# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Co N12' _chemical_formula_weight 384.27 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' 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 P21/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 11.590(3) _cell_length_b 17.073(5) _cell_length_c 17.299(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 108.696(4) _cell_angle_gamma 90.000(5) _cell_volume 3242.4(19) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 1.083 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40723 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.59 _reflns_number_total 6590 _reflns_number_gt 4810 _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^)+(0.1622P)^2^+2.7908P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6590 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.2460 _refine_ls_wR_factor_gt 0.2280 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Co1 Co 0.01659(6) 0.15095(4) 0.24141(5) 0.0311(3) Uani 1 1 d . . . Co1' Co 0.44035(6) 0.08861(4) 0.21193(5) 0.0331(3) Uani 1 1 d . . . N2 N 0.1500(4) 0.2222(3) 0.2434(3) 0.0363(10) Uani 1 1 d . . . H2N H 0.2147 0.1922 0.2428 0.044 Uiso 1 1 calc R . . N3 N -0.0822(4) 0.2237(3) 0.1600(3) 0.0331(9) Uani 1 1 d . . . N2' N 0.3125(4) 0.0155(3) 0.2172(3) 0.0369(10) Uani 1 1 d . . . H2N' H 0.2439 0.0438 0.2118 0.044 Uiso 1 1 calc R . . N4 N -0.1233(4) 0.0871(3) 0.2372(4) 0.0394(11) Uani 1 1 d . . . N1 N -0.0059(4) 0.2211(3) 0.3250(3) 0.0392(11) Uani 1 1 d . . . N1' N 0.4767(4) 0.0110(3) 0.1409(3) 0.0397(11) Uani 1 1 d . . . N5 N -0.1130(4) 0.0173(3) 0.2427(3) 0.0390(11) Uani 1 1 d . . . N4' N 0.5721(4) 0.1561(3) 0.2075(4) 0.0515(14) Uani 1 1 d . . . N3' N 0.5437(4) 0.0288(3) 0.3026(3) 0.0356(10) Uani 1 1 d . . . N7 N 0.0545(5) 0.0876(3) 0.1592(3) 0.0449(12) Uani 1 1 d . . . N5' N 0.5790(4) 0.2227(3) 0.2262(4) 0.0469(12) Uani 1 1 d . . . N7' N 0.3944(4) 0.1590(3) 0.2842(4) 0.0501(13) Uani 1 1 d . . . N10 N 0.1290(5) 0.0863(3) 0.3269(4) 0.0505(14) Uani 1 1 d . . . N10' N 0.3186(5) 0.1368(4) 0.1194(4) 0.0577(15) Uani 1 1 d . . . N8 N -0.0286(5) 0.0579(3) 0.1066(3) 0.0439(12) Uani 1 1 d . . . C8' C 0.4843(5) -0.0224(4) 0.3349(4) 0.0398(12) Uani 1 1 d . . . N11' N 0.3404(5) 0.1916(3) 0.0845(3) 0.0440(12) Uani 1 1 d . . . C7' C 0.3482(5) -0.0235(4) 0.2981(4) 0.0421(13) Uani 1 1 d . . . H7A' H 0.3193 -0.0772 0.2920 0.051 Uiso 1 1 calc R . . H7B' H 0.3116 0.0035 0.3337 0.051 Uiso 1 1 calc R . . C5 C 0.0815(6) 0.2727(4) 0.3537(4) 0.0456(14) Uani 1 1 d . . . N11 N 0.0907(5) 