# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Reiner Lomoth' _publ_contact_author_email REINER.LOMOTH@FOTOMOL.UU.SE _publ_section_title ; Pd-catalyzed diarylation of aniline - A way to a non-linear bis(terpyridyl)ligand providing increased electronic communication ; loop_ _publ_author_name 'Reiner Lomoth' 'Lars Eriksson' 'Olof Johansson' # Attachment 'ccdc.cif' data_rb_oj289 _database_code_depnum_ccdc_archive 'CCDC 677273' _audit_creation_method 'Manual editing of the cif from SHELXL-97' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H25 N7' _chemical_formula_sum 'C36 H25 N7' _chemical_formula_weight 555.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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' '-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 30.670(3) _cell_length_b 8.4665(12) _cell_length_c 22.428(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.063(12) _cell_angle_gamma 90.00 _cell_volume 5809.4(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.8 _exptl_crystal_description prism _exptl_crystal_colour colour_less _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'STOE IPDS' _diffrn_measurement_method '\f scan' _diffrn_detector_area_resol_mean 6 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 21890 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5402 _reflns_number_gt 2998 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Expose (STOE, 1998)' _computing_cell_refinement 'Cell (STOE, 1998)' _computing_data_reduction 'Integrate (STOE, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (Bergerhoff, 1996)' _computing_publication_material ? _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^)+(0.0682P)^2^] 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 5402 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 C11 C 0.08043(6) 1.1266(2) 0.18450(9) 0.0550(5) Uani 1 1 d . . . N12 N 0.09989(8) 1.1551(2) 0.13429(9) 0.0867(6) Uani 1 1 d . . . C13 C 0.09047(11) 1.2907(3) 0.10637(13) 0.1078(10) Uani 1 1 d . . . H13 H 0.1043 1.3120 0.0717 0.129 Uiso 1 1 calc R . . C14 C 0.06220(9) 1.3996(3) 0.12487(14) 0.0980(9) Uani 1 1 d . . . H14 H 0.0559 1.4906 0.1027 0.118 Uiso 1 1 calc R . . C15 C 0.04319(9) 1.3724(3) 0.17674(15) 0.0974(9) Uani 1 1 d . . . H15 H 0.0241 1.4459 0.1914 0.117 Uiso 1 1 calc R . . C16 C 0.05264(7) 1.2336(3) 0.20738(11) 0.0773(7) Uani 1 1 d . . . H16 H 0.0402 1.2132 0.2432 0.093 Uiso 1 1 calc R . . N21 