(5) . . . . ? C8 N1 C2 C3 -173.9(4) . . . . ? Ni N1 C2 C3 4.4(5) . . . . ? C8 N1 C2 C1 3.9(8) . . . . ? Ni N1 C2 C1 -177.8(4) . . . . ? C7 N2 C3 C4 -2.5(7) . . . . ? Ni N2 C3 C4 174.8(3) . . . . ? C7 N2 C3 C2 177.1(4) . . . . ? Ni N2 C3 C2 -5.6(5) . . . . ? N1 C2 C3 N2 0.4(6) . . . . ? C1 C2 C3 N2 -177.5(5) . . . . ? N1 C2 C3 C4 180.0(5) . . . . ? C1 C2 C3 C4 2.0(7) . . . . ? N2 C7 C6 C5 -2.0(7) . . . . ? C20 C7 C6 C5 177.6(5) . . . . ? Ni O1 C20 N3 168.6(4) . . . . ? Ni O1 C20 C7 -11.3(6) . . . . ? C21 N3 C20 O1 2.1(8) . . . . ? C21 N3 C20 C7 -178.0(4) . . . . ? N2 C7 C20 O1 4.4(6) . . . . ? C6 C7 C20 O1 -175.3(5) . . . . ? N2 C7 C20 N3 -175.5(4) . . . . ? C6 C7 C20 N3 4.8(8) . . . . ? C13 C8 C9 C10 -3.2(7) . . . . ? N1 C8 C9 C10 180.0(4) . . . . ? C13 C8 C9 C17 177.4(5) . . . . ? N1 C8 C9 C17 0.6(7) . . . . ? C19 C17 C9 C8 -122.5(6) . . . . ? C18 C17 C9 C8 114.4(6) . . . . ? C19 C17 C9 C10 58.1(7) . . . . ? C18 C17 C9 C10 -64.9(7) . . . . ? N2 C3 C4 C5 1.5(7) . . . . ? C2 C3 C4 C5 -178.1(5) . . . . ? C9 C8 C13 C12 3.8(7) . . . . ? N1 C8 C13 C12 -179.4(4) . . . . ? C9 C8 C13 C14 -178.1(5) . . . . ? N1 C8 C13 C14 -1.2(7) . . . . ? C8 C13 C12 C11 -1.6(7) . . . . ? C14 C13 C12 C11 -179.8(5) . . . . ? C3 C4 C5 C6 -0.8(8) . . . . ? C7 C6 C5 C4 1.1(8) . . . . ? C13 C12 C11 C10 -1.1(8) . . . . ? C20 N3 C21 C22 88.7(6) . . . . ? C8 C13 C14 C15 -108.4(6) . . . . ? C12 C13 C14 C15 69.7(7) . . . . ? C8 C13 C14 C16 128.7(5) . . . . ? C12 C13 C14 C16 -53.2(7) . . . . ? C12 C11 C10 C9 1.8(8) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C17 C9 C10 C11 179.7(5) . . . . ? N3 C21 C22 C23 62.6(7) . . . . ? C21 C22 C23 C24 65.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.601 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.122 #==END data_C12 _database_code_depnum_ccdc_archive 'CCDC 828939' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31.74 H50.34 Cl2 N3 Ni O1.93' _chemical_formula_weight 634.48 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.574(6) _cell_length_b 17.728(7) _cell_length_c 15.650(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.81(2) _cell_angle_gamma 90.00 _cell_volume 3543(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9104 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1357 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7953 _exptl_absorpt_correction_T_max 0.8563 _exptl_absorpt_process_details 'ABSCOR by T. Higashi, March, 2001' _exptl_special_details ; SPACE GROUP DETERMINATION Lattice exceptions: P A B C I F Obv Rev All N (total) = 0 17111 17139 17108 17162 25679 22844 22836 34239 N (int>3sigma) = 0 4885 4812 4827 4745 7262 6488 6506 9731 Mean intensity = 0.0 52.3 50.9 52.8 48.9 52.0 53.4 54.0 54.4 Mean int/sigma = 0.0 4.3 4.3 4.4 4.2 4.3 4.4 4.4 4.4 Crystal system M and Lattice type P selected Mean |E*E-1| = 0.922 [expected .968 centrosym and .736 non-centrosym] Chiral flag NOT set Systematic absence exceptions: -21- -a- -c- -n- N 27 772 758 788 N I>3s 0 153 153 0 2.6 94.0 95.6 3.6 0.4 4.0 4.0 0.3 Option Space Group No. Type Axes CSD R(int) N(eq) Syst. Abs. CFOM [A] P2(1)/n # 14 centro 1 19410 0.151 25135 0.4 / 4.0 2.95 Option [A] chosen ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid IP' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 27403 _diffrn_reflns_av_R_equivalents 0.1385 _diffrn_reflns_av_sigmaI/netI 0.0908 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6229 _reflns_number_gt 3110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'rapid auto(Rigaku 2001)' _computing_cell_refinement 'rapid auto(Rigaku 2001)' _computing_data_reduction 'rapid auto(Rigaku 2001)' _computing_structure_solution 'Shelxs-97(Sheldrick, 1997)' _computing_structure_refinement 'Shelxl-97(Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; we try to modle disorder for the alkyl chain and the ethyl ether, but result is not good. now, we just refin the bond disances and angles of the alkyl chain and the ethyl ether. 