Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Kenneth Warnmark' _publ_contact_author_address ; Department of Chemistry Organic Chemistry 1 Lund University PO Box 124 Lund 22100 SWEDEN ; _publ_contact_author_email KENNETH.WARNMARK@ORGK1.LU.SE _publ_section_title ; Synthesis of 2-Pyridone-fused 2,2'-Bipyridine Derivatives. An Unexpectedly Complex Solid State Structure of 3,6-Dimethyl-9H-4,5,9-triazaphenanthren-10-one ; loop_ _publ_author_name 'Kenneth Warnmark' 'Carlos Solano Arribas' 'Stefan Jonsson' 'Jay S. Siegel' 'Ola F. Wendt' data_sad2 _database_code_depnum_ccdc_archive 'CCDC 256289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9.43 N3 O' _chemical_formula_weight 223.66 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.057(2) _cell_length_b 13.722(3) _cell_length_c 15.423(3) _cell_angle_alpha 72.17(3) _cell_angle_beta 80.39(3) _cell_angle_gamma 86.90(3) _cell_volume 1997.7(7) _cell_formula_units_Z 7 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4360 _cell_measurement_theta_min 2.298 _cell_measurement_theta_max 26.378 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 1.02 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 815 _exptl_absorpt_coefficient_mu 0.086 _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 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21513 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 31.17 _reflns_number_total 11415 _reflns_number_gt 4583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (Brandenburg)' _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^ > 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. Atomic coordinates from an initial structure refinement were imported into A molecular mechanics program where the lowest energy orientation of one molecular unit inside the rigid, porous lattice created by the three well- resolved molecules was determined. The atomic coordinates of the resulting model (excluding hydrogen atoms) were reapplied to the structure refinement to represent the disordered molecule, using a FRAG/FEND instruction, and the position of the whole molecule was refined. The isotropic U factors for this molecule were restrained using a SIMU instruction. ; _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^)+(0.1500P)^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 11415 _refine_ls_number_parameters 490 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.2038 _refine_ls_R_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.3289 _refine_ls_wR_factor_gt 0.2830 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.161 _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 N5B N 0.7940(2) 0.56909(18) 0.22733(16) 0.0466(6) Uani 1 1 d . . . N4B N 0.5778(2) 0.60479(19) 0.34954(17) 0.0518(6) Uani 1 1 d . . . N4A N 0.3281(2) 0.58063(19) 0.02912(16) 0.0502(6) Uani 1 1 d . . . C13B C 0.8129(3) 0.6297(2) 0.27890(19) 0.0426(7) Uani 1 1 d . . . C14B C 0.9378(3) 0.6739(2) 0.2727(2) 0.0497(7) Uani 1 1 d . . . C12A C 0.3834(3) 0.5144(2) 0.09826(19) 0.0452(7) Uani 1 1 d . . . C12B C 0.6994(3) 0.6456(2) 0.3453(2) 0.0464(7) Uani 1 1 d . . . C13A C 0.3505(3) 0.4056(2) 0.12769(19) 0.0459(7) Uani 1 1 d . . . N4C N 0.7666(3) 0.9327(2) 0.48591(19) 0.0566(7) Uani 1 1 d . . . N10B N 0.8462(3) 0.7448(2) 0.39492(19) 0.0609(7) Uani 1 1 d . . . H10B H 0.8545 0.7805 0.4308 0.073 Uiso 1 1 calc R . . N10A N 0.5297(3) 0.4778(2) 0.21515(19) 0.0641(8) Uani 1 1 d . . . H10A H 0.5820 0.5019 0.2423 0.077 Uiso 1 1 calc R . . C11B C 0.7208(3) 0.7017(2) 0.4034(2) 0.0497(7) Uani 1 1 d . . . C12C C 0.8365(3) 0.9380(2) 0.5526(2) 0.0493(7) Uani 1 1 d . . . N5A N 0.2602(3) 0.3733(2) 0.08578(17) 0.0566(7) Uani 1 1 d . . . C9B C 0.9558(3) 0.7348(2) 0.3344(2) 0.0584(8) Uani 1 1 d . . . N5C N 0.9204(3) 0.7673(2) 0.56878(18) 0.0570(7) Uani 1 1 d . . . C11A C 0.4738(3) 0.5469(2) 0.1445(2) 0.0512(8) Uani 1 1 d . . . C6B C 0.8997(3) 0.5518(2) 0.16812(19) 0.0512(7) Uani 1 1 d . . . O1B O 1.0688(2) 0.77213(19) 0.3313(2) 0.0816(8) Uani 1 1 d . . . C14A C 0.4110(3) 0.3379(2) 0.1993(2) 0.0531(8) Uani 1 1 d . . . C1B C 0.6146(4) 0.7105(3) 0.4716(2) 0.0659(9) Uani 1 1 d . . . H1B H 0.6264 0.7448 0.5133 0.079 Uiso 1 1 calc R . . N10C N 0.9098(3) 1.0307(2) 0.6471(2) 0.0694(8) Uani 1 1 d . . . H10C H 0.9047 1.0857 0.6632 0.083 Uiso 1 1 calc R . . C7B C 1.0257(3) 0.5950(3) 0.1580(2) 0.0650(9) Uani 1 1 d . . . H7B H 1.0964 0.5824 0.1155 0.078 Uiso 1 1 calc R . . C13C C 0.9192(3) 0.8531(2) 0.5938(2) 0.0516(8) Uani 1 1 d . . . C1A C 0.5057(3) 0.6504(3) 0.1170(3) 0.0671(10) Uani 1 1 d . . . H1A H 0.5645 0.6744 0.1463 0.081 Uiso 1 1 calc R . . C11C C 0.8352(3) 1.0270(3) 0.5804(2) 0.0578(8) Uani 1 1 d . . . C3A C 0.3595(3) 0.6790(2) 0.0036(2) 0.0543(8) Uani 1 1 d . . . O1A O 0.5660(3) 0.3171(2) 0.30609(19) 0.0874(8) Uani 1 1 d . . . C8B C 1.0462(3) 0.6557(3) 0.2101(2) 0.0620(9) Uani 1 1 d . . . H8B H 1.1303 0.6843 0.2039 0.074 Uiso 1 1 calc R . . C3B C 0.4752(3) 0.6165(3) 0.4127(2) 0.0609(9) Uani 1 1 d . . . C14C