# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sm004 _database_code_depnum_ccdc_archive 'CCDC 752052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Co N2 O2' _chemical_formula_weight 559.55 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.288(2) _cell_length_b 21.067(5) _cell_length_c 13.552(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.505(6) _cell_angle_gamma 90.00 _cell_volume 2856.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9654 _cell_measurement_theta_min 4.25 _cell_measurement_theta_max 27.55 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30120 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.12 _reflns_number_total 6835 _reflns_number_gt 5247 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0370P)^2^+1.1225P] 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_number_reflns 6835 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C -0.06950(16) 0.08887(8) 0.04244(12) 0.0248(3) Uani 1 1 d . . . C2 C 0.02787(17) 0.12282(9) 0.01022(13) 0.0294(4) Uani 1 1 d . . . H2 H 0.0301 0.1173 -0.0589 0.035 Uiso 1 1 calc R . . C3 C 0.12492(17) 0.16484(9) 0.06668(13) 0.0282(4) Uani 1 1 d . . . C4 C 0.2198(2) 0.19386(11) 0.00904(15) 0.0435(5) Uani 1 1 d . . . H4A H 0.1874 0.2360 -0.0156 0.065 Uiso 1 1 calc R . . H4B H 0.2243 0.1667 -0.0487 0.065 Uiso 1 1 calc R . . H4C H 0.3090 0.1976 0.0542 0.065 Uiso 1 1 calc R . . C5 C -0.16181(16) 0.04542(8) -0.02883(12) 0.0257(4) Uani 1 1 d . . . C6 C -0.26886(18) 0.01783(9) 0.00223(14) 0.0325(4) Uani 1 1 d . . . H6 H -0.2823 0.0273 0.0677 0.039 Uiso 1 1 calc R . . C7 C -0.35595(19) -0.02314(10) -0.06076(16) 0.0405(5) Uani 1 1 d . . . H7 H -0.4283 -0.0415 -0.0383 0.049 Uiso 1 1 calc R . . C8 C -0.3379(2) -0.03745(10) -0.15635(16) 0.0408(5) Uani 1 1 d . . . H8 H -0.3977 -0.0655 -0.1996 0.049 Uiso 1 1 calc R . . C9 C -0.2323(2) -0.01069(9) -0.18849(14) 0.0391(5) Uani 1 1 d . . . H9 H -0.2197 -0.0203 -0.2541 0.047 Uiso 1 1 calc R . . C10 C -0.14489(19) 0.03004(9) -0.12558(13) 0.0326(4) Uani 1 1 d . . . H10 H -0.0723 0.0479 -0.1484 0.039 Uiso 1 1 calc R . . C11 C 0.23359(16) 0.22165(8) 0.21648(13) 0.0256(4) Uani 1 1 d . . . C12 C 0.23017(19) 0.28580(9) 0.19129(15) 0.0350(4) Uani 1 1 d . . . H12 H 0.1629 0.3012 0.1361 0.042 Uiso 1 1 calc R . . C13 C 0.32415(19) 0.32725(9) 0.24610(16) 0.0376(4) Uani 1 1 d . . . H13 H 0.3204 0.3708 0.2276 0.045 Uiso 1 1 calc R . . C14 C 0.42378(18) 0.30680(9) 0.32746(14) 0.0329(4) Uani 1 1 d . . . C15 C 0.42403(18) 0.24306(9) 0.35372(14) 0.0324(4) Uani 1 1 d . . . H15 H 0.4901 0.2280 0.4100 0.039 Uiso 1 1 calc R . . C16 C 0.33047(17) 0.20095(9) 0.30002(13) 0.0285(4) Uani 1 1 d . . . H16 H 0.3324 0.1577 0.3203 0.034 Uiso 1 1 calc R . . C17 C 0.5279(2) 0.35221(10) 0.38512(18) 0.0474(5) Uani 1 1 d . . . H17A H 0.6070 0.3511 0.3565 0.071 Uiso 1 1 calc R . . H17B H 0.5531 0.3397 0.4567 0.071 Uiso 1 1 calc R . . H17C H 0.4912 0.3953 0.3796 0.071 Uiso 1 1 calc R . . C18 C 0.07662(16) 0.09843(8) 0.45053(12) 0.0262(4) Uani 1 1 d . . . C19 C -0.01286(17) 0.14249(9) 0.47202(13) 0.0291(4) Uani 1 1 d . . . H19 H -0.0241 0.1421 0.5396 0.035 Uiso 1 1 calc R . . C20 C -0.08973(16) 0.18802(8) 0.40666(13) 0.0271(4) Uani 1 1 d . . . C21 C -0.1772(2) 0.23095(10) 0.45246(14) 0.0373(4) Uani 1 1 d . . . H21A H -0.1614 0.2752 0.4364 0.056 Uiso 1 1 calc R . . H21B H -0.1558 0.2253 0.5263 0.056 Uiso 1 1 calc R . . H21C H -0.2713 0.2202 0.4245 0.056 Uiso 1 1 calc R . . C22 C 0.14750(17) 0.05492(8) 0.53285(13) 0.0275(4) Uani 1 1 d . . . C23 C 0.26836(19) 0.02785(9) 0.52665(15) 0.0372(4) Uani 1 1 d . . . H23 H 0.3037 0.0359 0.4690 0.045 Uiso 1 1 calc R . . C24 C 0.3379(2) -0.01080(10) 0.60399(17) 0.0474(5) Uani 1 1 d . . . H24 H 0.4213 -0.0284 0.5996 0.057 Uiso 1 1 calc R . . C25 C 0.2866(2) -0.02392(10) 0.68761(16) 0.0453(5) Uani 1 1 d . . . H25 H 0.3347 -0.0504 0.7404 0.054 Uiso 1 1 calc R . . C26 C 0.1658(2) 0.00159(10) 0.69377(15) 0.0417(5) Uani 1 1 d . . . H26 H 0.1298 -0.0076 0.7507 0.050 Uiso 1 1 calc R . . C27 C 0.09660(19) 0.04046(10) 0.61744(14) 0.0358(4) Uani 1 1 d . . . H27 H 0.0130 0.0577 0.6223 0.043 Uiso 1 1 calc R . . C28 C -0.17394(17) 0.23946(8) 0.24990(12) 0.0269(4) Uani 1 1 d . . . C29 C -0.30312(19) 0.22266(10) 0.20160(15) 0.0363(4) Uani 1 1 d . . . H29 H -0.3328 0.1802 0.2057 0.044 Uiso 1 1 calc R . . C30 C -0.3894(2) 0.26766(11) 0.14724(16) 0.0420(5) Uani 1 1 d . . . H30 H -0.4782 0.2557 0.1149 0.050 Uiso 1 1 calc R . . C31 C -0.3490(2) 0.32944(10) 0.13927(15) 0.0407(5) Uani 1 1 d . . . C32 C -0.2180(2) 0.34517(9) 0.18538(15) 0.0395(5) Uani 1 1 d . . . H32 H -0.1877 0.3873 0.1794 0.047 Uiso 1 1 calc R . . C33 C -0.13031(19) 0.30098(9) 0.23991(14) 0.0341(4) Uani 1 1 d . . . H33 H -0.0407 0.3127 0.2704 0.041 Uiso 1 1 calc R . . C34 C -0.4449(3) 0.37837(13) 0.0823(2) 0.0679(8) Uani 1 1 d . . . H34A H -0.4323 0.3825 0.0131 0.102 Uiso 1 1 calc R . . H34B H -0.4278 0.4194 0.1171 0.102 Uiso 1 1 calc R . . H34C H -0.5369 0.3650 0.0797 0.102 Uiso 1 1 calc R . . N1 N 0.13562(13) 0.17781(7) 0.16384(10) 0.0256(3) Uani 1 1 d . . . N2 N -0.08725(13) 0.19357(7) 0.31006(10) 0.0265(3) Uani 1 1 d . . . O1 O -0.08974(12) 0.09113(6) 0.13309(9) 0.0293(3) Uani 1 1 d . . . O2 O 0.10794(12) 0.09213(6) 0.36369(9) 0.0295(3) Uani 1 1 d . . . Co1 Co 0.01950(2) 0.138127(12) 0.243164(16) 0.02614(8) 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 C1 0.0275(8) 0.0300(9) 0.0169(8) 0.0017(7) 0.0052(6) 0.0062(7) C2 0.0341(9) 0.0399(10) 0.0151(8) 0.0000(7) 0.0078(7) 0.0003(8) C3 0.0285(8) 0.0349(10) 0.0226(9) 0.0030(7) 0.0090(7) 0.0010(7) C4 0.0472(12) 0.0596(14) 0.0287(10) -0.0021(9) 0.0189(9) -0.0152(10) C5 0.0285(8) 0.0274(9) 0.0198(8) 0.0020(7) 0.0024(7) 0.0074(7) C6 0.0330(9) 0.0367(10) 0.0279(10) -0.0046(8) 0.0076(8) 0.0019(8) C7 0.0343(10) 0.0413(11) 0.0451(12) -0.0102(9) 0.0078(9) -0.0029(8) C8 0.0380(10) 0.0388(11) 0.0399(12) -0.0127(9) -0.0027(9) 0.0038(9) C9 0.0496(12) 0.0420(12) 0.0225(9) -0.0066(8) 0.0021(8) 0.0079(9) C10 0.0390(10) 0.0363(10) 0.0224(9) -0.0008(8) 0.0068(7) 0.0031(8) C11 0.0257(8) 0.0308(9) 0.0221(9) -0.0006(7) 0.0092(7) -0.0006(7) C12 0.0347(10) 0.0366(10) 0.0326(10) 0.0072(8) 0.0060(8) 0.0027(8) C13 0.0429(11) 0.0275(10) 0.0449(12) 0.0012(8) 0.0151(9) -0.0005(8) C14 0.0323(9) 0.0363(10) 0.0333(10) -0.0101(8) 0.0143(8) -0.0024(8) C15 0.0300(9) 0.0412(11) 0.0253(9) -0.0039(8) 0.0051(7) 0.0026(8) C16 0.0318(9) 0.0283(9) 0.0262(9) 0.0005(7) 0.0087(7) 0.0015(7) C17 0.0476(12) 0.0446(13) 0.0500(14) -0.0142(10) 0.0112(10) -0.0096(10) C18 0.0262(8) 0.0342(10) 0.0175(8) 0.0000(7) 0.0033(6) -0.0087(7) C19 0.0314(9) 0.0416(10) 0.0147(8) -0.0003(7) 0.0064(7) -0.0046(8) C20 0.0274(8) 0.0349(10) 0.0199(8) -0.0028(7) 0.0075(7) -0.0057(7) C21 0.0445(11) 0.0466(12) 0.0245(10) 0.0011(8) 0.0152(8) 0.0070(9) C22 0.0303(9) 0.0301(9) 0.0196(9) -0.0007(7) 0.0005(7) -0.0076(7) C23 0.0416(11) 0.0399(11) 0.0287(10) 0.0005(8) 0.0052(8) 0.0004(9) C24 0.0493(12) 0.0445(12) 0.0435(13) 0.0038(10) 0.0013(10) 0.0118(10) C25 0.0577(13) 0.0361(11) 0.0342(11) 0.0099(9) -0.0055(10) -0.0015(10) C26 0.0504(12) 0.0444(12) 0.0268(10) 0.0091(9) 0.0017(9) -0.0142(10) C27 0.0347(10) 0.0441(11) 0.0273(10) 0.0063(8) 0.0046(8) -0.0073(8) C28 0.0322(9) 0.0339(9) 0.0164(8) -0.0015(7) 0.0093(7) 0.0004(7) C29 0.0355(10) 0.0389(11) 0.0331(11) 0.0063(8) 0.0052(8) -0.0058(8) C30 0.0324(10) 0.0563(14) 0.0357(11) 0.0102(10) 0.0046(8) 0.0024(9) C31 0.0513(12) 0.0453(12) 0.0291(10) 0.0096(9) 0.0169(9) 0.0147(10) C32 0.0594(13) 0.0309(10) 0.0328(11) -0.0016(8) 0.0204(10) -0.0005(9) C33 0.0397(10) 0.0373(10) 0.0265(10) -0.0056(8) 0.0099(8) -0.0062(8) C34 0.0751(18) 0.0631(17) 0.0674(18) 0.0278(14) 0.0204(14) 0.0303(14) N1 0.0259(7) 0.0314(8) 0.0199(7) 0.0021(6) 0.0064(6) 0.0001(6) N2 0.0282(7) 0.0338(8) 0.0179(7) -0.0009(6) 0.0063(6) -0.0015(6) O1 0.0322(6) 0.0389(7) 0.0181(6) -0.0025(5) 0.0081(5) -0.0050(5) O2 0.0325(6) 0.0383(7) 0.0183(6) 0.0014(5) 0.0072(5) 0.0006(5) Co1 0.02871(13) 0.03498(14) 0.01579(12) -0.00030(10) 0.00733(9) -0.00173(10) _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 C1 O1 1.2939(19) . ? C1 C2 1.382(2) . ? C1 C5 1.498(2) . ? C2 C3 1.417(2) . ? C2 H2 0.9500 . ? C3 N1 1.324(2) . ? C3 C4 1.514(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.394(2) . ? C5 C10 1.400(2) . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.392(2) . ? C11 C12 1.392(3) . ? C11 N1 1.429(2) . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 C15 1.389(3) . ? C14 C17 1.511(3) . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O2 1.298(2) . ? C18 C19 1.385(3) . ? C18 C22 1.496(2) . ? C19 C20 1.415(2) . ? C19 H19 0.9500 . ? C20 N2 1.320(2) . ? C20 C21 1.508(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.388(3) . ? C22 C27 1.401(2) . ? C23 C24 1.387(3) . ? C23 H23 0.9500 . ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 C26 1.375(3) . ? C25 H25 0.9500 . ? C26 C27 1.380(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.383(2) . ? C28 C33 1.388(3) . ? C28 N2 1.434(2) . ? C29 C30 1.387(3) . ? C29 H29 0.9500 . ? C30 C31 1.378(3) . ? C30 H30 0.9500 . ? C31 C32 1.387(3) . ? C31 C34 1.509(3) . ? C32 C33 1.384(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N1 Co1 1.9702(14) . ? N2 Co1 1.9640(14) . ? O1 Co1 1.9197(12) . ? O2 Co1 1.9341(12) . ? 