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^)+(0.1270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6229 _refine_ls_number_parameters 362 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.2193 _refine_ls_wR_factor_gt 0.1865 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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 Ni Ni 2.15391(5) 1.11946(3) 2.19882(5) 0.0600(3) Uani 1 1 d . . . Cl2 Cl 2.21529(12) 1.12662(8) 2.07974(10) 0.0723(4) Uani 1 1 d . . . Cl1 Cl 2.13259(13) 1.23222(8) 2.25108(12) 0.0819(5) Uani 1 1 d . . . O1 O 1.9912(3) 1.1055(2) 2.1162(3) 0.0732(12) Uani 1 1 d . . . C8 C 2.3775(4) 1.1251(3) 2.3635(4) 0.0572(14) Uani 1 1 d . . . N1 N 2.2964(3) 1.0797(2) 2.3006(3) 0.0559(11) Uani 1 1 d . . . N2 N 2.1344(3) 1.0085(2) 2.1929(3) 0.0550(11) Uani 1 1 d . . . N3 N 1.8707(4) 1.0187(3) 2.0450(3) 0.0701(13) Uani 1 1 d . . . H3A H 1.8588 0.9716 2.0329 0.084 Uiso 1 1 calc R . . C17 C 2.4816(5) 1.1238(4) 2.2548(5) 0.0804(19) Uani 1 1 d . . . H17A H 2.4234 1.0907 2.2215 0.096 Uiso 1 1 calc R . . C10 C 2.5436(5) 1.1872(3) 2.4055(6) 0.083(2) Uani 1 1 d . . . H10A H 2.6042 1.1995 2.3935 0.099 Uiso 1 1 calc R . . C9 C 2.4657(4) 1.1449(3) 2.3427(4) 0.0653(16) Uani 1 1 d . . . C4 C 2.2104(5) 0.8878(3) 2.2293(4) 0.0663(15) Uani 1 1 d . . . H4A H 2.2666 0.8577 2.2624 0.080 Uiso 1 1 calc R . . C13 C 2.3619(5) 1.1486(3) 2.4422(4) 0.0687(16) Uani 1 1 d . . . C2 C 2.3061(4) 1.0073(3) 2.3022(4) 0.0593(14) Uani 1 1 d . . . C20 C 1.9653(4) 1.0391(3) 2.0968(4) 0.0619(14) Uani 1 1 d . . . C7 C 2.0468(4) 0.9783(3) 2.1370(4) 0.0578(14) Uani 1 1 d . . . C11 C 2.5313(6) 1.2107(4) 2.4850(6) 0.092(2) Uani 1 1 d . . . H11A H 2.5833 1.2392 2.5266 0.111 Uiso 1 1 calc R . . C6 C 2.0353(5) 0.9014(3) 2.1226(4) 0.0704(16) Uani 1 1 d . . . H6A H 1.9733 0.8810 2.0835 0.084 Uiso 1 1 calc R . . C14 C 2.2669(6) 1.1275(4) 2.4647(5) 0.087(2) Uani 1 1 d . . . H14A H 2.2156 1.1072 2.4092 0.104 Uiso 1 1 calc R . . C5 C 2.1210(5) 0.8553(3) 2.1694(5) 0.0769(18) Uani 1 1 d . . . H5A H 2.1176 0.8034 2.1601 0.092 Uiso 1 1 calc R . . C3 C 2.2157(4) 0.9644(3) 2.2395(4) 0.0571(14) Uani 1 1 d . . . C21 C 1.7847(5) 1.0720(4) 2.0069(5) 0.0823(19) Uani 1 1 d DU . . H21A H 1.7650 1.0727 1.9412 0.099 Uiso 1 1 d R . . H21B H 1.8074 1.1224 2.0291 0.099 Uiso 1 1 d R . . C1 C 2.3989(5) 0.9632(3) 2.3626(5) 0.082(2) Uani 1 1 d . . . H1A H 2.4510 0.9976 2.3988 0.123 Uiso 1 1 calc R . . H1B H 2.4280 0.9335 2.3257 0.123 Uiso 1 1 calc R . . H1C H 2.3767 0.9307 2.4016 0.123 Uiso 1 1 calc R . . C16 C 2.2151(8) 1.1960(5) 2.4943(6) 0.126(3) Uani 1 1 d . . . H16A H 2.1988 1.2340 2.4479 0.189 Uiso 1 1 calc R . . H16B H 2.2624 1.2164 2.5499 0.189 Uiso 1 1 calc R . . H16C H 2.1518 1.1800 2.5035 0.189 Uiso 1 1 calc R . . C12 C 2.4423(6) 1.1921(4) 2.5026(5) 0.084(2) Uani 1 1 d . . . H12A H 2.4346 1.2088 2.5563 0.101 Uiso 1 1 calc R . . C19 C 2.4758(7) 1.1937(5) 2.1954(6) 0.112(3) Uani 1 1 d . . . H19A H 2.4113 1.2200 2.1869 0.167 Uiso 1 1 calc R . . H19B H 2.4786 1.1784 2.1374 0.167 Uiso 1 1 calc R . . H19C H 2.5337 1.2264 2.2247 0.167 Uiso 1 1 calc R . . C18 C 2.5845(6) 1.0795(5) 2.2679(6) 0.112(3) Uani 1 1 d . . . H18A H 2.5862 1.0353 2.3037 0.168 Uiso 1 1 calc R . . H18B H 2.6435 1.1110 2.2984 0.168 Uiso 1 1 calc R . . H18C H 2.5873 1.0650 2.2097 0.168 Uiso 1 1 calc R . . C15 C 2.2921(7) 1.0646(5) 2.5361(6) 0.116(3) Uani 1 1 d . . . H15A H 2.3215 1.0223 2.5149 0.173 Uiso 1 1 calc R . . H15B H 2.2290 1.0493 2.5460 0.173 Uiso 1 1 calc R . . H15C H 2.3415 1.0828 2.5920 0.173 Uiso 1 1 calc R . . C22 C 1.6935(6) 1.0483(5) 2.0353(7) 0.126(3) Uani 1 1 d DU . . H22A H 1.7114 1.0531 2.1006 0.151 Uiso 1 1 d R . . H22B H 1.6764 0.9958 2.0196 0.151 Uiso 1 1 d R . . C23 C 1.6008(7) 1.1025(6) 2.0050(8) 0.160(5) Uani 1 1 d DU . . H23A H 1.5635 1.0964 2.0476 