Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Akimitsu Okamoto' _publ_contact_author_address ; Frontier Research System, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan ; _publ_contact_author_email AKI-OKAMOTO@RIKEN.JP _publ_section_title ; Synthesis and characterization of the 5-methyl-2'-deoxycytidine glycol-dioxoosmium-bipyridine ternary complex in DNA ; loop_ _publ_author_name 'Akimitsu Okamoto' 'Tadashi Umemoto' data_Os-complex _database_code_depnum_ccdc_archive 'CCDC 665206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 N4 O9 Os, 4(H2 O)' _chemical_formula_sum 'C20 H30 N4 O13 Os' _chemical_formula_weight 724.68 _chemical_absolute_configuration rmad 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' Os Os -1.2165 7.6030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.4747(13) _cell_length_b 6.7238(7) _cell_length_c 15.8519(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.2644(18) _cell_angle_gamma 90.00 _cell_volume 1213.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5797 _cell_measurement_theta_min 1.7890 _cell_measurement_theta_max 32.5967 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 5.333 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6292 _exptl_absorpt_correction_T_max 0.9489 _exptl_absorpt_process_details ; Numabs (Higashi, 1999) Numabs, Numerical Absorption Correction, Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ? _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator cofocal _diffrn_measurement_device_type ; Rigaku AFC-8 with Saturn70 CCD detector ; _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21152 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 31.00 _reflns_number_total 7525 _reflns_number_gt 6583 _reflns_threshold_expression I>2\s(I) _diffrn_measurement_details ; scan: Number of images: 60 Slice: -10.0000 - 20.0000 Image width: 0.5000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 0.0000 Phi: 0.0000 XTD: 40.0387 2theta: 20.0786 scan: Number of images: 60 Slice: 20.0000 - 50.0000 Image width: 0.5000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 20.0000 Phi: 0.0000 XTD: 40.0387 2theta: 20.0786 scan: Number of images: 344 Slice: -70.0000 - 102.0000 Image width: 0.5000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 50.0000 Phi: 90.0000 XTD: 40.0387 2theta: 20.0786 scan: Number of images: 360 Slice: -70.0000 - 110.0000 Image width: 0.5000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 50.0000 Phi: 180.0000 XTD: 40.0387 2theta: 20.0786 scan: Number of images: 360 Slice: -70.0000 - 110.0000 Image width: 0.5000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 50.0000 Phi: 135.0000 XTD: 40.0387 2theta: 20.0786 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3-circle ; _diffrn_orient_matrix_UB_11 0.0040 _diffrn_orient_matrix_UB_12 0.0482 _diffrn_orient_matrix_UB_13 