# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_v262 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H35 Cl6 Co N3' _chemical_formula_weight 697.23 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.8565(12) _cell_length_b 14.5920(18) _cell_length_c 26.249(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.697(3) _cell_angle_gamma 90.00 _cell_volume 3388.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1886 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 17.74 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8096 _exptl_absorpt_correction_T_max 0.9241 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19836 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_unetI/netI 0.0826 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.08 _reflns_number_total 6026 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0715P)^2^] 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 6026 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1292 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.07409(7) 0.58013(4) 0.21633(3) 0.0490(2) Uani 1 1 d . . . Cl1 Cl 0.16418(18) 0.69481(10) 0.26693(5) 0.0758(5) Uani 1 1 d . . . Cl2 Cl -0.13945(14) 0.61108(9) 0.16773(5) 0.0617(4) Uani 1 1 d . . . N1 N 0.1867(4) 0.4581(2) 0.21506(14) 0.0436(9) Uani 1 1 d . . . N2 N 0.2327(4) 0.5921(3) 0.15155(14) 0.0487(10) Uani 1 1 d . . . N3 N -0.0269(4) 0.4975(3) 0.27748(14) 0.0485(10) Uani 1 1 d . . . C1 C 0.2882(5) 0.4417(3) 0.17969(19) 0.0489(12) Uani 1 1 d . . . C2 C 0.3581(5) 0.3574(3) 0.17666(19) 0.0534(13) Uani 1 1 d . . . H2 H 0.4284 0.3464 0.1522 0.064 Uiso 1 1 calc R . . C3 C 0.3210(6) 0.2898(3) 0.2109(2) 0.0583(14) Uani 1 1 d . . . H3 H 0.3664 0.2325 0.2092 0.070 Uiso 1 1 calc R . . C4 C 0.2187(6) 0.3062(3) 0.2470(2) 0.0568(13) Uani 1 1 d . . . H4 H 0.1940 0.2606 0.2699 0.068 Uiso 1 1 calc R . . C5 C 0.1516(5) 0.3927(3) 0.24916(18) 0.0458(12) Uani 1 1 d . . . C6 C 0.3138(5) 0.5209(3) 0.14481(18) 0.0516(13) Uani 1 1 d . . . C7 C 0.4294(6) 0.5106(4) 0.1059(2) 0.0771(17) Uani 1 1 d . . . H7A H 0.4275 0.5635 0.0841 0.116 Uiso 1 1 calc R . . H7B H 0.4077 0.4568 0.0858 0.116 Uiso 1 1 calc R . . H7C H 0.5277 0.5048 0.1226 0.116 Uiso 1 1 calc R . . C8 C 0.2444(5) 0.6692(3) 0.11751(18) 0.0479(12) Uani 1 1 d . . . C9 C 0.1552(6) 0.6705(3) 0.07250(19) 0.0545(13) Uani 1 1 d . . . C10 C 0.1576(6) 0.7499(4) 0.0426(2) 0.0664(15) Uani 1 1 d . . . H10 H 0.0984 0.7521 0.0124 0.080 Uiso 1 1 calc R . . C11 C 0.2447(7) 0.8247(4) 0.0564(2) 0.0674(15) Uani 1 1 d . . . C12 C 0.3356(6) 0.8191(3) 0.1002(2) 0.0629(15) Uani 1 1 d . . . H12 H 0.3970 0.8687 0.1093 0.076 Uiso 1 1 calc R . . C13 C 0.3393(5) 0.7417(3) 0.13167(19) 0.0523(13) Uani 1 1 d . . . C14 C 0.0633(6) 0.5891(4) 0.0542(2) 0.0746(17) Uani 1 1 d . . . H14A H 0.1299 0.5397 0.0463 0.112 Uiso 1 1 calc R . . H14B H 0.0033 0.6057 0.0242 0.112 Uiso 1 1 calc R . . H14C H -0.0018 0.5701 0.0805 0.112 Uiso 1 1 calc R . . C15 C 0.4470(6) 0.7369(4) 0.1779(2) 0.0718(16) Uani 1 1 d . . . H15A H 0.3923 0.7206 0.2072 0.108 Uiso 1 1 calc R . . H15B H 0.4942 0.7955 0.1833 0.108 Uiso 1 1 calc R . . H15C H 0.5230 0.6915 0.1724 0.108 Uiso 1 1 calc R . . C16 C 0.2450(8) 0.9097(4) 0.0232(2) 0.104(2) Uani 1 1 d . . . H16A H 0.2274 0.8925 -0.0118 0.156 Uiso 1 1 calc R . . H16B H 0.3412 0.9397 0.0275 0.156 Uiso 1 1 calc R . . H16C H 0.1667 0.9506 0.0331 0.156 Uiso 1 1 calc R . . C17 C 0.0370(5) 0.4192(3) 0.28565(18) 0.0483(12) Uani 1 1 d . . . C18 C 0.0034(6) 0.3549(3) 0.3275(2) 0.0713(16) Uani 1 1 d . . . H18A H -0.0743 0.3804 0.3475 0.107 Uiso 1 1 calc R . . H18B H 0.0931 0.3454 0.3489 0.107 Uiso 1 1 calc R . . H18C H -0.0302 0.2974 0.3133 0.107 Uiso 1 1 calc R . . C19 C -0.1475(5) 0.5263(3) 0.30941(18) 0.0463(12) Uani 1 1 d . . . C20 C -0.1138(6) 0.5703(3) 0.35549(19) 0.0503(12) Uani 1 1 d . . . C21 C -0.2347(7) 0.6002(3) 0.3829(2) 0.0676(15) Uani 1 1 d . . . H21 H -0.2145 0.6305 0.4136 0.081 Uiso 1 1 calc R . . C22 C -0.3843(7) 0.5869(4) 0.3666(3) 0.0752(17) Uani 1 1 d . . . C23 C -0.4107(6) 0.5417(4) 0.3211(2) 0.0696(16) Uani 1 1 d . . . H23 H -0.5103 0.5323 0.3094 0.084 Uiso 1 1 calc R . . C24 C -0.2954(6) 0.5094(3) 0.2920(2) 0.0572(14) Uani 1 1 d . . . C25 C 0.0441(6) 0.5814(4) 0.3774(2) 0.0695(16) Uani 1 1 d . . . H25A H 0.0800 0.5237 0.3907 0.104 Uiso 1 1 calc R . . H25B H 0.0451 0.6259 0.4044 0.104 Uiso 1 1 calc R . . H25C H 0.1084 0.6017 0.3513 0.104 Uiso 1 1 calc R . . C26 C -0.3310(6) 0.4556(4) 0.2441(2) 0.0821(18) Uani 1 1 d . . . H26A H -0.2999 0.4898 0.2152 0.123 Uiso 1 1 calc R . . H26B H -0.4378 0.4444 0.2407 0.123 Uiso 1 1 calc R . . H26C H -0.2780 0.3982 0.2458 0.123 Uiso 1 1 calc R . . C27 C -0.5155(8) 0.6203(5) 0.3974(3) 0.118(3) Uani 1 1 d . . . H27A H -0.5944 0.6435 0.3746 0.178 Uiso 1 1 calc R . . H27B H -0.4808 0.6681 0.4201 0.178 Uiso 1 1 calc R . . H27C H -0.5537 0.5703 0.4167 0.178 Uiso 1 1 calc R . . C28 C -0.2938(10) 0.7466(6) 0.0550(3) 0.144(3) Uani 1 1 d . . . H28A H -0.3687 0.7435 0.0808 0.172 Uiso 1 1 calc R . . H28B H -0.2006 0.7212 0.0699 0.172 Uiso 1 1 calc R . . Cl3 Cl -0.3530(4) 0.6793(2) 0.00505(12) 0.1872(12) Uani 1 1 d . . . Cl4 Cl -0.2639(3) 0.8573(2) 0.04128(11) 0.1714(11) Uani 1 1 d . . . C29 C 0.1210(10) 0.8571(5) 0.3759(3) 0.124(3) Uani 1 1 d . . . H29A H 0.1187 0.9195 0.3631 0.149 Uiso 1 1 calc R . . H29B H 0.1278 0.8160 0.3470 0.149 Uiso 1 1 calc R . . Cl5 Cl 0.2780(2) 0.84224(18) 0.41754(11) 0.1575(10) Uani 1 1 d . . . Cl6 Cl -0.0433(2) 0.83459(12) 0.40703(8) 0.1091(7) 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 0.0551(4) 0.0421(4) 0.0492(4) -0.0014(3) -0.0019(3) 0.0055(3) Cl1 0.1046(12) 0.0647(9) 0.0587(9) -0.0142(7) 0.0095(8) -0.0210(8) Cl2 0.0614(8) 0.0599(8) 0.0628(9) 0.0012(6) -0.0087(7) 0.0091(6) N1 0.047(2) 0.041(2) 0.042(2) 0.0020(19) -0.006(2) 0.0009(18) N2 0.058(3) 0.047(3) 0.041(2) -0.002(2) -0.0015(19) 0.005(2) N3 0.049(2) 0.048(3) 0.048(3) -0.001(2) -0.005(2) -0.0039(19) C1 0.044(3) 0.050(3) 0.052(3) -0.009(3) -0.004(2) 0.001(2) C2 0.053(3) 0.058(3) 0.050(3) -0.007(3) 0.000(3) 0.012(3) C3 0.064(3) 0.039(3) 0.071(4) -0.007(3) -0.008(3) 0.011(3) C4 0.061(3) 0.045(3) 0.064(4) 0.002(3) -0.002(3) 0.000(3) C5 0.046(3) 0.044(3) 0.047(3) 0.003(2) -0.006(2) -0.002(2) C6 0.054(3) 0.055(3) 0.045(3) -0.001(3) -0.002(3) 0.001(3) C7 0.087(4) 0.080(4) 0.066(4) 0.007(3) 0.027(3) 0.018(3) C8 0.056(3) 0.045(3) 0.043(3) 0.000(2) 0.007(2) 0.005(2) C9 0.065(3) 0.053(3) 0.046(3) 0.002(3) 0.006(3) 0.000(3) C10 0.090(4) 0.063(4) 0.046(3) 0.001(3) 0.002(3) 0.009(3) C11 0.101(5) 0.054(4) 0.049(4) 0.004(3) 0.020(3) 0.006(3) C12 0.080(4) 0.051(3) 0.059(4) -0.004(3) 0.019(3) -0.010(3) C13 0.058(3) 0.053(3) 0.046(3) -0.006(3) 0.012(3) 0.000(3) C14 0.098(4) 0.072(4) 0.053(4) -0.007(3) -0.009(3) -0.009(3) C15 0.062(4) 0.086(4) 0.068(4) -0.004(3) 0.002(3) -0.016(3) C16 0.164(7) 0.070(4) 0.079(5) 0.012(4) 0.027(5) 0.000(4) C17 0.057(3) 0.042(3) 0.045(3) 0.004(2) -0.005(2) -0.006(3) C18 0.088(4) 0.054(3) 0.072(4) 0.012(3) 0.014(3) -0.002(3) C19 0.048(3) 0.043(3) 0.048(3) 0.006(2) 0.003(2) -0.003(2) C20 0.058(3) 0.044(3) 0.049(3) 0.003(2) 0.005(3) -0.004(2) C21 0.087(4) 0.060(4) 0.057(4) 0.000(3) 0.011(3) -0.003(3) C22 0.069(4) 0.073(4) 0.085(5) 0.007(4) 0.020(4) 0.008(3) C23 0.051(3) 0.069(4) 0.089(5) 0.013(3) 0.008(3) -0.004(3) C24 0.055(3) 0.055(3) 0.061(4) 0.013(3) -0.001(3) -0.006(3) C25 0.072(4) 0.083(4) 0.053(3) -0.005(3) -0.008(3) -0.012(3) C26 0.069(4) 0.090(4) 0.087(5) -0.009(4) -0.013(3) -0.022(3) C27 0.104(5) 0.126(6) 0.130(7) -0.009(5) 0.060(5) 0.022(4) C28 0.176(8) 0.156(8) 0.100(6) 0.006(6) 0.024(6) 0.069(7) Cl3 0.195(3) 0.203(3) 0.161(2) -0.021(2) -0.023(2) -0.013(2) Cl4 0.180(2) 0.154(2) 0.177(3) 0.0365(19) -0.028(2) -0.0166(18) C29 0.216(10) 0.088(5) 0.069(5) 0.015(4) 0.025(6) 0.023(6) Cl5 0.0881(14) 0.180(2) 0.207(3) 0.057(2) 0.0327(16) -0.0165(14) Cl6 0.0973(13) 0.0971(13) 0.1293(16) 0.0040(12) -0.0334(12) 