0.192 Uiso 1 1 d R . . H23B H 1.6321 1.1522 2.0185 0.192 Uiso 1 1 d R . . C24 C 1.5462(10) 1.1058(7) 1.9044(8) 0.181(6) Uani 1 1 d DU . . H24A H 1.4934 1.0671 1.8963 0.218 Uiso 1 1 d R . . H24B H 1.5705 1.1029 1.8529 0.218 Uiso 1 1 d R . . C25 C 1.4444(10) 1.1569(11) 1.8911(10) 0.247(8) Uani 1 1 d DU . . H25A H 1.4200 1.1681 1.9413 0.297 Uiso 1 1 d R . . H25B H 1.4774 1.1996 1.8729 0.297 Uiso 1 1 d R . . C27 C 1.2722(14) 1.2100(16) 1.7842(19) 0.47(2) Uani 1 1 d DU . . H27A H 1.2230 1.1810 1.7358 0.559 Uiso 1 1 d R . . H27B H 1.2443 1.2151 1.8333 0.559 Uiso 1 1 d R . . C26 C 1.3627(13) 1.1537(12) 1.7977(11) 0.536(12) Uani 1 1 d DU . . H26A H 1.3559 1.1036 1.8199 0.643 Uiso 1 1 d R . . H26B H 1.3909 1.1491 1.7487 0.643 Uiso 1 1 d R . . O2 O 2.0438(19) 0.9688(14) 2.3853(14) 0.305(10) Uani 0.931(15) 1 d PDU A 1 C30 C 2.0507(17) 0.8903(14) 2.4024(16) 0.248(11) Uani 0.931(15) 1 d PDU A 1 H30A H 2.0287 0.8641 2.3446 0.298 Uiso 0.931(15) 1 calc PR A 1 H30B H 2.0015 0.8774 2.4329 0.298 Uiso 0.931(15) 1 calc PR A 1 C31 C 1.935(2) 0.9792(16) 2.334(2) 0.350(19) Uani 0.931(15) 1 d PDU A 1 H31A H 1.8895 0.9610 2.3655 0.420 Uiso 0.931(15) 1 calc PR A 1 H31B H 1.9154 0.9562 2.2740 0.420 Uiso 0.931(15) 1 calc PR A 1 C32 C 1.937(2) 1.0653(16) 2.3295(18) 0.304(14) Uani 0.931(15) 1 d PDU A 1 H32A H 1.8699 1.0836 2.2924 0.456 Uiso 0.931(15) 1 calc PR A 1 H32B H 1.9892 1.0808 2.3038 0.456 Uiso 0.931(15) 1 calc PR A 1 H32C H 1.9548 1.0856 2.3897 0.456 Uiso 0.931(15) 1 calc PR A 1 C29 C 2.1589(16) 0.8610(11) 2.4598(13) 0.236(9) Uani 0.931(15) 1 d PDU A 1 H29A H 2.1563 0.8072 2.4655 0.354 Uiso 0.931(15) 1 calc PR A 1 H29B H 2.1796 0.8837 2.5190 0.354 Uiso 0.931(15) 1 calc PR A 1 H29C H 2.2088 0.8739 2.4309 0.354 Uiso 0.931(15) 1 calc PR A 1 C28 C 1.303(4) 1.2905(17) 1.763(5) 0.75(5) Uani 1 1 d DU . . H28A H 1.2381 1.3181 1.7449 1.126 Uiso 1 1 d R . . H28B H 1.3261 1.2847 1.7122 1.126 Uiso 1 1 d R . . H28C H 1.3546 1.3175 1.8106 1.126 Uiso 1 1 d 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 Ni 0.0596(4) 0.0364(4) 0.0642(5) -0.0002(3) -0.0048(3) 0.0002(3) Cl2 0.0732(9) 0.0605(8) 0.0663(10) 0.0014(7) 0.0016(7) -0.0062(7) Cl1 0.0896(11) 0.0411(7) 0.0966(13) -0.0091(7) 0.0075(9) 0.0021(7) O1 0.061(2) 0.050(2) 0.085(3) -0.001(2) -0.006(2) 0.0028(17) C8 0.055(3) 0.044(3) 0.052(3) -0.002(3) -0.009(3) 0.002(2) N1 0.061(3) 0.033(2) 0.058(3) -0.0008(19) 0.000(2) -0.0014(18) N2 0.051(3) 0.039(2) 0.060(3) 0.000(2) 0.000(2) -0.0039(18) N3 0.058(3) 0.061(3) 0.074(3) -0.005(3) -0.002(3) -0.004(2) C17 0.065(4) 0.070(4) 0.095(5) 0.003(4) 0.011(4) -0.004(3) C10 0.071(4) 0.051(3) 0.097(6) 0.007(4) -0.009(4) -0.010(3) C9 0.059(3) 0.048(3) 0.068(4) 0.005(3) -0.006(3) 0.001(2) C4 0.069(4) 0.042(3) 0.074(4) 0.000(3) 0.004(3) 0.006(2) C13 0.072(4) 0.051(3) 0.062(4) 0.001(3) -0.004(3) 0.004(3) C2 0.056(3) 0.051(3) 0.055(3) 0.004(3) -0.001(3) 0.000(2) C20 0.058(3) 0.055(3) 0.061(4) -0.002(3) 0.004(3) -0.004(3) C7 0.062(3) 0.045(3) 0.055(3) -0.001(2) 0.006(3) -0.005(2) C11 0.087(5) 0.055(4) 0.089(6) 0.000(4) -0.029(4) -0.012(3) C6 0.069(4) 0.052(3) 0.072(4) -0.006(3) 0.001(3) -0.011(3) C14 0.090(5) 0.088(5) 0.069(4) -0.007(4) 0.009(4) 0.008(4) C5 0.084(4) 0.041(3) 0.085(5) -0.002(3) 0.002(4) -0.011(3) C3 0.062(3) 0.041(3) 0.056(3) 0.003(2) 0.005(3) 0.002(2) C21 0.061(4) 0.089(5) 0.082(5) 0.012(4) 0.006(3) 0.004(3) C1 0.078(4) 0.048(3) 0.088(5) 0.008(3) -0.013(3) 0.004(3) C16 0.146(8) 0.133(7) 0.104(6) -0.011(6) 0.048(6) 0.049(6) C12 0.102(5) 0.060(4) 0.062(4) -0.005(3) -0.009(4) 0.007(4) C19 0.128(7) 0.093(5) 0.100(6) 0.027(5) 0.020(5) -0.008(5) C18 0.094(6) 0.112(6) 0.124(7) 0.007(5) 0.030(5) 0.022(5) C15 0.123(7) 0.108(6) 0.111(7) 0.029(5) 0.033(6) 0.003(5) C22 0.089(6) 0.133(7) 0.155(9) 0.017(6) 0.040(6) 0.033(5) C23 0.117(8) 0.144(9) 0.226(14) 0.031(9) 0.068(9) 0.029(7) C24 0.169(11) 0.150(10) 0.175(13) 0.022(9) -0.007(10) 0.031(9) C25 