# Electronic Supplementary Material (ESI) for Chemical Communications # 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_ok _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 B2 Co F8 N6' _chemical_formula_weight 697.16 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 11.1909(3) _cell_length_b 23.6444(7) _cell_length_c 12.9931(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.386(2) _cell_angle_gamma 90.00 _cell_volume 3178.91(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21057 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5594 _reflns_number_gt 4416 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1304P)^2^+0.9649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5594 _refine_ls_number_parameters 427 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1947 _refine_ls_wR_factor_gt 0.1827 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.83840(4) 0.877518(18) 0.62484(4) 0.0403(2) Uani 1 1 d . . . N3 N 0.8737(3) 0.83739(12) 0.4929(2) 0.0429(6) Uani 1 1 d . . . N6 N 0.6861(3) 0.92401(14) 0.5133(3) 0.0578(8) Uani 1 1 d . . . N4 N 0.7366(3) 0.80818(12) 0.6667(2) 0.0451(7) Uani 1 1 d . . . N1 N 0.9901(3) 0.93676(12) 0.6802(2) 0.0493(7) Uani 1 1 d . . . N2 N 1.0066(3) 0.82543(13) 0.7155(2) 0.0514(7) Uani 1 1 d . . . N5 N 0.7777(3) 0.91280(12) 0.7570(2) 0.0485(7) Uani 1 1 d . . . C11 C 0.9831(4) 0.80755(15) 0.5229(3) 0.0493(8) Uani 1 1 d . . . C25 C 0.6215(4) 0.90224(19) 0.8393(3) 0.0605(10) Uani 1 1 d . . . H25A H 0.5550 0.8812 0.8466 0.073 Uiso 1 1 calc R . . C26 C 0.6791(4) 0.88481(16) 0.7680(3) 0.0510(9) Uani 1 1 d . . . C27 C 0.6314(4) 0.83291(16) 0.6954(3) 0.0555(10) Uani 1 1 d . . . H27A H 0.6009 0.8050 0.7346 0.067 Uiso 1 1 calc R . . H27B H 0.5595 0.8432 0.6277 0.067 Uiso 1 1 calc R . . C14 C 0.8369(4) 0.78158(16) 0.7653(3) 0.0533(9) Uani 1 1 d . . . H14A H 0.8050 0.7456 0.7800 0.064 Uiso 1 1 calc R . . H14B H 0.8532 0.8056 0.8297 0.064 Uiso 1 1 calc R . . C23 C 0.7618(5) 0.98007(18) 0.8887(4) 0.0683(12) Uani 1 1 d . . . H23A H 0.7913 1.0133 0.9286 0.082 Uiso 1 1 calc R . . C16 C 0.5976(4) 0.72030(15) 0.5869(3) 0.0513(9) Uani 1 1 d . . . C15 C 0.6798(4) 0.76747(15) 0.5707(3) 0.0511(9) Uani 1 1 d . . . H15A H 0.7503 0.7507 0.5553 0.061 Uiso 1 1 calc R . . H15B H 0.6277 0.7889 0.5054 0.061 Uiso 1 1 calc R . . C2 C 1.0894(5) 1.0253(2) 0.6818(4) 0.0767(13) Uani 1 1 d . . . H2A H 1.0859 1.0612 0.6516 0.092 Uiso 1 1 calc R . . C28 C 0.6049(5) 0.94517(19) 0.4442(4) 0.0654(11) Uani 1 1 d D . . C7 C 0.7928(4) 0.83608(15) 0.3851(3) 0.0475(8) Uani 1 1 d . . . H7A H 0.7163 0.8566 0.3641 0.057 Uiso 1 1 calc R . . C22 C 0.8186(4) 0.96022(17) 0.8184(3) 0.0593(10) Uani 1 1 d . . . H22A H 0.8876 0.9802 0.8130 0.071 Uiso 1 1 calc R . . C24 C 0.6638(5) 0.95132(19) 0.8996(4) 0.0667(12) Uani 1 1 d . . . H24A H 0.6251 0.9643 0.9470 0.080 Uiso 1 1 calc R . . C1 C 0.9886(4) 0.98900(17) 0.6383(4) 0.0607(10) Uani 1 1 d . . . H1A H 0.9162 1.0005 0.5776 0.073 Uiso 1 1 calc R . . C13 C 0.9601(4) 0.77223(16) 0.7494(3) 0.0594(10) Uani 1 1 d . . . H13A H 0.9472 0.7436 0.6926 0.071 Uiso 1 1 calc R . . H13B H 1.0252 0.7585 0.8183 0.071 Uiso 1 1 calc R . . C5 C 1.0954(4) 0.91996(18) 0.7679(3) 0.0584(10) Uani 1 1 d . . . C21 C 0.4651(4) 0.72611(18) 0.5497(3) 0.0570(10) Uani 1 1 d . . . H21A H 0.4267 0.7600 0.5172 0.068 Uiso 1 1 calc R . . C12 C 1.0758(4) 0.81366(19) 0.6414(3) 0.0616(10) Uani 1 1 d . . . H12A H 1.1255 0.7791 0.6650 0.074 Uiso 1 1 calc R . . H12B H 1.1355 0.8443 0.6466 0.074 Uiso 1 1 calc R . . C6 C 1.0870(4) 0.86104(19) 0.8101(3) 0.0646(11) Uani 1 1 d . . . H6A H 1.1729 0.8449 0.8442 0.078 Uiso 1 1 calc R . . H6B H 1.0490 0.8626 0.8657 0.078 Uiso 1 1 calc R . . C17 C 0.6527(5) 0.66930(17) 0.6349(4) 0.0727(12) Uani 1 1 d . . . H17A H 0.7416 0.6641 0.6593 0.087 Uiso 1 1 calc R . . C10 C 1.0126(5) 0.7755(2) 0.4465(4) 0.0776(14) Uani 1 1 d . . . H10A H 1.0885 0.7544 0.4690 0.093 Uiso 1 1 calc R . . C8 C 0.8166(4) 0.80638(18) 0.3051(3) 0.0616(10) Uani 1 1 d . . . H8A H 0.7592 0.8072 0.2312 0.074 Uiso 1 1 calc R . . C20 C 0.3885(5) 0.6823(2) 0.5602(4) 0.0717(13) Uani 1 1 d . . . H20A H 0.2993 0.6869 0.5348 0.086 Uiso 1 1 calc R . . C19 C 0.4423(7) 0.6330(2) 0.6070(5) 0.0864(17) Uani 1 1 d . . . H19A H 0.3902 0.6035 0.6129 0.104 Uiso 1 1 calc R . . C18 C 0.5745(8) 0.62605(19) 0.6462(6) 0.095(2) Uani 1 1 d . . . H18A H 0.6114 0.5923 0.6803 0.114 Uiso 1 1 calc R . . C4 C 1.2005(4) 0.9551(2) 0.8146(4) 0.0775(13) Uani 1 1 d . . . H4A H 1.2725 0.9427 0.8746 0.093 Uiso 1 1 calc R . . C29 C 0.4959(6) 0.9720(3) 0.3546(4) 0.107(2) Uani 1 1 d D . . C3 C 1.1986(5) 1.0079(3) 0.7726(5) 0.0901(16) Uani 1 1 d . . . H3A H 1.2688 1.0321 0.8038 0.108 Uiso 1 1 calc R . . C9 C 0.9289(6) 0.7751(2) 0.3376(4) 0.0906(17) Uani 1 1 d . . . H9A H 0.9477 0.7538 0.2855 0.109 Uiso 1 1 calc R . . F8 F 0.4961(4) 1.1368(2) 0.8044(3) 0.1313(14) Uani 1 1 d . . . F7 F 0.4021(4) 1.1434(2) 0.9274(4) 0.1499(17) Uani 1 1 d . . . F6 F 0.5257(6) 1.06981(17) 0.9366(5) 0.164(2) Uani 1 1 d . . . B2 B 0.5102(5) 1.1246(2) 0.9144(5) 0.0623(12) Uani 1 1 d . . . F5 F 0.6075(5) 1.1552(3) 0.9821(5) 0.177(2) Uani 1 1 d . . . F4 F 0.8293(6) 1.0957(3) 0.5083(8) 0.241(4) Uani 1 1 d . . . F3 F 0.6759(6) 1.1427(5) 0.4008(9) 0.270(5) Uani 1 1 d . . . B1 B 0.7120(10) 1.1100(4) 0.4877(16) 0.152(5) Uani 1 1 d . . . F2 F 0.6394(11) 1.0760(4) 0.4882(13) 0.370(8) Uani 1 1 d . . . F1 F 0.6961(12) 1.1509(4) 0.5518(8) 0.318(6) Uani 1 1 d . . . H29C H 0.525(2) 1.0078(12) 0.333(3) 0.20(4) Uiso 1 1 d D . . H29B H 0.463(4) 0.9469(12) 0.2898(18) 0.23(5) Uiso 1 1 d D . . H29A H 0.426(2) 0.980(2) 0.381(2) 0.14(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0448(3) 0.0389(3) 0.0365(3) 0.00251(17) 0.0147(2) -0.00074(18) N3 0.0453(16) 0.0436(16) 0.0425(15) 0.0030(12) 0.0197(13) 0.0014(13) N6 0.061(2) 0.061(2) 0.0512(18) 0.0087(15) 0.0211(16) 0.0193(17) N4 0.0599(18) 0.0392(15) 0.0392(14) -0.0019(12) 0.0222(13) -0.0054(13) N1 0.0545(18) 0.0460(17) 0.0476(16) -0.0010(13) 0.0197(14) -0.0092(14) N2 0.0547(18) 0.0513(18) 0.0432(16) 0.0087(13) 0.0129(14) 0.0061(14) N5 0.0625(19) 0.0424(16) 0.0427(15) -0.0069(12) 0.0224(14) -0.0065(14) C11 0.057(2) 0.046(2) 0.051(2) 0.0078(16) 0.0269(17) 0.0065(17) C25 0.073(3) 0.063(3) 0.054(2) -0.002(2) 0.034(2) 0.005(2) C26 0.064(2) 0.049(2) 0.0442(19) 0.0008(15) 0.0247(18) 0.0025(17) C27 0.066(2) 0.054(2) 0.057(2) -0.0112(17) 0.035(2) -0.0138(18) C14 0.075(3) 0.046(2) 0.0396(18) 0.0052(15) 0.0219(18) -0.0039(18) C23 0.099(3) 0.051(2) 0.056(2) -0.0120(19) 0.032(2) 0.004(2) C16 0.071(3) 0.045(2) 0.0444(19) -0.0103(15) 