0.0072(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.042(4) . ? Co1 N3 2.228(4) . ? Co1 Cl1 2.2586(15) . ? Co1 N2 2.263(4) . ? Co1 Cl2 2.2762(14) . ? N1 C1 1.344(6) . ? N1 C5 1.355(5) . ? N2 C6 1.280(5) . ? N2 C8 1.443(6) . ? N3 C17 1.289(5) . ? N3 C19 1.450(6) . ? C1 C2 1.380(6) . ? C1 C6 1.499(6) . ? C2 C3 1.384(6) . ? C2 H2 0.9300 . ? C3 C4 1.363(7) . ? C3 H3 0.9300 . ? C4 C5 1.396(6) . ? C4 H4 0.9300 . ? C5 C17 1.480(6) . ? C6 C7 1.488(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C13 1.390(6) . ? C8 C9 1.390(6) . ? C9 C10 1.400(7) . ? C9 C14 1.505(6) . ? C10 C11 1.376(7) . ? C10 H10 0.9300 . ? C11 C12 1.374(7) . ? C11 C16 1.515(7) . ? C12 C13 1.399(7) . ? C12 H12 0.9300 . ? C13 C15 1.509(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.486(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.389(6) . ? C19 C20 1.390(6) . ? C20 C21 1.388(7) . ? C20 C25 1.496(7) . ? C21 C22 1.387(8) . ? C21 H21 0.9300 . ? C22 C23 1.373(8) . ? C22 C27 1.526(8) . ? C23 C24 1.386(7) . ? C23 H23 0.9300 . ? C24 C26 1.504(7) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 Cl4 1.679(9) . ? C28 Cl3 1.702(9) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 Cl6 1.734(8) . ? C29 Cl5 1.743(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N3 75.70(16) . . ? N1 Co1 Cl1 119.76(11) . . ? N3 Co1 Cl1 96.89(10) . . ? N1 Co1 N2 74.59(15) . . ? N3 Co1 N2 150.19(14) . . ? Cl1 Co1 N2 99.79(10) . . ? N1 Co1 Cl2 123.88(10) . . ? N3 Co1 Cl2 99.20(10) . . ? Cl1 Co1 Cl2 116.34(6) . . ? N2 Co1 Cl2 95.29(10) . . ? C1 N1 C5 120.8(4) . . ? C1 N1 Co1 120.7(3) . . ? C5 N1 Co1 118.5(3) . . ? C6 N2 C8 119.3(4) . . ? C6 N2 Co1 114.4(3) . . ? C8 N2 Co1 126.2(3) . . ? C17 N3 C19 119.4(4) . . ? C17 N3 Co1 114.3(3) . . ? C19 N3 Co1 126.2(3) . . ? N1 C1 C2 121.0(5) . . ? N1 C1 C6 114.1(4) . . ? C2 C1 C6 124.8(5) . . ? C1 C2 C3 118.5(5) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.0(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 119.9(5) . . ? N1 C5 C17 115.4(4) . . ? C4 C5 C17 124.7(5) . . ? N2 C6 C7 125.9(5) . . ? N2 C6 C1 116.1(4) . . ? C7 C6 C1 118.0(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 121.9(5) . . ? C13 C8 N2 119.2(4) . . ? C9 C8 N2 118.8(4) . . ? C8 C9 C10 117.7(5) . . ? C8 C9 C14 122.5(5) . . ? C10 C9 C14 119.7(5) . . ? C11 C10 C9 122.1(5) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C12 C11 C10 118.2(5) . . ? C12 C11 C16 120.8(5) . . ? C10 C11 C16 120.9(6) . . ? C11 C12 C13 122.6(5) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C8 C13 C12 117.4(5) . . ? C8 C13 C15 122.1(5) . . ? C12 C13 C15 120.5(5) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 C5 115.7(4) . . ? N3 C17 C18 125.5(5) . . ? C5 C17 C18 118.7(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 121.9(5) . . ? C24 C19 N3 117.9(4) . . ? C20 C19 N3 120.2(4) . . ? C21 C20 C19 117.2(5) . . ? C21 C20 C25 119.8(5) . . ? C19 C20 C25 122.9(5) . . ? C22 C21 C20 123.0(5) . . ? C22 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C23 C22 C21 117.2(5) . . ? C23 C22 C27 120.7(6) . . ? C21 C22 C27 122.1(6) . . ? C22 C23 C24 122.8(5) . . ? C22 C23 H23 118.6 . . ? C24 C23 H23 118.6 . . ? C19 C24 C23 117.8(5) . . ? C19 C24 C26 121.7(5) . . ? C23 C24 C26 120.5(5) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Cl4 C28 Cl3 115.8(5) . . ? Cl4 C28 H28A 108.3 . . ? Cl3 C28 H28A 108.3 . . ? Cl4 C28 H28B 108.3 . . ? Cl3 C28 H28B 108.3 . . ? H28A C28 H28B 107.4 . . ? Cl6 C29 Cl5 110.1(4) . . ? Cl6 C29 H29A 109.6 . . ? Cl5 C29 H29A 109.6 . . ? Cl6 C29 H29B 109.6 . . ? Cl5 C29 H29B 109.6 . . ? H29A C29 H29B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 872215' ####################################################################### # # 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_v201 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26.17 H27.33 Cl6.33 Co N3' _chemical_formula_weight 667.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 24.8916(7) _cell_length_b 24.8916(7) _cell_length_c 25.6814(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13780.2(8) _cell_formula_units_Z 18 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4918 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 22.49 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6120 _exptl_absorpt_coefficient_mu 1.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7419 _exptl_absorpt_correction_T_max 0.9048 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23065 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4852 _reflns_number_gt 4161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The dichloromethane solvent molecules were refined with restraints of C---Cl = 1.78(1) \%A. 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^)+(0.1032P)^2^+6.3433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 4852 _refine_ls_number_parameters 343 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.003 _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 0.74963(3) 0.00130(4) 0.95136(3) 0.0305(2) Uani 1 1 d . . . Cl1 Cl 0.67760(9) -0.20529(7) 1.00026(7) 0.0482(4) Uani 1 1 d . . . Cl2 Cl 0.69052(11) 0.10053(8) 1.08006(8) 0.0575(5) Uani 1 1 d . . . Cl3 Cl 0.68598(7) -0.00855(7) 0.88546(6) 0.0397(4) Uani 1 1 d . . . Cl4 Cl 0.85276(7) 0.05376(7) 0.94509(8) 0.0461(4) Uani 1 1 d . . . N1 N 0.7337(2) -0.0982(2) 0.94965(18) 0.0302(10) Uani 1 1 d . . . N2 N 0.7420(2) 0.0820(2) 0.99654(18) 0.0265(9) Uani 1 1 d . . . N3 N 0.6984(2) -0.0390(2) 1.01618(18) 0.0270(9) Uani 1 1 d . . . C1 C 0.6768(3) -0.1001(2) 1.0248(2) 0.0289(11) Uani 1 1 d . . . C2 C 0.6344(3) -0.1327(3) 1.0644(2) 0.0345(13) Uani 1 1 d . . . H2 H 0.6189 -0.1759 1.0692 0.041 Uiso 1 1 calc R . . C3 C 0.6155(3) -0.1002(3) 1.0966(3) 0.0367(13) Uani 1 1 d . . . H3 H 0.5864 -0.1213 1.1237 0.044 Uiso 1 1 calc R . . C4 C 0.6390(3) -0.0374(3) 1.0893(2) 0.0343(13) Uani 1 1 d . . . H4 H 0.6272 -0.0147 1.1117 0.041 Uiso 1 1 calc R . . C5 C 0.6806(3) -0.0077(3) 1.0481(2) 0.0290(11) Uani 1 1 d . . . C6 C 0.7004(3) -0.1286(3) 0.9873(2) 0.0305(12) Uani 1 1 d . . . C7 C 0.7544(3) -0.1269(2) 0.9115(2) 0.0306(12) Uani 1 1 d . . . C8 C 0.7132(3) -0.1601(3) 0.8701(2) 0.0343(13) Uani 1 1 d . . . C9 C 0.7354(3) -0.1836(3) 0.8312(2) 0.0385(14) Uani 1 1 d . . . H9 H 0.7091 -0.2051 0.8026 0.046 Uiso 1 1 calc R . . C10 C 0.7945(3) -0.1763(3) 0.8331(2) 0.0355(13) Uani 1 1 d . . . C11 C 0.8305(3) -0.1454(3) 0.8753(3) 0.0389(14) Uani 1 1 d . . . H11 H 0.8705 -0.1411 0.8774 0.047 Uiso 1 1 calc R . . C12 C 0.8129(3) -0.1202(3) 0.9150(2) 0.0334(12) Uani 1 1 d . . . C13 C 0.6482(3) -0.1712(3) 0.8676(3) 0.0414(14) Uani 1 1 d . . . H13A H 0.6278 -0.1951 0.8362 0.062 Uiso 1 1 calc R . . H13B H 0.6493 -0.1314 0.8664 0.062 Uiso 1 1 calc R . . H13C H 0.6251 -0.1945 0.8984 0.062 Uiso 1 1 calc R . . C14 C 0.8168(4) -0.2007(3) 0.7906(3) 0.0486(16) Uani 1 1 d . . . H14A H 0.8455 -0.1664 0.7682 0.073 Uiso 1 1 calc R . . H14B H 0.7814 -0.2309 0.7700 0.073 Uiso 1 1 calc R . . H14C H 0.8383 -0.2210 0.8056 0.073 Uiso 1 1 calc R . . C15 C 0.8546(3) -0.0885(3) 0.9600(3) 0.0483(17) Uani 1 1 d . . . H15A H 0.8568 -0.0486 0.9662 0.072 Uiso 1 1 calc R . . H15B H 0.8962 -0.0815 0.9524 0.072 Uiso 1 1 calc R . . H15C H 0.8383 -0.1145 0.9911 0.072 Uiso 1 1 calc R . . C16 C 0.7080(2) 0.0579(3) 1.0364(2) 0.0304(12) Uani 1 1 d . . . C17 C 0.7700(2) 0.1464(3) 0.9873(2) 0.0296(11) Uani 1 1 d . . . C18 C 0.8271(3) 0.1871(3) 1.0120(2) 0.0352(13) Uani 1 1 d . . . C19 C 0.8542(3) 0.2501(3) 1.0020(3) 0.0384(14) Uani 1 1 d . . . H19 H 0.8923 0.2777 1.0186 0.046 Uiso 1 1 calc R . . C20 C 0.8282(3) 0.2740(3) 0.9690(3) 0.0459(16) Uani 1 1 d . . . C21 C 0.7711(3) 0.2340(3) 0.9468(3) 0.0425(15) Uani 1 1 d . . . H21 H 0.7521 0.2508 0.9252 0.051 Uiso 1 1 calc R . . C22 C 0.7401(3) 0.1697(3) 0.9550(2) 0.0350(13) Uani 1 1 d . . . C23 C 0.8570(3) 0.1611(3) 1.0468(3) 0.0468(16) Uani 1 1 d . . . H23A H 0.8941 0.1952 1.0629 0.070 Uiso 1 1 calc R . . H23B H 0.8688 0.1355 1.0261 0.070 Uiso 1 1 calc R . . H23C H 0.8277 0.1356 1.0740 0.070 Uiso 1 1 calc R . . C24 C 0.8615(4) 0.3443(3) 0.9589(4) 0.063(2) Uani 1 1 d . . . H24A H 0.8459 0.3638 0.9831 0.094 Uiso 1 1 calc R . . H24B H 0.8536 0.3520 0.9230 0.094 Uiso 1 1 calc R . . H24C H 0.9062 0.3620 0.9640 0.094 Uiso 1 1 calc R . . C25 C 0.6773(3) 0.1282(3) 0.9327(3) 0.0400(14) Uani 1 1 d . . . H25A H 0.6468 0.1107 0.9610 0.060 Uiso 1 1 calc R . . H25B H 0.6777 0.0944 0.9134 0.060 Uiso 1 1 calc R . . H25C H 0.6661 0.1520 0.9092 0.060 Uiso 1 1 calc R . . Cl5 Cl 0.86963(16) 0.00380(17) 0.81499(15) 0.1124(11) Uani 1 1 d D . . Cl6 Cl 0.91284(18) 0.02299(17) 0.71006(18) 0.1280(13) Uani 1 1 d D . . C26 C 0.8798(6) -0.0306(5) 0.7596(4) 0.120(5) Uani 1 1 d D . . H26A H 0.9068 -0.0481 0.7681 0.144 Uiso 1 1 calc R . . H26B H 0.8391 -0.0651 0.7480 0.144 Uiso 1 1 calc R . . Cl7 Cl 0.7424(4) 0.3673(3) 0.8961(3) 0.081(2) Uani 0.33 1 d PD . . C27 C 0.6667 0.3333 0.9249(11) 0.131(18) Uani 0.50 3 d SPD . . 