0.0683(3) 0.3809(4) 0.0507(13) Uani 1 1 d . . . C8 C -0.0184(6) 0.2810(4) 0.1387(4) 0.0435(13) Uani 1 1 d . . . C12' C 0.6660(5) 0.0334(4) 0.3328(4) 0.0415(13) Uani 1 1 d . . . H12' H 0.7069 0.0693 0.3106 0.050 Uiso 1 1 calc R . . C6 C 0.1869(5) 0.2669(4) 0.3210(4) 0.0481(15) Uani 1 1 d . . . H6A H 0.2131 0.3190 0.3117 0.058 Uiso 1 1 calc R . . H6B H 0.2548 0.2408 0.3606 0.058 Uiso 1 1 calc R . . C12 C -0.2041(5) 0.2248(4) 0.1333(4) 0.0437(13) Uani 1 1 d . . . H12 H -0.2467 0.1856 0.1499 0.052 Uiso 1 1 calc R . . C7 C 0.1146(6) 0.2704(4) 0.1684(4) 0.0461(14) Uani 1 1 d . . . H7A H 0.1543 0.3211 0.1800 0.055 Uiso 1 1 calc R . . H7B H 0.1408 0.2450 0.1268 0.055 Uiso 1 1 calc R . . C6' C 0.2864(5) -0.0388(4) 0.1464(4) 0.0466(14) Uani 1 1 d . . . H6A' H 0.2203 -0.0180 0.1012 0.056 Uiso 1 1 calc R . . H6B' H 0.2611 -0.0892 0.1612 0.056 Uiso 1 1 calc R . . C1' C 0.5789(5) 0.0079(4) 0.1189(4) 0.0461(14) Uani 1 1 d . . . H1' H 0.6340 0.0493 0.1327 0.055 Uiso 1 1 calc R . . C1 C -0.1028(6) 0.2201(4) 0.3530(4) 0.0485(15) Uani 1 1 d . . . H1 H -0.1647 0.1837 0.3322 0.058 Uiso 1 1 calc R . . C9 C -0.0772(7) 0.3411(4) 0.0885(4) 0.0496(15) Uani 1 1 d . . . H9 H -0.0327 0.3804 0.0737 0.059 Uiso 1 1 calc R . . C4' C 0.4201(8) -0.1133(5) 0.0793(5) 0.0605(18) Uani 1 1 d . . . H4' H 0.3654 -0.1548 0.0664 0.073 Uiso 1 1 calc R . . C5' C 0.3975(6) -0.0493(4) 0.1205(4) 0.0457(14) Uani 1 1 d . . . N6 N -0.1116(6) -0.0492(3) 0.2459(5) 0.0677(18) Uani 1 1 d . . . C11 C -0.2673(6) 0.2824(5) 0.0823(5) 0.0560(17) Uani 1 1 d . . . H11 H -0.3519 0.2813 0.0627 0.067 Uiso 1 1 calc R . . C9' C 0.5472(7) -0.0695(4) 0.3992(4) 0.0545(17) Uani 1 1 d . . . H9' H 0.5049 -0.1030 0.4229 0.065 Uiso 1 1 calc R . . N8' N 0.4620(5) 0.1679(4) 0.3542(4) 0.0587(16) Uani 1 1 d . . . N12 N 0.0559(7) 0.0475(5) 0.4320(4) 0.080(2) Uani 1 1 d . . . N6' N 0.5955(7) 0.2859(4) 0.2474(6) 0.082(2) Uani 1 1 d . . . C2' C 0.6033(6) -0.0551(5) 0.0766(5) 0.0577(18) Uani 1 1 d . . . H2' H 0.6733 -0.0559 0.0614 0.069 Uiso 1 1 calc R . . C10 C -0.2035(7) 0.3427(5) 0.0601(5) 0.0599(18) Uani 1 1 d . . . H10 H -0.2449 0.3833 0.0268 0.072 Uiso 1 1 calc R . . C4 C 0.0779(8) 0.3281(5) 0.4116(5) 0.0613(19) Uani 1 1 d . . . H4 H 0.1399 0.3648 0.4307 0.074 Uiso 1 1 calc R . . C2 C -0.1106(8) 0.2717(5) 0.4108(5) 0.066(2) Uani 1 1 d . . . H2 H -0.1763 0.2697 0.4306 0.079 Uiso 1 1 calc R . . C10' C 0.6699(7) -0.0670(4) 0.4278(5) 0.0596(18) Uani 1 1 d . . . H10' H 0.7127 -0.1010 0.4691 0.071 Uiso 1 1 calc R . . N9 N -0.1060(7) 0.0307(5) 0.0553(4) 