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 O1 C1 C2 124.76(16) . . ? O1 C1 C5 114.60(14) . . ? C2 C1 C5 120.64(15) . . ? C1 C2 C3 128.60(16) . . ? C1 C2 H2 115.7 . . ? C3 C2 H2 115.7 . . ? N1 C3 C2 123.38(15) . . ? N1 C3 C4 121.06(16) . . ? C2 C3 C4 115.55(16) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 117.76(16) . . ? C6 C5 C1 119.12(15) . . ? C10 C5 C1 123.11(15) . . ? C7 C6 C5 121.10(18) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 120.23(19) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 119.56(18) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.32(18) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 121.02(18) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C16 C11 C12 118.40(16) . . ? C16 C11 N1 119.42(15) . . ? C12 C11 N1 122.03(16) . . ? C13 C12 C11 120.44(17) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.65(18) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C15 117.43(17) . . ? C13 C14 C17 121.17(18) . . ? C15 C14 C17 121.40(18) . . ? C16 C15 C14 121.70(17) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C11 120.32(17) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 C19 125.26(16) . . ? O2 C18 C22 115.65(15) . . ? C19 C18 C22 119.08(15) . . ? C18 C19 C20 128.62(16) . . ? C18 C19 H19 115.7 . . ? C20 C19 H19 115.7 . . ? N2 C20 C19 122.90(16) . . ? N2 C20 C21 120.43(16) . . ? C19 C20 C21 116.67(15) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 118.14(17) . . ? C23 C22 C18 119.62(16) . . ? C27 C22 C18 122.24(16) . . ? C24 C23 C22 120.44(19) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.62(19) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 120.14(19) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C22 121.11(19) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? C29 C28 C33 119.30(17) . . ? C29 C28 N2 119.87(16) . . ? C33 C28 N2 120.83(16) . . ? C28 C29 C30 120.10(18) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 121.30(19) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C30 C31 C32 118.01(18) . . ? C30 C31 C34 120.8(2) . . ? C32 C31 C34 121.2(2) . . ? C33 C32 C31 121.57(19) . . ? C33 C32 H32 119.2 . . ? C31 C32 H32 119.2 . . ? C32 C33 C28 119.65(18) . . ? C32 C33 H33 120.2 . . ? C28 C33 H33 120.2 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C3 N1 C11 121.00(14) . . ? C3 N1 Co1 122.34(12) . . ? C11 N1 Co1 116.66(10) . . ? C20 N2 C28 118.03(14) . . ? C20 N2 Co1 123.18(12) . . ? C28 N2 Co1 118.64(10) . . ? C1 O1 Co1 124.19(11) . . ? C18 O2 Co1 123.17(11) . . ? O1 Co1 O2 118.19(6) . . ? O1 Co1 N2 112.11(6) . . ? O2 Co1 N2 96.42(6) . . ? O1 Co1 N1 96.57(6) . . ? O2 Co1 N1 116.60(6) . . ? N2 Co1 N1 118.37(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 O1 C1 C2 C3 1.3(3) . . . . ? C5 C1 C2 C3 -178.66(17) . . . . ? C1 C2 C3 N1 0.1(3) . . . . ? C1 C2 C3 C4 178.90(18) . . . . ? O1 C1 C5 C6 7.6(2) . . . . ? C2 C1 C5 C6 -172.34(16) . . . . ? O1 C1 C5 C10 -171.30(16) . . . . ? C2 C1 C5 C10 8.7(3) . . . . ? C10 C5 C6 C7 -0.4(3) . . . . ? C1 C5 C6 C7 -179.35(16) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C6 C5 C10 C9 0.6(3) . . . . ? C1 C5 C10 C9 179.56(16) . . . . ? C16 C11 C12 C13 2.3(3) . . . . ? N1 C11 C12 C13 177.85(16) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 -1.5(3) . . . . ? C12 C13 C14 C17 178.46(18) . . . . ? C13 C14 C15 C16 1.2(3) . . . . ? C17 C14 C15 C16 -178.75(17) . . . . ? C14 C15 C16 C11 0.8(3) . . . . ? C12 C11 C16 C15 -2.6(2) . . . . ? N1 C11 C16 C15 -178.24(15) . . . . ? O2 C18 C19 C20 1.4(3) . . . . ? C22 C18 C19 C20 179.70(16) . . . . ? C18 C19 C20 N2 1.4(3) . . . . ? C18 C19 C20 C21 -178.75(18) . . . . ? O2 C18 C22 C23 22.0(2) . . . . ? C19 C18 C22 C23 -156.42(17) . . . . ? O2 C18 C22 C27 -158.37(16) . . . . ? C19 C18 C22 C27 23.2(2) . . . . ? C27 C22 C23 C24 -1.9(3) . . . . ? C18 C22 C23 C24 177.70(17) . . . . ? C22 C23 C24 C25 1.2(3) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C24 C25 C26 C27 -0.5(3) . . . . ? C25 C26 C27 C22 -0.2(3) . . . . ? C23 C22 C27 C26 1.5(3) . . . . ? C18 C22 C27 C26 -178.16(17) . . . . ? C33 C28 C29 C30 -2.6(3) . . . . ? N2 C28 C29 C30 176.95(17) . . . . ? C28 C29 C30 C31 0.5(3) . . . . ? C29 C30 C31 C32 1.5(3) . . . . ? C29 C30 C31 C34 -178.3(2) . . . . ? C30 C31 C32 C33 -1.4(3) . . . . ? C34 C31 C32 C33 178.4(2) . . . . ? C31 C32 C33 C28 -0.6(3) . . . . ? C29 C28 C33 C32 2.6(3) . . . . ? N2 C28 C33 C32 -176.93(16) . . . . ? C2 C3 N1 C11 -178.63(16) . . . . ? C4 C3 N1 C11 2.6(3) . . . . ? C2 C3 N1 Co1 1.6(2) . . . . ? C4 C3 N1 Co1 -177.19(14) . . . . ? C16 C11 N1 C3 -119.58(18) . . . . ? C12 C11 N1 C3 64.9(2) . . . . ? C16 C11 N1 Co1 60.21(18) . . . . ? C12 C11 N1 Co1 -115.31(16) . . . . ? C19 C20 N2 C28 177.19(15) . . . . ? C21 C20 N2 C28 -2.6(2) . . . . ? C19 C20 N2 Co1 1.7(2) . . . . ? C21 C20 N2 Co1 -178.13(13) . . . . ? C29 C28 N2 C20 -88.0(2) . . . . ? C33 C28 N2 C20 91.5(2) . . . . ? C29 C28 N2 Co1 87.72(18) . . . . ? C33 C28 N2 Co1 -92.75(17) . . . . ? C2 C1 O1 Co1 -4.2(2) . . . . ? C5 C1 O1 Co1 175.81(10) . . . . ? C19 C18 O2 Co1 -6.8(2) . . . . ? C22 C18 O2 Co1 174.87(10) . . . . ? C1 O1 Co1 O2 -120.46(13) . . . . ? C1 O1 Co1 N2 128.77(13) . . . . ? C1 O1 Co1 N1 4.51(14) . . . . ? C18 O2 Co1 O1 -111.86(13) . . . . ? C18 O2 Co1 N2 7.48(13) . . . . ? C18 O2 Co1 N1 133.71(12) . . . . ? C20 N2 Co1 O1 118.95(13) . . . . ? C28 N2 Co1 O1 -56.55(13) . . . . ? C20 N2 Co1 O2 -5.02(14) . . . . ? C28 N2 Co1 O2 179.47(12) . . . . ? C20 N2 Co1 N1 -129.97(13) . . . . ? C28 N2 Co1 N1 54.53(13) . . . . ? C3 N1 Co1 O1 -3.22(14) . . . . ? C11 N1 Co1 O1 177.00(11) . . . . ? C3 N1 Co1 O2 122.90(13) . . . . ? C11 N1 Co1 O2 -56.88(13) . . . . ? C3 N1 Co1 N2 -122.74(13) . . . . ? C11 N1 Co1 N2 57.48(13) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.294 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.052 data_sm001 _database_code_depnum_ccdc_archive 'CCDC 752053' #TrackingRef '3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H36 Co N2 O2' _chemical_formula_weight 587.60 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.3396(5) _cell_length_b 10.5700(3) _cell_length_c 16.4542(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.2860(10) _cell_angle_gamma 90.00 _cell_volume 3013.32(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5542 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.83 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 0.604 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_correction_T_max 0.886 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14932 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3588 _reflns_number_gt 3117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0352P)^2^+2.7235P] 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_number_reflns 3588 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.004 _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 C1 C 0.88355(8) 0.29631(13) 0.15117(8) 0.0187(3) Uani 1 1 d . . . C2 C 0.82617(8) 0.22981(15) 0.18878(9) 0.0227(3) Uani 1 1 d . . . H2 H 0.7748 0.2586 0.1784 0.027 Uiso 1 1 calc R . . C3 C 0.83520(8) 0.12382(15) 0.24100(9) 0.0214(3) Uani 1 1 d . . . C4 C 0.76133(8) 0.06055(17) 0.26581(11) 0.0324(4) Uani 1 1 d . . . H4A H 0.7739 -0.0113 0.3016 0.049 Uiso 0.50 1 calc PR . . H4B H 0.7324 0.0304 0.2172 0.049 Uiso 0.50 1 calc PR . . H4C H 0.7299 0.1216 0.2947 0.049 Uiso 0.50 1 calc PR . . H4D H 0.7169 0.1051 0.2407 0.049 Uiso 0.50 1 calc PR . . H4E H 0.7584 0.0634 0.3251 0.049 Uiso 0.50 1 calc PR . . H4F H 0.7610 -0.0277 0.2476 0.049 Uiso 0.50 1 calc PR . . C5 C 0.86247(8) 0.39594(14) 0.08993(8) 0.0191(3) Uani 1 1 d . . . C6 C 0.91542(9) 0.49110(15) 0.07373(9) 0.0244(3) Uani 1 1 d . . . H6 H 0.9636 0.4936 0.1033 0.029 Uiso 1 1 calc R . . C7 C 0.89848(10) 0.58198(16) 0.01504(10) 0.0310(4) Uani 1 1 d . . . H7 H 0.9348 0.6468 0.0049 0.037 Uiso 1 1 calc R . . C8 C 0.82848(10) 0.57851(16) -0.02907(10) 0.0328(4) Uani 1 1 d . . . H8 H 0.8171 0.6404 -0.0696 0.039 Uiso 1 1 calc R . . C9 C 0.77547(9) 0.48458(16) -0.01367(10) 0.0297(3) Uani 1 1 d . . . H9 H 0.7276 0.4819 -0.0439 0.036 Uiso 1 1 calc R . . C10 C 0.79182(8) 0.39456(15) 0.04546(9) 0.0235(3) Uani 1 1 d . . . H10 H 0.7548 0.3311 0.0561 0.028 Uiso 1 1 calc R . . C11 C 0.90494(7) -0.03748(14) 0.31243(8) 0.0182(3) Uani 1 1 d . . . C12 C 0.91040(8) -0.03424(15) 0.39784(9) 0.0220(3) Uani 1 1 d . . . C13 C 0.91558(9) -0.14878(16) 0.43956(10) 0.0274(3) Uani 1 1 d . . . H13 H 0.9186 -0.1486 0.4973 0.033 Uiso 1 1 calc R . . C14 C 0.91638(8) -0.26255(16) 0.39833(10) 0.0285(3) Uani 1 1 d . . . H14 H 0.9205 -0.3398 0.4277 0.034 Uiso 1 1 calc R . . C15 C 0.91118(8) -0.26384(15) 0.31406(10) 0.0256(3) Uani 1 1 d . . . H15 H 0.9122 -0.3424 0.2861 0.031 Uiso 1 1 calc R . . C16 C 0.90442(8) -0.15176(14) 0.26967(9) 0.0209(3) Uani 1 1 d . . . C17 C 0.90811(10) 0.08989(17) 0.44218(10) 0.0312(4) Uani 1 1 d . . . H17A H 0.8565 0.1272 0.4349 0.047 Uiso 1 1 calc R . . H17B H 0.9464 0.1475 0.4203 0.047 Uiso 1 1 calc R . . H17C H 0.9199 0.0759 0.5002 0.047 Uiso 1 1 calc R . . C18 C 0.89575(9) -0.15479(16) 0.17819(9) 0.0276(3) Uani 1 1 d . . . H18A H 0.8443 -0.1242 0.1611 0.041 Uiso 1 1 calc R . . H18B H 0.9023 -0.2417 0.1590 0.041 Uiso 1 1 calc R . . H18C H 0.9350 -0.1004 0.1550 0.041 Uiso 1 1 calc R . . N1 N 0.90274(6) 0.07949(11) 0.26775(7) 0.0184(2) Uani 1 1 d . . . O1 O 0.95690(5) 0.27864(10) 0.16401(6) 0.0230(2) Uani 1 1 d . . . Co1 Co 1.0000 0.17282(3) 0.2500 0.01750(9) Uani 1 2 d S . . 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 C1 0.0186(6) 0.0172(7) 0.0201(7) -0.0016(5) -0.0012(5) 0.0020(5) C2 0.0154(6) 0.0235(8) 0.0290(8) 0.0061(6) 0.0002(5) 0.0035(5) C3 0.0167(6) 0.0230(8) 0.0245(7) 0.0025(6) 0.0012(5) -0.0001(5) C4 0.0158(7) 0.0358(10) 0.0455(10) 0.0176(8) 0.0005(6) -0.0005(6) C5 0.0204(7) 0.0182(7) 0.0188(6) -0.0012(5) 0.0012(5) 0.0029(5) C6 0.0252(7) 0.0206(8) 0.0271(7) 0.0007(6) -0.0024(6) -0.0016(6) C7 0.0371(9) 0.0203(8) 0.0351(9) 0.0059(7) -0.0027(7) -0.0044(6) C8 0.0409(9) 0.0247(9) 0.0323(9) 0.0091(7) -0.0047(7) 0.0048(7) C9 0.0285(8) 0.0316(9) 0.0284(8) 0.0032(7) -0.0056(6) 0.0049(7) C10 0.0216(7) 0.0236(8) 0.0252(7) 0.0001(6) -0.0006(6) 0.0010(6) C11 0.0127(6) 0.0206(7) 0.0212(7) 0.0034(6) -0.0009(5) -0.0004(5) C12 0.0157(6) 0.0279(8) 0.0224(7) 0.0009(6) 0.0006(5) -0.0012(5) C13 0.0209(7) 0.0384(10) 0.0227(7) 0.0106(7) 0.0002(6) 0.0002(6) C14 0.0211(7) 0.0267(9) 0.0376(9) 0.0146(7) 0.0016(6) 0.0018(6) C15 0.0186(7) 0.0192(8) 0.0389(9) 0.0025(7) 0.0002(6) -0.0016(5) C16 0.0147(6) 0.0234(8) 0.0245(7) 0.0007(6) -0.0016(5) -0.0016(5) C17 0.0347(8) 0.0345(10) 0.0246(8) -0.0059(7) 0.0029(6) -0.0035(7) C18 0.0271(8) 0.0297(9) 0.0255(8) -0.0048(6) -0.0030(6) -0.0021(6) N1 0.0169(5) 0.0176(6) 0.0206(6) 0.0024(5) -0.0007(4) -0.0002(4) O1 0.0163(5) 0.0249(6) 0.0278(5) 0.0065(4) -0.0010(4) 0.0007(4) Co1 0.01359(13) 0.01727(15) 0.02144(14) 0.000 -0.00190(9) 0.000 _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 C1 O1 1.2945(16) . ? C1 C2 1.384(2) . ? C1 C5 1.493(2) . ? C2 C3 1.417(2) . ? C2 H2 0.9500 . ? C3 N1 1.3205(18) . ? C3 C4 1.515(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 H4D 0.9800 . ? C4 H4E 0.9800 . ? C4 H4F 0.9800 . ? C5 C6 1.395(2) . ? C5 C10 1.402(2) . ? C6 C7 1.385(2) . ? C6 H6 0.9500 . ? C7 C8 1.390(2) . ? C7 H7 0.9500 . ? C8 C9 1.383(2) . ? C8 H8 0.9500 . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.398(2) . ? C11 C12 1.405(2) . ? C11 N1 1.4381(18) . ? C12 C13 1.393(2) . ? C12 C17 1.503(2) . ? C13 C14 1.381(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.394(2) . ? C15 H15 0.9500 . ? C16 C18 1.507(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N1 Co1 1.9855(11) . ? O1 Co1 1.9306(10) . ? Co1 O1 1.9306(10) 2_755 ? Co1 N1 1.9855(11) 2_755 ? 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 O1 C1 C2 124.95(13) . . ? O1 C1 C5 115.12(12) . . ? C2 C1 C5 119.93(12) . . ? C1 C2 C3 127.49(13) . . ? C1 C2 H2 116.3 . . ? C3 C2 H2 116.3 . . ? N1 C3 C2 123.91(13) . . ? N1 C3 C4 120.10(13) . . ? C2 C3 C4 115.99(12) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4A C4 H4D 141.1 . . ? H4B C4 H4D 56.3 . . ? H4C C4 H4D 56.3 . . ? C3 C4 H4E 109.5 . . ? H4A C4 H4E 56.3 . . ? H4B C4 H4E 141.1 . . ? H4C C4 H4E 56.3 . . ? H4D C4 H4E 109.5 . . ? C3 C4 H4F 109.5 . . ? H4A C4 H4F 56.3 . . ? H4B C4 H4F 56.3 . . ? H4C C4 H4F 141.1 . . ? H4D C4 H4F 109.5 . . ? H4E C4 H4F 109.5 . . ? C6 C5 C10 118.43(14) . . ? C6 C5 C1 119.49(13) . . ? C10 C5 C1 122.03(13) . . ? C7 C6 C5 120.69(14) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.15(15) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.75(15) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.26(15) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 120.71(15) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C16 C11 C12 121.56(13) . . ? C16 C11 N1 119.08(12) . . ? C12 C11 N1 119.32(13) . . ? C13 C12 C11 118.18(14) . . ? C13 C12 C17 121.47(14) . . ? C11 C12 C17 120.33(14) . . ? C14 C13 C12 121.09(14) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.90(15) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 121.10(15) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C11 118.15(14) . . ? C15 C16 C18 120.54(14) . . ? C11 C16 C18 121.30(13) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 N1 C11 118.72(12) . . ? C3 N1 Co1 121.46(10) . . ? C11 N1 Co1 119.80(8) . . ? C1 O1 Co1 123.53(9) . . ? O1 Co1 O1 109.19(7) 2_755 . ? O1 Co1 N1 119.10(5) 2_755 . ? O1 Co1 N1 95.13(4) . . ? O1 Co1 N1 95.13(4) 2_755 2_755 ? O1 Co1 N1 119.10(5) . 2_755 ? N1 Co1 N1 120.41(7) . 2_755 ? 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 O1 C1 C2 C3 -6.8(3) . . . . ? C5 C1 C2 C3 172.46(15) . . . . ? C1 C2 C3 N1 6.6(3) . . . . ? C1 C2 C3 C4 -173.21(15) . . . . ? O1 C1 C5 C6 -23.32(19) . . . . ? C2 C1 C5 C6 157.40(14) . . . . ? O1 C1 C5 C10 154.20(13) . . . . ? C2 C1 C5 C10 -25.1(2) . . . . ? C10 C5 C6 C7 0.0(2) . . . . ? C1 C5 C6 C7 177.58(14) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C5 -0.8(2) . . . . ? C6 C5 C10 C9 0.7(2) . . . . ? C1 C5 C10 C9 -176.80(14) . . . . ? C16 C11 C12 C13 0.2(2) . . . . ? N1 C11 C12 C13 -177.45(12) . . . . ? C16 C11 C12 C17 -177.92(13) . . . . ? N1 C11 C12 C17 4.44(19) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C17 C12 C13 C14 178.93(14) . . . . ? C12 C13 C14 C15 -0.7(2) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C14 C15 C16 C11 1.6(2) . . . . ? C14 C15 C16 C18 -177.64(13) . . . . ? C12 C11 C16 C15 -1.4(2) . . . . ? N1 C11 C16 C15 176.27(12) . . . . ? C12 C11 C16 C18 177.83(13) . . . . ? N1 C11 C16 C18 -4.52(19) . . . . ? C2 C3 N1 C11 -172.62(14) . . . . ? C4 C3 N1 C11 7.2(2) . . . . ? C2 C3 N1 Co1 9.0(2) . . . . ? C4 C3 N1 Co1 -171.18(12) . . . . ? C16 C11 N1 C3 83.81(17) . . . . ? C12 C11 N1 C3 -98.49(16) . . . . ? C16 C11 N1 Co1 -97.75(13) . . . . ? C12 C11 N1 Co1 79.95(14) . . . . ? C2 C1 O1 Co1 -9.4(2) . . . . ? C5 C1 O1 Co1 171.31(9) . . . . ? C1 O1 Co1 O1 -104.98(12) . . . 2_755 ? C1 O1 Co1 N1 18.27(12) . . . . ? C1 O1 Co1 N1 147.43(11) . . . 2_755 ? C3 N1 Co1 O1 97.49(12) . . . 2_755 ? C11 N1 Co1 O1 -80.90(11) . . . 2_755 ? C3 N1 Co1 O1 -17.83(12) . . . . ? C11 N1 Co1 O1 163.78(10) . . . . ? C3 N1 Co1 N1 -146.06(12) . . . 2_755 ? C11 N1 Co1 N1 35.54(9) . . . 2_755 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.477 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.051 data_sm009 _database_code_depnum_ccdc_archive 'CCDC 752054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H36 Co N2 O2' _chemical_formula_weight 587.60 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.717(3) _cell_length_b 17.402(3) _cell_length_c 13.486(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.825(10) _cell_angle_gamma 90.00 _cell_volume 2944.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5075 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.35 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22926 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3586 _reflns_number_gt 2941 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0427P)^2^+2.6086P] 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_number_reflns 3586 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.002 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 C1 C 1.16701(13) 0.39275(9) 0.95040(13) 0.0217(3) Uani 1 1 d . . . C2 C 1.23250(13) 0.34067(10) 0.93108(13) 0.0239(3) Uani 1 1 d . . . H2 H 1.2966 0.3280 0.9912 0.029 Uiso 1 1 calc R . . C3 C 1.21555(13) 0.30377(9) 0.83220(13) 0.0225(3) Uani 1 1 d . . . C4 C 1.30639(15) 0.25982(12) 0.82607(15) 0.0327(4) Uani 1 1 d . . . H4A H 1.2809 0.2098 0.7921 0.049 Uiso 1 1 calc R . . H4B H 1.3613 0.2521 0.8993 0.049 Uiso 1 1 calc R . . H4C H 1.3366 0.2887 0.7827 0.049 Uiso 1 1 calc R . . C5 C 1.20189(14) 0.42923(10) 1.05870(13) 0.0236(3) Uani 1 1 d . . . C6 C 1.12581(15) 0.44767(10) 1.09768(14) 0.0266(4) Uani 1 1 d . . . H6 H 1.0527 0.4380 1.0543 0.032 Uiso 1 1 calc R . . C7 C 1.15513(17) 0.47993(11) 1.19874(15) 0.0327(4) Uani 1 1 d . . . H7 H 1.1023 0.4915 1.2252 0.039 Uiso 1 1 calc R . . C8 C 1.26008(18) 0.49552(12) 1.26148(15) 0.0368(5) Uani 1 1 d . . . H8 H 1.2801 0.5176 1.3314 0.044 Uiso 1 1 calc R . . C9 C 1.33630(17) 0.47893(13) 1.22259(16) 0.0392(5) Uani 1 1 d . . . H9 H 1.4089 0.4908 1.2651 0.047 Uiso 1 1 calc R . . C10 C 1.30791(15) 0.44533(11) 1.12251(15) 0.0326(4) Uani 1 1 d . . . H10 H 1.3612 0.4331 1.0969 0.039 Uiso 1 1 calc R . . C11 C 1.11566(13) 0.27883(10) 0.64562(13) 0.0222(3) Uani 1 1 d . . . C12 C 1.08047(14) 0.20478(10) 0.61331(14) 0.0267(4) Uani 1 1 d . . . H12 H 1.0647 0.1715 0.6607 0.032 Uiso 1 1 calc R . . C13 C 1.06837(14) 0.17943(10) 0.51213(15) 0.0294(4) Uani 1 1 d . . . C14 C 1.08996(14) 0.22908(11) 0.44382(14) 0.0296(4) Uani 1 1 d . . . H14 H 1.0820 0.2115 0.3743 0.035 Uiso 1 1 calc R . . C15 C 1.12277(14) 0.30359(11) 0.47382(14) 0.0277(4) Uani 1 1 d . . . C16 C 1.13626(14) 0.32785(10) 0.57609(14) 0.0257(4) Uani 1 1 d . . . H16 H 1.1599 0.3787 0.5987 0.031 Uiso 1 1 calc R . . C17 C 1.03213(19) 0.09850(12) 0.47658(18) 0.0448(5) Uani 1 1 d . . . H17A H 0.9561 0.0987 0.4286 0.067 Uiso 1 1 calc R . . H17B H 1.0437 0.0667 0.5403 0.067 Uiso 1 1 calc R . . H17C H 1.0730 0.0774 0.4377 0.067 Uiso 1 1 calc R . . C18 C 1.14303(18) 0.35772(13) 0.39815(16) 0.0387(5) Uani 1 1 d . . . H18A H 1.2130 0.3468 0.3979 0.058 Uiso 1 1 calc R . . H18B H 1.1416 0.4107 0.4221 0.058 Uiso 1 1 calc R . . H18C H 1.0878 0.3511 0.3248 0.058 Uiso 1 1 calc R . . N1 N 1.12459(11) 0.30791(8) 0.74767(11) 0.0220(3) Uani 1 1 d . . . O1 O 1.07423(9) 0.41369(7) 0.88287(9) 0.0260(3) Uani 1 1 d . . . Co1 Co 1.0000 0.359988(19) 0.7500 0.02218(10) Uani 1 2 d S . . 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 C1 0.0240(8) 0.0236(8) 0.0188(7) 0.0013(6) 0.0099(6) -0.0038(6) C2 0.0218(8) 0.0289(8) 0.0191(8) 0.0015(6) 0.0063(6) 0.0022(6) C3 0.0240(8) 0.0213(8) 0.0238(8) 0.0016(6) 0.0113(7) -0.0005(6) C4 0.0264(9) 0.0393(10) 0.0309(9) -0.0042(8) 0.0099(8) 0.0079(8) C5 0.0303(9) 0.0223(8) 0.0184(7) 0.0020(6) 0.0101(7) 0.0010(7) C6 0.0325(9) 0.0243(8) 0.0244(8) 0.0025(7) 0.0129(7) 0.0037(7) C7 0.0489(12) 0.0272(9) 0.0289(9) 0.0036(7) 0.0229(9) 0.0099(8) C8 0.0531(13) 0.0334(10) 0.0206(8) -0.0039(7) 0.0113(8) 0.0056(9) C9 0.0374(11) 0.0450(12) 0.0275(9) -0.0096(8) 0.0052(8) -0.0036(9) C10 0.0301(9) 0.0405(10) 0.0274(9) -0.0051(8) 0.0118(8) -0.0025(8) C11 0.0189(8) 0.0275(8) 0.0200(7) -0.0031(6) 0.0077(6) 0.0017(6) C12 0.0261(9) 0.0273(9) 0.0268(9) -0.0010(7) 0.0109(7) -0.0013(7) C13 0.0254(9) 0.0291(9) 0.0293(9) -0.0076(7) 0.0066(7) -0.0003(7) C14 0.0254(9) 0.0403(10) 0.0221(8) -0.0077(7) 0.0087(7) 0.0033(7) C15 0.0242(9) 0.0349(9) 0.0260(9) -0.0017(7) 0.0122(7) 0.0031(7) C16 0.0265(9) 0.0255(8) 0.0268(9) -0.0032(7) 0.0125(7) -0.0012(7) C17 0.0550(14) 0.0333(11) 0.0425(12) -0.0150(9) 0.0161(10) -0.0076(10) C18 0.0433(12) 0.0500(12) 0.0297(10) 0.0027(9) 0.0220(9) -0.0007(10) N1 0.0236(7) 0.0244(7) 0.0200(7) -0.0019(5) 0.0108(6) -0.0006(5) O1 0.0243(6) 0.0313(6) 0.0217(6) -0.0023(5) 0.0085(5) 0.0028(5) Co1 0.02000(17) 0.02825(18) 0.01897(16) 0.000 0.00858(12) 0.000 _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 C1 O1 1.283(2) . ? C1 C2 1.373(2) . ? C1 C5 1.483(2) . ? C2 C3 1.412(2) . ? C2 H2 0.9500 . ? C3 N1 1.309(2) . ? C3 C4 1.493(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.383(3) . ? C5 C10 1.387(3) . ? C6 C7 1.375(3) . ? C6 H6 0.9500 . ? C7 C8 1.370(3) . ? C7 H7 0.9500 . ? C8 C9 1.376(3) . ? C8 H8 0.9500 . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.379(2) . ? C11 C12 1.383(2) . ? C11 N1 1.424(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C13 C14 1.379(3) . ? C13 C17 1.506(3) . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.381(2) . ? C15 C18 1.495(3) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N1 Co1 1.9459(14) . ? O1 Co1 1.9096(12) . ? Co1 O1 1.9096(12) 2_756 ? Co1 N1 1.9459(14) 2_756 ? 