0.150(12) 0.32(2) 0.26(2) -0.067(18) 0.059(13) -0.013(14) C27 0.32(3) 0.51(4) 0.45(4) -0.13(3) -0.02(2) 0.30(3) C26 0.70(3) 0.70(3) 0.26(2) -0.23(2) 0.24(3) -0.517 O2 0.32(2) 0.32(2) 0.271(18) -0.100(17) 0.092(16) -0.139(18) C30 0.23(2) 0.28(3) 0.26(2) -0.08(2) 0.11(2) -0.04(2) C31 0.37(4) 0.41(4) 0.34(3) -0.07(3) 0.21(3) -0.11(3) C32 0.34(3) 0.34(3) 0.26(2) 0.01(2) 0.13(2) -0.04(2) C29 0.217(18) 0.228(19) 0.226(19) -0.062(15) 0.026(16) -0.036(16) C28 0.71(6) 0.76(7) 0.79(7) -0.05(5) 0.26(5) 0.07(5) _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 Ni N2 1.983(4) . ? Ni O1 2.162(4) . ? Ni N1 2.166(4) . ? Ni Cl1 2.2156(17) . ? Ni Cl2 2.288(2) . ? O1 C20 1.236(6) . ? C8 C13 1.383(8) . ? C8 C9 1.388(8) . ? C8 N1 1.447(7) . ? N1 C2 1.290(7) . ? N2 C7 1.327(6) . ? N2 C3 1.348(6) . ? N3 C20 1.315(7) . ? N3 C21 1.463(8) . ? N3 H3A 0.8600 . ? C17 C9 1.510(9) . ? C17 C19 1.535(9) . ? C17 C18 1.554(10) . ? C17 H17A 0.9800 . ? C10 C11 1.375(10) . ? C10 C9 1.393(9) . ? C10 H10A 0.9300 . ? C4 C3 1.367(7) . ? C4 C5 1.383(9) . ? C4 H4A 0.9300 . ? C13 C12 1.407(9) . ? C13 C14 1.495(10) . ? C2 C3 1.494(7) . ? C2 C1 1.511(8) . ? C20 C7 1.521(8) . ? C7 C6 1.381(8) . ? C11 C12 1.368(10) . ? C11 H11A 0.9300 . ? C6 C5 1.408(9) . ? C6 H6A 0.9300 . ? C14 C15 1.533(10) . ? C14 C16 1.551(10) . ? C14 H14A 0.9800 . ? C5 H5A 0.9300 . ? C21 C22 1.511(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 H12A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C22 C23 1.526(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.498(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.606(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.507(10) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C26 1.541(10) . ? C27 C28 1.551(11) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? O2 C30 1.413(10) . ? O2 C31 1.435(10) . ? C30 C29 1.530(10) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.529(10) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni O1 76.41(15) . . ? N2 Ni N1 77.47(16) . . ? O1 Ni N1 151.56(16) . . ? N2 Ni Cl1 151.68(15) . . ? O1 Ni Cl1 95.14(12) . . ? N1 Ni Cl1 102.60(12) . . ? N2 Ni Cl2 95.55(14) . . ? O1 Ni Cl2 95.69(13) . . ? N1 Ni Cl2 97.84(14) . . ? Cl1 Ni Cl2 112.31(7) . . ? C20 O1 Ni 113.9(3) . . ? C13 C8 C9 122.5(5) . . ? C13 C8 N1 117.5(5) . . ? C9 C8 N1 119.9(5) . . ? C2 N1 C8 119.4(4) . . ? C2 N1 Ni 113.4(3) . . ? C8 N1 Ni 127.1(3) . . ? C7 N2 C3 120.6(4) . . ? C7 N2 Ni 120.5(3) . . ? C3 N2 Ni 118.6(3) . . ? C20 N3 C21 123.4(5) . . ? C20 N3 H3A 118.3 . . ? C21 N3 H3A 118.3 . . ? C9 C17 C19 111.0(6) . . ? C9 C17 C18 113.8(6) . . ? C19 C17 C18 110.3(7) . . ? C9 C17 H17A 107.1 . . ? C19 C17 H17A 107.1 . . ? C18 C17 H17A 107.1 . . ? C11 C10 C9 120.4(7) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C8 C9 C10 118.6(6) . . ? C8 C9 C17 123.5(5) . . ? C10 C9 C17 117.9(6) . . ? C3 C4 C5 119.5(5) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C8 C13 C12 116.5(6) . . ? C8 C13 C14 122.6(6) . . ? C12 C13 C14 120.9(6) . . ? N1 C2 C3 116.0(5) . . ? N1 C2 C1 125.7(5) . . ? C3 C2 C1 118.3(5) . . ? O1 C20 N3 123.4(5) . . ? O1 C20 C7 117.8(5) . . ? N3 C20 C7 118.8(5) . . ? N2 C7 C6 122.2(5) . . ? N2 C7 C20 110.5(4) . . ? C6 C7 C20 127.3(5) . . ? C12 C11 C10 119.7(6) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C7 C6 C5 117.4(5) . . ? C7 C6 H6A 121.3 . . ? C5 C6 H6A 121.3 . . ? C13 C14 C15 110.9(6) . . ? C13 C14 C16 112.9(7) . . ? C15 C14 C16 111.3(7) . . ? C13 C14 H14A 107.1 . . ? C15 C14 H14A 107.1 . . ? C16 C14 H14A 107.1 . . ? C4 C5 C6 119.4(5) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? N2 C3 C4 120.9(5) . . ? N2 C3 C2 113.6(4) . . ? C4 C3 C2 125.5(5) . . ? N3 C21 C22 108.7(5) . . ? N3 C21 H21A 109.6 . . ? C22 C21 H21A 110.9 . . ? N3 C21 H21B 109.6 . . ? C22 C21 H21B 110.1 . . ? H21A C21 H21B 108.0 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C12 C13 