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 0.0320(4) 0.0323(4) 0.0248(4) 0.0041(3) 0.0027(3) 0.0144(3) Cl1 0.0810(12) 0.0270(7) 0.0386(9) 0.0066(6) 0.0161(8) 0.0285(8) Cl2 0.0858(13) 0.0435(9) 0.0528(11) 0.0014(8) 0.0295(10) 0.0394(9) Cl3 0.0479(8) 0.0335(7) 0.0330(8) 0.0004(6) -0.0103(6) 0.0168(6) Cl4 0.0340(8) 0.0351(8) 0.0690(11) 0.0096(7) 0.0107(7) 0.0172(6) N1 0.041(3) 0.030(2) 0.022(2) -0.0030(18) -0.001(2) 0.020(2) N2 0.023(2) 0.029(2) 0.029(2) -0.0049(19) -0.0066(18) 0.0145(19) N3 0.026(2) 0.027(2) 0.026(2) -0.0020(18) 0.0003(18) 0.0122(19) C1 0.029(3) 0.027(3) 0.028(3) 0.003(2) -0.002(2) 0.012(2) C2 0.036(3) 0.036(3) 0.028(3) 0.004(2) -0.001(2) 0.015(3) C3 0.033(3) 0.041(3) 0.035(3) 0.007(3) 0.008(2) 0.018(3) C4 0.036(3) 0.041(3) 0.028(3) 0.002(3) 0.006(2) 0.021(3) C5 0.030(3) 0.034(3) 0.027(3) -0.005(2) -0.003(2) 0.019(2) C6 0.035(3) 0.026(3) 0.030(3) -0.002(2) -0.007(2) 0.015(2) C7 0.047(3) 0.022(3) 0.025(3) 0.005(2) 0.007(2) 0.019(3) C8 0.045(3) 0.033(3) 0.023(3) 0.000(2) 0.001(2) 0.018(3) C9 0.056(4) 0.034(3) 0.024(3) -0.004(2) -0.003(3) 0.022(3) C10 0.045(4) 0.037(3) 0.029(3) 0.003(2) 0.005(3) 0.024(3) C11 0.041(3) 0.038(3) 0.045(4) 0.006(3) 0.006(3) 0.025(3) C12 0.046(3) 0.026(3) 0.030(3) 0.007(2) -0.002(3) 0.020(3) C13 0.046(3) 0.042(3) 0.037(4) -0.008(3) -0.008(3) 0.022(3) C14 0.060(4) 0.058(4) 0.039(4) -0.004(3) 0.007(3) 0.038(4) C15 0.055(4) 0.045(4) 0.050(4) -0.010(3) -0.016(3) 0.028(3) C16 0.031(3) 0.035(3) 0.030(3) -0.008(2) -0.003(2) 0.020(2) C17 0.028(3) 0.032(3) 0.027(3) -0.004(2) 0.000(2) 0.013(2) C18 0.031(3) 0.037(3) 0.034(3) -0.011(2) 0.001(2) 0.015(3) C19 0.032(3) 0.035(3) 0.041(4) -0.017(3) 0.003(3) 0.011(3) C20 0.043(4) 0.031(3) 0.052(4) -0.012(3) 0.012(3) 0.010(3) C21 0.054(4) 0.038(3) 0.039(4) 0.001(3) -0.003(3) 0.025(3) C22 0.041(3) 0.032(3) 0.034(3) -0.002(2) -0.002(2) 0.019(3) C23 0.042(4) 0.056(4) 0.045(4) -0.013(3) -0.014(3) 0.026(3) C24 0.072(5) 0.022(3) 0.078(6) -0.005(3) 0.012(4) 0.010(3) C25 0.037(3) 0.037(3) 0.045(4) 0.001(3) -0.007(3) 0.018(3) Cl5 0.114(2) 0.103(2) 0.109(3) 0.0140(18) -0.0186(19) 0.0452(19) Cl6 0.113(3) 0.108(3) 0.141(3) -0.012(2) -0.005(2) 0.039(2) C26 0.110(9) 0.122(10) 0.171(16) 0.025(10) 0.033(9) 0.090(9) Cl7 0.104(5) 0.056(4) 0.098(5) 0.013(4) 0.001(4) 0.052(4) C27 0.16(3) 0.16(3) 0.07(3) 0.000 0.000 0.081(14) _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 N3 2.031(5) . ? Co1 Cl4 2.2290(17) . ? Co1 Cl3 2.2463(17) . ? Co1 N1 2.305(5) . ? Co1 N2 2.408(4) . ? Cl1 C6 1.729(6) . ? Cl2 C16 1.741(6) . ? N1 C6 1.253(8) . ? N1 C7 1.450(7) . ? N2 C16 1.273(7) . ? N2 C17 1.413(7) . ? N3 C5 1.348(7) . ? N3 C1 1.354(7) . ? C1 C2 1.396(8) . ? C1 C6 1.482(8) . ? C2 C3 1.393(9) . ? C2 H2 0.9500 . ? C3 C4 1.381(9) . ? C3 H3 0.9500 . ? C4 C5 1.404(8) . ? C4 H4 0.9500 . ? C5 C16 1.452(8) . ? C7 C12 1.384(8) . ? C7 C8 1.419(8) . ? C8 C9 1.403(8) . ? C8 C13 1.500(9) . ? C9 C10 1.391(9) . ? C9 H9 0.9500 . ? C10 C11 1.371(10) . ? C10 C14 1.485(9) . ? C11 C12 1.378(9) . ? C11 H11 0.9500 . ? C12 C15 1.488(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C22 1.417(8) . ? C17 C18 1.417(8) . ? C18 C19 1.385(9) . ? C18 C23 1.502(9) . ? C19 C20 1.371(11) . ? C19 H19 0.9500 . ? C20 C21 1.385(10) . ? C20 C24 1.538(9) . ? C21 C22 1.404(9) . ? C21 H21 0.9500 . ? C22 C25 1.491(9) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Cl5 C26 1.743(9) . ? Cl6 C26 1.727(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? Cl7 C27 1.795(10) . ? C27 Cl7 1.795(9) 3_665 ? C27 Cl7 1.796(9) 2_655 ? 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 N3 Co1 Cl4 127.13(14) . . ? N3 Co1 Cl3 109.19(14) . . ? Cl4 Co1 Cl3 123.53(8) . . ? N3 Co1 N1 75.96(18) . . ? Cl4 Co1 N1 99.02(13) . . ? Cl3 Co1 N1 97.79(13) . . ? N3 Co1 N2 74.02(17) . . ? Cl4 Co1 N2 95.40(12) . . ? Cl3 Co1 N2 96.23(11) . . ? N1 Co1 N2 149.63(16) . . ? C6 N1 C7 121.0(5) . . ? C6 N1 Co1 109.9(4) . . ? C7 N1 Co1 129.0(4) . . ? C16 N2 C17 120.3(5) . . ? C16 N2 Co1 107.8(4) . . ? C17 N2 Co1 131.8(4) . . ? C5 N3 C1 119.2(5) . . ? C5 N3 Co1 121.4(4) . . ? C1 N3 Co1 119.2(4) . . ? N3 C1 C2 122.3(5) . . ? N3 C1 C6 113.8(5) . . ? C2 C1 C6 124.0(5) . . ? C1 C2 C3 118.0(6) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.1(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N3 C5 C4 121.5(5) . . ? N3 C5 C16 114.8(5) . . ? C4 C5 C16 123.7(5) . . ? N1 C6 C1 120.9(5) . . ? N1 C6 Cl1 124.6(5) . . ? C1 C6 Cl1 114.5(4) . . ? C12 C7 C8 122.0(5) . . ? C12 C7 N1 120.5(5) . . ? C8 C7 N1 117.5(5) . . ? C9 C8 C7 117.1(6) . . ? C9 C8 C13 120.2(6) . . ? C7 C8 C13 122.6(5) . . ? C10 C9 C8 122.1(6) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C9 116.9(5) . . ? C11 C10 C14 122.5(6) . . ? C9 C10 C14 120.6(6) . . ? C10 C11 C12 125.0(6) . . ? C10 C11 H11 117.5 . . ? C12 C11 H11 117.5 . . ? C7 C12 C11 116.8(6) . . ? C7 C12 C15 121.9(6) . . ? C11 C12 C15 121.3(6) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C5 121.6(5) . . ? N2 C16 Cl2 122.7(4) . . ? C5 C16 Cl2 115.7(4) . . ? C22 C17 N2 120.0(5) . . ? C22 C17 C18 121.0(5) . . ? N2 C17 C18 119.0(5) . . ? C19 C18 C17 118.1(6) . . ? C19 C18 C23 122.2(6) . . ? C17 C18 C23 119.6(6) . . ? C20 C19 C18 122.6(6) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C21 118.7(6) . . ? C19 C20 C24 119.7(7) . . ? C21 C20 C24 121.6(7) . . ? C20 C21 C22 122.6(6) . . ? C20 C21 H21 118.7 . . ? C22 C21 H21 118.7 . . ? C21 C22 C17 116.9(6) . . ? C21 C22 C25 121.4(6) . . ? C17 C22 C25 121.7(5) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Cl6 C26 Cl5 110.6(6) . . ? Cl6 C26 H26A 109.5 . . ? Cl5 C26 H26A 109.5 . . ? Cl6 C26 H26B 109.5 . . ? Cl5 C26 H26B 109.5 . . ? H26A C26 H26B 108.1 . . ? Cl7 C27 Cl7 104.2(10) 3_665 . ? Cl7 C27 Cl7 104.2(10) 3_665 2_655 ? Cl7 C27 Cl7 104.2(10) . 2_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.628 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 903515' ####################################################################### # # 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_v248 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H37 Cl4 Co N3' _chemical_formula_weight 652.37 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' 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' _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 8.8292(5) _cell_length_b 9.7126(5) _cell_length_c 21.0607(12) _cell_angle_alpha 82.7520(10) _cell_angle_beta 87.6250(10) _cell_angle_gamma 65.7340(10) _cell_volume 1633.22(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3409 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.91 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 678 _exptl_absorpt_coefficient_mu 0.