0.0302(18) -0.0111(18) C15 0.068(2) 0.048(2) 0.0424(19) -0.0088(15) 0.0263(18) -0.0143(18) C2 0.091(4) 0.059(3) 0.088(3) -0.005(2) 0.043(3) -0.024(3) C28 0.080(3) 0.065(3) 0.054(2) -0.002(2) 0.030(2) 0.021(2) C7 0.053(2) 0.050(2) 0.0419(18) 0.0040(15) 0.0210(16) -0.0034(16) C22 0.074(3) 0.051(2) 0.055(2) -0.0085(18) 0.028(2) -0.0070(19) C24 0.093(3) 0.061(3) 0.057(2) -0.0043(19) 0.041(2) 0.008(2) C1 0.072(3) 0.052(2) 0.062(2) -0.0008(18) 0.030(2) -0.009(2) C13 0.077(3) 0.046(2) 0.049(2) 0.0123(17) 0.017(2) 0.0104(19) C5 0.055(2) 0.066(2) 0.050(2) -0.0056(18) 0.0151(18) -0.0084(19) C21 0.066(3) 0.059(2) 0.046(2) -0.0074(17) 0.0223(19) -0.012(2) C12 0.055(2) 0.066(3) 0.066(2) 0.011(2) 0.025(2) 0.018(2) C6 0.060(2) 0.074(3) 0.046(2) 0.0077(19) 0.0038(18) 0.002(2) C17 0.083(3) 0.046(2) 0.092(3) -0.005(2) 0.036(3) -0.004(2) C10 0.082(3) 0.082(3) 0.079(3) 0.008(2) 0.041(3) 0.031(3) C8 0.077(3) 0.063(3) 0.047(2) -0.0025(18) 0.026(2) 0.002(2) C20 0.081(3) 0.083(3) 0.059(2) -0.020(2) 0.035(2) -0.034(3) C19 0.116(5) 0.074(3) 0.082(3) -0.018(3) 0.053(3) -0.048(3) C18 0.148(6) 0.039(2) 0.105(4) 0.005(2) 0.055(4) -0.009(3) C4 0.061(3) 0.093(4) 0.066(3) -0.019(3) 0.011(2) -0.021(3) C29 0.115(5) 0.124(5) 0.064(3) 0.020(3) 0.014(3) 0.071(4) C3 0.083(3) 0.093(4) 0.097(4) -0.033(3) 0.037(3) -0.043(3) C9 0.123(5) 0.099(4) 0.060(3) -0.008(3) 0.047(3) 0.033(3) F8 0.138(3) 0.164(3) 0.094(3) 0.025(2) 0.046(2) 0.019(3) F7 0.107(3) 0.222(5) 0.133(4) 0.037(3) 0.060(3) 0.055(3) F6 0.228(5) 0.083(3) 0.190(5) 0.033(3) 0.091(4) 0.034(3) B2 0.061(3) 0.057(3) 0.066(3) -0.001(2) 0.021(2) -0.004(2) F5 0.126(4) 0.203(5) 0.161(4) -0.048(4) 0.010(3) -0.036(4) F4 0.172(6) 0.197(6) 0.371(11) 0.158(7) 0.121(6) 0.074(5) F3 0.126(5) 0.393(12) 0.326(12) 0.158(10) 0.124(6) 0.103(6) B1 0.079(5) 0.084(5) 0.300(18) 0.041(8) 0.080(9) 0.001(4) F2 0.388(13) 0.208(8) 0.67(2) -0.068(11) 0.376(16) -0.144(9) F1 0.452(16) 0.234(9) 0.207(8) 0.018(7) 0.056(9) 0.177(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 N6 2.081(3) . ? Co1 N1 2.105(3) . ? Co1 N3 2.124(3) . ? Co1 N4 2.180(3) . ? Co1 N2 2.181(3) . ? Co1 N5 2.235(3) . ? N3 C11 1.337(5) . ? N3 C7 1.347(4) . ? N6 C28 1.123(5) . ? N4 C27 1.484(5) . ? N4 C14 1.484(5) . ? N4 C15 1.510(4) . ? N1 C5 1.349(5) . ? N1 C1 1.348(5) . ? N2 C12 1.475(5) . ? N2 C6 1.479(5) . ? N2 C13 1.490(5) . ? N5 C26 1.340(5) . ? N5 C22 1.351(5) . ? C11 C10 1.385(6) . ? C11 C12 1.500(5) . ? C25 C26 1.377(5) . ? C25 C24 1.379(6) . ? C26 C27 1.516(5) . ? C14 C13 1.486(6) . ? C23 C24 1.342(6) . ? C23 C22 1.380(6) . ? C16 C21 1.380(6) . ? C16 C17 1.389(6) . ? C16 C15 1.511(5) . ? C2 C1 1.358(6) . ? C2 C3 1.399(8) . ? C28 C29 1.471(6) . ? C7 C8 1.362(5) . ? C5 C4 1.377(6) . ? C5 C6 1.513(6) . ? C21 C20 1.384(6) . ? C17 C18 1.390(7) . ? C10 C9 1.368(7) . ? C8 C9 1.378(7) . ? C20 C19 1.346(8) . ? C19 C18 1.378(9) . ? C4 C3 1.361(8) . ? F8 B2 1.406(7) . ? F7 B2 1.358(6) . ? F6 B2 1.325(6) . ? B2 F5 1.324(7) . ? F4 B1 1.281(10) . ? F3 B1 1.299(15) . ? B1 F2 1.145(10) . ? B1 F1 1.330(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Co1 N1 103.10(13) . . ? N6 Co1 N3 91.62(12) . . ? N1 Co1 N3 101.50(11) . . ? N6 Co1 N4 101.76(13) . . ? N1 Co1 N4 147.68(11) . . ? N3 Co1 N4 98.10(10) . . ? N6 Co1 N2 169.59(12) . . ? N1 Co1 N2 76.90(12) . . ? N3 Co1 N2 78.26(11) . . ? N4 Co1 N2 82.29(12) . . ? N6 Co1 N5 85.99(12) . . ? N1 Co1 N5 86.03(11) . . ? N3 Co1 N5 172.44(11) . . ? N4 Co1 N5 75.43(10) . . ? N2 Co1 N5 104.36(11) . . ? C11 N3 C7 118.0(3) . . ? C11 N3 Co1 115.5(2) . . ? C7 N3 Co1 126.2(2) . . ? C28 N6 Co1 172.2(3) . . ? C27 N4 C14 111.2(3) . . ? C27 N4 C15 109.5(3) . . ? C14 N4 C15 112.6(3) . . ? C27 N4 Co1 107.8(2) . . ? C14 N4 Co1 103.8(2) . . ? C15 N4 Co1 111.6(2) . . ? C5 N1 C1 118.9(3) . . ? C5 N1 Co1 115.1(3) . . ? C1 N1 Co1 125.9(3) . . ? C12 N2 C6 110.2(3) . . ? C12 N2 C13 111.3(3) . . ? C6 N2 C13 114.0(3) . . ? C12 N2 Co1 108.3(2) . . ? C6 N2 Co1 104.7(2) . . ? C13 N2 Co1 108.0(2) . . ? C26 N5 C22 117.1(3) . . ? C26 N5 Co1 113.7(2) . . ? C22 N5 Co1 129.0(3) . . ? N3 C11 C10 121.4(4) . . ? N3 C11 C12 116.6(3) . . ? C10 C11 C12 121.9(4) . . ? C26 C25 C24 119.1(4) . . ? N5 C26 C25 122.6(4) . . ? N5 C26 C27 116.3(3) . . ? C25 C26 C27 121.1(4) . . ? N4 C27 C26 110.5(3) . . ? N4 C14 C13 112.3(3) . . ? C24 C23 C22 119.9(4) . . ? C21 C16 C17 118.5(4) . . ? C21 C16 C15 120.5(4) . . ? C17 C16 C15 120.9(4) . . ? N4 C15 C16 116.3(3) . . ? C1 C2 C3 119.1(5) . . ? N6 C28 C29 178.4(6) . . ? N3 C7 C8 123.7(4) . . ? N5 C22 C23 122.4(4) . . ? C23 C24 C25 118.9(4) . . ? N1 C1 C2 122.0(4) . . ? C14 C13 N2 111.2(3) . . ? N1 C5 C4 121.3(4) . . ? N1 C5 C6 115.0(3) . . ? C4 C5 C6 123.8(4) . . ? C16 C21 C20 120.9(4) . . ? N2 C12 C11 111.0(3) . . ? N2 C6 C5 109.0(3) . . ? C16 C17 C18 119.8(5) . . ? C9 C10 C11 119.2(4) . . ? C7 C8 C9 117.6(4) . . ? C19 C20 C21 120.3(5) . . ? C20 C19 C18 120.2(5) . . ? C19 C18 C17 120.2(5) . . ? C3 C4 C5 119.8(5) . . ? C4 C3 C2 118.8(4) . . ? C10 C9 C8 120.0(4) . . ? F6 B2 F5 112.5(5) . . ? F6 B2 F7 109.9(5) . . ? F5 B2 F7 106.6(5) . . ? F6 B2 F8 112.1(5) . . ? F5 B2 F8 108.0(5) . . ? F7 B2 F8 107.4(5) . . ? F2 B1 F4 119.0(11) . . ? F2 B1 F3 115.9(16) . . ? F4 B1 F3 107.0(11) . . ? F2 B1 F1 104.0(13) . . ? F4 B1 F1 115.6(13) . . ? F3 B1 F1 92.4(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.837 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 937142' ####################################################################### # # 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_ok _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H31 B2 Co F8 N5 O4' _chemical_formula_weight 722.12 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 11.4253(5) _cell_length_b 23.1813(10) _cell_length_c 13.1097(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.606(3) _cell_angle_gamma 90.00 _cell_volume 3228.