122.3(7) . . ? C11 C12 H12A 118.9 . . ? C13 C12 H12A 118.9 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C22 C23 113.9(7) . . ? C21 C22 H22A 110.4 . . ? C23 C22 H22A 99.1 . . ? C21 C22 H22B 110.0 . . ? C23 C22 H22B 115.1 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C22 114.5(9) . . ? C24 C23 H23A 122.7 . . ? C22 C23 H23A 106.5 . . ? C24 C23 H23B 102.5 . . ? C22 C23 H23B 104.5 . . ? H23A C23 H23B 104.1 . . ? C23 C24 C25 104.8(9) . . ? C23 C24 H24A 100.9 . . ? C25 C24 H24A 79.4 . . ? C23 C24 H24B 133.3 . . ? C25 C24 H24B 116.2 . . ? H24A C24 H24B 107.4 . . ? C26 C25 C24 115.0(11) . . ? C26 C25 H25A 116.9 . . ? C24 C25 H25A 121.6 . . ? C26 C25 H25B 90.4 . . ? C24 C25 H25B 90.8 . . ? H25A C25 H25B 113.4 . . ? C26 C27 C28 111.5(15) . . ? C26 C27 H27A 93.9 . . ? C28 C27 H27A 119.1 . . ? C26 C27 H27B 117.3 . . ? C28 C27 H27B 106.6 . . ? H27A C27 H27B 108.6 . . ? C25 C26 C27 113.5(13) . . ? C25 C26 H26A 79.3 . . ? C27 C26 H26A 118.3 . . ? C25 C26 H26B 114.4 . . ? C27 C26 H26B 117.1 . . ? H26A C26 H26B 108.5 . . ? C30 O2 C31 102.9(19) . . ? O2 C30 C29 116(2) . . ? O2 C30 H30A 108.4 . . ? C29 C30 H30A 108.4 . . ? O2 C30 H30B 108.4 . . ? C29 C30 H30B 108.4 . . ? H30A C30 H30B 107.4 . . ? O2 C31 C32 97(3) . . ? O2 C31 H31A 112.4 . . ? C32 C31 H31A 112.4 . . ? O2 C31 H31B 112.4 . . ? C32 C31 H31B 112.4 . . ? H31A C31 H31B 109.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C28 H28A 104.5 . . ? C27 C28 H28B 105.3 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 118.3 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 N2 Ni O1 C20 -6.6(4) . . . . ? N1 Ni O1 C20 -30.4(6) . . . . ? Cl1 Ni O1 C20 -159.1(4) . . . . ? Cl2 Ni O1 C20 87.8(4) . . . . ? C13 C8 N1 C2 -97.6(6) . . . . ? C9 C8 N1 C2 83.9(7) . . . . ? C13 C8 N1 Ni 82.6(6) . . . . ? C9 C8 N1 Ni -95.8(5) . . . . ? N2 Ni N1 C2 6.9(4) . . . . ? O1 Ni N1 C2 30.6(6) . . . . ? Cl1 Ni N1 C2 157.9(4) . . . . ? Cl2 Ni N1 C2 -87.0(4) . . . . ? N2 Ni N1 C8 -173.3(5) . . . . ? O1 Ni N1 C8 -149.6(4) . . . . ? Cl1 Ni N1 C8 -22.4(5) . . . . ? Cl2 Ni N1 C8 92.7(4) . . . . ? O1 Ni N2 C7 9.3(4) . . . . ? N1 Ni N2 C7 178.0(5) . . . . ? Cl1 Ni N2 C7 84.6(5) . . . . ? Cl2 Ni N2 C7 -85.2(4) . . . . ? O1 Ni N2 C3 -177.5(5) . . . . ? N1 Ni N2 C3 -8.8(4) . . . . ? Cl1 Ni N2 C3 -102.2(5) . . . . ? Cl2 Ni N2 C3 88.0(4) . . . . ? C13 C8 C9 C10 3.1(8) . . . . ? N1 C8 C9 C10 -178.6(5) . . . . ? C13 C8 C9 C17 -176.2(5) . . . . ? N1 C8 C9 C17 2.2(8) . . . . ? C11 C10 C9 C8 -2.1(8) . . . . ? C11 C10 C9 C17 177.2(6) . . . . ? C19 C17 C9 C8 110.8(7) . . . . ? C18 C17 C9 C8 -124.0(7) . . . . ? C19 C17 C9 C10 -68.4(7) . . . . ? C18 C17 C9 C10 56.8(8) . . . . ? C9 C8 C13 C12 -2.1(8) . . . . ? N1 C8 C13 C12 179.5(5) . . . . ? C9 C8 C13 C14 179.9(5) . . . . ? N1 C8 C13 C14 1.5(8) . . . . ? C8 N1 C2 C3 176.0(5) . . . . ? Ni N1 C2 C3 -4.2(7) . . . . ? C8 N1 C2 C1 -2.7(9) . . . . ? Ni N1 C2 C1 177.1(5) . . . . ? Ni O1 C20 N3 -178.0(5) . . . . ? Ni O1 C20 C7 3.4(7) . . . . ? C21 N3 C20 O1 -2.0(10) . . . . ? C21 N3 C20 C7 176.6(5) . . . . ? C3 N2 C7 C6 -1.2(9) . . . . ? Ni N2 C7 C6 171.9(5) . . . . ? C3 N2 C7 C20 176.9(5) . . . . ? Ni N2 C7 C20 -10.1(6) . . . . ? O1 C20 C7 N2 3.7(8) . . . . ? N3 C20 C7 N2 -174.9(5) . . . . ? O1 C20 C7 C6 -178.3(6) . . . . ? N3 C20 C7 C6 3.0(9) . . . . ? C9 C10 C11 C12 0.3(9) . . . . ? N2 C7 C6 C5 -0.4(9) . . . . ? C20 C7 C6 C5 -178.1(6) . . . . ? C8 C13 C14 C15 102.6(7) . . . . ? C12 C13 C14 C15 -75.2(8) . . . . ? C8 C13 C14 C16 -131.6(7) . . . . ? C12 C13 C14 C16 50.5(8) . . . . ? C3 C4 C5 C6 -2.5(10) . . . . ? C7 C6 C5 C4 2.3(10) . . . . ? C7 N2 C3 C4 1.0(9) . . . . ? Ni N2 C3 C4 -172.2(5) . . . . ? C7 N2 C3 C2 -177.5(5) . . . . ? Ni N2 C3 C2 9.3(6) . . . . ? C5 C4 C3 N2 0.9(10) . . . . ? C5 C4 C3 C2 179.2(6) . . . . ? N1 C2 C3 N2 -2.8(8) . . . . ? C1 C2 C3 N2 176.0(5) . . . . ? N1 C2 C3 C4 178.8(6) . . . . ? C1 C2 C3 C4 -2.4(9) . . . . ? C20 