C 0.9955(4) 0.8617(3) 0.6606(2) 0.0624(9) Uani 1 1 d . . . O1C O 1.0568(3) 0.9631(2) 0.7476(2) 0.1074(10) Uani 1 1 d . . . C7A C 0.2944(4) 0.2028(3) 0.1816(3) 0.0741(10) Uani 1 1 d . . . H7A H 0.2740 0.1336 0.1980 0.089 Uiso 1 1 calc R . . C2A C 0.4495(4) 0.7166(3) 0.0462(3) 0.0660(9) Uani 1 1 d . . . H2A H 0.4708 0.7858 0.0265 0.079 Uiso 1 1 calc R . . C6A C 0.2351(4) 0.2731(3) 0.1121(3) 0.0666(9) Uani 1 1 d . . . C1C C 0.7564(4) 1.1098(3) 0.5406(3) 0.0698(10) Uani 1 1 d . . . H1C H 0.7513 1.1688 0.5587 0.084 Uiso 1 1 calc R . . C9A C 0.5088(3) 0.3755(3) 0.2450(2) 0.0617(9) Uani 1 1 d . . . C16B C 0.8755(4) 0.4819(3) 0.1128(2) 0.0667(9) Uani 1 1 d . . . H16A H 0.8050 0.4344 0.1472 0.100 Uiso 1 1 calc R . . H16B H 0.9568 0.4450 0.1009 0.100 Uiso 1 1 calc R . . H16C H 0.8493 0.5221 0.0554 0.100 Uiso 1 1 calc R . . C2B C 0.4936(4) 0.6679(3) 0.4761(3) 0.0677(9) Uani 1 1 d . . . H2B H 0.4222 0.6727 0.5215 0.081 Uiso 1 1 calc R . . C3C C 0.6933(3) 1.0131(3) 0.4469(3) 0.0638(9) Uani 1 1 d . . . C9C C 0.9910(4) 0.9536(3) 0.6892(2) 0.0704(10) Uani 1 1 d . . . C8A C 0.3809(4) 0.2348(3) 0.2250(2) 0.0676(9) Uani 1 1 d . . . H8A H 0.4199 0.1883 0.2717 0.081 Uiso 1 1 calc R . . C15A C 0.2918(4) 0.7500(3) -0.0719(3) 0.0760(10) Uani 1 1 d . . . H15A H 0.3191 0.7325 -0.1280 0.114 Uiso 1 1 calc R . . H15B H 0.3174 0.8193 -0.0813 0.114 Uiso 1 1 calc R . . H15C H 0.1957 0.7435 -0.0546 0.114 Uiso 1 1 calc R . . C6C C 0.9990(4) 0.6882(3) 0.6055(2) 0.0689(10) Uani 1 1 d . . . C8C C 1.0804(4) 0.7797(3) 0.6960(3) 0.0826(12) Uani 1 1 d . . . H8C H 1.1338 0.7833 0.7387 0.099 Uiso 1 1 calc R . . C15B C 0.3409(3) 0.5729(3) 0.4126(3) 0.0798(11) Uani 1 1 d . . . H15D H 0.3545 0.5209 0.3822 0.120 Uiso 1 1 calc R . . H15E H 0.2854 0.6265 0.3804 0.120 Uiso 1 1 calc R . . H15F H 0.2971 0.5437 0.4750 0.120 Uiso 1 1 calc R . . C15C C 0.6232(4) 1.0047(3) 0.3707(3) 0.0855(12) Uani 1 1 d . . . H15G H 0.6017 0.9343 0.3809 0.128 Uiso 1 1 calc R . . H15H H 0.6813 1.0299 0.3126 0.128 Uiso 1 1 calc R . . H15I H 0.5416 1.0445 0.3698 0.128 Uiso 1 1 calc R . . C2C C 0.6864(4) 1.1021(3) 0.4736(3) 0.0769(11) Uani 1 1 d . . . H2C H 0.6337 1.1569 0.4457 0.092 Uiso 1 1 calc R . . C7C C 1.0843(4) 0.6942(3) 0.6673(3) 0.0823(12) Uani 1 1 d . . . H7C H 1.1428 0.6406 0.6885 0.099 Uiso 1 1 calc R . . C16C C 0.9949(5) 0.5948(3) 0.5760(3) 0.0958(14) Uani 1 1 d . . . H16D H 1.0035 0.6140 0.5100 0.144 Uiso 1 1 calc R . . H16E H 0.9106 0.5601 0.6031 0.144 Uiso 1 1 calc R . . H16F H 1.0678 0.5499 