N 0.06736(5) 0.93643(17) 0.26079(6) 0.0499(4) Uani 1 1 d . . . C22 C 0.09032(6) 0.9725(2) 0.21373(8) 0.0492(4) Uani 1 1 d . . . C23 C 0.12153(6) 0.8737(2) 0.19244(8) 0.0540(5) Uani 1 1 d . . . H23 H 0.1375 0.9053 0.1607 0.065 Uiso 1 1 calc R . . C24 C 0.12892(6) 0.7272(2) 0.21865(8) 0.0512(4) Uani 1 1 d . . . C25 C 0.10570(6) 0.6894(2) 0.26773(8) 0.0528(5) Uani 1 1 d . . . H25 H 0.1103 0.5933 0.2872 0.063 Uiso 1 1 calc R . . C26 C 0.07569(5) 0.7965(2) 0.28722(8) 0.0478(4) Uani 1 1 d . . . C31 C 0.05100(6) 0.7599(2) 0.34049(8) 0.0491(4) Uani 1 1 d . . . N32 N 0.06838(5) 0.6491(2) 0.37721(8) 0.0647(5) Uani 1 1 d . . . C33 C 0.04797(8) 0.6200(3) 0.42674(10) 0.0736(6) Uani 1 1 d . . . H33 H 0.0598 0.5438 0.4530 0.088 Uiso 1 1 calc R . . C34 C 0.01062(7) 0.6959(3) 0.44119(10) 0.0703(6) Uani 1 1 d . . . H34 H -0.0020 0.6729 0.4766 0.084 Uiso 1 1 calc R . . C35 C -0.00752(7) 0.8056(3) 0.40251(10) 0.0667(6) Uani 1 1 d . . . H35 H -0.0332 0.8572 0.4106 0.080 Uiso 1 1 calc R . . C36 C 0.01285(6) 0.8387(2) 0.35124(9) 0.0579(5) Uani 1 1 d . . . H36 H 0.0011 0.9132 0.3242 0.070 Uiso 1 1 calc R . . N4 N 0.15978(5) 0.61825(19) 0.19918(7) 0.0578(4) Uani 1 1 d . . . C51 C 0.18472(6) 0.5314(2) 0.24491(8) 0.0585(5) Uani 1 1 d . . . C52 C 0.18322(8) 0.3699(3) 0.24681(10) 0.0758(7) Uani 1 1 d . . . H52 H 0.1660 0.3134 0.2185 0.091 Uiso 1 1 calc R . . C53 C 0.20829(10) 0.2916(3) 0.29262(13) 0.0946(9) Uani 1 1 d . . . H53 H 0.2079 0.1820 0.2950 0.113 Uiso 1 1 calc R . . C54 C 0.23337(11) 0.3787(4) 0.33377(12) 0.1039(10) Uani 1 1 d . . . H54 H 0.2499 0.3266 0.3640 0.125 Uiso 1 1 calc R . . C55 C 0.23461(9) 0.5374(4) 0.33150(11) 0.0950(8) Uani 1 1 d . . . H55 H 0.2518 0.5941 0.3598 0.114 Uiso 1 1 calc R . . C56 C 0.21033(7) 0.6145(3) 0.28713(10) 0.0722(6) Uani 1 1 d . . . H56 H 0.2111 0.7242 0.2854 0.087 Uiso 1 1 calc R . . N61 N 0.19478(5) 0.58349(17) 0.02163(7) 0.0520(4) Uani 1 1 d . . . C62 C 0.22057(6) 0.5278(2) 0.06734(8) 0.0482(4) Uani 1 1 d . . . C63 C 0.20990(6) 0.5351(2) 0.12621(8) 0.0501(4) Uani 1 1 d . . . H63 H 0.2287 0.4930 0.1565 0.060 Uiso 1 1 calc R . . C64 C 0.17078(6) 0.6061(2) 0.13964(8) 0.0499(4) Uani 1 1 d . . . C65 C 0.14357(6) 0.6609(2) 0.09197(8) 0.0519(4) Uani 1 1 d . . . H65 H 0.1168 0.7063 0.0988 0.062 Uiso 1 1 calc R . . C66 C 0.15647(6) 0.6477(2) 0.03433(8) 0.0480(4) Uani 1 1 d . . . C71 C 0.26347(6) 0.4615(2) 0.05288(8) 0.0528(4) Uani 1 1 d . . . N72 N 0.28790(6) 0.3969(3) 