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 0.619 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19390 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5694 _reflns_number_gt 3864 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1629P)^2^+1.0341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5694 _refine_ls_number_parameters 428 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1129 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2732 _refine_ls_wR_factor_gt 0.2538 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.134 _refine_ls_shift/su_mean 0.017 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co Co 0.32853(6) 0.87797(3) 0.13171(5) 0.0586(2) Uani 1 1 d . . . N2 N 0.3583(3) 0.83855(16) -0.0032(3) 0.0585(9) Uani 1 1 d . . . N1 N 0.4833(4) 0.93507(19) 0.1852(3) 0.0684(11) Uani 1 1 d . . . N3 N 0.4859(4) 0.82103(19) 0.2153(3) 0.0721(11) Uani 1 1 d . . . O1 O 0.1894(4) 0.93094(19) 0.0335(4) 0.1017(14) Uani 1 1 d D . . H1A H 0.1890 0.9610 0.0663 0.153 Uiso 1 1 calc RD . . C12 C 0.2800(5) 0.8405(2) -0.1091(4) 0.0644(12) Uani 1 1 d . . . H12A H 0.2082 0.8633 -0.1278 0.077 Uiso 1 1 calc R . . C8 C 0.4616(5) 0.8067(2) 0.0222(4) 0.0648(12) Uani 1 1 d . . . N4 N 0.2232(4) 0.80720(17) 0.1698(4) 0.0723(11) Uani 1 1 d . . . N5 N 0.2740(4) 0.91248(18) 0.2654(4) 0.0739(11) Uani 1 1 d . . . C21 C 0.1649(5) 0.7672(2) 0.0721(4) 0.0751(14) Uani 1 1 d . . . H21A H 0.1160 0.7904 0.0094 0.090 Uiso 1 1 calc R . . H21B H 0.2325 0.7495 0.0551 0.090 Uiso 1 1 calc R . . C27 C -0.0481(6) 0.7287(3) 0.0518(5) 0.0876(17) Uani 1 1 d . . . H27A H -0.0821 0.7643 0.0232 0.105 Uiso 1 1 calc R . . C16 C 0.1755(6) 0.8861(2) 0.2750(5) 0.0839(17) Uani 1 1 d . . . C22 C 0.0826(6) 0.7205(2) 0.0855(5) 0.0766(14) Uani 1 1 d . . . C1 C 0.4901(6) 0.9868(2) 0.1445(5) 0.0818(15) Uani 1 1 d . . . H1B H 0.4212 0.9998 0.0851 0.098 Uiso 1 1 calc R . . C5 C 0.5827(5) 0.9146(3) 0.2695(4) 0.0830(17) Uani 1 1 d . . . C7 C 0.5514(5) 0.8083(3) 0.1395(4) 0.0811(16) Uani 1 1 d . . . H7A H 0.5936 0.7713 0.1587 0.097 Uiso 1 1 calc R . . H7B H 0.6149 0.8375 0.1476 0.097 Uiso 1 1 calc R . . C24 C 0.0504(11) 0.6242(3) 0.1379(8) 0.128(3) Uani 1 1 d . . . H24A H 0.0845 0.5889 0.1684 0.154 Uiso 1 1 calc R . . C11 C 0.3011(6) 0.8110(3) -0.1893(5) 0.0811(15) Uani 1 1 d . . . H11A H 0.2453 0.8139 -0.2617 0.097 Uiso 1 1 calc R . . C14 C 0.3176(6) 0.7782(3) 0.2646(5) 0.0898(18) Uani 1 1 d . . . H14A H 0.2838 0.7417 0.2776 0.108 Uiso 1 1 calc R . . H14B H 0.3353 0.8020 0.3294 0.108 Uiso 1 1 calc R . . C15 C 0.1235(6) 0.8336(3) 0.1995(6) 0.0910(17) Uani 1 1 d . . . H15A H 0.0908 0.8054 0.2369 0.109 Uiso 1 1 calc R . . H15B H 0.0551 0.8458 0.1336 0.109 Uiso 1 1 calc R . . C23 C 0.1277(8) 0.6673(3) 0.1260(7) 0.109(2) Uani 1 1 d . . . H23A H 0.2133 0.6599 0.1462 0.131 Uiso 1 1 calc R . . C19 C 0.2594(7) 0.9825(3) 0.3928(6) 0.102(2) Uani 1 1 d . . . H19A H 0.2885 1.0168 0.4303 0.123 Uiso 1 1 calc R . . C13 C 0.4375(6) 0.7674(2) 0.2457(5) 0.0915(19) Uani 1 1 d . . . H13A H 0.5002 0.7517 0.3119 0.110 Uiso 1 1 calc R . . H13B H 0.4224 0.7392 0.1876 0.110 Uiso 1 1 calc R . . C17 C 0.1146(7) 0.9058(3) 0.3410(6) 0.101(2) Uani 1 1 d . . . H17A H 0.0447 0.8866 0.3444 0.121 Uiso 1 1 calc R . . C20 C 0.3182(7) 0.9593(3) 0.3270(5) 0.0921(18) Uani 1 1 d . . . H20A H 0.3907 0.9769 0.3256 0.110 Uiso 1 1 calc R . . C9 C 0.4857(6) 0.7746(3) -0.0571(5) 0.099(2) Uani 1 1 d . . . H9A H 0.5570 0.7514 -0.0379 0.119 Uiso 1 1 calc R . . C6 C 0.5678(6) 0.8545(3) 0.3082(5) 0.0907(18) Uani 1 1 d . . . H6A H 0.6495 0.8360 0.3396 0.109 Uiso 1 1 calc R . . H6B H 0.5316 0.8566 0.3644 0.109 Uiso 1 1 calc R . . C26 C -0.1266(7) 0.6860(3) 0.0598(6) 0.098(2) Uani 1 1 d . . . H26A H -0.2129 0.6924 0.0350 0.118 Uiso 1 1 calc R . . C10 C 0.4041(7) 0.7772(3) -0.1634(5) 0.099(2) Uani 1 1 d . . . H10A H 0.4192 0.7559 -0.2174 0.119 Uiso 1 1 calc R . . C25 C -0.0784(10) 0.6335(4) 0.1042(8) 0.124(3) Uani 1 1 d . . . H25A H -0.1312 0.6047 0.1116 0.148 Uiso 1 1 calc R . . C2 C 0.5931(8) 1.0222(4) 0.1852(7) 0.113(2) Uani 1 1 d . . . H2A H 0.5949 1.0582 0.1545 0.136 Uiso 1 1 calc R . . C18 C 0.1601(8) 0.9553(3) 0.4024(7) 0.119(2) Uani 1 1 d . . . H18A H 0.1226 0.9694 0.4494 0.143 Uiso 1 1 calc R . . C4 C 0.6901(6) 0.9486(4) 0.3161(7) 0.119(3) Uani 1 1 d . . . H4A H 0.7588 0.9352 0.3753 0.143 Uiso 1 1 calc R . . C3 C 0.6917(8) 1.0027(5) 0.2718(9) 0.135(3) Uani 1 1 d . . . H3A H 0.7622 1.0260 0.3023 0.162 Uiso 1 1 calc R . . F7 F 1.0756(6) 0.8503(3) 0.5738(6) 0.182(2) Uani 1 1 d . . . F8 F 0.9712(7) 0.9285(3) 0.5401(8) 0.224(3) Uani 1 1 d . . . B2 B 0.9813(7) 0.8795(3) 0.5797(7) 0.086(2) Uani 1 1 d . . . F4 F -0.3400(7) 0.9060(3) 0.0132(8) 0.220(3) Uani 1 1 d . . . F6 F 0.9922(12) 0.8759(6) 0.6860(7) 0.308(6) Uani 1 1 d . . . F5 F 0.8753(7) 0.8547(5) 0.5336(9) 0.261(5) Uani 1 1 d . . . F2 F -0.1986(9) 0.8463(8) 0.1065(14) 0.355(8) Uani 1 1 d . . . F1 F -0.1993(13) 0.8620(5) -0.0405(10) 0.296(5) Uani 1 1 d . . . B1 B -0.230(3) 0.8909(9) 0.037(3) 0.299(12) Uani 1 1 d . . . F3 F -0.1453(15) 0.9279(7) 0.063(2) 0.485(14) Uani 1 1 d . . . O4 O 0.9776(9) 0.8828(6) 0.8755(9) 0.241(5) Uani 1 1 d . . . O3 O 0.0807(17) 0.9697(7) -0.1607(9) 0.342(8) Uani 1 1 d . . . O2 O 0.1661(18) 1.0335(8) 0.1198(13) 0.548(16) Uani 1 1 d . . . H1D H 0.153(7) 0.928(2) -0.0358(18) 0.14(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0727(4) 0.0502(4) 0.0570(4) 0.0023(3) 0.0288(3) 0.0034(3) N2 0.070(2) 0.056(2) 0.056(2) 0.0037(17) 0.0306(18) 0.0023(18) N1 0.078(3) 0.069(3) 0.061(2) -0.002(2) 0.029(2) -0.002(2) N3 0.092(3) 0.068(3) 0.055(2) 0.005(2) 0.026(2) 0.016(2) O1 0.103(3) 0.084(3) 0.103(3) -0.007(2) 0.021(3) 0.030(2) C12 0.070(3) 0.071(3) 0.057(3) 0.006(2) 0.029(2) -0.002(2) C8 0.077(3) 0.066(3) 0.059(3) 0.006(2) 0.034(2) 0.014(2) N4 0.108(3) 0.054(2) 0.072(3) -0.015(2) 0.053(2) -0.014(2) N5 0.103(3) 0.058(2) 0.078(3) -0.016(2) 0.053(2) -0.009(2) C21 0.115(4) 0.059(3) 0.069(3) -0.013(2) 0.055(3) -0.016(3) C27 0.132(5) 0.074(4) 0.070(3) -0.014(3) 0.053(3) -0.016(4) C16 0.116(4) 0.064(3) 0.093(4) -0.023(3) 0.063(4) -0.014(3) C22 0.120(4) 0.054(3) 0.076(3) -0.015(2) 0.060(3) -0.018(3) C1 0.107(4) 0.067(3) 0.081(4) -0.003(3) 0.046(3) -0.016(3) C5 0.085(4) 0.103(4) 0.055(3) -0.018(3) 0.018(3) 0.011(3) C7 0.081(3) 0.096(4) 0.066(3) -0.003(3) 0.025(3) 0.026(3) C24 0.219(10) 0.052(4) 0.135(7) -0.012(4) 0.090(7) -0.026(5) C11 0.098(4) 0.091(4) 0.057(3) -0.002(3) 0.032(3) -0.005(3) C14 0.155(5) 0.063(3) 0.064(3) 0.000(3) 0.055(3) -0.005(3) C15 0.117(4) 0.081(4) 0.103(4) -0.032(3) 0.073(4) -0.024(3) C23 0.147(6) 0.062(4) 0.139(6) -0.014(4) 0.075(5) 0.001(4) C19 0.154(6) 0.065(4) 0.117(5) -0.029(3) 0.083(4) -0.010(4) C13 0.151(5) 0.061(3) 0.063(3) 0.012(3) 0.040(3) 0.026(3) C17 0.116(4) 0.094(5) 0.122(5) -0.036(4) 0.077(4) -0.016(4) C20 0.133(5) 0.068(3) 0.100(4) -0.025(3) 0.072(4) -0.019(3) C9 0.112(4) 0.110(5) 0.077(4) -0.005(3) 0.037(3) 0.043(4) C6 0.097(4) 0.107(5) 0.057(3) 0.004(3) 0.015(3) 0.026(4) C26 0.129(5) 0.098(5) 0.089(4) -0.022(4) 0.064(4) -0.039(4) C10 0.125(5) 0.113(5) 0.064(3) -0.004(3) 0.039(3) 0.032(4) C25 0.163(7) 0.115(6) 0.127(6) -0.037(5) 0.093(6) -0.057(6) C2 0.135(6) 0.100(5) 0.124(6) -0.031(5) 0.069(5) -0.037(5) C18 0.154(6) 0.096(5) 0.153(6) -0.037(5) 