# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Michael J. Cook' 'Andrew Cammidge' 'David L. Hughes' 'Fabien Nekelson' 'Muhibur Rahman' _publ_contact_author_name 'Michael J Cook' _publ_contact_author_address ; School of Chemical Sciences and Pharmacy University of East Anglia Wolfson Materials and Catalysis Cen Norwich NR4 7TJ UNITED KINGDOM ; _publ_contact_author_email M.COOK@UEA.AC.UK _publ_section_title ; A remarkable side-product from the synthesis of an octaalkyl-phthalocyanine: formation of a tetrabenzotriazaporphyrin ; data_fabien1 _database_code_depnum_ccdc_archive 'CCDC 252175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C81 H115 N7' _chemical_formula_structural 'a tetrabenzotriazaporphyrin' _chemical_formula_sum 'C81 H115 N7' _chemical_formula_weight 1186.80 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 #(no. 2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.220(15) _cell_length_b 9.633(11) _cell_length_c 19.87(4) _cell_angle_alpha 80.13(5) _cell_angle_beta 91.14(8) _cell_angle_gamma 84.48(6) _cell_volume 1729(5) _cell_formula_units_Z 1 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 650 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis-IIc' _diffrn_measurement_method 'image-plate oscillation photos' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6474 _diffrn_reflns_av_R_equivalents 0.2466 _diffrn_reflns_av_sigmaI/netI 0.2560 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 22.00 _reflns_number_total 3873 _reflns_number_gt 2384 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'MSC R-Axis-II control software' _computing_cell_refinement 'DENZO/CELL (Otwinowski and Minor, 1985)' _computing_data_reduction 'DENZO, SCALEPACK (Otwinowski and Minor, 1985)' _computing_structure_solution 'SHELXS (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^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 3873 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.1976 _refine_ls_wR_factor_gt 0.1754 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 N1 N 0.3021(4) 0.4604(3) 0.45752(16) 0.0492(9) Uani 1 1 d . . . H1 H 0.3856 0.4747 0.4736 0.058(13) Uiso 1 1 calc R . . C2 C 0.2138(5) 0.3702(4) 0.4930(2) 0.0471(10) Uani 1 1 d . . . C3 C 0.0812(5) 0.3830(4) 0.44851(19) 0.0465(10) Uani 1 1 d . . . C4 C -0.0511(5) 0.3189(4) 0.4587(2) 0.0498(10) Uani 1 1 d . . . C41 C -0.0739(5) 0.2102(4) 0.5204(2) 0.0531(11) Uani 1 1 d . . . H41A H -0.0677 0.2546 0.5605 0.064 Uiso 1 1 calc R . . H41B H 0.0061 0.1357 0.5244 0.064 Uiso 1 1 calc R . . C42 C -0.2152(5) 0.1418(4) 0.5221(2) 0.0560(11) Uani 1 1 d . . . H42A H -0.2961 0.2143 0.5213 0.067 Uiso 1 1 calc R . . H42B H -0.2248 0.1001 0.4814 0.067 Uiso 1 1 calc R . . C43 C -0.2241(5) 0.0287(4) 0.5844(2) 0.0561(11) Uani 1 1 d . . . H43A H -0.2208 0.0727 0.6247 0.067 Uiso 1 1 calc R . . H43B H -0.1384 -0.0390 0.5868 0.067 Uiso 1 1 calc R . . C44 C -0.3585(5) -0.0520(4) 0.5869(2) 0.0565(11) Uani 1 1 d . . . H44A H -0.4448 0.0151 0.5837 0.068 Uiso 1 1 calc R . . H44B H -0.3608 -0.0990 0.5475 0.068 Uiso 1 1 calc R . . C45 C -0.3640(5) -0.1607(4) 0.6506(2) 0.0588(11) Uani 1 1 d . . . H45A H -0.3659 -0.1131 0.6899 0.071 Uiso 1 1 calc R . . H45B H -0.2755 -0.2253 0.6549 0.071 Uiso 1 1 calc R . . C46 C -0.4936(5) -0.2455(4) 0.6521(2) 0.0650(12) Uani 1 1 d . . . H46A H -0.4888 -0.3140 0.6935 0.098 Uiso 1 1 calc R . . H46B H -0.4926 -0.2934 0.6135 0.098 Uiso 1 1 calc R . . H46C H -0.5818 -0.1831 0.6502 0.098 Uiso 1 1 calc R . . C5 C -0.1561(5) 0.3612(4) 0.4072(2) 0.0554(11) Uani 1 1 d . . . H5 H -0.2459 0.3250 0.4125 0.066 Uiso 1 1 calc R . . C6 C -0.1349(5) 0.4556(4) 0.3474(2) 0.0549(11) Uani 1 1 d . . . H6 H -0.2108 0.4796 0.3147 0.066 Uiso 1 1 calc R . . C7 C -0.0054(5) 0.5144(4) 0.3352(2) 0.0505(10) Uani 1 1 d . . . C71 C 0.0199(4) 0.6113(4) 0.26855(19) 0.0506(10) Uani 1 1 d . . . H71A H 0.1053 0.5707 0.2483 0.061 Uiso 1 1 calc R . . H71B H 0.0423 0.7016 0.2792 0.061 Uiso 1 1 calc R . . C72 C -0.1048(5) 0.6390(4) 0.2152(2) 0.0525(10) Uani 1 1 d . . . H72A H -0.1910 0.6806 0.2343 0.063 Uiso 1 1 calc R . . H72B H -0.1271 0.5499 0.2029 0.063 Uiso 1 1 calc R . . C73 C -0.0662(5) 0.7383(4) 0.1512(2) 0.0544(11) Uani 1 1 d . . . H73A H -0.0356 0.8236 0.1645 0.065 Uiso 1 1 calc R . . H73B H 0.0160 0.6929 0.1307 0.065 Uiso 1 1 calc R . . C74 C -0.1897(5) 0.7803(5) 0.0975(2) 0.0616(12) Uani 1 1 d . . . H74A H -0.2129 0.6967 0.0800 0.074 Uiso 1 1 calc R . . H74B H -0.2757 0.8164 0.1189 0.074 Uiso 1 1 calc R . . C75 C -0.1533(5) 0.8919(5) 0.0381(2) 0.0664(12) Uani 1 1 d . . . H75A H -0.1213 0.9720 0.0559 0.080 Uiso 1 1 calc R . . H75B H -0.0731 0.8527 0.0140 0.080 Uiso 1 1 calc R . . C76 C -0.2805(6) 0.9430(5) -0.0117(2) 0.0851(16) Uani 1 1 d . . . H76A H -0.2515 1.0127 -0.0481 0.128 Uiso 1 1 calc R . . H76B H -0.3594 0.9844 0.0115 0.128 Uiso 1 1 calc R . . H76C H -0.3116 0.8645 -0.0302 0.128 Uiso 1 1 calc R . . C8 C 0.1041(4) 0.4784(4) 0.38834(19) 0.0467(10) Uani 1 1 d . . . C9 C 0.2482(5) 0.5252(4) 0.3952(2) 0.0497(10) Uani 1 1 d . . . N10 N 0.3091(4) 0.6160(3) 0.34854(16) 0.0513(9) Uani 1 1 d . . . N11 N 0.5297(4) 0.6337(3) 0.41425(16) 0.0537(9) Uani 1 1 d . . . C12 C 0.4393(5) 0.6645(4) 0.35774(19) 0.0480(10) Uani 1 1 d . . . C13 C 0.4961(4) 0.7723(4) 0.30514(19) 0.0465(10) Uani 1 1 d . . . C14 C 0.4474(4) 0.8363(4) 0.2388(2) 0.0499(10) Uani 1 1 d . . . C141 C 0.3229(5) 0.7937(4) 0.1996(2) 0.0538(11) Uani 1 1 d . . . H14A H 0.2597 0.8778 0.1800 0.065 Uiso 1 1 calc R . . H14B H 0.2664 0.7337 0.2310 0.065 Uiso 1 1 calc R . . C142 C 0.3731(5) 0.7146(4) 