N3 C21 C22 -124.2(7) . . . . ? C10 C11 C12 C13 0.6(10) . . . . ? C8 C13 C12 C11 0.2(9) . . . . ? C14 C13 C12 C11 178.3(6) . . . . ? N3 C21 C22 C23 176.2(8) . . . . ? C21 C22 C23 C24 66.9(14) . . . . ? C22 C23 C24 C25 172.6(11) . . . . ? C23 C24 C25 C26 -165.9(17) . . . . ? C24 C25 C26 C27 -173.5(17) . . . . ? C28 C27 C26 C25 81(4) . . . . ? C31 O2 C30 C29 -178(2) . . . . ? C30 O2 C31 C32 174.2(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.705 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.122 #==END data_C15 _database_code_depnum_ccdc_archive 'CCDC 828940' #TrackingRef '- CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 B F4 N4 O Pd' _chemical_formula_weight 609.79 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 14.325(3) _cell_length_b 11.604(2) _cell_length_c 20.709(7) _cell_angle_alpha 90.00 _cell_angle_beta 125.93(2) _cell_angle_gamma 90.00 _cell_volume 2787.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28773 _cel_cell_measurement_theta_min 1.4334 _cell_measurement_theta_max 30.0300 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7872 _exptl_absorpt_correction_T_max 0.8409 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28773 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.01 _reflns_number_total 8118 _reflns_number_gt 7298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELX97 (Sheldrick, 1997)' _computing_publication_material 'SHELX97 (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^)+(0.0424P)^2^+6.7855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8118 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 0.59226(2) 1.51738(2) -0.336956(15) 0.02396(8) Uani 1 1 d . . . N4 N 0.7623(3) 1.5084(3) -0.2853(2) 0.0321(7) Uani 1 1 d . . . N2 N 0.4312(2) 1.5203(2) -0.38217(18) 0.0246(6) Uani 1 1 d . . . N3 N 0.5376(3) 1.4037(3) -0.42442(18) 0.0280(6) Uani 1 1 d . . . C5 C 0.2048(3) 1.5203(4) -0.4454(3) 0.0393(9) Uani 1 1 d . . . H5A H 0.1267 1.5199 -0.4670 0.047 Uiso 1 1 calc R . . C10 C 0.6652(4) 1.2389(3) -0.3996(3) 0.0368(9) Uani 1 1 d . . . H10A H 0.6060 1.1824 -0.4139 0.044 Uiso 1 1 calc R . . H10B H 0.7080 1.2536 -0.3428 0.044 Uiso 1 1 calc R . . O1 O 0.3684(3) 1.3290(3) -0.53367(17) 0.0447(7) Uani 1 1 d . . . C1 C 0.4666(4) 1.7378(4) -0.2366(3) 0.0397(9) Uani 1 1 d . . . H1A H 0.5371 1.7739 -0.1946 0.060 Uiso 1 1 calc R . . H1B H 0.4338 1.6964 -0.2142 0.060 Uiso 1 1 calc R . . H1C H 0.4133 1.7956 -0.2726 0.060 Uiso 1 1 calc R . . N1 N 0.5913(3) 1.6375(2) -0.26484(17) 0.0252(6) Uani 1 1 d . . . C7 C 0.3617(3) 1.4533(3) -0.4448(2) 0.0286(7) Uani 1 1 d . . . C2 C 0.4908(3) 1.6560(3) -0.2808(2) 0.0278(7) Uani 1 1 d . . . C3 C 0.3952(3) 1.5897(3) -0.3488(2) 0.0279(7) Uani 1 1 d . . . C14 C 0.7389(3) 1.7819(3) -0.2246(2) 0.0294(7) Uani 1 1 d . . . C9 C 0.6086(3) 1.3498(3) -0.4450(2) 0.0312(8) Uani 1 1 d . . . H9A H 0.6681 1.4035 -0.4341 0.037 Uiso 1 1 calc R . . H9B H 0.5611 1.3334 -0.5017 0.037 Uiso 1 1 calc R . . C26 C 0.8587(4) 1.5011(4) -0.2511(3) 0.0393(9) Uani 1 1 d . . . C4 C 0.2796(3) 1.5912(3) -0.3802(2) 0.0337(8) Uani 1 1 d . . . H4A H 0.2520 1.6383 -0.3585 0.040 Uiso 1 1 calc R . . C13 C 0.6955(3) 1.6954(3) -0.2021(2) 0.0273(7) Uani 1 1 d . . . C18 C 0.7548(3) 1.6532(3) -0.1241(2) 0.0330(8) Uani 1 1 d . . . C22 C 0.6732(4) 1.8226(4) -0.3106(2) 0.0374(9) Uani 1 1 d . . . H22A H 0.6272 1.7575 -0.3449 0.045 Uiso 1 1 calc R . . C17 C 0.8604(4) 1.7046(4) -0.0674(2) 0.0412(9) Uani 1 1 d . . . H17A H 0.9021 1.6796 -0.0147 0.049 Uiso 1 1 calc R . . C6 C 0.2447(3) 1.4509(4) -0.4784(2) 0.0356(8) Uani 1 1 d . . . H6A H 0.1947 1.4039 -0.5219 0.043 Uiso 1 1 calc R . . C8 C 0.4230(3) 1.3882(3) -0.4726(2) 0.0299(7) Uani 1 1 d . . . C19 C 0.7113(4) 1.5541(4) -0.1009(2) 0.0393(9) Uani 1 1 d . . . H19A H 0.6337 1.5345 -0.1475 0.047 Uiso 1 1 calc R . . C16 C 0.9045(4) 1.7912(4) -0.0873(3) 0.0464(11) Uani 1 1 d . . . H16A H 