0.109(5) -0.008(5) C4 0.085(4) 0.149(7) 0.104(5) -0.053(5) 0.012(4) -0.017(5) C3 0.115(6) 0.141(8) 0.154(8) -0.060(7) 0.056(6) -0.057(6) F7 0.165(5) 0.195(6) 0.179(6) 0.014(5) 0.056(4) 0.073(5) F8 0.273(7) 0.118(4) 0.362(10) 0.087(5) 0.211(7) 0.060(4) B2 0.078(4) 0.075(4) 0.095(5) 0.011(4) 0.021(4) 0.004(3) F4 0.229(6) 0.179(6) 0.321(9) 0.093(6) 0.183(6) 0.056(5) F6 0.371(13) 0.445(17) 0.123(6) 0.038(7) 0.107(7) 0.102(11) F5 0.150(6) 0.319(10) 0.273(10) 0.053(9) 0.031(6) -0.040(6) F2 0.197(7) 0.419(19) 0.52(2) 0.080(16) 0.219(10) 0.103(10) F1 0.442(14) 0.231(9) 0.315(12) 0.063(9) 0.258(12) 0.092(10) B1 0.336(15) 0.133(12) 0.63(4) -0.062(18) 0.41(2) -0.051(14) F3 0.420(18) 0.323(17) 0.80(4) -0.20(2) 0.33(2) -0.170(16) O4 0.182(8) 0.368(16) 0.169(9) -0.001(8) 0.060(6) -0.011(8) O3 0.53(2) 0.329(16) 0.178(9) 0.059(11) 0.144(12) 0.165(17) O2 0.59(2) 0.52(2) 0.306(16) -0.190(16) -0.102(17) 0.44(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 Co O1 2.046(4) . ? Co N1 2.112(4) . ? Co N2 2.126(4) . ? Co N3 2.174(4) . ? Co N4 2.198(4) . ? Co N5 2.215(4) . ? N2 C8 1.327(6) . ? N2 C12 1.347(6) . ? N1 C1 1.327(7) . ? N1 C5 1.346(7) . ? N3 C6 1.457(7) . ? N3 C13 1.474(8) . ? N3 C7 1.476(7) . ? O1 H1A 0.8200 . ? O1 H1D 0.850(18) . ? C12 C11 1.349(8) . ? C12 H12A 0.9300 . ? C8 C9 1.385(8) . ? C8 C7 1.503(7) . ? N4 C15 1.466(7) . ? N4 C14 1.474(7) . ? N4 C21 1.522(6) . ? N5 C16 1.328(7) . ? N5 C20 1.336(7) . ? C21 C22 1.486(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C27 C26 1.366(8) . ? C27 C22 1.405(8) . ? C27 H27A 0.9300 . ? C16 C17 1.373(8) . ? C16 C15 1.542(8) . ? C22 C23 1.367(9) . ? C1 C2 1.371(9) . ? C1 H1B 0.9300 . ? C5 C4 1.396(9) . ? C5 C6 1.513(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C24 C23 1.380(11) . ? C24 C25 1.389(12) . ? C24 H24A 0.9300 . ? C11 C10 1.349(8) . ? C11 H11A 0.9300 . ? C14 C13 1.500(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C23 H23A 0.9300 . ? C19 C18 1.343(10) . ? C19 C20 1.382(8) . ? C19 H19A 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C17 C18 1.388(10) . ? C17 H17A 0.9300 . ? C20 H20A 0.9300 . ? C9 C10 1.363(8) . ? C9 H9A 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C26 C25 1.372(12) . ? C26 H26A 0.9300 . ? C10 H10A 0.9300 . ? C25 H25A 0.9300 . ? C2 C3 1.349(12) . ? C2 H2A 0.9300 . ? C18 H18A 0.9300 . ? C4 C3 1.385(13) . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? F7 B2 1.298(9) . ? F8 B2 1.238(9) . ? B2 F5 1.274(10) . ? B2 F6 1.355(12) . ? F4 B1 1.23(2) . ? F2 B1 1.33(3) . ? F1 B1 1.37(2) . ? B1 F3 1.24(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co N1 101.22(19) . . ? O1 Co N2 93.42(18) . . ? N1 Co N2 100.07(15) . . ? O1 Co N3 171.32(19) . . ? N1 Co N3 77.11(18) . . ? N2 Co N3 78.60(15) . . ? O1 Co N4 103.1(2) . . ? N1 Co N4 148.64(17) . . ? N2 Co N4 97.87(15) . . ? N3 Co N4 81.53(18) . . ? O1 Co N5 84.35(19) . . ? N1 Co N5 87.47(16) . . ? N2 Co N5 172.43(15) . . ? N3 Co N5 104.00(17) . . ? N4 Co N5 75.68(15) . . ? C8 N2 C12 118.0(4) . . ? C8 N2 Co 115.5(3) . . ? C12 N2 Co 126.5(3) . . ? C1 N1 C5 119.5(5) . . ? C1 N1 Co 126.8(4) . . ? C5 N1 Co 113.7(4) . . ? C6 N3 C13 114.3(5) . . ? C6 N3 C7 109.9(5) . . ? C13 N3 C7 110.2(5) . . ? C6 N3 Co 104.8(3) . . ? C13 N3 Co 109.0(4) . . ? C7 N3 Co 108.2(3) . . ? Co O1 H1A 109.5 . . ? Co O1 H1D 126(3) . . ? H1A O1 H1D 121.6 . . ? N2 C12 C11 123.0(5) . . ? N2 C12 H12A 118.5 . . ? C11 C12 H12A 118.5 . . ? N2 C8 C9 121.0(5) . . ? N2 C8 C7 116.9(4) . . ? C9 C8 C7 122.1(5) . . ? C15 N4 C14 111.4(5) . . ? C15 N4 C21 109.6(4) . . ? C14 N4 C21 112.9(4) . . ? C15 N4 Co 107.0(3) . . ? C14 N4 Co 103.9(3) . . ? C21 N4 Co 111.7(3) . . ? C16 N5 C20 117.5(5) . . ? C16 N5 Co 113.8(3) . . ? C20 N5 Co 128.2(4) . . ? C22 C21 N4 116.4(4) . . ? C22 C21 H21A 108.2 . . ? N4 C21 H21A 108.2 . . ? C22 C21 H21B 108.2 . . ? N4 C21 H21B 108.2 . . ? H21A C21 H21B 107.3 . . ? C26 C27 C22 122.0(6) . . ? C26 C27 H27A 119.0 . . ? C22 C27 H27A 119.0 . . ? N5 C16 C17 123.4(5) . . ? N5 C16 C15 116.2(5) . . ? C17 C16 C15 120.2(6) . . ? C23 C22 C27 116.7(6) . . ? C23 C22 C21 122.6(6) . . ? C27 C22 C21 120.7(5) . . ? N1 C1 C2 123.6(6) . . ? N1 C1 H1B 118.2 . . ? C2 C1 H1B 118.2 . . ? N1 C5 C4 120.0(7) . . ? N1 C5 C6 115.8(5) . . ? C4 C5 C6 124.2(6) . . ? N3 C7 C8 111.7(4) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C23 C24 C25 119.9(8) . . ? C23 C24 H24A 120.1 . . ? C25 C24 H24A 120.1 . . ? C12 C11 C10 119.2(5) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? N4 C14 C13 111.5(4) . . ? N4 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? N4 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N4 C15 C16 110.3(5) . . ? N4 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? N4 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C22 C23 C24 122.1(8) . . ? C22 C23 H23A 118.9 . . ? C24 C23 H23A 118.9 . . ? C18 C19 C20 119.9(6) . . ? C18 C19 H19A 120.1 . . ? C20 C19 H19A 120.1 . . ? N3 C13 C14 111.1(5) . . ? N3 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N3 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C16 C17 C18 118.2(6) . . ? C16 C17 H17A 120.9 . . ? C18 C17 H17A 120.9 . . ? N5 C20 C19 122.0(6) . . ? N5 C20 H20A 119.0 . . ? C19 C20 H20A 119.0 . . ? C10 C9 C8 119.6(6) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? N3 C6 C5 109.1(4) . . ? N3 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N3 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C27 C26 C25 120.1(8) . . ? C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C11 C10 C9 119.2(6) . . ? C11 C10 H10A 120.4 . . ? C9 C10 H10A 120.4 . . ? C26 C25 C24 119.1(7) . . ? C26 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C3 C2 C1 117.2(8) . . ? C3 C2 H2A 121.4 . . ? C1 C2 H2A 121.4 . . ? C19 C18 C17 118.8(6) . . ? C19 C18 H18A 120.6 . . ? C17 C18 H18A 120.6 . . ? C3 C4 C5 118.2(7) . . ? C3 C4 H4A 120.9 . . ? C5 C4 H4A 120.9 . . ? C2 C3 C4 121.4(7) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? F8 B2 F5 106.8(8) . . ? F8 B2 F7 113.8(8) . . ? F5 B2 F7 113.7(9) . . ? F8 B2 F6 116.5(10) . . ? F5 B2 F6 99.9(9) . . ? F7 B2 F6 105.4(8) . . ? F4 B1 F3 119.5(19) . . ? F4 B1 F2 112.5(14) . . ? F3 B1 F2 111(3) . . ? F4 B1 F1 118(3) . . ? F3 B1 F1 99.1(14) . . ? F2 B1 F1 92.9(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.712 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 937143' ####################################################################### # # 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_ok _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H31 B2 Co F8 N6' _chemical_formula_weight 708.16 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 11.183(3) _cell_length_b 23.646(7) _cell_length_c 13.366(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.089(4) _cell_angle_gamma 90.00 _cell_volume 3226.