0.1426(2) 0.0590(11) Uani 1 1 d . . . H14C H 0.2884 0.7034 0.1150 0.071 Uiso 1 1 calc R . . H14D H 0.4360 0.7718 0.1134 0.071 Uiso 1 1 calc R . . C143 C 0.4541(5) 0.5702(4) 0.1675(2) 0.0625(12) Uani 1 1 d . . . H14E H 0.3891 0.5111 0.1943 0.075 Uiso 1 1 calc R . . H14F H 0.5351 0.5807 0.1975 0.075 Uiso 1 1 calc R . . C144 C 0.5124(5) 0.4949(4) 0.1109(2) 0.0621(12) Uani 1 1 d . . . H14G H 0.4322 0.4899 0.0794 0.074 Uiso 1 1 calc R . . H14H H 0.5818 0.5515 0.0859 0.074 Uiso 1 1 calc R . . C145 C 0.5849(6) 0.3489(5) 0.1346(2) 0.0774(14) Uani 1 1 d . . . H14I H 0.5137 0.2899 0.1565 0.093 Uiso 1 1 calc R . . H14J H 0.6608 0.3525 0.1686 0.093 Uiso 1 1 calc R . . C146 C 0.6529(6) 0.2797(5) 0.0762(3) 0.0888(17) Uani 1 1 d . . . H14K H 0.6994 0.1872 0.0948 0.133 Uiso 1 1 calc R . . H14L H 0.7237 0.3373 0.0544 0.133 Uiso 1 1 calc R . . H14M H 0.5777 0.2717 0.0434 0.133 Uiso 1 1 calc R . . C15 C 0.5261(5) 0.9437(4) 0.2079(2) 0.0549(11) Uani 1 1 d . . . H15 H 0.4960 0.9910 0.1643 0.066 Uiso 1 1 calc R . . C16 C 0.6482(5) 0.9842(4) 0.2391(2) 0.0563(11) Uani 1 1 d . . . H16 H 0.6953 1.0584 0.2159 0.068 Uiso 1 1 calc R . . C17 C 0.7020(5) 0.9177(4) 0.3034(2) 0.0526(11) Uani 1 1 d . . . C171 C 0.8344(5) 0.9650(4) 0.3366(2) 0.0553(11) Uani 1 1 d . . . H17A H 0.9131 0.8894 0.3400 0.066 Uiso 1 1 calc R . . H17B H 0.8107 0.9765 0.3828 0.066 Uiso 1 1 calc R . . C172 C 0.8913(5) 1.1020(4) 0.3010(2) 0.0573(11) Uani 1 1 d . . . H17C H 0.8082 1.1701 0.2851 0.069 Uiso 1 1 calc R . . H17D H 0.9458 1.1402 0.3346 0.069 Uiso 1 1 calc R . . C173 C 0.9883(5) 1.0887(4) 0.2404(2) 0.0613(12) Uani 1 1 d . . . H17E H 1.0792 1.0327 0.2568 0.074 Uiso 1 1 calc R . . H17F H 0.9401 1.0394 0.2091 0.074 Uiso 1 1 calc R . . C174 C 1.0213(6) 1.2324(4) 0.2024(2) 0.0674(13) Uani 1 1 d . . . H17G H 0.9298 1.2890 0.1878 0.081 Uiso 1 1 calc R . . H17H H 1.0712 1.2801 0.2338 0.081 Uiso 1 1 calc R . . C175 C 1.1118(6) 1.2272(5) 0.1416(2) 0.0795(15) Uani 1 1 d . . . H17I H 1.0696 1.1683 0.1130 0.095 Uiso 1 1 calc R . . H17J H 1.2088 1.1835 0.1566 0.095 Uiso 1 1 calc R . . C176 C 1.1237(7) 1.3733(5) 0.0993(3) 0.0889(17) Uani 1 1 d . . . H17K H 1.1840 1.3640 0.0611 0.133 Uiso 1 1 calc R . . H17L H 1.1663 1.4319 0.1272 0.133 Uiso 1 1 calc R . . H17M H 1.0283 1.4158 0.0829 0.133 Uiso 1 1 calc R . . C18 C 0.6255(5) 0.8072(4) 0.33605(19) 0.0484(10) Uani 1 1 d . . . C19 C 0.6434(5) 0.7153(4) 0.4029(2) 0.0482(10) Uani 1 1 d . . . N20 N 0.7619(4) 0.7105(3) 0.44574(17) 0.0439(9) Uani 0.50 1 d P . 1 C20 C 0.7619(4) 0.7105(3) 0.44574(17) 0.0439(9) Uani 0.50 1 d P . 2 H20 H 0.8329 0.7696 0.4306 0.027(16) Uiso 0.50 1 calc PR . 