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7977 _exptl_absorpt_correction_T_max 0.8945 _exptl_absorpt_process_details SADABS _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 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8633 _diffrn_reflns_av_R_equivalents 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5983 _reflns_number_gt 4757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.1958P] 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 5983 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.44343(4) 0.67132(3) 0.268609(15) 0.03667(11) Uani 1 1 d . . . Cl1 Cl 0.40016(10) 0.90850(7) 0.23050(4) 0.0624(2) Uani 1 1 d . . . Cl2 Cl 0.67828(8) 0.52270(8) 0.32497(3) 0.0603(2) Uani 1 1 d . . . Cl3 Cl 0.53680(11) 0.33533(8) 0.11709(3) 0.0668(2) Uani 1 1 d . . . Cl4 Cl 0.09037(10) 0.60513(8) 0.43100(4) 0.0654(2) Uani 1 1 d . . . N1 N 0.3560(2) 0.50258(19) 0.27670(9) 0.0335(4) Uani 1 1 d . . . N2 N 0.5026(2) 0.5719(2) 0.17527(9) 0.0359(4) Uani 1 1 d . . . N3 N 0.2496(2) 0.7248(2) 0.34746(9) 0.0359(4) Uani 1 1 d . . . C1 C 0.4108(3) 0.3978(2) 0.23562(11) 0.0362(5) Uani 1 1 d . . . C2 C 0.3893(3) 0.2635(3) 0.24704(12) 0.0443(6) Uani 1 1 d . . . H2 H 0.4290 0.1911 0.2185 0.053 Uiso 1 1 calc R . . C3 C 0.3074(3) 0.2396(3) 0.30193(13) 0.0510(7) Uani 1 1 d . . . H3 H 0.2935 0.1494 0.3112 0.061 Uiso 1 1 calc R . . C4 C 0.2464(3) 0.3502(3) 0.34301(13) 0.0493(6) Uani 1 1 d . . . H4 H 0.1882 0.3371 0.3794 0.059 Uiso 1 1 calc R . . C5 C 0.2739(3) 0.4807(2) 0.32858(11) 0.0373(5) Uani 1 1 d . . . C6 C 0.4868(3) 0.4481(3) 0.17839(11) 0.0372(5) Uani 1 1 d . . . C7 C 0.5566(3) 0.6365(3) 0.11762(11) 0.0381(5) Uani 1 1 d . . . C8 C 0.7250(3) 0.6002(3) 0.10811(13) 0.0498(6) Uani 1 1 d . . . C9 C 0.7680(4) 0.6668(4) 0.05171(14) 0.0624(8) Uani 1 1 d . . . H9 H 0.8796 0.6419 0.0429 0.075 Uiso 1 1 calc R . . C10 C 0.6491(4) 0.7685(4) 0.00878(14) 0.0609(8) Uani 1 1 d . . . H10 H 0.6809 0.8127 -0.0281 0.073 Uiso 1 1 calc R . . C11 C 0.4844(4) 0.8046(3) 0.02019(12) 0.0532(7) Uani 1 1 d . . . H11 H 0.4051 0.8741 -0.0089 0.064 Uiso 1 1 calc R . . C12 C 0.4336(3) 0.7383(3) 0.07515(12) 0.0451(6) Uani 1 1 d . . . C13 C 0.8586(3) 0.4979(4) 0.15678(15) 0.0626(8) Uani 1 1 d . . . H13 H 0.8080 0.4487 0.1892 0.075 Uiso 1 1 calc R . . C14 C 0.9247(4) 0.5942(5) 0.19034(17) 0.0886(11) Uani 1 1 d . . . H14A H 0.9848 0.6350 0.1602 0.133 Uiso 1 1 calc R . . H14B H 0.9975 0.5316 0.2250 0.133 Uiso 1 1 calc R . . H14C H 0.8332 0.6761 0.2067 0.133 Uiso 1 1 calc R . . C15 C 1.0003(4) 0.3737(4) 0.12601(19) 0.0909(11) Uani 1 1 d . . . H15A H 0.9571 0.3138 0.1059 0.136 Uiso 1 1 calc R . . H15B H 1.0805 0.3097 0.1583 0.136 Uiso 1 1 calc R . . H15C H 1.0525 0.4196 0.0944 0.136 Uiso 1 1 calc R . . C16 C 0.2504(3) 0.7769(4) 0.08437(14) 0.0628(8) Uani 1 1 d . . . H16 H 0.2371 0.7279 0.1266 0.075 Uiso 1 1 calc R . . C17 C 0.1861(5) 0.7134(5) 0.0346(2) 0.0951(12) Uani 1 1 d . . . H17A H 0.1944 0.7620 -0.0072 0.143 Uiso 1 1 calc R . . H17B H 0.0720 0.7323 0.0431 0.143 Uiso 1 1 calc R . . H17C H 0.2512 0.6058 0.0364 0.143 Uiso 1 1 calc R . . C18 C 0.1474(4) 0.9483(4) 0.0830(2) 0.0952(12) Uani 1 1 d . . . H18A H 0.1962 0.9883 0.1118 0.143 Uiso 1 1 calc R . . H18B H 0.0360 0.9665 0.0961 0.143 Uiso 1 1 calc R . . H18C H 0.1455 0.9975 0.0404 0.143 Uiso 1 1 calc R . . C19 C 0.2137(3) 0.6136(3) 0.36567(11) 0.0383(5) Uani 1 1 d . . . C20 C 0.1826(3) 0.8634(2) 0.37809(11) 0.0374(5) Uani 1 1 d . . . C21 C 0.2668(3) 0.8753(3) 0.42992(12) 0.0439(6) Uani 1 1 d . . . C22 C 0.1957(4) 1.0118(3) 0.45704(14) 0.0541(7) Uani 1 1 d . . . H22 H 0.2464 1.0238 0.4925 0.065 Uiso 1 1 calc R . . C23 C 0.0526(4) 1.1284(3) 0.43223(15) 0.0593(8) Uani 1 1 d . . . H23 H 0.0073 1.2179 0.4512 0.071 Uiso 1 1 calc R . . C24 C -0.0241(3) 1.1145(3) 0.38001(15) 0.0559(7) Uani 1 1 d . . . H24 H -0.1201 1.1955 0.3636 0.067 Uiso 1 1 calc R . . C25 C 0.0387(3) 0.9810(3) 0.35074(12) 0.0462(6) Uani 1 1 d . . . C26 C 0.4296(3) 0.7511(3) 0.45592(13) 0.0548(7) Uani 1 1 d . . . H26 H 0.4526 0.6631 0.4329 0.066 Uiso 1 1 calc R . . C27 C 0.4208(5) 0.6997(5) 0.52682(16) 0.0942(12) Uani 1 1 d . . . H27A H 0.3976 0.7837 0.5508 0.141 Uiso 1 1 calc R . . H27B H 0.5252 0.6190 0.5409 0.141 Uiso 1 1 calc R . . H27C H 0.3342 0.6640 0.5335 0.141 Uiso 1 1 calc R . . C28 C 0.5705(4) 0.8016(5) 0.4418(2) 0.0993(13) Uani 1 1 d . . . H28A H 0.5680 0.8385 0.3972 0.149 Uiso 1 1 calc R . . H28B H 0.6748 0.7168 0.4522 0.149 Uiso 1 1 calc R . . H28C H 0.5578 0.8812 0.4671 0.149 Uiso 1 1 calc R . . C29 C -0.0483(4) 0.9659(3) 0.29355(15) 0.0634(8) Uani 1 1 d . . . H29 H 0.0282 0.8766 0.2742 0.076 Uiso 1 1 calc R . . C30 C -0.2017(5) 0.9397(5) 0.3138(2) 0.1105(15) Uani 1 1 d . . . H30A H -0.1717 0.8530 0.3458 0.166 Uiso 1 1 calc R . . H30B H -0.2497 0.9216 0.2774 0.166 Uiso 1 1 calc R . . H30C H -0.2810 1.0279 0.3311 0.166 Uiso 1 1 calc R . . C31 C -0.0942(5) 1.1028(4) 0.24305(18) 0.0982(13) Uani 1 1 d . . . H31A H -0.1800 1.1894 0.2590 0.147 Uiso 1 1 calc R . . H31B H -0.1334 1.0818 0.2051 0.147 Uiso 1 1 calc R . . H31C H 0.0019 1.1238 0.2330 0.147 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.04188(19) 0.03013(17) 0.04154(19) -0.00809(13) 0.00370(13) -0.01752(14) Cl1 0.0951(5) 0.0353(3) 0.0637(4) -0.0099(3) 0.0144(4) -0.0336(4) Cl2 0.0493(4) 0.0629(4) 0.0560(4) -0.0088(3) -0.0053(3) -0.0092(3) Cl3 0.1063(6) 0.0597(4) 0.0519(4) -0.0318(3) 0.0272(4) -0.0468(4) Cl4 0.0870(5) 0.0602(4) 0.0615(4) -0.0232(4) 0.0403(4) -0.0419(4) N1 0.0396(10) 0.0295(9) 0.0344(10) -0.0092(8) 0.0056(8) -0.0160(8) N2 0.0366(10) 0.0353(10) 0.0376(10) -0.0084(8) 0.0046(8) -0.0156(8) N3 0.0385(10) 0.0292(9) 0.0398(11) -0.0092(8) 0.0033(8) -0.0125(8) C1 0.0386(12) 0.0320(11) 0.0398(13) -0.0071(10) 0.0002(10) -0.0154(10) C2 0.0543(15) 0.0333(12) 0.0485(14) -0.0139(11) 0.0058(12) -0.0192(11) C3 0.0712(18) 0.0352(13) 0.0566(16) -0.0097(12) 0.0102(13) -0.0315(13) C4 0.0655(17) 0.0437(14) 0.0480(15) -0.0089(11) 0.0135(13) -0.0321(13) C5 0.0434(13) 0.0349(12) 0.0370(12) -0.0071(10) 0.0028(10) -0.0189(10) C6 0.0419(13) 0.0358(12) 0.0360(12) -0.0137(10) 0.0054(10) -0.0158(10) C7 0.0460(13) 0.0403(12) 0.0360(12) -0.0119(10) 0.0080(10) -0.0243(11) C8 0.0511(15) 0.0581(16) 0.0488(15) -0.0108(12) 0.0069(12) -0.0305(13) C9 0.0575(17) 0.088(2) 0.0596(18) -0.0087(16) 0.0124(14) -0.0484(17) C10 0.076(2) 0.0734(19) 0.0482(16) -0.0029(14) 0.0120(15) -0.0484(17) C11 0.0687(18) 0.0535(16) 0.0402(14) -0.0015(12) 0.0015(13) -0.0292(14) C12 0.0525(15) 0.0453(14) 0.0401(14) -0.0074(11) 0.0050(11) -0.0225(12) C13 0.0464(16) 0.079(2) 0.0640(19) -0.0044(16) 0.0045(13) -0.0289(15) C14 0.075(2) 0.124(3) 0.076(2) -0.013(2) -0.0111(18) -0.049(2) C15 0.062(2) 0.092(3) 0.100(3) -0.010(2) 0.0061(19) -0.0135(19) C16 0.0492(16) 0.075(2) 0.0537(17) 0.0118(15) 0.0015(13) -0.0202(15) C17 0.073(2) 0.109(3) 0.123(3) -0.004(3) -0.011(2) -0.059(2) C18 0.063(2) 0.093(3) 0.099(3) -0.019(2) -0.0069(19) 0.0022(19) C19 0.0407(13) 0.0393(12) 0.0364(12) -0.0091(10) 0.0081(10) -0.0175(11) C20 0.0429(13) 0.0298(11) 0.0419(13) -0.0126(10) 0.0127(10) -0.0162(10) C21 0.0486(14) 0.0418(13) 0.0472(14) -0.0135(11) 0.0137(11) -0.0233(11) C22 0.0652(18) 0.0536(16) 0.0575(17) -0.0266(13) 0.0155(14) -0.0340(15) C23 0.0693(19) 0.0418(15) 0.072(2) -0.0275(14) 0.0303(16) -0.0253(14) C24 0.0557(16) 0.0352(13) 0.0669(19) -0.0067(13) 0.0188(14) -0.0100(12) C25 0.0486(14) 0.0363(13) 0.0506(15) -0.0063(11) 0.0115(12) -0.0150(11) C26 0.0496(15) 0.0632(17) 0.0546(16) -0.0242(14) 0.0037(12) -0.0216(13) C27 0.085(3) 0.103(3) 0.061(2) -0.009(2) -0.0080(18) -0.004(2) C28 0.059(2) 0.109(3) 0.147(4) -0.047(3) 0.012(2) -0.043(2) C29 0.0544(17) 0.0518(16) 0.0672(19) -0.0101(14) -0.0053(14) -0.0036(14) C30 0.100(3) 0.134(4) 0.115(3) 0.011(3) -0.031(3) -0.070(3) C31 0.097(3) 0.102(3) 0.069(2) 0.017(2) -0.011(2) -0.021(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.0664(17) . ? Co1 Cl1 2.2209(7) . ? Co1 N2 2.2467(18) . ? Co1 Cl2 2.2592(7) . ? Co1 N3 2.2818(18) . ? Cl3 C6 1.724(2) . ? Cl4 C19 1.734(2) . ? N1 C5 1.329(3) . ? N1 C1 1.342(3) . ? N2 C6 1.261(3) . ? N2 C7 1.449(3) . ? N3 C19 1.257(3) . ? N3 C20 1.453(3) . ? C1 C2 1.384(3) . ? C1 C6 1.482(3) . ? C2 C3 1.383(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 H4 0.9300 . ? C5 C19 1.488(3) . ? C7 C12 1.390(3) . ? C7 C8 1.392(3) . ? C8 C9 1.394(4) . ? C8 C13 1.519(4) . ? C9 C10 1.377(4) . ? C9 H9 0.9300 . ? C10 C11 1.366(4) . ? C10 H10 0.9300 . ? C11 C12 1.401(3) . ? C11 H11 0.9300 . ? C12 C16 1.513(4) . ? C13 C15 1.526(4) . ? C13 C14 1.538(4) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.517(5) . ? C16 C18 1.532(5) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 C21 1.388(3) . ? C20 C25 1.397(3) . ? C21 C22 1.399(3) . ? C21 C26 1.515(4) . ? C22 C23 1.372(4) . ? C22 H22 0.9300 . ? C23 C24 1.364(4) . ? C23 H23 0.9300 . ? C24 C25 1.397(4) . ? C24 H24 0.9300 . ? C25 C29 1.508(4) . ? C26 C28 1.521(4) . ? C26 C27 1.523(4) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.513(5) . ? C29 C31 1.516(4) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? 