0.074(2) Uani 1 1 d . . . C3' C 0.5237(8) -0.1156(5) 0.0575(5) 0.066(2) Uani 1 1 d . . . H3' H 0.5393 -0.1587 0.0295 0.079 Uiso 1 1 calc R . . C11' C 0.7316(6) -0.0141(4) 0.3957(4) 0.0552(17) Uani 1 1 d . . . H11' H 0.8160 -0.0105 0.4161 0.066 Uiso 1 1 calc R . . C3 C -0.0209(9) 0.3269(5) 0.4400(5) 0.073(2) Uani 1 1 d . . . H3 H -0.0266 0.3634 0.4786 0.088 Uiso 1 1 calc R . . N9' N 0.5235(10) 0.1769(6) 0.4176(6) 0.118(4) Uani 1 1 d . . . N12' N 0.3527(8) 0.2445(4) 0.0464(5) 0.079(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 Co1 0.0304(4) 0.0228(4) 0.0392(4) -0.0007(3) 0.0099(3) 0.0011(2) Co1' 0.0296(4) 0.0247(4) 0.0426(4) 0.0024(3) 0.0085(3) 0.0002(3) N2 0.032(2) 0.026(2) 0.049(3) -0.006(2) 0.0110(19) 0.0010(17) N3 0.042(2) 0.028(2) 0.029(2) -0.0002(18) 0.0100(18) 0.0018(18) N2' 0.033(2) 0.031(2) 0.043(3) -0.002(2) 0.0076(18) 0.0014(18) N4 0.038(2) 0.019(2) 0.062(3) 0.003(2) 0.018(2) 0.0000(17) N1 0.043(2) 0.041(3) 0.034(2) 0.005(2) 0.0122(19) 0.011(2) N1' 0.040(2) 0.038(3) 0.039(2) -0.001(2) 0.0095(19) 0.001(2) N5 0.040(2) 0.034(3) 0.043(3) 0.002(2) 0.0125(19) -0.0038(19) N4' 0.034(2) 0.030(3) 0.087(4) -0.002(3) 0.016(3) -0.0008(19) N3' 0.036(2) 0.032(2) 0.038(2) -0.0043(19) 0.0107(18) 0.0027(18) N7 0.040(3) 0.044(3) 0.049(3) -0.007(2) 0.013(2) 0.002(2) N5' 0.040(3) 0.038(3) 0.060(3) 0.007(3) 0.012(2) -0.001(2) N7' 0.036(3) 0.041(3) 0.072(4) -0.004(3) 0.015(3) 0.003(2) N10 0.039(3) 0.054(4) 0.056(3) 0.018(3) 0.012(2) 0.015(2) N10' 0.043(3) 0.057(4) 0.068(4) 0.019(3) 0.011(3) 0.002(3) N8 0.057(3) 0.034(3) 0.041(3) 0.001(2) 0.016(2) -0.005(2) C8' 0.041(3) 0.030(3) 0.045(3) 0.004(2) 0.009(2) 0.000(2) N11' 0.053(3) 0.031(3) 0.047(3) 0.004(2) 0.014(2) 0.007(2) C7' 0.039(3) 0.042(3) 0.045(3) 0.004(3) 0.013(2) -0.003(2) C5 0.053(3) 0.029(3) 0.050(3) -0.002(3) 0.009(3) 0.011(2) N11 0.045(3) 0.043(3) 0.053(3) 0.007(3) -0.001(2) 0.000(2) C8 0.050(3) 0.031(3) 0.052(3) -0.001(3) 0.020(3) 0.003(2) C12' 0.033(3) 0.039(3) 0.048(3) 0.001(3) 0.007(2) 0.003(2) C6 0.039(3) 0.029(3) 0.066(4) 0.001(3) 0.003(3) -0.003(2) C12 0.038(3) 0.047(4) 0.046(3) 0.007(3) 0.015(2) 0.004(2) C7 0.048(3) 0.035(3) 0.060(4) -0.001(3) 0.024(3) -0.006(2) C6' 0.044(3) 0.045(4) 0.047(3) -0.010(3) 0.009(2) -0.009(3) C1' 0.043(3) 0.045(4) 0.051(4) 0.011(3) 0.016(3) 0.008(3) C1 0.059(4) 0.042(3) 0.051(4) 0.008(3) 0.027(3) 0.011(3) C9 0.068(4) 0.030(3) 0.048(3) 0.008(3) 0.016(3) 0.006(3) C4' 0.076(5) 0.044(4) 0.063(4) -0.017(3) 0.024(4) -0.002(3) C5' 0.052(3) 0.036(3) 0.045(3) 0.002(3) 0.009(3) -0.003(3) N6 