0.09757(8) 0.0825(6) Uani 1 1 d . . . C73 C 0.32677(8) 0.3390(4) 0.08549(12) 0.0999(9) Uani 1 1 d . . . H73 H 0.3440 0.2933 0.1166 0.120 Uiso 1 1 calc R . . C74 C 0.34262(8) 0.3428(3) 0.03036(12) 0.0908(8) Uani 1 1 d . . . H74 H 0.3698 0.2999 0.0240 0.109 Uiso 1 1 calc R . . C75 C 0.31801(8) 0.4100(4) -0.01472(12) 0.0949(8) Uani 1 1 d . . . H75 H 0.3281 0.4157 -0.0528 0.114 Uiso 1 1 calc R . . C76 C 0.27750(8) 0.4705(3) -0.00363(10) 0.0794(7) Uani 1 1 d . . . H76 H 0.2599 0.5169 -0.0343 0.095 Uiso 1 1 calc R . . C81 C 0.12811(6) 0.7074(2) -0.01703(8) 0.0509(4) Uani 1 1 d . . . N82 N 0.09082(5) 0.7775(2) -0.00460(8) 0.0669(5) Uani 1 1 d . . . C83 C 0.06580(8) 0.8343(3) -0.05032(10) 0.0773(7) Uani 1 1 d . . . H83 H 0.0400 0.8847 -0.0420 0.093 Uiso 1 1 calc R . . C84 C 0.07530(8) 0.8241(3) -0.10877(10) 0.0756(6) Uani 1 1 d . . . H84 H 0.0566 0.8660 -0.1392 0.091 Uiso 1 1 calc R . . C85 C 0.11288(8) 0.7507(3) -0.12085(10) 0.0872(7) Uani 1 1 d . . . H85 H 0.1204 0.7406 -0.1601 0.105 Uiso 1 1 calc R . . C86 C 0.13979(7) 0.6912(3) -0.07468(9) 0.0748(6) Uani 1 1 d . . . H86 H 0.1657 0.6405 -0.0824 0.090 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 C11 0.0548(11) 0.0561(11) 0.0540(12) 0.0008(9) 0.0033(10) -0.0011(9) N12 0.1259(17) 0.0690(11) 0.0685(12) 0.0158(9) 0.0304(13) 0.0198(11) C13 0.157(3) 0.0793(16) 0.091(2) 0.0330(15) 0.038(2) 0.0279(18) C14 0.0975(19) 0.0740(16) 0.123(2) 0.0342(15) 0.0107(18) 0.0116(14) C15 0.0821(16) 0.0706(15) 0.143(3) 0.0213(16) 0.0301(18) 0.0205(12) C16 0.0717(14) 0.0686(13) 0.0944(18) 0.0104(12) 0.0253(13) 0.0117(11) N21 0.0470(8) 0.0591(9) 0.0436(9) -0.0013(7) 0.0034(7) 0.0015(7) C22 0.0491(10) 0.0552(10) 0.0429(10) -0.0006(8) 0.0018(8) 0.0001(8) C23 0.0551(11) 0.0630(11) 0.0451(11) 0.0038(9) 0.0115(9) 0.0035(9) C24 0.0489(10) 0.0636(11) 0.0418(10) 0.0007(8) 0.0075(9) 0.0098(8) C25 0.0543(10) 0.0613(11) 0.0436(10) 0.0033(8) 0.0091(9) 0.0081(9) C26 0.0427(9) 0.0597(11) 0.0408(10) -0.0008(8) 0.0019(8) 0.0016(8) C31 0.0455(10) 0.0590(10) 0.0433(10) -0.0020(8) 0.0059(8) -0.0021(8) N32 0.0641(10) 0.0739(11) 0.0582(10) 0.0136(9) 0.0197(9) 0.0095(8) C33 0.0772(15) 0.0818(14) 0.0643(14) 0.0192(11) 0.0218(12) 0.0048(11) C34 0.0692(13) 0.0820(14) 0.0633(14) 0.0004(11) 0.0294(12) -0.0087(12) C35 0.0518(11) 0.0790(13) 0.0717(14) -0.0024(11) 0.0204(11) 0.0012(10) C36 0.0456(10) 0.0706(12) 0.0581(12) -0.0012(9) 0.0075(9) 0.0019(9) N4 0.0612(9) 0.0751(10) 