Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'ProfD Ivan Bernal' _publ_contact_author_address ; Department of Chemistry University of Houston Houston Texas 77204 UNITED STATES OF AMERICA ; _publ_contact_author_email IBERNAL@UH.EDU _publ_section_title ; Cleavage of the Peptide Bond of beta-alanyl-L-histidine (Carnosine) Induced by Co(III)-amine Complex : Reaction, Structure and Mechanism ; loop_ _publ_author_name 'Ivan Bernal' 'Uday Mukhopadhyay' 'Manas K. Saha' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 208929' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C12 H26 Cl2 Co N7 O10' _chemical_formula_weight 558.23 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.462(2) _cell_length_b 11.035(5) _cell_length_c 18.321(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2115.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.131 _exptl_absorpt_correction_type Difabs _exptl_absorpt_process_details ; emperical [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.4704 _exptl_absorpt_correction_T_max 0.5693 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.092312 _diffrn_orient_matrix_ub_12 0.014096 _diffrn_orient_matrix_ub_13 0.000534 _diffrn_orient_matrix_ub_21 0.02171 _diffrn_orient_matrix_ub_22 0.046926 _diffrn_orient_matrix_ub_23 -0.041429 _diffrn_orient_matrix_ub_31 -0.011965 _diffrn_orient_matrix_ub_32 -0.024054 _diffrn_orient_matrix_ub_33 -0.080598 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_standards_decay_corr_max 1 _diffrn_standards_decay_corr_min 1 _diffrn_reflns_av_R_equivalents 0.05 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_number 3373 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.98 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.745 _diffrn_measured_fraction_theta_max 0.745 _reflns_number_total 3095 _reflns_number_gt 2653 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0841P)^2^+1.0027P] 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_number_reflns 3095 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.055 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 4.577 _refine_ls_shift/su_mean 0.178 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_diff_density_max 0.514 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.062 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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 0.0788(6) -0.0627(7) 0.9315(4) 0.058(2) Uani 1 1 d . . . H5 H 0.0901 -0.0876 0.9819 0.069 Uiso 1 1 calc R . . H6 H 0.0632 -0.1344 0.9022 0.069 Uiso 1 1 calc R . . C2 C -0.0343(6) 0.0249(6) 0.9253(4) 0.0554(19) Uani 1 1 d . . . H3 H -0.1144 -0.0185 0.9306 0.066 Uiso 1 1 calc R . . H4 H -0.0295 0.0864 0.9631 0.066 Uiso 1 1 calc R . . C3 C 0.2418(6) 0.0965(6) 0.9575(4) 0.0509(18) Uani 1 1 d . . . H7 H 0.3345 0.0983 0.9582 0.061 Uiso 1 1 calc R . . H8 H 0.2122 0.0768 1.0063 0.061 Uiso 1 1 calc R . . C4 C 0.1906(6) 0.2204(5) 0.9350(5) 0.051(2) Uani 1 1 d . . . H9 H 0.1027 0.2293 0.951 0.061 Uiso 1 1 calc R . . H10 H 0.2411 0.284 0.9575 0.061 Uiso 1 1 calc R . . C5 C 0.3016(6) -0.0856(6) 0.8873(4) 0.0538(17) Uani 1 1 d . . . H13 H 0.2669 -0.1563 0.8628 0.065 Uiso 1 1 calc R . . H14 H 0.3432 -0.112 0.9318 0.065 Uiso 1 1 calc R . . C6 C 0.3968(6) -0.0229(6) 0.8383(4) 0.056(2) Uani 1 1 d . . . H15 H 0.4482 0.0334 0.8665 0.067 Uiso 1 1 calc R . . H16 H 0.4532 -0.082 0.816 0.067 Uiso 1 1 calc R . . C7 C 0.0746(4) -0.0758(5) 0.7042(5) 0.0390(17) Uani 1 1 d . . . C8 C 0.0870(5) 0.0463(4) 0.6643(3) 0.0397(17) Uani 1 1 d . . . H21 H 0.1702 0.0457 0.6397 0.048 Uiso 1 1 calc R . . C9 C -0.0141(5) 0.0640(6) 0.6049(4) 0.0460(15) Uani 1 1 d . . . H22 H 0.001 0.1404 0.5801 0.055 Uiso 1 1 calc R . . H23 H -0.0067 -0.0004 0.5691 0.055 Uiso 1 1 calc R . . C10 C -0.1474(5) 0.0637(4) 0.6365(4) 0.0420(17) Uani 1 1 d . . . C11 C -0.2589(6) 0.0894(7) 0.6022(5) 0.0616(19) Uani 1 1 d . . . H24 H -0.2696 0.1128 0.5538 0.074 Uiso 1 1 calc R . . C12 C -0.2954(6) 0.0438(6) 0.7153(5) 0.062(2) Uani 1 1 d . . . H26 H -0.339 0.0293 0.7586 0.074 Uiso 1 1 calc R . . N1 N 0.1968(4) 0.0017(4) 0.9047(3) 0.0436(13) Uani 1 1 d . . . N2 N -0.0264(4) 0.0824(4) 0.8512(3) 