0.086(4) 0.024(3) 0.091(5) 0.006(3) 0.026(4) -0.009(3) C11 0.048(3) 0.058(4) 0.057(4) 0.015(3) 0.009(3) 0.017(3) C9' 0.067(4) 0.038(3) 0.048(4) 0.013(3) 0.005(3) -0.009(3) N8' 0.053(3) 0.052(4) 0.060(4) -0.018(3) 0.002(3) 0.014(3) N12 0.083(5) 0.102(6) 0.049(4) 0.037(4) 0.012(3) 0.003(4) N6' 0.090(5) 0.031(3) 0.130(7) -0.011(4) 0.042(5) -0.017(3) C2' 0.053(4) 0.070(5) 0.051(4) 0.001(3) 0.018(3) 0.012(3) C10 0.071(4) 0.050(4) 0.052(4) 0.015(3) 0.010(3) 0.016(3) C4 0.081(5) 0.043(4) 0.053(4) -0.017(3) 0.012(4) 0.004(3) C2 0.093(6) 0.065(5) 0.052(4) 0.017(4) 0.040(4) 0.033(4) C10' 0.067(4) 0.039(4) 0.057(4) 0.017(3) -0.001(3) -0.001(3) N9 0.089(5) 0.079(5) 0.047(3) -0.008(3) 0.010(3) -0.028(4) C3' 0.080(5) 0.046(4) 0.072(5) -0.004(4) 0.026(4) 0.011(4) C11' 0.044(3) 0.053(4) 0.057(4) 0.005(3) 0.000(3) 0.001(3) C3 0.111(7) 0.052(5) 0.057(4) -0.010(4) 0.027(5) 0.018(5) N9' 0.135(8) 0.108(8) 0.077(6) -0.048(6) -0.013(5) 0.043(6) N12' 0.111(6) 0.052(4) 0.073(5) 0.018(4) 0.030(4) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N4 1.936(4) . ? Co1 N7 1.945(5) . ? Co1 N3 1.950(5) . ? Co1 N1 1.958(5) . ? Co1 N2 1.958(5) . ? Co1 N10 1.966(5) . ? Co1' N7' 1.928(6) . ? Co1' N3' 1.933(5) . ? Co1' N4' 1.934(5) . ? Co1' N1' 1.943(5) . ? Co1' N10' 1.945(6) . ? Co1' N2' 1.962(5) . ? N2 C7 1.479(8) . ? N2 C6 1.483(8) . ? N3 C12 1.338(7) . ? N3 C8 1.348(8) . ? N2' C7' 1.484(8) . ? N2' C6' 1.488(8) . ? N4 N5 1.198(7) . ? N1 C5 1.315(9) . ? N1 C1 1.358(8) . ? N1' C5' 1.350(8) . ? N1' C1' 1.356(8) . ? N5 N6 1.137(8) . ? N4' N5' 1.177(8) . ? N3' C8' 1.338(8) . ? N3' C12' 1.347(7) . ? N7 N8 1.204(7) . ? N5' N6' 1.137(9) . ? N7' N8' 1.223(9) . ? N10 N11 1.196(8) . ? N10' N11' 1.184(8) . ? N8 N9 1.139(8) . ? C8' C9' 1.377(9) . ? C8' C7' 1.500(8) . ? N11' N12' 1.153(8) . ? C5 C4 1.388(9) . ? C5 C6 1.505(9) . ? N11 N12 1.139(9) . ? C8 C9 1.376(9) . ? C8 C7 1.471(9) . ? C12' C11' 1.373(9) . ? C12 C11 1.367(9) . ? C6' C5' 1.503(9) . ? C1' C2' 1.380(10) . ? C1 C2 1.358(10) . ? C9 C10 1.387(10) . ? C4' C3' 1.369(11) . ? C4' C5' 1.374(10) . ? C11 C10 1.391(11) . ? C9' C10' 1.349(10) . ? N8' N9' 1.111(11) . ? C2' C3' 1.354(12) . ? C4 C3 1.384(12) . ? C2 C3 1.374(13) . ? C10' C11' 1.376(10) . ? 