# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbad130430_L1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 N2 P2' _chemical_formula_sum 'C23 H30 N2 P2' _chemical_formula_weight 396.43 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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 17.4036(7) _cell_length_b 9.2806(3) _cell_length_c 16.0476(6) _cell_angle_alpha 90.00 _cell_angle_beta 121.1790(10) _cell_angle_gamma 90.00 _cell_volume 2217.55(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6408 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 31.92 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9370 _exptl_absorpt_correction_T_max 0.9599 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14989 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 32.06 _reflns_number_total 7200 _reflns_number_gt 6466 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0427P)^2^+0.2885P] 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 0.06(5) _refine_ls_number_reflns 7200 _refine_ls_number_parameters 250 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.02360(9) 0.73893(13) 0.44169(9) 0.0196(2) Uani 1 1 d . . . C2 C -0.08288(10) 0.79345(17) 0.47277(11) 0.0273(3) Uani 1 1 d . . . H2 H -0.1238 0.8437 0.4847 0.033 Uiso 1 1 calc R . . C3 C -0.07358(10) 0.64919(17) 0.47176(11) 0.0300(3) Uani 1 1 d . . . H3 H -0.1079 0.5809 0.4830 0.036 Uiso 1 1 calc R . . C4 C -0.09423(10) 1.10701(15) 0.34076(11) 0.0266(3) Uani 1 1 d . . . C5 C -0.08929(13) 1.0459(2) 0.25451(12) 0.0360(4) Uani 1 1 d . . . H5A H -0.0891 0.9404 0.2570 0.054 Uiso 1 1 calc R . . H5B H -0.0342 1.0796 0.2584 0.054 Uiso 1 1 calc R . . H5C H -0.1415 1.0787 0.1932 0.054 Uiso 1 1 calc R . . C6 C -0.08503(14) 1.27151(17) 0.34096(16) 0.0410(4) Uani 1 1 d . . . H6A H -0.1328 1.3106 0.2787 0.061 Uiso 1 1 calc R . . H6B H -0.0264 1.2963 0.3500 0.061 Uiso 1 1 calc R . . H6C H -0.0899 1.3127 0.3943 0.061 Uiso 1 1 calc R . . C7 C -0.18565(11) 1.0682(2) 0.32692(13) 0.0374(4) Uani 1 1 d . . . H7A H -0.2335 1.1104 0.2660 0.056 Uiso 1 1 calc R . . H7B H -0.1895 1.1062 0.3816 0.056 Uiso 1 1 calc R . . H7C H -0.1924 0.9632 0.3243 0.056 Uiso 1 1 calc R . . C8 C 0.02388(11) 1.11253(16) 0.56587(11) 0.0290(3) Uani 1 1 d . . . C9 C 0.08111(14) 1.0065(2) 0.64814(13) 0.0432(4) Uani 1 1 d . . . H9A H 0.0991 1.0514 0.7110 0.065 Uiso 1 1 calc R . . H9B H 0.1348 0.9810 0.6462 0.065 Uiso 1 1 calc R . . H9C H 0.0461 0.9194 0.6400 0.065 Uiso 1 1 calc R . . C10 C -0.06016(13) 1.1502(2) 0.56942(14) 0.0402(4) Uani 1 1 d . . . H10A H -0.0968 1.0635 0.5564 0.060 Uiso 1 1 calc R . . H10B H -0.0951 1.2234 0.5201 0.060 Uiso 1 1 calc R . . H10C H -0.0422 1.1877 0.6341 0.060 Uiso 1 1 calc R . . C11 C 0.08020(14) 1.2509(2) 0.58423(15) 0.0432(4) Uani 1 1 d . . . H11A H 0.0955 1.2928 0.6471 0.065 Uiso 1 1 calc R . . H11B H 0.0453 1.3207 0.5322 0.065 Uiso 1 1 calc R . . H11C H 0.1354 1.2269 0.5851 0.065 Uiso 1 1 calc R . . C12 C 0.20473(9) 0.81229(14) 0.52695(10) 0.0216(2) Uani 1 1 d . . . C13 C 0.21962(11) 0.75902(16) 0.61529(12) 0.0286(3) Uani 1 1 d . . . H13 H 0.1800 0.6891 0.6157 0.034 Uiso 1 1 calc R . . C14 C 0.29231(11) 0.80762(18) 0.70300(11) 0.0330(3) Uani 1 1 d . . . H14 H 0.3018 0.7709 0.7629 0.040 Uiso 1 1 calc R . . C15 C 0.35062(11) 0.90901(17) 0.70331(12) 0.0333(3) Uani 1 1 d . . . H15 H 0.4006 0.9410 0.7632 0.040 Uiso 1 1 calc R . . C16 C 0.33597(11) 0.96354(19) 0.61628(13) 0.0361(3) Uani 1 1 d . . . H16 H 0.3756 1.0340 0.6164 0.043 Uiso 1 1 calc R . . C17 C 0.26357(10) 0.91598(16) 0.52838(11) 0.0283(3) Uani 1 1 d . . . H17 H 0.2540 0.9543 0.4688 0.034 Uiso 1 1 calc R . . C18 C 0.12822(9) 0.57372(16) 0.39149(10) 0.0222(3) Uani 1 1 d . . . C19 C 0.18306(11) 0.47722(16) 0.46597(12) 0.0297(3) Uani 1 1 d . . . H19 H 0.2127 0.5078 0.5320 0.036 Uiso 1 1 calc R . . C20 C 0.19437(11) 0.33751(17) 0.44401(13) 0.0349(3) Uani 1 1 d . . . H20 H 0.2319 0.2730 0.4951 0.042 Uiso 1 1 calc R . . C21 C 0.15160(12) 0.29092(18) 0.34848(14) 0.0377(4) Uani 1 1 d . . . H21 H 0.1593 0.1946 0.3341 0.045 Uiso 1 1 calc R . . C22 C 0.09788(12) 0.38416(19) 0.27434(13) 0.0366(4) Uani 1 1 d . . . H22 H 0.0687 0.3526 0.2086 0.044 Uiso 1 1 calc R . . C23 C 0.08626(10) 0.52549(17) 0.29580(11) 0.0275(3) Uani 1 1 d . . . H23 H 0.0491 0.5895 0.2442 0.033 Uiso 1 1 calc R . . N1 N -0.02101(8) 0.85444(12) 0.45296(8) 0.0208(2) Uani 1 1 d . . . N2 N -0.00723(9) 0.61432(13) 0.45207(10) 0.0265(2) Uani 1 1 d . . . P1 P 0.00974(2) 1.03468(3) 0.45044(2) 0.02055(7) Uani 1 1 d . . . P2 P 0.10830(2) 0.76359(4) 0.40800(2) 0.02006(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0199(6) 0.0175(6) 0.0212(6) 0.0003(5) 0.0106(5) 0.0010(4) C2 0.0276(7) 0.0276(7) 0.0349(8) 0.0003(6) 0.0219(6) -0.0011(5) C3 0.0322(7) 0.0268(7) 0.0368(8) 0.0022(6) 0.0221(7) -0.0058(6) C4 0.0289(7) 0.0207(6) 0.0300(7) 0.0046(5) 0.0152(6) 0.0022(5) C5 0.0378(9) 0.0403(10) 0.0271(8) 0.0016(7) 0.0148(7) -0.0022(7) C6 0.0476(10) 0.0220(7) 0.0501(10) 0.0107(7) 0.0230(8) 0.0042(7) C7 0.0265(7) 0.0371(9) 0.0469(10) 0.0086(7) 0.0179(7) 0.0051(6) C8 0.0362(8) 0.0261(7) 0.0310(7) -0.0039(6) 0.0219(7) 0.0007(6) C9 0.0547(11) 0.0425(10) 0.0277(8) -0.0016(7) 0.0179(8) 0.0088(8) C10 0.0487(10) 0.0395(9) 0.0473(10) -0.0075(7) 0.0355(9) 0.0025(7) C11 0.0531(11) 0.0366(9) 0.0468(10) -0.0199(8) 0.0308(9) -0.0139(8) C12 0.0214(6) 0.0182(6) 0.0252(6) -0.0001(5) 0.0120(5) 0.0033(5) C13 0.0325(8) 0.0258(7) 0.0262(7) 0.0016(5) 0.0143(6) 0.0001(6) C14 0.0380(8) 0.0292(8) 0.0237(7) 0.0004(6) 0.0102(6) 0.0061(6) C15 0.0283(7) 0.0277(7) 0.0297(7) -0.0076(6) 0.0050(6) 0.0048(6) C16 0.0284(8) 0.0325(8) 0.0413(9) -0.0045(7) 0.0137(7) -0.0070(6) C17 0.0270(7) 0.0266(7) 0.0320(7) 0.0005(6) 0.0158(6) -0.0018(5) C18 0.0225(6) 0.0206(6) 0.0270(6) -0.0008(5) 0.0152(5) 0.0009(5) C19 0.0315(7) 0.0266(7) 0.0295(7) 0.0011(6) 0.0148(6) 0.0057(6) C20 0.0354(8) 0.0252(7) 0.0465(9) 0.0038(7) 0.0229(7) 0.0087(6) C21 0.0405(9) 0.0254(7) 0.0545(10) -0.0082(7) 0.0298(8) 0.0011(6) C22 0.0388(9) 0.0336(9) 0.0381(9) -0.0118(7) 0.0204(7) -0.0034(7) C23 0.0271(7) 0.0291(7) 0.0259(7) -0.0013(6) 0.0135(6) 0.0004(5) N1 0.0229(5) 0.0173(5) 0.0270(5) 0.0013(4) 0.0165(5) 0.0010(4) N2 0.0305(7) 0.0188(5) 0.0326(6) 0.0022(5) 0.0181(5) -0.0008(4) P1 0.02354(16) 0.01620(15) 0.02625(16) -0.00031(13) 0.01596(13) 0.00017(12) P2 0.02102(15) 0.01933(16) 0.02088(14) 0.00172(13) 0.01159(12) 0.00119(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.3212(17) . ? C1 N1 1.3893(16) . ? C1 P2 1.8282(12) . ? C2 C3 1.350(2) . ? C2 N1 1.3912(17) . ? C2 H2 0.9500 . ? C3 N2 1.3842(19) . ? C3 H3 0.9500 . ? C4 C7 1.531(2) . ? C4 C6 1.535(2) . ? C4 C5 1.539(2) . ? C4 P1 1.8776(15) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.530(2) . ? C8 C10 1.533(2) . ? C8 C11 1.549(2) . ? C8 P1 1.8820(15) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.393(2) . ? C12 C17 1.3967(19) . ? C12 P2 1.8296(14) . ? C13 C14 1.393(2) . ? C13 H13 0.9500 . ? C14 C15 1.382(2) . ? C14 H14 0.9500 . ? C15 C16 1.379(3) . ? C15 H15 0.9500 . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.389(2) . ? C18 C19 1.400(2) . ? C18 P2 1.8413(15) . ? C19 C20 1.384(2) . ? C19 H19 0.9500 . ? C20 C21 1.382(3) . ? C20 H20 0.9500 . ? C21 C22 1.374(3) . ? C21 H21 0.9500 . ? C22 C23 1.397(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 P1 1.7631(12) . ? 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 C1 N1 111.60(11) . . ? N2 C1 P2 126.09(10) . . ? N1 C1 P2 122.16(9) . . ? C3 C2 N1 106.80(12) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 110.73(12) . . ? C2 C3 H3 124.6 . . ? N2 C3 H3 124.6 . . ? C7 C4 C6 109.49(14) . . ? C7 C4 C5 108.70(14) . . ? C6 C4 C5 108.31(14) . . ? C7 C4 P1 118.46(11) . . ? C6 C4 P1 107.74(12) . . ? C5 C4 P1 103.64(11) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C10 108.78(14) . . ? C9 C8 C11 107.70(16) . . ? C10 C8 C11 109.02(14) . . ? C9 C8 P1 107.31(11) . . ? C10 C8 P1 118.87(12) . . ? C11 C8 P1 104.65(10) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.63(13) . . ? C13 C12 P2 124.12(11) . . ? C17 C12 P2 117.13(10) . . ? C12 C13 C14 120.43(15) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.33(15) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.71(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.42(15) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 120.47(14) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C23 C18 C19 118.25(14) . . ? C23 C18 P2 115.91(11) . . ? C19 C18 P2 125.82(11) . . ? C20 C19 C18 120.38(15) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.64(16) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.86(15) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 119.89(16) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C18 C23 C22 120.97(15) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C1 N1 C2 105.46(11) . . ? C1 N1 P1 122.17(9) . . ? C2 N1 P1 132.16(10) . . ? C1 N2 C3 105.39(11) . . ? N1 P1 C4 101.77(6) . . ? N1 P1 C8 103.19(6) . . ? C4 P1 C8 110.92(7) . . ? C1 P2 C12 99.61(6) . . ? C1 P2 C18 99.40(6) . . ? C12 P2 C18 104.31(6) . . ? 