0.5959 0.144 Uiso 1 1 calc R . . C16A C 0.1370(5) 0.2396(3) 0.0610(3) 0.1000(15) Uani 1 1 d . . . H16G H 0.1020 0.2990 0.0194 0.150 Uiso 1 1 calc R . . H16H H 0.0640 0.2021 0.1047 0.150 Uiso 1 1 calc R . . H16I H 0.1834 0.1968 0.0266 0.150 Uiso 1 1 calc R . . C12D C 0.3943(7) 0.9793(6) 0.0481(5) 0.269(11) Uiso 0.481(3) 1 d PGU A -1 C11D C 0.2878(7) 0.9286(6) 0.1148(6) 0.176(6) Uiso 0.481(3) 1 d PGU A -1 C1D C 0.1571(7) 0.9342(7) 0.0947(7) 0.182(7) Uiso 0.481(3) 1 d PGU A -1 C2D C 0.1336(8) 0.9905(8) 0.0073(8) 0.55(3) Uiso 0.481(3) 1 d PGU A -1 C3D C 0.2417(10) 1.0404(10) -0.0558(7) 0.64(3) Uiso 0.481(3) 1 d PGU A -1 N4D N 0.3689(9) 1.0344(9) -0.0364(6) 0.61(3) Uiso 0.481(3) 1 d PGU A -1 C7D C 0.7860(7) 0.9497(9) 0.1119(7) 0.194(7) Uiso 0.481(3) 1 d PGU A -1 C6D C 0.7586(8) 1.0036(10) 0.0250(7) 0.264(11) Uiso 0.481(3) 1 d PGU A -1 N5D N 0.6317(8) 1.0138(9) 0.0043(6) 0.385(15) Uiso 0.481(3) 1 d PGU A -1 C13D C 0.5252(7) 0.9701(6) 0.0691(5) 0.182(6) Uiso 0.481(3) 1 d PGU A -1 C14D C 0.5483(7) 0.9145(5) 0.1576(5) 0.149(5) Uiso 0.481(3) 1 d PGU A -1 C8D C 0.6791(8) 0.9044(6) 0.1791(6) 0.147(5) Uiso 0.481(3) 1 d PGU A -1 N10D N 0.3108(8) 0.8712(6) 0.2029(5) 0.229(7) Uiso 0.481(3) 1 d PGU A -1 C9D C 0.4349(8) 0.8653(6) 0.2293(5) 0.147(5) Uiso 0.481(3) 1 d PGU A -1 O1D O 0.4508(11) 0.8222(8) 0.3089(5) 0.483(18) Uiso 0.481(3) 1 d PGU A -1 C15D C 0.2242(13) 1.1023(13) -0.1513(8) 0.212(8) Uiso 0.481(3) 1 d PGU A -1 C16D C 0.8702(9) 1.0548(14) -0.0502(8) 0.41(2) Uiso 0.481(3) 1 d PGU A -1 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 N5B 0.0469(14) 0.0528(15) 0.0459(13) -0.0212(11) -0.0102(11) -0.0040(11) N4B 0.0438(14) 0.0579(16) 0.0607(16) -0.0274(12) -0.0088(12) -0.0021(12) N4A 0.0469(14) 0.0556(16) 0.0508(14) -0.0185(12) -0.0094(12) -0.0044(12) C13B 0.0431(16) 0.0418(16) 0.0484(16) -0.0182(12) -0.0132(13) -0.0011(12) C14B 0.0482(17) 0.0469(17) 0.0590(18) -0.0201(14) -0.0117(15) -0.0075(13) C12A 0.0378(15) 0.0541(18) 0.0475(16) -0.0213(14) -0.0047(13) -0.0046(13) C12B 0.0462(17) 0.0452(16) 0.0529(17) -0.0216(13) -0.0075(14) -0.0045(13) C13A 0.0379(15) 0.0567(19) 0.0449(16) -0.0182(13) -0.0038(12) -0.0078(13) N4C 0.0519(15) 0.0540(16) 0.0692(17) -0.0242(13) -0.0133(13) -0.0008(13) N10B 0.0646(18) 0.0618(17) 0.0738(18) -0.0410(14) -0.0182(15) -0.0080(14) N10A 0.0641(17) 0.068(2) 0.0727(18) -0.0281(15) -0.0320(15) -0.0027(14) C11B 0.0528(18) 0.0452(17) 0.0571(18) -0.0243(14) -0.0074(15) -0.0033(14) C12C 0.0485(17) 0.0482(17) 