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 N4 Co1 N7 92.4(2) . . ? N4 Co1 N3 92.3(2) . . ? N7 Co1 N3 92.5(2) . . ? N4 Co1 N1 93.7(2) . . ? N7 Co1 N1 173.9(2) . . ? N3 Co1 N1 87.57(19) . . ? N4 Co1 N2 175.79(19) . . ? N7 Co1 N2 89.8(2) . . ? N3 Co1 N2 83.98(19) . . ? N1 Co1 N2 84.2(2) . . ? N4 Co1 N10 93.3(2) . . ? N7 Co1 N10 89.3(2) . . ? N3 Co1 N10 174.1(2) . . ? N1 Co1 N10 90.0(2) . . ? N2 Co1 N10 90.4(2) . . ? N7' Co1' N3' 91.8(2) . . ? N7' Co1' N4' 92.3(2) . . ? N3' Co1' N4' 93.2(2) . . ? N7' Co1' N1' 174.9(2) . . ? N3' Co1' N1' 87.1(2) . . ? N4' Co1' N1' 92.7(2) . . ? N7' Co1' N10' 89.5(3) . . ? N3' Co1' N10' 171.5(2) . . ? N4' Co1' N10' 95.1(2) . . ? N1' Co1' N10' 90.9(3) . . ? N7' Co1' N2' 89.8(2) . . ? N3' Co1' N2' 84.6(2) . . ? N4' Co1' N2' 177.0(2) . . ? N1' Co1' N2' 85.2(2) . . ? N10' Co1' N2' 87.0(2) . . ? C7 N2 C6 115.2(5) . . ? C7 N2 Co1 109.6(3) . . ? C6 N2 Co1 109.4(4) . . ? C12 N3 C8 120.4(5) . . ? C12 N3 Co1 124.7(4) . . ? C8 N3 Co1 114.4(4) . . ? C7' N2' C6' 114.8(5) . . ? C7' N2' Co1' 110.1(3) . . ? C6' N2' Co1' 108.4(4) . . ? N5 N4 Co1 119.7(4) . . ? C5 N1 C1 119.9(6) . . ? C5 N1 Co1 114.8(4) . . ? C1 N1 Co1 125.2(5) . . ? C5' N1' C1' 118.6(6) . . ? C5' N1' Co1' 114.7(4) . . ? C1' N1' Co1' 126.2(4) . . ? N6 N5 N4 175.4(6) . . ? N5' N4' Co1' 123.3(5) . . ? C8' N3' C12' 119.6(5) . . ? C8' N3' Co1' 114.6(4) . . ? C12' N3' Co1' 125.8(4) . . ? N8 N7 Co1 118.3(4) . . ? N6' N5' N4' 174.4(8) . . ? N8' N7' Co1' 119.8(4) . . ? N11 N10 Co1 114.2(4) . . ? N11' N10' Co1' 122.5(5) . . ? N9 N8 N7 178.2(7) . . ? N3' C8' C9' 120.6(6) . . ? N3' C8' C7' 116.3(5) . . ? C9' C8' C7' 123.1(6) . . ? N12' N11' N10' 174.7(8) . . ? N2' C7' C8' 109.3(5) . . ? N1 C5 C4 122.1(7) . . ? N1 C5 C6 115.7(6) . . ? C4 C5 C6 122.2(7) . . ? N12 N11 N10 176.6(8) . . ? N3 C8 C9 120.7(6) . . ? N3 C8 C7 114.9(6) . . ? C9 C8 C7 124.3(6) . . ? N3' C12' C11' 121.2(6) . . ? N2 C6 C5 109.9(5) . . ? N3 C12 C11 121.4(6) . . ? C8 C7 N2 109.9(5) . . ? N2' C6' C5' 110.6(5) . . ? N1' C1' C2' 121.7(6) . . ? N1 C1 C2 120.9(7) . . ? C8 C9 C10 119.4(6) . . ? C3' C4' C5' 119.7(8) . . ? N1' C5' C4' 121.0(6) . . ? N1' C5' C6' 114.0(6) . . ? C4' C5' C6' 125.0(6) . . ? C12 C11 C10 119.3(6) . . ? C10' C9' C8' 120.0(6) . . ? N9' N8' N7' 179.2(11) . . ? C3' C2' C1' 119.0(7) . . ? C9 C10 C11 118.8(6) . . ? C3 C4 C5 117.8(8) . . ? C1 C2 C3 119.6(7) . . ? C9' C10' C11' 119.7(6) . . ? C2' C3' C4' 120.0(8) . . ? C12' C11' C10' 118.7(6) . . ? C2 C3 C4 119.6(7) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.018 _refine_diff_density_min -0.831 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 958300' ####################################################################### # # 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_as_march2_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Co