2 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 N1 0.041(2) 0.0549(19) 0.052(2) -0.0090(16) 0.0038(18) -0.0054(17) C2 0.041(3) 0.048(2) 0.056(3) -0.0143(19) 0.012(2) -0.0051(19) C3 0.042(3) 0.048(2) 0.050(2) -0.0129(17) 0.0061(19) 0.0020(19) C4 0.046(3) 0.048(2) 0.057(3) -0.0156(18) 0.008(2) 0.001(2) C41 0.051(3) 0.053(2) 0.058(2) -0.0141(18) 0.013(2) -0.007(2) C42 0.051(3) 0.059(2) 0.062(3) -0.0190(19) 0.013(2) -0.006(2) C43 0.043(3) 0.066(3) 0.062(3) -0.015(2) 0.009(2) -0.009(2) C44 0.041(3) 0.062(3) 0.068(3) -0.014(2) 0.007(2) -0.003(2) C45 0.047(3) 0.060(3) 0.070(3) -0.014(2) 0.009(2) -0.006(2) C46 0.051(3) 0.064(3) 0.081(3) -0.014(2) 0.015(2) -0.008(2) C5 0.046(3) 0.060(3) 0.063(3) -0.016(2) 0.011(2) -0.008(2) C6 0.051(3) 0.054(2) 0.060(3) -0.0138(19) 0.002(2) -0.001(2) C7 0.041(3) 0.053(2) 0.058(3) -0.0178(18) 0.007(2) 0.004(2) C71 0.039(3) 0.056(2) 0.056(2) -0.0124(18) 0.0010(19) -0.0004(19) C72 0.044(3) 0.054(2) 0.060(3) -0.0139(18) -0.001(2) -0.0027(19) C73 0.040(3) 0.061(2) 0.061(3) -0.0114(19) -0.003(2) -0.003(2) C74 0.050(3) 0.075(3) 0.059(3) -0.012(2) 0.004(2) -0.001(2) C75 0.062(3) 0.071(3) 0.063(3) -0.010(2) -0.002(2) 0.005(2) C76 0.081(4) 0.097(3) 0.069(3) -0.007(3) -0.003(3) 0.019(3) C8 0.034(3) 0.052(2) 0.053(2) -0.0126(18) 0.0046(19) 0.0035(19) C9 0.049(3) 0.052(2) 0.049(3) -0.0097(19) 0.009(2) -0.002(2) N10 0.041(2) 0.0559(19) 0.059(2) -0.0137(16) 0.0075(17) -0.0065(17) N11 0.055(3) 0.055(2) 0.052(2) -0.0111(15) 0.0104(19) -0.0025(18) C12 0.046(3) 0.052(2) 0.046(2) -0.0102(18) 0.002(2) -0.002(2) C13 0.042(3) 0.045(2) 0.053(2) -0.0108(18) 0.006(2) 0.0001(19) C14 0.041(3) 0.055(2) 0.054(3) -0.0101(19) 0.007(2) -0.004(2) C141 0.046(3) 0.055(2) 0.057(2) -0.0018(18) 0.001(2) -0.001(2) C142 0.048(3) 0.067(3) 0.061(3) -0.006(2) -0.002(2) -0.009(2) C143 0.057(3) 0.066(3) 0.063(3) -0.010(2) -0.012(2) -0.005(2) C144 0.053(3) 0.064(3) 0.069(3) -0.013(2) 0.000(2) -0.005(2) C145 0.075(4) 0.074(3) 0.079(3) -0.013(2) -0.002(3) 0.008(3) C146 0.099(5) 0.078(3) 0.086(4) -0.022(3) 0.001(3) 0.019(3) C15 0.058(3) 0.052(2) 0.051(2) -0.0045(18) 0.007(2) 0.004(2) C16 0.060(3) 0.052(2) 0.057(3) -0.007(2) 0.012(2) -0.008(2) C17 0.047(3) 0.055(2) 0.059(3) -0.016(2) 0.010(2) -0.006(2) C171 0.050(3) 0.061(2) 0.056(2) -0.0125(19) 0.006(2) -0.005(2) C172 0.053(3) 0.056(2) 0.064(3) -0.0137(19) 0.002(2) -0.006(2) C173 0.061(3) 0.061(3) 0.064(3) -0.015(2) 0.006(2) -0.008(2) C174 0.067(3) 0.064(3) 0.074(3) -0.012(2) 0.010(2) -0.019(2) C175 0.086(4) 0.077(3) 0.080(3) -0.016(2) 0.018(3) -0.021(3) C176 0.111(5) 0.080(3) 0.077(3) -0.008(3) 0.022(3) -0.029(3) C18 0.049(3) 0.046(2) 0.051(2) -0.0110(18) 0.012(2) -0.002(2) C19 0.032(3) 0.058(2) 0.057(3) -0.0176(19) 0.010(2) -0.0021(19) N20 0.034(2) 0.050(2) 0.048(2) -0.0112(17) 0.0093(18) -0.0039(17) C20 0.034(2) 0.050(2) 0.048(2) -0.0112(17) 0.0093(18) -0.0039(17) _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 