0.0554(17) -0.0231(14) -0.0020(14) -0.0102(14) N5A 0.0579(16) 0.0564(17) 0.0604(16) -0.0203(13) -0.0131(13) -0.0151(13) C9B 0.055(2) 0.0504(19) 0.081(2) -0.0316(17) -0.0167(18) -0.0075(15) N5C 0.0652(17) 0.0510(16) 0.0578(16) -0.0192(12) -0.0111(13) -0.0063(13) C11A 0.0417(16) 0.061(2) 0.0602(19) -0.0300(16) -0.0115(14) -0.0036(14) C6B 0.0507(18) 0.063(2) 0.0414(16) -0.0173(14) -0.0082(14) -0.0012(15) O1B 0.0629(15) 0.0777(17) 0.126(2) -0.0562(16) -0.0204(15) -0.0186(13) C14A 0.0451(17) 0.061(2) 0.0531(18) -0.0161(15) -0.0083(14) -0.0042(15) C1B 0.076(2) 0.063(2) 0.070(2) -0.0376(18) -0.0085(19) 0.0003(18) N10C 0.076(2) 0.070(2) 0.0768(19) -0.0452(16) -0.0027(16) -0.0215(16) C7B 0.0492(19) 0.085(3) 0.063(2) -0.0305(19) 0.0016(16) -0.0061(17) C13C 0.0532(18) 0.0520(19) 0.0490(17) -0.0160(14) -0.0012(14) -0.0120(15) C1A 0.062(2) 0.063(2) 0.091(3) -0.0349(19) -0.026(2) -0.0098(17) C11C 0.0559(19) 0.058(2) 0.065(2) -0.0303(16) 0.0047(16) -0.0169(16) C3A 0.0514(18) 0.0504(19) 0.0637(19) -0.0225(15) -0.0058(15) -0.0014(15) O1A 0.0960(19) 0.0873(19) 0.0859(18) -0.0171(14) -0.0530(16) 0.0057(15) C8B 0.0459(18) 0.069(2) 0.074(2) -0.0265(18) -0.0035(17) -0.0132(16) C3B 0.052(2) 0.063(2) 0.071(2) -0.0296(17) -0.0046(17) 0.0002(16) C14C 0.073(2) 0.064(2) 0.0501(18) -0.0138(16) -0.0097(17) -0.0160(18) O1C 0.141(3) 0.116(2) 0.089(2) -0.0485(17) -0.0431(19) -0.025(2) C7A 0.074(2) 0.055(2) 0.086(3) -0.0074(19) -0.013(2) -0.0197(18) C2A 0.066(2) 0.055(2) 0.082(2) -0.0243(18) -0.0137(19) -0.0111(17) C6A 0.062(2) 0.066(2) 0.075(2) -0.0212(18) -0.0140(18) -0.0187(17) C1C 0.076(2) 0.051(2) 0.091(3) -0.0364(19) -0.008(2) -0.0018(18) C9A 0.057(2) 0.074(2) 0.060(2) -0.0247(18) -0.0169(17) 0.0016(17) C16B 0.076(2) 0.080(2) 0.0553(19) -0.0391(18) -0.0081(17) 0.0028(19) C2B 0.061(2) 0.069(2) 0.079(2) -0.0385(19) 0.0036(18) 0.0015(18) C3C 0.055(2) 0.058(2) 0.081(2) -0.0242(18) -0.0139(18) -0.0012(17) C9C 0.083(3) 0.075(3) 0.061(2) -0.0269(18) -0.012(2) -0.023(2) C8A 0.062(2) 0.065(2) 0.068(2) -0.0064(17) -0.0133(18) -0.0119(17) C15A 0.077(2) 0.066(2) 0.083(3) -0.0159(19) -0.021(2) 0.0006(19) C6C 0.093(3) 0.047(2) 0.063(2) -0.0082(16) -0.019(2) -0.0028(19) C8C 0.106(3) 0.077(3) 0.065(2) -0.0079(19) -0.038(2) -0.014(2) C15B 0.049(2) 0.092(3) 0.105(3) -0.047(2) 0.006(2) -0.0095(19) C15C 0.086(3) 0.083(3) 0.097(3) -0.026(2) -0.046(2) 0.012(2) C2C 0.066(2) 0.055(2) 0.111(3) -0.031(2) -0.010(2) 0.0053(18) C7C 0.100(3) 0.062(2) 0.083(3) -0.007(2) -0.043(2) 0.005(2) C16C 0.127(4) 