N12' _chemical_formula_weight 398.30 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' 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4440(7) _cell_length_b 12.3232(10) _cell_length_c 8.7986(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.066(6) _cell_angle_gamma 90.00 _cell_volume 835.97(12) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12268 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.22 _reflns_number_total 3652 _reflns_number_gt 2344 _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^)+(0.0864P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 3652 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 Co1 Co 0.16170(9) 0.24450(8) 0.19136(9) 0.0428(2) Uani 1 1 d . . . N8 N 0.1853(7) 0.4662(5) 0.2413(7) 0.0513(14) Uani 1 1 d . . . N9 N 0.2453(11) 0.5463(6) 0.2221(10) 0.082(2) Uani 1 1 d . . . N11 N 0.4700(7) 0.3198(6) 0.4310(8) 0.0578(16) Uani 1 1 d . . . N4 N 0.1946(8) 0.0975(5) 0.1188(8) 0.0572(15) Uani 1 1 d . . . N7 N 0.1156(8) 0.3875(5) 0.2652(7) 0.0545(15) Uani 1 1 d . . . C11 C 0.1282(15) 0.0877(9) 0.6676(12) 0.074(3) Uani 1 1 d . . . H11 H 0.1242 0.0587 0.7636 0.089 Uiso 1 1 calc R . . C8 C -0.1616(8) 0.2379(11) 0.2874(8) 0.0588(16) Uani 1 1 d . . . H8A H -0.1405 0.3154 0.2885 0.071 Uiso 1 1 calc R . . H8B H -0.2581 0.2273 0.3186 0.071 Uiso 1 1 calc R . . N2 N -0.0846(7) 0.2246(6) 0.0454(7) 0.0549(17) Uani 1 1 d D . . C6 C -0.1401(10) 0.3153(7) -0.0713(10) 0.062(2) Uani 1 1 d . . . H6A H -0.1647 0.3783 -0.0186 0.074 Uiso 1 1 calc R . . H6B H -0.2444 0.2962 -0.1677 0.074 Uiso 1 1 calc R . . C5 C 0.0067(9) 0.3397(5) -0.1235(8) 0.0486(16) Uani 1 1 d . . . N1 N 0.1639(7) 0.3079(4) -0.0083(6) 0.0433(12) Uani 1 1 d . . . N10 N 0.4109(7) 0.2675(5) 0.3074(8) 0.0546(18) Uani 1 1 d . . . N12 N 0.5330(10) 0.3660(8) 0.5533(9) 0.090(2) Uani 1 1 d . . . N5 N 0.3260(9) 0.0795(5) 0.1045(9) 0.0668(17) Uani 1 1 d . . . N3 N 0.1404(7) 0.1780(4) 0.3857(7) 0.0487(13) Uani 1 1 d . . . C13 C 0.2764(10) 0.1221(6) 0.4952(9) 0.0572(18) Uani 1 1 d . . . H13 H 0.3737 0.1131 0.4723 0.069 Uiso 1 1 calc R . . C12 C 0.2778(12) 0.0786(7) 0.6375(10) 0.068(2) Uani 1 1 d . . . H12 H 0.3758 0.0435 0.7130 0.081 Uiso 1 1 calc R . . C10 C -0.0108(11) 0.1398(6) 0.5539(9) 0.061(2) Uani 1 1 d . . . H10 H -0.1120 0.1448 0.5715 0.074 Uiso 1 1 calc R . . C9 C -0.0063(9) 0.1854(6) 0.4131(9) 0.0522(17) Uani 1 1 d . . . C7 C -0.2119(9) 0.1967(7) 0.1145(9) 0.0628(19) Uani 1 1 d . . . H7A H -0.2240 0.1184 0.1144 0.075 Uiso 1 1 calc R . . H7B H -0.3238 0.2268 0.0433 0.075 Uiso 1 1 calc