N1 C9 1.349(5) . ? N1 C2 1.365(5) . ? N1 H1 0.8600 . ? C2 C20 1.329(5) 2_666 ? C2 N20 1.329(5) 2_666 ? C2 C3 1.477(6) . ? C3 C8 1.411(5) . ? C3 C4 1.421(6) . ? C4 C5 1.375(6) . ? C4 C41 1.503(6) . ? C41 C42 1.514(6) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.512(6) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.521(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.503(6) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.509(6) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C5 C6 1.396(6) . ? C5 H5 0.9300 . ? C6 C7 1.379(6) . ? C6 H6 0.9300 . ? C7 C8 1.422(6) . ? C7 C71 1.519(6) . ? C71 C72 1.521(6) . ? C71 H71A 0.9700 . ? C71 H71B 0.9700 . ? C72 C73 1.525(6) . ? C72 H72A 0.9700 . ? C72 H72B 0.9700 . ? C73 C74 1.521(7) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C74 C75 1.521(6) . ? C74 H74A 0.9700 . ? C74 H74B 0.9700 . ? C75 C76 1.507(7) . ? C75 H75A 0.9700 . ? C75 H75B 0.9700 . ? C76 H76A 0.9600 . ? C76 H76B 0.9600 . ? C76 H76C 0.9600 . ? C8 C9 1.455(6) . ? C9 N10 1.332(5) . ? N10 C12 1.350(6) . ? N11 C12 1.358(6) . ? N11 C19 1.369(5) . ? C12 C13 1.483(5) . ? C13 C14 1.402(6) . ? C13 C18 1.426(6) . ? C14 C15 1.384(6) . ? C14 C141 1.501(6) . ? C141 C142 1.526(6) . ? C141 H14A 0.9700 . ? C141 H14B 0.9700 . ? C142 C143 1.513(6) . ? C142 H14C 0.9700 . ? C142 H14D 0.9700 . ? C143 C144 1.519(6) . ? C143 H14E 0.9700 . ? C143 H14F 0.9700 . ? C144 C145 1.492(6) . ? C144 H14G 0.9700 . ? C144 H14H 0.9700 . ? C145 C146 1.547(6) . ? C145 H14I 0.9700 . ? C145 H14J 0.9700 . ? C146 H14K 0.9600 . ? C146 H14L 0.9600 . ? C146 H14M 0.9600 . ? C15 C16 1.395(6) . ? C15 H15 0.9300 . ? C16 C17 1.386(6) . ? C16 H16 0.9300 . ? C17 C18 1.406(5) . ? C17 C171 1.521(6) . ? C171 C172 1.531(5) . ? C171 H17A 0.9700 . ? C171 H17B 0.9700 . ? C172 C173 1.529(6) . ? C172 H17C 0.9700 . ? C172 H17D 0.9700 . ? C173 C174 1.520(6) . ? C173 H17E 0.9700 . ? C173 H17F 0.9700 . ? C174 C175 1.487(6) . ? C174 H17G 0.9700 . ? C174 H17H 0.9700 . ? C175 C176 1.526(6) . ? C175 H17I 0.9700 . ? C175 H17J 0.9700 . ? C176 H17K 0.9600 . ? C176 H17L 0.9600 . ? C176 H17M 0.9600 . ? C18 C19 1.461(6) . ? C19 C20 1.365(6) . ? C19 N20 1.365(6) . ? N20 C2 1.329(5) 2_666 ? C20 C2 1.329(5) 2_666 ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C2 114.8(4) . . ? C9 N1 H1 122.6 . . ? C2 N1 H1 122.6 . . ? C20 C2 N20 0.001(1) 2_666 2_666 ? C20 C2 N1 128.7(4) 2_666 . ? N20 C2 N1 128.7(4) 2_666 . ? C20 C2 C3 126.7(4) 2_666 . ? N20 C2 C3 126.7(4) 2_666 . ? N1 C2 C3 104.6(4) . . ? C8 C3 C4 121.9(4) . . ? C8 C3 C2 107.2(4) . . ? C4 C3 C2 130.9(4) . . ? C5 C4 C3 115.3(4) . . ? C5 C4 C41 122.1(4) . . ? C3 C4 C41 122.6(4) . . ? C4 C41 C42 117.1(4) . . ? C4 C41 H41A 108.0 . . ? C42 C41 H41A 108.0 . . ? C4 C41 H41B 108.0 . . ? C42 C41 H41B 108.0 . . ? H41A C41 H41B 107.3 . . ? C43 C42 C41 113.0(4) . . ? C43 C42 H42A 109.0 . . ? C41 C42 H42A 109.0 . . ? C43 C42 H42B 109.0 . . ? C41 C42 H42B 109.0 . . ? H42A C42 H42B 107.8 . . ? C42 C43 C44 115.9(4) . . ? C42 C43 H43A 108.3 . . ? C44 C43 H43A 108.3 . . ? C42 C43 H43B 108.3 . . ? C44 C43 H43B 108.3 . . ? H43A C43 H43B 107.4 . . ? C45 C44 C43 113.8(4) . . ? C45 C44 H44A 108.8 . . ? C43 C44 H44A 108.8 . . ? C45 C44 H44B 108.8 . . ? C43 C44 H44B 108.8 . . ? H44A C44 H44B 107.7 . . ? C44 C45 C46 114.1(4) . . ? C44 C45 H45A 108.7 . . ? C46 C45 H45A 108.7 . . ? C44 C45 H45B 108.7 . . ? C46 C45 H45B 108.7 . . ? H45A C45 H45B 107.6 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C4 C5 C6 123.4(4) . . ? C4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C7 C6 C5 122.3(4) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C6 C7 C8 116.1(4) . . ? C6 C7 C71 122.2(4) . . ? C8 C7 C71 121.7(4) . . ? C7 C71 C72 116.5(4) . . ? C7 C71 H71A 108.2 . . ? C72 C71 H71A 108.2 . . ? C7 C71 H71B 108.2 . . ? C72 C71 H71B 108.2 . . ? H71A C71 H71B 107.3 . . ? C71 C72 C73 111.3(4) . . ? C71 C72 H72A 109.4 . . ? C73 C72 H72A 109.4 . . ? C71 C72 H72B 109.4 . . ? C73 C72 H72B 109.4 . . ? H72A C72 H72B 108.0 . . ? C74 C73 C72 114.5(4) . . ? C74 C73 H73A 108.6 . . ? C72 C73 H73A 108.6 . . ? C74 C73 H73B 108.6 . . ? C72 C73 H73B 108.6 . . ? H73A C73 H73B 107.6 . . ? C75 C74 C73 113.1(4) . . ? C75 C74 H74A 109.0 . . ? C73 C74 H74A 109.0 . . ? C75 C74 H74B 109.0 . . ? C73 C74 H74B 109.0 . . ? H74A C74 H74B 107.8 . . ? C76 C75 C74 112.9(4) . . ? C76 C75 H75A 109.0 . . ? C74 C75 H75A 109.0 . . ? C76 C75 H75B 109.0 . . ? C74 C75 H75B 109.0 . . ? H75A C75 H75B 107.8 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C3 C8 C7 120.9(4) . . ? C3 C8 C9 107.6(4) . . ? C7 C8 C9 131.5(4) . . ? N10 C9 N1 128.8(4) . . ? N10 C9 C8 125.3(4) . . ? N1 C9 C8 105.8(3) . . ? C9 N10 C12 124.2(4) . . ? C12 N11 C19 107.6(3) . . ? N10 C12 N11 127.7(3) . . ? N10 C12 C13 121.2(4) . . ? N11 C12 C13 110.9(4) . . ? C14 C13 C18 121.9(3) . . ? C14 C13 C12 133.4(4) . . ? C18 C13 C12 104.7(4) . . ? C15 C14 C13 115.4(4) . . ? C15 C14 C141 119.4(4) . . ? C13 C14 C141 125.1(3) . . ? C14 C141 C142 112.9(4) . . ? C14 C141 H14A 109.0 . . ? C142 C141 H14A 109.0 . . ? C14 C141 H14B 109.0 . . ? C142 C141 H14B 109.0 . . ? H14A C141 H14B 107.8 . . ? C143 C142 C141 114.2(4) . . ? C143 C142 H14C 108.7 . . ? C141 C142 H14C 108.7 . . ? C143 C142 H14D 108.7 . . ? C141 C142 H14D 108.7 . . ? H14C C142 H14D 107.6 . . ? C142 C143 C144 114.3(4) . . ? C142 C143 H14E 108.7 . . ? C144 C143 H14E 108.7 . . ? C142 C143 H14F 108.7 . . ? C144 C143 H14F 108.7 . . ? H14E C143 H14F 107.6 . . ? C145 C144 C143 114.9(4) . . ? C145 C144 H14G 108.6 . . ? C143 C144 H14G 108.6 . . ? C145 C144 H14H 