0.057(2) 0.110(3) -0.025(2) -0.043(3) 0.014(2) C16A 0.118(4) 0.075(3) 0.124(4) -0.030(2) -0.053(3) -0.036(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N5B C6B 1.342(4) . ? N5B C13B 1.354(3) . ? N4B C3B 1.335(4) . ? N4B C12B 1.355(4) . ? N4A C3A 1.326(4) . ? N4A C12A 1.350(4) . ? C13B C14B 1.401(4) . ? C13B C12B 1.456(4) . ? C14B C8B 1.396(4) . ? C14B C9B 1.482(4) . ? C12A C11A 1.410(4) . ? C12A C13A 1.460(4) . ? C12B C11B 1.395(4) . ? C13A N5A 1.361(3) . ? C13A C14A 1.410(4) . ? N4C C3C 1.333(4) . ? N4C C12C 1.360(4) . ? N10B C9B 1.351(4) . ? N10B C11B 1.392(4) . ? N10B H10B 0.8600 . ? N10A C9A 1.353(4) . ? N10A C11A 1.385(4) . ? N10A H10A 0.8600 . ? C11B C1B 1.397(4) . ? C12C C11C 1.411(4) . ? C12C C13C 1.440(4) . ? N5A C6A 1.334(4) . ? C9B O1B 1.259(4) . ? N5C C6C 1.343(4) . ? N5C C13C 1.346(4) . ? C11A C1A 1.390(4) . ? C6B C7B 1.393(4) . ? C6B C16B 1.517(4) . ? C14A C8A 1.383(5) . ? C14A C9A 1.497(4) . ? C1B C2B 1.361(5) . ? C1B H1B 0.9300 . ? N10C C9C 1.368(5) . ? N10C C11C 1.384(4) . ? N10C H10C 0.8600 . ? C7B C8B 1.365(4) . ? C7B H7B 0.9300 . ? C13C C14C 1.418(4) . ? C1A C2A 1.372(5) . ? C1A H1A 0.9300 . ? C11C C1C 1.391(5) . ? C3A C2A 1.404(4) . ? C3A C15A 1.506(5) . ? O1A C9A 1.237(4) . ? C8B H8B 0.9300 . ? C3B C2B 1.408(5) . ? C3B C15B 1.507(4) . ? C14C C8C 1.403(5) . ? C14C C9C 1.455(5) . ? O1C C9C 1.242(4) . ? C7A C8A 1.347(5) . ? C7A C6A 1.398(5) . ? C7A H7A 0.9300 . ? C2A H2A 0.9300 . ? C6A C16A 1.529(5) . ? C1C C2C 1.375(5) . ? C1C H1C 0.9300 . ? C16B H16A 0.9600 . ? C16B H16B 0.9600 . ? C16B H16C 0.9600 . ? C2B H2B 0.9300 . ? C3C C2C 1.399(5) . ? C3C C15C 1.504(5) . ? C8A H8A 0.9300 . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? C6C C7C 1.407(5) . ? C6C C16C 1.490(5) . ? C8C C7C 1.372(5) . ? C8C H8C 0.9300 . ? C15B H15D 0.9600 . ? C15B H15E 0.9600 . ? C15B H15F 0.9600 . ? C15C H15G 0.9600 . ? C15C H15H 0.9600 . ? C15C H15I 0.9600 . ? C2C H2C 0.9300 . ? C7C H7C 0.9300 . ? C16C H16D 0.9600 . ? C16C H16E 0.9600 . ? C16C H16F 0.9600 . ? C16A H16G 0.9600 . ? C16A H16H 0.9600 . ? C16A H16I 0.9600 . ? C12D N4D 1.3497 . ? C12D C13D 1.3978 . ? C12D C11D 1.4021 . ? C11D C1D 1.3931 . ? C11D N10D 1.3957 . ? C1D C2D 1.3846 . ? C2D C3D 1.3845 . ? C3D N4D 1.3542 . ? C3D C15D 1.4917 . ? C7D C6D 1.3836 . ? C7D C8D 1.3866 . ? C6D N5D 1.3565 . ? C6D C16D 1.4997 . ? N5D C13D 1.3604 . ? C13D C14D 1.3956 . ? C14D C8D 1.3988 . ? C14D C9D 1.4779 . ? N10D C9D 1.3680 . ? C9D O1D 1.2220 . ? 