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21617 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.60 _reflns_number_total 7473 _reflns_number_gt 5248 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1525P)^2^+1.2834P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7473 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0956 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2419 _refine_ls_wR_factor_gt 0.2182 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.008 _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 Co Co 0.86208(4) 0.62529(2) -0.32587(3) 0.04102(19) Uani 1 1 d . . . N4 N 0.7453(3) 0.69257(12) -0.2914(2) 0.0406(6) Uani 1 1 d . . . N1 N 0.8954(3) 0.66564(13) -0.4536(2) 0.0447(7) Uani 1 1 d . . . N5 N 0.8048(3) 0.58658(13) -0.2058(2) 0.0489(7) Uani 1 1 d . . . N6 N 0.6878(3) 0.58583(15) -0.4497(3) 0.0571(8) Uani 1 1 d . . . N2 N 0.9915(3) 0.55698(14) -0.3143(2) 0.0494(7) Uani 1 1 d . . . C7 C 1.1409(4) 0.6155(2) -0.1695(4) 0.0731(14) Uani 1 1 d . . . H7A H 1.2319 0.6265 -0.1454 0.088 Uiso 1 1 calc R . . H7B H 1.1256 0.6064 -0.1049 0.088 Uiso 1 1 calc R . . N3 N 1.0556(3) 0.66389(14) -0.2278(2) 0.0516(7) Uani 1 1 d . . . C15 C 0.8231(4) 0.72518(16) -0.1892(3) 0.0493(8) Uani 1 1 d . . . H15A H 0.8416 0.7007 -0.1265 0.059 Uiso 1 1 calc R . . H15B H 0.7700 0.7563 -0.1831 0.059 Uiso 1 1 calc R . . C26 C 0.4375(7) 0.8660(2) -0.3630(5) 0.0775(15) Uani 1 1 d . . . H26A H 0.3846 0.8951 -0.3574 0.093 Uiso 1 1 calc R . . C22 C 0.6835(4) 0.73154(15) -0.3877(3) 0.0438(8) Uani 1 1 d . . . H22A H 0.6311 0.7089 -0.4510 0.053 Uiso 1 1 calc R . . H22B H 0.7528 0.7488 -0.4031 0.053 Uiso 1 1 calc R . . C23 C 0.5976(4) 0.77822(14) -0.3758(3) 0.0454(8) Uani 1 1 d . . . C8 C 1.1165(4) 0.56446(19) -0.2393(3) 0.0573(10) Uani 1 1 d . . . C5 C 1.0134(4) 0.68972(16) -0.4232(3) 0.0507(9) Uani 1 1 d . . . C14 C 0.9512(4) 0.74863(17) -0.1846(3) 0.0563(10) Uani 1 1 d . . . H14A H 0.9390 0.7611 -0.2573 0.068 Uiso 1 1 calc R . . H14B H 0.9755 0.7814 -0.1367 0.068 Uiso 1 1 calc R . . C16 C 0.6424(4) 0.66137(15) -0.2724(3) 0.0464(8) Uani 1 1 d . . . H16A H 0.5749 0.6498 -0.3423 0.056 Uiso 1 1 calc R . . H16B H 0.6025 0.6861 -0.2368 0.056 Uiso 1 1 calc R . . C17 C 0.6970(4) 0.60980(16) -0.2020(3) 0.0473(8) Uani 1 1 d . . . C21 C 0.8524(5) 0.53871(19) -0.1484(4) 0.0653(11) Uani 1 1 d . . . H21A H 0.9275 0.5226 -0.1500 0.078 Uiso 1 1 calc R . . C1 C 0.8146(4) 0.66641(17) -0.5615(3) 0.0510(8) Uani 1 1 d . . . H1A H 0.7311 0.6512 -0.5831 0.061 Uiso 1 1 calc R . . C24 C 0.4642(4) 0.77042(17) -0.4061(3) 0.0520(9) Uani 1 1 d . . . H24A H 0.4276 0.7350 -0.4306 0.062 Uiso 1 1 calc R . . C9 C 1.2121(4) 0.5243(2) -0.2246(4) 0.0712(12) Uani 1 1 d . . . H9A H 1.2974 0.5303 -0.1736 0.085 Uiso 1 1 calc R . . C10 C 1.1806(5) 0.4753(2) -0.2854(4) 0.0740(13) Uani 1 1 d . . . H10A H 1.2436 0.4477 -0.2757 0.089 Uiso 1 1 calc R . . C13 C 1.0610(4) 0.70603(18) -0.1437(3) 0.0567(10) Uani 1 1 d . . . H13A H 1.1439 0.7259 -0.1188 0.068 Uiso 1 1 calc R . . H13B H 1.0578 0.6863 -0.0812 0.068 Uiso 1 1 calc R . . C12 C 0.9635(4) 0.50906(17) -0.3736(3) 0.0544(9) Uani 1 1 d . . . H12A H 0.8785 0.5034 -0.4256 0.065 Uiso 1 1 calc R . . C29 C 0.5985(4) 0.57054(18) -0.5246(3) 0.0592(10) Uani 1 1 d . . . C18 C 0.6372(5) 0.5871(2) -0.1389(4) 0.0632(11) Uani 1 1 d . . . H18A H 0.5660 0.6053 -0.1340 0.076 Uiso 1 1 calc R . . C11 C 1.0554(5) 0.4683(2) -0.3600(4) 0.0678(12) Uani 1 1 d . . . H11A H 1.0321 0.4356 -0.4021 0.081 Uiso 1 1 calc R . . C27 C 0.5674(7) 0.87494(19) -0.3339(5) 0.0838(16) Uani 1 1 d . . . H27A H 0.6024 0.9106 -0.3098 0.101 Uiso 1 1 calc R . . C28 C 0.6500(5) 0.83129(18) -0.3395(4) 0.0668(11) Uani 1 1 d . . . H28A H 0.7388 0.8380 -0.3192 0.080 Uiso 1 1 calc R . . C4 C 1.0524(5) 0.7133(2) -0.4998(4) 0.0800(15) Uani 1 1 d . . . H4A H 1.1342 0.7304 -0.4772 0.096 Uiso 1 1 calc R . . C25 C 0.3847(5) 0.8138(2) -0.4007(4) 0.0656(11) Uani 1 1 d . . . H25A H 0.2954 0.8078 -0.4226 0.079 Uiso 1 1 calc R . . C20 C 0.7943(6) 0.5129(2) -0.0879(4) 0.0756(13) Uani 1 1 d . . . H20A H 0.8283 0.4794 -0.0504 0.091 Uiso 1 1 calc R . . C2 C 0.8495(5) 0.6882(2) -0.6395(3) 0.0662(11) Uani 1 1 d . . . H2A H 0.7915 0.6873 -0.7129 0.079 Uiso 1 1 calc R . . C19 C 0.6839(5) 0.5375(2) -0.0834(4) 0.0758(14) Uani 1 1 d . . . H19A H 0.6422 0.5206 -0.0435 0.091 Uiso 1 1 calc R . . C3 C 0.9709(7) 0.7115(3) -0.6087(5) 0.0923(18) Uani 1 1 d . . . H3A H 0.9978 0.7259 -0.6609 0.111 Uiso 1 1 calc R . . C6 C 1.1045(5) 0.6899(3) -0.3051(4) 0.0739(14) Uani 1 1 d . . . H6A H 1.1839 0.6703 -0.2976 0.089 Uiso 1 1 calc R . . H6B H 1.1282 0.7288 -0.2829 0.089 Uiso 1 1 calc R . . C30 C 0.4846(5) 0.5520(3) -0.6217(4) 0.0861(16) Uani 1 1 d . . . F4 F 0.1551(4) 1.1358(2) -0.1539(5) 0.148(2) Uani 1 1 d . . . F3 F 0.1626(6) 1.1404(2) 0.0103(4) 0.1522(19) Uani 1 1 d . . . F2 F 0.3158(4) 1.0923(3) -0.0302(5) 0.169(2) Uani 1 1 d . . . F8 F 0.3944(6) 0.6629(5) 0.0686(6) 0.288(6) Uani 1 1 d . . . F1 F 0.1166(7) 1.0606(2) -0.0756(7) 0.205(3) Uani 1 1 d . . . B2 B 0.4941(6) 0.6281(3) 0.0969(6) 0.0744(15) Uani 1 1 d . . . F7 F 0.5396(10) 0.6315(4) 0.2016(6) 0.267(5) Uani 1 1 d . . . F6 F 0.5754(13) 0.6484(4) 0.0676(12) 0.328(7) Uani 1 1 d . . . F5 F 0.4721(11) 0.5815(3) 0.0529(9) 0.280(5) Uani 1 1 d . . . B1 B 0.1886(7) 1.1060(3) -0.0616(9) 0.100(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0385(3) 0.0477(3) 0.0348(3) -0.00214(17) 0.0129(2) -0.00115(18) N4 0.0432(16) 0.0446(14) 0.0326(13) 0.0023(11) 0.0142(11) -0.0011(12) N1 0.0471(17) 0.0502(16) 0.0388(14) -0.0064(12) 0.0196(12) 0.0015(13) N5 0.0580(19) 0.0456(16) 0.0462(16) 0.0076(12) 0.0243(14) 0.0031(14) N6 0.053(2) 0.0579(19) 0.0574(19) -0.0061(15) 0.0191(16) -0.0073(15) N2 0.0445(17) 0.0572(18) 0.0455(15) -0.0018(13) 0.0173(13) 0.0041(14) C7 0.049(3) 0.085(3) 0.060(3) -0.016(2) -0.003(2) 0.011(2) N3 0.0472(18) 0.0638(19) 0.0386(14) -0.0118(13) 0.0122(13) -0.0081(15) C15 0.059(2) 0.0509(19) 0.0345(16) -0.0038(14) 0.0149(15) 0.0004(16) C26 0.097(4) 0.062(3) 0.079(3) 0.007(2) 0.042(3) 0.031(3) C22 0.051(2) 0.0473(18) 0.0331(15) 0.0046(13) 0.0174(14) 0.0058(15) C23 0.058(2) 0.0435(17) 0.0349(15) 0.0061(13) 0.0191(15) 0.0052(15) C8 0.041(2) 0.072(3) 0.053(2) -0.0034(18) 0.0127(17) 0.0043(18) C5 0.053(2) 0.0485(19) 0.057(2) -0.0094(16) 0.0298(18) -0.0064(16) C14 