Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Roman Dembinski' _publ_contact_author_address ; Department of Chemistry Oakland University 2200 N. Squirrel Road Rochester Michigan U8309-4477 UNITED STATES OF AMERICA ; _publ_contact_author_email DEMBINSK@OAKLAND.EDU _publ_section_title ; Metallo-Nucleosides: Synthesis and Biological Evaluation of Hexacarbonyl Dicobalt 5-Alkynyl-2'-Deoxyuridines ; loop_ _publ_author_name 'Roman Dembinski' 'Ronald Gust' 'Srinivasarao Meneni' 'Ingo Ott' 'Arnold L. Rheingold' 'Craig D. Sergeant' ; A.Sniady ; data_oak01 _database_code_depnum_ccdc_archive 'CCDC 646479' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dicobalt hexacarbonyl 5-[(1-hydroxycyclohexyl)ethynyl]-2'-deoxyuridine ; _chemical_name_common ;Dicobalt hexacarbonyl 5-((1-hydroxycyclohexyl)ethynyl)-2'- deoxyuridine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 Co2 N2 O12' _chemical_formula_weight 636.29 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7674(9) _cell_length_b 9.3303(9) _cell_length_c 31.529(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2579.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5619 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.16 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max .12 _exptl_crystal_size_mid .09 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.911 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 22063 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 28.27 _reflns_number_total 5984 _reflns_number_gt 5360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0334P)^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 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 0.010(12) _refine_ls_number_reflns 5984 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _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 Co1 Co 0.26173(4) 0.15988(4) 0.870401(11) 0.01661(9) Uani 1 1 d . . . Co2 Co 0.47186(4) 0.20970(4) 0.820435(11) 0.01691(9) Uani 1 1 d . . . O2 O 0.8369(2) 0.3404(2) 1.01356(6) 0.0190(4) Uani 1 1 d . . . O4 O 0.5022(2) 0.5532(2) 0.92431(6) 0.0230(5) Uani 1 1 d . . . O9 O 0.2316(2) 0.5547(2) 0.88213(6) 0.0196(4) Uani 1 1 d . . . O15 O 0.0557(2) 0.2765(2) 0.93472(7) 0.0298(5) Uani 1 1 d . . . O16 O 0.3857(2) -0.1005(2) 0.91163(6) 0.0258(5) Uani 1 1 d . . . O17 O 0.0296(3) 0.0629(3) 0.80930(7) 0.0377(6) Uani 1 1 d . . . O18 O 0.6357(3) -0.0641(2) 0.83204(8) 0.0394(6) Uani 1 1 d . . . O19 O 0.3070(3) 0.2029(3) 0.73880(7) 0.0370(6) Uani 1 1 d . . . O20 O 0.7355(3) 0.3943(2) 0.80420(7) 0.0383(6) Uani 1 1 d . . . O3' O 0.7273(2) -0.30146(19) 1.00695(6) 