0.0411(12) Uani 1 1 d . . . H1 H -0.0518 0.1601 0.8541 0.049 Uiso 1 1 calc R . . H2 H -0.0795 0.0435 0.8204 0.049 Uiso 1 1 calc R . . N3 N 0.1979(4) 0.2297(4) 0.8559(3) 0.0383(14) Uani 1 1 d . . . H11 H 0.2782 0.2487 0.8424 0.046 Uiso 1 1 calc R . . H12 H 0.1453 0.2887 0.8401 0.046 Uiso 1 1 calc R . . N4 N 0.3245(4) 0.0436(4) 0.7808(3) 0.0403(12) Uani 1 1 d . . . H17 H 0.3231 -0.0007 0.7396 0.048 Uiso 1 1 calc R . . H18 H 0.364 0.1142 0.771 0.048 Uiso 1 1 calc R . . N5 N 0.0924(4) 0.1429(3) 0.7196(3) 0.0348(12) Uani 1 1 d . . . H19 H 0.0146 0.1766 0.7248 0.042 Uiso 1 1 calc R . . H20 H 0.1471 0.2011 0.705 0.042 Uiso 1 1 calc R . . N6 N -0.1717(5) 0.0369(5) 0.7086(4) 0.0577(16) Uani 1 1 d . . . N7 N -0.3518(5) 0.0739(6) 0.6531(4) 0.0628(16) Uani 1 1 d . . . H25 H -0.4327 0.0822 0.6462 0.075 Uiso 1 1 calc R . . O1 O 0.1035(3) -0.0769(3) 0.7716(3) 0.0407(11) Uani 1 1 d . . . O2 O 0.0420(4) -0.1654(3) 0.6688(3) 0.0565(14) Uani 1 1 d . . . O3 O -0.5171(6) 0.2836(7) 0.9207(4) 0.100(2) Uani 1 1 d . . . O4 O -0.3737(5) 0.4072(4) 0.8591(4) 0.0835(17) Uani 1 1 d . . . O5 O -0.4954(6) 0.2625(6) 0.7981(4) 0.0920(19) Uani 1 1 d . . . O6 O -0.3304(6) 0.2036(6) 0.8777(4) 0.107(2) Uani 1 1 d . . . O7 O -0.7177(10) 0.3267(9) 0.6650(5) 0.165(5) Uani 1 1 d . . . O8 O -0.6054(9) 0.3668(11) 0.5638(4) 0.194(6) Uani 1 1 d . . . O9 O -0.6021(11) 0.1867(9) 0.6187(7) 0.214(6) Uani 1 1 d . . . O10 O -0.7756(5) 0.2393(5) 0.5568(3) 0.0692(14) Uani 1 1 d . . . Cl1 Cl -0.42758(13) 0.28865(13) 0.86307(11) 0.0529(5) Uani 1 1 d . . . Cl2 Cl -0.67157(12) 0.28221(12) 0.59905(10) 0.0466(4) Uani 1 1 d . . . Co Co 0.14870(6) 0.07583(5) 0.81259(4) 0.0330(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 0.061(4) 0.072(4) 0.041(6) 0.028(4) 0.003(3) -0.003(3) C2 0.053(3) 0.070(4) 0.043(6) 0.008(3) 0.015(3) -0.015(3) C3 0.053(3) 0.073(4) 0.026(6) 0.000(3) -0.004(3) 0.000(3) C4 0.052(3) 0.062(3) 0.039(7) -0.006(3) -0.004(3) -0.006(3) C5 0.056(3) 0.051(3) 0.055(6) 0.014(3) -0.010(3) 0.008(3) C6 0.042(3) 0.066(3) 0.059(6) 0.001(3) -0.006(3) 0.015(3) C7 0.029(2) 0.039(2) 0.049(6) -0.007(3) 0.001(3) -0.002(2) C8 0.035(2) 0.048(3) 0.036(6) -0.002(2) 0.005(2) -0.0041(19) C9 0.043(3) 0.060(3) 0.035(5) -0.003(3) 0.000(3) -0.001(2) C10 0.038(2) 0.044(2) 0.044(6) 0.001(3) -0.005(3) -0.001(2) C11 0.052(3) 0.087(4) 0.046(6) 0.011(4) -0.012(4) -0.003(3) C12 0.039(3) 0.085(4) 0.061(7) 0.007(4) 0.002(3) 0.005(3) N1 0.049(2) 0.052(2) 0.030(4) 0.016(2) -0.001(2) -0.0012(19) N2 0.0333(19) 0.0422(19) 0.048(4) -0.001(2) 0.003(2) -0.0047(18) N3 0.041(2) 0.043(2) 0.031(5) 0.000(2) -0.003(2) -0.0049(17) N4 0.038(2) 0.046(2) 0.038(4) -0.0041(19) 0.003(2) 0.0030(16) N5 0.037(2) 0.0346(19) 0.032(4) 0.0072(18) 0.001(2) -0.0039(16) N6 0.042(3) 0.094(4) 0.036(5) 0.014(3) 0.002(2) 0.000(2) N7 0.035(2) 0.092(3) 0.061(5) 0.009(3) -0.006(3) 0.005(3) O1 0.0476(18) 0.0325(15) 0.042(4) 0.0042(19) -0.004(2) -0.0017(15) O2 0.050(2) 0.0423(18) 0.077(4) -0.015(2) -0.007(2) -0.0030(16) O3 0.090(4) 0.136(5) 0.074(5) -0.002(4) 0.022(4) -0.034(4) O4 0.087(3) 0.080(3) 0.083(5) 0.013(3) -0.017(3) -0.040(3) O5 0.110(4) 0.100(4) 0.066(5) 0.003(3) -0.032(4) -0.027(3) O6 0.108(5) 0.098(4) 0.116(6) 0.003(4) -0.020(4) 0.022(4) O7 0.177(8) 0.228(10) 0.091(7) -0.077(7) 0.043(6) -0.110(8) O8 0.198(9) 0.322(14) 0.062(6) 0.065(6) -0.042(5) -0.203(10) O9 0.214(10) 0.161(8) 0.268(14) -0.054(8) -0.159(10) 0.110(7) O10 0.075(3) 0.084(3) 0.048(4) 0.004(3) -0.010(3) -0.029(2) Cl1 0.0489(7) 0.0602(8) 0.0495(15) 0.0020(8) -0.0042(8) -0.0133(6) Cl2 0.0460(7) 0.0574(7) 0.0362(14) -0.0014(7) -0.0025(7) -0.0042(6) Co 0.0324(3) 0.0328(3) 0.0338(6) 0.0054(3) 0.0002(3) -0.0008(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 1.506(7) . ? C1 C2 1.533(10) . ? C2 N2 1.501(9) . ? C3 N1 1.500(8) . ? C3 C4 1.525(9) . ? C4 N3 1.455(9) . ? C5 N1 1.494(7) . ? C5 C6 1.508(9) . ? C6 N4 1.490(8) . ? C7 O2 1.231(7) . ? C7 O1 1.271(7) . ? C7 C8 1.538(8) . ? C8 N5 1.471(7) . ? C8 C9 1.531(8) . ? C9 C10 1.510(8) . ? C10 C11 1.355(9) . ? C10 N6 1.377(9) . ? C11 N7 1.358(10) . ? C12 N6 1.302(8) . ? C12 N7 1.326(10) . ? N1 Co 1.942(5) . ? N2 Co 1.965(4) . ? N3 Co 1.944(4) . ? N4 Co 1.961(4) . ? N5 Co 1.950(5) . ? O1 Co 1.905(4) . ? O3 Cl1 1.412(6) . ? O4 Cl1 1.426(5) . ? O5 Cl1 1.415(6) . ? O6 Cl1 1.410(6) . ? O7 Cl2 1.391(8) . ? O8 Cl2 1.329(7) . ? O9 Cl2 1.329(7) . ? O10 Cl2 1.417(5) . ? 