data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'F Cloke' _publ_contact_author_email F.G.CLOKE@SUSSEX.AC.UK _publ_section_title ; Synthetic and Structural Studies on Amine Coordination to Pd-N-Heterocyclic Carbene Complexes ; _publ_requested_category FM loop_ _publ_author_name 'F Cloke' 'S Caddick' 'Alexandra K. deLewis' 'Oriana Esposito' 'Peter B Hitchcock' #===END # Attachment 'may2906.cif' data_may2906 _database_code_depnum_ccdc_archive 'CCDC 659623' _audit_creation_date 2006-05-30T08:47:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H36 Cl N3 O3 Pd' _chemical_formula_sum 'C23 H36 Cl N3 O3 Pd' _chemical_formula_weight 544.4 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.4010(16) _cell_length_b 13.4541(10) _cell_length_c 14.9057(18) _cell_angle_alpha 90 _cell_angle_beta 111.894(4) _cell_angle_gamma 90 _cell_volume 2493.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19407 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 22.722 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.45 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_special_details ; The product crystallised as conglomerates of small very thin crystals. After several attempts a piece was separated that, although not completely single, gave an indexable diffraction pattern. The diffraction was very weak and limited in extent. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.8672 _exptl_absorpt_correction_T_max 0.996 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.732254E-1 _diffrn_orient_matrix_ub_12 0.126361E-1 _diffrn_orient_matrix_ub_13 0.498346E-1 _diffrn_orient_matrix_ub_21 0.28661E-2 _diffrn_orient_matrix_ub_22 -0.698995E-1 _diffrn_orient_matrix_ub_23 0.236435E-1 _diffrn_orient_matrix_ub_31 0.331283E-1 _diffrn_orient_matrix_ub_32 -0.218829E-1 _diffrn_orient_matrix_ub_33 -0.467468E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.1049 _diffrn_reflns_av_unetI/netI 0.091 _diffrn_reflns_number 9369 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 22.93 _diffrn_reflns_theta_full 22.93 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _reflns_number_total 3310 _reflns_number_gt 2435 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1042P)^2^+45.2193P] 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_number_reflns 3310 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.2369 _refine_ls_wR_factor_gt 0.2113 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.945 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.154 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd 0.19710(7) 0.08450(7) 0.86599(7) 0.0321(4) Uani 1 1 d . . . Cl Cl 0.2281(3) -0.0580(2) 0.9745(2) 0.0415(9) Uani 1 1 d . . . O1 O 0.1149(8) 0.1934(8) 1.1423(7) 0.055(3) Uani 1 1 d . . . O2 O 0.1109(7) 0.4483(7) 0.5023(7) 0.043(2) Uani 1 1 d . . . O3 O 0.1827(7) 0.5407(7) 0.6358(7) 0.045(2) Uani 1 1 d . . . N1 N 0.2959(8) -0.0147(8) 0.7351(8) 0.035(3) Uani 1 1 d . . . N2 N 0.1297(8) -0.0559(8) 0.6969(8) 0.037(3) Uani 1 1 d . . . N3 N 0.1662(8) 0.1761(8) 0.9709(8) 0.036(3) Uani 1 1 d . . . H3 H 0.1622 0.2418 0.9504 0.043 Uiso 1 1 calc R . . C1 C 0.2098(10) -0.0009(8) 0.7628(9) 0.033(3) Uani 1 1 d . . . C2 C 0.2690(10) -0.0734(9) 0.6543(10) 0.039(3) Uani 1 1 d . . . H2 H 0.3148 -0.0919 0.6215 0.047 Uiso 1 1 calc R . . C3 C 0.1646(10) -0.1001(9) 0.6300(10) 0.035(3) Uani 1 1 d . . . H3A H 0.1234 -0.141 0.5773 0.042 Uiso 1 1 calc R . . C4 C 0.4065(9) 0.0315(10) 0.7788(9) 0.033(3) Uani 1 1 d . . . C5 C 0.4890(11) -0.0464(11) 0.7742(14) 0.061(5) Uani 1 1 d . . . H5A H 0.486 -0.1048 0.8125 0.092 Uiso 1 1 calc R . . H5B H 0.5614 -0.0176 0.8004 0.092 Uiso 1 1 calc R . . H5C H 0.472 -0.0662 0.7069 0.092 Uiso 1 1 calc R . . C6 C 0.4340(10) 0.0580(13) 0.8842(11) 0.055(4) Uani 1 1 d . . . H6A H 0.4294 -0.0016 0.9202 0.082 Uiso 1 1 calc R . . H6B H 0.3832 0.1081 0.8892 0.082 Uiso 1 1 calc R . . H6C H 0.5072 0.0849 0.9113 0.082 Uiso 1 1 calc R . . C7 C 0.4126(11) 0.1212(11) 0.7198(11) 0.053(4) Uani 1 1 d . . . H7A H 0.3945 0.1013 0.6523 0.079 Uiso 1 1 calc R . . H7B H 0.4856 0.1485 0.7456 0.079 Uiso 1 1 calc R . . H7C H 0.3615 0.1718 0.7232 0.079 Uiso 1 1 calc R . . C8 C 0.0148(10) -0.0746(9) 0.6886(9) 0.034(3) Uani 1 1 d . . . C9 C -0.0575(11) -0.0505(13) 0.5875(11) 0.056(4) Uani 1 1 d . . . H9A H -0.0369 -0.0904 0.5422 0.084 Uiso 1 1 calc R . . H9B H -0.0511 0.0202 0.575 0.084 Uiso 1 1 calc R . . H9C H -0.1321 -0.0656 0.579 0.084 Uiso 1 1 calc R . . C10 C -0.0188(10) -0.0120(10) 0.7569(10) 0.043(3) Uani 1 1 d . . . H10A H 0.0277 -0.0271 0.8238 0.064 Uiso 1 1 calc R . . H10B H -0.0936 -0.0269 0.7474 0.064 Uiso 1 1 calc R . . H10C H -0.0122 0.0586 0.7438 0.064 Uiso 1 1 calc R . . C11 C 0.0077(12) -0.1846(10) 0.7101(12) 0.054(4) Uani 1 1 d . . . H11A H 0.0553 -0.1986 0.7769 0.081 Uiso 1 1 calc R . . H11B H 0.0298 -0.2246 0.6657 0.081 Uiso 1 1 calc R . . H11C H -0.0665 -0.2012 0.7014 0.081 Uiso 1 1 calc R . . C12 C 0.2468(12) 0.1704(9) 1.0691(9) 0.043(3) Uani 1 1 d . . . H12A H 0.3156 0.1974 1.0693 0.051 Uiso 1 1 calc R . . H12B H 0.2587 0.0997 1.0886 0.051 Uiso 1 1 calc R . . C13 C 0.2153(12) 