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 N1 C2 C3 N2 0.14(18) . . . . ? C17 C12 C13 C14 -0.6(2) . . . . ? P2 C12 C13 C14 -176.54(12) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C15 C16 C17 C12 -0.1(2) . . . . ? C13 C12 C17 C16 0.7(2) . . . . ? P2 C12 C17 C16 176.95(12) . . . . ? C23 C18 C19 C20 -0.3(2) . . . . ? P2 C18 C19 C20 -178.43(12) . . . . ? C18 C19 C20 C21 -0.2(2) . . . . ? C19 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C19 C18 C23 C22 0.5(2) . . . . ? P2 C18 C23 C22 178.80(12) . . . . ? C21 C22 C23 C18 -0.1(2) . . . . ? N2 C1 N1 C2 0.69(16) . . . . ? P2 C1 N1 C2 176.65(10) . . . . ? N2 C1 N1 P1 176.11(10) . . . . ? P2 C1 N1 P1 -7.93(16) . . . . ? C3 C2 N1 C1 -0.48(16) . . . . ? C3 C2 N1 P1 -175.25(11) . . . . ? N1 C1 N2 C3 -0.60(16) . . . . ? P2 C1 N2 C3 -176.37(11) . . . . ? C2 C3 N2 C1 0.28(18) . . . . ? C1 N1 P1 C4 117.09(11) . . . . ? C2 N1 P1 C4 -68.87(15) . . . . ? C1 N1 P1 C8 -127.85(11) . . . . ? C2 N1 P1 C8 46.18(15) . . . . ? C7 C4 P1 N1 43.73(13) . . . . ? C6 C4 P1 N1 168.62(11) . . . . ? C5 C4 P1 N1 -76.73(10) . . . . ? C7 C4 P1 C8 -65.50(14) . . . . ? C6 C4 P1 C8 59.39(13) . . . . ? C5 C4 P1 C8 174.05(10) . . . . ? C9 C8 P1 N1 47.50(13) . . . . ? C10 C8 P1 N1 -76.33(14) . . . . ? C11 C8 P1 N1 161.74(12) . . . . ? C9 C8 P1 C4 155.80(12) . . . . ? C10 C8 P1 C4 31.97(15) . . . . ? C11 C8 P1 C4 -89.96(13) . . . . ? N2 C1 P2 C12 -104.49(13) . . . . ? N1 C1 P2 C12 80.15(12) . . . . ? N2 C1 P2 C18 1.89(13) . . . . ? N1 C1 P2 C18 -173.46(11) . . . . ? C13 C12 P2 C1 32.91(13) . . . . ? C17 C12 P2 C1 -143.10(11) . . . . ? C13 C12 P2 C18 -69.46(13) . . . . ? C17 C12 P2 C18 114.53(11) . . . . ? C23 C18 P2 C1 101.19(11) . . . . ? C19 C18 P2 C1 -80.61(13) . . . . ? C23 C18 P2 C12 -156.28(11) . . . . ? C19 C18 P2 C12 21.92(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.352 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 968367' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbpa130916_L2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 N2 P2' _chemical_formula_sum 'C23 H30 N2 P2' _chemical_formula_weight 396.43 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 12.1693(18) _cell_length_b 21.844(3) _cell_length_c 8.3719(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2225.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2514 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9601 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details sadabs _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 triumph _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16073 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.04 _reflns_number_total 4118 _reflns_number_gt 3099 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0461P)^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 0.32(10) _refine_ls_number_reflns 4118 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C1 C 0.3170(2) 0.38924(13) 0.5808(3) 0.0232(6) Uani 1 1 d . . . C2 C 0.4440(2) 0.37565(14) 0.4055(4) 0.0292(7) Uani 1 1 d . . . H2 H 0.5089 0.3819 0.3446 0.035 Uiso 1 1 calc R . . C3 C 0.3728(2) 0.32906(14) 0.3828(4) 0.0286(7) Uani 1 1 d . . . H3 H 0.3782 0.2975 0.3052 0.034 Uiso 1 1 calc R . . C4 C 0.3251(3) 0.42103(15) 0.9144(4) 0.0338(8) Uani 1 1 d . . . C5 C 0.4186(3) 0.4690(2) 0.9021(5) 0.0582(11) Uani 1 1 d . . . H5A H 0.3871 0.5103 0.9048 0.087 Uiso 1 1 calc R . . H5B H 0.4585 0.4631 0.8016 0.087 Uiso 1 1 calc R . . H5C H 0.4692 0.4639 0.9921 0.087 Uiso 1 1 calc R . . C6 C 0.2564(3) 0.43326(16) 1.0639(4) 0.0427(9) Uani 1 1 d . . . H6A H 0.1970 0.4031 1.0706 0.064 Uiso 1 1 calc R . . H6B H 0.2250 0.4745 1.0581 0.064 Uiso 1 1 calc R . . H6C H 0.3032 0.4300 1.1588 0.064 Uiso 1 1 calc R . . C7 C 0.3757(4) 0.35686(19) 0.9262(5) 0.0628(13) Uani 1 1 d . . . H7A H 0.4219 0.3544 1.0219 0.094 Uiso 1 1 calc R . . H7B H 0.4206 0.3489 0.8312 0.094 Uiso 1 1 calc R . . H7C H 0.3170 0.3263 0.9330 0.094 Uiso 1 1 calc R . . C8 C 0.1944(3) 0.49640(15) 0.6615(4) 0.0342(8) Uani 1 1 d . . . C9 C 0.1153(3) 0.48262(19) 0.5209(6) 0.0699(13) Uani 1 1 d . . . H9A H 0.0850 0.5211 0.4799 0.105 Uiso 1 1 calc R . . H9B H 0.0554 0.4564 0.5584 0.105 Uiso 1 1 calc R . . H9C H 0.1557 0.4617 0.4355 0.105 Uiso 1 1 calc R . . C10 C 0.2844(3) 0.53706(17) 0.5977(5) 0.0573(11) Uani 1 1 d . . . H10A H 0.2518 0.5730 0.5460 0.086 Uiso 1 1 calc R . . H10B H 0.3284 0.5143 0.5198 0.086 Uiso 1 1 calc R . . H10C H 0.3316 0.5504 0.6860 0.086 Uiso 1 1 calc R . . C11 C 0.1290(4) 0.5300(2) 0.7887(5) 0.0758(15) Uani 1 1 d . . . H11A H 0.1786 0.5434 0.8742 0.114 Uiso 1 1 calc R . . H11B H 0.0731 0.5026 0.8329 0.114 Uiso 1 1 calc R . . H11C H 0.0932 0.5658 0.7410 0.114 Uiso 1 1 calc R . . C12 C 0.2413(2) 0.21870(14) 0.5925(3) 0.0242(6) Uani 1 1 d . . . C13 C 0.3529(2) 0.21029(15) 0.6229(4) 0.0296(7) Uani 1 1 d . . . H13 H 0.4028 0.2431 0.6060 0.036 Uiso 1 1 calc R . . C14 C 0.3920(3) 0.15388(14) 0.6779(4) 0.0322(7) Uani 1 1 d . . . H14 H 0.4683 0.1485 0.6979 0.039 Uiso 1 1 calc R . . C15 C 0.3199(3) 0.10608(15) 0.7032(4) 0.0369(8) Uani 1 1 d . . . H15 H 0.3466 0.0677 0.7394 0.044 Uiso 1 1 calc R . . C16 C 0.2088(3) 0.11400(15) 0.6758(4) 0.0360(8) Uani 1 1 d . . . H16 H 0.1593 0.0810 0.6930 0.043 Uiso 1 1 calc R . . C17 C 0.1696(3) 0.16978(14) 0.6234(4) 0.0302(7) Uani 1 1 d . . . H17 H 0.0929 0.1752 0.6080 0.036 Uiso 1 1 calc R . . C18 C 0.1381(2) 0.27256(13) 0.3208(4) 0.0259(7) Uani 1 1 d . . . C19 C 0.0569(3) 0.30984(15) 0.2553(4) 0.0370(8) Uani 1 1 d . . . H19 H 0.0232 0.3405 0.3192 0.044 Uiso 1 1 calc R . . C20 C 0.0250(3) 0.30257(17) 0.0979(4) 0.0469(10) Uani 1 1 d . . . H20 H -0.0302 0.3283 0.0543 0.056 Uiso 1 1 calc R . . C21 C 0.0729(3) 0.25823(17) 0.0041(5) 0.0505(10) Uani 1 1 d . . . H21 H 0.0515 0.2538 -0.1045 0.061 Uiso 1 1 calc R . . C22 C 0.1518(3) 0.22034(17) 0.0675(4) 0.0510(10) Uani 1 1 d . . . H22 H 0.1840 0.1895 0.0028 0.061 Uiso 1 1 calc R . . C23 C 0.1847(3) 0.22673(15) 0.2256(4) 0.0405(8) Uani 1 1 d . . . H23 H 0.2388 0.2001 0.2688 0.049 Uiso 1 1 calc R . . N1 N 0.41012(19) 0.41290(10) 0.5285(3) 0.0282(5) Uani 1 1 d . . . N2 N 0.29059(17) 0.33651(10) 0.4947(3) 0.0220(5) Uani 1 1 d . . . P1 P 0.22772(6) 0.41734(3) 0.74042(10) 0.02377(17) Uani 1 1 d . . . P2 P 0.17616(6) 0.28965(3) 0.52839(10) 0.02470(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0236(14) 0.0233(15) 0.0226(14) 0.0010(12) -0.0026(13) -0.0030(13) C2 0.0259(16) 0.0344(18) 0.0272(17) 0.0057(15) 0.0007(14) 0.0013(14) C3 0.0279(16) 0.0318(18) 0.0260(17) -0.0036(14) 0.0038(14) 0.0012(14) C4 0.0341(18) 0.041(2) 0.0259(17) -0.0046(15) -0.0058(15) 0.0039(16) C5 0.038(2) 0.093(3) 0.043(2) -0.004(2) -0.0153(19) -0.015(2) C6 0.054(2) 0.046(2) 0.028(2) -0.0046(16) -0.0042(16) 0.0050(17) C7 0.082(3) 0.070(3) 0.036(2) -0.005(2) -0.015(2) 0.040(3) C8 0.0306(18) 0.0350(18) 0.0372(19) 0.0036(16) 0.0047(15) 0.0066(15) C9 0.063(3) 0.070(3) 0.077(3) 0.026(3) -0.034(3) -0.008(2) C10 0.050(2) 0.041(2) 0.081(3) 0.009(2) 0.003(2) -0.0030(18) C11 0.097(3) 0.067(3) 0.063(3) 0.018(2) 0.034(3) 0.052(3) C12 0.0242(14) 0.0311(16) 0.0173(14) -0.0013(13) 0.0002(12) -0.0065(13) C13 0.0253(15) 0.0327(18) 0.0310(18) -0.0012(15) -0.0006(13) -0.0039(14) C14 0.0273(16) 0.0386(19) 0.0307(17) 0.0047(15) -0.0062(14) 0.0020(14) C15 0.052(2) 0.0279(17) 0.0313(19) 0.0057(14) 0.0005(16) 0.0004(16) C16 0.039(2) 0.0331(19) 0.0362(19) 0.0033(16) -0.0003(15) -0.0142(16) C17 0.0298(17) 0.0320(18) 0.0287(17) -0.0014(14) 0.0004(14) -0.0050(15) C18 0.0261(15) 0.0249(16) 0.0268(16) -0.0016(13) -0.0059(13) -0.0048(13) C19 0.0361(18) 0.0350(18) 0.040(2) 0.0052(17) -0.0063(17) -0.0034(14) C20 0.046(2) 0.048(2) 0.047(2) 0.0066(19) -0.0224(19) -0.0022(18) C21 0.062(2) 0.051(2) 0.037(2) 0.0014(19) -0.021(2) -0.013(2) C22 0.072(3) 0.045(2) 0.036(2) -0.0109(17) -0.0159(19) 0.0017(19) C23 0.050(2) 0.0382(19) 0.0332(18) -0.0026(16) -0.0108(19) 0.0061(16) N1 0.0251(12) 0.0314(13) 0.0282(13) -0.0017(14) 0.0047(12) -0.0048(10) N2 0.0207(12) 0.0216(12) 0.0237(14) -0.0006(10) 0.0011(10) -0.0014(10) P1 0.0220(3) 0.0274(4) 0.0219(4) -0.0014(4) 0.0012(4) -0.0030(3) P2 0.0207(3) 0.0267(4) 0.0267(4) -0.0019(4) -0.0013(4) -0.0025(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.321(3) . ? C1 N2 1.396(4) . ? C1 P1 1.828(3) . ? C2 C3 1.350(4) . ? C2 N1 1.376(4) . ? C2 H2 0.9500 . ? C3 N2 1.380(4) . ? C3 H3 0.9500 . ? C4 C6 1.529(5) . ? C4 C7 1.534(5) . ? C4 C5 1.550(5) . ? C4 P1 1.880(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C10 1.508(5) . ? C8 C11 1.519(5) . ? C8 C9 1.550(5) . ? C8 P1 1.893(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.394(4) . ? C12 C17 1.404(4) . ? C12 P2 1.822(3) . ? C13 C14 1.399(4) . ? C13 H13 0.9500 . ? C14 C15 1.380(4) . ? C14 H14 0.9500 . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.392(4) . ? C18 C23 1.400(4) . ? C18 P2 1.837(3) . ? C19 C20 1.383(5) . ? C19 H19 0.9500 . ? C20 C21 1.377(5) . ? C20 H20 0.9500 . ? C21 C22 1.374(5) . ? C21 H21 0.9500 . ? C22 C23 1.390(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N2 P2 1.751(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 N1 C1 N2 110.5(2) . . ? N1 C1 P1 128.4(2) . . ? N2 C1 P1 121.2(2) . . ? C3 C2 N1 111.0(3) . . ? C3 C2 H2 124.5 . . ? N1 C2 H2 124.5 . . ? C2 C3 N2 106.3(3) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? C6 C4 C7 109.1(3) . . ? C6 C4 C5 109.7(3) . . ? C7 C4 C5 109.1(3) . . ? C6 C4 P1 107.3(2) . . ? C7 C4 P1 105.3(2) . . ? C5 C4 P1 116.1(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C8 C11 110.1(3) . . ? C10 C8 C9 107.3(3) . . ? C11 C8 C9 107.5(3) . . ? C10 C8 P1 120.4(2) . . ? C11 C8 P1 108.0(3) . . ? C9 C8 P1 102.8(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.2(3) . . ? C13 C12 P2 126.1(2) . . ? C17 C12 P2 115.6(2) . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C19 C18 C23 118.8(3) . . ? C19 C18 P2 115.6(2) . . ? C23 C18 P2 125.6(2) . . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 119.9(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.6(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 119.8(3) . . ? C22 C23 H23 120.1 . . ? C18 C23 H23 120.1 . . ? C1 N1 C2 105.9(2) . . ? C3 N2 C1 106.3(2) . . ? C3 N2 P2 128.1(2) . . ? C1 N2 P2 125.61(19) . . ? C1 P1 C4 101.90(13) . . ? C1 P1 C8 100.26(14) . . ? C4 P1 C8 111.50(15) . . ? N2 P2 C12 101.45(12) . . ? N2 P2 C18 99.63(12) . . ? C12 P2 C18 102.45(13) . . ? 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 N1 C2 C3 N2 -0.1(3) . . . . ? C17 C12 C13 C14 1.9(5) . . . . ? P2 C12 C13 C14 177.4(2) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C13 C14 C15 C16 -0.7(5) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C15 C16 C17 C12 1.9(5) . . . . ? C13 C12 C17 C16 -2.8(5) . . . . ? P2 C12 C17 C16 -178.7(2) . . . . ? C23 C18 C19 C20 -1.5(5) . . . . ? P2 C18 C19 C20 177.4(3) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C20 C21 C22 0.9(6) . . . . ? C20 C21 C22 C23 -0.7(6) . . . . ? C21 C22 C23 C18 -0.6(5) . . . . ? C19 C18 C23 C22 1.7(5) . . . . ? P2 C18 C23 C22 -177.1(3) . . . . ? N2 C1 N1 C2 0.9(3) . . . . ? P1 C1 N1 C2 -178.8(2) . . . . ? C3 C2 N1 C1 -0.5(3) . . . . ? C2 C3 N2 C1 0.6(3) . . . . ? C2 C3 N2 P2 -178.4(2) . . . . ? N1 C1 N2 C3 -0.9(3) . . . . ? P1 C1 N2 C3 178.8(2) . . . . ? N1 C1 N2 P2 178.13(19) . . . . ? P1 C1 N2 P2 -2.2(3) . . . . ? N1 C1 P1 C4 -56.0(3) . . . . ? N2 C1 P1 C4 124.4(2) . . . . ? N1 C1 P1 C8 58.8(3) . . . . ? N2 C1 P1 C8 -120.8(2) . . . . ? C6 C4 P1 C1 -170.2(2) . . . . ? C7 C4 P1 C1 -54.2(3) . . . . ? C5 C4 P1 C1 66.6(3) . . . . ? C6 C4 P1 C8 83.6(3) . . . . ? C7 C4 P1 C8 -160.3(2) . . . . ? C5 C4 P1 C8 -39.5(3) . . . . ? C10 C8 P1 C1 -46.7(3) . . . . ? C11 C8 P1 C1 -174.2(3) . . . . ? C9 C8 P1 C1 72.4(3) . . . . ? C10 C8 P1 C4 60.6(3) . . . . ? C11 C8 P1 C4 -66.9(3) . . . . ? C9 C8 P1 C4 179.6(3) . . . . ? C3 N2 P2 C12 64.0(3) . . . . ? C1 N2 P2 C12 -114.8(2) . . . . ? C3 N2 P2 C18 -40.9(3) . . . . ? C1 N2 P2 C18 140.3(2) . . . . ? C13 C12 P2 N2 6.9(3) . . . . ? C17 C12 P2 N2 -177.5(2) . . . . ? C13 C12 P2 C18 109.6(3) . . . . ? C17 C12 P2 C18 -74.8(2) . . . . ? C19 C18 P2 N2 -95.6(2) . . . . ? C23 C18 P2 N2 83.3(3) . . . . ? C19 C18 P2 C12 160.3(2) . . . . ? C23 C18 P2 C12 -20.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.363 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 968368' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbad130711_comp1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H33 Cl N2 P2 Pd' _chemical_formula_sum 'C24 H33 Cl N2 P2 Pd' _chemical_formula_weight 553.31 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' P P 0.1023 0.0942 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.0415(2) _cell_length_b 14.3830(4) _cell_length_c 21.4302(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.664(2) _cell_angle_gamma 90.00 _cell_volume 2461.89(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9810 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66986 _exptl_absorpt_correction_T_max 0.81271 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15023 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5627 _reflns_number_gt 4860 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0352P)^2^+1.8784P] 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 5627 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 C1 C 0.8880(3) 0.34092(16) 0.57697(11) 0.0198(5) Uani 1 1 d . . . C2 C 1.0261(3) 0.43537(16) 0.64483(12) 0.0221(5) Uani 1 1 d . . . H2 H 1.0758 0.4642 0.6823 0.026 Uiso 1 1 calc R . . C3 C 1.0376(3) 0.46385(18) 0.58537(12) 0.0252(5) Uani 1 1 d . . . H3 H 1.0974 0.5173 0.5746 0.030 Uiso 1 1 calc R . . C4 C 0.5984(3) 0.30149(17) 0.49558(11) 0.0210(5) Uani 1 1 d . . . C5 C 0.4489(3) 0.33024(19) 0.51646(13) 0.0294(6) Uani 1 1 d . . . H5 H 0.4222 0.3118 0.5567 0.035 Uiso 1 1 calc R . . C6 C 0.3390(3) 0.3861(2) 0.47814(14) 0.0356(7) Uani 1 1 d . . . H6 H 0.2373 0.4062 0.4924 0.043 Uiso 1 1 calc R . . C7 C 0.3767(3) 0.4125(2) 0.41955(13) 0.0321(6) Uani 1 1 d . . . H7 H 0.3011 0.4508 0.3937 0.039 Uiso 1 1 calc R . . C8 C 0.5239(4) 0.3835(2) 0.39818(13) 0.0332(6) Uani 1 1 d . . . H8 H 0.5491 0.4014 0.3577 0.040 Uiso 1 1 calc R . . C9 C 0.6346(3) 0.32819(18) 0.43628(12) 0.0271(6) Uani 1 1 d . . . H9 H 0.7360 0.3084 0.4217 0.033 Uiso 1 1 calc R . . C10 C 0.8801(3) 0.17593(17) 0.50003(12) 0.0215(5) Uani 1 1 d . . . C11 C 1.0475(3) 0.1947(2) 0.49593(14) 0.0351(7) Uani 1 1 d . . . H11 H 1.1011 0.2447 0.5192 0.042 Uiso 1 1 calc R . . C12 C 1.1375(4) 0.1404(2) 0.45777(15) 0.0402(7) Uani 1 1 d . . . H12 H 1.2516 0.1546 0.4545 0.048 Uiso 1 1 calc R . . C13 C 1.0628(4) 0.0663(2) 0.42480(13) 0.0339(6) Uani 1 1 d . . . H13 H 1.1252 0.0287 0.3994 0.041 Uiso 1 1 calc R . . C14 C 0.8961(4) 0.04731(19) 0.42899(13) 0.0316(6) Uani 1 1 d . . . H14 H 0.8439 -0.0036 0.4063 0.038 Uiso 1 1 calc R . . C15 C 0.8049(3) 0.10136(18) 0.46573(12) 0.0288(6) Uani 1 1 d . . . H15 H 0.6900 0.0879 0.4678 0.035 Uiso 1 1 calc R . . C16 C 0.7222(3) 0.35775(17) 0.73948(11) 0.0217(5) Uani 1 1 d . . . C17 C 0.6800(4) 0.3072(2) 0.79864(14) 0.0346(6) Uani 1 1 d . . . H17A H 0.7795 0.3053 0.8297 0.052 Uiso 1 1 calc R . . H17B H 0.6435 0.2437 0.7877 0.052 Uiso 1 1 calc R . . H17C H 0.5899 0.3405 0.8163 0.052 Uiso 1 1 calc R . . C18 C 0.7946(3) 0.45394(18) 0.75744(13) 0.0277(6) Uani 1 1 d . . . H18A H 0.7166 0.4880 0.7810 0.042 Uiso 1 1 calc R . . H18B H 0.8111 0.4886 0.7193 0.042 Uiso 1 1 calc R . . H18C H 0.9022 0.4468 0.7835 0.042 Uiso 1 1 calc R . . C19 C 0.5608(3) 0.3724(2) 0.69439(14) 0.0309(6) Uani 1 1 d . . . H19A H 0.5049 0.3124 0.6857 0.046 Uiso 1 1 calc R . . H19B H 0.5889 0.3995 0.6550 0.046 Uiso 1 1 calc R . . H19C H 0.4859 0.4145 0.7138 0.046 Uiso 1 1 calc R . . C20 C 1.0579(3) 0.24291(17) 0.74224(12) 0.0240(5) Uani 1 1 d . . . C21 C 1.1590(3) 0.1988(2) 0.69333(14) 0.0365(7) Uani 1 1 d . . . H21A H 1.1887 0.2468 0.6641 0.055 Uiso 1 1 calc R . . H21B H 1.0914 0.1507 0.6700 0.055 Uiso 1 1 calc R . . H21C H 1.2612 0.1708 0.7147 0.055 Uiso 1 1 calc R . . C22 C 1.0153(4) 0.1675(2) 0.78851(16) 0.0406(8) Uani 1 1 d . . . H22A H 1.1187 0.1376 0.8073 0.061 Uiso 1 1 calc R . . H22B H 0.9422 0.1209 0.7661 0.061 Uiso 1 1 calc R . . H22C H 0.9579 0.1958 0.8217 0.061 Uiso 1 1 calc R . . C23 C 1.1629(4) 0.3181(2) 0.77843(15) 0.0367(7) Uani 1 1 d . . . H23A H 1.2644 0.2901 0.8004 0.055 Uiso 1 1 calc R . . H23B H 1.0976 0.3470 0.8091 0.055 Uiso 1 1 calc R . . H23C H 1.1941 0.3655 0.7490 0.055 Uiso 1 1 calc R . . C24 C 0.5222(3) 0.0893(2) 0.57716(13) 0.0309(6) Uani 1 1 d . . . H24A H 0.5061 0.1158 0.5348 0.046 Uiso 1 1 calc R . . H24B H 0.4147 0.0876 0.5945 0.046 Uiso 1 1 calc R . . H24C H 0.5664 0.0260 0.5753 0.046 Uiso 1 1 calc R . . N1 N 0.9275(2) 0.35578(13) 0.64047(9) 0.0168(4) Uani 1 1 d . . . N2 N 0.9508(3) 0.40486(15) 0.54249(10) 0.0260(5) Uani 1 1 d . . . P1 P 0.75592(7) 0.24322(4) 0.54968(3) 0.01818(13) Uani 1 1 d . . . P2 P 0.85733(7) 0.28075(4) 0.69607(3) 0.01624(13) Uani 1 1 d . . . Cl1 Cl 0.62853(9) 0.07546(5) 0.71929(3) 0.03824(18) Uani 1 1 d . . . Pd1 Pd 0.69152(2) 0.171259(12) 0.634623(8) 0.01848(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0227(12) 0.0176(12) 0.0196(12) -0.0004(9) 0.0051(9) -0.0036(10) C2 0.0234(12) 0.0163(12) 0.0268(13) -0.0022(10) 0.0043(10) -0.0061(10) C3 0.0293(13) 0.0206(12) 0.0267(13) 0.0012(10) 0.0077(10) -0.0082(11) C4 0.0207(11) 0.0211(12) 0.0204(12) -0.0019(10) -0.0004(9) -0.0021(10) C5 0.0206(12) 0.0400(16) 0.0281(14) 0.0049(11) 0.0041(10) -0.0006(11) C6 0.0213(12) 0.0470(18) 0.0387(16) 0.0052(14) 0.0038(11) 0.0064(12) C7 0.0285(13) 0.0332(15) 0.0325(15) 0.0051(12) -0.0053(11) 0.0045(12) C8 0.0400(15) 0.0361(16) 0.0230(13) 0.0046(12) 0.0025(11) 0.0047(13) C9 0.0282(13) 0.0299(15) 0.0235(13) -0.0007(10) 0.0040(10) 0.0066(11) C10 0.0239(12) 0.0220(13) 0.0183(12) 0.0018(9) 0.0012(9) 0.0034(10) C11 0.0252(13) 0.0438(17) 0.0366(16) -0.0124(14) 0.0052(11) -0.0022(13) C12 0.0264(14) 0.056(2) 0.0389(17) -0.0099(15) 0.0073(12) 0.0058(14) C13 0.0432(16) 0.0341(16) 0.0248(13) 0.0006(12) 0.0051(12) 0.0177(13) C14 0.0480(16) 0.0220(13) 0.0249(13) -0.0016(11) 0.0047(12) 0.0018(12) C15 0.0334(14) 0.0246(13) 0.0287(14) -0.0020(11) 0.0056(11) -0.0045(11) C16 0.0251(12) 0.0188(12) 0.0222(12) 0.0001(10) 0.0077(9) -0.0006(10) C17 0.0463(17) 0.0305(15) 0.0305(15) 0.0000(12) 0.0194(13) -0.0036(13) C18 0.0347(14) 0.0201(13) 0.0295(14) -0.0047(11) 0.0089(11) -0.0009(11) C19 0.0228(12) 0.0303(15) 0.0401(16) -0.0057(12) 0.0055(11) 0.0038(11) C20 0.0241(12) 0.0194(12) 0.0275(13) 0.0024(10) -0.0017(10) 0.0032(10) C21 0.0291(14) 0.0377(16) 0.0418(17) -0.0050(14) 0.0007(12) 0.0130(13) C22 0.0401(17) 0.0358(17) 0.0439(19) 0.0199(14) -0.0041(14) 0.0039(13) C23 0.0315(15) 0.0319(16) 0.0421(18) -0.0025(13) -0.0150(13) -0.0008(12) C24 0.0276(13) 0.0338(15) 0.0311(14) -0.0041(12) 0.0020(11) -0.0169(12) N1 0.0185(9) 0.0131(9) 0.0192(10) -0.0002(8) 0.0037(7) -0.0027(8) N2 0.0312(11) 0.0247(11) 0.0228(11) 0.0040(9) 0.0052(9) -0.0067(9) P1 0.0181(3) 0.0183(3) 0.0180(3) 0.0006(2) 0.0015(2) -0.0030(2) P2 0.0190(3) 0.0128(3) 0.0172(3) 0.0016(2) 0.0031(2) -0.0015(2) Cl1 0.0488(4) 0.0326(4) 0.0342(4) 0.0087(3) 0.0084(3) -0.0179(3) Pd1 0.01928(11) 0.01534(11) 0.02123(11) -0.00006(7) 0.00408(7) -0.00420(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.317(3) . ? C1 N1 1.378(3) . ? C1 P1 1.817(2) . ? C2 C3 1.352(3) . ? C2 N1 1.389(3) . ? C2 H2 0.9500 . ? C3 N2 1.379(3) . ? C3 H3 0.9500 . ? C4 C9 1.390(4) . ? C4 C5 1.393(3) . ? C4 P1 1.820(2) . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.379(4) . ? C6 H6 0.9500 . ? C7 C8 1.382(4) . ? C7 H7 0.9500 . ? C8 C9 1.387(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.386(4) . ? C10 C15 1.398(4) . ? C10 P1 1.820(3) . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C18 1.533(3) . ? C16 C17 1.533(4) . ? C16 C19 1.540(4) . ? C16 P2 1.873(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C23 1.527(4) . ? C20 C22 1.535(4) . ? C20 C21 1.536(4) . ? C20 P2 1.872(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 Pd1 2.091(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N1 P2 1.749(2) . ? P1 Pd1 2.2072(6) . ? P2 Pd1 2.3632(6) . ? Cl1 Pd1 2.3792(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 112.7(2) . . ? N2 C1 P1 127.41(19) . . ? N1 C1 P1 119.80(17) . . ? C3 C2 N1 106.7(2) . . ? C3 C2 H2 126.7 . . ? N1 C2 H2 126.7 . . ? C2 C3 N2 110.9(2) . . ? C2 C3 H3 124.5 . . ? N2 C3 H3 124.5 . . ? C9 C4 C5 119.5(2) . . ? C9 C4 P1 120.35(19) . . ? C5 C4 P1 119.67(19) . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.4(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C4 120.5(2) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C11 C10 C15 118.7(2) . . ? C11 C10 P1 122.5(2) . . ? C15 C10 P1 118.84(19) . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.3(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C18 C16 C17 109.5(2) . . ? C18 C16 C19 107.6(2) . . ? C17 C16 C19 109.4(2) . . ? C18 C16 P2 115.69(17) . . ? C17 C16 P2 109.13(18) . . ? C19 C16 P2 105.33(17) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C23 C20 C22 108.9(2) . . ? C23 C20 C21 109.5(2) . . ? C22 C20 C21 108.9(2) . . ? C23 C20 P2 116.99(18) . . ? C22 C20 P2 107.68(18) . . ? C21 C20 P2 104.54(17) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Pd1 C24 H24A 109.5 . . ? Pd1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? Pd1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C1 N1 C2 104.99(19) . . ? C1 N1 P2 121.45(16) . . ? C2 N1 P2 133.56(17) . . ? C1 N2 C3 104.7(2) . . ? C1 P1 C4 100.76(11) . . ? C1 P1 C10 105.05(11) . . ? C4 P1 C10 105.13(11) . . ? C1 P1 Pd1 106.36(8) . . ? C4 P1 Pd1 121.92(8) . . ? C10 P1 Pd1 115.46(8) . . ? N1 P2 C20 102.31(10) . . ? N1 P2 C16 103.01(10) . . ? C20 P2 C16 115.04(11) . . ? N1 P2 Pd1 103.72(7) . . ? C20 P2 Pd1 119.76(8) . . ? C16 P2 Pd1 110.40(8) . . ? C24 Pd1 P1 88.73(8) . . ? C24 Pd1 P2 172.21(8) . . ? P1 Pd1 P2 88.62(2) . . ? C24 Pd1 Cl1 86.61(8) . . ? P1 Pd1 Cl1 172.57(3) . . ? P2 Pd1 Cl1 96.73(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.5(3) . . . . ? C9 C4 C5 C6 -0.8(4) . . . . ? P1 C4 C5 C6 170.9(2) . . . . ? C4 C5 C6 C7 0.5(4) . . . . ? C5 C6 C7 C8 0.2(5) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C7 C8 C9 C4 0.2(4) . . . . ? C5 C4 C9 C8 0.5(4) . . . . ? P1 C4 C9 C8 -171.2(2) . . . . ? C15 C10 C11 C12 0.6(4) . . . . ? P1 C10 C11 C12 179.2(2) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C10 -0.7(4) . . . . ? C11 C10 C15 C14 0.5(4) . . . . ? P1 C10 C15 C14 -178.2(2) . . . . ? N2 C1 N1 C2 -1.2(3) . . . . ? P1 C1 N1 C2 -179.11(17) . . . . ? N2 C1 N1 P2 179.54(17) . . . . ? P1 C1 N1 P2 1.6(3) . . . . ? C3 C2 N1 C1 1.0(3) . . . . ? C3 C2 N1 P2 -179.87(18) . . . . ? N1 C1 N2 C3 0.9(3) . . . . ? P1 C1 N2 C3 178.60(19) . . . . ? C2 C3 N2 C1 -0.2(3) . . . . ? N2 C1 P1 C4 -49.3(3) . . . . ? N1 C1 P1 C4 128.31(19) . . . . ? N2 C1 P1 C10 59.8(3) . . . . ? N1 C1 P1 C10 -122.64(19) . . . . ? N2 C1 P1 Pd1 -177.4(2) . . . . ? N1 C1 P1 Pd1 0.2(2) . . . . ? C9 C4 P1 C1 77.0(2) . . . . ? C5 C4 P1 C1 -94.6(2) . . . . ? C9 C4 P1 C10 -32.0(2) . . . . ? C5 C4 P1 C10 156.4(2) . . . . ? C9 C4 P1 Pd1 -165.84(17) . . . . ? C5 C4 P1 Pd1 22.5(3) . . . . ? C11 C10 P1 C1 8.8(3) . . . . ? C15 C10 P1 C1 -172.5(2) . . . . ? C11 C10 P1 C4 114.7(2) . . . . ? C15 C10 P1 C4 -66.7(2) . . . . ? C11 C10 P1 Pd1 -108.0(2) . . . . ? C15 C10 P1 Pd1 70.6(2) . . . . ? C1 N1 P2 C20 122.75(19) . . . . ? C2 N1 P2 C20 -56.3(2) . . . . ? C1 N1 P2 C16 -117.57(19) . . . . ? C2 N1 P2 C16 63.4(2) . . . . ? C1 N1 P2 Pd1 -2.44(19) . . . . ? C2 N1 P2 Pd1 178.5(2) . . . . ? C23 C20 P2 N1 63.3(2) . . . . ? C22 C20 P2 N1 -173.70(19) . . . . ? C21 C20 P2 N1 -57.95(19) . . . . ? C23 C20 P2 C16 -47.5(2) . . . . ? C22 C20 P2 C16 75.4(2) . . . . ? C21 C20 P2 C16 -168.83(17) . . . . ? C23 C20 P2 Pd1 177.19(18) . . . . ? C22 C20 P2 Pd1 -59.8(2) . . . . ? C21 C20 P2 Pd1 55.9(2) . . . . ? C18 C16 P2 N1 -44.5(2) . . . . ? C17 C16 P2 N1 -168.48(18) . . . . ? C19 C16 P2 N1 74.16(18) . . . . ? C18 C16 P2 C20 66.0(2) . . . . ? C17 C16 P2 C20 -58.0(2) . . . . ? C19 C16 P2 C20 -175.38(17) . . . . ? C18 C16 P2 Pd1 -154.70(16) . . . . ? C17 C16 P2 Pd1 81.29(19) . . . . ? C19 C16 P2 Pd1 -36.06(18) . . . . ? C1 P1 Pd1 C24 171.39(12) . . . . ? C4 P1 Pd1 C24 57.05(13) . . . . ? C10 P1 Pd1 C24 -72.54(12) . . . . ? C1 P1 Pd1 P2 -1.29(8) . . . . ? C4 P1 Pd1 P2 -115.63(10) . . . . ? C10 P1 Pd1 P2 114.78(9) . . . . ? N1 P2 Pd1 P1 1.91(7) . . . . ? C20 P2 Pd1 P1 -111.20(10) . . . . ? C16 P2 Pd1 P1 111.67(9) . . . . ? N1 P2 Pd1 Cl1 176.74(7) . . . . ? C20 P2 Pd1 Cl1 63.63(10) . . . . ? C16 P2 Pd1 Cl1 -73.50(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.494 _refine_diff_density_min -1.197 _refine_diff_density_rms 0.154 _database_code_depnum_ccdc_archive 'CCDC 968369' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbpa131007_compl2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 Cl2 N2 P2 Pd' _chemical_formula_sum 'C23 H30 Cl2 N2 P2 Pd' _chemical_formula_weight 573.73 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' P P 0.1023 0.0942 '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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.7407(3) _cell_length_b 14.4492(4) _cell_length_c 17.6018(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2477.37(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9849 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.98 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7323 _exptl_absorpt_correction_T_max 0.8973 _exptl_absorpt_process_details sadabs _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 triumph _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24097 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 31.00 _reflns_number_total 7875 _reflns_number_gt 7425 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0185P)^2^+0.2516P] 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 -0.022(12) _refine_ls_number_reflns 7875 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0190 _refine_ls_wR_factor_ref 0.0423 _refine_ls_wR_factor_gt 0.0412 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.004 _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 C1 C 0.60623(16) 0.46212(9) 0.95805(8) 0.0168(3) Uani 1 1 d . . . C2 C 0.82040(15) 0.47563(13) 0.91770(9) 0.0213(3) Uani 1 1 d . . . H2 H 0.8997 0.4870 0.8877 0.026 Uiso 1 1 calc R . . C3 C 0.81671(17) 0.44554(12) 0.99073(10) 0.0231(3) Uani 1 1 d . . . H3 H 0.8956 0.4320 1.0205 0.028 Uiso 1 1 calc R . . C4 C 0.35286(17) 0.35654(11) 0.97400(10) 0.0220(3) Uani 1 1 d . . . C5 C 0.19681(19) 0.35241(15) 0.96417(14) 0.0396(5) Uani 1 1 d . . . H5A H 0.1657 0.2882 0.9695 0.059 Uiso 1 1 calc R . . H5B H 0.1721 0.3755 0.9137 0.059 Uiso 1 1 calc R . . H5C H 0.1528 0.3908 1.0031 0.059 Uiso 1 1 calc R . . C6 C 0.4204(2) 0.29085(12) 0.91642(10) 0.0288(4) Uani 1 1 d . . . H6A H 0.3789 0.2293 0.9207 0.043 Uiso 1 1 calc R . . H6B H 0.5190 0.2866 0.9270 0.043 Uiso 1 1 calc R . . H6C H 0.4065 0.3148 0.8649 0.043 Uiso 1 1 calc R . . C7 C 0.3912(2) 0.32597(12) 1.05477(9) 0.0286(4) Uani 1 1 d . . . H7A H 0.3360 0.3606 1.0917 0.043 Uiso 1 1 calc R . . H7B H 0.4888 0.3382 1.0637 0.043 Uiso 1 1 calc R . . H7C H 0.3732 0.2596 1.0605 0.043 Uiso 1 1 calc R . . C8 C 0.37943(18) 0.56813(11) 1.02020(9) 0.0223(3) Uani 1 1 d . . . C9 C 0.22401(19) 0.58708(15) 1.02247(11) 