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 C1 C2 108.1(5) . . ? N2 C2 C1 106.9(5) . . ? N1 C3 C4 109.9(5) . . ? N3 C4 C3 108.3(6) . . ? N1 C5 C6 108.4(5) . . ? N4 C6 C5 108.2(5) . . ? O2 C7 O1 124.7(6) . . ? O2 C7 C8 118.5(7) . . ? O1 C7 C8 116.8(5) . . ? N5 C8 C9 115.0(4) . . ? N5 C8 C7 108.2(5) . . ? C9 C8 C7 113.1(5) . . ? C10 C9 C8 111.4(6) . . ? C11 C10 N6 109.3(6) . . ? C11 C10 C9 128.1(7) . . ? N6 C10 C9 122.6(5) . . ? C10 C11 N7 105.8(7) . . ? N6 C12 N7 112.1(7) . . ? C5 N1 C3 110.9(5) . . ? C5 N1 C1 111.5(4) . . ? C3 N1 C1 112.1(5) . . ? C5 N1 Co 106.0(4) . . ? C3 N1 Co 110.4(4) . . ? C1 N1 Co 105.6(4) . . ? C2 N2 Co 111.2(4) . . ? C4 N3 Co 109.4(4) . . ? C6 N4 Co 110.8(4) . . ? C8 N5 Co 109.7(3) . . ? C12 N6 C10 105.1(6) . . ? C12 N7 C11 107.6(5) . . ? C7 O1 Co 115.6(3) . . ? O6 Cl1 O3 108.0(4) . . ? O6 Cl1 O5 112.7(4) . . ? O3 Cl1 O5 106.7(4) . . ? O6 Cl1 O4 109.6(4) . . ? O3 Cl1 O4 109.7(4) . . ? O5 Cl1 O4 110.0(4) . . ? O8 Cl2 O9 113.8(8) . . ? O8 Cl2 O7 110.8(6) . . ? O9 Cl2 O7 103.5(8) . . ? O8 Cl2 O10 111.7(4) . . ? O9 Cl2 O10 107.6(5) . . ? O7 Cl2 O10 109.0(5) . . ? O1 Co N1 92.0(2) . . ? O1 Co N3 178.6(2) . . ? N1 Co N3 86.8(2) . . ? O1 Co N5 85.2(2) . . ? N1 Co N5 176.57(19) . . ? N3 Co N5 96.0(2) . . ? O1 Co N4 87.46(17) . . ? N1 Co N4 86.5(2) . . ? N3 Co N4 91.79(19) . . ? N5 Co N4 95.3(2) . . ? O1 Co N2 86.71(18) . . ? N1 Co N2 86.8(2) . . ? N3 Co N2 93.9(2) . . ? N5 Co N2 91.1(2) . . ? N4 Co N2 170.98(19) . . ? 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 N1 C1 C2 N2 46.2(7) . . . . ? N1 C3 C4 N3 -40.1(6) . . . . ? N1 C5 C6 N4 -45.1(7) . . . . ? O2 C7 C8 N5 165.0(4) . . . . ? O1 C7 C8 N5 -17.3(6) . . . . ? O2 C7 C8 C9 36.4(7) . . . . ? O1 C7 C8 C9 -145.9(5) . . . . ? N5 C8 C9 C10 -63.1(6) . . . . ? C7 C8 C9 C10 61.8(6) . . . . ? C8 C9 C10 C11 172.4(6) . . . . ? C8 C9 C10 N6 -6.8(7) . . . . ? N6 C10 C11 N7 -2.1(8) . . . . ? C9 C10 C11 N7 178.6(6) . . . . ? C6 C5 N1 C3 -73.1(7) . . . . ? C6 C5 N1 C1 161.1(6) . . . . ? C6 C5 N1 Co 46.7(6) . . . . ? C4 C3 N1 C5 138.4(6) . . . . ? C4 C3 N1 C1 -96.2(6) . . . . ? C4 C3 N1 Co 21.2(6) . . . . ? C2 C1 N1 C5 -162.6(6) . . . . ? C2 C1 N1 C3 72.4(7) . . . . ? C2 C1 N1 Co -47.9(6) . . . . ? C1 C2 N2 Co -22.9(6) . . . . ? C3 C4 N3 Co 40.3(5) . . . . ? C5 C6 N4 Co 22.1(6) . . . . ? C9 C8 N5 Co 149.7(4) . . . . ? C7 C8 N5 Co 22.3(4) . . . . ? N7 C12 N6 C10 -0.5(8) . . . . ? C11 C10 N6 C12 1.6(7) . . . . ? C9 C10 N6 C12 -179.1(6) . . . . ? N6 C12 N7 C11 -0.8(9) . . . . ? C10 C11 N7 C12 1.8(8) . . . . ? O2 C7 O1 Co -179.3(4) . . . . ? C8 C7 O1 Co 3.2(5) . . . . ? C7 O1 Co N1 -173.5(3) . . . . ? C7 O1 Co N3 -145(9) . . . . ? C7 O1 Co N5 8.4(3) . . . . ? C7 O1 Co N4 -87.1(3) . . . . ? C7 O1 Co N2 99.8(3) . . . . ? C5 N1 Co O1 59.9(3) . . . . ? C3 N1 Co O1 -179.9(4) . . . . ? C1 N1 Co O1 -58.6(4) . . . . ? C5 N1 Co N3 -119.4(4) . . . . ? C3 N1 Co N3 0.7(4) . . . . ? C1 N1 Co N3 122.1(4) . . . . ? C5 N1 Co N5 94(3) . . . . ? C3 N1 Co N5 -145(3) . . . . ? C1 N1 Co N5 -24(4) . . . . ? C5 N1 Co N4 -27.5(3) . . . . ? C3 N1 Co N4 92.7(4) . . . . ? C1 N1 Co N4 -145.9(4) . . . . ? C5 N1 Co N2 146.5(4) . . . . ? C3 N1 Co N2 -93.3(4) . . . . ? C1 N1 Co N2 28.0(4) . . . . ? C4 N3 Co O1 -53(9) . . . . ? C4 N3 Co N1 -23.6(4) . . . . ? C4 N3 Co N5 154.5(4) . . . . ? C4 N3 Co N4 -110.0(4) . . . . ? C4 N3 Co N2 63.0(4) . . . . ? C8 N5 Co O1 -17.7(3) . . . . ? C8 N5 Co N1 -52(3) . . . . ? C8 N5 Co N3 161.7(3) . . . . ? C8 N5 Co N4 69.3(3) . . . . ? C8 N5 Co N2 -104.3(3) . . . . ? C6 N4 Co O1 -89.1(4) . . . . ? C6 N4 Co N1 3.1(4) . . . . ? C6 N4 Co N3 89.7(4) . . . . ? C6 N4 Co N5 -174.0(4) . . . . ? C6 N4 Co N2 -39.4(15) . . . . ? C2 N2 Co O1 89.4(4) . . . . ? C2 N2 Co N1 -2.8(4) . . . . ? C2 N2 Co N3 -89.3(4) . . . . ? C2 N2 Co N5 174.5(4) . . . . ? C2 N2 Co N4 39.6(15) . . . . ? data_betaala1 _database_code_depnum_ccdc_archive 'CCDC 208930' _audit_creation_date 2003-04-16T11:45:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C9 H28 Cl2 Co N5 O8' _chemical_formula_weight 464.19 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 9.103(5) _cell_length_b 13.651(2) _cell_length_c 15.199(4) _cell_angle_alpha 90 _cell_angle_beta 102.50(3) _cell_angle_gamma 90 _cell_volume 1843.