0.0382(8) 0.0066(7) 0.0129(8) 0.0219(8) C51 0.0597(11) 0.0762(13) 0.0412(11) 0.0135(10) 0.0166(10) 0.0235(10) C52 0.0845(15) 0.0789(15) 0.0666(15) 0.0147(12) 0.0242(13) 0.0201(12) C53 0.120(2) 0.0874(17) 0.0802(19) 0.0253(15) 0.0354(18) 0.0429(17) C54 0.122(2) 0.137(3) 0.0537(16) 0.0162(17) 0.0162(17) 0.063(2) C55 0.0987(19) 0.127(2) 0.0579(15) 0.0025(15) -0.0030(14) 0.0436(17) C56 0.0746(14) 0.0939(15) 0.0485(13) 0.0046(11) 0.0072(12) 0.0206(12) N61 0.0508(9) 0.0631(9) 0.0428(9) 0.0008(7) 0.0071(8) 0.0045(7) C62 0.0472(9) 0.0558(10) 0.0423(10) 0.0005(8) 0.0071(9) 0.0018(8) C63 0.0477(10) 0.0601(10) 0.0428(10) 0.0021(8) 0.0061(8) 0.0036(8) C64 0.0535(10) 0.0575(10) 0.0397(10) 0.0035(8) 0.0099(9) 0.0034(8) C65 0.0494(10) 0.0637(11) 0.0435(11) 0.0039(8) 0.0095(9) 0.0069(8) C66 0.0463(9) 0.0554(10) 0.0428(10) 0.0024(8) 0.0069(9) 0.0014(8) C71 0.0489(10) 0.0657(11) 0.0444(11) 0.0004(9) 0.0085(9) 0.0052(9) N72 0.0605(11) 0.1305(16) 0.0579(12) 0.0179(11) 0.0136(10) 0.0320(11) C73 0.0645(14) 0.165(3) 0.0720(17) 0.0222(16) 0.0144(13) 0.0458(16) C74 0.0631(14) 0.135(2) 0.0762(17) 0.0046(15) 0.0185(13) 0.0336(15) C75 0.0782(16) 0.146(2) 0.0638(16) 0.0060(15) 0.0296(14) 0.0362(16) C76 0.0698(14) 0.1187(18) 0.0508(13) 0.0046(12) 0.0123(11) 0.0290(13) C81 0.0500(10) 0.0580(10) 0.0453(11) 0.0040(8) 0.0065(9) 0.0016(8) N82 0.0597(10) 0.0874(12) 0.0545(11) 0.0143(9) 0.0115(9) 0.0188(9) C83 0.0687(14) 0.0999(16) 0.0637(15) 0.0214(12) 0.0074(12) 0.0263(12) C84 0.0776(15) 0.0926(15) 0.0556(14) 0.0154(11) -0.0029(12) 0.0191(12) C85 0.0933(17) 0.126(2) 0.0430(13) 0.0075(12) 0.0054(13) 0.0298(15) C86 0.0700(13) 0.1092(17) 0.0459(12) 0.0025(11) 0.0080(11) 0.0247(13) _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 C11 N12 1.333(3) . ? C11 C16 1.369(3) . ? C11 C22 1.481(3) . ? N12 C13 1.330(3) . ? C13 C14 1.351(4) . ? C13 H13 0.9300 . ? C14 C15 1.357(4) . ? C14 H14 0.9300 . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N21 C26 1.341(2) . ? N21 C22 1.345(2) . ? C22 C23 1.382(2) . ? C23 C24 1.385(3) . ? C23 H23 0.9300 . ? C24 C25 1.390(2) . ? C24 N4 1.413(2) . ? C25 C26 1.385(2) . ? C25 H25 0.9300 . ? C26 C31 1.492(2) . ? C31 N32 1.335(2) . ? C31 C36 1.383(2) . ? N32 C33 1.336(2) . ? C33 C34 1.372(3) . ? C33 H33 0.9300 . ? C34 C35 1.362(3) . ? C34 H34 0.9300 . ? C35 C36 1.376(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? N4 C64 1.404(2) . ? N4 C51 1.438(2) . ? C51 C52 1.368(3) . ? C51 