0.0329(4) Uani 1 1 d . . . H9A H 0.2065 0.6437 1.0516 0.049 Uiso 1 1 calc R . . H9B H 0.1771 0.5349 1.0467 0.049 Uiso 1 1 calc R . . H9C H 0.1895 0.5948 0.9705 0.049 Uiso 1 1 calc R . . C10 C 0.4542(2) 0.65475(12) 0.99051(11) 0.0303(4) Uani 1 1 d . . . H10A H 0.4366 0.7069 1.0247 0.045 Uiso 1 1 calc R . . H10B H 0.4205 0.6698 0.9395 0.045 Uiso 1 1 calc R . . H10C H 0.5531 0.6426 0.9884 0.045 Uiso 1 1 calc R . . C11 C 0.43116(19) 0.54560(13) 1.10095(9) 0.0284(4) Uani 1 1 d . . . H11A H 0.5244 0.5203 1.0980 0.043 Uiso 1 1 calc R . . H11B H 0.3701 0.5000 1.1245 0.043 Uiso 1 1 calc R . . H11C H 0.4319 0.6022 1.1316 0.043 Uiso 1 1 calc R . . C12 C 0.67607(15) 0.42161(10) 0.74876(9) 0.0177(3) Uani 1 1 d . . . C13 C 0.71213(17) 0.33599(12) 0.77924(11) 0.0227(4) Uani 1 1 d . . . H13 H 0.7065 0.3262 0.8325 0.027 Uiso 1 1 calc R . . C14 C 0.75635(18) 0.26493(12) 0.73201(11) 0.0264(4) Uani 1 1 d . . . H14 H 0.7810 0.2066 0.7529 0.032 Uiso 1 1 calc R . . C15 C 0.76425(19) 0.27951(12) 0.65468(11) 0.0298(4) Uani 1 1 d . . . H15 H 0.7963 0.2314 0.6225 0.036 Uiso 1 1 calc R . . C16 C 0.7258(2) 0.36401(14) 0.62341(11) 0.0302(4) Uani 1 1 d . . . H16 H 0.7292 0.3729 0.5700 0.036 Uiso 1 1 calc R . . C17 C 0.68249(17) 0.43531(11) 0.67038(10) 0.0237(3) Uani 1 1 d . . . H17 H 0.6572 0.4934 0.6492 0.028 Uiso 1 1 calc R . . C18 C 0.69328(17) 0.61928(11) 0.78236(9) 0.0175(3) Uani 1 1 d . . . C19 C 0.82482(17) 0.61980(12) 0.75131(10) 0.0244(3) Uani 1 1 d . . . H19 H 0.8707 0.5632 0.7408 0.029 Uiso 1 1 calc R . . C20 C 0.8884(2) 0.70404(13) 0.73589(10) 0.0333(4) Uani 1 1 d . . . H20 H 0.9778 0.7050 0.7143 0.040 Uiso 1 1 calc R . . C21 C 0.8218(2) 0.78642(14) 0.75184(10) 0.0342(5) Uani 1 1 d . . . H21 H 0.8662 0.8436 0.7415 0.041 Uiso 1 1 calc R . . C22 C 0.6917(2) 0.78614(13) 0.78256(10) 0.0319(4) Uani 1 1 d . . . H22 H 0.6468 0.8430 0.7933 0.038 Uiso 1 1 calc R . . C23 C 0.62615(19) 0.70306(11) 0.79780(9) 0.0230(3) Uani 1 1 d . . . H23 H 0.5362 0.7029 0.8186 0.028 Uiso 1 1 calc R . . N1 N 0.68482(12) 0.48632(10) 0.89604(7) 0.0166(2) Uani 1 1 d . . . N2 N 0.68283(14) 0.43715(10) 1.01610(8) 0.0222(3) Uani 1 1 d . . . P1 P 0.41972(4) 0.47444(3) 0.94994(2) 0.01541(7) Uani 1 1 d . . . P2 P 0.61212(4) 0.51263(3) 0.809551(19) 0.01405(6) Uani 1 1 d . . . Cl1 Cl 0.14699(3) 0.52844(3) 0.82951(2) 0.02387(8) Uani 1 1 d . . . Cl2 Cl 0.39076(5) 0.55731(3) 0.69606(2) 0.02351(7) Uani 1 1 d . . . Pd1 Pd 0.387611(10) 0.516726(7) 0.826122(6) 0.01379(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0160(6) 0.0202(6) 0.0143(6) 0.0016(5) -0.0004(6) 0.0008(6) C2 0.0111(6) 0.0296(8) 0.0230(8) 0.0009(7) -0.0004(5) 0.0009(7) C3 0.0161(7) 0.0304(8) 0.0228(8) 0.0018(7) -0.0046(6) 0.0032(6) C4 0.0201(8) 0.0226(7) 0.0233(8) 0.0088(6) 0.0016(6) -0.0030(6) C5 0.0202(9) 0.0390(11) 0.0597(14) 0.0214(10) -0.0019(9) -0.0093(8) C6 0.0382(11) 0.0235(8) 0.0246(9) 0.0030(6) -0.0007(7) -0.0043(7) C7 0.0339(9) 0.0302(8) 0.0216(8) 0.0107(6) 0.0050(8) 0.0011(8) C8 0.0219(8) 0.0271(7) 0.0178(7) -0.0021(6) 0.0022(7) 0.0028(7) C9 0.0257(9) 0.0457(11) 0.0274(10) -0.0024(8) 0.0053(8) 0.0130(8) C10 0.0414(11) 0.0237(8) 0.0259(10) -0.0032(7) 0.0039(8) 0.0013(8) C11 0.0301(9) 0.0382(9) 0.0170(8) -0.0017(7) 0.0034(7) 0.0024(7) C12 0.0134(7) 0.0184(7) 0.0212(8) -0.0010(6) 0.0029(6) -0.0007(6) C13 0.0209(8) 0.0215(8) 0.0256(9) 0.0027(6) 0.0007(7) 0.0007(6) C14 0.0202(8) 0.0173(7) 0.0419(11) -0.0014(7) -0.0006(8) 0.0000(6) C15 0.0247(8) 0.0245(8) 0.0400(11) -0.0139(8) 0.0048(8) -0.0016(7) C16 0.0351(10) 0.0314(9) 0.0242(9) -0.0074(7) 0.0077(8) -0.0010(8) C17 0.0279(8) 0.0224(7) 0.0207(8) 0.0004(7) 0.0042(7) 0.0025(6) C18 0.0174(7) 0.0198(7) 0.0152(8) 0.0023(6) -0.0009(6) -0.0025(6) C19 0.0188(8) 0.0286(8) 0.0259(9) 0.0021(7) 0.0014(7) -0.0032(7) C20 0.0286(9) 0.0415(10) 0.0298(9) 0.0047(7) 0.0009(9) -0.0181(9) C21 0.0500(12) 0.0310(9) 0.0217(9) 0.0052(7) -0.0094(9) -0.0221(9) C22 0.0529(13) 0.0209(8) 0.0220(9) 0.0015(7) -0.0072(8) -0.0035(8) C23 0.0278(9) 0.0217(7) 0.0194(7) 0.0006(6) -0.0014(7) 0.0020(7) N1 0.0119(5) 0.0234(6) 0.0146(6) 0.0013(5) 0.0011(4) -0.0009(5) N2 0.0159(6) 0.0327(7) 0.0180(7) 0.0037(6) -0.0007(5) 0.0026(6) P1 0.01258(16) 0.01911(17) 0.01455(17) 0.00311(15) 0.00170(12) 0.00070(14) P2 0.01188(14) 0.01668(14) 0.01358(15) 0.00150(12) 0.00206(13) 0.00034(16) Cl1 0.01140(14) 0.02895(18) 0.03125(19) 0.00460(19) 0.00032(14) 0.00006(13) Cl2 0.02339(18) 0.03314(19) 0.01399(15) 0.00161(13) -0.00310(15) 0.00234(18) Pd1 0.01095(4) 0.01623(4) 0.01419(5) 0.00119(4) -0.00043(4) 0.00013(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.3157(19) . ? C1 N1 1.3783(18) . ? C1 P1 1.8310(16) . ? C2 C3 1.358(2) . ? C2 N1 1.3832(18) . ? C2 H2 0.9500 . ? C3 N2 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.531(2) . ? C4 C7 1.535(2) . ? C4 C6 1.537(2) . ? C4 P1 1.8723(16) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.539(3) . ? C8 C10 1.539(2) . ? C8 C11 1.543(2) . ? C8 P1 1.8751(16) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.394(2) . ? C12 C17 1.395(2) . ? C12 P2 1.8063(16) . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C14 C15 1.379(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.393(2) . ? C18 C23 1.402(2) . ? C18 P2 1.7970(16) . ? C19 C20 1.392(2) . ? C19 H19 0.9500 . ? C20 C21 1.384(3) . ? C20 H20 0.9500 . ? C21 C22 1.378(3) . ? C21 H21 0.9500 . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 P2 1.7215(12) . ? P1 Pd1 2.2850(4) . ? P2 Pd1 2.2070(4) . ? Cl1 Pd1 2.3507(3) . ? Cl2 Pd1 2.3634(4) . ? 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 C1 N1 111.69(14) . . ? N2 C1 P1 130.54(12) . . ? N1 C1 P1 117.69(10) . . ? C3 C2 N1 105.76(13) . . ? C3 C2 H2 127.1 . . ? N1 C2 H2 127.1 . . ? C2 C3 N2 111.01(14) . . ? C2 C3 H3 124.5 . . ? N2 C3 H3 124.5 . . ? C5 C4 C7 109.57(15) . . ? C5 C4 C6 109.07(16) . . ? C7 C4 C6 109.20(14) . . ? C5 C4 P1 110.81(12) . . ? C7 C4 P1 112.75(12) . . ? C6 C4 P1 105.30(11) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C10 109.25(15) . . ? C9 C8 C11 109.57(14) . . ? C10 C8 C11 109.26(15) . . ? C9 C8 P1 110.57(12) . . ? C10 C8 P1 105.31(11) . . ? C11 C8 P1 112.76(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 119.70(15) . . ? C13 C12 P2 120.35(13) . . ? C17 C12 P2 119.87(12) . . ? C14 C13 C12 120.25(17) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.66(17) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.64(16) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 119.89(18) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 119.85(16) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? C19 C18 C23 120.01(15) . . ? C19 C18 P2 120.92(13) . . ? C23 C18 P2 118.92(13) . . ? C20 C19 C18 119.35(17) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C21 C20 C19 120.27(18) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 120.51(17) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.16(18) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 119.69(18) . . ? C22 C23 H23 120.2 . . ? C18 C23 H23 120.2 . . ? C1 N1 C2 106.48(12) . . ? C1 N1 P2 121.86(10) . . ? C2 N1 P2 131.39(10) . . ? C1 N2 C3 105.07(13) . . ? C1 P1 C4 103.83(7) . . ? C1 P1 C8 103.09(7) . . ? C4 P1 C8 115.78(7) . . ? C1 P1 Pd1 103.66(5) . . ? C4 P1 Pd1 114.29(6) . . ? C8 P1 Pd1 114.04(5) . . ? N1 P2 C18 104.12(7) . . ? N1 P2 C12 102.78(7) . . ? C18 P2 C12 108.35(7) . . ? N1 P2 Pd1 107.26(4) . . ? C18 P2 Pd1 116.62(6) . . ? C12 P2 Pd1 116.07(5) . . ? P2 Pd1 P1 89.042(13) . . ? P2 Pd1 Cl1 173.342(14) . . ? P1 Pd1 Cl1 97.559(14) . . ? P2 Pd1 Cl2 82.287(14) . . ? P1 Pd1 Cl2 171.295(15) . . ? Cl1 Pd1 Cl2 91.124(15) . . ? 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 N1 C2 C3 N2 -0.2(2) . . . . ? C17 C12 C13 C14 1.0(2) . . . . ? P2 C12 C13 C14 177.55(13) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? C14 C15 C16 C17 1.7(3) . . . . ? C15 C16 C17 C12 -0.8(3) . . . . ? C13 C12 C17 C16 -0.6(3) . . . . ? P2 C12 C17 C16 -177.13(14) . . . . ? C23 C18 C19 C20 0.0(3) . . . . ? P2 C18 C19 C20 -175.48(14) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C21 C22 C23 C18 0.5(3) . . . . ? C19 C18 C23 C22 -0.5(2) . . . . ? P2 C18 C23 C22 175.08(13) . . . . ? N2 C1 N1 C2 -0.17(19) . . . . ? P1 C1 N1 C2 176.87(11) . . . . ? N2 C1 N1 P2 174.49(11) . . . . ? P1 C1 N1 P2 -8.48(17) . . . . ? C3 C2 N1 C1 0.22(19) . . . . ? C3 C2 N1 P2 -173.72(13) . . . . ? N1 C1 N2 C3 0.04(18) . . . . ? P1 C1 N2 C3 -176.51(12) . . . . ? C2 C3 N2 C1 0.1(2) . . . . ? N2 C1 P1 C4 -58.71(16) . . . . ? N1 C1 P1 C4 124.91(12) . . . . ? N2 C1 P1 C8 62.43(15) . . . . ? N1 C1 P1 C8 -113.95(12) . . . . ? N2 C1 P1 Pd1 -178.44(14) . . . . ? N1 C1 P1 Pd1 5.19(12) . . . . ? C5 C4 P1 C1 -175.76(14) . . . . ? C7 C4 P1 C1 61.01(13) . . . . ? C6 C4 P1 C1 -57.97(12) . . . . ? C5 C4 P1 C8 72.04(16) . . . . ? C7 C4 P1 C8 -51.19(15) . . . . ? C6 C4 P1 C8 -170.17(11) . . . . ? C5 C4 P1 Pd1 -63.56(15) . . . . ? C7 C4 P1 Pd1 173.21(11) . . . . ? C6 C4 P1 Pd1 54.23(12) . . . . ? C9 C8 P1 C1 -178.92(12) . . . . ? C10 C8 P1 C1 63.19(13) . . . . ? C11 C8 P1 C1 -55.87(13) . . . . ? C9 C8 P1 C4 -66.29(14) . . . . ? C10 C8 P1 