0.0733 _diffrn_orient_matrix_UB_21 0.1480 _diffrn_orient_matrix_UB_22 0.0072 _diffrn_orient_matrix_UB_23 -0.0128 _diffrn_orient_matrix_UB_31 -0.0052 _diffrn_orient_matrix_UB_32 0.0571 _diffrn_orient_matrix_UB_33 -0.0276 _diffrn_orient_matrix_type d*Trek _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution SIR-2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material SHELXL-97 _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^)+(0.0069P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 -0.009(5) _refine_ls_number_reflns 7525 _refine_ls_number_parameters 357 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0456 _refine_ls_wR_factor_gt 0.0450 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Os1 Os 0.207476(8) 0.55103(5) 0.166448(6) 0.00655(3) Uani 1 1 d . . . O1 O 0.2999(2) 0.1399(3) 0.43479(14) 0.0117(5) Uani 1 1 d . . . O2 O 0.4089(2) 0.6787(4) 0.52381(14) 0.0184(6) Uani 1 1 d . . . O3 O 0.4798(2) 0.8836(4) 0.26359(16) 0.0184(6) Uani 1 1 d . . . O4 O 0.38200(15) 0.5430(9) 0.18687(11) 0.0083(4) Uani 1 1 d . . . O5 O 0.22124(17) 0.5254(7) 0.29087(12) 0.0136(8) Uani 1 1 d . . . O6 O 0.1635(3) 0.1596(4) 0.59226(15) 0.0178(6) Uani 1 1 d . . . H6H H 0.1730 0.0385 0.6041 0.027 Uiso 1 1 calc R . . O7 O 0.0746(2) 0.1365(4) 0.31517(16) 0.0206(6) Uani 1 1 d . . . H7H H 0.1276 0.2180 0.3071 0.031 Uiso 1 1 calc R . . O8 O 0.1913(3) 0.2948(7) 0.1502(2) 0.0132(8) Uani 1 1 d . . . O9 O 0.1989(3) 0.8103(7) 0.16450(19) 0.0103(8) Uani 1 1 d . . . N1 N 0.3563(2) 0.4677(4) 0.41334(18) 0.0087(6) Uani 1 1 d . . . N2 N 0.4368(2) 0.7815(4) 0.39091(17) 0.0119(6) Uani 1 1 d . . . H2N H 0.4539 0.9009 0.4115 0.014 Uiso 1 1 calc R . . N3 N 0.1802(2) 0.5661(10) 0.03186(13) 0.0077(6) Uani 1 1 d . . . N4 N 0.02243(18) 0.5543(11) 0.13945(13) 0.0083(4) Uani 1 1 d . . . C1 C 0.4003(3) 0.6400(5) 0.4476(2) 0.0112(7) Uani 1 1 d . . . C2 C 0.4483(3) 0.7515(5) 0.3066(2) 0.0109(7) Uani 1 1 d . . . C3 C 0.4258(2) 0.5406(12) 0.27562(16) 0.0086(7) Uani 1 1 d . . . C4 C 0.3320(3) 0.4415(5) 0.32096(19) 0.0083(6) Uani 1 1 d . . . H4 H 0.3302 0.2961 0.3076 0.010 Uiso 1 1 calc R . . C5 C 0.3006(3) 0.3352(5) 0.4692(2) 0.0090(6) Uani 1 1 d . . . H5 H 0.3468 0.3358 0.5271 0.011 Uiso 1 1 calc R . . C6 C 0.1738(3) 0.3834(5) 0.4766(2) 0.0108(7) Uani 1 1 d . . . H6A H 0.1317 0.4293 0.4217 0.013 Uiso 1 1 calc R . . H6B H 0.1670 0.4855 0.5207 0.013 Uiso 1 1 calc R . . C7 C 0.1282(3) 0.1818(5) 0.5024(2) 0.0119(7) Uani 1 1 d . . . H7 H 0.0410 0.1707 0.4877 0.014 Uiso 1 1 calc R . . C8 C 0.1930(2) 0.0402(12) 0.45000(18) 0.0130(7) Uani 1 1 d . . . H8 H 0.2147 -0.0812 0.4849 0.016 Uiso 1 1 calc R . . C9 C 0.1250(3) -0.0256(5) 0.3652(2) 0.0186(8) Uani 1 1 d . . . H9A H 0.1787 -0.0994 0.3323 0.022 Uiso 1 1 calc R . . H9B H 0.0615 -0.1177 0.3767 0.022 Uiso 1 1 calc R . . C10 C 0.5425(3) 0.4264(6) 0.2885(2) 0.0148(7) Uani 1 1 d . . . H10A H 0.5759 0.4333 0.3485 0.022 Uiso 1 1 calc R . . H10B H 0.5975 0.4860 0.2533 0.022 Uiso 1 1 calc R . . H10C H 0.5287 0.2871 0.2721 0.022 Uiso 1 1 calc R . . C11 C 0.0658(2) 0.5553(11) -0.00415(15) 0.0076(5) Uani 1 1 d . . . C12 C 0.2670(3) 0.5742(8) -0.01746(18) 0.0093(8) Uani 1 1 d . . . H12 H 0.3460 0.5855 0.0084 0.011 Uiso 1 1 calc R . . C13 C 0.2435(3) 0.5665(11) -0.10590(17) 0.0116(7) Uani 1 1 d . . . H13 H 0.3057 0.5688 -0.1401 0.014 Uiso 1 1 calc R . . C14 C 0.1271(2) 0.5552(11) -0.14310(15) 0.0108(5) Uani 1 1 d . . . H14 H 0.1090 0.5535 -0.2033 0.013 Uiso 1 1 calc R . . C15 C 0.0376(2) 0.5464(11) -0.09195(16) 0.0096(5) Uani 1 1 d . . . H15 H -0.0420 0.5344 -0.1166 0.012 Uiso 1 1 calc R . . C16 C -0.0220(2) 0.5537(13) 0.05590(15) 0.0079(5) Uani 1 1 d . . . C17 C -0.0505(2) 0.5602(11) 0.19964(17) 0.0114(6) Uani 1 1 d . . . H17 H -0.0180 0.5614 0.2578 0.014 Uiso 1 1 calc R . . C18 C -0.1705(3) 0.5645(11) 0.17928(18) 0.0135(7) Uani 1 1 d . . . H18 H -0.2203 0.5682 0.2228 0.016 Uiso 1 1 calc R . . C19 C -0.2178(2) 0.5634(12) 0.09441(18) 0.0132(7) Uani 1 1 d . . . H19 H -0.3005 0.5665 0.0790 0.016 Uiso 1 1 calc R . . C20 C -0.1422(2) 0.5576(11) 0.03134(16) 0.0107(5) Uani 1 1 d . . . H20 H -0.1730 0.5564 -0.0272 0.013 Uiso 1 1 calc R . . O1W O 0.4975(3) 0.2785(6) 0.0866(3) 0.0299(9) Uani 1 1 d . . . O2W O 0.2696(2) 0.4614(4) 0.69458(15) 0.0170(6) Uani 1 1 d . . . O3W O -0.1348(2) 0.2809(4) 0.36224(16) 0.0196(6) Uani 1 1 d . . . O4W O 0.5348(4) 0.3796(6) -0.0765(3) 0.0463(14) Uani 1 1 d . . . 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 Os1 0.00606(4) 0.00762(5) 0.00562(5) 0.00017(11) -0.00058(3) -0.00034(12) O1 0.0128(12) 0.0095(12) 0.0141(12) -0.0021(10) 0.0065(9) -0.0007(10) O2 0.0287(15) 0.0198(14) 0.0061(11) -0.0051(11) -0.0006(10) -0.0062(12) O3 0.0227(14) 0.0160(14) 0.0156(13) 0.0026(11) -0.0005(11) -0.0092(11) O4 0.0065(8) 0.0122(12) 0.0058(8) 0.005(2) -0.0010(6) -0.0001(19) O5 0.0059(9) 0.030(2) 0.0053(9) 0.0038(13) -0.0003(7) 0.0011(13) O6 0.0283(15) 0.0139(14) 0.0115(12) 0.0022(10) 0.0035(11) -0.0004(13) O7 0.0157(13) 0.0296(16) 0.0158(13) 0.0039(11) -0.0011(11) -0.0039(11) O8 0.0116(17) 0.0081(19) 0.0184(16) 0.0020(14) -0.0034(13) 0.0000(13) O9 0.0130(17) 0.0070(19) 0.0105(15) -0.0021(12) 0.0006(12) -0.0005(12) N1 0.0073(14) 0.0114(14) 0.0071(14) -0.0002(11) 0.0003(11) -0.0011(11) N2 0.0158(15) 0.0086(14) 0.0107(14) -0.0012(11) -0.0008(11) -0.0033(12) N3 0.0096(10) 0.0085(17) 0.0047(9) 0.0005(18) 0.0001(8) 0.0003(18) N4 0.0071(9) 0.0090(11) 0.0086(10) 0.001(3) 0.0005(7) 0.000(3) C1 0.0093(16) 0.0143(18) 0.0097(17) 0.0037(14) 0.0001(13) -0.0013(14) C2 0.0102(15) 0.0125(18) 0.0096(15) 0.0016(13) -0.0011(12) -0.0030(13) C3 0.0078(11) 0.0133(19) 0.0046(11) -0.005(2) 0.0000(8) 0.000(2) C4 0.0072(14) 0.0128(17) 0.0047(14) -0.0027(13) -0.0008(11) -0.0005(13) C5 