0.9753 1.8238 -0.0481 0.056 Uiso 1 1 calc R . . C11 C 0.7463(4) 1.1904(4) -0.4175(3) 0.0492(11) Uani 1 1 d . . . H11A H 0.7675 1.1126 -0.3967 0.059 Uiso 1 1 calc R . . H11B H 0.7056 1.1861 -0.4749 0.059 Uiso 1 1 calc R . . C25 C 0.9845(4) 1.4914(5) -0.2061(4) 0.0681(17) Uani 1 1 d . . . C15 C 0.8447(4) 1.8304(4) -0.1649(3) 0.0413(10) Uani 1 1 d . . . H15A H 0.8752 1.8897 -0.1774 0.050 Uiso 1 1 calc R . . C12 C 0.8554(5) 1.2605(5) -0.3827(4) 0.0679(17) Uani 1 1 d . . . H12A H 0.9019 1.2254 -0.3968 0.102 Uiso 1 1 calc R . . H12B H 0.8980 1.2628 -0.3257 0.102 Uiso 1 1 calc R . . H12C H 0.8355 1.3375 -0.4036 0.102 Uiso 1 1 calc R . . C23 C 0.7519(5) 1.8601(4) -0.3333(3) 0.0535(13) Uani 1 1 d . . . H23A H 0.8035 1.7983 -0.3231 0.080 Uiso 1 1 calc R . . H23B H 0.7957 1.9262 -0.3023 0.080 Uiso 1 1 calc R . . H23C H 0.7063 1.8795 -0.3890 0.080 Uiso 1 1 calc R . . C24 C 0.5900(5) 1.9190(5) -0.3268(3) 0.0655(16) Uani 1 1 d . . . H24A H 0.5406 1.8939 -0.3124 0.098 Uiso 1 1 calc R . . H24B H 0.5442 1.9385 -0.3824 0.098 Uiso 1 1 calc R . . H24C H 0.6328 1.9854 -0.2957 0.098 Uiso 1 1 calc R . . F4 F 0.9714(2) 1.3991(3) 0.40750(16) 0.0599(8) Uani 1 1 d . . . F3 F 0.8712(5) 1.3858(4) 0.2775(2) 0.146(3) Uani 1 1 d . . . F2 F 1.0305(4) 1.2867(5) 0.3501(3) 0.131(2) Uani 1 1 d . . . B B 0.9391(4) 1.3283(5) 0.3444(3) 0.0383(10) Uani 1 1 d . . . F1 F 0.8777(6) 1.2404(4) 0.3419(4) 0.145(2) Uani 1 1 d . . . C20 C 0.7020(5) 1.5881(5) -0.0338(3) 0.0545(13) Uani 1 1 d . . . H20A H 0.6533 1.6547 -0.0496 0.082 Uiso 1 1 calc R . . H20B H 0.7773 1.6058 0.0132 0.082 Uiso 1 1 calc R . . H20C H 0.6695 1.5255 -0.0228 0.082 Uiso 1 1 calc R . . C21 C 0.7867(6) 1.4477(5) -0.0787(4) 0.0658(16) Uani 1 1 d . . . H21A H 0.7903 1.4275 -0.1221 0.099 Uiso 1 1 calc R . . H21B H 0.7544 1.3847 -0.0678 0.099 Uiso 1 1 calc R . . H21C H 0.8629 1.4638 -0.0321 0.099 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 0.02297(13) 0.02559(15) 0.02377(14) -0.00199(9) 0.01396(11) -0.00074(9) N4 0.0262(14) 0.0340(17) 0.0373(17) -0.0082(13) 0.0193(13) -0.0030(12) N2 0.0227(13) 0.0246(14) 0.0266(14) 0.0010(11) 0.0145(11) -0.0024(10) N3 0.0315(15) 0.0276(15) 0.0251(14) -0.0060(11) 0.0166(12) -0.0023(12) C5 0.0257(17) 0.045(2) 0.042(2) 0.0078(18) 0.0171(17) 0.0011(15) C10 0.042(2) 0.029(2) 0.045(2) 0.0055(16) 0.0285(19) 0.0058(16) O1 0.0439(17) 0.0469(18) 0.0352(16) -0.0171(13) 0.0187(14) -0.0132(14) C1 0.045(2) 0.043(2) 0.043(2) -0.0076(18) 0.032(2) 0.0011(18) N1 0.0296(14) 0.0246(15) 0.0248(14) -0.0045(11) 0.0178(12) -0.0031(11) C7 0.0265(16) 0.0276(18) 0.0273(17) 0.0023(13) 0.0134(14) -0.0043(13) C2 0.0293(17) 0.0310(18) 0.0304(18) 0.0004(14) 0.0215(15) 0.0009(13) C3 0.0256(16) 0.0308(18) 0.0298(18) 0.0053(14) 0.0177(14) 0.0034(13) C14 0.0328(18) 0.0285(18) 0.0324(19) -0.0087(14) 0.0222(16) -0.0067(14) C9 0.039(2) 0.0297(19) 0.0299(18) -0.0011(14) 0.0234(16) 0.0008(15) C26 0.033(2) 0.034(2) 0.049(2) -0.0069(17) 0.0229(19) -0.0053(15) C4 0.0275(17) 0.037(2) 0.041(2) 0.0041(16) 0.0227(16) 0.0032(14) C13 0.0289(16) 0.0293(18) 0.0250(16) -0.0075(13) 0.0165(14) -0.0043(13) C18 0.0352(19) 0.033(2) 0.0287(19) -0.0056(15) 0.0179(16) -0.0011(15) C22 0.048(2) 0.036(2) 0.034(2) -0.0063(16) 0.0272(19) -0.0102(17) C17 0.038(2) 0.049(3) 0.028(2) -0.0070(17) 0.0142(17) -0.0005(18) C6 0.0270(17) 0.037(2) 0.034(2) 0.0025(16) 0.0126(15) -0.0057(15) C8 0.0317(17) 0.0265(18) 0.0264(17) -0.0018(13) 0.0143(15) -0.0050(14) C19 0.050(2) 0.040(2) 0.0279(19) 0.0009(16) 0.0226(18) -0.0019(18) C16 0.034(2) 0.053(3) 0.041(2) -0.022(2) 0.0161(18) -0.0120(18) C11 0.065(3) 0.036(2) 0.060(3) 0.007(2) 0.044(3) 0.018(2) C25 0.028(2) 0.057(3) 0.097(5) -0.001(3) 0.024(3) 0.000(2) C15 0.041(2) 0.041(2) 0.048(2) -0.0170(19) 0.029(2) -0.0161(18) C12 0.076(4) 0.058(3) 0.103(5) 0.027(3) 0.071(4) 0.025(3) C23 0.070(3) 0.054(3) 0.052(3) -0.011(2) 0.045(3) -0.023(2) C24 0.075(4) 0.069(4) 0.065(4) 