C4 175.82(11) . . . . ? C11 C8 P1 C4 56.77(15) . . . . ? C9 C8 P1 Pd1 69.41(12) . . . . ? C10 C8 P1 Pd1 -48.47(13) . . . . ? C11 C8 P1 Pd1 -167.53(10) . . . . ? C1 N1 P2 C18 131.35(13) . . . . ? C2 N1 P2 C18 -55.50(18) . . . . ? C1 N1 P2 C12 -115.70(13) . . . . ? C2 N1 P2 C12 57.46(18) . . . . ? C1 N1 P2 Pd1 7.15(13) . . . . ? C2 N1 P2 Pd1 -179.69(15) . . . . ? C19 C18 P2 N1 79.23(15) . . . . ? C23 C18 P2 N1 -96.29(14) . . . . ? C19 C18 P2 C12 -29.67(16) . . . . ? C23 C18 P2 C12 154.81(12) . . . . ? C19 C18 P2 Pd1 -162.85(12) . . . . ? C23 C18 P2 Pd1 21.63(15) . . . . ? C13 C12 P2 N1 26.68(15) . . . . ? C17 C12 P2 N1 -156.78(13) . . . . ? C13 C12 P2 C18 136.48(13) . . . . ? C17 C12 P2 C18 -46.98(15) . . . . ? C13 C12 P2 Pd1 -90.05(14) . . . . ? C17 C12 P2 Pd1 86.50(13) . . . . ? N1 P2 Pd1 P1 -2.61(5) . . . . ? C18 P2 Pd1 P1 -118.80(6) . . . . ? C12 P2 Pd1 P1 111.60(6) . . . . ? N1 P2 Pd1 Cl2 178.16(5) . . . . ? C18 P2 Pd1 Cl2 61.97(6) . . . . ? C12 P2 Pd1 Cl2 -67.64(6) . . . . ? C1 P1 Pd1 P2 -0.76(5) . . . . ? C4 P1 Pd1 P2 -113.06(6) . . . . ? C8 P1 Pd1 P2 110.56(6) . . . . ? C1 P1 Pd1 Cl1 -179.88(5) . . . . ? C4 P1 Pd1 Cl1 67.81(6) . . . . ? C8 P1 Pd1 Cl1 -68.56(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.413 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 968370' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbpa130919_compl2b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H33 Cl N2 P2 Pd' _chemical_formula_sum 'C24 H33 Cl N2 P2 Pd' _chemical_formula_weight 553.31 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' P P 0.1023 0.0942 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.7612(5) _cell_length_b 36.145(2) _cell_length_c 9.6899(4) _cell_angle_alpha 90.00 _cell_angle_beta 123.139(4) _cell_angle_gamma 90.00 _cell_volume 2569.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6560 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 29.80 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7607 _exptl_absorpt_correction_T_max 0.9268 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29287 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -50 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 30.04 _reflns_number_total 7465 _reflns_number_gt 5580 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick 2013)' _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^ > 2\s(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^)+(0.0287P)^2^+4.3405P] 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 7465 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 C1 C 0.6510(6) 0.83337(10) 0.2614(5) 0.0231(8) Uani 1 1 d . . . C2 C 0.6485(6) 0.85363(11) 0.4760(5) 0.0306(10) Uani 1 1 d . . . H2 H 0.6544 0.8688 0.5588 0.037 Uiso 1 1 calc R . . C3 C 0.6211(8) 0.81673(12) 0.4579(6) 0.0402(12) Uani 1 1 d . . . H3 H 0.6035 0.8016 0.5283 0.048 Uiso 1 1 calc R . . C4 C 0.8657(6) 0.80968(12) 0.1289(6) 0.0302(10) Uani 1 1 d . . . C5 C 0.8787(8) 0.77241(15) 0.2056(8) 0.0613(17) Uani 1 1 d . . . H5A H 0.7736 0.7572 0.1274 0.092 Uiso 1 1 calc R . . H5B H 0.8795 0.7759 0.3063 0.092 Uiso 1 1 calc R . . H5C H 0.9913 0.7600 0.2327 0.092 Uiso 1 1 calc R . . C6 C 1.0309(7) 0.83313(15) 0.2498(8) 0.0551(15) Uani 1 1 d . . . H6A H 1.0272 0.8385 0.3470 0.083 Uiso 1 1 calc R . . H6B H 1.0286 0.8564 0.1965 0.083 Uiso 1 1 calc R . . H6C H 1.1428 0.8195 0.2835 0.083 Uiso 1 1 calc R . . C7 C 0.8663(8) 0.80439(17) -0.0275(7) 0.0586(16) Uani 1 1 d . . . H7A H 0.9834 0.7939 0.0016 0.088 Uiso 1 1 calc R . . H7B H 0.8483 0.8284 -0.0816 0.088 Uiso 1 1 calc R . . H7C H 0.7675 0.7876 -0.1026 0.088 Uiso 1 1 calc R . . C8 C 0.4389(6) 0.81811(11) -0.0896(5) 0.0287(9) Uani 1 1 d . . . C9 C 0.4111(7) 0.82674(16) -0.2555(6) 0.0493(14) Uani 1 1 d . . . H9A H 0.4969 0.8122 -0.2683 0.074 Uiso 1 1 calc R . . H9B H 0.4325 0.8531 -0.2610 0.074 Uiso 1 1 calc R . . H9C H 0.2860 0.8205 -0.3439 0.074 Uiso 1 1 calc R . . C10 C 0.4179(7) 0.77664(13) -0.0732(7) 0.0465(13) Uani 1 1 d . . . H10A H 0.2913 0.7693 -0.1527 0.070 Uiso 1 1 calc R . . H10B H 0.4502 0.7712 0.0388 0.070 Uiso 1 1 calc R . . H10C H 0.4987 0.7628 -0.0952 0.070 Uiso 1 1 calc R . . C11 C 0.2916(7) 0.83896(14) -0.0803(7) 0.0509(14) Uani 1 1 d . . . H11A H 0.3097 0.8657 -0.0819 0.076 Uiso 1 1 calc R . . H11B H 0.3005 0.8323 0.0219 0.076 Uiso 1 1 calc R . . H11C H 0.1708 0.8322 -0.1750 0.076 Uiso 1 1 calc R . . C12 C 0.9117(5) 0.92341(10) 0.4827(5) 0.0199(8) Uani 1 1 d . . . C13 C 0.9160(6) 0.93352(11) 0.6222(5) 0.0284(9) Uani 1 1 d . . . H13 H 0.8066 0.9340 0.6207 0.034 Uiso 1 1 calc R . . C14 C 1.0806(7) 0.94294(13) 0.7646(6) 0.0390(11) Uani 1 1 d . . . H14 H 1.0839 0.9501 0.8606 0.047 Uiso 1 1 calc R . . C15 C 1.2386(7) 0.94199(13) 0.7670(6) 0.0466(14) Uani 1 1 d . . . H15 H 1.3510 0.9483 0.8652 0.056 Uiso 1 1 calc R . . C16 C 1.2361(6) 0.93205(13) 0.6298(7) 0.0438(13) Uani 1 1 d . . . H16 H 1.3464 0.9315 0.6330 0.053 Uiso 1 1 calc R . . C17 C 1.0726(6) 0.92279(11) 0.4855(6) 0.0286(9) Uani 1 1 d . . . H17 H 1.0703 0.9161 0.3896 0.034 Uiso 1 1 calc R . . C18 C 0.5207(5) 0.93505(10) 0.2836(4) 0.0177(7) Uani 1 1 d . . . C19 C 0.5426(6) 0.97283(11) 0.3195(5) 0.0235(8) Uani 1 1 d . . . H19 H 0.6581 0.9841 0.3629 0.028 Uiso 1 1 calc R . . C20 C 0.3967(6) 0.99378(11) 0.2921(5) 0.0281(9) Uani 1 1 d . . . H20 H 0.4124 1.0194 0.3173 0.034 Uiso 1 1 calc R . . C21 C 0.2288(6) 0.97768(12) 0.2285(5) 0.0296(10) Uani 1 1 d . . . H21 H 0.1290 0.9923 0.2096 0.036 Uiso 1 1 calc R . . C22 C 0.2043(6) 0.94030(13) 0.1919(5) 0.0297(10) Uani 1 1 d . . . H22 H 0.0882 0.9293 0.1488 0.036 Uiso 1 1 calc R . . C23 C 0.3490(5) 0.91889(11) 0.2181(5) 0.0247(9) Uani 1 1 d . . . H23 H 0.3319 0.8933 0.1918 0.030 Uiso 1 1 calc R . . C24 C 0.7443(4) 0.96060(9) 0.0939(4) 0.0147(7) Uani 1 1 d . . . H24A H 0.6268 0.9731 0.0476 0.022 Uiso 1 1 calc R . . H24B H 0.7989 0.9681 0.0329 0.022 Uiso 1 1 calc R . . H24C H 0.8258 0.9674 0.2101 0.022 Uiso 1 1 calc R . . N1 N 0.6664(4) 0.86474(8) 0.3488(4) 0.0200(7) Uani 1 1 d . . . N2 N 0.6217(6) 0.80369(9) 0.3240(5) 0.0394(10) Uani 1 1 d . . . P1 P 0.66215(14) 0.83810(3) 0.07971(12) 0.0194(2) Uani 1 1 d . . . P2 P 0.70289(13) 0.90842(2) 0.29765(12) 0.01556(19) Uani 1 1 d . . . Cl1 Cl 0.72441(15) 0.90329(3) -0.15965(12) 0.0319(2) Uani 1 1 d . . . Pd1 Pd 0.70395(4) 0.902478(8) 0.07421(4) 0.01665(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.031(2) 0.0152(18) 0.024(2) 0.0003(15) 0.0162(19) -0.0013(16) C2 0.052(3) 0.024(2) 0.028(2) -0.0001(18) 0.030(2) -0.004(2) C3 0.075(4) 0.025(2) 0.041(3) 0.005(2) 0.045(3) -0.002(2) C4 0.029(2) 0.025(2) 0.037(3) -0.0014(18) 0.019(2) 0.0056(18) C5 0.064(4) 0.035(3) 0.092(5) 0.024(3) 0.047(4) 0.024(3) C6 0.029(3) 0.046(3) 0.071(4) -0.010(3) 0.015(3) 0.007(2) C7 0.070(4) 0.061(4) 0.066(4) 0.002(3) 0.051(4) 0.025(3) C8 0.028(2) 0.025(2) 0.028(2) -0.0078(18) 0.012(2) -0.0067(18) C9 0.050(3) 0.055(3) 0.025(3) -0.012(2) 0.009(2) -0.018(3) C10 0.051(3) 0.029(3) 0.051(3) -0.014(2) 0.023(3) -0.018(2) C11 0.030(3) 0.047(3) 0.065(4) -0.018(3) 0.018(3) -0.005(2) C12 0.0190(19) 0.0160(18) 0.0176(19) -0.0007(15) 0.0054(16) -0.0006(14) C13 0.032(2) 0.026(2) 0.021(2) 0.0005(17) 0.010(2) 0.0010(18) C14 0.045(3) 0.034(3) 0.019(2) -0.0031(19) 0.005(2) 0.003(2) C15 0.032(3) 0.031(3) 0.035(3) -0.004(2) -0.008(2) 0.000(2) C16 0.024(3) 0.032(3) 0.058(4) 0.004(2) 0.011(3) -0.0003(19) C17 0.027(2) 0.023(2) 0.035(2) 0.0016(18) 0.017(2) -0.0019(17) C18 0.0185(19) 0.0218(19) 0.0154(18) -0.0005(14) 0.0109(16) 0.0007(15) C19 0.024(2) 0.022(2) 0.023(2) 0.0001(16) 0.0120(18) 0.0009(16) C20 0.034(2) 0.021(2) 0.031(2) 0.0017(17) 0.019(2) 0.0078(17) C21 0.027(2) 0.035(2) 0.031(2) 0.0021(19) 0.018(2) 0.0103(18) C22 0.018(2) 0.043(3) 0.031(2) 0.000(2) 0.0149(19) -0.0007(18) C23 0.024(2) 0.024(2) 0.028(2) -0.0055(17) 0.0159(19) -0.0070(16) C24 0.0097(17) 0.0136(16) 0.0191(19) -0.0023(14) 0.0068(16) -0.0034(12) N1 0.0266(18) 0.0164(15) 0.0197(16) 0.0001(13) 0.0143(15) -0.0007(13) N2 0.071(3) 0.0165(17) 0.043(2) 0.0005(16) 0.039(2) -0.0027(18) P1 0.0233(5) 0.0168(5) 0.0194(5) -0.0034(4) 0.0126(4) -0.0010(4) P2 0.0184(5) 0.0137(5) 0.0156(5) -0.0010(3) 0.0099(4) -0.0010(3) Cl1 0.0426(6) 0.0374(6) 0.0259(5) -0.0035(5) 0.0252(5) -0.0015(5) Pd1 0.01798(14) 0.01759(13) 0.01610(13) -0.00043(13) 0.01042(11) -0.00043(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.324(5) . ? C1 N1 1.377(5) . ? C1 P1 1.824(4) . ? C2 C3 1.350(6) . ? C2 N1 1.384(5) . ? C2 H2 0.9500 . ? C3 N2 1.384(6) . ? C3 H3 0.9500 . ? C4 C5 1.513(6) . ? C4 C6 1.527(7) . ? C4 C7 1.530(7) . ? C4 P1 1.880(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.520(6) . ? C8 C10 1.529(6) . ? C8 C11 1.539(6) . ? C8 P1 1.879(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.381(5) . ? C12 C17 1.395(6) . ? C12 P2 1.808(4) . ? C13 C14 1.387(6) . ? C13 H13 0.9500 . ? C14 C15 1.372(7) . ? C14 H14 0.9500 . ? C15 C16 1.366(8) . ? C15 H15 0.9500 . ? C16 C17 1.389(7) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.396(5) . ? C18 C23 1.401(5) . ? C18 P2 1.804(4) . ? C19 C20 1.381(5) . ? C19 H19 0.9500 . ? C20 C21 1.375(6) . ? C20 H20 0.9500 . ? C21 C22 1.384(6) . ? C21 H21 0.9500 . ? C22 C23 1.385(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 Pd1 2.121(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N1 P2 1.736(3) . ? P1 Pd1 2.3606(10) . ? P2 Pd1 2.1808(9) . ? Cl1 Pd1 2.3690(10) . ? 