0.0124(16) 0.0082(16) 0.0067(15) 0.0017(12) 0.0017(12) -0.0007(13) C6 0.0114(16) 0.0119(17) 0.0096(16) 0.0019(13) 0.0033(12) -0.0002(13) C7 0.0116(15) 0.0122(16) 0.0117(15) -0.0010(14) 0.0011(12) -0.0002(14) C8 0.0122(12) 0.015(2) 0.0121(12) -0.005(3) 0.0016(10) -0.003(3) C9 0.0200(19) 0.021(2) 0.0147(18) -0.0049(15) 0.0017(15) -0.0041(15) C10 0.0121(17) 0.0190(19) 0.0129(17) 0.0038(14) 0.0005(13) 0.0056(14) C11 0.0085(11) 0.0050(12) 0.0089(11) 0.001(3) 0.0000(9) 0.002(3) C12 0.0097(12) 0.005(2) 0.0131(13) 0.0008(16) 0.0001(10) 0.0018(15) C13 0.0143(13) 0.012(2) 0.0086(12) 0.002(2) 0.0032(10) 0.002(2) C14 0.0161(13) 0.0104(13) 0.0054(11) -0.001(3) -0.0004(9) -0.002(3) C15 0.0111(12) 0.0072(13) 0.0093(12) -0.005(3) -0.0035(9) -0.001(3) C16 0.0081(11) 0.0058(11) 0.0093(11) -0.001(3) -0.0004(9) 0.000(3) C17 0.0133(12) 0.0121(16) 0.0088(11) 0.001(3) 0.0022(9) -0.003(3) C18 0.0109(12) 0.015(2) 0.0155(13) 0.002(3) 0.0046(10) -0.002(2) C19 0.0083(12) 0.0106(19) 0.0196(14) 0.002(3) -0.0021(10) 0.000(2) C20 0.0103(12) 0.0085(13) 0.0123(12) -0.004(3) -0.0019(9) 0.001(3) O1W 0.041(2) 0.026(2) 0.0260(19) 0.0095(16) 0.0167(15) 0.0148(17) O2W 0.0167(13) 0.0202(14) 0.0142(12) -0.0018(11) 0.0024(10) 0.0031(11) O3W 0.0259(15) 0.0115(13) 0.0216(14) -0.0015(11) 0.0037(11) 0.0018(11) O4W 0.077(3) 0.049(3) 0.0175(18) 0.0122(18) 0.024(2) 0.044(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 Os1 O9 1.746(5) . ? Os1 O8 1.749(5) . ? Os1 O5 1.966(2) . ? Os1 O4 1.9886(18) . ? Os1 N4 2.112(2) . ? Os1 N3 2.119(2) . ? O1 C5 1.422(4) . ? O1 C8 1.445(5) . ? O2 C1 1.228(4) . ? O3 C2 1.203(4) . ? O4 C3 1.433(3) . ? O5 C4 1.417(4) . ? O6 C7 1.439(4) . ? O6 H6H 0.8400 . ? O7 C9 1.427(4) . ? O7 H7H 0.8400 . ? N1 C1 1.350(4) . ? N1 C5 1.459(4) . ? N1 C4 1.466(4) . ? N2 C2 1.374(4) . ? N2 C1 1.408(4) . ? N2 H2N 0.8800 . ? N3 C12 1.343(3) . ? N3 C11 1.365(3) . ? N4 C17 1.347(3) . ? N4 C16 1.358(3) . ? C2 C3 1.512(8) . ? C3 C4 1.521(5) . ? C3 C10 1.535(6) . ? C4 H4 1.0000 . ? C5 C6 1.509(4) . ? C5 H5 1.0000 . ? C6 C7 1.527(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(6) . ? C7 H7 1.0000 . ? C8 C9 1.531(5) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C15 1.390(3) . ? C11 C16 1.471(3) . ? C12 C13 1.395(4) . ? C12 H12 0.9500 . ? C13 C14 1.392(4) . ? C13 H13 0.9500 . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C20 1.385(3) . ? C17 C18 1.374(4) . ? C17 H17 0.9500 . ? C18 C19 1.386(4) . ? C18 H18 0.9500 . ? C19 C20 1.405(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 O9 Os1 O8 167.54(10) . . ? O9 Os1 O5 95.87(17) . . ? O8 Os1 O5 93.16(18) . . ? O9 Os1 O4 94.8(2) . . ? O8 Os1 O4 94.8(2) . . ? O5 Os1 O4 83.27(8) . . ? O9 Os1 N4 86.1(2) . . ? O8 Os1 N4 84.0(2) . . ? O5 Os1 N4 98.93(8) . . ? O4 Os1 N4 177.52(14) . . ? O9 Os1 N3 86.2(2) . . ? O8 Os1 N3 84.2(2) . . ? O5 Os1 N3 175.53(16) . . ? O4 Os1 N3 