C56 1.380(3) . ? C52 C53 1.405(4) . ? C52 H52 0.9300 . ? C53 C54 1.374(4) . ? C53 H53 0.9300 . ? C54 C55 1.345(4) . ? C54 H54 0.9300 . ? C55 C56 1.366(3) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? N61 C62 1.336(2) . ? N61 C66 1.343(2) . ? C62 C63 1.384(2) . ? C62 C71 1.487(2) . ? C63 C64 1.394(2) . ? C63 H63 0.9300 . ? C64 C65 1.389(3) . ? C65 C66 1.383(2) . ? C65 H65 0.9300 . ? C66 C81 1.482(3) . ? C71 N72 1.326(3) . ? C71 C76 1.369(3) . ? N72 C73 1.335(3) . ? C73 C74 1.361(3) . ? C73 H73 0.9300 . ? C74 C75 1.345(3) . ? C74 H74 0.9300 . ? C75 C76 1.383(3) . ? C75 H75 0.9300 . ? C76 H76 0.9300 . ? C81 N82 1.335(2) . ? C81 C86 1.373(3) . ? N82 C83 1.327(3) . ? C83 C84 1.366(3) . ? C83 H83 0.9300 . ? C84 C85 1.354(3) . ? C84 H84 0.9300 . ? C85 C86 1.373(3) . ? C85 H85 0.9300 . ? C86 H86 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 C11 C16 121.66(19) . . ? N12 C11 C22 116.30(16) . . ? C16 C11 C22 122.04(18) . . ? C13 N12 C11 117.3(2) . . ? N12 C13 C14 124.6(3) . . ? N12 C13 H13 117.7 . . ? C14 C13 H13 117.7 . . ? C13 C14 C15 118.1(2) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C14 C15 C16 118.9(2) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C11 C16 C15 119.4(2) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C26 N21 C22 116.98(14) . . ? N21 C22 C23 123.21(16) . . ? N21 C22 C11 116.44(15) . . ? C23 C22 C11 120.36(16) . . ? C22 C23 C24 119.49(16) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C23 C24 C25 117.69(16) . . ? C23 C24 N4 123.14(16) . . ? C25 C24 N4 119.13(16) . . ? C26 C25 C24 119.25(17) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? N21 C26 C25 123.30(16) . . ? N21 C26 C31 116.48(15) . . ? C25 C26 C31 120.21(16) . . ? N32 C31 C36 122.52(17) . . ? N32 C31 C26 115.92(15) . . ? C36 C31 C26 121.55(17) . . ? C31 N32 C33 116.90(17) . . ? N32 C33 C34 123.9(2) . . ? N32 C33 H33 118.0 . . ? C34 C33 H33 118.0 . . ? C35 C34 C33 118.62(19) . . ? C35 C34 H34 120.7 . . ? C33 C34 H34 120.7 . . ? C34 C35 C36 118.81(19) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? C35 C36 C31 119.2(2) . . ? C35 C36 H36 120.4 . . ? C31 C36 H36 120.4 . . ? C64 N4 C24 123.60(15) . . ? C64 N4 C51 119.29(14) . . ? C24 N4 C51 116.60(14) . . ? C52 C51 C56 120.5(2) . . ? C52 C51 N4 121.1(2) . . ? C56 C51 N4 118.48(19) . . ? C51 C52 C53 118.4(3) . . ? C51 C52 H52 120.8 . . ? C53 C52 H52 120.8 . . ? C54 C53 C52 119.3(3) . . ? C54 C53 H53 120.4 . . ? C52 C53 