# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Vladimir B. Arion' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Anatolie Dobrov' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Simone Goeschl' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Michael A. Jakupec' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Bernhard K. Keppler' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Peter Rapta' ; Department of Physical Chemistry, Slovak University of Technology Radlinskeho 9 SK-81237 Bratislava Slovak Republic ; _publ_section_title ; Ruthenium(II)- and osmium(II)-arene-based paullones bearing a TEMPO free-radical unit as potential anticancer drugs ; _publ_contact_author_name 'Vladimir Arion' _publ_contact_author_email vladimir.arion@univie.ac.at data_ANDO862 _database_code_depnum_ccdc_archive 'CCDC 883609' #TrackingRef '- ANDO862.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-amino-2,2,6,6-tetramethylpiperidinyloxyl)-6-N-(2-methylaminopyridine)-7,12- dihydroindolo-[3,2-d][1]benzazepine-9-carboxamide methanol solvate ; _chemical_name_common ; N-(4-amino-2,2,6,6-tetramethylpiperidinyloxyl)-6-N-(2- methylaminopyridine)-7,12-dihydroindolo-(3,2-d)(1)benzazepine-9- carboxamide methanol solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C32 H35 N6 O2, C H4 O' _chemical_formula_sum 'C33 H39 N6 O3' _chemical_formula_weight 567.70 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Iba2 _symmetry_space_group_name_Hall 'I 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 17.778(2) _cell_length_b 26.576(3) _cell_length_c 12.4884(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5900.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7999 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 22.97 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2424 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66582 _diffrn_reflns_av_R_equivalents 0.0873 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3738 _reflns_number_gt 2927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0812P)^2^+3.9072P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? #_refine_ls_abs_structure_details #'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3738 _refine_ls_number_parameters 381 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 O1 O 0.42268(14) 0.11091(11) 0.5917(2) 0.0367(7) Uani 1 1 d . . . O2 O 0.75950(17) 0.10340(14) 0.3323(3) 0.0641(11) Uani 1 1 d . . . N1 N 0.10521(15) 0.16535(11) 0.4020(2) 0.0223(6) Uani 1 1 d . . . H1 H 0.0779 0.1675 0.3433 