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 Cl1 147.08(6) . . ? N1 Co1 N2 74.38(7) . . ? Cl1 Co1 N2 97.59(5) . . ? N1 Co1 Cl2 93.34(6) . . ? Cl1 Co1 Cl2 119.58(3) . . ? N2 Co1 Cl2 100.43(5) . . ? N1 Co1 N3 73.45(7) . . ? Cl1 Co1 N3 98.21(5) . . ? N2 Co1 N3 141.74(7) . . ? Cl2 Co1 N3 101.58(5) . . ? C5 N1 C1 119.86(19) . . ? C5 N1 Co1 120.14(14) . . ? C1 N1 Co1 118.70(14) . . ? C6 N2 C7 122.22(19) . . ? C6 N2 Co1 111.97(15) . . ? C7 N2 Co1 125.79(14) . . ? C19 N3 C20 122.16(19) . . ? C19 N3 Co1 111.69(14) . . ? C20 N3 Co1 125.97(14) . . ? N1 C1 C2 121.5(2) . . ? N1 C1 C6 111.87(19) . . ? C2 C1 C6 126.6(2) . . ? C1 C2 C3 118.4(2) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.0(2) . . ? N1 C5 C19 111.83(19) . . ? C4 C5 C19 126.1(2) . . ? N2 C6 C1 119.6(2) . . ? N2 C6 Cl3 123.88(18) . . ? C1 C6 Cl3 116.34(16) . . ? C12 C7 C8 123.0(2) . . ? C12 C7 N2 117.1(2) . . ? C8 C7 N2 119.8(2) . . ? C7 C8 C9 116.8(3) . . ? C7 C8 C13 123.1(2) . . ? C9 C8 C13 120.1(2) . . ? C10 C9 C8 121.6(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.9(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 117.5(2) . . ? C7 C12 C16 123.5(2) . . ? C11 C12 C16 119.0(2) . . ? C8 C13 C15 111.8(3) . . ? C8 C13 C14 109.8(3) . . ? C15 C13 C14 110.6(3) . . ? C8 C13 H13 108.2 . . ? C15 C13 H13 108.2 . . ? C14 C13 H13 108.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 110.6(3) . . ? C12 C16 C18 112.2(3) . . ? C17 C16 C18 110.6(3) . . ? C12 C16 H16 107.8 . . ? C17 C16 H16 107.8 . . ? C18 C16 H16 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C5 119.5(2) . . ? N3 C19 Cl4 124.31(18) . . ? C5 C19 Cl4 116.16(16) . . ? C21 C20 C25 123.8(2) . . ? C21 C20 N3 119.4(2) . . ? C25 C20 N3 116.7(2) . . ? C20 C21 C22 116.5(2) . . ? C20 C21 C26 123.2(2) . . ? C22 C21 C26 120.4(2) . . ? C23 C22 C21 121.2(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 121.3(3) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C20 C25 C24 116.4(2) . . ? C20 C25 C29 122.7(2) . . ? C24 C25 C29 120.9(2) . . ? C21 C26 C28 110.2(3) . . ? C21 C26 C27 112.4(2) . . ? C28 C26 C27 111.9(3) . . ? C21 C26 H26 107.3 . . ? C28 C26 H26 107.3 . . ? C27 C26 H26 107.3 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C30 110.8(3) . . ? C25 C29 C31 112.5(3) . . ? C30 C29 C31 110.0(3) . . ? C25 C29 H29 107.8 . . ? C30 C29 H29 107.8 . . ? C31 C29 H29 107.8 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.315 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 903516' ####################################################################### # # 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_v264 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 Cl4 Co N3' _chemical_formula_weight 484.05 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.998(4) _cell_length_b 13.785(6) _cell_length_c 16.476(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2043.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2840 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 21.95 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7084 _exptl_absorpt_correction_T_max 0.8865 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12128 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3617 _reflns_number_gt 3016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(19) _refine_ls_number_reflns 3617 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.19251(5) 0.83437(4) 0.37096(3) 0.03956(15) Uani 1 1 d . . . Cl1 Cl -0.05734(13) 1.13221(7) 0.36771(9) 0.0653(3) Uani 1 1 d . . . Cl2 Cl -0.11900(13) 0.56906(7) 0.32999(7) 0.0545(3) Uani 1 1 d . . . Cl3 Cl 0.37026(15) 0.81741(9) 0.46427(8) 0.0709(4) Uani 1 1 d . . . Cl4 Cl 0.27440(12) 0.85022(8) 0.23992(6) 0.0522(3) Uani 1 1 d . . . N1 N -0.0332(3) 0.8466(2) 0.35701(19) 0.0395(8) Uani 1 1 d . . . N2 N 0.1430(4) 0.9931(2) 0.39153(19) 0.0418(8) Uani 1 1 d . . . N3 N 0.1124(3) 0.6826(2) 0.36468(19) 0.0375(7) Uani 1 1 d . . . C1 C -0.0973(4) 0.9355(3) 0.3558(2) 0.0405(10) Uani 1 1 d . . . C2 C -0.2469(5) 0.9464(3) 0.3408(3) 0.0581(12) Uani 1 1 d . . . H2 H -0.2900 1.0077 0.3387 0.070 Uiso 1 1 calc R . . C3 C -0.3313(5) 0.8635(3) 0.3288(3) 0.0643(14) Uani 1 1 d . . . H3 H -0.4327 0.8690 0.3187 0.077 Uiso 1 1 calc R . . C4 C -0.2667(5) 0.7730(3) 0.3315(3) 0.0545(12) Uani 1 1 d . . . H4 H -0.3236 0.7173 0.3249 0.065 Uiso 1 1 calc R . . C5 C -0.1149(4) 0.7669(3) 0.3443(2) 0.0408(10) Uani 1 1 d . . . C6 C 0.0115(5) 1.0141(3) 0.3743(3) 0.0428(9) Uani 1 1 d . . . C7 C 0.2531(5) 1.0631(3) 0.4146(3) 0.0418(10) Uani 1 1 d . . . C8 C 0.2734(5) 1.0851(3) 0.4954(3) 0.0536(11) Uani 1 1 d . . . H8 H 0.2133 1.0563 0.5345 0.064 Uiso 1 1 calc R . . C9 C 0.3830(6) 1.1498(3) 0.5185(3) 0.0633(13) Uani 1 1 d . . . H9 H 0.3942 1.1655 0.5731 0.076 Uiso 1 1 calc R . . C10 C 0.4734(5) 1.1902(3) 0.4630(3) 0.0606(13) Uani 1 1 d . . . H10 H 0.5473 1.2331 0.4796 0.073 Uiso 1 1 calc R . . C11 C 0.4574(6) 1.1690(4) 0.3830(3) 0.0731(14) Uani 1 1 d . . . H11 H 0.5199 1.1974 0.3449 0.088 Uiso 1 1 calc R . . C12 C 0.3481(6) 1.1049(4) 0.3585(3) 0.0745(16) Uani 1 1 d . . . H12 H 0.3382 1.0898 0.3037 0.089 Uiso 1 1 calc R . . C13 C -0.0250(4) 0.6769(3) 0.3498(2) 0.0411(9) Uani 1 1 d . . . C14 C 0.2096(4) 0.6007(2) 0.3735(3) 0.0398(9) Uani 1 1 d . . . C15 C 0.3412(5) 0.6005(3) 0.3311(3) 0.0537(12) Uani 1 1 d . . . H15 H 0.3658 0.6522 0.2975 0.064 Uiso 1 1 calc R . . C16 C 0.4366(5) 0.5225(3) 0.3390(3) 0.0693(15) Uani 1 1 d . . . H16 H 0.5246 0.5212 0.3095 0.083 Uiso 1 1 calc R . . C17 C 0.4032(6) 0.4477(3) 0.3895(3) 0.0686(15) Uani 1 1 d . . . H17 H 0.4677 0.3952 0.3938 0.082 Uiso 1 1 calc R . . C18 C 0.2760(6) 0.4491(3) 0.4337(3) 0.0702(14) Uani 1 1 d . . . H18 H 0.2545 0.3979 0.4685 0.084 Uiso 1 1 calc R . . C19 C 0.1782(5) 0.5258(3) 0.4276(3) 0.0581(12) Uani 1 1 d . . . H19 H 0.0925 0.5275 0.4591 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0313(3) 0.0388(3) 0.0486(3) 0.0004(3) -0.0037(3) -0.0006(2) Cl1 0.0637(7) 0.0406(6) 0.0917(9) -0.0057(6) 0.0023(8) 0.0138(5) Cl2 0.0527(7) 0.0419(6) 0.0688(8) -0.0014(5) -0.0113(6) -0.0130(5) Cl3 0.0799(8) 0.0662(8) 0.0666(8) -0.0006(6) -0.0343(7) 0.0008(7) Cl4 0.0528(7) 0.0532(6) 0.0506(6) 0.0068(5) 0.0062(5) 0.0010(5) N1 0.0343(17) 0.0388(17) 0.046(2) -0.0034(16) -0.0010(14) -0.0003(15) N2 0.043(2) 0.0364(17) 0.047(2) -0.0007(15) -0.0029(16) 0.0010(15) N3 0.0340(17) 0.0366(16) 0.0420(18) 0.0009(15) 0.0010(15) -0.0024(13) C1 0.037(2) 0.041(2) 0.043(3) 0.0004(19) -0.0020(19) 0.0115(18) C2 0.042(3) 0.060(3) 0.073(3) 0.003(2) -0.003(2) 0.010(2) C3 0.031(2) 0.072(3) 0.089(4) 0.002(3) -0.015(2) 0.008(2) C4 0.037(3) 0.051(3) 0.076(3) 0.000(2) -0.010(2) -0.005(2) C5 0.028(2) 0.046(2) 0.049(3) -0.0020(19) 0.0008(19) -0.0028(18) C6 0.047(2) 0.038(2) 0.044(2) -0.004(2) 0.002(2) 0.0046(19) C7 0.041(2) 0.034(2) 0.050(3) -0.0019(19) -0.003(2) 0.0012(18) C8 0.065(3) 0.048(2) 0.048(3) -0.001(2) 0.005(2) -0.011(2) C9 0.086(3) 0.051(3) 0.053(3) -0.013(2) -0.009(3) -0.012(3) C10 0.061(3) 0.041(3) 0.079(4) -0.002(2) -0.014(3) -0.009(2) C11 0.076(3) 0.075(3) 0.068(4) -0.002(3) 0.010(3) -0.035(3) C12 