100.53(8) . . ? N4 Os1 N3 77.22(8) . . ? C5 O1 C8 109.1(3) . . ? C3 O4 Os1 112.39(15) . . ? C4 O5 Os1 109.11(18) . . ? C7 O6 H6H 109.5 . . ? C9 O7 H7H 109.5 . . ? C1 N1 C5 116.8(3) . . ? C1 N1 C4 121.2(3) . . ? C5 N1 C4 119.3(3) . . ? C2 N2 C1 126.5(3) . . ? C2 N2 H2N 116.8 . . ? C1 N2 H2N 116.8 . . ? C12 N3 C11 120.2(2) . . ? C12 N3 Os1 124.19(18) . . ? C11 N3 Os1 115.49(18) . . ? C17 N4 C16 120.1(2) . . ? C17 N4 Os1 123.73(17) . . ? C16 N4 Os1 116.18(16) . . ? O2 C1 N1 123.8(3) . . ? O2 C1 N2 119.4(3) . . ? N1 C1 N2 116.7(3) . . ? O3 C2 N2 121.0(3) . . ? O3 C2 C3 124.0(3) . . ? N2 C2 C3 114.8(3) . . ? O4 C3 C2 109.4(5) . . ? O4 C3 C4 106.7(3) . . ? C2 C3 C4 111.1(3) . . ? O4 C3 C10 109.2(3) . . ? C2 C3 C10 108.4(3) . . ? C4 C3 C10 112.0(5) . . ? O5 C4 N1 109.7(3) . . ? O5 C4 C3 108.9(3) . . ? N1 C4 C3 111.3(3) . . ? O5 C4 H4 109.0 . . ? N1 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? O1 C5 N1 108.2(3) . . ? O1 C5 C6 105.7(3) . . ? N1 C5 C6 114.7(3) . . ? O1 C5 H5 109.4 . . ? N1 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C5 C6 C7 101.4(3) . . ? C5 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? C5 C6 H6B 111.5 . . ? C7 C6 H6B 111.5 . . ? H6A C6 H6B 109.3 . . ? O6 C7 C8 112.4(3) . . ? O6 C7 C6 107.1(3) . . ? C8 C7 C6 101.6(4) . . ? O6 C7 H7 111.7 . . ? C8 C7 H7 111.7 . . ? C6 C7 H7 111.7 . . ? O1 C8 C7 106.6(5) . . ? O1 C8 C9 109.7(3) . . ? C7 C8 C9 115.5(3) . . ? O1 C8 H8 108.3 . . ? C7 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? O7 C9 C8 113.1(4) . . ? O7 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? O7 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C15 120.7(2) . . ? N3 C11 C16 115.5(2) . . ? C15 C11 C16 123.7(2) . . ? N3 C12 C13 121.3(3) . . ? N3 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 118.8(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C11 119.1(2) . . ? C14 C15 H15 120.4 . . ? C11 C15 H15 120.4 . . ? N4 C16 C20 120.8(2) . . ? N4 C16 C11 115.3(2) . . ? C20 C16 C11 123.9(2) . . ? N4 C17 C18 121.9(2) . . ? N4 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 119.3(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C16 C20 C19 118.9(2) . . ? C16 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? 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 O9 Os1 O4 C3 90.5(5) . . . . ? O8 Os1 O4 C3 -97.4(5) . . . . ? O5 Os1 O4 C3 -4.8(5) . . . . ? N4 Os1 O4 C3 -158(6) . . . . ? N3 Os1 O4 C3 177.6(5) . . . . ? O9 Os1 O5 C4 -116.3(3) . . . . ? O8 Os1 O5 C4 72.3(3) . . . . ? O4 Os1 O5 C4 -22.1(3) . . . . ? N4 Os1 O5 C4 156.7(3) . . . . ? N3 Os1 O5 C4 126(3) . . . . ? O9 Os1 N3 C12 92.1(6) . . . . ? O8 Os1 N3 C12 -95.8(6) . . . . ? O5 Os1 N3 C12 -150(3) . . . . ? O4 Os1 N3 C12 -2.0(6) . . . . ? N4 Os1 N3 C12 179.0(6) . . . . ? O9 Os1 N3 C11 -91.6(5) . . . . ? O8 Os1 N3 C11 80.4(5) . . . . ? O5 Os1 N3 C11 26(3) . . . . ? O4 