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 O1 C1 C2 126.18(15) . . ? O1 C1 C5 114.23(15) . . ? C2 C1 C5 119.59(15) . . ? C1 C2 C3 127.48(15) . . ? C1 C2 H2 116.3 . . ? C3 C2 H2 116.3 . . ? N1 C3 C2 122.20(15) . . ? N1 C3 C4 120.23(15) . . ? C2 C3 C4 117.56(15) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 118.72(16) . . ? C6 C5 C1 118.74(16) . . ? C10 C5 C1 122.53(16) . . ? C7 C6 C5 120.53(18) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 120.42(18) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.57(18) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.38(19) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 120.35(19) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? C16 C11 C12 120.22(16) . . ? C16 C11 N1 118.42(15) . . ? C12 C11 N1 121.22(15) . . ? C13 C12 C11 119.80(17) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.21(17) . . ? C12 C13 C17 120.43(18) . . ? C14 C13 C17 120.36(17) . . ? C15 C14 C13 121.72(16) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 118.47(17) . . ? C14 C15 C18 121.40(17) . . ? C16 C15 C18 120.14(17) . . ? C11 C16 C15 120.55(17) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 N1 C11 120.12(14) . . ? C3 N1 Co1 123.10(12) . . ? C11 N1 Co1 116.60(10) . . ? C1 O1 Co1 121.81(11) . . ? O1 Co1 O1 121.40(8) . 2_756 ? O1 Co1 N1 110.59(6) . 2_756 ? O1 Co1 N1 95.98(5) 2_756 2_756 ? O1 Co1 N1 95.98(5) . . ? O1 Co1 N1 110.59(6) 2_756 . ? N1 Co1 N1 124.49(8) 2_756 . ? 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 O1 C1 C2 C3 4.9(3) . . . . ? C5 C1 C2 C3 -176.12(16) . . . . ? C1 C2 C3 N1 -9.6(3) . . . . ? C1 C2 C3 C4 169.64(17) . . . . ? O1 C1 C5 C6 32.0(2) . . . . ? C2 C1 C5 C6 -147.08(17) . . . . ? O1 C1 C5 C10 -148.21(17) . . . . ? C2 C1 C5 C10 32.7(2) . . . . ? C10 C5 C6 C7 -1.3(3) . . . . ? C1 C5 C6 C7 178.49(16) . . . . ? C5 C6 C7 C8 1.2(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 -1.5(3) . . . . ? C8 C9 C10 C5 1.3(3) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? C1 C5 C10 C9 -179.73(18) . . . . ? C16 C11 C12 C13 1.5(3) . . . . ? N1 C11 C12 C13 177.24(16) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C11 C12 C13 C17 178.84(18) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C17 C13 C14 C15 179.69(18) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C13 C14 C15 C18 -178.24(18) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? N1 C11 C16 C15 -176.28(15) . . . . ? C14 C15 C16 C11 -1.0(3) . . . . ? C18 C15 C16 C11 178.66(17) . . . . ? C2 C3 N1 C11 171.37(15) . . . . ? C4 C3 N1 C11 -7.9(2) . . . . ? C2 C3 N1 Co1 -3.6(2) . . . . ? C4 C3 N1 Co1 177.21(13) . . . . ? C16 C11 N1 C3 -90.2(2) . . . . ? C12 C11 N1 C3 94.0(2) . . . . ? C16 C11 N1 Co1 85.07(17) . . . . ? C12 C11 N1 Co1 -90.74(17) . . . . ? C2 C1 O1 Co1 12.2(2) . . . . ? C5 C1 O1 Co1 -166.85(10) . . . . ? C1 O1 Co1 O1 -137.01(14) . . . 2_756 ? C1 O1 Co1 N1 111.91(13) . . . 2_756 ? C1 O1 Co1 N1 -18.45(13) . . . . ? C3 N1 Co1 O1 14.47(14) . . . . ? C11 N1 Co1 O1 -160.64(12) . . . . ? C3 N1 Co1 O1 141.27(13) . . . 2_756 ? C11 N1 Co1 O1 -33.84(13) . . . 2_756 ? C3 N1 Co1 N1 -105.59(14) . . . 2_756 ? C11 N1 Co1 N1 79.30(11) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.296 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.053 data_sm005 _database_code_depnum_ccdc_archive 'CCDC 752055' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 Co F6 N2 O2' _chemical_formula_weight 667.50 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' F F 0.0171 0.0103 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.808(3) _cell_length_b 10.5730(10) _cell_length_c 30.606(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.456(4) _cell_angle_gamma 90.00 _cell_volume 6303.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6572 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.06 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2728 _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.679 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30353 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7546 _reflns_number_gt 5418 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0543P)^2^+5.9792P] 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_number_reflns 7546 _refine_ls_number_parameters 464 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 C1 C 0.83572(11) 0.0419(2) 0.74711(7) 0.0328(5) Uani 1 1 d . . . C2 C 0.86618(12) -0.0722(2) 0.73963(8) 0.0392(5) Uani 1 1 d . . . H2 H 0.8607 -0.1385 0.7596 0.047 Uiso 1 1 calc R . . C3 C 0.90452(12) -0.1037(2) 0.70612(8) 0.0374(5) Uani 1 1 d . . . C4 C 0.92925(16) -0.2386(3) 0.70486(11) 0.0582(8) Uani 1 1 d . . . H4A H 0.8980 -0.2859 0.6821 0.087 Uiso 1 1 calc R . . H4B H 0.9303 -0.2782 0.7339 0.087 Uiso 1 1 calc R . . H4C H 0.9755 -0.2393 0.6977 0.087 Uiso 1 1 calc R . . C5 C 0.80146(11) 0.0563(2) 0.78647(8) 0.0340(5) Uani 1 1 d . . . C6 C 0.79176(14) 0.1767(3) 0.80205(9) 0.0465(6) Uani 1 1 d . . . H6 H 0.8062 0.2479 0.7872 0.056 Uiso 1 1 calc R . . C7 C 0.76140(17) 0.1952(3) 0.83890(10) 0.0593(8) Uani 1 1 d . . . H7 H 0.7554 0.2786 0.8492 0.071 Uiso 1 1 calc R . . C8 C 0.73982(16) 0.0926(3) 0.86075(10) 0.0579(8) Uani 1 1 d . . . H8 H 0.7191 0.1050 0.8861 0.069 Uiso 1 1 calc R . . C9 C 0.74850(15) -0.0267(3) 0.84571(10) 0.0535(7) Uani 1 1 d . . . H9 H 0.7334 -0.0972 0.8606 0.064 Uiso 1 1 calc R . . C10 C 0.77902(13) -0.0462(2) 0.80892(9) 0.0433(6) Uani 1 1 d . . . H10 H 0.7847 -0.1299 0.7989 0.052 Uiso 1 1 calc R . . C11 C 0.95918(11) -0.0505(2) 0.64448(8) 0.0334(5) Uani 1 1 d . . . C12 C 0.93542(13) -0.1329(2) 0.60961(8) 0.0405(6) Uani 1 1 d . . . H12 H 0.8927 -0.1748 0.6083 0.049 Uiso 1 1 calc R . . C13 C 0.97379(14) -0.1541(3) 0.57679(9) 0.0450(6) Uani 1 1 d . . . H13 H 0.9575 -0.2110 0.5532 0.054 Uiso 1 1 calc R . . C14 C 1.03585(13) -0.0924(3) 0.57826(8) 0.0434(6) Uani 1 1 d . A . C15 C 1.05932(13) -0.0083(3) 0.61239(9) 0.0461(6) Uani 1 1 d . . . H15 H 1.1016 0.0349 0.6132 0.055 Uiso 1 1 calc R . . C16 C 1.02098(12) 0.0124(2) 0.64522(8) 0.0405(6) Uani 1 1 d . . . H16 H 1.0371 0.0702 0.6685 0.049 Uiso 1 1 calc R . . C17 C 1.07832(17) -0.1166(3) 0.54341(11) 0.0610(8) Uani 1 1 d . . . C18 C 0.96375(11) 0.3722(2) 0.65748(8) 0.0309(5) Uani 1 1 d . . . C19 C 0.92215(12) 0.3872(2) 0.61610(8) 0.0365(5) Uani 1 1 d . . . H19 H 0.9314 0.4591 0.5995 0.044 Uiso 1 1 calc R . . C20 C 0.86782(11) 0.3086(2) 0.59571(8) 0.0346(5) Uani 1 1 d . . . C21 C 0.83172(15) 0.3484(3) 0.54990(9) 0.0509(7) Uani 1 1 d . . . H21A H 0.8551 0.3108 0.5274 0.076 Uiso 1 1 calc R . . H21B H 0.8327 0.4408 0.5475 0.076 Uiso 1 1 calc R . . H21C H 0.7840 0.3193 0.5451 0.076 Uiso 1 1 calc R . . C22 C 1.02388(11) 0.4577(2) 0.67242(8) 0.0319(5) Uani 1 1 d . . . C23 C 1.06827(13) 0.4282(2) 0.71161(9) 0.0438(6) Uani 1 1 d . . . H23 H 1.0587 0.3577 0.7287 0.053 Uiso 1 1 calc R . . C24 C 1.12617(14) 0.5001(3) 0.72604(10) 0.0503(7) Uani 1 1 d . . . H24 H 1.1564 0.4774 0.7526 0.060 Uiso 1 1 calc R . . C25 C 1.14053(13) 0.6039(2) 0.70238(10) 0.0444(6) Uani 1 1 d . . . H25 H 1.1808 0.6523 0.7123 0.053 Uiso 1 1 calc R . . C26 C 1.09615(14) 0.6370(2) 0.66436(10) 0.0486(7) Uani 1 1 d . . . H26 H 1.1051 0.7103 0.6484 0.058 Uiso 1 1 calc R . . C27 C 1.03811(13) 0.5646(2) 0.64894(9) 0.0418(6) Uani 1 1 d . . . H27 H 1.0080 0.5880 0.6223 0.050 Uiso 1 1 calc R . . C28 C 0.79784(12) 0.1221(2) 0.59219(8) 0.0339(5) Uani 1 1 d . . . C29 C 0.80944(14) 0.0582(3) 0.55467(8) 0.0465(6) Uani 1 1 d . . . H29 H 0.8495 0.0760 0.5428 0.056 Uiso 1 1 calc R . . C30 C 0.76315(16) -0.0309(3) 0.53456(9) 0.0562(8) Uani 1 1 d . . . H30 H 0.7713 -0.0741 0.5088 0.067 Uiso 1 1 calc R . . C31 C 0.70517(16) -0.0574(3) 0.55172(11) 0.0577(8) Uani 1 1 d . B . C32 C 0.69384(16) 0.0034(3) 0.58951(12) 0.0608(8) Uani 1 1 d . . . H32 H 0.6541 -0.0159 0.6016 0.073 Uiso 1 1 calc R . . C33 C 0.74036(13) 0.0928(2) 0.61005(10) 0.0458(6) Uani 1 1 d . . . H33 H 0.7327 0.1338 0.6363 0.055 Uiso 1 1 calc R . . C34 C 0.6543(2) -0.1539(3) 0.53009(13) 0.0910(14) Uani 1 1 d D . . N1 N 0.91953(9) -0.01920(18) 0.67743(6) 0.0328(4) Uani 1 1 d . . . N2 N 0.84686(9) 0.20809(18) 0.61543(6) 0.0306(4) Uani 1 1 d . . . O1 O 0.83498(8) 0.14228(14) 0.72270(5) 0.0365(4) Uani 1 1 d . . . O2 O 0.95602(8) 0.28573(15) 0.68543(5) 0.0377(4) Uani 1 1 d . . . F1 F 1.1115(11) -0.2255(19) 0.5507(4) 0.183(8) Uani 0.476(17) 1 d PD A 1 F2 F 1.1255(10) -0.0348(18) 0.5413(7) 0.163(8) Uani 0.476(17) 1 d PD A 1 F3 F 1.0452(5) -0.1310(15) 0.5038(3) 0.102(5) Uani 0.476(17) 1 d PD A 1 F4 F 0.5956(3) -0.0944(7) 0.5153(4) 0.104(3) Uani 0.425(12) 1 d PD B 1 F5 F 0.6671(5) -0.2041(12) 0.4941(3) 0.166(7) Uani 0.425(12) 1 d PD B 1 F6 F 0.6381(7) -0.2404(11) 0.5549(3) 0.255(14) Uani 0.425(12) 1 d PD B 1 Co1 Co 0.887574(16) 0.15684(3) 0.676235(10) 0.03139(10) Uani 1 1 d . . . F1B F 1.1360(4) -0.1618(14) 0.5574(4) 0.122(5) Uani 0.524(17) 1 d PD A 2 F2B F 1.0891(8) -0.0099(9) 0.5228(4) 0.120(5) Uani 0.524(17) 1 d PD A 2 F3B F 1.0490(6) -0.1883(16) 0.5119(5) 0.143(6) Uani 0.524(17) 1 d PD A 2 F4B F 0.5936(3) -0.1503(9) 0.5375(4) 0.239(9) Uani 0.575(12) 1 d PD B 2 F5B F 0.6521(6) -0.1627(7) 0.48742(16) 0.155(6) Uani 0.575(12) 1 d PD B 2 F6B F 0.6763(4) -0.2687(5) 0.5430(2) 0.101(3) Uani 0.575(12) 1 d PD B 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 C1 0.0301(11) 0.0365(12) 0.0322(12) 0.0050(9) 0.0067(9) -0.0059(9) C2 0.0416(13) 0.0371(12) 0.0424(14) 0.0126(10) 0.0167(11) 0.0017(10) C3 0.0348(12) 0.0383(12) 0.0404(13) 0.0086(11) 0.0105(10) 0.0005(10) C4 0.0674(19) 0.0487(16) 0.068(2) 0.0215(14) 0.0368(16) 0.0196(14) C5 0.0302(11) 0.0405(12) 0.0321(12) 0.0054(10) 0.0077(9) -0.0017(9) C6 0.0551(16) 0.0454(15) 0.0426(14) 0.0025(12) 0.0185(12) -0.0069(12) C7 0.077(2) 0.0540(17) 0.0548(18) -0.0053(14) 0.0320(16) -0.0020(15) C8 0.0592(18) 0.075(2) 0.0465(16) 0.0078(15) 0.0289(14) 0.0035(15) C9 0.0565(17) 0.0568(17) 0.0546(17) 0.0174(14) 0.0296(14) 0.0019(13) C10 0.0433(14) 0.0420(14) 0.0492(15) 0.0107(12) 0.0209(12) 0.0005(11) C11 0.0328(12) 0.0357(12) 0.0328(12) 0.0075(10) 0.0086(9) 0.0036(9) C12 0.0367(13) 0.0433(14) 0.0409(13) -0.0004(11) 0.0053(10) -0.0027(10) C13 0.0492(15) 0.0488(14) 0.0362(13) -0.0050(12) 0.0053(11) 0.0034(12) C14 0.0422(14) 0.0533(15) 0.0371(13) 0.0058(12) 0.0141(11) 0.0092(12) C15 0.0390(14) 0.0560(16) 0.0464(15) 0.0020(13) 0.0158(12) -0.0047(12) C16 0.0361(13) 0.0467(14) 0.0400(13) -0.0006(11) 0.0103(10) -0.0049(10) C17 0.063(2) 0.078(2) 0.0475(18) 0.0014(16) 0.0234(15) 0.0121(17) C18 0.0328(11) 0.0277(11) 0.0348(12) 0.0027(9) 0.0130(9) 0.0008(8) C19 0.0380(13) 0.0369(12) 0.0362(13) 0.0113(10) 0.0110(10) -0.0012(10) C20 0.0339(12) 0.0403(12) 0.0304(11) 0.0059(9) 0.0082(9) 0.0062(9) C21 0.0582(17) 0.0519(15) 0.0388(14) 0.0117(12) -0.0019(12) 0.0030(13) C22 0.0318(11) 0.0278(10) 0.0387(12) -0.0009(9) 0.0134(9) 0.0009(9) C23 0.0449(14) 0.0407(13) 0.0451(14) 0.0051(11) 