0.0201(4) Uani 1 1 d . . . H3'A H 0.6874 -0.2823 1.0298 0.030 Uiso 1 1 calc R . . O4' O 0.8592(2) -0.0031(2) 0.94733(6) 0.0202(4) Uani 1 1 d . . . O5' O 1.0764(2) -0.2239(2) 0.91723(6) 0.0216(4) Uani 1 1 d . . . H5'D H 1.1085 -0.2877 0.9017 0.032 Uiso 1 1 calc R . . N1 N 0.7171(2) 0.1981(2) 0.96446(7) 0.0157(5) Uani 1 1 d . . . N3 N 0.6714(3) 0.4421(2) 0.96707(7) 0.0160(5) Uani 1 1 d . . . H3 H 0.6893 0.5240 0.9785 0.019 Uiso 1 1 calc R . . C2 C 0.7491(3) 0.3283(3) 0.98374(8) 0.0166(5) Uani 1 1 d . . . C4 C 0.5671(3) 0.4418(3) 0.93389(8) 0.0161(6) Uani 1 1 d . . . C5 C 0.5452(3) 0.3027(3) 0.91377(8) 0.0157(5) Uani 1 1 d . . . C6 C 0.6204(3) 0.1900(3) 0.93069(8) 0.0158(6) Uani 1 1 d . . . H6 H 0.6052 0.1005 0.9184 0.019 Uiso 1 1 calc R . . C7 C 0.4407(3) 0.2830(3) 0.87834(8) 0.0147(5) Uani 1 1 d . . . C8 C 0.3418(3) 0.3454(3) 0.85134(8) 0.0156(5) Uani 1 1 d . . . C9 C 0.2669(3) 0.4889(3) 0.84210(8) 0.0168(5) Uani 1 1 d . . . H9 H 0.3105 0.5673 0.8956 0.029 Uiso 1 1 calc R . . C10 C 0.1152(3) 0.4695(3) 0.81874(10) 0.0195(6) Uani 1 1 d . . . H10A H 0.1320 0.4110 0.7937 0.023 Uiso 1 1 calc R . . H10B H 0.0446 0.4187 0.8371 0.023 Uiso 1 1 calc R . . C11 C 0.0435(3) 0.6110(3) 0.80536(10) 0.0258(7) Uani 1 1 d . . . H11A H -0.0471 0.5922 0.7886 0.031 Uiso 1 1 calc R . . H11B H 0.0130 0.6642 0.8304 0.031 Uiso 1 1 calc R . . C12 C 0.1543(3) 0.7006(3) 0.77952(9) 0.0230(6) Uani 1 1 d . . . H12A H 0.1075 0.7917 0.7724 0.028 Uiso 1 1 calc R . . H12B H 0.1785 0.6513 0.7533 0.028 Uiso 1 1 calc R . . C13 C 0.3004(3) 0.7268(3) 0.80464(9) 0.0204(6) Uani 1 1 d . . . H13A H 0.3706 0.7835 0.7877 0.024 Uiso 1 1 calc R . . H13B H 0.2768 0.7804 0.8302 0.024 Uiso 1 1 calc R . . C14 C 0.3755(3) 0.5852(3) 0.81655(9) 0.0181(6) Uani 1 1 d . . . H14A H 0.4663 0.6041 0.8332 0.022 Uiso 1 1 calc R . . H14B H 0.4065 0.5355 0.7909 0.022 Uiso 1 1 calc R . . C15 C 0.1352(3) 0.2287(3) 0.91029(9) 0.0216(6) Uani 1 1 d . . . C16 C 0.3309(3) -0.0048(3) 0.89607(9) 0.0215(6) Uani 1 1 d . . . C17 C 0.1181(3) 0.0998(3) 0.83245(10) 0.0239(6) Uani 1 1 d . . . C18 C 0.5724(3) 0.0405(3) 0.82663(10) 0.0247(7) Uani 1 1 d . . . C19 C 0.3713(3) 0.2019(3) 0.76988(9) 0.0232(6) Uani 1 1 d . . . C20 C 0.6335(3) 0.3219(3) 0.80897(9) 0.0227(6) Uani 1 1 d . . . C1' C 0.7840(3) 0.0673(3) 0.98151(9) 0.0181(6) Uani 1 1 d . . . H1' H 0.8588 0.0921 1.0034 0.022 Uiso 1 1 calc R . . C2' C 0.6686(3) -0.0398(3) 0.99966(9) 0.0202(6) Uani 1 1 d . . . H2'A H 0.6768 -0.0454 1.0303 0.024 Uiso 1 1 calc R . . H2'B H 0.5652 -0.0129 0.9922 0.024 Uiso 1 1 calc R . . C3' C 0.7127(3) -0.1823(3) 0.97906(8) 0.0163(6) Uani 1 1 d . . . H3' H 