0.2267(12) 1.1430(10) 0.051(4) Uani 1 1 d . . . H13A H 0.2712 0.2169 1.2082 0.062 Uiso 1 1 calc R . . H13B H 0.2111 0.2986 1.1281 0.062 Uiso 1 1 calc R . . C14 C 0.0363(13) 0.2069(12) 1.0504(11) 0.052(4) Uani 1 1 d . . . H14A H 0.0315 0.2784 1.0336 0.062 Uiso 1 1 calc R . . H14B H -0.0343 0.1858 1.0509 0.062 Uiso 1 1 calc R . . C15 C 0.0603(11) 0.1486(11) 0.9746(11) 0.049(4) Uani 1 1 d . . . H15A H 0.0601 0.0768 0.9888 0.059 Uiso 1 1 calc R . . H15B H 0.0031 0.161 0.9106 0.059 Uiso 1 1 calc R . . C16 C 0.1791(9) 0.2005(9) 0.7755(9) 0.031(3) Uani 1 1 d . . . C17 C 0.2282(10) 0.2917(9) 0.8153(10) 0.038(3) Uani 1 1 d . . . H17 H 0.2678 0.2973 0.8829 0.045 Uiso 1 1 calc R . . C18 C 0.2182(10) 0.3745(10) 0.7544(11) 0.041(3) Uani 1 1 d . . . H18 H 0.2502 0.4358 0.782 0.05 Uiso 1 1 calc R . . C19 C 0.1627(11) 0.3684(10) 0.6556(10) 0.039(3) Uani 1 1 d . . . C20 C 0.1162(10) 0.2783(10) 0.6172(10) 0.038(3) Uani 1 1 d . . . H20 H 0.0785 0.2718 0.5495 0.046 Uiso 1 1 calc R . . C21 C 0.1245(10) 0.1977(9) 0.6774(11) 0.040(3) Uani 1 1 d . . . H21 H 0.0906 0.1373 0.6491 0.048 Uiso 1 1 calc R . . C22 C 0.1480(10) 0.4539(10) 0.5892(10) 0.035(3) Uani 1 1 d . . . C23 C 0.1629(12) 0.6271(10) 0.5753(12) 0.051(4) Uani 1 1 d . . . H23A H 0.1895 0.6155 0.5231 0.076 Uiso 1 1 calc R . . H23B H 0.2003 0.6844 0.6139 0.076 Uiso 1 1 calc R . . H23C H 0.0855 0.6405 0.5474 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd 0.0319(6) 0.0266(6) 0.0418(7) 0.0006(5) 0.0184(4) -0.0001(4) Cl 0.0482(19) 0.0291(17) 0.053(2) 0.0072(14) 0.0253(17) 0.0014(14) O1 0.069(7) 0.059(7) 0.054(7) -0.002(5) 0.042(6) -0.021(5) O2 0.050(6) 0.043(6) 0.041(6) 0.005(4) 0.025(5) 0.003(4) O3 0.048(6) 0.033(5) 0.053(6) 0.005(5) 0.018(5) 0.003(4) N1 0.027(6) 0.037(6) 0.045(7) 0.004(5) 0.018(5) 0.003(5) N2 0.030(6) 0.033(6) 0.050(7) 0.001(5) 0.018(5) 0.000(5) N3 0.040(6) 0.032(6) 0.041(7) 0.004(5) 0.021(5) -0.002(5) C1 0.034(7) 0.007(6) 0.055(9) -0.003(6) 0.013(6) 0.004(5) C2 0.042(8) 0.031(7) 0.053(9) -0.003(7) 0.029(7) 0.004(6) C3 0.036(7) 0.031(7) 0.044(8) -0.003(6) 0.022(6) 0.001(6) C4 0.025(6) 0.042(8) 0.033(8) 0.006(6) 0.013(6) -0.001(6) C5 0.035(8) 0.041(9) 0.112(15) -0.006(9) 0.033(9) 0.002(7) C6 0.019(7) 0.083(12) 0.062(10) -0.006(8) 0.016(7) -0.007(7) C7 0.039(8) 0.057(10) 0.066(10) 0.015(8) 0.023(7) -0.006(7) C8 0.032(7) 0.031(7) 0.047(8) 0.001(6) 0.024(6) -0.006(6) C9 0.037(8) 0.079(11) 0.061(11) -0.008(8) 0.028(8) -0.019(8) C10 0.027(7) 0.038(8) 0.063(10) -0.005(7) 0.015(7) -0.002(6) C11 0.057(9) 0.041(9) 0.076(12) -0.008(8) 