0.0061(12) -0.0095(11) C24 0.0476(15) 0.0473(15) 0.0529(16) 0.0011(13) 0.0014(13) -0.0096(12) C25 0.0380(13) 0.0365(12) 0.0613(17) -0.0116(12) 0.0157(12) -0.0076(10) C26 0.0475(15) 0.0320(13) 0.0713(19) 0.0067(12) 0.0243(14) -0.0067(11) C27 0.0389(13) 0.0357(12) 0.0522(15) 0.0096(11) 0.0119(11) 0.0001(10) C28 0.0351(12) 0.0317(11) 0.0327(12) -0.0008(9) 0.0006(9) 0.0066(9) C29 0.0494(15) 0.0530(15) 0.0349(13) -0.0049(12) 0.0020(11) 0.0096(12) C30 0.069(2) 0.0513(16) 0.0412(15) -0.0148(13) -0.0080(14) 0.0135(14) C31 0.0620(19) 0.0364(14) 0.0641(19) -0.0090(13) -0.0168(15) 0.0013(13) C32 0.0508(17) 0.0487(16) 0.083(2) -0.0084(16) 0.0119(16) -0.0143(13) C33 0.0437(14) 0.0420(14) 0.0539(16) -0.0099(12) 0.0148(12) -0.0071(11) C34 0.104(3) 0.054(2) 0.098(3) -0.016(2) -0.026(3) -0.017(2) N1 0.0301(9) 0.0370(10) 0.0321(10) 0.0029(8) 0.0079(8) -0.0026(8) N2 0.0297(9) 0.0354(9) 0.0274(9) 0.0011(8) 0.0070(7) 0.0015(8) O1 0.0445(9) 0.0338(8) 0.0338(8) 0.0055(7) 0.0140(7) -0.0025(7) O2 0.0473(9) 0.0352(8) 0.0300(8) 0.0063(7) 0.0054(7) -0.0122(7) F1 0.278(17) 0.182(12) 0.130(11) 0.078(8) 0.146(12) 0.177(12) F2 0.171(12) 0.185(14) 0.177(14) -0.107(11) 0.146(10) -0.108(11) F3 0.083(6) 0.191(12) 0.035(3) 0.004(5) 0.015(3) 0.036(7) F4 0.052(4) 0.075(5) 0.167(7) -0.036(5) -0.025(4) -0.027(3) F5 0.090(5) 0.146(9) 0.235(15) -0.153(10) -0.039(6) 0.025(6) F6 0.35(3) 0.195(16) 0.154(12) 0.092(12) -0.131(14) -0.221(16) Co1 0.03723(17) 0.03141(16) 0.02624(16) 0.00363(13) 0.00764(12) -0.00548(13) F1B 0.069(4) 0.221(15) 0.083(4) 0.012(8) 0.030(3) 0.080(6) F2B 0.185(11) 0.093(6) 0.115(7) 0.037(6) 0.119(7) 0.030(7) F3B 0.147(10) 0.187(11) 0.122(10) -0.105(8) 0.093(8) -0.075(8) F4B 0.092(6) 0.165(11) 0.47(2) -0.202(14) 0.077(10) -0.081(6) F5B 0.268(13) 0.078(4) 0.079(5) 0.018(4) -0.078(6) -0.090(6) F6B 0.156(6) 0.047(3) 0.095(4) -0.006(2) 0.011(4) -0.039(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 C1 O1 1.297(3) . ? C1 C2 1.386(3) . ? C1 C5 1.494(3) . ? C2 C3 1.422(3) . ? C2 H2 0.9500 . ? C3 N1 1.324(3) . ? C3 C4 1.511(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.385(3) . ? C5 C10 1.399(3) . ? C6 C7 1.385(4) . ? C6 H6 0.9500 . ? C7 C8 1.383(4) . ? C7 H7 0.9500 . ? C8 C9 1.363(4) . ? C8 H8 0.9500 . ? C9 C10 1.387(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.390(3) . ? C11 C12 1.392(3) . ? C11 N1 1.425(3) . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.386(4) . ? C14 C17 1.496(4) . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 F1B 1.241(7) . ? C17 F3 1.278(8) . ? C17 F3B 1.280(9) . ? C17 F2 1.284(9) . ? C17 F1 1.324(12) . ? C17 F2B 1.329(9) . ? C18 O2 1.280(3) . ? C18 C19 1.389(3) . ? C18 C22 1.499(3) . ? C19 C20 1.412(3) . ? C19 H19 0.9500 . ? C20 N2 1.326(3) . ? C20 C21 1.513(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.388(3) . ? C22 C27 1.396(3) . ? C23 C24 1.380(3) . ? C23 H23 0.9500 . ? C24 C25 1.373(4) . ? C24 H24 0.9500 . ? C25 C26 1.370(4) . ? C25 H25 0.9500 . ? C26 C27 1.391(4) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C33 1.385(4) . ? C28 C29 1.387(3) . ? C28 N2 1.423(3) . ? C29 C30 1.380(4) . ? C29 H29 0.9500 . ? C30 C31 1.376(5) . ? C30 H30 0.9500 . ? C31 C32 1.377(4) . ? C31 C34 1.500(4) . ? C32 C33 1.388(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 F6 1.267(6) . ? C34 F4B 1.264(6) . ? C34 F5B 1.302(6) . ? C34 F5 1.288(6) . ? C34 F6B 1.325(6) . ? C34 F4 1.328(6) . ? N1 Co1 1.9642(19) . ? N2 Co1 1.9654(18) . ? O1 Co1 1.9156(16) . ? O2 Co1 1.9067(15) . ? 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 O1 C1 C2 125.2(2) . . ? O1 C1 C5 114.9(2) . . ? C2 C1 C5 119.8(2) . . ? C1 C2 C3 128.9(2) . . ? C1 C2 H2 115.5 . . ? C3 C2 H2 115.5 . . ? N1 C3 C2 122.3(2) . . ? N1 C3 C4 120.5(2) . . ? C2 C3 C4 117.2(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 117.8(2) . . ? C6 C5 C1 118.9(2) . . ? C10 C5 C1 123.3(2) . . ? C7 C6 C5 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 120.5(3) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.8 . . ? C16 C11 C12 119.1(2) . . ? C16 C11 N1 118.3(2) . . ? C12 C11 N1 122.3(2) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 C17 119.5(3) . . ? C13 C14 C17 120.5(3) . . ? C16 C15 C14 119.7(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 120.7(2) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? F1B C17 F3 124.3(8) . . ? F1B C17 F3B 107.2(7) . . ? F3 C17 F3B 29.6(7) . . ? F1B C17 F2 69.1(10) . . ? F3 C17 F2 106.6(8) . . ? F3B C17 F2 126.6(8) . . ? F1B C17 F1 37.7(9) . . ? F3 C17 F1 102.2(7) . . ? F3B C17 F1 75.9(8) . . ? F2 C17 F1 104.5(6) . . ? F1B C17 F2B 105.9(6) . . ? F3 C17 F2B 75.4(7) . . ? F3B C17 F2B 103.6(6) . . ? F2 C17 F2B 39.0(9) . . ? F1 C17 F2B 134.5(8) . . ? F1B C17 C14 114.9(6) . . ? F3 C17 C14 116.0(6) . . ? F3B C17 C14 113.6(6) . . ? F2 C17 C14 115.4(5) . . ? F1 C17 C14 110.7(7) . . ? F2B C17 C14 110.7(5) . . ? O2 C18 C19 124.6(2) . . ? O2 C18 C22 114.3(2) . . ? C19 C18 C22 121.1(2) . . ? C18 C19 C20 127.9(2) . . ? C18 C19 H19 116.1 . . ? C20 C19 H19 116.1 . . ? N2 C20 C19 123.2(2) . . ? N2 C20 C21 120.7(2) . . ? C19 C20 C21 116.1(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 118.1(2) . . ? C23 C22 C18 118.2(2) . . ? C27 C22 C18 123.7(2) . . ? C24 C23 C22 120.8(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C25 C24 C23 120.7(3) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C25 C24 119.3(2) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C27 120.7(2) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C26 C27 C22 120.2(2) . . ? C26 C27 H27 119.9 . . ? C22 C27 H27 119.9 . . ? C33 C28 C29 119.3(2) . . ? C33 C28 N2 118.8(2) . . ? C29 C28 N2 121.6(2) . . ? C30 C29 C28 120.4(3) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C31 C30 C29 120.1(3) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.0(3) . . ? C30 C31 C34 120.7(3) . . ? C32 C31 C34 119.3(3) . . ? C31 C32 C33 120.2(3) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C28 C33 C32 120.0(3) . . ? C28 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? F6 C34 F4B 63.9(7) . . ? F6 C34 F5B 125.7(7) . . ? F4B C34 F5B 108.8(5) . . ? F6 C34 F5 109.0(6) . . ? F4B C34 F5 120.5(8) . . ? F5B C34 F5 24.4(6) . . ? F6 C34 F6B 42.8(7) . . ? F4B C34 F6B 104.2(6) . . ? F5B C34 F6B 100.5(4) . . ? F5 C34 F6B 76.9(6) . . ? F6 C34 F4 104.1(6) . . ? F4B C34 F4 40.9(6) . . ? F5B C34 F4 79.9(6) . . ? F5 C34 F4 101.5(5) . . ? F6B C34 F4 139.1(5) . . ? F6 C34 C31 116.7(6) . . ? F4B C34 C31 118.9(5) . . ? F5B C34 C31 112.9(5) . . ? F5 C34 C31 115.9(6) . . ? F6B C34 C31 109.5(4) . . ? F4 C34 C31 107.7(4) . . ? C3 N1 C11 122.1(2) . . ? C3 N1 Co1 122.79(16) . . ? C11 N1 Co1 115.09(14) . . ? C20 N2 C28 121.77(19) . . ? C20 N2 Co1 122.92(15) . . ? C28 N2 Co1 115.01(14) . . ? C1 O1 Co1 122.87(15) . . ? C18 O2 Co1 125.45(15) . . ? O2 Co1 O1 114.57(7) . . ? O2 Co1 N1 117.15(8) . . ? O1 Co1 N1 97.28(7) . . ? O2 Co1 N2 95.81(7) . . ? O1 Co1 N2 122.70(7) . . ? N1 Co1 N2 110.76(8) . . ? 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 O1 C1 C2 C3 2.7(4) . . . . ? C5 C1 C2 C3 -176.0(2) . . . . ? C1 C2 C3 N1 3.8(4) . . . . ? C1 C2 C3 C4 -177.4(3) . . . . ? O1 C1 C5 C6 -20.1(3) . . . . ? C2 C1 C5 C6 158.8(2) . . . . ? O1 C1 C5 C10 160.6(2) . . . . ? C2 C1 C5 C10 -20.6(3) . . . . ? C10 C5 C6 C7 0.6(4) . . . . ? C1 C5 C6 C7 -178.8(3) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C5 -0.1(4) . . . . ? C6 C5 C10 C9 -0.4(4) . . . . ? C1 C5 C10 C9 179.0(2) . . . . ? C16 C11 C12 C13 1.6(4) . . . . ? N1 C11 C12 C13 175.8(2) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 -0.7(4) . . . . ? C12 C13 C14 C17 178.8(3) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C17 C14 C15 C16 -178.6(3) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C12 C11 C16 C15 -1.4(4) . . . . ? N1 C11 C16 C15 -175.8(2) . . . . ? C15 C14 C17 F1B 61.0(9) . . . . ? C13 C14 C17 F1B -118.4(9) . . . . ? C15 C14 C17 F3 -142.3(9) . . . . ? C13 C14 C17 F3 38.2(9) . . . . ? C15 C14 C17 F3B -174.9(10) . . . . ? C13 C14 C17 F3B 5.6(11) . . . . ? C15 C14 C17 F2 -16.6(15) . . . . ? C13 C14 C17 F2 163.9(15) . . . . ? C15 C14 C17 F1 101.9(13) . . . . ? C13 C14 C17 F1 -77.6(13) . . . . ? C15 C14 C17 F2B -58.9(9) . . . . ? C13 C14 C17 F2B 121.6(9) . . . . ? O2 C18 C19 C20 -4.6(4) . . . . ? C22 C18 C19 C20 174.0(2) . . . . ? C18 C19 C20 N2 3.0(4) . . . . ? C18 C19 C20 C21 -179.5(2) . . . . ? O2 C18 C22 C23 6.5(3) . . . . ? C19 C18 C22 C23 -172.2(2) . . . . ? O2 C18 C22 C27 -174.1(2) . . . . ? C19 C18 C22 C27 7.3(3) . . . . ? C27 C22 C23 C24 -2.4(4) . . . . ? C18 C22 C23 C24 177.1(2) . . . . ? C22 C23 C24 C25 1.3(4) . . . . ? C23 C24 C25 C26 0.9(4) . . . . ? C24 C25 C26 C27 -1.9(4) . . . . ? C25 C26 C27 C22 0.8(4) . . . . ? C23 C22 C27 C26 1.4(4) . . . . ? C18 C22 C27 C26 -178.1(2) . . . . ? C33 C28 C29 C30 1.9(4) . . . . ? N2 C28 C29 C30 175.6(2) . . . . ? C28 C29 C30 C31 -0.2(4) . . . . ? C29 C30 C31 C32 -1.2(4) . . . . ? C29 C30 C31 C34 179.8(3) . . . . ? C30 C31 C32 C33 0.9(5) . . . . ? C34 C31 C32 C33 179.9(3) . . . . ? C29 C28 C33 C32 -2.2(4) . . . . ? N2 C28 C33 C32 -176.1(2) . . . . ? C31 C32 C33 C28 0.8(4) . . . . ? C30 C31 C34 F6 127.5(9) . . . . ? C32 C31 C34 F6 -51.5(10) . . . . ? C30 C31 C34 F4B -159.0(8) . . . . ? C32 C31 C34 F4B 22.0(8) . . . . ? C30 C31 C34 F5B -29.7(6) . . . . ? C32 C31 C34 F5B 151.3(6) . . . . ? C30 C31 C34 F5 -3.1(8) . . . . ? C32 C31 C34 F5 177.9(7) . . . . ? C30 C31 C34 F6B 81.4(5) . . . . ? C32 C31 C34 F6B -97.6(5) . . . . ? C30 C31 C34 F4 -115.9(6) . . . . ? C32 C31 C34 F4 65.1(6) . . . . ? C2 C3 N1 C11 178.7(2) . . . . ? C4 C3 N1 C11 -0.1(4) . . . . ? C2 C3 N1 Co1 -2.6(3) . . . . ? C4 C3 N1 Co1 178.7(2) . . . . ? C16 C11 N1 C3 -119.2(2) . . . . ? C12 C11 N1 C3 66.7(3) . . . . ? C16 C11 N1 Co1 62.0(2) . . . . ? C12 C11 N1 Co1 -112.2(2) . . . . ? C19 C20 N2 C28 -172.2(2) . . . . ? C21 C20 N2 C28 10.4(3) . . . . ? C19 C20 N2 Co1 1.2(3) . . . . ? C21 C20 N2 Co1 -176.18(18) . . . . ? C33 C28 N2 C20 -127.5(2) . . . . ? C29 C28 N2 C20 58.8(3) . . . . ? C33 C28 N2 Co1 58.6(2) . . . . ? C29 C28 N2 Co1 -115.1(2) . . . . ? C2 C1 O1 Co1 -9.0(3) . . . . ? C5 C1 O1 Co1 169.77(14) . . . . ? C19 C18 O2 Co1 1.4(3) . . . . ? C22 C18 O2 Co1 -177.16(14) . . . . ? C18 O2 Co1 O1 -128.34(18) . . . . ? C18 O2 Co1 N1 118.63(18) . . . . ? C18 O2 Co1 N2 1.73(19) . . . . ? C1 O1 Co1 O2 -116.52(17) . . . . ? C1 O1 Co1 N1 7.83(18) . . . . ? C1 O1 Co1 N2 128.27(17) . . . . ? C3 N1 Co1 O2 120.24(18) . . . . ? C11 N1 Co1 O2 -60.94(17) . . . . ? C3 N1 Co1 O1 -2.22(19) . . . . ? C11 N1 Co1 O1 176.60(15) . . . . ? C3 N1 Co1 N2 -131.34(18) . . . . ? C11 N1 Co1 N2 47.49(17) . . . . ? C20 N2 Co1 O2 -2.97(18) . . . . ? C28 N2 Co1 O2 170.82(15) . . . . ? C20 N2 Co1 O1 121.23(17) . . . . ? C28 N2 Co1 O1 -64.98(17) . . . . ? C20 N2 Co1 N1 -124.92(18) . . . . ? C28 N2 Co1 N1 48.87(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.400 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.055 data_sm006 _database_code_depnum_ccdc_archive 'CCDC 752056' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Co N2 O4' _chemical_formula_weight 591.55 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4825(19) _cell_length_b 18.294(3) _cell_length_c 11.7696(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.231(6) _cell_angle_gamma 90.00 _cell_volume 2856.