0.027 Uiso 1 1 calc R . . N2 N -0.00588(15) 0.15577(10) 0.7116(2) 0.0199(5) Uani 1 1 d . . . N3 N 0.08405(16) 0.11209(11) 0.8061(2) 0.0253(6) Uani 1 1 d . . . H300 H 0.1310 0.1112 0.8285 0.030 Uiso 1 1 calc R . . N4 N 0.10636(18) 0.00250(14) 0.8991(3) 0.0364(7) Uani 1 1 d . . . N5 N 0.45654(16) 0.10822(13) 0.4177(2) 0.0332(7) Uani 1 1 d . . . H5 H 0.4403 0.1085 0.3511 0.040 Uiso 1 1 calc R . . N6 N 0.69044(18) 0.10372(14) 0.3608(3) 0.0420(9) Uani 1 1 d . . . C1 C 0.32601(18) 0.12518(13) 0.4627(3) 0.0225(7) Uani 1 1 d . . . C2 C 0.30167(19) 0.12294(14) 0.3550(3) 0.0245(7) Uani 1 1 d . . . H2 H 0.3361 0.1128 0.3010 0.029 Uiso 1 1 calc R . . C3 C 0.22871(18) 0.13524(13) 0.3268(2) 0.0230(7) Uani 1 1 d . . . H3 H 0.2125 0.1332 0.2544 0.028 Uiso 1 1 calc R . . C4 C 0.17994(17) 0.15063(12) 0.4067(3) 0.0221(7) Uani 1 1 d . . . C5 C 0.08028(18) 0.17625(12) 0.5052(2) 0.0201(7) Uani 1 1 d . . . C6 C 0.00542(18) 0.19600(11) 0.5283(2) 0.0193(6) Uani 1 1 d . . . C7 C -0.03100(19) 0.22489(12) 0.4498(3) 0.0235(7) Uani 1 1 d . . . H7 H -0.0074 0.2294 0.3822 0.028 Uiso 1 1 calc R . . C8 C -0.1006(2) 0.24702(13) 0.4683(3) 0.0274(7) Uani 1 1 d . . . H8 H -0.1245 0.2663 0.4140 0.033 Uiso 1 1 calc R . . C9 C -0.1349(2) 0.24054(14) 0.5680(3) 0.0275(7) Uani 1 1 d . . . H9 H -0.1820 0.2560 0.5824 0.033 Uiso 1 1 calc R . . C10 C -0.10040(18) 0.21156(13) 0.6457(3) 0.0238(7) Uani 1 1 d . . . H10 H -0.1251 0.2069 0.7124 0.029 Uiso 1 1 calc R . . C11 C -0.02958(17) 0.18852(12) 0.6295(3) 0.0209(7) Uani 1 1 d . . . C12 C 0.06460(18) 0.14835(12) 0.7361(2) 0.0204(6) Uani 1 1 d . . . C13 C 0.0320(2) 0.07404(14) 0.8474(3) 0.0336(8) Uani 1 1 d . . . H13A H 0.0154 0.0519 0.7883 0.040 Uiso 1 1 calc R . . H13B H -0.0130 0.0907 0.8778 0.040 Uiso 1 1 calc R . . C14 C 0.07001(19) 0.04315(14) 0.9327(3) 0.0268(8) Uani 1 1 d . . . C15 C 0.0672(2) 0.05686(16) 1.0396(3) 0.0390(9) Uani 1 1 d . . . H15 H 0.0415 0.0866 1.0608 0.047 Uiso 1 1 calc R . . C16 C 0.1023(2) 0.0266(2) 1.1155(3) 0.0473(11) Uani 1 1 d . . . H16 H 0.1016 0.0356 1.1892 0.057 Uiso 1 1 calc R . . C17 C 0.1379(2) -0.01616(17) 1.0822(4) 0.0414(10) Uani 1 1 d . . . H17 H 0.1607 -0.0384 1.1322 0.050 Uiso 1 1 calc R . . C18 C 0.1399(3) -0.02617(16) 0.9736(4) 0.0418(10) Uani 1 1 d . . . H18 H 0.1665 -0.0551 0.9502 0.050 Uiso 1 1 calc R . . C19 C 0.13014(18) 0.17922(13) 0.6940(2) 0.0218(7) Uani 1 1 d . . . H19A H 0.1206 0.2155 0.7059 0.026 Uiso 1 1 calc R . . H19B H 0.1769 0.1699 0.7321 0.026 Uiso 1 1 calc R . . C20 C 0.13833(18) 0.16893(12) 0.5768(3) 0.0193(6) Uani 