0.089(4) 0.085(4) 0.050(3) -0.007(3) 0.002(3) -0.032(3) C13 0.040(2) 0.038(2) 0.045(3) -0.0026(19) -0.0001(18) -0.0082(18) C14 0.038(2) 0.0341(19) 0.048(2) -0.001(2) -0.005(2) -0.0042(16) C15 0.043(3) 0.042(2) 0.076(3) 0.005(2) 0.012(2) 0.0034(19) C16 0.046(3) 0.054(3) 0.108(5) -0.003(3) 0.014(3) 0.010(2) C17 0.053(3) 0.047(3) 0.106(5) 0.004(3) -0.006(3) 0.012(2) C18 0.069(4) 0.058(3) 0.084(4) 0.023(3) -0.001(3) 0.007(3) C19 0.051(3) 0.063(3) 0.060(3) 0.011(2) 0.001(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.051(3) . ? Co1 N3 2.215(3) . ? Co1 Cl3 2.2308(14) . ? Co1 N2 2.258(3) . ? Co1 Cl4 2.2917(14) . ? Cl1 C6 1.746(4) . ? Cl2 C13 1.742(4) . ? N1 C5 1.339(5) . ? N1 C1 1.354(5) . ? N2 C6 1.251(5) . ? N2 C7 1.434(5) . ? N3 C13 1.263(5) . ? N3 C14 1.435(4) . ? C1 C2 1.376(6) . ? C1 C6 1.492(6) . ? C2 C3 1.388(6) . ? C2 H2 0.9300 . ? C3 C4 1.376(6) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 C13 1.484(5) . ? C7 C8 1.378(5) . ? C7 C12 1.384(6) . ? C8 C9 1.383(6) . ? C8 H8 0.9300 . ? C9 C10 1.345(6) . ? C9 H9 0.9300 . ? C10 C11 1.358(6) . ? C10 H10 0.9300 . ? C11 C12 1.382(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C14 C15 1.375(5) . ? C14 C19 1.394(6) . ? C15 C16 1.382(6) . ? C15 H15 0.9300 . ? C16 C17 1.359(7) . ? C16 H16 0.9300 . ? C17 C18 1.357(7) . ? C17 H17 0.9300 . ? C18 C19 1.379(6) . ? C18 H18 0.9300 . ? C19 H19 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 N3 75.54(11) . . ? N1 Co1 Cl3 142.74(10) . . ? N3 Co1 Cl3 99.59(9) . . ? N1 Co1 N2 75.04(12) . . ? N3 Co1 N2 149.07(11) . . ? Cl3 Co1 N2 98.02(9) . . ? N1 Co1 Cl4 101.83(10) . . ? N3 Co1 Cl4 98.67(9) . . ? Cl3 Co1 Cl4 115.39(6) . . ? N2 Co1 Cl4 96.45(9) . . ? C5 N1 C1 120.4(3) . . ? C5 N1 Co1 119.6(3) . . ? C1 N1 Co1 119.9(3) . . ? C6 N2 C7 123.9(3) . . ? C6 N2 Co1 112.1(3) . . ? C7 N2 Co1 123.8(2) . . ? C13 N3 C14 124.6(3) . . ? C13 N3 Co1 112.7(3) . . ? C14 N3 Co1 122.7(2) . . ? N1 C1 C2 121.2(4) . . ? N1 C1 C6 112.0(3) . . ? C2 C1 C6 126.8(4) . . ? C1 C2 C3 118.1(4) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.7(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.5(4) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 121.0(4) . . ? N1 C5 C13 112.2(3) . . ? C4 C5 C13 126.7(4) . . ? N2 C6 C1 120.0(3) . . ? N2 C6 Cl1 124.4(3) . . ? C1 C6 Cl1 115.6(3) . . ? C8 C7 C12 118.1(4) . . ? C8 C7 N2 119.7(4) . . ? C12 C7 N2 122.0(4) . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.4(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.8(5) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C7 C12 C11 120.7(5) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N3 C13 C5 119.6(3) . . ? N3 C13 Cl2 124.4(3) . . ? C5 C13 Cl2 116.0(3) . . ? C15 C14 C19 119.8(4) . . ? C15 C14 N3 118.4(3) . . ? C19 C14 N3 121.6(4) . . ? C14 C15 C16 119.3(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.7(5) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.3(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.7(5) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 119.1(4) . . ? C18 C19 H19 120.5 . . ? C14 C19 H19 120.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.590 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 903517' ####################################################################### # # 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_x107 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 Cl6 Co N3' _chemical_formula_weight 625.08 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9379(7) _cell_length_b 15.0989(8) _cell_length_c 14.3818(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.1770(10) _cell_angle_gamma 90.00 _cell_volume 2669.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 188(2) _cell_measurement_reflns_used 6764 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 1.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7774 _exptl_absorpt_correction_T_max 0.8841 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 188(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16725 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.03 _reflns_number_total 5238 _reflns_number_gt 4615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+1.0694P] 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 5238 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.18237(2) 0.165940(17) 0.26375(2) 0.02471(9) Uani 1 1 d . . . Cl1 Cl 0.19688(5) 0.06215(4) 0.15652(4) 0.03468(13) Uani 1 1 d . . . Cl2 Cl 0.24790(4) 0.12566(3) 0.42179(4) 0.02996(13) Uani 1 1 d . . . Cl3 Cl -0.19117(4) 0.23291(4) 0.18290(5) 0.04154(15) Uani 1 1 d . . . Cl4 Cl 0.37658(5) 0.39998(3) 0.18062(4) 0.03737(14) Uani 1 1 d . . . Cl5 Cl -0.05405(6) 0.43567(5) 0.37199(5) 0.05743(19) Uani 1 1 d . . . Cl6 Cl 0.15451(6) 0.34406(4) 0.43588(5) 0.05350(18) Uani 1 1 d . . . N1 N -0.00133(13) 0.15163(10) 0.24542(12) 0.0228(4) Uani 1 1 d . . . N2 N 0.11314(13) 0.28271(10) 0.20060(11) 0.0218(3) Uani 1 1 d . . . N3 N 0.32553(14) 0.25264(11) 0.25575(12) 0.0259(4) Uani 1 1 d . . . C1 C -0.05244(16) 0.22033(13) 0.20678(14) 0.0237(4) Uani 1 1 d . . . C2 C 0.00583(16) 0.29646(13) 0.18016(14) 0.0237(4) Uani 1 1 d . . . C3 C -0.04334(18) 0.37539(14) 0.14063(16) 0.0299(5) Uani 1 1 d . . . H3 H -0.1195 0.3836 0.1261 0.036 Uiso 1 1 calc R . . C4 C 0.02176(19) 0.44206(14) 0.12291(16) 0.0333(5) Uani 1 1 d . . . H4 H -0.0096 0.4972 0.0971 0.040 Uiso 1 1 calc R . . C5 C 0.13221(18) 0.42849(13) 0.14264(15) 0.0299(5) Uani 1 1 d . . . H5 H 0.1775 0.4733 0.1298 0.036 Uiso 1 1 calc R . . C6 C 0.17507(17) 0.34720(13) 0.18182(14) 0.0243(4) Uani 1 1 d . . . C7 C 0.29217(17) 0.32407(13) 0.21067(15) 0.0251(4) Uani 1 1 d . . . C8 C 0.44003(17) 0.23092(14) 0.29153(17) 0.0306(5) Uani 1 1 d . . . C9 C 0.4877(2) 0.18716(15) 0.2297(2) 0.0422(6) Uani 1 1 d . . . C10 C 0.5971(2) 0.16122(18) 0.2721(3) 0.0611(9) Uani 1 1 d . . . H10 H 0.6324 0.1295 0.2336 0.073 Uiso 1 1 calc R . . C11 C 0.6536(2) 0.1809(2) 0.3677(3) 0.0667(9) Uani 1 1 d . . . H11 H 0.7265 0.1611 0.3949 0.080 Uiso 1 1 calc R . . C12 C 0.6057(2) 0.22885(19) 0.4245(2) 0.0539(7) Uani 1 1 d . . . H12 H 0.6469 0.2445 0.4895 0.065 Uiso 1 1 calc R . . C13 C 0.49726(18) 0.25456(16) 0.38748(18) 0.0369(5) Uani 1 1 d . . . C14 C -0.05854(16) 0.07972(13) 0.27485(15) 0.0247(4) Uani 1 1 d . . . C15 C -0.10149(17) 0.01105(14) 0.20887(17) 0.0306(5) Uani 1 1 d . . . C16 C -0.15187(18) -0.05848(14) 0.24259(19) 0.0387(6) Uani 1 1 d . . . H16 H -0.1817 -0.1065 0.2000 0.046 Uiso 1 1 calc R . . C17 C -0.15915(19) -0.05890(15) 0.3361(2) 0.0414(6) Uani 1 1 d . . . H17 H -0.1923 -0.1076 0.3577 0.050 Uiso 1 1 calc R . . C18 C -0.11868(18) 0.01077(15) 0.39849(18) 0.0367(5) Uani 1 1 d . . . H18 H -0.1256 0.0103 0.4623 0.044 Uiso 1 1 calc R . . C19 C -0.06766(17) 0.08211(13) 0.36925(16) 0.0283(5) Uani 1 1 d . . . C20 C -0.0261(2) 0.15923(14) 0.43647(17) 0.0337(5) Uani 1 1 d . . . H20A H 0.0512 0.1684 0.4447 0.051 Uiso 1 1 calc R . . H20B H -0.0355 0.1470 0.5003 0.051 Uiso 1 1 calc R . . H20C H -0.0670 0.2126 0.4083 0.051 Uiso 1 1 calc R . . C21 C -0.0955(2) 0.01214(16) 0.10637(17) 0.0399(6) Uani 1 1 d . . . H21A H -0.1241 -0.0437 0.0737 0.060 Uiso 1 1 calc R . . H21B H -0.0196 0.0193 0.1082 0.060 Uiso 1 1 calc R . . H21C H -0.1388 0.0616 0.0702 0.060 Uiso 1 1 calc R . . C22 C 0.4455(2) 0.30897(17) 0.44835(17) 0.0410(6) Uani 1 1 d . . . H22A H 0.4130 0.3623 0.4120 0.061 Uiso 1 1 calc R . . H22B H 0.5009 0.3261 0.5095 0.061 Uiso 1 1 calc R . . H22C H 0.3888 0.2740 0.4633 0.061 Uiso 1 1 calc R . . C23 C 0.4284(2) 0.17390(17) 0.1232(2) 0.0527(7) Uani 1 1 d . . . H23A H 0.3604 0.1419 0.1158 0.079 Uiso 1 1 calc R . . H23B H 0.4740 0.1395 0.0933 0.079 Uiso 1 1 calc R . . H23C H 0.4120 0.2316 0.0908 0.079 Uiso 1 1 calc R . . C24 C 0.0889(2) 0.44709(17) 0.4097(2) 0.0496(7) Uani 1 1 d . . . H24A H 0.1107 0.4767 0.3573 0.060 Uiso 1 1 calc R . . H24B H 0.1123 0.4850 0.4687 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02756(16) 