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.268 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1082 _diffrn_reflns_av_unetI/netI 0.1245 _diffrn_reflns_number 4374 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.08 _diffrn_reflns_theta_full 29.08 _diffrn_measured_fraction_theta_full 0.79 _diffrn_measured_fraction_theta_max 0.79 _reflns_number_total 3905 _reflns_number_gt 2058 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0930P)^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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0002(9) _refine_ls_number_reflns 3905 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1625 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1911 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.648 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.12 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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 0.4384(7) 0.4654(5) 0.7102(5) 0.0395(17) Uani 1 1 d . . . H1 H 0.5378 0.4494 0.7452 0.047 Uiso 1 1 calc R . . H2 H 0.4467 0.4784 0.6488 0.047 Uiso 1 1 calc R . . C2 C 0.3797(7) 0.5559(4) 0.7492(5) 0.0393(17) Uani 1 1 d . . . H3 H 0.4612 0.6017 0.7701 0.047 Uiso 1 1 calc R . . H4 H 0.3041 0.588 0.7036 0.047 Uiso 1 1 calc R . . C3 C 0.4240(7) 0.2892(5) 0.7424(4) 0.0372(16) Uani 1 1 d . . . H7 H 0.5072 0.2837 0.7122 0.045 Uiso 1 1 calc R . . H8 H 0.3618 0.2311 0.7291 0.045 Uiso 1 1 calc R . . C4 C 0.4818(7) 0.2995(5) 0.8426(4) 0.0370(16) Uani 1 1 d . . . H9 H 0.5248 0.238 0.8679 0.044 Uiso 1 1 calc R . . H10 H 0.5594 0.3494 0.855 0.044 Uiso 1 1 calc R . . C5 C 0.2293(7) 0.3656(5) 0.6221(4) 0.0422(17) Uani 1 1 d . . . H13 H 0.1795 0.3025 0.6201 0.051 Uiso 1 1 calc R . . H14 H 0.2854 0.3673 0.5747 0.051 Uiso 1 1 calc R . . C6 C 0.1147(7) 0.4464(5) 0.6085(5) 0.0457(18) Uani 1 1 d . . . H15 H 0.1586 0.5064 0.5914 0.055 Uiso 1 1 calc R . . H16 H 0.0295 0.429 0.5608 0.055 Uiso 1 1 calc R . . C7 C 0.0072(8) 0.3498(5) 0.9189(5) 0.0481(19) Uani 1 1 d . . . H21 H -0.0513 0.3751 0.9601 0.058 Uiso 1 1 calc R . . H22 H 0.0814 0.3047 0.9518 0.058 Uiso 1 1 calc R . . C8 C -0.0960(7) 0.2960(6) 0.8418(5) 0.0467(19) Uani 1 1 d . . . H23 H -0.1543 0.2483 0.8669 0.056 Uiso 1 1 calc R . . H24 H -0.1659 0.3428 0.8074 0.056 Uiso 1 1 calc R . . C9 C -0.0144(8) 0.2440(4) 0.7784(5) 0.0390(17) Uani 1 1 d . . . N1 N 0.3333(5) 0.3795(3) 0.7115(3) 0.0286(12) Uani 1 1 d . . . N2 N 0.3137(6) 0.5247(4) 0.8250(4) 0.0362(13) Uani 1 1 d . . . H5 H 0.2503 0.5713 0.8364 0.043 Uiso 1 1 calc R . . H6 H 0.3872 0.5171 0.8746 0.043 Uiso 1 1 calc R . . N3 N 0.3544(5) 0.3272(4) 0.8832(3) 0.0339(13) Uani 1 1 d . . . H11 H 0.3882 0.3636 0.9329 0.041 Uiso 1 1 calc R . . H12 H 0.3112 0.2729 0.8997 0.041 Uiso 1 1 calc R . . N4 N 0.0649(6) 0.4612(4) 0.6938(3) 0.0355(13) Uani 1 1 d . . . H17 H -0.0269 0.4344 0.689 0.043 Uiso 1 1 calc R . . H18 H 0.0572 0.5258 0.7037 0.043 Uiso 1 1 calc R . . N5 N 0.0843(6) 0.4318(4) 0.8835(4) 0.0381(14) Uani 1 1 d . . . H19 H 0.144 0.4618 0.9308 0.046 Uiso 1 1 calc R . . H20 H 0.0137 0.4754 0.858 0.046 Uiso 1 1 calc R . . O1 O 0.1065(4) 0.2799(3) 0.7626(3) 0.0322(10) Uani 1 1 d . . . O2 O -0.0653(5) 0.1652(3) 0.7442(4) 0.0513(14) Uani 1 1 d . . . O3 O -0.4072(10) 0.2592(6) 0.5576(5) 0.130(4) Uani 1 1 d . . . O4 O -0.3811(15) 0.4075(8) 0.4992(7) 0.198(6) Uani 1 1 d . . . O5 O -0.2510(6) 0.3751(4) 0.6402(4) 0.0666(17) Uani 1 1 d . . . O6 O -0.1909(11) 0.3091(10) 0.5163(8) 0.212(7) Uani 1 1 d . . . O7 O 0.1722(6) 0.0597(4) 0.7073(4) 0.0580(14) Uani 1 1 d . . . O8 O 0.2692(7) 0.1132(4) 0.8968(4) 0.078(2) Uani 1 1 d . . . Cl1 Cl -0.3056(2) 0.33354(17) 0.55388(14) 0.0606(6) Uani 1 1 d . . . Cl2 Cl 0.3391(2) 0.47330(17) 1.05783(13) 0.0586(6) Uani 1 1 d . . . Co Co 0.20547(9) 0.40214(6) 0.79680(6) 0.0278(3) 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 