0.062(2) 0.053(2) 0.0442(19) -0.0107(16) 0.0118(17) -0.0113(18) C16 0.0435(19) 0.0500(19) 0.0479(18) 0.0050(15) 0.0210(15) 0.0028(15) C17 0.048(2) 0.0484(18) 0.0447(18) 0.0043(14) 0.0185(15) -0.0024(16) C21 0.074(3) 0.059(2) 0.066(3) 0.0177(19) 0.032(2) 0.013(2) C1 0.053(2) 0.056(2) 0.0456(18) 0.0022(15) 0.0214(16) 0.0070(17) C24 0.061(2) 0.052(2) 0.0423(17) 0.0033(15) 0.0202(17) 0.0090(17) C9 0.047(2) 0.082(3) 0.073(3) -0.001(2) 0.013(2) 0.009(2) C10 0.061(3) 0.073(3) 0.088(3) 0.004(3) 0.030(3) 0.015(2) C13 0.054(2) 0.067(2) 0.0392(17) -0.0150(17) 0.0088(16) -0.0093(19) C12 0.049(2) 0.058(2) 0.054(2) -0.0020(17) 0.0199(17) 0.0006(17) C29 0.062(3) 0.061(2) 0.052(2) -0.0009(18) 0.021(2) -0.0067(19) C18 0.065(3) 0.071(3) 0.063(2) 0.012(2) 0.037(2) -0.002(2) C11 0.073(3) 0.057(2) 0.074(3) -0.002(2) 0.031(2) 0.007(2) C27 0.117(5) 0.043(2) 0.091(4) -0.001(2) 0.042(4) 0.008(2) C28 0.078(3) 0.050(2) 0.074(3) 0.005(2) 0.033(2) -0.002(2) C4 0.076(3) 0.099(4) 0.074(3) -0.004(3) 0.040(3) -0.028(3) C25 0.068(3) 0.079(3) 0.055(2) 0.006(2) 0.030(2) 0.018(2) C20 0.101(4) 0.060(3) 0.070(3) 0.026(2) 0.040(3) 0.010(3) C2 0.079(3) 0.076(3) 0.048(2) 0.0105(19) 0.030(2) 0.007(2) C19 0.085(4) 0.081(3) 0.070(3) 0.024(2) 0.041(3) -0.007(3) C3 0.113(5) 0.107(4) 0.071(3) 0.013(3) 0.052(3) -0.021(4) C6 0.051(3) 0.111(4) 0.060(2) -0.021(2) 0.024(2) -0.028(3) C30 0.069(3) 0.102(4) 0.065(3) -0.014(3) 0.004(2) -0.016(3) F4 0.091(3) 0.186(5) 0.180(5) 0.060(4) 0.067(3) 0.035(3) F3 0.215(6) 0.108(3) 0.136(4) 0.015(3) 0.073(4) 0.008(4) F2 0.093(3) 0.170(5) 0.225(6) 0.082(4) 0.046(3) 0.046(3) F8 0.130(5) 0.507(15) 0.186(7) -0.102(8) 0.022(4) 0.120(7) F1 0.236(7) 0.150(5) 0.298(8) -0.055(5) 0.181(7) -0.084(5) B2 0.058(3) 0.094(4) 0.072(3) -0.009(3) 0.027(3) -0.010(3) F7 0.305(11) 0.340(12) 0.128(5) 0.007(6) 0.061(6) 0.095(8) F6 0.436(15) 0.230(8) 0.525(19) -0.005(10) 0.406(16) -0.031(9) F5 0.352(11) 0.127(5) 0.362(13) -0.091(7) 0.146(10) -0.085(6) B1 0.071(4) 0.075(4) 0.159(8) 0.026(5) 0.052(5) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co N1 2.117(3) . ? Co N2 2.132(3) . ? Co N5 2.159(3) . ? Co N6 2.185(3) . ? Co N3 2.218(3) . ? Co N4 2.223(3) . ? N4 C16 1.473(4) . ? N4 C15 1.499(4) . ? N4 C22 1.503(4) . ? N1 C5 1.339(5) . ? N1 C1 1.354(5) . ? N5 C17 1.344(5) . ? N5 C21 1.349(5) . ? N6 C29 1.147(5) . ? N2 C12 1.344(5) . ? N2 C8 1.359(5) . ? C7 C8 1.481(6) . ? C7 N3 1.490(6) . ? N3 C13 1.485(5) . ? N3 C6 1.487(6) . ? C15 C14 1.513(6) . ? C26 C27 1.358(9) . ? C26 C25 1.371(7) . ? C22 C23 1.513(5) . ? C23 C28 1.386(6) . ? C23 C24 1.389(6) . ? C8 C9 1.383(6) . ? C5 C4 1.384(6) . ? C5 C6 1.488(6) . ? C14 C13 1.508(6) . ? C16 C17 1.509(5) . ? C17 C18 1.382(5) . ? C21 C20 1.371(6) . ? C1 C2 1.355(6) . ? C24 C25 1.380(6) . ? C9 C10 1.375(7) . ? C10 C11 1.357(7) . ? C12 C11 1.366(6) . ? C29 C30 1.466(6) . ? C18 C19 1.373(7) . ? C27 C28 1.408(7) . ? C4 C3 1.367(8) . ? C20 C19 1.389(7) . ? C2 C3 1.363(8) . ? F4 B1 1.335(10) . ? F3 B1 1.378(11) . ? F2 B1 1.348(8) . ? F8 B2 1.311(10) . ? F1 B1 1.308(8) . ? B2 F5 1.225(9) . ? B2 F6 1.226(9) . ? B2 F7 1.281(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co N2 93.55(12) . . ? N1 Co N5 173.47(12) . . ? N2 Co N5 91.35(12) . . ? N1 Co N6 88.73(12) . . ? N2 Co N6 95.77(13) . . ? N5 Co N6 86.49(13) . . ? N1 Co N3 80.85(12) . . ? N2 Co N3 78.42(12) . . ? N5 Co N3 104.39(12) . . ? N6 Co N3 167.66(12) . . ? N1 Co N4 99.00(11) . . ? N2 Co N4 165.08(11) . . ? N5 Co N4 76.80(11) . . ? N6 Co N4 92.56(12) . . ? N3 Co N4 95.57(11) . . ? C16 N4 C15 107.7(3) . . ? C16 N4 C22 109.7(3) . . ? C15 N4 C22 111.0(3) . . ? C16 N4 Co 104.1(2) . . ? C15 N4 Co 112.7(2) . . ? C22 N4 Co 111.41(19) . . ? C5 N1 C1 117.7(3) . . ? C5 N1 Co 115.0(2) . . ? C1 N1 Co 127.2(3) . . ? C17 N5 C21 118.2(3) . . ? C17 N5 Co 113.4(2) . . ? C21 N5 Co 127.6(3) . . ? C29 N6 Co 170.4(4) . . ? C12 N2 C8 117.8(3) . . ? C12 N2 Co 127.4(3) . . ? C8 N2 Co 114.7(3) . . ? C8 C7 N3 112.5(3) . . ? C13 N3 C6 109.6(3) . . ? C13 N3 C7 107.5(3) . . ? C6 N3 C7 110.0(4) . . ? C13 N3 Co 116.9(2) . . ? C6 N3 Co 107.8(2) . . ? C7 N3 Co 104.8(3) . . ? N4 C15 C14 114.4(3) . . ? C27 C26 C25 119.7(4) . . ? N4 C22 C23 116.5(3) . . ? C28 C23 C24 118.2(4) . . ? C28 C23 C22 120.1(4) . . ? C24 C23 C22 121.6(3) . . ? N2 C8 C9 121.2(4) . . ? N2 C8 C7 116.1(4) . . ? C9 C8 C7 122.5(4) . . ? N1 C5 C4 121.1(4) . . ? N1 C5 C6 119.1(3) . . ? C4 C5 C6 119.8(4) . . ? C13 C14 C15 112.8(3) . . ? N4 C16 C17 111.5(3) . . ? N5 C17 C18 122.0(4) . . ? N5 C17 C16 116.6(3) . . ? C18 C17 C16 121.4(4) . . ? N5 C21 C20 122.5(4) . . ? N1 C1 C2 123.2(4) . . ? C25 C24 C23 121.6(4) . . ? C10 C9 C8 119.8(4) . . ? C11 C10 C9 118.4(4) . . ? N3 C13 C14 113.5(3) . . ? N2 C12 C11 122.3(4) . . ? N6 C29 C30 178.8(5) . . ? C19 C18 C17 119.3(4) . . ? C10 C11 C12 120.5(5) . . ? C26 C27 C28 121.3(5) . . ? C23 C28 C27 119.3(5) . . ? C3 C4 C5 120.0(5) . . ? C26 C25 C24 119.9(5) . . ? C21 C20 C19 118.9(4) . . ? C1 C2 C3 119.0(4) . . ? C18 C19 C20 119.0(4) . . ? C2 C3 C4 118.9(5) . . ? N3 C6 C5 116.7(3) . . ? F5 B2 F6 103.2(8) . . ? F5 B2 F7 119.6(9) . . ? F6 B2 F7 108.0(10) . . ? F5 B2 F8 116.4(8) . . ? F6 B2 F8 108.4(9) . . ? F7 B2 F8 100.9(7) . . ? F1 B1 F4 112.1(9) . . ? F1 B1 F2 110.9(7) . . ? F4 B1 F2 106.1(6) . . ? F1 B1 F3 107.0(7) . . ? F4 B1 F3 105.8(6) . . ? F2 B1 F3 114.9(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.117 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 937144' ####################################################################### # # 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_sr _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H33 B2 Co F8 N5 O' _chemical_formula_weight 688.14 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 11.2389(6) _cell_length_b 23.3087(13) _cell_length_c 13.5001(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.129(3) _cell_angle_gamma 90.00 _cell_volume 3276.