0.040(9) -0.020(7) C12 0.061(9) 0.028(7) 0.037(8) 0.001(6) 0.015(7) -0.017(6) C13 0.062(10) 0.054(9) 0.039(8) -0.012(7) 0.019(7) -0.023(8) C14 0.063(10) 0.052(9) 0.048(10) -0.009(7) 0.029(8) -0.002(8) C15 0.044(8) 0.051(9) 0.062(10) 0.006(7) 0.030(7) 0.004(7) C16 0.022(6) 0.036(7) 0.040(8) 0.002(6) 0.016(6) 0.010(5) C17 0.043(8) 0.032(8) 0.037(8) 0.002(6) 0.014(6) -0.001(6) C18 0.035(7) 0.037(8) 0.060(10) -0.008(7) 0.028(7) -0.010(6) C19 0.039(7) 0.044(8) 0.046(9) 0.009(7) 0.029(7) 0.008(6) C20 0.034(7) 0.040(8) 0.040(8) 0.002(6) 0.014(6) 0.003(6) C21 0.032(7) 0.022(7) 0.065(11) 0.002(6) 0.017(7) -0.001(6) C22 0.027(7) 0.043(8) 0.044(9) 0.003(7) 0.022(6) 0.002(6) C23 0.046(8) 0.037(8) 0.073(11) 0.020(8) 0.028(8) 0.011(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd C1 1.977(12) . ? Pd C16 2.018(12) . ? Pd N3 2.149(10) . ? Pd Cl 2.442(3) . ? O1 C14 1.395(18) . ? O1 C13 1.415(17) . ? O2 C22 1.204(15) . ? O3 C22 1.349(16) . ? O3 C23 1.435(16) . ? N1 C2 1.372(16) . ? N1 C1 1.374(15) . ? N1 C4 1.513(15) . ? N2 C1 1.371(16) . ? N2 C3 1.383(16) . ? N2 C8 1.519(15) . ? N3 C12 1.461(17) . ? N3 C15 1.487(16) . ? N3 H3 0.93 . ? C2 C3 1.356(18) . ? C2 H2 0.95 . ? C3 H3A 0.95 . ? C4 C7 1.515(18) . ? C4 C6 1.516(19) . ? C4 C5 1.543(18) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C9 1.49(2) . ? C8 C10 1.514(18) . ? C8 C11 1.524(18) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 C13 1.520(19) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.51(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C21 1.370(18) . ? C16 C17 1.414(18) . ? C17 C18 1.411(19) . ? C17 H17 0.95 . ? C18 C19 1.383(19) . ? C18 H18 0.95 . ? C19 C20 1.385(19) . ? C19 C22 1.482(19) . ? C20 C21 1.385(18) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd C16 87.3(5) . . ? C1 Pd N3 174.3(4) . . ? C16 Pd N3 92.0(4) . . ? C1 Pd Cl 90.9(4) . . ? C16 Pd Cl 176.9(3) . . ? N3 Pd Cl 90.0(3) . . ? C14 O1 C13 109.5(11) . . ? C22 O3 C23 115.4(11) . . ? C2 N1 C1 111.5(10) . . ? C2 N1 C4 120.6(10) . . ? C1 N1 C4 127.8(10) . . ? C1 N2 C3 111.3(10) . . ? C1 N2 C8 130.3(10) . . ? C3 N2 C8 118.3(10) . . ? C12 N3 C15 108.0(10) . . ? C12 N3 Pd 115.3(8) . . ? C15 N3 Pd 109.3(8) . . ? C12 N3 H3 108 . . ? C15 N3 H3 108 . . ? Pd N3 H3 108 . . ? N2 C1 N1 103.4(10) . . ? N2 C1 Pd 126.8(9) . . ? N1 C1 Pd 129.6(9) . . ? C3 C2 N1 107.1(11) . . ? C3 C2 H2 126.5 . . ? N1 C2 H2 126.5 . . ? C2 C3 N2 106.6(11) . . ? C2 C3 H3A 126.7 . . ? N2 C3 H3A 126.7 . . ? N1 C4 C7 109.5(10) . . ? N1 C4 C6 111.3(9) . . ? C7 C4 C6 111.7(12) . . ? N1 C4 C5 107.8(10) . . ? C7 C4 C5 108.7(11) . . ? C6 C4 C5 107.8(12) . . ? 