1 1 d . . . C21 C 0.20267(18) 0.15226(12) 0.5168(2) 0.0200(6) Uani 1 1 d . . . C22 C 0.27630(18) 0.13924(12) 0.5435(2) 0.0214(7) Uani 1 1 d . . . H22 H 0.2924 0.1399 0.6161 0.026 Uiso 1 1 calc R . . C23 C 0.4062(2) 0.11399(14) 0.4959(3) 0.0270(7) Uani 1 1 d . . . C24 C 0.5379(2) 0.10135(17) 0.4360(3) 0.0351(9) Uani 1 1 d . . . H24 H 0.5468 0.0902 0.5114 0.042 Uiso 1 1 calc R . . C25 C 0.5674(2) 0.06188(16) 0.3589(4) 0.0396(9) Uani 1 1 d . . . H25A H 0.5544 0.0721 0.2850 0.048 Uiso 1 1 calc R . . H25B H 0.5416 0.0296 0.3735 0.048 Uiso 1 1 calc R . . C26 C 0.6524(2) 0.05334(17) 0.3654(4) 0.0454(11) Uani 1 1 d . . . C27 C 0.6641(2) 0.14888(19) 0.4214(3) 0.0437(10) Uani 1 1 d . . . C28 C 0.5783(2) 0.15085(16) 0.4159(3) 0.0368(9) Uani 1 1 d . . . H28A H 0.5604 0.1757 0.4692 0.044 Uiso 1 1 calc R . . H28B H 0.5637 0.1633 0.3442 0.044 Uiso 1 1 calc R . . C29 C 0.6753(3) 0.0273(2) 0.4719(5) 0.0727(19) Uani 1 1 d . . . H29A H 0.7300 0.0226 0.4734 0.109 Uiso 1 1 calc R . . H29B H 0.6505 -0.0056 0.4769 0.109 Uiso 1 1 calc R . . H29C H 0.6600 0.0483 0.5325 0.109 Uiso 1 1 calc R . . C30 C 0.6785(3) 0.0224(2) 0.2689(5) 0.0605(14) Uani 1 1 d . . . H30A H 0.7330 0.0170 0.2734 0.091 Uiso 1 1 calc R . . H30B H 0.6666 0.0406 0.2028 0.091 Uiso 1 1 calc R . . H30C H 0.6528 -0.0102 0.2688 0.091 Uiso 1 1 calc R . . C31 C 0.6944(3) 0.1460(3) 0.5367(4) 0.0700(18) Uani 1 1 d . . . H31A H 0.7495 0.1443 0.5351 0.105 Uiso 1 1 calc R . . H31B H 0.6744 0.1159 0.5719 0.105 Uiso 1 1 calc R . . H31C H 0.6786 0.1760 0.5764 0.105 Uiso 1 1 calc R . . C32 C 0.6960(3) 0.19571(19) 0.3673(4) 0.0511(12) Uani 1 1 d . . . H32A H 0.7510 0.1946 0.3695 0.077 Uiso 1 1 calc R . . H32B H 0.6782 0.2258 0.4049 0.077 Uiso 1 1 calc R . . H32C H 0.6791 0.1968 0.2926 0.077 Uiso 1 1 calc R . . O3 O 0.04673(16) 0.36213(10) 0.6968(2) 0.0377(6) Uani 1 1 d . . . H3A H 0.0057 0.3723 0.6713 0.057 Uiso 1 1 calc R . . C33 C 0.0477(3) 0.30933(17) 0.6972(4) 0.0482(11) Uani 1 1 d . . . H33A H 0.0926 0.2975 0.7351 0.072 Uiso 1 1 calc R . . H33B H 0.0486 0.2969 0.6233 0.072 Uiso 1 1 calc R . . H33C H 0.0026 0.2967 0.7335 0.072 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 O1 0.0195(13) 0.0640(19) 0.0265(13) 0.0060(12) -0.0004(10) 0.0021(13) O2 0.0180(15) 0.080(2) 0.095(3) 0.028(2) 0.0189(16) 0.0007(15) N1 0.0160(13) 0.0336(15) 0.0172(13) 0.0028(11) -0.0006(10) 0.0024(11) N2 0.0160(13) 0.0285(13) 0.0151(12) 0.0032(11) 0.0006(10) 0.0024(11) N3 0.0140(13) 0.0369(16) 0.0249(14) 0.0063(12) -0.0009(11) 0.0007(12) N4 0.0365(18) 0.0382(17) 