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5774 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5774 _reflns_number_gt 4486 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1317P)^2^+1.4168P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5774 _refine_ls_number_parameters 423 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1961 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 Co Co 0.35547(4) 0.12684(2) 0.19742(4) 0.0491(2) Uani 1 1 d . . . N1 N 0.3829(3) 0.16423(12) 0.0641(2) 0.0511(7) Uani 1 1 d . . . N4 N 0.2387(3) 0.19596(12) 0.2296(2) 0.0499(7) Uani 1 1 d . . . N5 N 0.3052(3) 0.09136(13) 0.3228(3) 0.0575(8) Uani 1 1 d . . . N3 N 0.5419(3) 0.16843(13) 0.2811(2) 0.0547(7) Uani 1 1 d . . . C17 C 0.1970(4) 0.11382(17) 0.3265(3) 0.0575(9) Uani 1 1 d . . . O1 O 0.1942(3) 0.07928(15) 0.0969(3) 0.0775(9) Uani 1 1 d D . . N2 N 0.4878(3) 0.05935(14) 0.2013(3) 0.0605(8) Uani 1 1 d . . . C23 C 0.0872(4) 0.27872(16) 0.1378(3) 0.0538(9) Uani 1 1 d . . . C14 C 0.4396(4) 0.25537(17) 0.3250(4) 0.0676(11) Uani 1 1 d . . . H14A H 0.4287 0.2678 0.2535 0.081 Uiso 1 1 calc R . . H14B H 0.4639 0.2886 0.3716 0.081 Uiso 1 1 calc R . . C5 C 0.4954(4) 0.18860(16) 0.0857(3) 0.0566(9) Uani 1 1 d . . . C28 C -0.0440(4) 0.26768(18) 0.1117(3) 0.0625(10) Uani 1 1 d . . . H28A H -0.0753 0.2307 0.0929 0.075 Uiso 1 1 calc R . . C22 C 0.1766(4) 0.23172(16) 0.1313(3) 0.0535(9) Uani 1 1 d . . . H22A H 0.1287 0.2063 0.0730 0.064 Uiso 1 1 calc R . . H22B H 0.2440 0.2492 0.1130 0.064 Uiso 1 1 calc R . . C16 C 0.1401(4) 0.16460(17) 0.2559(3) 0.0592(10) Uani 1 1 d . . . H16A H 0.0729 0.1516 0.1904 0.071 Uiso 1 1 calc R . . H16B H 0.1015 0.1903 0.2919 0.071 Uiso 1 1 calc R . . C8 C 0.6106(4) 0.06895(18) 0.2675(4) 0.0627(10) Uani 1 1 d . . . C15 C 0.3115(4) 0.23214(17) 0.3234(3) 0.0609(10) Uani 1 1 d . . . H15A H 0.3279 0.2098 0.3878 0.073 Uiso 1 1 calc R . . H15B H 0.2579 0.2644 0.3255 0.073 Uiso 1 1 calc R . . C1 C 0.3030(4) 0.15935(18) -0.0390(3) 0.0598(10) Uani 1 1 d . . . H1B H 0.2239 0.1416 -0.0545 0.072 Uiso 1 1 calc R . . C2 C 0.3329(5) 0.1793(2) -0.1214(3) 0.0738(12) Uani 1 1 d . . . H2A H 0.2739 0.1767 -0.1915 0.089 Uiso 1 1 calc R . . C7 C 0.6309(4) 0.12134(19) 0.3374(4) 0.0695(12) Uani 1 1 d . . . H7A H 0.6171 0.1114 0.4021 0.083 Uiso 1 1 calc R . . H7B H 0.7189 0.1344 0.3580 0.083 Uiso 1 1 calc R . . C21 C 0.3526(5) 0.04274(18) 0.3797(4) 0.0710(12) Uani 1 1 d . . . H21A H 0.4277 0.0271 0.3777 0.085 Uiso 1 1 calc R . . C18 C 0.1353(5) 0.0895(2) 0.3894(4) 0.0755(12) Uani 1 1 d . . . H18A H 0.0626 0.1068 0.3934 0.091 Uiso 1 1 calc R . . C13 C 0.5469(4) 0.21140(18) 0.3632(3) 0.0639(10) Uani 1 1 d . . . H13A H 0.6287 0.2312 0.3857 0.077 Uiso 1 1 calc R . . H13B H 0.5427 0.1916 0.4250 0.077 Uiso 1 1 calc R . . C27 C -0.1270(5) 0.3105(2) 0.1136(4) 0.0738(12) Uani 1 1 d . . . H27A H -0.2137 0.3025 0.0953 0.089 Uiso 1 1 calc R . . C25 C 0.0420(7) 0.37679(19) 0.1676(5) 0.0919(17) Uani 1 1 d . . . H25A H 0.0716 0.4139 0.1873 0.110 Uiso 1 1 calc R . . C12 C 0.4629(5) 0.01213(18) 0.1402(4) 0.0696(11) Uani 1 1 d . . . H12A H 0.3789 0.0055 0.0932 0.084 Uiso 1 1 calc R . . C20 C 0.2948(5) 0.0159(2) 0.4396(4) 0.0841(15) Uani 1 1 d . . . H20A H 0.3285 -0.0179 0.4762 0.101 Uiso 1 1 calc R . . C26 C -0.0824(6) 0.3651(2) 0.1424(4) 0.0846(15) Uani 1 1 d . . . H26A H -0.1385 0.3940 0.1444 0.102 Uiso 1 1 calc R . . C24 C 0.1290(5) 0.33394(18) 0.1651(4) 0.0734(12) Uani 1 1 d . . . H24A H 0.2149 0.3431 0.1818 0.088 Uiso 1 1 calc R . . C9 C 0.7067(5) 0.0310(2) 0.2754(5) 0.0845(14) Uani 1 1 d . . . H9A H 0.7901 0.0378 0.3232 0.101 Uiso 1 1 calc R . . C4 C 0.5329(6) 0.2083(3) 0.0045(4) 0.0963(17) Uani 1 1 d . . . H4A H 0.6133 0.2250 0.0213 0.116 Uiso 1 1 calc R . . C6 C 0.5855(4) 0.1947(2) 0.1994(3) 0.0668(11) Uani 1 1 d . . . H6A H 0.6006 0.2353 0.2152 0.080 Uiso 1 1 calc R . . H6B H 0.6670 0.1776 0.2067 0.080 Uiso 1 1 calc R . . C11 C 0.5541(5) -0.0261(2) 0.1437(5) 0.0839(14) Uani 1 1 d . . . H11A H 0.5330 -0.0584 0.1000 0.101 Uiso 1 1 calc R . . C19 C 0.1831(5) 0.0405(2) 0.4446(4) 0.0867(15) Uani 1 1 d . . . H19A H 0.1421 0.0233 0.4853 0.104 Uiso 1 1 calc R . . C10 C 0.6799(5) -0.0169(2) 0.2130(5) 0.0906(15) Uani 1 1 d . . . H10A H 0.7444 -0.0428 0.2168 0.109 Uiso 1 1 calc R . . C3 C 0.4518(7) 0.2032(3) -0.0993(4) 0.108(2) Uani 1 1 d . . . H3A H 0.4764 0.2156 -0.1543 0.130 Uiso 1 1 calc R . . F4 F -0.1696(5) 0.1353(3) 0.1496(6) 0.182(2) Uani 1 1 d . . . F8 F -0.5634(6) 0.4088(3) 0.0226(5) 0.176(2) Uani 1 1 d . . . F6 F -0.4180(6) 0.3498(4) 0.1333(7) 0.247(4) Uani 1 1 d . . . F3 F -0.1506(12) 0.1335(3) 0.0007(6) 0.284(6) Uani 1 1 d . . . B2 B -0.5245(8) 0.3758(3) 0.1051(6) 0.100(2) Uani 1 1 d . A . F2 F -0.3064(8) 0.0839(3) 0.0356(7) 0.294(5) Uani 1 1 d . . . F5 F -0.5665(13) 0.3933(4) 0.1820(10) 0.314(5) Uani 1 1 d . . . F1 F -0.1076(10) 0.0606(4) 0.1012(10) 0.300(6) Uani 1 1 d . . . B1 B -0.1907(12) 0.1035(4) 0.0649(14) 0.152(4) Uani 1 1 d . . . F7A F -0.4443(16) 0.4273(8) 0.1383(17) 0.278(10) Uani 0.50 1 d P A 1 F7B F -0.6134(7) 0.3301(3) 0.0749(7) 0.117(2) Uani 0.50 1 d P A 2 H1 H 0.183(6) 0.0491(17) 0.129(4) 0.12(2) Uiso 1 1 d D . . H2 H 0.178(8) 0.076(3) 0.031(2) 0.18(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0514(3) 0.0495(3) 0.0407(3) -0.00085(19) 0.0108(2) -0.0030(2) N1 0.0600(18) 0.0531(17) 0.0378(15) -0.0043(13) 0.0155(13) 0.0040(14) N4 0.0587(17) 0.0484(16) 0.0403(16) 0.0067(12) 0.0159(13) 0.0004(13) N5 0.0600(19) 0.0533(18) 0.0549(19) 0.0121(14) 0.0166(15) -0.0002(14) N3 0.0574(17) 0.0588(18) 0.0413(16) -0.0016(13) 0.0109(14) -0.0075(14) C17 0.064(2) 0.055(2) 0.051(2) 0.0085(17) 0.0193(18) -0.0078(18) O1 0.073(2) 0.079(2) 0.070(2) -0.0147(17) 0.0156(17) -0.0176(16) N2 0.0605(19) 0.0604(19) 0.0554(19) -0.0005(15) 0.0160(16) 0.0005(15) C23 0.070(2) 0.053(2) 0.0383(19) 0.0077(15) 0.0199(17) 0.0084(17) C14 0.086(3) 0.056(2) 0.052(2) -0.0095(18) 0.015(2) -0.016(2) C5 0.070(2) 0.053(2) 0.049(2) -0.0046(17) 0.0251(19) -0.0083(18) C28 0.072(3) 0.063(2) 0.043(2) 0.0039(17) 0.0122(18) 0.007(2) C22 0.068(2) 0.052(2) 0.0388(19) 0.0064(15) 0.0177(17) 0.0057(17) C16 0.060(2) 0.065(2) 0.053(2) 0.0126(18) 0.0215(18) 0.0042(18) C8 0.059(2) 0.064(2) 0.061(2) 0.0099(19) 0.0183(19) 0.0055(19) C15 0.080(3) 0.060(2) 0.038(2) 0.0006(16) 0.0178(18) 0.003(2) C1 0.058(2) 0.070(3) 0.044(2) -0.0069(18) 0.0107(17) 0.0096(18) C2 0.096(3) 0.080(3) 0.039(2) 0.002(2) 0.018(2) 0.005(3) C7 0.061(2) 0.079(3) 0.053(2) -0.002(2) 0.0025(19) -0.001(2) C21 0.074(3) 0.058(2) 0.077(3) 0.017(2) 0.023(2) 0.005(2) C18 0.072(3) 0.085(3) 0.074(3) 0.014(2) 0.032(2) -0.004(2) C13 0.069(2) 0.074(3) 0.039(2) -0.0125(18) 0.0092(18) -0.016(2) C27 0.081(3) 0.083(3) 0.055(3) 0.007(2) 0.023(2) 0.020(2) C25 0.124(5) 0.048(3) 0.102(4) 0.003(2) 0.042(4) 0.008(3) C12 0.078(3) 0.053(2) 0.073(3) -0.003(2) 0.023(2) -0.003(2) C20 0.106(4) 0.058(3) 0.083(3) 0.029(2) 0.029(3) -0.001(2) C26 0.098(4) 0.078(3) 0.077(3) 0.007(2) 0.032(3) 0.032(3) C24 0.085(3) 0.052(2) 0.085(3) 0.004(2) 0.034(3) -0.001(2) C9 0.070(3) 0.088(3) 0.090(4) 0.012(3) 0.024(3) 0.013(3) C4 0.116(4) 0.114(4) 0.063(3) -0.005(3) 0.039(3) -0.045(3) C6 0.067(2) 0.081(3) 0.051(2) -0.004(2) 0.0207(19) -0.022(2) C11 