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 108.3(11) . . ? C9 C8 N2 107.7(10) . . ? C10 C8 N2 113.5(10) . . ? C9 C8 C11 110.8(12) . . ? C10 C8 C11 110.0(11) . . ? N2 C8 C11 106.5(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 . . ? N3 C12 C13 113.5(12) . . ? N3 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N3 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? O1 C13 C12 110.9(11) . . ? O1 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108 . . ? O1 C14 C15 112.0(13) . . ? O1 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? O1 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N3 C15 C14 111.9(12) . . ? N3 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? N3 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C21 C16 C17 116.8(11) . . ? C21 C16 Pd 125.1(9) . . ? C17 C16 Pd 118.0(9) . . ? C18 C17 C16 119.8(12) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 121.5(12) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 118.2(12) . . ? C18 C19 C22 123.4(13) . . ? C20 C19 C22 118.4(13) . . ? C21 C20 C19 120.1(13) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C16 C21 C20 123.5(12) . . ? C16 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? O2 C22 O3 122.2(12) . . ? O2 C22 C19 124.6(12) . . ? O3 C22 C19 113.2(12) . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? #===END # Attachment 'aug1002.cif' data_aug1002 _database_code_depnum_ccdc_archive 'CCDC 727084' _audit_creation_date 2002-08-08T09:42:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ; '[{Pd(C3N2H2tBu2)(C6H4CH2O)}2].2(C6D6)' ; _chemical_formula_moiety '(C36 H52 N4 O2 Pd2).2(C6 D6)' _chemical_formula_sum 'C48 H52 D12 N4 O2 Pd2' _chemical_formula_weight 953.8 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_Int_Tables_number 14 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 11.8296(4) _cell_length_b 16.5642(6) _cell_length_c 12.7733(5) _cell_angle_alpha 90 _cell_angle_beta 116.119(1) _cell_angle_gamma 90 _cell_volume 2247.31(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5598 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 22.986 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 1.0107 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_unetI/netI 0.0713 _diffrn_reflns_number 9508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 22.98 _diffrn_reflns_theta_full 22.98 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 3073 _reflns_number_gt 2397 