H53 120.4 . . ? C55 C54 C53 121.8(3) . . ? C55 C54 H54 119.1 . . ? C53 C54 H54 119.1 . . ? C54 C55 C56 119.3(3) . . ? C54 C55 H55 120.3 . . ? C56 C55 H55 120.3 . . ? C55 C56 C51 120.7(2) . . ? C55 C56 H56 119.6 . . ? C51 C56 H56 119.6 . . ? C62 N61 C66 117.35(14) . . ? N61 C62 C63 123.31(16) . . ? N61 C62 C71 116.80(15) . . ? C63 C62 C71 119.84(17) . . ? C62 C63 C64 119.39(17) . . ? C62 C63 H63 120.3 . . ? C64 C63 H63 120.3 . . ? C65 C64 C63 117.21(16) . . ? C65 C64 N4 122.40(16) . . ? C63 C64 N4 120.38(17) . . ? C66 C65 C64 119.76(16) . . ? C66 C65 H65 120.1 . . ? C64 C65 H65 120.1 . . ? N61 C66 C65 122.93(17) . . ? N61 C66 C81 116.56(15) . . ? C65 C66 C81 120.51(16) . . ? N72 C71 C76 121.67(18) . . ? N72 C71 C62 116.87(15) . . ? C76 C71 C62 121.45(18) . . ? C71 N72 C73 117.59(18) . . ? N72 C73 C74 123.9(2) . . ? N72 C73 H73 118.1 . . ? C74 C73 H73 118.1 . . ? C75 C74 C73 118.4(2) . . ? C75 C74 H74 120.8 . . ? C73 C74 H74 120.8 . . ? C74 C75 C76 119.0(2) . . ? C74 C75 H75 120.5 . . ? C76 C75 H75 120.5 . . ? C71 C76 C75 119.4(2) . . ? C71 C76 H76 120.3 . . ? C75 C76 H76 120.3 . . ? N82 C81 C86 121.68(19) . . ? N82 C81 C66 116.98(16) . . ? C86 C81 C66 121.34(17) . . ? C83 N82 C81 117.19(17) . . ? N82 C83 C84 124.6(2) . . ? N82 C83 H83 117.7 . . ? C84 C83 H83 117.7 . . ? C85 C84 C83 117.6(2) . . ? C85 C84 H84 121.2 . . ? C83 C84 H84 121.2 . . ? C84 C85 C86 119.5(2) . . ? C84 C85 H85 120.3 . . ? C86 C85 H85 120.3 . . ? C81 C86 C85 119.4(2) . . ? C81 C86 H86 120.3 . . ? C85 C86 H86 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 N12 C13 -1.5(4) . . . . ? C22 C11 N12 C13 178.1(2) . . . . ? C11 N12 C13 C14 -1.0(5) . . . . ? N12 C13 C14 C15 2.6(5) . . . . ? C13 C14 C15 C16 -1.6(5) . . . . ? N12 C11 C16 C15 2.4(4) . . . . ? C22 C11 C16 C15 -177.2(2) . . . . ? C14 C15 C16 C11 -0.7(4) . . . . ? C26 N21 C22 C23 -0.4(3) . . . . ? C26 N21 C22 C11 179.30(16) . . . . ? N12 C11 C22 N21 -173.35(19) . . . . ? C16 C11 C22 N21 6.2(3) . . . . ? N12 C11 C22 C23 6.3(3) . . . . ? C16 C11 C22 C23 -174.1(2) . . . . ? N21 C22 C23 C24 2.6(3) . . . . ? C11 C22 C23 C24 -177.09(18) . . . . ? C22 C23 C24 C25 -3.1(3) . . . . ? C22 C23 C24 N4 179.17(17) . . . . ? C23 C24 C25 C26 1.7(3) . . . . ? N4 C24 C25 C26 179.46(17) . . . . ? C22 N21 C26 C25 -1.2(3) . . . . ? C22 N21 C26 C31 178.20(16) . . . . ? C24 C25 C26 N21 0.5(3) . . . . ? C24 C25 C26 C31 -178.84(17) . . . . ? N21 C26 C31 N32 -159.57(16) . . . . ? C25 