0.6406 -0.2053 0.9563 0.020 Uiso 1 1 calc R . . C4' C 0.8689(3) -0.1508(3) 0.96031(9) 0.0184(6) Uani 1 1 d . . . H4' H 0.9456 -0.1592 0.9828 0.022 Uiso 1 1 calc R . . C5' C 0.9160(3) -0.2425(3) 0.92365(9) 0.0204(6) Uani 1 1 d . . . H5'A H 0.8936 -0.3423 0.9296 0.025 Uiso 1 1 calc R . . H5'B H 0.8606 -0.2146 0.8983 0.025 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 Co1 0.01460(19) 0.01592(17) 0.01929(19) -0.00034(14) -0.00079(15) -0.00153(15) Co2 0.01513(18) 0.01743(18) 0.01816(18) -0.00308(15) 0.00057(15) -0.00017(15) O2 0.0188(10) 0.0177(9) 0.0204(10) 0.0010(8) -0.0048(8) -0.0002(9) O4 0.0258(12) 0.0164(10) 0.0268(11) -0.0029(8) -0.0097(9) 0.0040(9) O9 0.0198(10) 0.0205(9) 0.0186(10) -0.0023(7) -0.0013(8) 0.0055(9) O15 0.0244(11) 0.0315(12) 0.0337(12) -0.0019(10) 0.0104(9) -0.0024(10) O16 0.0259(12) 0.0225(11) 0.0289(12) 0.0047(9) -0.0041(9) -0.0005(9) O17 0.0317(13) 0.0387(14) 0.0427(14) -0.0007(11) -0.0171(11) -0.0072(12) O18 0.0389(14) 0.0256(13) 0.0537(16) -0.0026(11) 0.0024(12) 0.0101(11) O19 0.0303(12) 0.0553(16) 0.0254(12) -0.0039(11) -0.0039(10) -0.0062(12) O20 0.0262(12) 0.0341(12) 0.0548(15) -0.0072(11) 0.0107(11) -0.0102(12) O3' 0.0250(11) 0.0137(9) 0.0215(10) 0.0002(8) 0.0036(8) 0.0013(9) O4' 0.0187(10) 0.0140(9) 0.0278(11) 0.0012(8) 0.0057(8) 0.0015(8) O5' 0.0171(10) 0.0196(10) 0.0279(11) -0.0037(9) 0.0019(8) 0.0034(9) N1 0.0159(11) 0.0100(10) 0.0210(12) -0.0001(9) -0.0031(9) 0.0019(9) N3 0.0177(12) 0.0099(11) 0.0204(12) -0.0027(9) -0.0022(9) -0.0019(9) C2 0.0153(13) 0.0168(13) 0.0176(13) -0.0004(10) 0.0021(11) -0.0013(12) C4 0.0166(14) 0.0166(14) 0.0150(13) -0.0004(10) 0.0013(11) -0.0010(11) C5 0.0117(12) 0.0146(13) 0.0209(13) -0.0008(10) 0.0041(10) -0.0007(11) C6 0.0155(13) 0.0125(13) 0.0194(14) -0.0026(10) 0.0016(10) -0.0014(11) C7 0.0149(13) 0.0131(12) 0.0161(13) -0.0012(10) 0.0027(10) -0.0020(11) C8 0.0146(13) 0.0155(13) 0.0167(13) -0.0010(11) 0.0035(10) 0.0001(12) C9 0.0167(14) 0.0157(13) 0.0180(14) -0.0004(10) -0.0026(11) 0.0013(11) C10 0.0179(14) 0.0166(14) 0.0240(15) 0.0030(12) -0.0041(12) -0.0016(11) C11 0.0173(15) 0.0294(16) 0.0307(17) 0.0033(13) -0.0094(12) 0.0021(13) C12 0.0223(15) 0.0206(14) 0.0261(16) 0.0024(13) -0.0060(12) 0.0047(13) C13 0.0203(14) 0.0165(14) 0.0243(15) 0.0009(11) -0.0018(11) 0.0000(12) C14 0.0163(13) 0.0183(14) 0.0197(14) -0.0016(12) 0.0001(11) -0.0017(11) C15 0.0205(15) 0.0184(15) 0.0258(16) 0.0006(12) -0.0031(12) -0.0041(12) C16 0.0183(15) 0.0191(15) 0.0270(16) -0.0001(12) -0.0002(12) -0.0037(12) C17 0.0237(16) 0.0216(15) 0.0264(16) 0.0005(12) -0.0005(13) -0.0025(13) C18 0.0226(15) 0.0246(16) 