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 C6B N5B C13B 118.1(2) . . ? C3B N4B C12B 119.2(2) . . ? C3A N4A C12A 119.4(2) . . ? N5B C13B C14B 122.4(3) . . ? N5B C13B C12B 118.0(2) . . ? C14B C13B C12B 119.5(2) . . ? C8B C14B C13B 118.6(3) . . ? C8B C14B C9B 120.8(3) . . ? C13B C14B C9B 120.5(3) . . ? N4A C12A C11A 121.8(3) . . ? N4A C12A C13A 120.4(2) . . ? C11A C12A C13A 117.8(3) . . ? N4B C12B C11B 122.4(3) . . ? N4B C12B C13B 119.4(2) . . ? C11B C12B C13B 118.3(3) . . ? N5A C13A C14A 122.2(3) . . ? N5A C13A C12A 118.6(3) . . ? C14A C13A C12A 119.2(2) . . ? C3C N4C C12C 119.1(3) . . ? C9B N10B C11B 124.7(2) . . ? C9B N10B H10B 117.6 . . ? C11B N10B H10B 117.6 . . ? C9A N10A C11A 125.4(3) . . ? C9A N10A H10A 117.3 . . ? C11A N10A H10A 117.3 . . ? N10B C11B C12B 120.5(3) . . ? N10B C11B C1B 121.2(3) . . ? C12B C11B C1B 118.2(3) . . ? N4C C12C C11C 121.7(3) . . ? N4C C12C C13C 120.0(3) . . ? C11C C12C C13C 118.2(3) . . ? C6A N5A C13A 117.3(3) . . ? O1B C9B N10B 122.7(3) . . ? O1B C9B C14B 121.0(3) . . ? N10B C9B C14B 116.3(3) . . ? C6C N5C C13C 119.6(3) . . ? N10A C11A C1A 120.8(3) . . ? N10A C11A C12A 121.0(3) . . ? C1A C11A C12A 118.2(3) . . ? N5B C6B C7B 122.0(3) . . ? N5B C6B C16B 116.6(3) . . ? C7B C6B C16B 121.4(3) . . ? C8A C14A C13A 118.5(3) . . ? C8A C14A C9A 120.3(3) . . ? C13A C14A C9A 121.2(3) . . ? C2B C1B C11B 118.8(3) . . ? C2B C1B H1B 120.6 . . ? C11B C1B H1B 120.6 . . ? C9C N10C C11C 125.0(3) . . ? C9C N10C H10C 117.5 . . ? C11C N10C H10C 117.5 . . ? C8B C7B C6B 120.4(3) . . ? C8B C7B H7B 119.8 . . ? C6B C7B H7B 119.8 . . ? N5C C13C C14C 121.9(3) . . ? N5C C13C C12C 119.0(3) . . ? C14C C13C C12C 119.1(3) . . ? C2A C1A C11A 119.3(3) . . ? C2A C1A H1A 120.4 . . ? C11A C1A H1A 120.4 . . ? N10C C11C C1C 120.9(3) . . ? N10C C11C C12C 120.3(3) . . ? C1C C11C C12C 118.8(3) . . ? N4A C3A C2A 121.8(3) . . ? N4A C3A C15A 117.1(3) . . ? C2A C3A C15A 121.0(3) . . ? C7B C8B C14B 118.4(3) . . ? C7B C8B H8B 120.8 . . ? C14B C8B H8B 120.8 . . ? N4B C3B C2B 120.6(3) . . ? N4B C3B C15B 117.2(3) . . ? C2B C3B C15B 122.2(3) . . ? C8C C14C C13C 117.7(3) . . ? C8C C14C C9C 120.6(3) . . ? C13C C14C C9C 121.7(3) . . ? C8A C7A C6A 120.3(3) . . ? C8A C7A H7A 119.8 . . ? C6A C7A H7A 119.8 . . ? C1A C2A C3A 119.5(3) . . ? C1A C2A H2A 120.2 . . ? C3A C2A H2A 120.2 . . ? N5A C6A C7A 122.6(3) . . ? N5A C6A C16A 115.6(3) . . ? C7A C6A C16A 121.8(3) . . ? C2C C1C C11C 118.2(3) . . ? C2C C1C H1C 120.9 . . ? C11C C1C H1C 120.9 . . ? O1A C9A N10A 122.4(3) . . ? O1A C9A C14A 