0.031(3) 0.036(4) 0.053(4) 0.000(3) 0.011(3) -0.006(3) C2 0.035(3) 0.024(3) 0.059(5) 0.002(3) 0.010(3) -0.005(3) C3 0.037(3) 0.035(4) 0.044(4) -0.001(3) 0.019(3) 0.011(3) C4 0.032(3) 0.037(4) 0.041(4) 0.003(3) 0.005(3) 0.009(3) C5 0.042(4) 0.056(4) 0.027(3) 0.006(3) 0.004(3) -0.005(3) C6 0.045(4) 0.052(4) 0.036(4) 0.006(4) -0.001(3) 0.002(4) C7 0.049(4) 0.055(5) 0.043(4) 0.001(4) 0.015(3) 0.000(4) C8 0.037(4) 0.051(4) 0.055(5) -0.006(4) 0.017(3) -0.019(3) C9 0.046(4) 0.023(3) 0.046(4) 0.002(3) 0.007(3) -0.001(3) N1 0.029(3) 0.028(3) 0.030(3) 0.006(2) 0.011(2) -0.005(2) N2 0.032(3) 0.030(3) 0.046(3) -0.007(3) 0.007(3) 0.001(2) N3 0.038(3) 0.033(3) 0.028(3) 0.002(2) 0.003(2) 0.005(2) N4 0.034(3) 0.032(3) 0.036(3) 0.004(3) -0.002(2) 0.001(2) N5 0.038(3) 0.036(3) 0.037(3) -0.008(3) 0.001(3) 0.006(2) O1 0.029(2) 0.026(2) 0.044(3) -0.004(2) 0.0130(19) -0.0071(18) O2 0.047(3) 0.035(3) 0.069(4) -0.007(3) 0.008(3) -0.010(2) O3 0.169(8) 0.158(8) 0.069(4) -0.032(5) 0.041(5) -0.127(7) O4 0.253(12) 0.163(9) 0.121(8) 0.047(7) -0.086(9) -0.066(9) O5 0.061(3) 0.083(4) 0.052(3) -0.022(3) 0.004(3) -0.013(3) O6 0.155(9) 0.298(16) 0.228(12) -0.188(12) 0.139(9) -0.105(10) O7 0.062(3) 0.053(3) 0.063(4) 0.000(3) 0.024(3) -0.006(3) O8 0.103(5) 0.054(4) 0.068(4) 0.003(3) 0.002(4) 0.005(3) Cl1 0.0582(12) 0.0812(15) 0.0429(11) -0.0128(11) 0.0118(10) -0.0238(11) Cl2 0.0462(10) 0.0834(15) 0.0452(11) -0.0163(11) 0.0081(9) -0.0094(10) Co 0.0267(4) 0.0245(4) 0.0315(4) -0.0007(4) 0.0049(3) 0.0002(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.516(9) . ? C1 N1 1.517(7) . ? C2 N2 1.471(9) . ? C3 N1 1.501(7) . ? C3 C4 1.506(9) . ? C4 N3 1.476(8) . ? C5 N1 1.490(7) . ? C5 C6 1.502(9) . ? C6 N4 1.477(9) . ? C7 N5 1.482(9) . ? C7 C8 1.523(9) . ? C8 C9 1.515(10) . ? C9 O2 1.239(7) . ? C9 O1 1.274(8) . ? N1 Co 1.945(5) . ? N2 Co 1.942(5) . ? N3 Co 1.959(5) . ? N4 Co 1.968(5) . ? N5 Co 1.935(6) . ? O1 Co 1.915(4) . ? O3 Cl1 1.382(6) . ? O4 Cl1 1.391(10) . ? O5 Cl1 1.417(5) . ? O6 Cl1 1.336(9) . ? 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 C2 C1 N1 110.4(5) . . ? N2 C2 C1 108.0(5) . . ? N1 C3 C4 106.7(5) . . ? N3 C4 C3 108.2(5) . . ? N1 C5 C6 108.5(6) . . ? N4 C6 C5 108.4(5) . . ? N5 C7 C8 110.3(6) . . ? C9 C8 C7 114.2(6) . . ? O2 C9 O1 120.9(7) . . ? O2 C9 C8 118.9(7) . . ? O1 C9 C8 120.1(6) . . ? C5 N1 C3 112.2(5) . . ? C5 N1 C1 111.4(5) . . ? C3 N1 C1 109.5(5) . . ? C5 N1 Co 105.9(4) . . ? C3 N1 Co 106.9(4) . . ? C1 N1 Co 110.8(4) . . ? C2 N2 Co 110.5(4) . . ? C4 N3 Co 110.2(4) . . ? C6 N4 Co 111.8(4) . . ? C7 N5 Co 118.2(4) . . ? C9 O1 Co 131.2(4) . . ? O6 Cl1 O3 115.2(7) . . ? O6 Cl1 O4 104.8(9) . . ? O3 Cl1 O4 108.0(6) . . ? O6 Cl1 O5 110.2(5) . . ? O3 Cl1 O5 111.1(4) . . ? O4 Cl1 O5 107.0(5) . . ? O1 Co N5 93.7(2) . . ? O1 Co N2 176.0(2) . . ? N5 Co N2 90.4(2) . . ? O1 Co N1 89.66(19) . . ? N5 Co N1 176.7(2) . . ? N2 Co N1 86.3(2) . . ? O1 Co N3 86.8(2) . . ? N5 Co N3 93.8(2) . . ? N2 Co N3 93.3(2) . . ? N1 Co N3 86.4(2) . . ? O1 Co N4 87.4(2) . . ? N5 Co N4 95.0(2) . . ? N2 Co N4 91.9(2) . . ? N1 Co N4 85.1(2) . . ? N3 Co N4 169.7(2) . . ? 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 N1 C1 C2 N2 37.6(7) . . . . ? N1 C3 C4 N3 48.8(7) . . . . ? N1 C5 C6 N4 -42.6(7) . . . . ? N5 C7 C8 C9 65.5(8) . . . . ? C7 C8 C9 O2 145.2(6) . . . . ? C7 C8 C9 O1 -33.1(10) . . . . ? C6 C5 N1 C3 164.3(5) . . . . ? C6 C5 N1 C1 -72.6(7) . . . . ? C6 C5 N1 Co 48.0(6) . . . . ? C4 C3 N1 C5 -161.1(5) . . . . ? C4 C3 N1 C1 74.7(6) . . . . ? C4 C3 N1 Co -45.4(6) . . . . ? C2 C1 N1 C5 98.3(6) . . . . ? C2 C1 N1 C3 -137.1(5) . . . . ? C2 C1 N1 Co -19.4(6) . . . . ? C1 C2 N2 Co -39.1(5) . . . . ? C3 C4 N3 Co -29.3(6) . . . . ? C5 C6 N4 Co 17.3(6) . . . . ? C8 C7 N5 Co -57.7(7) . . . . ? O2 C9 O1 Co 174.8(4) . . . . ? C8 C9 O1 Co -6.9(9) . . . . ? C9 O1 Co N5 12.7(6) . . . . ? C9 O1 Co N2 -163(3) . . . . ? C9 O1 Co N1 -167.3(6) . . . . ? C9 O1 Co N3 106.3(6) . . . . ? C9 O1 Co N4 -82.2(6) . . . . ? C7 N5 Co O1 20.8(4) . . . . ? C7 N5 Co N2 -159.5(4) . . . . ? C7 N5 Co N1 -159(3) . . . . ? C7 N5 Co N3 -66.2(4) . . . . ? C7 N5 Co N4 108.5(4) . . . . ? C2 N2 Co O1 