0.0269(17) -0.0061(13) 0.0041(12) -0.0012(13) C19 0.0196(14) 0.0271(16) 0.0228(15) -0.0044(13) 0.0031(12) -0.0030(13) C20 0.0218(15) 0.0200(15) 0.0263(16) -0.0070(12) 0.0021(12) 0.0035(13) C1' 0.0170(14) 0.0165(13) 0.0208(14) -0.0006(11) -0.0018(11) 0.0041(11) C2' 0.0205(15) 0.0177(14) 0.0222(16) 0.0028(11) 0.0022(11) 0.0033(12) C3' 0.0170(14) 0.0121(13) 0.0199(14) 0.0000(10) -0.0009(10) 0.0002(10) C4' 0.0159(13) 0.0110(12) 0.0282(16) 0.0011(12) -0.0025(11) 0.0009(11) C5' 0.0182(14) 0.0170(14) 0.0261(15) -0.0027(11) 0.0019(11) 0.0032(11) _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 Co1 Co2 2.4682(5) . ? Co1 C7 1.961(3) . ? Co1 C8 1.962(3) . ? Co1 C15 1.796(3) . ? Co1 C17 1.825(3) . ? Co1 C16 1.840(3) . ? Co2 C8 1.963(3) . ? Co2 C7 1.969(2) . ? Co2 C18 1.818(3) . ? Co2 C19 1.823(3) . ? Co2 C20 1.799(3) . ? O2 C2 1.220(3) . ? O4 C4 1.223(3) . ? O9 C9 1.437(3) . ? O9 H9 0.8200 . ? O15 C15 1.130(3) . ? O16 C16 1.126(3) . ? O17 C17 1.120(4) . ? O18 C18 1.136(4) . ? O19 C19 1.130(3) . ? O20 C20 1.130(4) . ? O3' C3' 1.424(3) . ? O3' H3'A 0.8200 . ? O4' C1' 1.424(3) . ? O4' C4' 1.440(3) . ? O5' C5' 1.431(3) . ? O5' H5'D 0.8200 . ? N1 C2 1.387(3) . ? N1 C6 1.363(3) . ? N1 C1' 1.456(3) . ? N3 C2 1.367(3) . ? N3 C4 1.389(3) . ? N3 H3 0.8600 . ? C4 C5 1.457(4) . ? C5 C6 1.352(4) . ? C5 C7 1.456(4) . ? C6 H6 0.9300 . ? C7 C8 1.347(4) . ? C8 C9 1.520(4) . ? C9 C10 1.531(4) . ? C9 C14 1.537(4) . ? C10 C11 1.522(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.519(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.526(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.524(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C1' C2' 1.533(4) . ? C1' H1' 0.9800 . ? C2' C3' 1.529(4) . ? C2' H2'A 0.9700 . ? C2' H2'B 0.9700 . ? C3' C4' 1.520(4) . ? C3' H3' 0.9800 . ? C4' C5' 1.497(4) . ? C4' H4' 0.9800 . ? C5' H5'A 0.9700 . ? C5' H5'B 0.9700 . ? 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 C7 Co1 Co2 51.23(7) . . ? C8 Co1 Co2 51.04(8) . . ? C15 Co1 Co2 147.22(9) . . ? C16 Co1 Co2 101.07(9) . . ? C17 Co1 Co2 98.88(10) . . ? C7 Co1 C8 40.18(11) . . ? C7 Co1 C15 101.28(12) . . ? C7 Co1 C16 99.75(12) . . ? C7 Co1 C17 144.66(12) . . ? C8 Co1 C15 96.89(12) . . ? C8 Co1 C16 138.91(12) . . ? C8 Co1 C17 108.48(12) . . ? C15 Co1 C16 101.21(13) . . ? C15 Co1 C17 98.20(13) . . ? C16 Co1 C17 105.02(13) . . ? C7 Co2 Co1 50.95(7) . . ? C8 Co2 Co1 51.02(8) . . ? C18 Co2 Co1 97.46(10) . . ? C19 Co2 Co1 100.92(9) . . ? C20 Co2 Co1 145.69(9) . . ? C7 Co2 C8 40.09(10) . . ? C7 Co2 C18 105.61(12) . . ? C7 Co2 C19 139.26(12) . . ? C7 Co2 C20 95.35(12) . . ? C8 Co2 C18 