0.0344(17) -0.0047(14) -0.0059(14) 0.0050(15) N5 0.0155(14) 0.062(2) 0.0222(14) -0.0003(15) 0.0022(11) 0.0011(14) N6 0.0198(16) 0.057(2) 0.049(2) 0.0184(18) 0.0085(15) 0.0041(15) C1 0.0157(15) 0.0299(17) 0.0220(15) -0.0011(13) 0.0013(12) -0.0023(13) C2 0.0196(17) 0.0343(18) 0.0195(15) -0.0019(14) 0.0040(13) -0.0001(14) C3 0.0195(16) 0.0346(18) 0.0150(14) 0.0007(13) -0.0004(12) -0.0015(14) C4 0.0153(15) 0.0304(17) 0.0207(15) 0.0007(14) -0.0011(12) -0.0016(13) C5 0.0209(16) 0.0249(16) 0.0146(14) -0.0013(12) 0.0017(12) -0.0037(13) C6 0.0170(14) 0.0206(14) 0.0202(14) -0.0003(12) -0.0018(12) -0.0016(12) C7 0.0212(16) 0.0288(17) 0.0206(15) 0.0015(13) 0.0007(13) -0.0011(13) C8 0.0266(18) 0.0291(17) 0.0266(17) 0.0052(14) -0.0048(14) 0.0059(15) C9 0.0217(17) 0.0317(19) 0.0292(17) -0.0008(14) -0.0001(14) 0.0057(14) C10 0.0207(16) 0.0308(17) 0.0199(15) -0.0014(13) 0.0037(13) 0.0040(14) C11 0.0181(16) 0.0254(16) 0.0191(14) -0.0003(13) -0.0005(12) -0.0010(12) C12 0.0203(16) 0.0258(16) 0.0151(13) -0.0022(12) 0.0006(12) 0.0022(13) C13 0.0238(19) 0.038(2) 0.039(2) 0.0144(17) -0.0014(15) -0.0017(15) C14 0.0213(17) 0.0301(18) 0.0291(18) 0.0044(14) 0.0008(14) 0.0000(14) C15 0.038(2) 0.041(2) 0.039(2) -0.0037(18) 0.0051(18) 0.0051(18) C16 0.042(3) 0.075(3) 0.0243(18) 0.0012(19) 0.0038(18) -0.005(2) C17 0.033(2) 0.047(2) 0.043(2) 0.021(2) -0.0103(18) -0.0075(19) C18 0.041(2) 0.031(2) 0.054(3) -0.0013(18) -0.011(2) 0.0080(17) C19 0.0175(15) 0.0326(17) 0.0153(14) 0.0002(13) -0.0003(12) 0.0017(13) C20 0.0173(16) 0.0221(15) 0.0185(14) 0.0007(12) -0.0007(12) -0.0011(13) C21 0.0193(16) 0.0239(16) 0.0169(14) 0.0012(12) 0.0007(12) -0.0028(13) C22 0.0192(16) 0.0273(16) 0.0177(14) 0.0017(13) -0.0016(12) -0.0020(13) C23 0.0197(17) 0.0323(19) 0.0292(17) -0.0021(14) 0.0023(13) -0.0020(14) C24 0.0147(16) 0.062(3) 0.0286(18) 0.0026(18) -0.0004(14) 0.0028(16) C25 0.028(2) 0.043(2) 0.048(2) 0.0063(19) 0.0095(17) -0.0008(17) C26 0.028(2) 0.052(2) 0.057(3) 0.019(2) 0.0186(19) 0.0100(18) C27 0.0229(19) 0.073(3) 0.036(2) 0.004(2) -0.0010(17) -0.0070(19) C28 0.0224(18) 0.053(2) 0.035(2) -0.0054(19) 0.0005(16) 0.0010(17) C29 0.042(3) 0.080(4) 0.095(5) 0.053(3) 0.014(3) 0.017(3) C30 0.047(3) 0.060(3) 0.075(4) 0.003(3) 0.030(3) 0.019(2) C31 0.032(3) 0.131(5) 0.047(3) 0.004(3) -0.009(2) -0.016(3) C32 0.038(3) 0.061(3) 0.055(3) -0.006(2) 0.005(2) -0.012(2) O3 0.0321(15) 0.0443(15) 0.0366(14) -0.0041(12) -0.0082(13) -0.0013(12) C33 0.057(3) 0.054(3) 0.033(2) 0.003(2) 0.000(2) 0.001(2) _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 