19(3) . . . . ? C2 N2 Co N5 -156.5(4) . . . . ? C2 N2 Co N1 23.5(4) . . . . ? C2 N2 Co N3 109.7(4) . . . . ? C2 N2 Co N4 -61.5(4) . . . . ? C5 N1 Co O1 56.9(4) . . . . ? C3 N1 Co O1 -63.0(4) . . . . ? C1 N1 Co O1 177.8(4) . . . . ? C5 N1 Co N5 -123(3) . . . . ? C3 N1 Co N5 117(4) . . . . ? C1 N1 Co N5 -2(4) . . . . ? C5 N1 Co N2 -122.8(4) . . . . ? C3 N1 Co N2 117.3(4) . . . . ? C1 N1 Co N2 -1.9(4) . . . . ? C5 N1 Co N3 143.7(4) . . . . ? C3 N1 Co N3 23.8(4) . . . . ? C1 N1 Co N3 -95.4(4) . . . . ? C5 N1 Co N4 -30.5(4) . . . . ? C3 N1 Co N4 -150.4(4) . . . . ? C1 N1 Co N4 90.4(4) . . . . ? C4 N3 Co O1 92.9(4) . . . . ? C4 N3 Co N5 -173.6(4) . . . . ? C4 N3 Co N2 -83.1(4) . . . . ? C4 N3 Co N1 3.0(4) . . . . ? C4 N3 Co N4 37.3(14) . . . . ? C6 N4 Co O1 -82.3(4) . . . . ? C6 N4 Co N5 -175.7(4) . . . . ? C6 N4 Co N2 93.8(4) . . . . ? C6 N4 Co N1 7.6(4) . . . . ? C6 N4 Co N3 -26.7(15) . . . . ? data_clevco2 _database_code_depnum_ccdc_archive 'CCDC 208933' _audit_creation_date 2003-04-16T12:51:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C12 H30 Cl2 Co N7 O12' _chemical_formula_weight 594.26 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.884(4) _cell_length_b 11.473(6) _cell_length_c 18.104(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2260.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# #_exptl_absorpt_coefficient_mu 1.07 _exptl_absorpt_correction_type Difabs _exptl_absorpt_coefficient_mu ; 1.07 [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.6971 _exptl_absorpt_correction_T_max 0.8964 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_unetI/netI 0.0343 _diffrn_reflns_number 2945 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2771 _reflns_number_gt 2227 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0777P)^2^+2.0750P] 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_number_reflns 2771 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_diff_density_max 0.687 _refine_diff_density_min -0.5 _refine_diff_density_rms 0.083 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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 Co Co 0.30246(7) 0.13649(7) 0.19420(4) 0.0294(2) Uani 1 1 d . . . Cl02 Cl -0.04180(16) -0.08798(17) 0.03422(9) 0.0477(4) Uani 1 1 d . . . Cl03 Cl -0.13668(17) 0.31556(16) 0.09729(10) 0.0485(4) Uani 1 1 d . . . O2 O 0.3892(4) -0.1447(4) 0.2685(3) 0.0477(11) Uani 1 1 d . . . N7 N 0.6145(5) 0.0295(5) 0.0898(3) 0.0453(14) Uani 1 1 d . . . O3 O -0.0911(5) 0.3699(6) 0.1625(3) 0.0702(15) Uani 1 1 d . . . N1 N 0.3917(5) 0.1003(5) 0.2853(3) 0.0384(12) Uani 1 1 d . . . H1 H 0.3995 0.0225 0.2896 0.046 Uiso 1 1 calc R . . H2 H 0.4676 0.1311 0.2828 0.046 Uiso 1 1 calc R . . N2 N 0.1779(5) 0.2063(4) 0.2597(3) 0.0388(12) Uani 1 1 d . . . H7 H 0.1027 0.1842 0.2428 0.047 Uiso 1 1 calc R . . N6 N 0.4349(5) 0.0664(4) 0.1368(3) 0.0341(11) Uani 1 1 d . . . N3 N 0.3746(5) 0.2935(4) 0.1876(3) 0.0378(11) Uani 1 1 d . . . H12 H 0.4559 0.288 0.1988 0.045 Uiso 1 1 calc R . . O1 O 0.3683(5) -0.2957(4) 0.1932(3) 0.0541(12) Uani 1 1 d . . . N5 N 0.2121(4) -0.0157(4) 0.2006(3) 0.0342(10) Uani 1 1 d . . . H20 H 0.2048 -0.0319 0.249 0.041 Uiso 1 1 calc R . . H19 H 0.1356 -0.0017 0.1839 0.041 Uiso 1 1 calc R . . N4 N 0.2145(5) 0.1792(4) 0.1020(3) 0.0380(12) Uani 1 1 d . . . H18 H 0.2408 0.1335 0.0649 0.046 Uiso 1 1 calc R . . H17 H 0.1335 0.1666 0.108 0.046 Uiso 1 1 calc R . . O5 O -0.1936(6) 0.2077(5) 0.1175(4) 0.0781(17) Uani 1 1 d . . . O6 O -0.0398(7) 0.2922(7) 0.0472(4) 0.095(2) Uani 1 1 d . . . OW2 O 0.1758(8) 0.5885(6) 0.1302(4) 0.098(2) Uani 1 1 d . . . OW1 O -0.0531(6) 0.0989(5) 0.2366(4) 0.0822(19) Uani 1 1 d . . . O4 O -0.2253(7) 0.3886(6) 0.0631(4) 0.098(2) Uani 1 1 d . . . C9 C 0.4262(6) -0.0333(6) 0.0950(3) 0.0375(14) Uani 1 1 d . . . C7 C 0.2530(6) -0.1261(5) 0.1642(3) 0.0368(13) Uani 1 1 d . . . H21 H 0.1804 -0.1752 0.1568 0.044 Uiso 1 1 calc R . . C10 C 0.5382(7) -0.0585(6) 0.0663(3) 0.0444(16) Uani 1 1 d . . . H24 H 0.5591 -0.122 0.0369 0.053 Uiso 1 1 calc R . . C8 C 0.3092(6) -0.1021(5) 0.0889(3) 0.0365(13) Uani 1 1 d . . . H22 H 0.326 -0.1756 0.0643 0.044 Uiso 1 1 calc R . . H23 H 0.2508 -0.0592 