0.02143(14) 0.02496(16) 0.00217(10) 0.00793(12) 0.00268(11) Cl1 0.0354(3) 0.0345(3) 0.0365(3) -0.0092(2) 0.0146(2) -0.0023(2) Cl2 0.0337(3) 0.0292(3) 0.0253(3) 0.00198(19) 0.0067(2) 0.0026(2) Cl3 0.0208(3) 0.0336(3) 0.0688(4) 0.0146(3) 0.0118(3) 0.0043(2) Cl4 0.0342(3) 0.0288(3) 0.0542(4) 0.0028(2) 0.0213(3) -0.0083(2) Cl5 0.0510(4) 0.0662(4) 0.0575(4) -0.0045(3) 0.0205(3) 0.0050(3) Cl6 0.0515(4) 0.0446(4) 0.0586(4) -0.0048(3) 0.0087(3) -0.0009(3) N1 0.0221(9) 0.0220(8) 0.0248(9) 0.0002(6) 0.0082(7) -0.0015(7) N2 0.0228(9) 0.0203(8) 0.0218(8) -0.0008(6) 0.0065(7) -0.0015(6) N3 0.0264(9) 0.0258(9) 0.0273(9) -0.0010(7) 0.0110(7) -0.0021(7) C1 0.0192(10) 0.0257(10) 0.0251(10) 0.0009(8) 0.0054(8) 0.0012(8) C2 0.0239(10) 0.0242(10) 0.0217(10) -0.0005(8) 0.0053(8) -0.0017(8) C3 0.0271(11) 0.0287(11) 0.0304(11) 0.0054(9) 0.0040(9) 0.0032(9) C4 0.0369(13) 0.0250(11) 0.0342(12) 0.0066(9) 0.0057(10) 0.0025(9) C5 0.0352(12) 0.0228(10) 0.0304(11) 0.0036(8) 0.0084(10) -0.0050(9) C6 0.0280(11) 0.0240(10) 0.0211(10) -0.0014(8) 0.0082(9) -0.0045(8) C7 0.0295(11) 0.0229(10) 0.0256(10) -0.0041(8) 0.0125(9) -0.0076(8) C8 0.0231(11) 0.0281(11) 0.0449(13) 0.0063(9) 0.0166(10) 0.0001(8) C9 0.0415(14) 0.0297(11) 0.0679(17) 0.0002(11) 0.0354(13) -0.0043(10) C10 0.0470(18) 0.0414(15) 0.115(3) 0.0040(16) 0.054(2) 0.0048(13) C11 0.0289(15) 0.0618(19) 0.109(3) 0.0248(19) 0.0212(18) 0.0108(13) C12 0.0285(13) 0.0625(18) 0.0679(19) 0.0226(15) 0.0108(13) 0.0018(12) C13 0.0244(11) 0.0400(12) 0.0449(14) 0.0128(10) 0.0085(10) -0.0021(10) C14 0.0184(10) 0.0215(9) 0.0337(11) 0.0036(8) 0.0076(9) 0.0019(7) C15 0.0211(10) 0.0270(10) 0.0409(12) -0.0005(9) 0.0059(9) 0.0030(8) C16 0.0266(12) 0.0245(11) 0.0601(16) -0.0034(10) 0.0065(11) -0.0059(9) C17 0.0316(13) 0.0314(12) 0.0635(17) 0.0093(11) 0.0180(12) -0.0070(10) C18 0.0311(12) 0.0370(12) 0.0457(14) 0.0105(10) 0.0175(11) 0.0007(10) C19 0.0226(11) 0.0269(10) 0.0370(12) 0.0060(9) 0.0114(9) 0.0022(8) C20 0.0372(13) 0.0342(12) 0.0339(12) -0.0006(9) 0.0170(10) -0.0004(10) C21 0.0378(13) 0.0387(13) 0.0394(13) -0.0087(10) 0.0065(11) -0.0026(10) C22 0.0347(13) 0.0519(14) 0.0325(12) 0.0008(11) 0.0049(10) -0.0089(11) C23 0.071(2) 0.0399(14) 0.0678(19) -0.0134(13) 0.0512(17) -0.0111(13) C24 0.0532(17) 0.0379(14) 0.0645(18) -0.0079(12) 0.0282(14) -0.0061(12) _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 N2 2.0562(16) . ? Co1 Cl2 2.2477(6) . ? Co1 Cl1 2.2473(6) . ? Co1 N3 2.3001(17) . ? Co1 N1 2.3182(16) . ? Cl3 C1 1.729(2) . ? Cl4 C7 1.7285(19) . ? Cl5 C24 1.766(3) . ? Cl6 C24 1.756(3) . ? N1 C1 1.262(2) . ? N1 C14 1.450(2) . ? N2 C6 1.341(2) . ? N2 C2 1.343(3) . ? N3 C7 1.263(3) . ? N3 C8 1.446(3) . ? C1 C2 1.489(3) . ? C2 C3 1.387(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.482(3) . ? C8 C13 1.394(3) . ? C8 C9 1.396(3) . ? C9 C10 1.410(4) . ? C9 C23 1.498(4) . ? C10 C11 1.373(5) . ? C10 H10 0.9500 . ? C11 C12 1.376(5) . ? C11 H11 0.9500 . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C22 1.502(3) . ? C14 C19 1.399(3) . ? C14 C15 1.398(3) . ? C15 C16 1.400(3) . ? C15 C21 1.500(3) . ? C16 C17 1.377(4) . ? C16 H16 0.9500 . ? C17 C18 1.376(3) . ? C17 H17 0.9500 . ? C18 C19 1.395(3) . ? C18 H18 0.9500 . ? C19 C20 1.502(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 N2 Co1 Cl2 130.81(5) . . ? N2 Co1 Cl1 114.39(5) . . ? Cl2 Co1 Cl1 114.79(2) . . ? N2 Co1 N3 74.72(6) . . ? Cl2 Co1 N3 98.57(5) . . ? Cl1 Co1 N3 96.98(4) . . ? N2 Co1 N1 74.92(6) . . ? Cl2 Co1 N1 98.03(4) . . ? Cl1 Co1 N1 99.16(4) . . ? N3 Co1 N1 149.36(6) . . ? C1 N1 C14 119.94(17) . . ? C1 N1 Co1 110.56(13) . . ? C14 N1 Co1 129.44(12) . . ? C6 N2 C2 119.06(16) . . ? C6 N2 Co1 120.42(13) . . ? C2 N2 Co1 120.50(13) . . ? C7 N3 C8 121.62(17) . . ? C7 N3 Co1 111.11(14) . . ? C8 N3 Co1 127.20(13) . . ? N1 C1 C2 120.67(18) . . ? N1 C1 Cl3 123.12(15) . . ? C2 C1 Cl3 116.21(14) . . ? N2 C2 C3 122.24(18) . . ? N2 C2 C1 113.35(16) . . ? C3 C2 C1 124.38(18) . . ? C4 C3 C2 118.2(2) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C4 C3 120.21(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 118.01(19) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? N2 C6 C5 122.30(19) . . ? N2 C6 C7 113.28(17) . . ? C5 C6 C7 124.38(18) . . ? N3 C7 C6 120.04(18) . . ? N3 C7 Cl4 123.59(17) . . ? C6 C7 Cl4 116.36(14) . . ? C13 C8 C9 123.2(2) . . ? C13 C8 N3 117.58(19) . . ? C9 C8 N3 119.2(2) . . ? C8 C9 C10 116.1(3) . . ? C8 C9 C23 121.8(2) . . ? C10 C9 C23 122.0(2) . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.7(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 120.4(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 117.9(2) . . ? C12 C13 C22 120.6(2) . . ? C8 C13 C22 121.4(2) . . ? C19 C14 C15 122.79(19) . . ? C19 C14 N1 117.98(18) . . ? C15 C14 N1 119.23(18) . . ? C14 C15 C16 116.8(2) . . ? C14 C15 C21 121.82(19) . . ? C16 C15 C21 121.4(2) . . ? C17 C16 C15 121.5(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C14 117.6(2) . . ? C18 C19 C20 120.8(2) . . ? C14 C19 C20 121.54(18) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C13 C22 H22A 109.5 . . ? C13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C9 C23 H23A 109.5 . . ? C9 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C9 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Cl6 C24 Cl5 111.66(14) . . ? Cl6 C24 H24A 109.3 . . ? Cl5 C24 H24A 109.3 . . ? Cl6 C24 H24B 109.3 . . ? Cl5 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.571 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 941866' ####################################################################### # # 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_x126 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 Cl8 Co N3' _chemical_formula_weight 693.97 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1076(7) _cell_length_b 22.7160(18) _cell_length_c 16.3196(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.8210(10) _cell_angle_gamma 90.00 _cell_volume 2941.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 188(2) _cell_measurement_reflns_used 2070 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.48 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1396 _exptl_absorpt_coefficient_mu 1.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7496 _exptl_absorpt_correction_T_max 0.8675 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 188(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17177 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_unetI/netI 0.0767 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5205 _reflns_number_gt 3429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^] 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 5205 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.79979(7) 0.23281(2) 0.16615(3) 0.02717(17) Uani 1 1 d . . . Cl1 Cl 0.95228(15) 0.18585(5) 0.08536(7) 0.0385(3) Uani 1 1 d . . . Cl2 Cl 0.54360(14) 0.26654(5) 0.11029(7) 0.0401(3) Uani 1 1 d . . . Cl3 Cl 0.82133(15) 0.08932(5) 0.37262(7) 0.0421(3) Uani 1 1 d . . . Cl4 Cl 1.17361(19) 0.38936(6) 0.25608(8) 0.0609(4) Uani 1 1 d . . . Cl5 Cl 0.19914(17) -0.01161(6) 0.07465(9) 0.0594(4) Uani 1 1 d . . . Cl6 Cl 0.73783(18) 0.49837(6) -0.10123(9) 0.0611(4) Uani 1 1 d . . . N1 N 0.7337(4) 0.15307(14) 0.2348(2) 0.0256(8) Uani 1 1 d . . . N2 N 0.9594(4) 0.23713(14) 0.28036(19) 0.0258(8) Uani 1 1 d . . . N3 N 0.9308(4) 0.32290(14) 0.1691(2) 0.0281(8) Uani 1 1 d . . . C1 C 0.8309(5) 0.14751(17) 0.3052(3) 0.0259(10) Uani 1 1 d . . . C2 C 0.9645(5) 0.19235(18) 0.3344(2) 0.0256(10) Uani 1 1 d . . . C3 C 1.0823(5) 0.19002(19) 0.4086(3) 0.0317(11) Uani 1 1 d . . . H3 H 1.0831 0.1583 0.4467 0.038 Uiso 1 1 calc R . . C4 C 1.1988(6) 0.2350(2) 0.4260(3) 0.0352(11) Uani 1 1 d . . . H4 H 1.2829 0.2340 0.4759 0.042 Uiso 1 1 calc R . . C5 C 1.1932(5) 0.28096(19) 0.3712(3) 0.0322(11) Uani 1 1 d . . . H5 H 1.2716 0.3124 0.3833 0.039 Uiso 1 1 calc R . . C6 C 1.0723(5) 