O1 C23 1.234(5) . ? O2 N6 1.278(4) . ? N1 C4 1.386(4) . ? N1 C5 1.393(4) . ? N1 H1 0.8800 . ? N2 C12 1.305(4) . ? N2 C11 1.409(4) . ? N3 C12 1.347(4) . ? N3 C13 1.465(5) . ? N3 H300 0.8800 . ? N4 C14 1.327(5) . ? N4 C18 1.341(5) . ? N5 C23 1.334(4) . ? N5 C24 1.476(4) . ? N5 H5 0.8800 . ? N6 C27 1.494(6) . ? N6 C26 1.501(6) . ? C1 C22 1.392(4) . ? C1 C2 1.415(4) . ? C1 C23 1.514(5) . ? C2 C3 1.383(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(4) . ? C3 H3 0.9500 . ? C4 C21 1.434(4) . ? C5 C20 1.380(5) . ? C5 C6 1.459(4) . ? C6 C7 1.403(4) . ? C6 C11 1.423(4) . ? C7 C8 1.389(5) . ? C7 H7 0.9500 . ? C8 C9 1.397(5) . ? C8 H8 0.9500 . ? C9 C10 1.382(5) . ? C9 H9 0.9500 . ? C10 C11 1.415(4) . ? C10 H10 0.9500 . ? C12 C19 1.519(5) . ? C13 C14 1.504(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.385(5) . ? C15 C16 1.391(6) . ? C15 H15 0.9500 . ? C16 C17 1.366(7) . ? C16 H16 0.9500 . ? C17 C18 1.383(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.496(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.438(5) . ? C21 C22 1.394(4) . ? C22 H22 0.9500 . ? C24 C25 1.518(6) . ? C24 C28 1.520(6) . ? C24 H24 1.0000 . ? C25 C26 1.530(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C30 1.530(7) . ? C26 C29 1.554(7) . ? C27 C32 1.525(7) . ? C27 C28 1.527(5) . ? C27 C31 1.539(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? O3 C33 1.403(5) . ? O3 H3A 0.8400 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C4 N1 C5 108.9(3) . . ? C4 N1 H1 125.5 . . ? C5 N1 H1 125.5 . . ? C12 N2 C11 123.4(3) . . ? C12 N3 C13 124.1(3) . . ? C12 N3 H300 118.0 . . ? C13 N3 H300 118.0 . . ? C14 N4 C18 117.4(3) . . ? C23 N5 C24 123.9(3) . . ? C23 N5 H5 118.0 . . ? C24 N5 H5 118.0 . . ? O2 N6 C27 116.5(4) . . ? O2 N6 C26 115.9(4) . . ? C27 N6 C26 123.8(3) . . ? C22 C1 C2 120.4(3) . . ? C22 C1 C23 116.9(3) . . ? C2 C1 C23 122.7(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 118.2(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 N1 130.8(3) . . ? C3 C4 C21 121.6(3) . . ? N1 C4 C21 107.6(3) . . ? C20 C5 N1 109.4(3) . . ? C20 C5 C6 127.2(3) . . ? N1 C5 C6 123.2(3) . . ? C7 C6 C11 119.7(3) . . ? C7 C6 C5 118.7(3) . . ? C11 C6 C5 121.6(3) . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 119.0(3) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 122.4(3) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? N2 C11 C10 115.4(3) . . ? N2 C11 C6 127.0(3) . . ? C10 C11 C6 117.1(3) . . ? N2 C12 N3 120.5(3) . . ? N2 C12 C19 125.0(3) . . ? N3 C12 C19 114.5(3) . . ? N3 C13 C14 110.0(3) . . ? N3 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? N3 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N4 C14 C15 122.4(3) . . ? N4 C14 C13 116.1(3) . . ? C15 C14 C13 121.5(3) . . ? C14 C15 C16 119.3(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 118.8(4) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 118.1(4) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? N4 C18 C17 124.0(4) . . ? N4 C18 H18 118.0 . . ? C17 C18 H18 118.0 . . ? C20 C19 C12 108.3(3) . . ? C20 C19 H19A 110.0 . . ? C12 C19 H19A 110.0 . . ? C20 C19 H19B 110.0 . . ? C12 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? C5 C20 C21 107.5(3) . . ? C5 C20 C19 122.4(3) . . ? C21 C20 C19 130.1(3) . . ? C22 C21 C4 119.1(3) . . ? C22 C21 C20 134.3(3) . . ? C4 C21 C20 106.5(3) . . ? C1 C22 C21 119.3(3) . . ? C1 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? O1 C23 N5 122.9(3) . . ? O1 C23 C1 120.1(3) . . ? N5 C23 C1 117.0(3) . . ? N5 C24 C25 109.1(3) . . ? N5 C24 C28 109.3(3) . . ? C25 C24 C28 109.3(3) . . ? N5 C24 H24 109.7 . . ? C25 C24 H24 109.7 . . ? C28 C24 H24 109.7 . . ? C24 C25 C26 114.2(4) . . ? C24 C25 H25A 108.7 . . ? C26 C25 H25A 108.7 . . ? C24 C25 H25B 108.7 . . ? C26 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? N6 C26 C25 108.1(3) . . ? N6 C26 C30 108.2(3) . . ? C25 C26 C30 109.7(4) . . ? N6 C26 C29 108.2(4) . . ? C25 C26 C29 111.8(4) . . ? C30 C26 C29 110.8(4) . . ? N6 C27 C32 108.3(3) . . ? N6 C27 C28 108.5(3) . . ? C32 C27 C28 108.8(4) . . ? N6 C27 C31 109.0(4) . . ? C32 C27 C31 108.9(4) . . ? C28 C27 C31 113.1(4) . . ? C24 C28 C27 115.8(4) . . ? C24 C28 H28A 108.3 . . ? C27 C28 H28A 108.3 . . ? C24 C28 H28B 108.3 . . ? C27 C28 H28B 108.3 . . ? H28A C28 H28B 107.4 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C33 O3 H3A 109.5 . . ? O3 C33 H33A 109.5 . . ? O3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? 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 C22 C1 C2 C3 1.0(5) . . . . ? C23 C1 C2 C3 -177.5(3) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 N1 179.5(3) . . . . ? C2 C3 C4 C21 -2.2(5) . . . . ? C5 N1 C4 C3 178.6(3) . . . . ? C5 N1 C4 C21 0.1(4) . . . . ? C4 N1 C5 C20 0.3(4) . . . . ? C4 N1 C5 C6 175.9(3) . . . . ? C20 C5 C6 C7 146.9(3) . . . . ? N1 C5 C6 C7 -28.0(5) . . . . ? C20 C5 C6 C11 -30.3(5) . . . . ? N1 C5 C6 C11 154.8(3) . . . . ? C11 C6 C7 C8 0.6(5) . . . . ? C5 C6 C7 C8 -176.7(3) . . . . ? C6 C7 C8 C9 0.4(5) . . . . ? C7 C8 C9 C10 -1.4(5) . . . . ? C8 C9 C10 C11 1.4(5) . . . . ? C12 N2 C11 