# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bu, Xian-He' _publ_contact_author_email buxh@nankai.edu.cn _publ_author_name 'Xian-He Bu' data_3 _database_code_depnum_ccdc_archive 'CCDC 791132' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Co N10 O' _chemical_formula_weight 371.25 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' Co Co 0.3494 0.9721 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.5226(7) _cell_length_b 9.6595(19) _cell_length_c 11.578(2) _cell_angle_alpha 100.01(3) _cell_angle_beta 94.90(3) _cell_angle_gamma 92.32(3) _cell_volume 385.93(13) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3366 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description Prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 189 _exptl_absorpt_coefficient_mu 1.136 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.893 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3201 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1322 _reflns_number_gt 1098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.9326P] 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 1322 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2067 _refine_ls_wR_factor_gt 0.1962 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 1.0000 0.5000 0.5000 0.0336(5) Uani 1 2 d S . . N4 N 0.9520(15) 0.2994(5) 0.3934(4) 0.0284(12) Uani 1 1 d . . . N5 N 0.9389(14) 0.1321(5) 0.2355(4) 0.0249(11) Uani 1 1 d . . . C1 C 1.0103(19) 0.2711(7) 0.2807(5) 0.0304(15) Uani 1 1 d . . . H1 H 1.0901 0.3380 0.2377 0.037 Uiso 1 1 calc R . . N1 N 0.4775(17) 0.5606(6) 0.3997(5) 0.0352(14) Uani 1 1 d . . . N2 N 0.5019(19) 0.6413(6) 0.3332(5) 0.0422(15) Uani 1 1 d . . . C2 C 0.8376(19) 0.1718(7) 0.4218(6) 0.0336(16) Uani 1 1 d . . . H2 H 0.7760 0.1589 0.4958 0.040 Uiso 1 1 calc R . . C4 C 0.9685(16) 0.0650(6) 0.1153(5) 0.0226(13) Uani 1 1 d . . . C3 C 0.828(2) 0.0675(7) 0.3254(6) 0.0334(15) Uani 1 1 d . . . H3 H 0.7612 -0.0275 0.3212 0.040 Uiso 1 1 calc R . . C6 C 0.9063(18) 0.1392(6) 0.0237(5) 0.0263(14) Uani 1 1 d . . . H6 H 0.8454 0.2329 0.0401 0.032 Uiso 1 1 calc R . . C5 C 1.0661(18) -0.0749(7) 0.0929(5) 0.0276(14) Uani 1 1 d . . . H5 H 1.1120 -0.1244 0.1542 0.033 Uiso 1 1 calc R . . N3 N 0.525(3) 0.7216(9) 0.2706(8) 0.078(3) Uani 1 1 d . . . O1W O 0.747(10) 0.508(4) 0.062(3) 0.233(16) Uiso 0.50 1 d P . . 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 0.0668(11) 0.0159(7) 0.0169(7) -0.0014(5) 0.0054(6) 0.0033(6) N4 0.033(3) 0.029(3) 0.023(3) 0.001(2) 0.007(2) -0.002(2) N5 0.021(3) 0.027(3) 0.023(3) -0.003(2) 0.002(2) 0.000(2) C1 0.039(4) 0.028(3) 0.023(3) 0.000(3) 0.003(3) 0.005(3) N1 0.056(4) 0.027(3) 0.024(3) 0.007(2) 0.005(3) 0.002(3) N2 0.055(4) 0.038(3) 0.033(3) 0.005(3) 0.003(3) 0.002(3) C2 0.041(4) 0.032(4) 0.027(3) 0.004(3) 0.003(3) -0.001(3) C4 0.016(3) 0.026(3) 0.023(3) -0.004(2) 0.005(2) -0.001(2) C3 0.045(4) 0.025(3) 0.029(3) 0.002(3) 0.007(3) -0.003(3) C6 0.027(3) 0.023(3) 0.028(3) 0.001(2) 0.008(3) 0.007(2) C5 0.028(4) 0.029(3) 0.025(3) 0.003(3) 0.002(3) 0.002(3) N3 0.097(7) 0.069(5) 0.084(6) 0.058(5) 0.011(5) 0.008(5) _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 