R . . C4 C -0.0093(11) 0.3832(6) -0.2700(9) 0.061(2) Uani 1 1 d . . . H4 H -0.1179 0.4055 -0.3463 0.074 Uiso 1 1 calc R . . C1 C 0.3028(9) 0.3217(6) -0.0430(9) 0.0538(17) Uani 1 1 d . . . H1 H 0.4116 0.3022 0.0362 0.065 Uiso 1 1 calc R . . C2 C 0.2891(11) 0.3641(7) -0.1934(10) 0.064(2) Uani 1 1 d . . . H2 H 0.3873 0.3712 -0.2154 0.077 Uiso 1 1 calc R . . N6 N 0.4468(12) 0.0572(7) 0.0834(13) 0.112(3) Uani 1 1 d . . . C3 C 0.1322(13) 0.3953(8) -0.3084(9) 0.058(3) Uani 1 1 d . . . H3 H 0.1205 0.4240 -0.4102 0.070 Uiso 1 1 calc R . . H2N H -0.098(11) 0.178(5) -0.038(7) 0.070 Uiso 1 1 d 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 Co1 0.0342(4) 0.0444(4) 0.0543(4) 0.0013(5) 0.0227(3) 0.0024(5) N8 0.054(4) 0.043(3) 0.066(4) 0.003(3) 0.034(3) 0.009(3) N9 0.089(5) 0.057(5) 0.118(6) 0.009(4) 0.061(5) -0.002(4) N11 0.036(3) 0.084(5) 0.051(4) 0.006(4) 0.015(3) -0.002(3) N4 0.053(4) 0.044(3) 0.078(4) -0.004(3) 0.031(3) 0.011(3) N7 0.055(4) 0.049(4) 0.075(4) 0.002(3) 0.042(3) 0.000(3) C11 0.101(9) 0.060(6) 0.076(7) -0.001(5) 0.051(7) -0.029(6) C8 0.053(3) 0.059(4) 0.081(4) 0.003(5) 0.044(3) 0.006(4) N2 0.042(3) 0.069(5) 0.057(3) -0.002(3) 0.023(3) -0.005(3) C6 0.047(4) 0.065(5) 0.071(5) 0.008(4) 0.022(4) 0.019(4) C5 0.050(4) 0.043(4) 0.054(4) -0.003(3) 0.022(3) -0.001(3) N1 0.040(3) 0.038(3) 0.052(3) -0.005(2) 0.020(3) 0.001(2) N10 0.033(3) 0.068(6) 0.063(4) 0.000(3) 0.021(3) 0.002(3) N12 0.068(5) 0.118(7) 0.065(5) -0.004(5) 0.008(4) -0.019(5) N5 0.067(4) 0.046(3) 0.101(5) 0.005(3) 0.049(4) 0.015(3) N3 0.045(3) 0.044(3) 0.063(4) 0.000(3) 0.027(3) -0.001(3) C13 0.049(4) 0.056(4) 0.066(5) 0.004(3) 0.022(4) 0.000(3) C12 0.086(6) 0.052(4) 0.064(5) 0.016(4) 0.029(5) -0.003(4) C10 0.068(5) 0.055(4) 0.076(5) -0.002(4) 0.045(5) -0.011(4) C9 0.054(4) 0.047(4) 0.072(5) -0.007(3) 0.042(4) -0.012(3) C7 0.041(4) 0.066(4) 0.089(5) 0.009(4) 0.035(4) -0.002(3) C4 0.069(5) 0.052(4) 0.060(5) 0.001(3) 0.022(4) 0.006(4) C1 0.044(4) 0.060(4) 0.062(4) -0.001(3) 0.026(3) 0.000(3) C2 0.074(6) 0.056(5) 0.075(5) 0.003(4) 0.044(5) -0.012(4) N6 0.094(6) 0.095(7) 0.187(9) 0.018(6) 0.097(7) 0.042(5) C3 0.089(7) 0.047(5) 0.041(4) 0.002(3) 0.029(5) -0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 1.929(5) . ? Co1 N10 1.949(6) . ? Co1 N2 1.964(6) . ? Co1 N3 1.969(5) . ? Co1 N7 1.971(6) . ? Co1 N4 1.978(6) . ? N8 N9 1.153(8) . ? N8 N7 1.197(8) . ? N11 N12 1.140(9) . ? N11 N10 1.184(8) . ? N4 N5 1.187(8) . ? C11 C10 1.354(13) . ? C11 C12 1.397(13) . ? C11 H11 0.9300 . ? C8 C9 1.476(10) . ? C8 C7 