142.01(12) . . ? C8 Co2 C19 100.30(12) . . ? C8 Co2 C20 100.49(12) . . ? C18 Co2 C19 107.08(14) . . ? C18 Co2 C20 98.33(13) . . ? C19 Co2 C20 103.23(13) . . ? C9 O9 H9 109.5 . . ? C3' O3' H3'A 109.5 . . ? C1' O4' C4' 104.7(2) . . ? C5' O5' H5'D 109.5 . . ? C2 N1 C6 121.1(2) . . ? C2 N1 C1' 119.4(2) . . ? C6 N1 C1' 119.5(2) . . ? C2 N3 C4 128.0(2) . . ? C2 N3 H3 116.0 . . ? C4 N3 H3 116.0 . . ? O2 C2 N1 123.1(2) . . ? O2 C2 N3 122.6(2) . . ? N3 C2 N1 114.3(2) . . ? O4 C4 N3 119.4(2) . . ? O4 C4 C5 126.0(2) . . ? N3 C4 C5 114.6(2) . . ? C4 C5 C6 117.2(2) . . ? C4 C5 C6 122.0(2) . . ? C6 C5 C7 120.8(2) . . ? C5 C6 N1 124.7(2) . . ? C5 C6 H6 117.7 . . ? N1 C6 H6 117.7 . . ? C5 C7 C8 146.6(3) . . ? C5 C7 Co1 132.48(19) . . ? C5 C7 Co2 131.93(19) . . ? C8 C7 Co1 69.95(16) . . ? C8 C7 Co2 69.72(15) . . ? Co1 C7 Co2 77.82(9) . . ? C7 C8 C9 141.3(2) . . ? C7 C8 Co1 69.87(16) . . ? C9 C8 Co1 132.95(19) . . ? C7 C8 Co2 70.19(16) . . ? C9 C8 Co2 136.40(19) . . ? Co1 C8 Co2 77.94(10) . . ? O9 C9 C8 107.5(2) . . ? O9 C9 C10 106.6(2) . . ? O9 C9 C14 110.1(2) . . ? C8 C9 C10 111.3(2) . . ? C8 C9 C14 110.3(2) . . ? C10 C9 C14 110.8(2) . . ? C9 C10 C11 112.9(2) . . ? C9 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 111.2(2) . . ? C10 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 110.3(2) . . ? C11 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C12 C13 C14 110.6(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C9 C14 C13 111.6(2) . . ? C9 C14 H14A 109.3 . . ? C9 C14 H14B 109.3 . . ? C13 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? O15 C15 Co1 177.7(3) . . ? O16 C16 Co1 173.9(3) . . ? O17 C17 Co1 179.7(3) . . ? O18 C18 Co2 177.5(3) . . ? O19 C19 Co2 177.1(3) . . ? O20 C20 Co2 176.0(3) . . ? O4' C1' N1 107.1(2) . . ? O4' C1' C2' 106.7(2) . . ? O4' C1' H1' 109.4 . . ? N1 C1' C2' 114.8(2) . . ? N1 C1' H1' 109.4 . . ? C2' C1' H1' 109.4 . . ? C1' C2' C3' 104.0(2) . . ? C1' C2' H2'A 111.0 . . ? C1' C2' H2'B 111.0 . . ? C3' C2' H2'A 111.0 . . ? C3' C2' H2'B 111.0 . . ? H2'A C2' H2'B 109.0 . . ? O3' C3' C2' 116.1(2) . . ? O3' C3' C4' 108.1(2) . . ? O3' C3' H3' 109.8 . . ? C2' C3' H3' 109.8 . . ? C4' C3' C2' 103.0(2) . . ? C4' C3' H3' 109.8 . . ? O4' C4' C3' 104.0(2) . . ? O4' C4' C5' 110.1(2) . . ? O4' C4' H4' 108.8 . . ? C3' C4' C5' 116.0(2) . . ? C3' C4' H4' 108.8 . . ? C5' C4' H4' 108.8 . . ? O5' C5' C4' 108.1(2) . . ? O5' C5' H5'A 110.1 . . ? O5' C5' H5'B 110.1 . . ? C4' C5' H5'A 110.1 . . ? C4' C5' H5'B 110.1 . . ? H5'A C5' H5'B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.804 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.083