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+3.4839P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_number_reflns 3073 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.421 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.089 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd -0.00465(4) -0.05112(2) 0.10345(3) 0.02470(16) Uani 1 1 d . . . O O 0.1093(4) 0.0289(3) 0.0774(3) 0.0659(16) Uani 1 1 d . . . N1 N -0.2109(4) -0.1179(3) 0.1581(3) 0.0229(10) Uani 1 1 d . . . N2 N -0.1108(4) -0.2139(2) 0.1191(3) 0.0206(10) Uani 1 1 d . . . C1 C -0.1138(4) -0.1319(3) 0.1292(4) 0.0196(12) Uani 1 1 d . . . C2 C -0.2636(5) -0.1897(4) 0.1689(5) 0.0341(14) Uani 1 1 d . . . H2 H -0.3313 -0.1959 0.1892 0.041 Uiso 1 1 calc R . . C3 C -0.2013(5) -0.2493(4) 0.1453(5) 0.0348(14) Uani 1 1 d . . . H3 H -0.2166 -0.3055 0.1464 0.042 Uiso 1 1 calc R . . C4 C -0.2608(5) -0.0368(3) 0.1725(4) 0.0282(13) Uani 1 1 d . . . C5 C -0.2996(7) 0.0098(4) 0.0603(6) 0.062(2) Uani 1 1 d . . . H5A H -0.3654 -0.02 -0.0039 0.093 Uiso 1 1 calc R . . H5B H -0.2265 0.0168 0.0441 0.093 Uiso 1 1 calc R . . H5C H -0.3319 0.0628 0.0678 0.093 Uiso 1 1 calc R . . C6 C -0.1586(6) 0.0070(4) 0.2748(5) 0.0459(16) Uani 1 1 d . . . H6A H -0.1358 -0.0247 0.346 0.069 Uiso 1 1 calc R . . H6B H -0.1897 0.06 0.284 0.069 Uiso 1 1 calc R . . H6C H -0.0844 0.0138 0.2603 0.069 Uiso 1 1 calc R . . C7 C -0.3717(5) -0.0491(4) 0.1992(5) 0.0525(17) Uani 1 1 d . . . H7A H -0.3449 -0.0795 0.272 0.079 Uiso 1 1 calc R . . H7B H -0.4375 -0.0793 0.1354 0.079 Uiso 1 1 calc R . . H7C H -0.4049 0.0035 0.2074 0.079 Uiso 1 1 calc R . . C8 C -0.0185(5) -0.2627(3) 0.0946(5) 0.0309(13) Uani 1 1 d . . . C9 C 0.1039(5) -0.2670(4) 0.2054(5) 0.0388(15) Uani 1 1 d . . . H9A H 0.1377 -0.2124 0.2285 0.058 Uiso 1 1 calc R . . H9B H 0.1647 -0.3 0.1916 0.058 Uiso 1 1 calc R . . H9C H 0.0882 -0.2913 0.2677 0.058 Uiso 1 1 calc R . . C10 C 0.0023(6) -0.2247(4) -0.0039(5) 0.0501(18) Uani 1 1 d . . . H10A H 0.0365 -0.1702 0.0188 0.075 Uiso 1 1 calc R . . H10B H -0.078 -0.2219 -0.0742 0.075 Uiso 1 1 calc R . . H10C H 0.0619 -0.2576 -0.0197 0.075 Uiso 1 1 calc R . . C11 C -0.0721(6) -0.3470(4) 0.0564(6) 0.0483(17) Uani 1 1 d . . . H11A H -0.1506 -0.3433 -0.0156 0.073 Uiso 1 1 calc R . . H11B H -0.089 -0.3719 0.1177 0.073 Uiso 1 1 calc R . . H11C H -0.0112 -0.3799 0.0426 0.073 Uiso 1 1 calc R . . C12 C 0.1245(4) -0.0446(3) 0.2671(4) 0.0209(11) Uani 1 1 d . . . C13 C 0.2185(4) 0.0125(3) 0.2811(4) 0.0221(12) Uani 1 1 d . . . C14 C 0.3168(5) 0.0275(3) 0.3917(4) 0.0259(13) Uani 1 1 d . . . H14 H 