0.0589 0.044 Uiso 1 1 calc R . . C3 C 0.1845(7) 0.3349(5) 0.2554(4) 0.0463(16) Uani 1 1 d . . . H8 H 0.1543 0.3687 0.301 0.056 Uiso 1 1 calc R . . H9 H 0.1332 0.3626 0.2153 0.056 Uiso 1 1 calc R . . C4 C 0.3158(7) 0.3721(5) 0.2427(4) 0.0463(15) Uani 1 1 d . . . H11 H 0.3176 0.4517 0.2248 0.056 Uiso 1 1 calc R . . H10 H 0.3609 0.369 0.2889 0.056 Uiso 1 1 calc R . . C6 C 0.2351(7) 0.3029(6) 0.0824(4) 0.0483(18) Uani 1 1 d . . . H15 H 0.1741 0.3519 0.1061 0.058 Uiso 1 1 calc R . . H16 H 0.2288 0.3134 0.0294 0.058 Uiso 1 1 calc R . . C2 C 0.1930(7) 0.1579(6) 0.3346(4) 0.0486(17) Uani 1 1 d . . . H5 H 0.1539 0.0821 0.3374 0.058 Uiso 1 1 calc R . . H6 H 0.154 0.2089 0.3703 0.058 Uiso 1 1 calc R . . C1 C 0.3280(7) 0.1466(7) 0.3519(3) 0.0520(18) Uani 1 1 d . . . H4 H 0.3617 0.222 0.3651 0.062 Uiso 1 1 calc R . . H3 H 0.3397 0.094 0.3933 0.062 Uiso 1 1 calc R . . C12 C 0.3443(6) -0.1943(6) 0.2136(4) 0.0401(15) Uani 1 1 d . . . C5 C 0.3633(7) 0.3350(6) 0.1090(4) 0.0446(16) Uani 1 1 d . . . H13 H 0.425 0.2978 0.0783 0.054 Uiso 1 1 calc R . . H14 H 0.3751 0.4187 0.1065 0.054 Uiso 1 1 calc R . . C11 C 0.5509(6) 0.1015(6) 0.1323(4) 0.0403(14) Uani 1 1 d . . . H26 H 0.5827 0.1671 0.1557 0.048 Uiso 1 1 calc R . . O8 O -0.1679(6) -0.0845(11) 0.0352(6) 0.151(4) Uani 1 1 d . . . O10 O 0.0079(7) -0.1994(7) 0.0396(6) 0.122(3) Uani 1 1 d . . . O7 O -0.0050(10) -0.0353(11) 0.0980(8) 0.184(6) Uani 1 1 d . . . O9 O 0.0097(14) -0.0308(16) -0.0190(8) 0.292(12) Uani 1 1 d . . . H25 H 0.687(9) 0.035(9) 0.080(5) 0.08(3) Uiso 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 Co 0.0293(4) 0.0285(3) 0.0305(3) -0.0019(3) -0.0017(3) 0.0011(3) Cl02 0.0415(9) 0.0596(10) 0.0420(8) 0.0021(8) 0.0054(7) 0.0054(8) Cl03 0.0475(9) 0.0515(9) 0.0466(9) -0.0075(8) -0.0012(8) 0.0007(8) O2 0.051(3) 0.041(2) 0.051(3) 0.004(2) -0.017(2) 0.004(2) N7 0.036(3) 0.050(3) 0.050(3) 0.007(3) 0.008(3) 0.001(3) O3 0.073(3) 0.077(4) 0.061(3) -0.028(3) -0.015(3) 0.003(4) N1 0.036(3) 0.042(3) 0.037(3) 0.005(2) -0.007(2) -0.004(2) N2 0.032(3) 0.043(3) 0.041(3) -0.005(2) 0.002(2) 0.001(2) N6 0.031(2) 0.033(3) 0.039(3) 0.003(2) -0.001(2) -0.003(2) N3 0.036(3) 0.035(2) 0.042(3) -0.001(2) -0.002(3) -0.001(2) O1 0.059(3) 0.038(2) 0.065(3) -0.002(2) -0.009(3) 0.016(2) N5 0.028(2) 0.033(2) 0.041(3) 0.001(2) -0.003(2) -0.001(2) N4 0.038(3) 0.033(2) 0.043(3) -0.002(2) -0.006(2) 0.003(2) O5 0.076(4) 0.072(4) 0.086(4) -0.001(3) -0.013(4) -0.024(4) O6 0.079(4) 0.120(6) 0.085(4) -0.037(4) 0.028(4) -0.015(5) OW2 0.131(7) 0.055(3) 0.108(5) -0.010(4) -0.027(5) 0.002(4) OW1 0.062(3) 0.069(4) 0.115(5) 0.022(4) -0.023(4) -0.013(3) O4 0.120(6) 0.082(5) 0.093(5) -0.004(4) -0.044(5) 0.037(5) C9 0.043(3) 0.037(3) 0.033(3) 0.000(3) -0.002(3) 0.009(3) C7 0.034(3) 0.031(3) 0.045(3) 0.000(3) -0.007(3) 0.002(3) C10 0.055(4) 0.046(4) 0.032(3) -0.006(3) 0.005(3) 0.005(3) C8 0.041(3) 0.028(3) 0.040(3) -0.002(2) -0.008(3) 0.005(3) C3 0.059(4) 0.032(3) 0.048(4) -0.005(3) 0.002(3) 0.014(3) C4 0.066(4) 0.030(3) 0.042(3) -0.007(3) 0.002(3) 0.008(4) C6 0.070(5) 0.038(3) 0.037(3) -0.002(3) -0.016(3) 0.008(3) C2 0.067(4) 0.042(4) 0.037(3) 0.001(3) 0.015(3) 0.006(4) C1 0.077(5) 0.046(4) 0.033(3) 0.001(3) -0.004(3) -0.006(4) C12 0.035(3) 0.041(3) 0.044(4) 0.008(3) 0.001(3) 0.000(3) C5 0.058(4) 0.034(3) 0.042(4) 0.006(3) 0.006(3) -0.001(3) C11 0.038(3) 0.034(3) 0.049(4) 0.001(3) 0.007(3) 0.001(3) O8 0.051(4) 0.214(11) 0.188(9) -0.060(9) 0.009(5) 0.019(6) O10 0.087(5) 0.061(4) 0.218(10) -0.017(5) 0.021(6) 0.010(4) O7 0.127(8) 0.177(10) 0.248(13) -0.125(10) -0.098(9) 0.048(8) O9 0.244(15) 0.40(2) 0.235(13) 0.245(15) 0.182(12) 0.223(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Co N6 1.951(5) . ? Co N1 1.959(5) . ? Co N3 1.969(5) . ? Co N2 1.972(5) . ? Co N4 1.985(5) . ? Co N5 2.007(5) . ? Cl02 O9 1.293(10) . ? Cl02 O7 1.364(10) . ? Cl02 O8 1.373(7) . ? Cl02 O10 1.391(8) . ? Cl03 O6 1.416(6) . ? Cl03 O4 1.420(7) . ? Cl03 O3 1.425(5) . ? Cl03 O5 1.431(6) . ? O2 C12 1.245(8) . ? N7 C11 1.325(9) . ? N7 C10 1.375(9) . ? N1 C1 1.489(8) . ? N2 C2 1.473(8) . ? N2 C3 1.479(8) . ? N6 C11 1.327(8) . ? N6 C9 1.375(8) . ? N3 C4 1.489(8) . ? N3 C5 1.506(8) . ? O1 C12 1.249(8) . ? N5 C7 1.496(8) . ? N4 C6 1.479(8) . ? C9 C10 1.356(9) . ? C9 C8 1.503(9) . ? C7 C8 1.520(9) . ? C7 C12 1.548(9) . ? C3 C4 1.509(11) . ? C6 C5 1.522(10) . ? C2 C1 1.509(11) . ? 