0.102(4) 0.059(3) 0.093(4) 0.000(2) 0.040(3) 0.006(3) C19 0.094(4) 0.085(3) 0.083(3) 0.027(3) 0.036(3) -0.018(3) C10 0.090(4) 0.072(3) 0.112(4) 0.007(3) 0.039(3) 0.018(3) C3 0.150(5) 0.127(5) 0.054(3) 0.000(3) 0.046(3) -0.043(4) F4 0.127(4) 0.193(5) 0.227(7) -0.052(5) 0.068(4) -0.057(3) F8 0.185(5) 0.185(5) 0.168(5) 0.068(4) 0.079(4) 0.050(4) F6 0.147(5) 0.245(7) 0.298(10) 0.078(7) 0.024(5) 0.084(5) F3 0.512(17) 0.190(6) 0.160(6) -0.021(5) 0.136(8) -0.137(8) B2 0.095(5) 0.121(6) 0.088(5) 0.046(4) 0.040(4) 0.028(4) F2 0.264(8) 0.234(7) 0.250(8) 0.003(6) -0.057(7) -0.148(7) F5 0.462(15) 0.309(10) 0.311(11) 0.004(9) 0.306(12) -0.016(11) F1 0.362(12) 0.197(6) 0.434(16) 0.105(9) 0.256(13) 0.110(8) B1 0.148(9) 0.083(6) 0.204(13) -0.028(7) 0.040(9) -0.036(6) F7A 0.218(15) 0.238(16) 0.31(2) -0.021(15) 0.020(16) -0.094(14) F7B 0.114(5) 0.115(5) 0.120(6) 0.015(4) 0.044(4) -0.038(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co O1 2.122(3) . ? Co N1 2.125(3) . ? Co N5 2.142(3) . ? Co N2 2.151(3) . ? Co N3 2.196(3) . ? Co N4 2.222(3) . ? N1 C5 1.314(5) . ? N1 C1 1.347(5) . ? N4 C16 1.478(5) . ? N4 C15 1.484(5) . ? N4 C22 1.499(4) . ? N5 C17 1.342(5) . ? N5 C21 1.360(5) . ? N3 C13 1.479(5) . ? N3 C7 1.487(5) . ? N3 C6 1.497(5) . ? C17 C18 1.402(6) . ? C17 C16 1.503(5) . ? O1 H1 0.858(19) . ? O1 H2 0.84(2) . ? N2 C12 1.341(5) . ? N2 C8 1.351(5) . ? C23 C24 1.372(6) . ? C23 C28 1.405(6) . ? C23 C22 1.512(5) . ? C14 C13 1.517(6) . ? C14 C15 1.531(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C5 C4 1.393(6) . ? C5 C6 1.493(6) . ? C28 C27 1.373(6) . ? C28 H28A 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C8 C9 1.370(6) . ? C8 C7 1.507(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C1 C2 1.360(6) . ? C1 H1B 0.9300 . ? C2 C3 1.373(8) . ? C2 H2A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C21 C20 1.365(7) . ? C21 H21A 0.9300 . ? C18 C19 1.360(7) . ? C18 H18A 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C27 C26 1.369(7) . ? C27 H27A 0.9300 . ? C25 C26 1.335(8) . ? C25 C24 1.408(7) . ? C25 H25A 0.9300 . ? C12 C11 1.347(6) . ? C12 H12A 0.9300 . ? C20 C19 1.405(7) . ? C20 H20A 0.9300 . ? C26 H26A 0.9300 . ? C24 H24A 0.9300 . ? C9 C10 1.362(8) . ? C9 H9A 0.9300 . ? C4 C3 1.359(8) . ? C4 H4A 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C11 C10 1.386(8) . ? C11 H11A 0.9300 . ? C19 H19A 0.9300 . ? C10 H10A 0.9300 . ? C3 H3A 0.9300 . ? F4 B1 1.307(14) . ? F8 B2 1.288(8) . ? F8 F7A 1.685(17) . ? F6 B2 1.265(9) . ? F3 B1 1.318(15) . ? B2 F5 1.354(11) . ? B2 F7B 1.411(11) . ? B2 F7A 1.466(16) . ? F2 B1 1.292(12) . ? F1 B1 1.331(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co N1 91.97(14) . . ? O1 Co N5 83.52(15) . . ? N1 Co N5 173.51(12) . . ? O1 Co N2 92.85(13) . . ? N1 Co N2 90.07(12) . . ? N5 Co N2 94.80(13) . . ? O1 Co N3 168.32(14) . . ? N1 Co N3 80.80(12) . . ? N5 Co N3 104.38(12) . . ? N2 Co N3 78.09(12) . . ? O1 Co N4 94.51(13) . . ? N1 Co N4 98.83(11) . . ? N5 Co N4 76.95(11) . . ? N2 Co N4 168.23(12) . . ? N3 Co N4 95.66(12) . . ? C5 N1 C1 118.5(3) . . ? C5 N1 Co 115.0(2) . . ? C1 N1 Co 126.0(3) . . ? C16 N4 C15 107.4(3) . . ? C16 N4 C22 110.3(3) . . ? C15 N4 C22 111.3(3) . . ? C16 N4 Co 103.9(2) . . ? C15 N4 Co 113.7(2) . . ? C22 N4 Co 110.0(2) . . ? C17 N5 C21 118.1(4) . . ? C17 N5 Co 113.0(2) . . ? C21 N5 Co 127.2(3) . . ? C13 N3 C7 106.8(3) . . ? C13 N3 C6 110.1(3) . . ? C7 N3 C6 109.6(4) . . ? C13 N3 Co 116.4(2) . . ? C7 N3 Co 105.4(2) . . ? C6 N3 Co 108.4(2) . . ? N5 C17 C18 121.8(4) . . ? N5 C17 C16 117.3(3) . . ? C18 C17 C16 120.8(4) . . ? Co O1 H1 111(4) . . ? Co O1 H2 121(5) . . ? H1 O1 H2 117(4) . . ? C12 N2 C8 117.9(4) . . ? C12 N2 Co 127.1(3) . . ? C8 N2 Co 114.8(3) . . ? C24 C23 C28 117.4(4) . . ? C24 C23 C22 121.8(4) . . ? C28 C23 C22 120.7(3) . . ? C13 C14 C15 112.9(3) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N1 C5 C4 121.2(4) . . ? N1 C5 C6 119.6(3) . . ? C4 C5 C6 119.2(4) . . ? C27 C28 C23 121.2(4) . . ? C27 C28 H28A 119.4 . . ? C23 C28 H28A 119.4 . . ? N4 C22 C23 116.7(3) . . ? N4 C22 H22A 108.1 . . ? C23 C22 H22A 108.1 . . ? N4 C22 H22B 108.1 . . ? C23 C22 H22B 108.1 . . ? H22A C22 H22B 107.3 . . ? N4 C16 C17 111.3(3) . . ? N4 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? N4 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N2 C8 C9 121.6(4) . . ? N2 C8 C7 115.1(4) . . ? C9 C8 C7 123.1(4) . . ? N4 C15 C14 115.3(3) . . ? N4 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? N4 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1B 118.6 . . ? C2 C1 H1B 118.6 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? N3 C7 C8 111.3(3) . . ? N3 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N3 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N5 C21 C20 123.0(4) . . ? N5 C21 H21A 118.5 . . ? C20 C21 H21A 118.5 . . ? C19 C18 C17 119.2(5) . . ? C19 C18 H18A 120.4 . . ? C17 C18 H18A 120.4 . . ? N3 C13 C14 113.7(3) . . ? N3 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? N3 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C26 C27 C28 120.2(5) . . ? C26 C27 H27A 119.9 . . ? C28 C27 H27A 119.9 . . ? C26 C25 C24 121.3(5) . . ? C26 C25 H25A 119.4 . . ? C24 C25 H25A 119.4 . . ? N2 C12 C11 122.9(5) . . ? N2 C12 H12A 118.6 . . ? C11 C12 H12A 118.6 . . ? C21 C20 C19 118.3(4) . . ? C21 C20 H20A 120.8 . . ? C19 C20 H20A 120.8 . . ? C25 C26 C27 119.9(5) . . ? C25 C26 H26A 120.1 . . ? C27 C26 H26A 120.1 . . ? C23 C24 C25 120.1(5) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C10 C9 C8 119.8(5) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C3 C4 C5 119.9(5) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C5 C6 N3 115.8(3) . . ? C5 C6 H6A 108.3 . . ? N3 C6 H6A 108.3 . . ? C5 C6 H6B 108.3 . . ? N3 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? C18 C19 C20 119.5(4) . . ? C18 C19 H19A 120.3 . . ? C20 C19 H19A 120.3 . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? C4 C3 C2 118.6(5) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? B2 F8 F7A 57.2(8) . . ? F6 B2 F8 121.4(8) . . ? F6 B2 F5 118.5(9) . . ? F8 B2 F5 112.4(8) . . ? F6 B2 F7B 102.3(8) . . ? F8 B2 F7B 103.2(7) . . ? F5 B2 F7B 92.0(7) . . ? F6 B2 F7A 84.1(10) . . ? F8 B2 F7A 75.2(9) . . ? F5 B2 F7A 82.6(11) . . ? F7B B2 F7A 173.1(11) . . ? F2 B1 F4 107.4(12) . . ? F2 B1 F3 122.7(14) . . ? F4 B1 F3 106.3(8) . . ? F2 B1 F1 109.4(9) . . ? F4 B1 F1 103.5(13) . . ? F3 B1 F1 105.9(12) . . ? B2 F7A F8 47.6(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.793 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 937145'