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6101 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 25.16 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19102 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.19 _reflns_number_total 5051 _reflns_number_gt 3318 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0823P)^2^+1.4208P] 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_number_reflns 5051 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C 0.6798(3) -0.0856(2) 0.1604(3) 0.0282(9) Uani 1 1 d . . . C2 C 0.5968(3) -0.0428(2) 0.1713(3) 0.0300(9) Uani 1 1 d . . . H2 H 0.5456 -0.0665 0.2036 0.036 Uiso 1 1 calc R . . C3 C 0.5788(3) 0.0307(2) 0.1406(3) 0.0287(9) Uani 1 1 d . . . C4 C 0.4774(3) 0.0614(2) 0.1522(4) 0.0362(10) Uani 1 1 d . . . H4A H 0.4867 0.1052 0.2009 0.054 Uiso 1 1 calc R . . H4B H 0.4394 0.0248 0.1875 0.054 Uiso 1 1 calc R . . H4C H 0.4400 0.0743 0.0756 0.054 Uiso 1 1 calc R . . C5 C 0.6875(3) -0.1620(2) 0.2055(3) 0.0286(9) Uani 1 1 d . . . C6 C 0.7458(3) -0.2124(2) 0.1609(4) 0.0353(10) Uani 1 1 d . . . H6 H 0.7777 -0.1989 0.0982 0.042 Uiso 1 1 calc R . . C7 C 0.7590(3) -0.2826(2) 0.2055(4) 0.0412(11) Uani 1 1 d . . . H7 H 0.7992 -0.3167 0.1730 0.049 Uiso 1 1 calc R . . C8 C 0.7139(3) -0.3027(2) 0.2967(4) 0.0403(11) Uani 1 1 d . . . H8 H 0.7241 -0.3504 0.3286 0.048 Uiso 1 1 calc R . . C9 C 0.6537(3) -0.2534(2) 0.3420(4) 0.0395(10) Uani 1 1 d . . . H9 H 0.6217 -0.2673 0.4042 0.047 Uiso 1 1 calc R . . C10 C 0.6402(3) -0.1834(2) 0.2964(4) 0.0342(10) Uani 1 1 d . . . H10 H 0.5984 -0.1498 0.3274 0.041 Uiso 1 1 calc R . . C11 C 0.6238(3) 0.1484(2) 0.0831(3) 0.0292(9) Uani 1 1 d . . . C12 C 0.6449(3) 0.1970(2) 0.1761(4) 0.0352(10) Uani 1 1 d . . . H12 H 0.6758 0.1798 0.2501 0.042 Uiso 1 1 calc R . . C13 C 0.6208(3) 0.2693(2) 0.1602(4) 0.0378(10) Uani 1 1 d . . . H13 H 0.6346 0.3020 0.2238 0.045 Uiso 1 1 calc R . . C14 C 0.5770(3) 0.2955(2) 0.0535(4) 0.0323(9) Uani 1 1 d . . . C15 C 0.5599(3) 0.2487(2) -0.0398(4) 0.0370(10) Uani 1 1 d . . . H15 H 0.5319 0.2665 -0.1144 0.044 Uiso 1 1 calc R . . C16 C 0.5842(3) 0.1754(2) -0.0234(4) 0.0348(10) Uani 1 1 d . . . H16 H 0.5729 0.1432 -0.0877 0.042 Uiso 1 1 calc R . . C17 C 0.5122(3) 0.3961(2) -0.0634(4) 0.0474(12) Uani 1 1 d . . . H17A H 0.5618 0.3887 -0.1139 0.071 Uiso 1 1 calc R . . H17B H 0.4981 0.4484 -0.0582 0.071 Uiso 1 1 calc R . . H17C H 0.4498 0.3702 -0.0951 0.071 Uiso 1 1 calc R . . C18 C 0.8137(3) 0.0542(2) -0.1780(4) 0.0289(9) Uani 1 1 d . . . C19 C 0.9048(3) 0.0843(2) -0.1265(4) 0.0295(9) Uani 1 1 d . . . H19 H 0.9481 0.0984 -0.1781 0.035 Uiso 1 1 calc R . . C20 C 0.9426(3) 0.09701(19) -0.0089(3) 0.0271(9) Uani 1 1 d . . . C21 C 1.0476(3) 0.1276(2) 0.0212(4) 0.0359(10) Uani 1 1 d . . . H21A H 1.0442 0.1791 0.0432 0.054 Uiso 1 1 calc R . . H21B H 1.0812 0.1237 -0.0459 0.054 Uiso 1 1 calc R . . H21C H 1.0857 0.1000 0.0858 0.054 Uiso 1 1 calc R . . C22 C 0.7891(3) 0.0480(2) -0.3055(4) 0.0308(9) Uani 1 1 d . . . C23 C 0.7399(3) -0.0135(2) -0.3562(4) 0.0386(10) Uani 1 1 d . . . H23 H 0.7189 -0.0502 -0.3087 0.046 Uiso 1 1 calc R . . C24 C 0.7211(4) -0.0221(3) -0.4736(4) 0.0499(13) Uani 1 1 d . . . H24 H 0.6888 -0.0652 -0.5064 0.060 Uiso 1 1 calc R . . C25 C 0.7482(3) 0.0306(3) -0.5436(4) 0.0536(14) Uani 1 1 d . . . H25 H 0.7360 0.0239 -0.6249 0.064 Uiso 1 1 calc R . . C26 C 0.7939(3) 0.0944(3) -0.4955(4) 0.0523(13) Uani 1 1 d . . . H26 H 0.8103 0.1324 -0.5439 0.063 Uiso 1 1 calc R . . C27 C 0.8149(3) 0.1019(2) -0.3778(4) 0.0401(11) Uani 1 1 d . . . H27 H 0.8478 0.1449 -0.3452 0.048 Uiso 1 1 calc R . . C28 C 0.9276(3) 0.1076(2) 0.1878(3) 0.0284(9) Uani 1 1 d . . . C29 C 0.9140(3) 0.1800(2) 0.2173(4) 0.0412(11) Uani 1 1 d . . . H29 H 0.8813 0.2131 0.1605 0.049 Uiso 1 1 calc R . . C30 C 0.9474(4) 0.2039(2) 0.3279(4) 0.0457(12) Uani 1 1 d . . . H30 H 0.9362 0.2532 0.3477 0.055 Uiso 1 1 calc R . . C31 C 0.9969(3) 0.1572(2) 0.4104(4) 0.0375(10) Uani 1 1 d . . . C32 C 1.0122(3) 0.0850(2) 0.3820(4) 0.0380(10) Uani 1 1 d . . . H32 H 1.0467 0.0523 0.4382 0.046 Uiso 1 1 calc R . . C33 C 0.9764(3) 0.0614(2) 0.2713(4) 0.0342(10) Uani 1 1 d . . . H33 H 0.9858 0.0118 0.2521 0.041 Uiso 1 1 calc R . . C34 C 1.0770(4) 0.1391(3) 0.6069(4) 0.0560(14) Uani 1 1 d . . . H34A H 1.0355 0.0960 0.6142 0.084 Uiso 1 1 calc R . . H34B H 1.0896 0.1657 0.6803 0.084 Uiso 1 1 calc R . . H34C H 1.1413 0.1237 0.5868 0.084 Uiso 1 1 calc R . . N1 N 0.6450(2) 0.07182(17) 0.1006(3) 0.0297(8) Uani 1 1 d . . . N2 N 0.8898(2) 0.08306(16) 0.0727(3) 0.0270(7) Uani 1 1 d . . . O1 O 0.7532(2) -0.06521(14) 0.1115(2) 0.0345(7) Uani 1 1 d . . . O2 O 0.5514(2) 0.36844(15) 0.0489(3) 0.0412(7) Uani 1 1 d . . . O3 O 0.7466(2) 0.02777(14) -0.1227(2) 0.0337(7) Uani 1 1 d . . . O4 O 1.0256(3) 0.18565(17) 0.5185(3) 0.0533(9) Uani 1 1 d . . . Co1 Co 0.76082(4) 0.03010(3) 0.04308(5) 0.0305(2) 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 C1 0.032(2) 0.024(2) 0.028(2) -0.0025(17) 0.0061(17) -0.0073(17) C2 0.033(2) 0.027(2) 0.033(2) -0.0037(17) 0.0138(17) -0.0097(17) C3 0.032(2) 0.028(2) 0.027(2) -0.0060(18) 0.0071(16) -0.0062(17) C4 0.035(2) 0.036(2) 0.039(3) -0.005(2) 0.0106(19) -0.0075(18) C5 0.025(2) 0.029(2) 0.031(2) -0.0033(18) 0.0030(17) -0.0067(16) C6 0.038(2) 0.030(2) 0.041(3) -0.0041(19) 0.0136(19) -0.0092(18) C7 0.040(3) 0.028(2) 0.056(3) -0.008(2) 0.012(2) 0.0005(19) C8 0.039(2) 0.030(2) 0.051(3) 0.004(2) 0.008(2) -0.0020(19) C9 0.042(3) 0.036(2) 0.042(3) 0.004(2) 0.011(2) -0.006(2) C10 0.034(2) 0.033(2) 0.036(2) -0.0043(19) 0.0094(19) 0.0002(18) C11 0.027(2) 0.029(2) 0.034(2) -0.0052(18) 0.0131(17) -0.0045(17) C12 0.036(2) 0.036(2) 0.034(2) -0.0014(19) 0.0064(19) -0.0022(18) C13 0.049(3) 0.032(2) 0.034(3) -0.0089(19) 0.011(2) -0.0067(19) C14 0.033(2) 0.025(2) 0.041(3) -0.0005(19) 0.0134(19) -0.0044(17) C15 0.044(2) 0.032(2) 0.034(2) 0.001(2) 0.0042(19) -0.0046(19) C16 0.044(2) 0.027(2) 0.034(2) -0.0042(18) 0.0099(19) -0.0085(18) C17 0.051(3) 0.032(2) 0.057(3) 0.004(2) 0.002(2) 0.005(2) C18 0.033(2) 0.0161(18) 0.040(2) -0.0007(17) 0.0139(19) 0.0020(16) C19 0.032(2) 0.021(2) 0.038(2) 0.0026(17) 0.0143(18) -0.0014(16) C20 0.032(2) 0.0138(18) 0.037(2) 0.0006(16) 0.0108(18) 0.0013(15) C21 0.032(2) 0.032(2) 0.045(3) -0.002(2) 0.0109(19) -0.0031(18) C22 0.027(2) 0.028(2) 0.039(2) -0.0006(18) 0.0118(18) 0.0015(16) C23 0.040(2) 0.037(2) 0.041(3) -0.007(2) 0.012(2) 0.0012(19) C24 0.041(3) 0.059(3) 0.050(3) -0.022(3) 0.008(2) -0.002(2) C25 0.034(3) 0.093(4) 0.035(3) -0.008(3) 0.010(2) 0.005(3) C26 0.042(3) 0.073(4) 0.045(3) 0.016(3) 0.017(2) 0.002(3) C27 0.033(2) 0.041(3) 0.047(3) 0.005(2) 0.009(2) -0.004(2) C28 0.029(2) 0.025(2) 0.034(2) -0.0004(18) 0.0098(17) -0.0045(16) C29 0.059(3) 0.024(2) 0.038(3) 0.0010(19) 0.003(2) -0.003(2) C30 0.072(3) 0.019(2) 0.044(3) -0.005(2) 0.004(2) -0.002(2) C31 0.041(2) 0.035(2) 0.037(3) -0.005(2) 0.008(2) -0.012(2) C32 0.037(2) 0.035(2) 0.042(3) 0.006(2) 0.007(2) 0.0064(19) C33 0.042(2) 0.022(2) 0.040(3) -0.0031(19) 0.012(2) 0.0064(17) C34 0.051(3) 0.071(4) 0.043(3) -0.005(3) -0.003(2) 0.005(3) N1 0.0340(19) 0.0233(17) 0.034(2) -0.0027(15) 0.0108(15) -0.0058(14) N2 0.0302(18) 0.0204(16) 0.0316(19) -0.0030(14) 0.0086(14) -0.0032(13) O1 0.0335(15) 0.0283(15) 0.0451(18) 0.0034(13) 0.0167(13) -0.0026(12) O2 0.0498(18) 0.0280(16) 0.0469(19) -0.0015(14) 0.0117(14) -0.0011(13) O3 0.0372(16) 0.0306(15) 0.0352(16) -0.0024(13) 0.0119(12) -0.0107(12) O4 0.072(2) 0.0403(18) 0.043(2) -0.0072(16) -0.0015(17) -0.0099(16) Co1 0.0326(3) 0.0259(3) 0.0359(3) -0.0023(2) 0.0136(2) -0.0063(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 C1 O1 1.286(5) . ? C1 C2 1.390(5) . ? C1 C5 1.493(5) . ? C2 C3 1.402(5) . ? C2 H2 0.9500 . ? C3 N1 1.317(5) . ? C3 C4 1.507(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.375(6) . ? C5 C10 1.395(6) . ? C6 C7 1.386(6) . ? C6 H6 0.9500 . ? C7 C8 1.375(6) . ? C7 H7 0.9500 . ? C8 C9 1.382(6) . ? C8 H8 0.9500 . ? C9 C10 1.387(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.365(6) . ? C11 C12 1.399(6) . ? C11 N1 1.438(5) . ? C12 C13 1.368(6) . ? C12 H12 0.9500 . ? C13 C14 1.376(6) . ? C13 H13 0.9500 . ? C14 O2 1.378(5) . ? C14 C15 1.378(6) . ? C15 C16 1.385(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O2 1.425(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O3 1.298(5) . ? C18 C19 1.383(5) . ? C18 C22 1.483(6) . ? C19 C20 1.406(5) . ? C19 H19 0.9500 . ? C20 N2 1.318(5) . ? C20 C21 1.505(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.385(6) . ? C22 C27 1.387(6) . ? C23 C24 1.369(6) . ? C23 H23 0.9500 . ? C24 C25 1.359(7) . ? C24 H24 0.9500 . ? C25 C26 1.392(7) . ? C25 H25 0.9500 . ? C26 C27 1.370(6) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C33 1.372(5) . ? C28 C29 1.390(6) . ? C28 N2 1.432(5) . ? C29 C30 1.372(6) . ? C29 H29 0.9500 . ? C30 C31 1.374(6) . ? C30 H30 0.9500 . ? C31 O4 1.366(5) . ? C31 C32 1.387(6) . ? C32 C33 1.376(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 O4 1.425(6) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N1 Co1 1.964(3) . ? N2 Co1 1.967(3) . ? O1 Co1 1.931(3) . ? O3 Co1 1.927(3) . ? 