0.28086(18) 0.2986(2) 0.0271(10) Uani 1 1 d . . . C7 C 1.0454(6) 0.32804(18) 0.2341(3) 0.0331(11) Uani 1 1 d . . . C8 C 0.8945(6) 0.36849(17) 0.1064(3) 0.0290(10) Uani 1 1 d . . . C9 C 0.9822(5) 0.36963(18) 0.0415(3) 0.0312(11) Uani 1 1 d . . . C10 C 0.9309(6) 0.41067(19) -0.0219(3) 0.0362(11) Uani 1 1 d . . . H10 H 0.9870 0.4125 -0.0676 0.043 Uiso 1 1 calc R . . C11 C 0.8005(6) 0.44839(18) -0.0191(3) 0.0360(12) Uani 1 1 d . . . C12 C 0.7191(6) 0.44801(19) 0.0464(3) 0.0393(12) Uani 1 1 d . . . H12 H 0.6307 0.4753 0.0474 0.047 Uiso 1 1 calc R . . C13 C 0.7650(6) 0.40775(18) 0.1120(3) 0.0350(11) Uani 1 1 d . . . C14 C 0.6062(5) 0.11001(18) 0.2022(3) 0.0276(10) Uani 1 1 d . . . C15 C 0.6510(5) 0.05964(18) 0.1627(3) 0.0299(10) Uani 1 1 d . . . C16 C 0.5234(6) 0.02192(19) 0.1257(3) 0.0371(12) Uani 1 1 d . . . H16 H 0.5499 -0.0129 0.0989 0.045 Uiso 1 1 calc R . . C17 C 0.3586(6) 0.0345(2) 0.1275(3) 0.0376(11) Uani 1 1 d . . . C18 C 0.3158(6) 0.0830(2) 0.1690(3) 0.0373(11) Uani 1 1 d . . . H18 H 0.2011 0.0897 0.1711 0.045 Uiso 1 1 calc R . . C19 C 0.4385(5) 0.12204(18) 0.2079(3) 0.0298(10) Uani 1 1 d . . . C20 C 0.3923(6) 0.17476(19) 0.2542(3) 0.0416(12) Uani 1 1 d . . . H20A H 0.2696 0.1765 0.2481 0.062 Uiso 1 1 calc R . . H20B H 0.4317 0.2106 0.2309 0.062 Uiso 1 1 calc R . . H20C H 0.4454 0.1715 0.3136 0.062 Uiso 1 1 calc R . . C21 C 0.8309(6) 0.04593(19) 0.1596(3) 0.0410(12) Uani 1 1 d . . . H21A H 0.8352 0.0099 0.1271 0.061 Uiso 1 1 calc R . . H21B H 0.8960 0.0403 0.2167 0.061 Uiso 1 1 calc R . . H21C H 0.8789 0.0787 0.1331 0.061 Uiso 1 1 calc R . . C22 C 0.6817(7) 0.4089(2) 0.1857(3) 0.0505(14) Uani 1 1 d . . . H22A H 0.6330 0.3701 0.1924 0.076 Uiso 1 1 calc R . . H22B H 0.5923 0.4386 0.1767 0.076 Uiso 1 1 calc R . . H22C H 0.7653 0.4186 0.2363 0.076 Uiso 1 1 calc R . . C23 C 1.1303(6) 0.3294(2) 0.0396(3) 0.0467(13) Uani 1 1 d . . . H23A H 1.2319 0.3457 0.0755 0.070 Uiso 1 1 calc R . . H23B H 1.1475 0.3263 -0.0180 0.070 Uiso 1 1 calc R . . H23C H 1.1074 0.2903 0.0600 0.070 Uiso 1 1 calc R . . C24 C 0.7633(7) 0.3312(3) 0.4702(3) 0.0603(16) Uani 1 1 d . . . H24A H 0.6865 0.3573 0.4935 0.072 Uiso 1 1 calc R . . H24B H 0.8017 0.2996 0.5116 0.072 Uiso 1 1 calc R . . Cl7 Cl 0.6523(2) 0.29938(8) 0.37716(10) 0.0791(5) Uani 1 1 d . . . Cl8 Cl 0.9372(2) 0.37174(6) 0.45534(11) 0.0771(5) 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 0.0262(3) 0.0314(3) 0.0216(3) 0.0016(3) -0.0004(2) 0.0040(3) Cl1 0.0442(7) 0.0384(7) 0.0355(7) 0.0057(5) 0.0142(6) 0.0123(6) Cl2 0.0276(6) 0.0461(7) 0.0430(7) 0.0076(6) -0.0016(5) 0.0085(5) Cl3 0.0473(8) 0.0411(7) 0.0375(7) 0.0164(6) 0.0076(6) 0.0005(6) Cl4 0.0735(10) 0.0435(8) 0.0529(9) 0.0058(7) -0.0171(7) -0.0263(7) Cl5 0.0446(8) 0.0578(9) 0.0671(9) -0.0068(7) -0.0086(7) -0.0156(7) Cl6 0.0588(9) 0.0514(8) 0.0645(9) 0.0333(7) -0.0071(7) 0.0001(7) N1 0.026(2) 0.0236(19) 0.027(2) 0.0008(16) 0.0040(17) 0.0028(16) N2 0.028(2) 0.028(2) 0.0194(18) -0.0005(16) 0.0012(15) 0.0054(17) N3 0.030(2) 0.025(2) 0.028(2) 0.0007(16) 0.0015(17) 0.0027(16) C1 0.028(2) 0.026(2) 0.026(2) 0.0055(19) 0.011(2) 0.0039(19) C2 0.028(2) 0.030(2) 0.020(2) -0.003(2) 0.0067(19) 0.004(2) C3 0.035(3) 0.037(3) 0.023(2) 0.002(2) 0.003(2) 0.008(2) C4 0.037(3) 0.044(3) 0.020(2) -0.005(2) -0.004(2) 0.006(2) C5 0.034(3) 0.031(3) 0.028(2) -0.010(2) -0.002(2) -0.003(2) C6 0.030(3) 0.028(2) 0.022(2) -0.0046(19) 0.002(2) 0.003(2) C7 0.036(3) 0.027(3) 0.035(3) -0.006(2) 0.006(2) -0.002(2) C8 0.034(3) 0.018(2) 0.031(3) 0.0051(19) -0.003(2) -0.003(2) C9 0.027(2) 0.028(2) 0.036(3) 0.003(2) 0.001(2) -0.003(2) C10 0.036(3) 0.037(3) 0.034(3) 0.010(2) 0.003(2) -0.008(2) C11 0.035(3) 0.021(2) 0.043(3) 0.013(2) -0.010(2) -0.004(2) C12 0.036(3) 0.024(3) 0.052(3) -0.001(2) -0.004(2) 0.008(2) C13 0.045(3) 0.023(2) 0.033(3) -0.008(2) -0.002(2) 0.001(2) C14 0.026(2) 0.028(2) 0.028(2) 0.005(2) 0.005(2) 0.000(2) C15 0.026(2) 0.026(2) 0.038(3) 0.003(2) 0.007(2) 0.001(2) C16 0.042(3) 0.026(3) 0.042(3) 0.000(2) 0.005(2) 0.002(2) C17 0.035(3) 0.036(3) 0.039(3) 0.003(2) 0.001(2) -0.006(2) C18 0.023(2) 0.049(3) 0.040(3) 0.009(2) 0.005(2) 0.000(2) C19 0.028(3) 0.036(3) 0.026(2) 0.007(2) 0.006(2) 0.003(2) C20 0.037(3) 0.046(3) 0.045(3) -0.004(2) 0.018(2) 0.005(2) C21 0.040(3) 0.035(3) 0.052(3) -0.001(2) 0.018(3) 0.004(2) C22 0.065(4) 0.041(3) 0.046(3) -0.007(3) 0.012(3) 0.020(3) C23 0.041(3) 0.047(3) 0.053(3) 0.013(3) 0.014(3) 0.006(3) C24 0.049(4) 0.081(4) 0.053(4) 0.010(3) 0.016(3) -0.012(3) Cl7 0.0622(10) 0.1108(14) 0.0651(11) -0.0194(10) 0.0149(8) -0.0056(10) Cl8 0.0934(12) 0.0463(9) 0.1062(13) -0.0126(9) 0.0546(11) -0.0177(8) _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 N2 2.042(3) . ? Co1 Cl2 2.2264(12) . ? Co1 N1 2.251(3) . ? Co1 Cl1 2.2522(12) . ? Co1 N3 2.302(3) . ? Cl3 C1 1.732(4) . ? Cl4 C7 1.731(4) . ? Cl5 C17 1.749(5) . ? Cl6 C11 1.751(4) . ? N1 C1 1.259(5) . ? N1 C14 1.443(5) . ? N2 C6 1.342(5) . ? N2 C2 1.341(5) . ? N3 C7 1.264(5) . ? N3 C8 1.443(5) . ? C1 C2 1.492(6) . ? C2 C3 1.382(5) . ? C3 C4 1.380(6) . ? C3 H3 0.9500 . ? C4 C5 1.369(6) . ? C4 H4 0.9500 . ? C5 C6 1.375(5) . ? C5 H5 0.9500 . ? C6 C7 1.487(6) . ? C8 C9 1.392(6) . ? C8 C13 1.394(6) . ? C9 C10 1.392(6) . ? C9 C23 1.514(6) . ? C10 C11 1.369(6) . ? C10 H10 0.9500 . ? C11 C12 1.366(6) . ? C12 C13 1.399(6) . ? C12 H12 0.9500 . ? C13 C22 1.495(6) . ? C14 C15 1.397(6) . ? C14 C19 1.409(6) . ? C15 C16 1.383(6) . ? C15 C21 1.502(6) . ? C16 C17 1.372(6) . ? C16 H16 0.9500 . ? C17 C18 1.374(6) . ? C18 C19 1.387(6) . ? C18 H18 0.9500 . ? C19 C20 1.504(6) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 Cl8 1.743(5) . ? C24 Cl7 1.754(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 N2 Co1 Cl2 136.11(10) . . ? N2 Co1 N1 75.85(13) . . ? Cl2 Co1 N1 100.57(9) . . ? N2 Co1 Cl1 103.65(10) . . ? Cl2 Co1 Cl1 120.08(5) . . ? N1 Co1 Cl1 97.21(9) . . ? N2 Co1 N3 74.61(13) . . ? Cl2 Co1 N3 95.19(9) . . ? N1 Co1 N3 149.41(12) . . ? Cl1 Co1 N3 97.29(9) . . ? C1 N1 C14 122.4(4) . . ? C1 N1 Co1 111.5(3) . . ? C14 N1 Co1 126.0(3) . . ? C6 N2 C2 119.2(4) . . ? C6 N2 Co1 120.9(3) . . ? C2 N2 Co1 119.5(3) . . ? C7 N3 C8 122.4(4) . . ? C7 N3 Co1 110.9(3) . . ? C8 N3 Co1 126.7(3) . . ? N1 C1 C2 120.0(4) . . ? N1 C1 Cl3 123.7(3) . . ? C2 C1 Cl3 116.2(3) . . ? N2 C2 C3 121.9(4) . . ? N2 C2 C1 112.7(4) . . ? C3 C2 C1 125.5(4) . . ? C2 C3 C4 118.2(4) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 118.9(4) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N2 C6 C5 121.7(4) . . ? N2 C6 C7 112.4(4) . . ? C5 C6 C7 125.8(4) . . ? N3 C7 C6 120.2(4) . . ? N3 C7 Cl4 123.7(4) . . ? C6 C7 Cl4 116.0(3) . . ? C9 C8 C13 123.1(4) . . ? C9 C8 N3 119.4(4) . . ? C13 C8 N3 117.4(4) . . ? C8 C9 C10 117.2(4) . . ? C8 C9 C23 122.4(4) . . ? C10 C9 C23 120.4(4) . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 121.5(4) . . ? C12 C11 Cl6 119.4(4) . . ? C10 C11 Cl6 119.0(4) . . ? C11 C12 C13 120.4(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 117.0(4) . . ? C8 C13 C22 122.2(4) . . ? C12 C13 C22 120.7(4) . . ? C15 C14 C19 122.3(4) . . ? C15 C14 N1 119.4(4) . . ? C19 C14 N1 118.2(4) . . ? C16 C15 C14 117.8(4) . . ? C16 C15 C21 120.1(4) . . ? C14 C15 C21 122.1(4) . . ? C15 C16 C17 120.4(4) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 121.6(4) . . ? C18 C17 Cl5 119.2(4) . . ? C16 C17 Cl5 119.3(4) . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 117.2(4) . . ? C18 C19 C20 120.7(4) . . ? C14 C19 C20 122.1(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C13 C22 H22A 109.5 . . ? C13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C9 C23 H23A 109.5 . . ? C9 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C9 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Cl8 C24 Cl7 112.6(3) . . ? Cl8 C24 H24A 109.1 . . ? Cl7 C24 H24A 109.1 . . ? Cl8 C24 H24B 109.1 . . ? Cl7 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.517 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 941867'