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 C1 N1 111.4(3) . . ? N2 C1 P1 130.1(3) . . ? N1 C1 P1 118.5(3) . . ? C3 C2 N1 105.7(4) . . ? C3 C2 H2 127.2 . . ? N1 C2 H2 127.2 . . ? C2 C3 N2 111.5(4) . . ? C2 C3 H3 124.3 . . ? N2 C3 H3 124.3 . . ? C5 C4 C6 109.4(5) . . ? C5 C4 C7 109.6(4) . . ? C6 C4 C7 108.3(4) . . ? C5 C4 P1 114.7(3) . . ? C6 C4 P1 105.1(3) . . ? C7 C4 P1 109.5(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C10 110.6(4) . . ? C9 C8 C11 107.9(4) . . ? C10 C8 C11 108.7(4) . . ? C9 C8 P1 109.4(3) . . ? C10 C8 P1 114.4(3) . . ? C11 C8 P1 105.4(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 119.9(4) . . ? C13 C12 P2 121.4(3) . . ? C17 C12 P2 118.6(3) . . ? C12 C13 C14 119.7(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.1(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 119.4(4) . . ? C16 C17 H17 120.3 . . ? C12 C17 H17 120.3 . . ? C19 C18 C23 119.2(3) . . ? C19 C18 P2 120.5(3) . . ? C23 C18 P2 119.9(3) . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C23 120.0(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C18 119.9(4) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? Pd1 C24 H24A 109.5 . . ? Pd1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? Pd1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C1 N1 C2 106.7(3) . . ? C1 N1 P2 123.0(3) . . ? C2 N1 P2 130.3(3) . . ? C1 N2 C3 104.7(3) . . ? C1 P1 C8 103.13(19) . . ? C1 P1 C4 104.37(19) . . ? C8 P1 C4 113.68(19) . . ? C1 P1 Pd1 101.84(12) . . ? C8 P1 Pd1 117.37(14) . . ? C4 P1 Pd1 114.01(14) . . ? N1 P2 C18 102.32(16) . . ? N1 P2 C12 103.54(17) . . ? C18 P2 C12 106.79(17) . . ? N1 P2 Pd1 107.18(11) . . ? C18 P2 Pd1 117.46(12) . . ? C12 P2 Pd1 117.56(13) . . ? C24 Pd1 P2 84.51(10) . . ? C24 Pd1 P1 173.89(10) . . ? P2 Pd1 P1 89.41(3) . . ? C24 Pd1 Cl1 88.72(10) . . ? P2 Pd1 Cl1 172.78(4) . . ? P1 Pd1 Cl1 97.33(4) . . ? 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 N1 C2 C3 N2 0.4(6) . . . . ? C17 C12 C13 C14 -0.1(6) . . . . ? P2 C12 C13 C14 176.5(3) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C16 0.4(7) . . . . ? C14 C15 C16 C17 0.1(7) . . . . ? C15 C16 C17 C12 -0.6(7) . . . . ? C13 C12 C17 C16 0.6(6) . . . . ? P2 C12 C17 C16 -176.1(3) . . . . ? C23 C18 C19 C20 0.6(6) . . . . ? P2 C18 C19 C20 173.3(3) . . . . ? C18 C19 C20 C21 -0.3(6) . . . . ? C19 C20 C21 C22 0.3(6) . . . . ? C20 C21 C22 C23 -0.5(6) . . . . ? C21 C22 C23 C18 0.8(6) . . . . ? C19 C18 C23 C22 -0.8(6) . . . . ? P2 C18 C23 C22 -173.5(3) . . . . ? N2 C1 N1 C2 1.1(5) . . . . ? P1 C1 N1 C2 178.4(3) . . . . ? N2 C1 N1 P2 -179.4(3) . . . . ? P1 C1 N1 P2 -2.0(5) . . . . ? C3 C2 N1 C1 -0.8(5) . . . . ? C3 C2 N1 P2 179.6(3) . . . . ? N1 C1 N2 C3 -0.8(5) . . . . ? P1 C1 N2 C3 -177.8(4) . . . . ? C2 C3 N2 C1 0.3(6) . . . . ? N2 C1 P1 C8 55.0(5) . . . . ? N1 C1 P1 C8 -121.8(3) . . . . ? N2 C1 P1 C4 -64.1(5) . . . . ? N1 C1 P1 C4 119.2(3) . . . . ? N2 C1 P1 Pd1 177.1(4) . . . . ? N1 C1 P1 Pd1 0.3(3) . . . . ? C9 C8 P1 C1 169.1(3) . . . . ? C10 C8 P1 C1 -66.1(4) . . . . ? C11 C8 P1 C1 53.3(4) . . . . ? C9 C8 P1 C4 -78.5(4) . . . . ? C10 C8 P1 C4 46.3(4) . . . . ? C11 C8 P1 C4 165.7(3) . . . . ? C9 C8 P1 Pd1 58.1(4) . . . . ? C10 C8 P1 Pd1 -177.1(3) . . . . ? C11 C8 P1 Pd1 -57.6(4) . . . . ? C5 C4 P1 C1 44.1(4) . . . . ? C6 C4 P1 C1 -76.1(4) . . . . ? C7 C4 P1 C1 167.7(3) . . . . ? C5 C4 P1 C8 -67.5(4) . . . . ? C6 C4 P1 C8 172.3(3) . . . . ? C7 C4 P1 C8 56.1(4) . . . . ? C5 C4 P1 Pd1 154.4(4) . . . . ? C6 C4 P1 Pd1 34.2(4) . . . . ? C7 C4 P1 Pd1 -82.0(4) . . . . ? C1 N1 P2 C18 126.9(3) . . . . ? C2 N1 P2 C18 -53.7(4) . . . . ? C1 N1 P2 C12 -122.2(3) . . . . ? C2 N1 P2 C12 57.2(4) . . . . ? C1 N1 P2 Pd1 2.7(3) . . . . ? C2 N1 P2 Pd1 -177.9(4) . . . . ? C19 C18 P2 N1 150.3(3) . . . . ? C23 C18 P2 N1 -37.0(3) . . . . ? C19 C18 P2 C12 41.9(4) . . . . ? C23 C18 P2 C12 -145.5(3) . . . . ? C19 C18 P2 Pd1 -92.6(3) . . . . ? C23 C18 P2 Pd1 80.0(3) . . . . ? C13 C12 P2 N1 -72.4(3) . . . . ? C17 C12 P2 N1 104.2(3) . . . . ? C13 C12 P2 C18 35.1(4) . . . . ? C17 C12 P2 C18 -148.2(3) . . . . ? C13 C12 P2 Pd1 169.6(3) . . . . ? C17 C12 P2 Pd1 -13.7(4) . . . . ? N1 P2 Pd1 C24 178.84(15) . . . . ? C18 P2 Pd1 C24 64.49(17) . . . . ? C12 P2 Pd1 C24 -65.20(16) . . . . ? N1 P2 Pd1 P1 -1.77(12) . . . . ? C18 P2 Pd1 P1 -116.12(14) . . . . ? C12 P2 Pd1 P1 114.19(14) . . . . ? C1 P1 Pd1 P2 0.95(14) . . . . ? C8 P1 Pd1 P2 112.66(16) . . . . ? C4 P1 Pd1 P2 -110.82(16) . . . . ? C1 P1 Pd1 Cl1 178.35(14) . . . . ? C8 P1 Pd1 Cl1 -69.93(16) . . . . ? C4 P1 Pd1 Cl1 66.58(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.102 _refine_diff_density_min -2.037 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 968371' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pbpa130828_compl2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H33 Cl N2 P2 Pd' _chemical_formula_sum 'C24 H33 Cl N2 P2 Pd' _chemical_formula_weight 553.31 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' P P 0.1023 0.0942 '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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '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' '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' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-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' '-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' _cell_length_a 25.9649(6) _cell_length_b 25.9649(6) _cell_length_c 20.5993(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 12027.0(6) _cell_formula_units_Z 18 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13360 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5112 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76154 _exptl_absorpt_correction_T_max 0.94752 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24630 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6126 _reflns_number_gt 3968 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0717P)^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 6126 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.004 _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 C1 C 0.74152(19) 0.96364(18) 0.2796(2) 0.0319(10) Uani 1 1 d . . . C2 C 0.6701(2) 0.8939(2) 0.2255(3) 0.0488(13) Uani 1 1 d . . . H2 H 0.6466 0.8576 0.2028 0.059 Uiso 1 1 calc R . . C3 C 0.6553(2) 0.9366(2) 0.2340(2) 0.0451(12) Uani 1 1 d . . . H3 H 0.6201 0.9355 0.2192 0.054 Uiso 1 1 calc R . . C4 C 0.7942(2) 0.9695(2) 0.4050(2) 0.0438(12) Uani 1 1 d . . . C5 C 0.7305(3) 0.9510(3) 0.4259(2) 0.0596(15) Uani 1 1 d . . . H5A H 0.7225 0.9319 0.4687 0.089 Uiso 1 1 calc R . . H5B H 0.7023 0.9230 0.3942 0.089 Uiso 1 1 calc R . . H5C H 0.7261 0.9862 0.4283 0.089 Uiso 1 1 calc R . . C6 C 0.7989(2) 0.9126(2) 0.3982(3) 0.0580(15) Uani 1 1 d . . . H6A H 0.7864 0.8900 0.4388 0.087 Uiso 1 1 calc R . . H6B H 0.8402 0.9237 0.3887 0.087 Uiso 1 1 calc R . . H6C H 0.7732 0.8881 0.3627 0.087 Uiso 1 1 calc R . . C7 C 0.8374(3) 1.0107(3) 0.4564(3) 0.078(2) Uani 1 1 d . . . H7A H 0.8319 1.0452 0.4621 0.118 Uiso 1 1 calc R . . H7B H 0.8783 1.0243 0.4424 0.118 Uiso 1 1 calc R . . H7C H 0.8297 0.9893 0.4976 0.118 Uiso 1 1 calc R . . C8 C 0.8704(2) 1.0200(2) 0.2766(2) 0.0430(12) Uani 1 1 d . . . C9 C 0.8666(2) 0.9607(2) 0.2574(3) 0.0571(14) Uani 1 1 d . . . H9A H 0.8964 0.9681 0.2240 0.086 Uiso 1 1 calc R . . H9B H 0.8269 0.9333 0.2404 0.086 Uiso 1 1 calc R . . H9C H 0.8743 0.9431 0.2957 0.086 Uiso 1 1 calc R . . C10 C 0.9289(2) 1.0593(3) 0.3132(3) 0.0638(16) Uani 1 1 d . . . H10A H 0.9314 1.0376 0.3508 0.096 Uiso 1 1 calc R . . H10B H 0.9299 1.0957 0.3280 0.096 Uiso 1 1 calc R . . H10C H 0.9626 1.0698 0.2842 0.096 Uiso 1 1 calc R . . C11 C 0.8672(2) 1.0506(2) 0.2146(3) 0.0546(14) Uani 1 1 d . . . H11A H 0.8674 1.0873 0.2259 0.082 Uiso 1 1 calc R . . H11B H 0.8306 1.0240 0.1910 0.082 Uiso 1 1 calc R . . H11C H 0.9017 1.0601 0.1872 0.082 Uiso 1 1 calc R . . C12 C 0.6492(2) 1.0332(2) 0.3425(2) 0.0473(13) Uani 1 1 d . . . H12A H 0.6124 1.0041 0.3208 0.071 Uiso 1 1 calc R . . H12B H 0.6475 1.0694 0.3515 0.071 Uiso 1 1 calc R . . H12C H 0.6536 1.0165 0.3834 0.071 Uiso 1 1 calc R . . C13 C 0.69812(18) 1.07742(17) 0.2148(2) 0.0311(10) Uani 1 1 d . . . C14 C 0.7432(2) 1.10247(19) 0.1694(2) 0.0357(10) Uani 1 1 d . . . H14 H 0.7809 1.1069 0.1791 0.043 Uiso 1 1 calc R . . C15 C 0.7341(2) 1.12115(19) 0.1102(2) 0.0392(11) Uani 1 1 d . . . H15 H 0.7654 1.1387 0.0794 0.047 Uiso 1 1 calc R . . C16 C 0.6781(2) 1.1140(2) 0.0959(3) 0.0462(13) Uani 1 1 d . . . H16 H 0.6713 1.1263 0.0550 0.055 Uiso 1 1 calc R . . C17 C 0.6337(2) 1.0896(2) 0.1404(3) 0.0477(13) Uani 1 1 d . . . H17 H 0.5960 1.0852 0.1305 0.057 Uiso 1 1 calc R . . C18 C 0.6430(2) 1.0711(2) 0.2004(2) 0.0439(12) Uani 1 1 d . . . H18 H 0.6117 1.0541 0.2314 0.053 Uiso 1 1 calc R . . C19 C 0.78140(17) 1.16885(18) 0.3435(2) 