108.6 . . ? C143 C144 H14H 108.6 . . ? H14G C144 H14H 107.5 . . ? C144 C145 C146 113.5(4) . . ? C144 C145 H14I 108.9 . . ? C146 C145 H14I 108.9 . . ? C144 C145 H14J 108.9 . . ? C146 C145 H14J 108.9 . . ? H14I C145 H14J 107.7 . . ? C145 C146 H14K 109.5 . . ? C145 C146 H14L 109.5 . . ? H14K C146 H14L 109.5 . . ? C145 C146 H14M 109.5 . . ? H14K C146 H14M 109.5 . . ? H14L C146 H14M 109.5 . . ? C14 C15 C16 123.1(4) . . ? C14 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C17 C16 C15 122.2(4) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 116.3(4) . . ? C16 C17 C171 121.2(4) . . ? C18 C17 C171 122.5(4) . . ? C17 C171 C172 117.0(4) . . ? C17 C171 H17A 108.1 . . ? C172 C171 H17A 108.1 . . ? C17 C171 H17B 108.1 . . ? C172 C171 H17B 108.1 . . ? H17A C171 H17B 107.3 . . ? C173 C172 C171 116.1(3) . . ? C173 C172 H17C 108.3 . . ? C171 C172 H17C 108.3 . . ? C173 C172 H17D 108.3 . . ? C171 C172 H17D 108.3 . . ? H17C C172 H17D 107.4 . . ? C174 C173 C172 112.1(3) . . ? C174 C173 H17E 109.2 . . ? C172 C173 H17E 109.2 . . ? C174 C173 H17F 109.2 . . ? C172 C173 H17F 109.2 . . ? H17E C173 H17F 107.9 . . ? C175 C174 C173 114.8(4) . . ? C175 C174 H17G 108.6 . . ? C173 C174 H17G 108.6 . . ? C175 C174 H17H 108.6 . . ? C173 C174 H17H 108.6 . . ? H17G C174 H17H 107.6 . . ? C174 C175 C176 112.9(4) . . ? C174 C175 H17I 109.0 . . ? C176 C175 H17I 109.0 . . ? C174 C175 H17J 109.0 . . ? C176 C175 H17J 109.0 . . ? H17I C175 H17J 107.8 . . ? C175 C176 H17K 109.5 . . ? C175 C176 H17L 109.5 . . ? H17K C176 H17L 109.5 . . ? C175 C176 H17M 109.5 . . ? H17K C176 H17M 109.5 . . ? H17L C176 H17M 109.5 . . ? C17 C18 C13 120.8(4) . . ? C17 C18 C19 133.3(4) . . ? C13 C18 C19 105.8(3) . . ? C20 C19 N20 0.0(2) . . ? C20 C19 N11 126.0(4) . . ? N20 C19 N11 126.0(4) . . ? C20 C19 C18 123.0(4) . . ? N20 C19 C18 123.0(4) . . ? N11 C19 C18 110.9(4) . . ? C2 N20 C19 126.6(4) 2_666 . ? C2 C20 C19 126.6(4) 2_666 . ? C2 C20 H20 116.7 2_666 . ? C19 C20 H20 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 C20 178.2(3) . . . 2_666 ? C9 N1 C2 N20 178.2(3) . . . 2_666 ? C9 N1 C2 C3 -2.6(4) . . . . ? C20 C2 C3 C8 -179.2(3) 2_666 . . . ? N20 C2 C3 C8 -179.2(3) 2_666 . . . ? N1 C2 C3 C8 1.7(4) . . . . ? C20 C2 C3 C4 1.6(6) 2_666 . . . ? N20 C2 C3 C4 1.6(6) 2_666 . . . ? N1 C2 C3 C4 -177.6(4) . . . . ? C8 C3 C4 C5 -2.6(5) . . . . ? C2 C3 C4 C5 176.6(4) . . . . ? C8 C3 C4 C41 176.0(3) . . . . ? C2 C3 C4 C41 -4.8(6) . . . . ? C5 C4 C41 C42 3.4(5) . . . . ? C3 C4 C41 C42 -175.1(3) . . . . ? C4 C41 C42 C43 177.0(3) . . . . ? C41 C42 C43 C44 -175.7(3) . . . . ? C42 C43 C44 C45 -178.6(3) . . . . ? C43 C44 C45 C46 -177.5(3) . . . . ? C3 C4 C5 C6 2.6(5) . . . . ? C41 C4 C5 C6 -176.0(4) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C8 -2.7(5) . . . . ? C5 