1.491(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? N2 C6 1.460(10) . ? N2 C7 1.475(8) . ? N2 H2N 0.91(2) . ? C6 C5 1.518(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C4 1.351(9) . ? C5 N1 1.359(8) . ? N1 C1 1.338(8) . ? N5 N6 1.142(9) . ? N3 C13 1.348(9) . ? N3 C9 1.359(8) . ? C13 C12 1.358(10) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C10 C9 1.375(9) . ? C10 H10 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4 C3 1.376(11) . ? C4 H4 0.9300 . ? C1 C2 1.383(10) . ? C1 H1 0.9300 . ? C2 C3 1.354(12) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? 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 N1 Co1 N10 90.5(2) . . ? N1 Co1 N2 81.7(2) . . ? N10 Co1 N2 171.9(2) . . ? N1 Co1 N3 175.7(2) . . ? N10 Co1 N3 93.8(2) . . ? N2 Co1 N3 93.9(2) . . ? N1 Co1 N7 90.9(2) . . ? N10 Co1 N7 90.8(3) . . ? N2 Co1 N7 91.6(3) . . ? N3 Co1 N7 89.2(2) . . ? N1 Co1 N4 91.2(2) . . ? N10 Co1 N4 92.2(3) . . ? N2 Co1 N4 85.7(3) . . ? N3 Co1 N4 88.5(2) . . ? N7 Co1 N4 176.3(3) . . ? N9 N8 N7 175.3(7) . . ? N12 N11 N10 176.6(8) . . ? N5 N4 Co1 117.7(5) . . ? N8 N7 Co1 119.3(4) . . ? C10 C11 C12 118.5(8) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C9 C8 C7 114.3(8) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C6 N2 C7 112.9(6) . . ? C6 N2 Co1 108.4(5) . . ? C7 N2 Co1 121.0(4) . . ? C6 N2 H2N 91(5) . . ? C7 N2 H2N 108(5) . . ? Co1 N2 H2N 111(5) . . ? N2 C6 C5 107.3(5) . . ? N2 C6 H6A 110.3 . . ? C5 C6 H6A 110.3 . . ? N2 C6 H6B 110.3 . . ? C5 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? C4 C5 N1 120.9(7) . . ? C4 C5 C6 126.2(7) . . ? N1 C5 C6 112.8(6) . . ? C1 N1 C5 118.3(6) . . ? C1 N1 Co1 126.5(5) . . ? C5 N1 Co1 115.3(4) . . ? N11 N10 Co1 121.4(5) . . ? N6 N5 N4 175.6(9) . . ? C13 N3 C9 118.7(6) . . ? C13 N3 Co1 118.7(5) . . ? C9 N3 Co1 122.6(5) . . ? N3 C13 C12 123.1(7) . . ? N3 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C13 C12 C11 118.3(8) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C11 C10 C9 121.7(8) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? N3 C9 C10 119.7(7) . . ? N3 C9 C8 119.5(6) . . ? C10 C9 C8 120.8(6) . . ? N2 C7 C8 112.9(6) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C5 C4 C3 121.2(8) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? N1 C1 C2 121.8(7) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.8(7) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 118.0(7) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.337 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 958301'