0.38 0.0659 0.4004 0.031 Uiso 1 1 calc R . . C15 C 0.3222(5) -0.0136(4) 0.4885(4) 0.0344(15) Uani 1 1 d . . . H15 H 0.3889 -0.0034 0.5634 0.041 Uiso 1 1 calc R . . C16 C 0.2304(5) -0.0691(3) 0.4757(4) 0.0308(14) Uani 1 1 d . . . H16 H 0.234 -0.0974 0.5418 0.037 Uiso 1 1 calc R . . C17 C 0.1329(5) -0.0839(3) 0.3664(4) 0.0263(13) Uani 1 1 d . . . H17 H 0.0699 -0.122 0.3592 0.032 Uiso 1 1 calc R . . C18 C 0.2141(5) 0.0543(3) 0.1752(4) 0.0276(12) Uani 1 1 d . . . H18A H 0.2103 0.1135 0.1841 0.033 Uiso 1 1 calc R . . H18B H 0.2913 0.0418 0.1664 0.033 Uiso 1 1 calc R . . C19 C -0.4713(7) -0.2129(5) -0.1826(9) 0.074(2) Uani 1 1 d . . . H19 H -0.4123 -0.1736 -0.1355 0.089 Uiso 1 1 calc R . . C20 C -0.5008(6) -0.2775(5) -0.1328(6) 0.068(2) Uani 1 1 d . . . H20 H -0.4638 -0.2822 -0.0503 0.081 Uiso 1 1 calc R . . C21 C -0.5818(6) -0.3349(4) -0.1991(6) 0.0506(17) Uani 1 1 d . . . H21 H -0.5998 -0.3798 -0.1628 0.061 Uiso 1 1 calc R . . C22 C -0.6371(6) -0.3290(4) -0.3162(6) 0.0525(18) Uani 1 1 d . . . H22 H -0.6945 -0.3695 -0.3621 0.063 Uiso 1 1 calc R . . C23 C -0.6108(8) -0.2653(7) -0.3684(7) 0.071(2) Uani 1 1 d . . . H23 H -0.649 -0.2613 -0.451 0.085 Uiso 1 1 calc R . . C24 C -0.5280(9) -0.2059(5) -0.3009(11) 0.082(3) Uani 1 1 d . . . H24 H -0.5109 -0.1605 -0.3372 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd 0.0252(2) 0.0260(3) 0.0205(2) 0.0051(2) 0.00778(16) -0.0106(2) O 0.061(3) 0.089(4) 0.025(2) 0.020(2) -0.003(2) -0.058(3) N1 0.019(2) 0.021(3) 0.026(2) 0.0020(19) 0.0073(18) -0.004(2) N2 0.020(2) 0.014(2) 0.025(2) -0.0017(18) 0.0076(18) -0.0040(19) C1 0.023(3) 0.021(3) 0.015(3) 0.000(2) 0.008(2) 0.003(2) C2 0.028(3) 0.041(4) 0.040(3) -0.002(3) 0.021(3) -0.016(3) C3 0.042(4) 0.023(3) 0.043(3) -0.001(3) 0.022(3) -0.016(3) C4 0.023(3) 0.030(4) 0.033(3) -0.004(3) 0.013(2) 0.003(2) C5 0.081(5) 0.061(5) 0.051(4) 0.026(4) 0.036(4) 0.045(4) C6 0.049(4) 0.039(4) 0.056(4) -0.010(3) 0.029(3) 0.000(3) C7 0.037(4) 0.064(5) 0.059(4) -0.008(4) 0.023(3) 0.007(4) C8 0.035(3) 0.022(3) 0.038(3) 0.002(3) 0.019(2) 0.006(3) C9 0.026(3) 0.036(4) 0.048(4) -0.007(3) 0.011(3) 0.002(3) C10 0.076(5) 0.042(4) 0.055(4) 0.013(3) 0.050(4) 0.020(4) C11 0.044(4) 0.024(4) 0.068(4) -0.016(3) 0.017(3) 0.001(3) C12 0.019(3) 0.023(3) 0.024(3) -0.001(2) 0.012(2) 0.001(2) C13 0.021(3) 0.021(3) 0.022(3) -0.001(2) 0.008(2) 0.004(2) C14 0.016(3) 0.025(3) 0.034(3) -0.003(2) 0.009(2) 0.001(2) C15 0.030(3) 0.047(4) 0.022(3) -0.005(3) 0.007(2) 0.007(3) C16 0.035(3) 0.034(4) 0.026(3) 0.008(3) 0.015(2) 0.008(3) C17 0.023(3) 0.025(3) 