C6 C7 C71 176.9(3) . . . . ? C6 C7 C71 C72 -0.8(5) . . . . ? C8 C7 C71 C72 178.7(3) . . . . ? C7 C71 C72 C73 179.5(3) . . . . ? C71 C72 C73 C74 -175.5(3) . . . . ? C72 C73 C74 C75 173.6(3) . . . . ? C73 C74 C75 C76 -174.7(4) . . . . ? C4 C3 C8 C7 0.0(5) . . . . ? C2 C3 C8 C7 -179.3(3) . . . . ? C4 C3 C8 C9 179.0(3) . . . . ? C2 C3 C8 C9 -0.3(4) . . . . ? C6 C7 C8 C3 2.6(5) . . . . ? C71 C7 C8 C3 -177.0(3) . . . . ? C6 C7 C8 C9 -176.1(4) . . . . ? C71 C7 C8 C9 4.3(6) . . . . ? C2 N1 C9 N10 -178.7(4) . . . . ? C2 N1 C9 C8 2.4(4) . . . . ? C3 C8 C9 N10 179.9(3) . . . . ? C7 C8 C9 N10 -1.2(6) . . . . ? C3 C8 C9 N1 -1.2(4) . . . . ? C7 C8 C9 N1 177.7(4) . . . . ? N1 C9 N10 C12 -2.8(6) . . . . ? C8 C9 N10 C12 175.8(3) . . . . ? C9 N10 C12 N11 -1.0(6) . . . . ? C9 N10 C12 C13 -176.2(3) . . . . ? C19 N11 C12 N10 -175.1(4) . . . . ? C19 N11 C12 C13 0.4(4) . . . . ? N10 C12 C13 C14 -6.0(6) . . . . ? N11 C12 C13 C14 178.2(4) . . . . ? N10 C12 C13 C18 173.8(3) . . . . ? N11 C12 C13 C18 -2.1(4) . . . . ? C18 C13 C14 C15 -5.4(5) . . . . ? C12 C13 C14 C15 174.3(4) . . . . ? C18 C13 C14 C141 172.5(4) . . . . ? C12 C13 C14 C141 -7.8(7) . . . . ? C15 C14 C141 C142 71.4(5) . . . . ? C13 C14 C141 C142 -106.4(4) . . . . ? C14 C141 C142 C143 67.4(5) . . . . ? C141 C142 C143 C144 -176.4(3) . . . . ? C142 C143 C144 C145 -176.6(4) . . . . ? C143 C144 C145 C146 -175.7(4) . . . . ? C13 C14 C15 C16 1.8(6) . . . . ? C141 C14 C15 C16 -176.2(4) . . . . ? C14 C15 C16 C17 1.2(6) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C15 C16 C17 C171 -179.3(4) . . . . ? C16 C17 C171 C172 8.8(5) . . . . ? C18 C17 C171 C172 -169.8(3) . . . . ? C17 C171 C172 C173 -81.0(5) . . . . ? C171 C172 C173 C174 171.8(4) . . . . ? C172 C173 C174 C175 -178.3(4) . . . . ? C173 C174 C175 C176 171.7(5) . . . . ? C16 C17 C18 C13 -3.0(5) . . . . ? C171 C17 C18 C13 175.7(4) . . . . ? C16 C17 C18 C19 -178.1(4) . . . . ? C171 C17 C18 C19 0.6(6) . . . . ? C14 C13 C18 C17 6.2(5) . . . . ? C12 C13 C18 C17 -173.6(3) . . . . ? C14 C13 C18 C19 -177.5(3) . . . . ? C12 C13 C18 C19 2.7(4) . . . . ? C12 N11 C19 C20 -176.2(3) . . . . ? C12 N11 C19 N20 -176.2(3) . . . . ? C12 N11 C19 C18 1.4(4) . . . . ? C17 C18 C19 C20 -9.4(6) . . . . ? C13 C18 C19 C20 175.0(3) . . . . ? C17 C18 C19 N20 -9.4(6) . . . . ? C13 C18 C19 N20 175.0(3) . . . . ? C17 C18 C19 N11 172.9(4) . . . . ? C13 C18 C19 N11 -2.7(4) . . . . ? C20 C19 N20 C2 0(27) . . . 2_666 ? N11 C19 N20 C2 -2.5(6) . . . 2_666 ? C18 C19 N20 C2 -179.8(3) . . . 2_666 ? N20 C19 C20 C2 0(27) . . . 2_666 ? N11 C19 C20 C2 -2.5(6) . . . 2_666 ? C18 C19 C20 C2 -179.8(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 22.00 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.225 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.060