2.101(5) 2_766 ? Co1 N4 2.101(5) . ? Co1 N1 2.239(6) 2_666 ? Co1 N1 2.239(6) 1_655 ? Co1 N1 2.244(6) 2_766 ? Co1 N1 2.244(6) . ? N4 C1 1.321(8) . ? N4 C2 1.383(8) . ? N5 C1 1.358(8) . ? N5 C3 1.378(8) . ? N5 C4 1.445(7) . ? C1 H1 0.9300 . ? N1 N2 1.193(8) . ? N1 Co1 2.239(6) 1_455 ? N2 N3 1.154(9) . ? C2 C3 1.364(9) . ? C2 H2 0.9300 . ? C4 C6 1.387(9) . ? C4 C5 1.394(8) . ? C3 H3 0.9300 . ? C6 C5 1.397(8) 2_755 ? C6 H6 0.9300 . ? C5 C6 1.397(8) 2_755 ? C5 H5 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 N4 Co1 N4 180.000(1) 2_766 . ? N4 Co1 N1 89.4(2) 2_766 2_666 ? N4 Co1 N1 90.6(2) . 2_666 ? N4 Co1 N1 90.6(2) 2_766 1_655 ? N4 Co1 N1 89.4(2) . 1_655 ? N1 Co1 N1 180.000(1) 2_666 1_655 ? N4 Co1 N1 90.1(2) 2_766 2_766 ? N4 Co1 N1 89.9(2) . 2_766 ? N1 Co1 N1 103.6(2) 2_666 2_766 ? N1 Co1 N1 76.4(2) 1_655 2_766 ? N4 Co1 N1 89.9(2) 2_766 . ? N4 Co1 N1 90.1(2) . . ? N1 Co1 N1 76.4(2) 2_666 . ? N1 Co1 N1 103.6(2) 1_655 . ? N1 Co1 N1 180.000(1) 2_766 . ? C1 N4 C2 105.3(5) . . ? C1 N4 Co1 125.8(4) . . ? C2 N4 Co1 128.8(4) . . ? C1 N5 C3 107.3(5) . . ? C1 N5 C4 126.3(5) . . ? C3 N5 C4 126.4(5) . . ? N4 C1 N5 111.5(6) . . ? N4 C1 H1 124.3 . . ? N5 C1 H1 124.3 . . ? N2 N1 Co1 132.2(5) . 1_455 ? N2 N1 Co1 120.8(5) . . ? Co1 N1 Co1 103.6(2) 1_455 . ? N3 N2 N1 178.7(8) . . ? C3 C2 N4 110.2(6) . . ? C3 C2 H2 124.9 . . ? N4 C2 H2 124.9 . . ? C6 C4 C5 120.5(6) . . ? C6 C4 N5 120.5(5) . . ? C5 C4 N5 119.0(5) . . ? C2 C3 N5 105.7(6) . . ? C2 C3 H3 127.2 . . ? N5 C3 H3 127.2 . . ? C4 C6 C5 120.8(6) . 2_755 ? C4 C6 H6 119.6 . . ? C5 C6 H6 119.6 2_755 . ? C4 C5 C6 118.6(6) . 2_755 ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 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 N4 Co1 N4 C1 29(100) 2_766 . . . ? N1 Co1 N4 C1 145.8(5) 2_666 . . . ? N1 Co1 N4 C1 -34.2(5) 1_655 . . . ? N1 Co1 N4 C1 -110.6(5) 2_766 . . . ? N1 Co1 N4 C1 69.4(5) . . . . ? N4 Co1 N4 C2 -148(100) 2_766 . . . ? N1 Co1 N4 C2 -30.7(6) 2_666 . . . ? N1 Co1 N4 C2 149.3(6) 1_655 . . . ? N1 Co1 N4 C2 72.9(6) 2_766 . . . ? N1 Co1 N4 C2 -107.1(6) . . . . ? C2 N4 C1 N5 0.0(7) . . . . ? Co1 N4 C1 N5 -177.1(4) . . . . ? C3 N5 C1 N4 -0.1(8) . . . . ? C4 N5 C1 N4 179.1(5) . . . . ? N4 Co1 N1 N2 72.2(5) 2_766 . . . ? N4 Co1 N1 N2 -107.8(5) . . . . ? N1 Co1 N1 N2 161.7(6) 2_666 . . . ? N1 Co1 N1 N2 -18.3(6) 1_655 . . . ? N1 Co1 N1 N2 -46(100) 2_766 . . . ? N4 Co1 N1 Co1 -89.4(2) 2_766 . . 1_455 ? N4 Co1 N1 Co1 90.6(2) . . . 1_455 ? N1 Co1 N1 Co1 0.0 2_666 . . 1_455 ? N1 Co1 N1 Co1 180.0 1_655 . . 1_455 ? N1 Co1 N1 Co1 152(100) 2_766 . . 1_455 ? Co1 N1 N2 N3 68(37) 1_455 . . . ? Co1 N1 N2 N3 -87(37) . . . . ? C1 N4 C2 C3 0.0(7) . . . . ? Co1 N4 C2 C3 177.0(5) . . . . ? C1 N5 C4 C6 -29.4(9) . . . . ? C3 N5 C4 C6 149.7(6) . . . . ? C1 N5 C4 C5 149.7(6) . . . . ? C3 N5 C4 C5 -31.3(9) . . . . ? N4 C2 C3 N5 -0.1(8) . . . . ? C1 N5 C3 C2 0.1(7) . . . . ? C4 N5 C3 C2 -179.1(5) . . . . ? C5 C4 C6 C5 1.1(10) . . . 2_755 ? N5 C4 C6 C5 -179.9(5) . . . 2_755 ? C6 C4 C5 C6 -1.0(10) . . . 2_755 ? N5 C4 C5 C6 179.9(5) . . . 2_755 ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 1.271 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.128