122.3(3) . . ? N10A C9A C14A 115.3(3) . . ? C6B C16B H16A 109.5 . . ? C6B C16B H16B 109.5 . . ? H16A C16B H16B 109.5 . . ? C6B C16B H16C 109.5 . . ? H16A C16B H16C 109.5 . . ? H16B C16B H16C 109.5 . . ? C1B C2B C3B 120.7(3) . . ? C1B C2B H2B 119.6 . . ? C3B C2B H2B 119.6 . . ? N4C C3C C2C 121.2(3) . . ? N4C C3C C15C 116.8(3) . . ? C2C C3C C15C 121.9(3) . . ? O1C C9C N10C 121.4(3) . . ? O1C C9C C14C 123.0(4) . . ? N10C C9C C14C 115.7(3) . . ? C7A C8A C14A 119.0(3) . . ? C7A C8A H8A 120.5 . . ? C14A C8A H8A 120.5 . . ? C3A C15A H15A 109.5 . . ? C3A C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? C3A C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? N5C C6C C7C 121.4(3) . . ? N5C C6C C16C 117.2(3) . . ? C7C C6C C16C 121.4(4) . . ? C7C C8C C14C 119.7(3) . . ? C7C C8C H8C 120.2 . . ? C14C C8C H8C 120.2 . . ? C3B C15B H15D 109.5 . . ? C3B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C3B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C3C C15C H15G 109.5 . . ? C3C C15C H15H 109.5 . . ? H15G C15C H15H 109.5 . . ? C3C C15C H15I 109.5 . . ? H15G C15C H15I 109.5 . . ? H15H C15C H15I 109.5 . . ? C1C C2C C3C 120.9(4) . . ? C1C C2C H2C 119.5 . . ? C3C C2C H2C 119.5 . . ? C8C C7C C6C 119.5(4) . . ? C8C C7C H7C 120.2 . . ? C6C C7C H7C 120.2 . . ? C6C C16C H16D 109.5 . . ? C6C C16C H16E 109.5 . . ? H16D C16C H16E 109.5 . . ? C6C C16C H16F 109.5 . . ? H16D C16C H16F 109.5 . . ? H16E C16C H16F 109.5 . . ? C6A C16A H16G 109.5 . . ? C6A C16A H16H 109.5 . . ? H16G C16A H16H 109.5 . . ? C6A C16A H16I 109.5 . . ? H16G C16A H16I 109.5 . . ? H16H C16A H16I 109.5 . . ? N4D C12D C13D 121.1 . . ? N4D C12D C11D 119.2 . . ? C13D C12D C11D 119.7 . . ? C1D C11D N10D 118.7 . . ? C1D C11D C12D 120.8 . . ? N10D C11D C12D 120.5 . . ? C2D C1D C11D 119.0 . . ? C3D C2D C1D 118.1 . . ? N4D C3D C2D 122.9 . . ? N4D C3D C15D 116.0 . . ? C2D C3D C15D 121.1 . . ? C12D N4D C3D 120.1 . . ? C6D C7D C8D 118.1 . . ? N5D C6D C7D 122.2 . . ? N5D C6D C16D 117.3 . . ? C7D C6D C16D 120.4 . . ? C6D N5D C13D 120.7 . . ? N5D C13D C14D 119.0 . . ? N5D C13D C12D 121.1 . . ? C14D C13D C12D 119.9 . . ? C13D C14D C8D 120.3 . . ? C13D C14D C9D 120.3 . . ? C8D C14D C9D 119.4 . . ? C7D C8D C14D 119.7 . . ? C9D N10D C11D 122.3 . . ? O1D C9D N10D 121.4 . . ? O1D C9D C14D 121.6 . . ? N10D C9D C14D 117.0 . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 31.17 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.847 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.082