Os1 N3 C11 174.2(5) . . . . ? N4 Os1 N3 C11 -4.7(5) . . . . ? O9 Os1 N4 C17 -88.7(6) . . . . ? O8 Os1 N4 C17 98.9(7) . . . . ? O5 Os1 N4 C17 6.6(7) . . . . ? O4 Os1 N4 C17 159(6) . . . . ? N3 Os1 N4 C17 -175.7(7) . . . . ? O9 Os1 N4 C16 90.1(6) . . . . ? O8 Os1 N4 C16 -82.3(6) . . . . ? O5 Os1 N4 C16 -174.5(6) . . . . ? O4 Os1 N4 C16 -22(7) . . . . ? N3 Os1 N4 C16 3.2(6) . . . . ? C5 N1 C1 O2 9.4(5) . . . . ? C4 N1 C1 O2 170.8(3) . . . . ? C5 N1 C1 N2 -170.1(3) . . . . ? C4 N1 C1 N2 -8.7(5) . . . . ? C2 N2 C1 O2 170.3(3) . . . . ? C2 N2 C1 N1 -10.2(5) . . . . ? C1 N2 C2 O3 179.6(3) . . . . ? C1 N2 C2 C3 -3.9(5) . . . . ? Os1 O4 C3 C2 -91.9(4) . . . . ? Os1 O4 C3 C4 28.4(7) . . . . ? Os1 O4 C3 C10 149.7(3) . . . . ? O3 C2 C3 O4 -32.6(4) . . . . ? N2 C2 C3 O4 151.0(3) . . . . ? O3 C2 C3 C4 -150.2(3) . . . . ? N2 C2 C3 C4 33.4(4) . . . . ? O3 C2 C3 C10 86.3(4) . . . . ? N2 C2 C3 C10 -90.1(3) . . . . ? Os1 O5 C4 N1 165.7(2) . . . . ? Os1 O5 C4 C3 43.7(4) . . . . ? C1 N1 C4 O5 -82.3(4) . . . . ? C5 N1 C4 O5 78.6(4) . . . . ? C1 N1 C4 C3 38.4(5) . . . . ? C5 N1 C4 C3 -160.7(4) . . . . ? O4 C3 C4 O5 -47.1(6) . . . . ? C2 C3 C4 O5 72.1(3) . . . . ? C10 C3 C4 O5 -166.6(3) . . . . ? O4 C3 C4 N1 -168.2(4) . . . . ? C2 C3 C4 N1 -49.0(4) . . . . ? C10 C3 C4 N1 72.3(5) . . . . ? C8 O1 C5 N1 -144.3(3) . . . . ? C8 O1 C5 C6 -21.0(3) . . . . ? C1 N1 C5 O1 -158.6(3) . . . . ? C4 N1 C5 O1 39.6(4) . . . . ? C1 N1 C5 C6 83.7(4) . . . . ? C4 N1 C5 C6 -78.0(4) . . . . ? O1 C5 C6 C7 36.8(3) . . . . ? N1 C5 C6 C7 155.9(3) . . . . ? C5 C6 C7 O6 80.4(3) . . . . ? C5 C6 C7 C8 -37.6(3) . . . . ? C5 O1 C8 C7 -3.8(4) . . . . ? C5 O1 C8 C9 121.9(4) . . . . ? O6 C7 C8 O1 -87.8(4) . . . . ? C6 C7 C8 O1 26.3(4) . . . . ? O6 C7 C8 C9 150.1(4) . . . . ? C6 C7 C8 C9 -95.8(5) . . . . ? O1 C8 C9 O7 -70.6(5) . . . . ? C7 C8 C9 O7 49.8(6) . . . . ? C12 N3 C11 C15 2.0(11) . . . . ? Os1 N3 C11 C15 -174.4(6) . . . . ? C12 N3 C11 C16 -178.1(7) . . . . ? Os1 N3 C11 C16 5.5(9) . . . . ? C11 N3 C12 C13 -1.8(10) . . . . ? Os1 N3 C12 C13 174.3(5) . . . . ? N3 C12 C13 C14 1.7(10) . . . . ? C12 C13 C14 C15 -1.8(10) . . . . ? C13 C14 C15 C11 2.0(11) . . . . ? N3 C11 C15 C14 -2.1(11) . . . . ? C16 C11 C15 C14 178.0(7) . . . . ? C17 N4 C16 C20 -0.5(13) . . . . ? Os1 N4 C16 C20 -179.4(6) . . . . ? C17 N4 C16 C11 177.6(7) . . . . ? Os1 N4 C16 C11 -1.3(10) . . . . ? N3 C11 C16 N4 -2.8(11) . . . . ? C15 C11 C16 N4 177.1(7) . . . . ? N3 C11 C16 C20 175.2(7) . . . . ? C15 C11 C16 C20 -4.8(13) . . . . ? C16 N4 C17 C18 0.4(12) . . . . ? Os1 N4 C17 C18 179.2(6) . . . . ? N4 C17 C18 C19 -0.2(12) . . . . ? C17 C18 C19 C20 0.1(12) . . . . ? N4 C16 C20 C19 0.4(12) . . . . ? C11 C16 C20 C19 -177.6(8) . . . . ? C18 C19 C20 C16 -0.2(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.877 _refine_diff_density_min -0.799 _refine_diff_density_rms 0.101