0.0275(9) Uani 1 1 d . . . C20 C 0.7936(2) 1.2079(2) 0.2931(2) 0.0423(12) Uani 1 1 d . . . H20 H 0.8050 1.2004 0.2519 0.051 Uiso 1 1 calc R . . C21 C 0.7891(2) 1.2588(2) 0.3025(3) 0.0585(15) Uani 1 1 d . . . H21 H 0.7980 1.2862 0.2679 0.070 Uiso 1 1 calc R . . C22 C 0.7715(3) 1.2694(2) 0.3629(3) 0.0610(15) Uani 1 1 d . . . H22 H 0.7694 1.3044 0.3701 0.073 Uiso 1 1 calc R . . C23 C 0.7573(2) 1.2285(2) 0.4114(3) 0.0558(14) Uani 1 1 d . . . H23 H 0.7441 1.2347 0.4522 0.067 Uiso 1 1 calc R . . C24 C 0.7620(2) 1.1780(2) 0.4019(2) 0.0473(12) Uani 1 1 d . . . H24 H 0.7518 1.1498 0.4359 0.057 Uiso 1 1 calc R . . N1 N 0.72385(17) 0.91052(16) 0.25434(19) 0.0417(10) Uani 1 1 d . . . N2 N 0.70111(15) 0.98214(15) 0.26810(18) 0.0339(9) Uani 1 1 d . . . P1 P 0.80705(5) 1.01214(5) 0.32746(6) 0.0313(3) Uani 1 1 d . . . P2 P 0.71179(5) 1.05095(5) 0.29058(6) 0.0308(3) Uani 1 1 d . . . Cl1 Cl 0.88880(5) 1.15925(5) 0.39564(6) 0.0417(3) Uani 1 1 d . . . Pd1 Pd 0.799001(14) 1.098793(14) 0.337674(16) 0.02877(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(2) 0.025(2) 0.026(2) 0.0039(19) 0.0001(19) 0.0080(19) C2 0.050(3) 0.031(3) 0.053(3) -0.003(2) -0.011(3) 0.011(2) C3 0.040(3) 0.032(3) 0.054(3) -0.002(2) -0.014(2) 0.012(2) C4 0.049(3) 0.037(3) 0.036(3) 0.008(2) -0.005(2) 0.014(2) C5 0.076(4) 0.073(4) 0.037(3) 0.019(3) 0.013(3) 0.042(3) C6 0.071(4) 0.050(3) 0.059(4) 0.020(3) 0.004(3) 0.034(3) C7 0.106(5) 0.054(4) 0.042(3) 0.006(3) -0.028(3) 0.015(4) C8 0.044(3) 0.042(3) 0.049(3) -0.004(2) 0.005(2) 0.025(2) C9 0.065(4) 0.061(3) 0.061(4) -0.002(3) 0.006(3) 0.043(3) C10 0.031(3) 0.073(4) 0.083(4) -0.014(3) 0.001(3) 0.023(3) C11 0.054(3) 0.056(3) 0.057(3) 0.015(3) 0.026(3) 0.030(3) C12 0.035(3) 0.056(3) 0.041(3) 0.005(2) 0.010(2) 0.016(2) C13 0.030(2) 0.024(2) 0.033(2) -0.0028(19) 0.000(2) 0.0091(18) C14 0.035(2) 0.032(2) 0.036(3) -0.004(2) -0.005(2) 0.014(2) C15 0.051(3) 0.030(2) 0.032(2) 0.002(2) 0.006(2) 0.016(2) C16 0.063(3) 0.037(3) 0.044(3) 0.001(2) -0.009(3) 0.029(3) C17 0.044(3) 0.047(3) 0.057(3) 0.004(3) -0.007(3) 0.026(2) C18 0.038(3) 0.047(3) 0.050(3) 0.011(2) 0.005(2) 0.024(2) C19 0.024(2) 0.030(2) 0.027(2) -0.0010(19) 0.0002(18) 0.0125(18) C20 0.042(3) 0.034(3) 0.048(3) 0.000(2) 0.001(2) 0.017(2) C21 0.065(4) 0.036(3) 0.069(4) 0.002(3) -0.011(3) 0.020(3) C22 0.071(4) 0.044(3) 0.072(4) -0.016(3) -0.011(3) 0.032(3) C23 0.067(4) 0.056(3) 0.046(3) -0.016(3) -0.003(3) 0.032(3) C24 0.053(3) 0.048(3) 0.041(3) 0.000(2) 0.003(2) 0.026(3) N1 0.043(2) 0.032(2) 0.044(2) -0.0051(19) -0.0029(19) 0.0145(18) N2 0.0299(19) 0.0280(19) 0.037(2) 0.0026(17) -0.0060(17) 0.0096(16) P1 0.0330(6) 0.0277(6) 0.0308(6) 0.0007(5) -0.0014(5) 0.0133(5) P2 0.0267(6) 0.0300(6) 0.0318(6) 0.0022(5) 0.0031(5) 0.0113(5) Cl1 0.0409(6) 0.0358(6) 0.0393(7) -0.0035(5) -0.0102(5) 0.0123(5) Pd1 0.0294(2) 0.0273(2) 0.0258(2) 0.00026(14) 0.00095(14) 0.01127(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.323(5) . ? C1 N2 1.375(5) . ? C1 P1 1.820(4) . ? C2 C3 1.355(7) . ? C2 N1 1.373(6) . ? C2 H2 0.9500 . ? C3 N2 1.378(6) . ? C3 H3 0.9500 . ? C4 C7 1.524(7) . ? C4 C5 1.534(7) . ? C4 C6 1.550(7) . ? C4 P1 1.876(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.527(7) . ? C8 C10 1.540(7) . ? C8 C9 1.545(6) . ? C8 P1 1.874(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 P2 1.802(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.381(6) . ? C13 C18 1.389(6) . ? C13 P2 1.810(4) . ? C14 C15 1.375(6) . ? C14 H14 0.9500 . ? C15 C16 1.400(7) . ? C15 H15 0.9500 . ? C16 C17 1.357(7) . ? C16 H16 0.9500 . ? C17 C18 1.390(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.370(6) . ? C19 C20 1.374(6) . ? C19 Pd1 2.089(4) . ? C20 C21 1.394(7) . ? C20 H20 0.9500 . ? C21 C22 1.400(8) . ? C21 H21 0.9500 . ? C22 C23 1.368(8) . ? C22 H22 0.9500 . ? C23 C24 1.391(7) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? N2 P2 1.729(4) . ? P1 Pd1 2.3707(11) . ? P2 Pd1 2.1907(11) . ? Cl1 Pd1 2.3804(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 111.7(4) . . ? N1 C1 P1 130.6(4) . . ? N2 C1 P1 117.7(3) . . ? C3 C2 N1 110.2(4) . . ? C3 C2 H2 124.9 . . ? N1 C2 H2 124.9 . . ? C2 C3 N2 107.0(4) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? C7 C4 C5 109.0(5) . . ? C7 C4 C6 110.6(4) . . ? C5 C4 C6 108.3(4) . . ? C7 C4 P1 109.0(3) . . ? C5 C4 P1 105.7(3) . . ? C6 C4 P1 114.2(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C10 110.9(4) . . ? C11 C8 C9 108.2(4) . . ? C10 C8 C9 109.7(4) . . ? C11 C8 P1 104.6(3) . . ? C10 C8 P1 108.6(3) . . ? C9 C8 P1 114.9(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P2 C12 H12A 109.5 . . ? P2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? P2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.4(4) . . ? C14 C13 P2 118.8(3) . . ? C18 C13 P2 121.7(3) . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.3(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.5(5) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 119.8(4) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C24 C19 C20 120.3(4) . . ? C24 C19 Pd1 117.4(3) . . ? C20 C19 Pd1 122.0(3) . . ? C19 C20 C21 119.8(5) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 120.0(5) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 118.9(5) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 120.8(5) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C19 C24 C23 120.0(5) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C1 N1 C2 105.4(4) . . ? C1 N2 C3 105.6(4) . . ? C1 N2 P2 124.0(3) . . ? C3 N2 P2 130.3(3) . . ? C1 P1 C8 103.8(2) . . ? C1 P1 C4 103.0(2) . . ? C8 P1 C4 115.4(2) . . ? C1 P1 Pd1 102.08(15) . . ? C8 P1 Pd1 115.83(15) . . ? C4 P1 Pd1 114.20(17) . . ? N2 P2 C12 103.7(2) . . ? N2 P2 C13 101.59(18) . . ? C12 P2 C13 106.6(2) . . ? N2 P2 Pd1 106.91(13) . . ? C12 P2 Pd1 115.25(17) . . ? C13 P2 Pd1 120.65(14) . . ? C19 Pd1 P2 84.54(11) . . ? C19 Pd1 P1 173.23(11) . . ? P2 Pd1 P1 88.81(4) . . ? C19 Pd1 Cl1 88.03(11) . . ? P2 Pd1 Cl1 171.90(4) . . ? P1 Pd1 Cl1 98.53(4) . . ? 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 N1 C2 C3 N2 1.0(6) . . . . ? C18 C13 C14 C15 0.0(6) . . . . ? P2 C13 C14 C15 177.6(3) . . . . ? C13 C14 C15 C16 -0.6(7) . . . . ? C14 C15 C16 C17 0.8(7) . . . . ? C15 C16 C17 C18 -0.4(7) . . . . ? C14 C13 C18 C17 0.4(7) . . . . ? P2 C13 C18 C17 -177.1(4) . . . . ? C16 C17 C18 C13 -0.2(7) . . . . ? C24 C19 C20 C21 3.3(7) . . . . ? Pd1 C19 C20 C21 -170.8(4) . . . . ? C19 C20 C21 C22 -0.9(8) . . . . ? C20 C21 C22 C23 -1.7(8) . . . . ? C21 C22 C23 C24 2.0(9) . . . . ? C20 C19 C24 C23 -3.1(7) . . . . ? Pd1 C19 C24 C23 171.3(4) . . . . ? C22 C23 C24 C19 0.4(8) . . . . ? N2 C1 N1 C2 0.0(5) . . . . ? P1 C1 N1 C2 177.5(4) . . . . ? C3 C2 N1 C1 -0.6(6) . . . . ? N1 C1 N2 C3 0.6(5) . . . . ? P1 C1 N2 C3 -177.3(3) . . . . ? N1 C1 N2 P2 -176.6(3) . . . . ? P1 C1 N2 P2 5.5(5) . . . . ? C2 C3 N2 C1 -0.9(5) . . . . ? C2 C3 N2 P2 176.0(4) . . . . ? N1 C1 P1 C8 54.0(5) . . . . ? N2 C1 P1 C8 -128.6(3) . . . . ? N1 C1 P1 C4 -66.7(5) . . . . ? N2 C1 P1 C4 110.8(3) . . . . ? N1 C1 P1 Pd1 174.7(4) . . . . ? N2 C1 P1 Pd1 -7.9(3) . . . . ? C11 C8 P1 C1 63.0(4) . . . . ? C10 C8 P1 C1 -178.6(3) . . . . ? C9 C8 P1 C1 -55.5(4) . . . . ? C11 C8 P1 C4 174.8(3) . . . . ? C10 C8 P1 C4 -66.8(4) . . . . ? C9 C8 P1 C4 56.3(4) . . . . ? C11 C8 P1 Pd1 -48.0(4) . . . . ? C10 C8 P1 Pd1 70.4(4) . . . . ? C9 C8 P1 Pd1 -166.5(3) . . . . ? C7 C4 P1 C1 -166.1(4) . . . . ? C5 C4 P1 C1 -49.2(4) . . . . ? C6 C4 P1 C1 69.7(4) . . . . ? C7 C4 P1 C8 81.6(5) . . . . ? C5 C4 P1 C8 -161.5(3) . . . . ? C6 C4 P1 C8 -42.6(4) . . . . ? C7 C4 P1 Pd1 -56.3(4) . . . . ? C5 C4 P1 Pd1 60.6(4) . . . . ? C6 C4 P1 Pd1 179.5(3) . . . . ? C1 N2 P2 C12 -121.8(4) . . . . ? C3 N2 P2 C12 61.8(5) . . . . ? C1 N2 P2 C13 127.7(4) . . . . ? C3 N2 P2 C13 -48.7(4) . . . . ? C1 N2 P2 Pd1 0.4(4) . . . . ? C3 N2 P2 Pd1 -176.0(4) . . . . ? C14 C13 P2 N2 -81.2(4) . . . . ? C18 C13 P2 N2 96.3(4) . . . . ? C14 C13 P2 C12 170.6(3) . . . . ? C18 C13 P2 C12 -11.9(4) . . . . ? C14 C13 P2 Pd1 36.6(4) . . . . ? C18 C13 P2 Pd1 -145.9(3) . . . . ? C24 C19 Pd1 P2 100.8(3) . . . . ? C20 C19 Pd1 P2 -84.9(3) . . . . ? C24 C19 Pd1 Cl1 -75.9(3) . . . . ? C20 C19 Pd1 Cl1 98.3(3) . . . . ? N2 P2 Pd1 C19 177.06(18) . . . . ? C12 P2 Pd1 C19 -68.3(2) . . . . ? C13 P2 Pd1 C19 62.0(2) . . . . ? N2 P2 Pd1 P1 -4.24(14) . . . . ? C12 P2 Pd1 P1 110.4(2) . . . . ? C13 P2 Pd1 P1 -119.33(17) . . . . ? C1 P1 Pd1 P2 6.23(14) . . . . ? C8 P1 Pd1 P2 118.18(18) . . . . ? C4 P1 Pd1 P2 -104.11(17) . . . . ? C1 P1 Pd1 Cl1 -177.22(14) . . . . ? C8 P1 Pd1 Cl1 -65.26(18) . . . . ? C4 P1 Pd1 Cl1 72.45(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.769 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.149 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.032 335.1 158.3 2 0.333 0.667 -0.107 327.1 156.1 3 0.667 0.333 0.092 327.0 156.1 _platon_squeeze_details ; The residual electron density was assigned to half a molecule of the pentane solvent [471/18 = 26 e per asymmetric unit; half a molecule of C5H12 would give 21 e]. ; #==END _database_code_depnum_ccdc_archive 'CCDC 968372'