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 O1 C1 C2 125.1(4) . . ? O1 C1 C5 114.8(3) . . ? C2 C1 C5 120.1(3) . . ? C1 C2 C3 128.4(4) . . ? C1 C2 H2 115.8 . . ? C3 C2 H2 115.8 . . ? N1 C3 C2 122.9(4) . . ? N1 C3 C4 120.2(4) . . ? C2 C3 C4 117.0(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 118.3(4) . . ? C6 C5 C1 120.1(4) . . ? C10 C5 C1 121.5(4) . . ? C5 C6 C7 121.4(4) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 119.9(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.8(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 120.6(4) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C16 C11 C12 118.7(4) . . ? C16 C11 N1 121.3(3) . . ? C12 C11 N1 120.0(4) . . ? C13 C12 C11 119.8(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.9(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 O2 115.9(4) . . ? C13 C14 C15 119.7(4) . . ? O2 C14 C15 124.4(4) . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 121.5(4) . . ? C11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C18 C19 124.9(4) . . ? O3 C18 C22 115.3(3) . . ? C19 C18 C22 119.7(4) . . ? C18 C19 C20 129.4(4) . . ? C18 C19 H19 115.3 . . ? C20 C19 H19 115.3 . . ? N2 C20 C19 122.5(3) . . ? N2 C20 C21 120.5(4) . . ? C19 C20 C21 117.0(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 117.8(4) . . ? C23 C22 C18 120.1(4) . . ? C27 C22 C18 122.0(4) . . ? C24 C23 C22 121.1(4) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C25 C24 C23 120.6(5) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.6(5) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 119.6(5) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C22 121.2(4) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? C33 C28 C29 118.4(4) . . ? C33 C28 N2 122.0(3) . . ? C29 C28 N2 119.6(4) . . ? C30 C29 C28 120.4(4) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.5(4) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? O4 C31 C30 116.3(4) . . ? O4 C31 C32 123.9(4) . . ? C30 C31 C32 119.8(4) . . ? C33 C32 C31 119.0(4) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C28 C33 C32 121.9(4) . . ? C28 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C3 N1 C11 118.6(3) . . ? C3 N1 Co1 122.2(3) . . ? C11 N1 Co1 118.7(2) . . ? C20 N2 C28 118.7(3) . . ? C20 N2 Co1 122.8(3) . . ? C28 N2 Co1 118.5(2) . . ? C1 O1 Co1 123.4(2) . . ? C14 O2 C17 115.4(3) . . ? C18 O3 Co1 123.1(2) . . ? C31 O4 C34 118.3(4) . . ? O3 Co1 O1 113.53(12) . . ? O3 Co1 N1 114.57(13) . . ? O1 Co1 N1 95.90(12) . . ? O3 Co1 N2 96.66(12) . . ? O1 Co1 N2 118.79(12) . . ? N1 Co1 N2 118.66(13) . . ? 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 O1 C1 C2 C3 -5.2(7) . . . . ? C5 C1 C2 C3 176.1(4) . . . . ? C1 C2 C3 N1 -3.8(7) . . . . ? C1 C2 C3 C4 174.6(4) . . . . ? O1 C1 C5 C6 -22.6(5) . . . . ? C2 C1 C5 C6 156.3(4) . . . . ? O1 C1 C5 C10 154.5(4) . . . . ? C2 C1 C5 C10 -26.6(6) . . . . ? C10 C5 C6 C7 -0.9(6) . . . . ? C1 C5 C6 C7 176.2(4) . . . . ? C5 C6 C7 C8 -0.5(6) . . . . ? C6 C7 C8 C9 1.4(7) . . . . ? C7 C8 C9 C10 -0.9(6) . . . . ? C8 C9 C10 C5 -0.5(6) . . . . ? C6 C5 C10 C9 1.4(6) . . . . ? C1 C5 C10 C9 -175.7(4) . . . . ? C16 C11 C12 C13 3.3(6) . . . . ? N1 C11 C12 C13 -177.3(4) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? C12 C13 C14 O2 176.8(4) . . . . ? C12 C13 C14 C15 -2.2(6) . . . . ? C13 C14 C15 C16 2.2(6) . . . . ? O2 C14 C15 C16 -176.6(4) . . . . ? C12 C11 C16 C15 -3.3(6) . . . . ? N1 C11 C16 C15 177.4(4) . . . . ? C14 C15 C16 C11 0.5(6) . . . . ? O3 C18 C19 C20 -4.0(6) . . . . ? C22 C18 C19 C20 178.4(4) . . . . ? C18 C19 C20 N2 -2.8(6) . . . . ? C18 C19 C20 C21 177.1(4) . . . . ? O3 C18 C22 C23 -36.9(5) . . . . ? C19 C18 C22 C23 140.8(4) . . . . ? O3 C18 C22 C27 143.9(4) . . . . ? C19 C18 C22 C27 -38.3(5) . . . . ? C27 C22 C23 C24 2.6(6) . . . . ? C18 C22 C23 C24 -176.6(4) . . . . ? C22 C23 C24 C25 -1.7(7) . . . . ? C23 C24 C25 C26 -1.1(7) . . . . ? C24 C25 C26 C27 2.8(7) . . . . ? C25 C26 C27 C22 -1.8(7) . . . . ? C23 C22 C27 C26 -0.9(6) . . . . ? C18 C22 C27 C26 178.3(4) . . . . ? C33 C28 C29 C30 -1.0(6) . . . . ? N2 C28 C29 C30 178.3(4) . . . . ? C28 C29 C30 C31 1.6(7) . . . . ? C29 C30 C31 O4 -178.8(4) . . . . ? C29 C30 C31 C32 -0.8(7) . . . . ? O4 C31 C32 C33 177.4(4) . . . . ? C30 C31 C32 C33 -0.5(6) . . . . ? C29 C28 C33 C32 -0.4(6) . . . . ? N2 C28 C33 C32 -179.6(4) . . . . ? C31 C32 C33 C28 1.1(6) . . . . ? C2 C3 N1 C11 -173.6(4) . . . . ? C4 C3 N1 C11 8.1(5) . . . . ? C2 C3 N1 Co1 15.6(5) . . . . ? C4 C3 N1 Co1 -162.7(3) . . . . ? C16 C11 N1 C3 -98.2(5) . . . . ? C12 C11 N1 C3 82.5(5) . . . . ? C16 C11 N1 Co1 73.0(4) . . . . ? C12 C11 N1 Co1 -106.3(4) . . . . ? C19 C20 N2 C28 -170.8(3) . . . . ? C21 C20 N2 C28 9.3(5) . . . . ? C19 C20 N2 Co1 9.1(5) . . . . ? C21 C20 N2 Co1 -170.8(3) . . . . ? C33 C28 N2 C20 -100.4(4) . . . . ? C29 C28 N2 C20 80.4(5) . . . . ? C33 C28 N2 Co1 79.7(4) . . . . ? C29 C28 N2 Co1 -99.5(4) . . . . ? C2 C1 O1 Co1 -0.1(5) . . . . ? C5 C1 O1 Co1 178.7(2) . . . . ? C13 C14 O2 C17 176.0(4) . . . . ? C15 C14 O2 C17 -5.1(6) . . . . ? C19 C18 O3 Co1 2.9(5) . . . . ? C22 C18 O3 Co1 -179.5(2) . . . . ? C30 C31 O4 C34 179.9(4) . . . . ? C32 C31 O4 C34 1.9(6) . . . . ? C18 O3 Co1 O1 -123.2(3) . . . . ? C18 O3 Co1 N1 128.0(3) . . . . ? C18 O3 Co1 N2 2.2(3) . . . . ? C1 O1 Co1 O3 -111.6(3) . . . . ? C1 O1 Co1 N1 8.5(3) . . . . ? C1 O1 Co1 N2 135.9(3) . . . . ? C3 N1 Co1 O3 103.2(3) . . . . ? C11 N1 Co1 O3 -67.6(3) . . . . ? C3 N1 Co1 O1 -16.0(3) . . . . ? C11 N1 Co1 O1 173.2(3) . . . . ? C3 N1 Co1 N2 -143.5(3) . . . . ? C11 N1 Co1 N2 45.7(3) . . . . ? C20 N2 Co1 O3 -8.0(3) . . . . ? C28 N2 Co1 O3 171.8(3) . . . . ? C20 N2 Co1 O1 113.5(3) . . . . ? C28 N2 Co1 O1 -66.7(3) . . . . ? C20 N2 Co1 N1 -130.8(3) . . . . ? C28 N2 Co1 N1 49.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.582 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.082 data_sm002 _database_code_depnum_ccdc_archive 'CCDC 883059' #TrackingRef '1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 Co N2 O2' _chemical_formula_weight 531.49 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2635(4) _cell_length_b 17.9930(9) _cell_length_c 16.2751(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.640(2) _cell_angle_gamma 90.00 _cell_volume 2688.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 18.72 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1108 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16124 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 22.48 _reflns_number_total 3495 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0427P)^2^+1.1850P] 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_number_reflns 3495 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C1 C 0.1993(4) 0.3408(2) 0.5629(2) 0.0388(11) Uani 1 1 d . . . C2 C 0.3061(4) 0.3777(2) 0.5275(2) 0.0393(11) Uani 1 1 d . . . H2 H 0.2989 0.4304 0.5261 0.047 Uiso 1 1 calc R . . C3 C 0.4255(4) 0.3466(2) 0.4929(3) 0.0402(11) Uani 1 1 d . . . C4 C 0.5313(5) 0.4011(2) 0.4624(3) 0.0626(14) Uani 1 1 d . . . H2A H 0.6099 0.4119 0.5073 0.094 Uiso 1 1 calc R . . H2B H 0.4800 0.4472 0.4448 0.094 Uiso 1 1 calc R . . H2C H 0.5724 0.3793 0.4154 0.094 Uiso 1 1 calc R . . C5 C 0.0831(5) 0.3827(3) 0.5999(3) 0.0444(12) Uani 1 1 d . . . C6 C -0.0135(5) 0.3444(3) 0.6422(3) 0.0644(15) Uani 1 1 d . . . H6 H -0.0036 0.2920 0.6483 0.077 Uiso 1 1 calc R . . C7 C -0.1238(6) 0.3801(3) 0.6757(3) 0.0776(17) Uani 1 1 d . . . H7 H -0.1879 0.3524 0.7049 0.093 Uiso 1 1 calc R . . C8 C -0.1411(5) 0.4556(3) 0.6670(3) 0.0672(16) Uani 1 1 d . . . H8 H -0.2186 0.4801 0.6886 0.081 Uiso 1 1 calc R . . C9 C -0.0454(6) 0.4951(3) 0.6267(3) 0.0678(15) Uani 1 1 d . . . H9 H -0.0553 0.5475 0.6212 0.081 Uiso 1 1 calc R . . C10 C 0.0661(5) 0.4587(3) 0.5941(3) 0.0598(14) Uani 1 1 d . . . H10 H 0.1325 0.4869 0.5670 0.072 Uiso 1 1 calc R . . C11 C 0.5754(4) 0.2480(2) 0.4562(3) 0.0405(11) Uani 1 1 d . . . C12 C 0.5716(5) 0.2205(2) 0.3774(3) 0.0559(13) Uani 1 1 d . . . H12 H 0.4841 0.2219 0.3397 0.067 Uiso 1 1 calc R . . C13 C 0.6984(6) 0.1904(3) 0.3535(4) 0.0698(15) Uani 1 1 d . . . H13 H 0.6976 0.1720 0.2988 0.084 Uiso 1 1 calc R . . C14 C 0.8235(6) 0.1871(3) 0.4079(4) 0.0696(17) Uani 1 1 d . . . H14 H 0.9085 0.1656 0.3911 0.083 Uiso 1 1 calc R . . C15 C 0.8273(5) 0.2141(3) 0.4854(4) 0.0743(17) Uani 1 1 d . . . H15 H 0.9153 0.2122 0.5227 0.089 Uiso 1 1 calc R . . C16 C 0.7042(5) 0.2445(3) 0.5105(3) 0.0644(15) Uani 1 1 d . . . H16 H 0.7072 0.2632 0.5653 0.077 Uiso 1 1 calc R . . C17 C 0.1991(4) 0.0662(2) 0.4435(3) 0.0358(11) Uani 1 1 d . . . C18 C 0.2781(4) 0.0247(2) 0.5048(2) 0.0383(11) Uani 1 1 d . . . H18 H 0.2663 -0.0276 0.4997 0.046 Uiso 1 1 calc R . . C19 C 0.3741(4) 0.0491(2) 0.5743(3) 0.0378(11) Uani 1 1 d . . . C20 C 0.4375(5) -0.0106(2) 0.6336(3) 0.0516(13) Uani 1 1 d . . . H20A H 0.5022 0.0122 0.6792 0.077 Uiso 0.50 1 calc PR . . H20B H 0.4928 -0.0459 0.6043 0.077 Uiso 0.50 1 calc PR . . H20C H 0.3585 -0.0368 0.6559 0.077 Uiso 0.50 1 calc PR . . H20D H 0.4001 -0.0592 0.6138 0.077 Uiso 0.50 1 calc PR . . H20E H 0.4095 -0.0011 0.6887 0.077 Uiso 0.50 1 calc PR . . H20F H 0.5439 -0.0102 0.6370 0.077 Uiso 0.50 1 calc PR . . C21 C 0.0947(4) 0.0293(2) 0.3779(3) 0.0392(11) Uani 1 1 d . . . C22 C 0.0578(4) 0.0652(3) 0.3034(3) 0.0495(12) Uani 1 1 d . . . H22 H 0.1011 0.1116 0.2934 0.059 Uiso 1 1 calc R . . C23 C -0.0445(5) 0.0328(3) 0.2421(3) 0.0652(15) Uani 1 1 d . . . H23 H -0.0700 0.0572 0.1904 0.078 Uiso 1 1 calc R . . C24 C -0.1075(5) -0.0344(4) 0.2573(4) 0.0709(17) Uani 1 1 d . . . H24 H -0.1775 -0.0558 0.2161 0.085 Uiso 1 1 calc R . . C25 C -0.0700(5) -0.0705(3) 0.3312(4) 0.0630(15) Uani 1 1 d . . . H25 H -0.1125 -0.1171 0.3411 0.076 Uiso 1 1 calc R . . C26 C 0.0303(4) -0.0383(3) 0.3913(3) 0.0488(12) Uani 1 1 d . . . H26 H 0.0556 -0.0631 0.4427 0.059 Uiso 1 1 calc R . . C27 C 0.4997(4) 0.1423(2) 0.6623(2) 0.0338(10) Uani 1 1 d . . . C28 C 0.4480(4) 0.1824(2) 0.7234(3) 0.0529(13) Uani 1 1 d . . . H28 H 0.3472 0.1940 0.7194 0.064 Uiso 1 1 calc R . . C29 C 0.5427(5) 0.2062(3) 0.7913(3) 0.0674(15) Uani 1 1 d . . . H29 H 0.5064 0.2340 0.8336 0.081 Uiso 1 1 calc R . . C30 C 0.6879(5) 0.1900(3) 0.7980(3) 0.0588(14) Uani 1 1 d . . . H30 H 0.7523 0.2059 0.8451 0.071 Uiso 1 1 calc R . . C31 C 0.7389(5) 0.1508(3) 0.7365(3) 0.0601(14) Uani 1 1 d . . . H31 H 0.8400 0.1400 0.7404 0.072 Uiso 1 1 calc R . . C32 C 0.6464(5) 0.1268(3) 0.6688(3) 