C26 C31 N32 19.8(3) . . . . ? N21 C26 C31 C36 19.4(3) . . . . ? C25 C26 C31 C36 -161.20(18) . . . . ? C36 C31 N32 C33 -2.2(3) . . . . ? C26 C31 N32 C33 176.76(19) . . . . ? C31 N32 C33 C34 0.6(3) . . . . ? N32 C33 C34 C35 1.3(4) . . . . ? C33 C34 C35 C36 -1.5(3) . . . . ? C34 C35 C36 C31 0.0(3) . . . . ? N32 C31 C36 C35 1.9(3) . . . . ? C26 C31 C36 C35 -176.95(18) . . . . ? C23 C24 N4 C64 -31.0(3) . . . . ? C25 C24 N4 C64 151.27(19) . . . . ? C23 C24 N4 C51 140.7(2) . . . . ? C25 C24 N4 C51 -37.0(3) . . . . ? C64 N4 C51 C52 -67.6(2) . . . . ? C24 N4 C51 C52 120.3(2) . . . . ? C64 N4 C51 C56 112.5(2) . . . . ? C24 N4 C51 C56 -59.6(2) . . . . ? C56 C51 C52 C53 0.0(3) . . . . ? N4 C51 C52 C53 -179.94(17) . . . . ? C51 C52 C53 C54 0.0(3) . . . . ? C52 C53 C54 C55 0.0(4) . . . . ? C53 C54 C55 C56 0.0(4) . . . . ? C54 C55 C56 C51 0.0(4) . . . . ? C52 C51 C56 C55 0.0(3) . . . . ? N4 C51 C56 C55 179.97(19) . . . . ? C66 N61 C62 C63 -0.8(3) . . . . ? C66 N61 C62 C71 -178.18(15) . . . . ? N61 C62 C63 C64 -1.2(3) . . . . ? C71 C62 C63 C64 176.14(16) . . . . ? C62 C63 C64 C65 2.4(3) . . . . ? C62 C63 C64 N4 -178.44(17) . . . . ? C24 N4 C64 C65 -21.1(3) . . . . ? C51 N4 C64 C65 167.32(18) . . . . ? C24 N4 C64 C63 159.79(17) . . . . ? C51 N4 C64 C63 -11.7(3) . . . . ? C63 C64 C65 C66 -1.8(3) . . . . ? N4 C64 C65 C66 179.06(17) . . . . ? C62 N61 C66 C65 1.4(3) . . . . ? C62 N61 C66 C81 -179.40(15) . . . . ? C64 C65 C66 N61 -0.1(3) . . . . ? C64 C65 C66 C81 -179.22(16) . . . . ? N61 C62 C71 N72 -175.75(18) . . . . ? C63 C62 C71 N72 6.8(3) . . . . ? N61 C62 C71 C76 5.9(3) . . . . ? C63 C62 C71 C76 -171.6(2) . . . . ? C76 C71 N72 C73 -0.7(4) . . . . ? C62 C71 N72 C73 -179.0(2) . . . . ? C71 N72 C73 C74 0.1(4) . . . . ? N72 C73 C74 C75 0.6(5) . . . . ? C73 C74 C75 C76 -0.9(5) . . . . ? N72 C71 C76 C75 0.4(4) . . . . ? C62 C71 C76 C75 178.7(2) . . . . ? C74 C75 C76 C71 0.4(4) . . . . ? N61 C66 C81 N82 -177.21(16) . . . . ? C65 C66 C81 N82 2.0(3) . . . . ? N61 C66 C81 C86 2.7(3) . . . . ? C65 C66 C81 C86 -178.11(19) . . . . ? C86 C81 N82 C83 -1.4(3) . . . . ? C66 C81 N82 C83 178.48(19) . . . . ? C81 N82 C83 C84 0.9(4) . . . . ? N82 C83 C84 C85 0.0(4) . . . . ? C83 C84 C85 C86 -0.4(4) . . . . ? N82 C81 C86 C85 1.0(3) . . . . ? C66 C81 C86 C85 -178.9(2) . . . . ? C84 C85 C86 C81 -0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.196 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.031