C10 -149.6(3) . . . . ? C12 N2 C11 C6 38.4(5) . . . . ? C9 C10 C11 N2 -173.3(3) . . . . ? C9 C10 C11 C6 -0.5(5) . . . . ? C7 C6 C11 N2 171.3(3) . . . . ? C5 C6 C11 N2 -11.5(5) . . . . ? C7 C6 C11 C10 -0.5(4) . . . . ? C5 C6 C11 C10 176.6(3) . . . . ? C11 N2 C12 N3 -171.8(3) . . . . ? C11 N2 C12 C19 10.4(5) . . . . ? C13 N3 C12 N2 9.4(5) . . . . ? C13 N3 C12 C19 -172.5(3) . . . . ? C12 N3 C13 C14 -173.8(3) . . . . ? C18 N4 C14 C15 1.3(6) . . . . ? C18 N4 C14 C13 -179.0(4) . . . . ? N3 C13 C14 N4 -89.5(4) . . . . ? N3 C13 C14 C15 90.2(4) . . . . ? N4 C14 C15 C16 -1.3(6) . . . . ? C13 C14 C15 C16 179.1(4) . . . . ? C14 C15 C16 C17 -0.8(6) . . . . ? C15 C16 C17 C18 2.6(7) . . . . ? C14 N4 C18 C17 0.8(6) . . . . ? C16 C17 C18 N4 -2.8(7) . . . . ? N2 C12 C19 C20 -68.2(4) . . . . ? N3 C12 C19 C20 113.9(3) . . . . ? N1 C5 C20 C21 -0.5(4) . . . . ? C6 C5 C20 C21 -176.0(3) . . . . ? N1 C5 C20 C19 177.8(3) . . . . ? C6 C5 C20 C19 2.4(5) . . . . ? C12 C19 C20 C5 56.5(4) . . . . ? C12 C19 C20 C21 -125.5(4) . . . . ? C3 C4 C21 C22 1.7(5) . . . . ? N1 C4 C21 C22 -179.7(3) . . . . ? C3 C4 C21 C20 -179.1(3) . . . . ? N1 C4 C21 C20 -0.4(4) . . . . ? C5 C20 C21 C22 179.7(4) . . . . ? C19 C20 C21 C22 1.5(6) . . . . ? C5 C20 C21 C4 0.6(4) . . . . ? C19 C20 C21 C4 -177.6(3) . . . . ? C2 C1 C22 C21 -1.5(5) . . . . ? C23 C1 C22 C21 177.0(3) . . . . ? C4 C21 C22 C1 0.3(5) . . . . ? C20 C21 C22 C1 -178.8(3) . . . . ? C24 N5 C23 O1 -4.7(6) . . . . ? C24 N5 C23 C1 174.8(4) . . . . ? C22 C1 C23 O1 9.7(5) . . . . ? C2 C1 C23 O1 -171.8(4) . . . . ? C22 C1 C23 N5 -169.9(3) . . . . ? C2 C1 C23 N5 8.7(5) . . . . ? C23 N5 C24 C25 139.3(4) . . . . ? C23 N5 C24 C28 -101.3(4) . . . . ? N5 C24 C25 C26 176.7(3) . . . . ? C28 C24 C25 C26 57.2(4) . . . . ? O2 N6 C26 C25 -159.2(4) . . . . ? C27 N6 C26 C25 43.4(5) . . . . ? O2 N6 C26 C30 -40.4(5) . . . . ? C27 N6 C26 C30 162.2(4) . . . . ? O2 N6 C26 C29 79.6(5) . . . . ? C27 N6 C26 C29 -77.8(5) . . . . ? C24 C25 C26 N6 -49.4(5) . . . . ? C24 C25 C26 C30 -167.2(4) . . . . ? C24 C25 C26 C29 69.5(5) . . . . ? O2 N6 C27 C32 43.6(5) . . . . ? C26 N6 C27 C32 -159.1(4) . . . . ? O2 N6 C27 C28 161.6(4) . . . . ? C26 N6 C27 C28 -41.1(5) . . . . ? O2 N6 C27 C31 -74.8(5) . . . . ? C26 N6 C27 C31 82.5(5) . . . . ? N5 C24 C28 C27 -174.5(3) . . . . ? C25 C24 C28 C27 -55.2(5) . . . . ? N6 C27 C28 C24 45.2(5) . . . . ? C32 C27 C28 C24 162.9(4) . . . . ? C31 C27 C28 C24 -75.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.524 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.057