0.0575(14) Uani 1 1 d . . . H32 H 0.6836 0.0993 0.6264 0.069 Uiso 1 1 calc R . . N1 N 0.4461(3) 0.27439(18) 0.4862(2) 0.0342(8) Uani 1 1 d . . . N2 N 0.4013(3) 0.12048(18) 0.59051(19) 0.0346(8) Uani 1 1 d . . . O1 O 0.1893(3) 0.26908(16) 0.56837(18) 0.0441(8) Uani 1 1 d . . . O2 O 0.2054(3) 0.13849(15) 0.43711(16) 0.0414(7) Uani 1 1 d . . . Co1 Co 0.31146(5) 0.20038(3) 0.51972(4) 0.0378(2) 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 C1 0.038(3) 0.043(3) 0.033(3) -0.003(2) -0.004(2) 0.012(2) C2 0.048(3) 0.031(2) 0.039(3) -0.009(2) 0.004(2) 0.005(2) C3 0.043(3) 0.035(3) 0.042(3) 0.001(2) 0.001(2) -0.005(2) C4 0.069(3) 0.040(3) 0.082(4) -0.005(3) 0.026(3) -0.008(3) C5 0.045(3) 0.053(3) 0.034(3) -0.004(2) -0.003(2) 0.012(3) C6 0.063(3) 0.056(3) 0.078(4) -0.013(3) 0.026(3) 0.008(3) C7 0.069(4) 0.077(4) 0.093(5) -0.020(4) 0.032(3) 0.009(3) C8 0.050(3) 0.093(5) 0.056(4) -0.024(3) 0.001(3) 0.028(3) C9 0.077(4) 0.065(4) 0.061(4) -0.008(3) 0.008(3) 0.032(3) C10 0.065(3) 0.055(3) 0.060(4) 0.003(3) 0.014(3) 0.020(3) C11 0.036(3) 0.029(3) 0.058(3) 0.006(2) 0.009(2) -0.002(2) C12 0.051(3) 0.052(3) 0.067(4) -0.015(3) 0.019(3) 0.003(2) C13 0.076(4) 0.057(4) 0.085(4) -0.015(3) 0.040(4) -0.004(3) C14 0.046(3) 0.044(3) 0.125(6) 0.013(3) 0.038(4) 0.002(3) C15 0.036(3) 0.084(4) 0.103(5) 0.009(4) 0.009(3) 0.002(3) C16 0.037(3) 0.081(4) 0.075(4) 0.004(3) 0.007(3) 0.002(3) C17 0.030(2) 0.042(3) 0.038(3) -0.003(2) 0.017(2) -0.002(2) C18 0.043(3) 0.034(3) 0.039(3) -0.005(2) 0.005(2) 0.002(2) C19 0.038(3) 0.035(3) 0.042(3) 0.004(2) 0.013(2) 0.008(2) C20 0.064(3) 0.037(3) 0.052(3) 0.006(2) 0.002(2) 0.009(2) C21 0.030(2) 0.050(3) 0.038(3) -0.007(2) 0.007(2) 0.004(2) C22 0.039(3) 0.062(3) 0.047(3) -0.011(3) 0.007(2) 0.003(2) C23 0.053(3) 0.096(5) 0.045(3) -0.010(3) 0.002(3) 0.013(3) C24 0.039(3) 0.098(5) 0.074(5) -0.037(4) 0.002(3) -0.005(3) C25 0.044(3) 0.072(4) 0.076(4) -0.026(3) 0.018(3) -0.012(3) C26 0.038(3) 0.058(3) 0.052(3) -0.013(3) 0.009(2) -0.005(2) C27 0.035(3) 0.033(2) 0.034(3) 0.003(2) 0.005(2) 0.004(2) C28 0.034(3) 0.067(3) 0.058(3) -0.026(3) 0.003(2) 0.002(2) C29 0.061(3) 0.076(4) 0.063(4) -0.037(3) 0.004(3) 0.008(3) C30 0.052(3) 0.064(3) 0.057(4) -0.013(3) -0.007(3) -0.005(3) C31 0.034(3) 0.095(4) 0.050(3) -0.007(3) -0.002(3) 0.009(3) C32 0.039(3) 0.088(4) 0.043(3) -0.012(3) 0.000(2) 0.016(3) N1 0.0250(19) 0.039(2) 0.037(2) -0.0017(16) -0.0018(16) 0.0018(16) N2 0.0293(19) 0.038(2) 0.035(2) -0.0005(17) 0.0021(16) 0.0042(16) O1 0.0353(17) 0.0411(19) 0.056(2) 0.0025(15) 0.0079(15) 0.0067(14) O2 0.0363(16) 0.0388(19) 0.0469(19) 0.0023(15) -0.0024(14) 0.0007(14) Co1 0.0301(3) 0.0350(4) 0.0475(4) 0.0012(3) 0.0026(3) 0.0027(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 C1 O1 1.298(5) . ? C1 C2 1.379(5) . ? C1 C5 1.505(6) . ? C2 C3 1.421(5) . ? C2 H2 0.9500 . ? C3 N1 1.321(5) . ? C3 C4 1.514(5) . ? C4 H2A 0.9800 . ? C4 H2B 0.9800 . ? C4 H2C 0.9800 . ? C5 C10 1.379(6) . ? C5 C6 1.383(6) . ? C6 C7 1.379(6) . ? C6 H6 0.9500 . ? C7 C8 1.373(7) . ? C7 H7 0.9500 . ? C8 C9 1.369(7) . ? C8 H8 0.9500 . ? C9 C10 1.386(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.371(6) . ? C11 C16 1.389(6) . ? C11 N1 1.433(5) . ? C12 C13 1.395(6) . ? C12 H12 0.9500 . ? C13 C14 1.363(7) . ? C13 H13 0.9500 . ? C14 C15 1.347(7) . ? C14 H14 0.9500 . ? C15 C16 1.376(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O2 1.307(5) . ? C17 C18 1.377(5) . ? C17 C21 1.498(5) . ? C18 C19 1.412(5) . ? C18 H18 0.9500 . ? C19 N2 1.329(5) . ? C19 C20 1.509(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20D 0.9800 . ? C20 H20E 0.9800 . ? C20 H20F 0.9800 . ? C21 C22 1.376(6) . ? C21 C26 1.385(6) . ? C22 C23 1.407(6) . ? C22 H22 0.9500 . ? C23 C24 1.379(7) . ? C23 H23 0.9500 . ? C24 C25 1.372(7) . ? C24 H24 0.9500 . ? C25 C26 1.383(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.367(5) . ? C27 C32 1.377(5) . ? C27 N2 1.437(5) . ? C28 C29 1.383(6) . ? C28 H28 0.9500 . ? C29 C30 1.366(6) . ? C29 H29 0.9500 . ? C30 C31 1.359(6) . ? C30 H30 0.9500 . ? C31 C32 1.373(6) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? N1 Co1 1.951(3) . ? N2 Co1 1.958(3) . ? O1 Co1 1.917(3) . ? O2 Co1 1.914(3) . ? 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 O1 C1 C2 124.7(4) . . ? O1 C1 C5 114.1(4) . . ? C2 C1 C5 121.1(4) . . ? C1 C2 C3 128.0(4) . . ? C1 C2 H2 116.0 . . ? C3 C2 H2 116.0 . . ? N1 C3 C2 123.2(4) . . ? N1 C3 C4 120.2(4) . . ? C2 C3 C4 116.6(4) . . ? C3 C4 H2A 109.5 . . ? C3 C4 H2B 109.5 . . ? H2A C4 H2B 109.5 . . ? C3 C4 H2C 109.5 . . ? H2A C4 H2C 109.5 . . ? H2B C4 H2C 109.5 . . ? C10 C5 C6 117.0(4) . . ? C10 C5 C1 123.4(4) . . ? C6 C5 C1 119.6(4) . . ? C7 C6 C5 121.8(5) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C8 C7 C6 120.2(5) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 119.3(5) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.1(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 121.7(5) . . ? C5 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C11 C16 119.5(4) . . ? C12 C11 N1 121.3(4) . . ? C16 C11 N1 119.0(4) . . ? C11 C12 C13 118.9(5) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 120.7(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.5(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.1(5) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.4(5) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? O2 C17 C18 124.9(4) . . ? O2 C17 C21 114.6(4) . . ? C18 C17 C21 120.5(4) . . ? C17 C18 C19 129.0(4) . . ? C17 C18 H18 115.5 . . ? C19 C18 H18 115.5 . . ? N2 C19 C18 122.8(4) . . ? N2 C19 C20 120.8(4) . . ? C18 C19 C20 116.2(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C20 H20D 109.5 . . ? H20A C20 H20D 141.1 . . ? H20B C20 H20D 56.3 . . ? H20C C20 H20D 56.3 . . ? C19 C20 H20E 109.5 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20C C20 H20E 56.3 . . ? H20D C20 H20E 109.5 . . ? C19 C20 H20F 109.5 . . ? H20A C20 H20F 56.3 . . ? H20B C20 H20F 56.3 . . ? H20C C20 H20F 141.1 . . ? H20D C20 H20F 109.5 . . ? H20E C20 H20F 109.5 . . ? C22 C21 C26 119.3(4) . . ? C22 C21 C17 118.8(4) . . ? C26 C21 C17 121.9(4) . . ? C21 C22 C23 119.7(5) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 119.8(5) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 120.6(5) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.3(5) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C25 C26 C21 121.3(5) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C28 C27 C32 119.2(4) . . ? C28 C27 N2 119.3(3) . . ? C32 C27 N2 121.4(4) . . ? C27 C28 C29 119.8(4) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C30 C29 C28 120.8(4) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C31 C30 C29 119.1(4) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C30 C31 C32 120.8(4) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C31 C32 C27 120.2(4) . . ? C31 C32 H32 119.9 . . ? C27 C32 H32 119.9 . . ? C3 N1 C11 119.4(3) . . ? C3 N1 Co1 123.0(3) . . ? C11 N1 Co1 117.6(2) . . ? C19 N2 C27 120.5(3) . . ? C19 N2 Co1 122.6(3) . . ? C27 N2 Co1 116.9(2) . . ? C1 O1 Co1 124.1(3) . . ? C17 O2 Co1 123.2(3) . . ? O2 Co1 O1 112.92(11) . . ? O2 Co1 N1 119.22(13) . . ? O1 Co1 N1 96.30(12) . . ? O2 Co1 N2 97.16(13) . . ? O1 Co1 N2 117.31(12) . . ? N1 Co1 N2 115.35(13) . . ? 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 O1 C1 C2 C3 -1.8(7) . . . . ? C5 C1 C2 C3 177.5(4) . . . . ? C1 C2 C3 N1 3.7(7) . . . . ? C1 C2 C3 C4 -176.7(4) . . . . ? O1 C1 C5 C10 -174.0(4) . . . . ? C2 C1 C5 C10 6.6(6) . . . . ? O1 C1 C5 C6 5.8(6) . . . . ? C2 C1 C5 C6 -173.6(4) . . . . ? C10 C5 C6 C7 1.2(7) . . . . ? C1 C5 C6 C7 -178.6(4) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? C6 C7 C8 C9 -1.8(8) . . . . ? C7 C8 C9 C10 1.1(8) . . . . ? C6 C5 C10 C9 -2.0(7) . . . . ? C1 C5 C10 C9 177.8(4) . . . . ? C8 C9 C10 C5 0.9(8) . . . . ? C16 C11 C12 C13 -0.7(7) . . . . ? N1 C11 C12 C13 -175.2(4) . . . . ? C11 C12 C13 C14 1.1(7) . . . . ? C12 C13 C14 C15 -1.1(8) . . . . ? C13 C14 C15 C16 0.8(8) . . . . ? C14 C15 C16 C11 -0.4(8) . . . . ? C12 C11 C16 C15 0.4(7) . . . . ? N1 C11 C16 C15 174.9(4) . . . . ? O2 C17 C18 C19 3.4(7) . . . . ? C21 C17 C18 C19 -175.7(4) . . . . ? C17 C18 C19 N2 0.6(7) . . . . ? C17 C18 C19 C20 176.3(4) . . . . ? O2 C17 C21 C22 23.8(5) . . . . ? C18 C17 C21 C22 -157.0(4) . . . . ? O2 C17 C21 C26 -153.6(4) . . . . ? C18 C17 C21 C26 25.6(5) . . . . ? C26 C21 C22 C23 0.0(6) . . . . ? C17 C21 C22 C23 -177.5(4) . . . . ? C21 C22 C23 C24 0.4(6) . . . . ? C22 C23 C24 C25 -0.9(7) . . . . ? C23 C24 C25 C26 1.0(7) . . . . ? C24 C25 C26 C21 -0.6(7) . . . . ? C22 C21 C26 C25 0.2(6) . . . . ? C17 C21 C26 C25 177.6(4) . . . . ? C32 C27 C28 C29 -0.7(7) . . . . ? N2 C27 C28 C29 -177.5(4) . . . . ? C27 C28 C29 C30 0.0(8) . . . . ? C28 C29 C30 C31 0.8(8) . . . . ? C29 C30 C31 C32 -0.9(8) . . . . ? C30 C31 C32 C27 0.2(8) . . . . ? C28 C27 C32 C31 0.6(7) . . . . ? N2 C27 C32 C31 177.3(4) . . . . ? C2 C3 N1 C11 -175.4(4) . . . . ? C4 C3 N1 C11 5.0(6) . . . . ? C2 C3 N1 Co1 2.1(6) . . . . ? C4 C3 N1 Co1 -177.5(3) . . . . ? C12 C11 N1 C3 -104.9(5) . . . . ? C16 C11 N1 C3 80.6(5) . . . . ? C12 C11 N1 Co1 77.5(4) . . . . ? C16 C11 N1 Co1 -96.9(4) . . . . ? C18 C19 N2 C27 179.8(3) . . . . ? C20 C19 N2 C27 4.2(6) . . . . ? C18 C19 N2 Co1 -0.1(5) . . . . ? C20 C19 N2 Co1 -175.7(3) . . . . ? C28 C27 N2 C19 -116.2(4) . . . . ? C32 C27 N2 C19 67.1(5) . . . . ? C28 C27 N2 Co1 63.8(4) . . . . ? C32 C27 N2 Co1 -113.0(4) . . . . ? C2 C1 O1 Co1 -5.6(6) . . . . ? C5 C1 O1 Co1 175.0(2) . . . . ? C18 C17 O2 Co1 -7.0(5) . . . . ? C21 C17 O2 Co1 172.3(2) . . . . ? C17 O2 Co1 O1 -117.9(3) . . . . ? C17 O2 Co1 N1 130.2(3) . . . . ? C17 O2 Co1 N2 5.8(3) . . . . ? C1 O1 Co1 O2 -117.0(3) . . . . ? C1 O1 Co1 N1 8.4(3) . . . . ? C1 O1 Co1 N2 131.2(3) . . . . ? C3 N1 Co1 O2 114.1(3) . . . . ? C11 N1 Co1 O2 -68.4(3) . . . . ? C3 N1 Co1 O1 -6.6(3) . . . . ? C11 N1 Co1 O1 170.9(3) . . . . ? C3 N1 Co1 N2 -130.9(3) . . . . ? C11 N1 Co1 N2 46.6(3) . . . . ? C19 N2 Co1 O2 -2.4(3) . . . . ? C27 N2 Co1 O2 177.7(2) . . . . ? C19 N2 Co1 O1 118.0(3) . . . . ? C27 N2 Co1 O1 -61.9(3) . . . . ? C19 N2 Co1 N1 -129.6(3) . . . . ? C27 N2 Co1 N1 50.5(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.312 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.055