0.028(3) 0.048(3) 0.022(3) F4 0.0460(16) 0.079(2) 0.0394(15) -0.0140(14) 0.0167(13) 0.0088(14) F3 0.233(6) 0.082(3) 0.041(2) 0.004(2) 0.034(3) 0.052(3) F2 0.069(3) 0.170(5) 0.159(4) -0.086(4) 0.069(3) -0.003(3) B 0.035(2) 0.046(3) 0.034(2) 0.0016(19) 0.0203(19) 0.0037(19) F1 0.227(6) 0.091(3) 0.233(6) -0.064(4) 0.199(6) -0.083(4) C20 0.078(4) 0.052(3) 0.050(3) -0.002(2) 0.047(3) -0.001(3) C21 0.108(5) 0.038(3) 0.079(4) 0.007(3) 0.070(4) 0.008(3) _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 N2 1.915(3) . ? Pd1 N3 1.992(3) . ? Pd1 N4 2.007(3) . ? Pd1 N1 2.049(3) . ? N4 C26 1.127(5) . ? N2 C7 1.327(5) . ? N2 C3 1.345(5) . ? N3 C8 1.342(5) . ? N3 C9 1.454(5) . ? C5 C6 1.378(6) . ? C5 C4 1.397(6) . ? C5 H5A 0.9300 . ? C10 C9 1.517(5) . ? C10 C11 1.521(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O1 C8 1.233(4) . ? C1 C2 1.493(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N1 C2 1.293(4) . ? N1 C13 1.445(4) . ? C7 C6 1.388(5) . ? C7 C8 1.507(5) . ? C2 C3 1.479(5) . ? C3 C4 1.380(5) . ? C14 C15 1.393(5) . ? C14 C13 1.397(5) . ? C14 C22 1.521(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C26 C25 1.469(6) . ? C4 H4A 0.9300 . ? C13 C18 1.400(5) . ? C18 C17 1.392(5) . ? C18 C19 1.516(6) . ? C22 C23 1.519(6) . ? C22 C24 1.521(7) . ? C22 H22A 0.9800 . ? C17 C16 1.372(7) . ? C17 H17A 0.9300 . ? C6 H6A 0.9300 . ? C19 C20 1.523(6) . ? C19 C21 1.523(7) . ? C19 H19A 0.9800 . ? C16 C15 1.382(7) . ? C16 H16A 0.9300 . ? C11 C12 1.517(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C15 H15A 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? F4 B 1.374(6) . ? F3 B 1.315(6) . ? F2 B 1.334(6) . ? B F1 1.327(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pd1 N3 81.35(13) . . ? N2 Pd1 N4 177.00(13) . . ? N3 Pd1 N4 99.03(13) . . ? N2 Pd1 N1 79.80(12) . . ? N3 Pd1 N1 161.10(12) . . ? N4 Pd1 N1 99.87(12) . . ? C26 N4 Pd1 174.8(4) . . ? C7 N2 C3 124.0(3) . . ? C7 N2 Pd1 117.7(2) . . ? C3 N2 Pd1 118.3(2) . . ? C8 N3 C9 119.0(3) . . ? C8 N3 Pd1 114.9(2) . . ? C9 N3 Pd1 125.6(2) . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C9 C10 C11 111.7(3) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 N1 C13 124.0(3) . . ? C2 N1 Pd1 114.2(2) . . ? C13 N1 Pd1 121.8(2) . . ? N2 C7 C6 119.6(4) . . ? N2 C7 C8 113.4(3) . . ? C6 C7 C8 127.0(3) . . ? N1 C2 C3 115.3(3) . . ? N1 C2 C1 125.0(3) . . ? C3 C2 C1 119.7(3) . . ? N2 C3 C4 118.7(3) . . ? N2 C3 C2 112.4(3) . . ? C4 C3 C2 128.9(3) . . ? C15 C14 C13 117.4(4) . . ? C15 C14 C22 121.1(4) . . ? C13 C14 C22 121.4(3) . . ? N3 C9 C10 113.2(3) . . ? N3 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N3 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? N4 C26 C25 179.6(6) . . ? C3 C4 C5 118.4(4) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C14 C13 C18 123.2(3) . . ? C14 C13 N1 117.5(3) . . ? C18 C13 N1 118.8(3) . . ? C17 C18 C13 116.6(4) . . ? C17 C18 C19 120.2(4) . . ? C13 C18 C19 123.2(3) . . ? C23 C22 C24 110.4(4) . . ? C23 C22 C14 112.9(4) . . ? C24 C22 C14 110.7(4) . . ? C23 C22 H22A 107.5 . . ? C24 C22 H22A 107.5 . . ? C14 C22 H22A 107.5 . . ? C16 C17 C18 121.5(4) . . ? C16 C17 H17A 119.2 . . ? C18 C17 H17A 119.2 . . ? C5 C6 C7 118.0(4) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? O1 C8 N3 126.9(4) . . ? O1 C8 C7 120.7(3) . . ? N3 C8 C7 112.4(3) . . ? C18 C19 C20 111.4(4) . . ? C18 C19 C21 111.1(4) . . ? C20 C19 C21 111.2(4) . . ? C18 C19 H19A 107.7 . . ? C20 C19 H19A 107.7 . . ? C21 C19 H19A 107.7 . . ? C17 C16 C15 120.7(4) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? C12 C11 C10 114.1(4) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? F3 B F1 106.6(5) . . ? F3 B F2 111.0(5) . . ? F1 B F2 108.5(5) . . ? F3 B F4 109.1(4) . . ? F1 B F4 110.0(4) . . ? F2 B F4 111.6(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.024 _refine_diff_density_min -0.878 _refine_diff_density_rms 0.108 #==END