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 N6 Co N1 89.7(2) . . ? N6 Co N3 92.9(2) . . ? N1 Co N3 92.7(2) . . ? N6 Co N2 175.1(2) . . ? N1 Co N2 85.4(2) . . ? N3 Co N2 86.5(2) . . ? N6 Co N4 90.6(2) . . ? N1 Co N4 177.9(2) . . ? N3 Co N4 85.1(2) . . ? N2 Co N4 94.2(2) . . ? N6 Co N5 92.0(2) . . ? N1 Co N5 90.6(2) . . ? N3 Co N5 174.2(2) . . ? N2 Co N5 89.0(2) . . ? N4 Co N5 91.5(2) . . ? O9 Cl02 O7 106.1(12) . . ? O9 Cl02 O8 115.3(8) . . ? O7 Cl02 O8 105.6(7) . . ? O9 Cl02 O10 110.5(7) . . ? O7 Cl02 O10 103.5(7) . . ? O8 Cl02 O10 114.5(7) . . ? O6 Cl03 O4 109.8(5) . . ? O6 Cl03 O3 110.7(4) . . ? O4 Cl03 O3 109.9(4) . . ? O6 Cl03 O5 108.8(5) . . ? O4 Cl03 O5 109.2(4) . . ? O3 Cl03 O5 108.5(4) . . ? C11 N7 C10 108.8(6) . . ? C1 N1 Co 112.1(4) . . ? C2 N2 C3 114.8(5) . . ? C2 N2 Co 108.9(4) . . ? C3 N2 Co 109.9(4) . . ? C11 N6 C9 106.6(5) . . ? C11 N6 Co 127.6(4) . . ? C9 N6 Co 125.8(4) . . ? C4 N3 C5 114.0(5) . . ? C4 N3 Co 110.0(4) . . ? C5 N3 Co 108.3(4) . . ? C7 N5 Co 124.5(4) . . ? C6 N4 Co 111.4(4) . . ? C10 C9 N6 109.0(6) . . ? C10 C9 C8 128.5(6) . . ? N6 C9 C8 122.4(5) . . ? N5 C7 C8 111.2(5) . . ? N5 C7 C12 111.4(5) . . ? C8 C7 C12 110.6(5) . . ? C9 C10 N7 105.6(6) . . ? C9 C8 C7 111.7(5) . . ? N2 C3 C4 109.6(6) . . ? N3 C4 C3 109.8(5) . . ? N4 C6 C5 107.2(5) . . ? N2 C2 C1 109.4(6) . . ? N1 C1 C2 108.4(5) . . ? O2 C12 O1 125.4(6) . . ? O2 C12 C7 118.8(6) . . ? O1 C12 C7 115.7(6) . . ? N3 C5 C6 107.2(5) . . ? N7 C11 N6 110.0(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 N6 Co N1 C1 176.1(4) . . . . ? N3 Co N1 C1 83.2(5) . . . . ? N2 Co N1 C1 -3.1(5) . . . . ? N4 Co N1 C1 78(6) . . . . ? N5 Co N1 C1 -92.0(5) . . . . ? N6 Co N2 C2 -31(3) . . . . ? N1 Co N2 C2 -20.4(4) . . . . ? N3 Co N2 C2 -113.5(4) . . . . ? N4 Co N2 C2 161.7(4) . . . . ? N5 Co N2 C2 70.2(4) . . . . ? N6 Co N2 C3 96(3) . . . . ? N1 Co N2 C3 106.0(5) . . . . ? N3 Co N2 C3 13.0(5) . . . . ? N4 Co N2 C3 -71.8(5) . . . . ? N5 Co N2 C3 -163.3(5) . . . . ? N1 Co N6 C11 -63.6(5) . . . . ? N3 Co N6 C11 29.2(5) . . . . ? N2 Co N6 C11 -53(3) . . . . ? N4 Co N6 C11 114.3(5) . . . . ? N5 Co N6 C11 -154.1(5) . . . . ? N1 Co N6 C9 113.6(5) . . . . ? N3 Co N6 C9 -153.7(5) . . . . ? N2 Co N6 C9 124(2) . . . . ? N4 Co N6 C9 -68.5(5) . . . . ? N5 Co N6 C9 23.0(5) . . . . ? N6 Co N3 C4 -165.1(4) . . . . ? N1 Co N3 C4 -75.2(4) . . . . ? N2 Co N3 C4 10.0(4) . . . . ? N4 Co N3 C4 104.6(4) . . . . ? N5 Co N3 C4 49(2) . . . . ? N6 Co N3 C5 69.7(4) . . . . ? N1 Co N3 C5 159.5(4) . . . . ? N2 Co N3 C5 -115.2(4) . . . . ? N4 Co N3 C5 -20.7(4) . . . . ? N5 Co N3 C5 -76(2) . . . . ? N6 Co N5 C7 -2.9(5) . . . . ? N1 Co N5 C7 -92.6(5) . . . . ? N3 Co N5 C7 142.8(19) . . . . ? N2 Co N5 C7 -178.0(5) . . . . ? N4 Co N5 C7 87.8(5) . . . . ? N6 Co N4 C6 -99.4(5) . . . . ? N1 Co N4 C6 -1(7) . . . . ? N3 Co N4 C6 -6.6(5) . . . . ? N2 Co N4 C6 79.6(5) . . . . ? N5 Co N4 C6 168.6(5) . . . . ? C11 N6 C9 C10 0.8(7) . . . . ? Co N6 C9 C10 -176.8(4) . . . . ? C11 N6 C9 C8 177.4(6) . . . . ? Co N6 C9 C8 -0.2(8) . . . . ? Co N5 C7 C8 -37.5(6) . . . . ? Co N5 C7 C12 86.4(6) . . . . ? N6 C9 C10 N7 -1.6(7) . . . . ? C8 C9 C10 N7 -177.9(6) . . . . ? C11 N7 C10 C9 1.8(7) . . . . ? C10 C9 C8 C7 126.8(7) . . . . ? N6 C9 C8 C7 -49.0(7) . . . . ? N5 C7 C8 C9 65.5(6) . . . . ? C12 C7 C8 C9 -58.8(7) . . . . ? C2 N2 C3 C4 90.1(7) . . . . ? Co N2 C3 C4 -33.0(7) . . . . ? C5 N3 C4 C3 91.3(6) . . . . ? Co N3 C4 C3 -30.6(6) . . . . ? N2 C3 C4 N3 41.7(7) . . . . ? Co N4 C6 C5 31.8(6) . . . . ? C3 N2 C2 C1 -84.0(7) . . . . ? Co N2 C2 C1 39.6(6) . . . . ? Co N1 C1 C2 25.3(7) . . . . ? N2 C2 C1 N1 -42.2(7) . . . . ? N5 C7 C12 O2 -12.3(8) . . . . ? C8 C7 C12 O2 111.9(7) . . . . ? N5 C7 C12 O1 169.1(5) . . . . ? C8 C7 C12 O1 -66.7(7) . . . . ? C4 N3 C5 C6 -79.7(6) . . . . ? Co N3 C5 C6 43.1(5) . . . . ? N4 C6 C5 N3 -48.4(6) . . . . ? C10 N7 C11 N6 -1.3(7) . . . . ? C9 N6 C11 N7 0.3(7) . . . . ? Co N6 C11 N7 177.9(4) . . . . ?