0.032(3) 0.001(2) 0.013(2) -0.004(2) C18 0.029(3) 0.022(3) 0.026(3) 0.001(3) 0.006(2) -0.009(3) C19 0.061(5) 0.047(5) 0.126(8) -0.009(5) 0.051(5) -0.021(4) C20 0.057(5) 0.088(6) 0.056(5) -0.007(4) 0.023(4) -0.022(5) C21 0.051(4) 0.033(4) 0.071(5) 0.015(4) 0.030(4) 0.000(3) C22 0.044(4) 0.046(5) 0.066(5) -0.009(4) 0.024(4) 0.007(3) C23 0.059(5) 0.104(8) 0.059(5) 0.021(5) 0.034(4) 0.047(5) C24 0.078(6) 0.061(6) 0.146(9) 0.060(6) 0.085(6) 0.034(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd C12 1.976(5) . ? Pd C1 1.985(5) . ? Pd O 2.020(4) . ? Pd O 2.118(3) 3 ? Pd Pd 3.1813(7) 3 ? O C18 1.383(6) . ? O Pd 2.118(3) 3 ? N1 C1 1.372(6) . ? N1 C2 1.376(7) . ? N1 C4 1.512(7) . ? N2 C1 1.367(6) . ? N2 C3 1.385(6) . ? N2 C8 1.498(6) . ? C2 C3 1.342(8) . ? C4 C7 1.508(7) . ? C4 C5 1.510(8) . ? C4 C6 1.517(7) . ? C8 C9 1.517(7) . ? C8 C10 1.520(7) . ? C8 C11 1.522(8) . ? C12 C17 1.389(7) . ? C12 C13 1.410(7) . ? C13 C14 1.401(7) . ? C13 C18 1.501(7) . ? C14 C15 1.389(7) . ? C15 C16 1.376(8) . ? C16 C17 1.386(7) . ? C19 C24 1.362(12) . ? C19 C20 1.367(11) . ? C20 C21 1.350(9) . ? C21 C22 1.346(9) . ? C22 C23 1.356(11) . ? C23 C24 1.389(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 C12 Pd C1 96.75(19) . . ? C12 Pd O 82.95(17) . . ? C1 Pd O 178.6(2) . . ? C12 Pd O 162.34(18) . 3 ? C1 Pd O 100.82(16) . 3 ? O Pd O 79.53(15) . 3 ? C12 Pd Pd 123.82(14) . 3 ? C1 Pd Pd 139.43(13) . 3 ? O Pd Pd 40.90(10) . 3 ? O Pd Pd 38.63(10) 3 3 ? C18 O Pd 116.7(3) . . ? C18 O Pd 142.5(3) . 3 ? Pd O Pd 100.47(15) . 3 ? C1 N1 C2 110.6(4) . . ? C1 N1 C4 126.9(4) . . ? C2 N1 C4 122.5(4) . . ? C1 N2 C3 110.0(4) . . ? C1 N2 C8 127.4(4) . . ? C3 N2 C8 122.3(4) . . ? N2 C1 N1 104.6(4) . . ? N2 C1 Pd 127.5(3) . . ? N1 C1 Pd 127.9(4) . . ? C3 C2 N1 107.2(4) . . ? C2 C3 N2 107.6(5) . . ? C7 C4 C5 110.7(5) . . ? C7 C4 N1 109.4(4) . . ? C5 C4 N1 108.1(4) . . ? C7 C4 C6 108.2(5) . . ? C5 C4 C6 111.5(5) . . ? N1 C4 C6 108.9(4) . . ? N2 C8 C9 108.3(4) . . ? N2 C8 C10 110.4(4) . . ? C9 C8 C10 110.8(5) . . ? N2 C8 C11 108.8(4) . . ? C9 C8 C11 110.3(5) . . ? C10 C8 C11 108.1(5) . . ? C17 C12 C13 117.5(4) . . ? C17 C12 Pd 130.7(4) . . ? C13 C12 Pd 111.7(3) . . ? C14 C13 C12 120.4(4) . . ? C14 C13 C18 120.7(5) . . ? C12 C13 C18 118.9(4) . . ? C15 C14 C13 120.1(5) . . ? C16 C15 C14 119.8(5) . . ? C15 C16 C17 120.0(5) . . ? C16 C17 C12 122.1(5) . . ? O C18 C13 109.5(4) . . ? C24 C19 C20 118.7(8) . . ? C21 C20 C19 121.0(7) . . ? C22 C21 C20 120.7(6) . . ? C21 C22 C23 119.8(7) . . ? C22 C23 C24 119.9(7) . . ? C19 C24 C23 119.7(7) . . ?