# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 Cd3 N8 O12' _chemical_formula_weight 1238.09 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.401(3) _cell_length_b 13.3519(11) _cell_length_c 15.8465(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.878(2) _cell_angle_gamma 90.00 _cell_volume 6220.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1914 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 20.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 1.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7609 _exptl_absorpt_correction_T_max 0.8474 _exptl_absorpt_process_details sadabs _exptl_special_details ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.213 -0.250 0.037 1005 237 ' ' 2 0.206 0.250 0.544 1005 237 ' ' _platon_squeeze_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 6069 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 26.02 _reflns_number_total 6069 _reflns_number_gt 4621 _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^)+(0.1197P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6069 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2003 _refine_ls_wR_factor_gt 0.1888 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cd1 Cd 0.117245(16) 0.30779(3) 0.23425(3) 0.02789(18) Uani 1 1 d . . . Cd2 Cd 0.0000 0.22595(6) 0.2500 0.0423(2) Uani 1 2 d S . . N1 N 0.1348(2) 0.4187(5) 0.3428(4) 0.0443(15) Uani 1 1 d . . . N2 N 0.1465(2) 0.5480(5) 0.4267(4) 0.0475(16) Uani 1 1 d . . . N3 N 0.1918(2) 0.3144(4) 0.1873(4) 0.0386(14) Uani 1 1 d . . . N4 N 0.2622(2) 0.2826(5) 0.1564(5) 0.0513(17) Uani 1 1 d . . . O1 O 0.06324(17) 0.2277(3) 0.3396(3) 0.0355(11) Uani 1 1 d . . . O2 O 0.1334(2) 0.1721(4) 0.3267(3) 0.0503(14) Uani 1 1 d . . . O3 O 0.03745(19) 0.3547(4) 0.1861(3) 0.0453(13) Uani 1 1 d . . . O4 O 0.09736(18) 0.4324(4) 0.1357(3) 0.0425(12) Uani 1 1 d . . . O5 O 0.1027(2) 0.1896(4) 0.1326(4) 0.0559(16) Uani 1 1 d . . . O6 O 0.0364(2) 0.1162(4) 0.1704(3) 0.0548(15) Uani 1 1 d . . . C1 C 0.0947(3) 0.1690(5) 0.3602(4) 0.0354(16) Uani 1 1 d . . . C2 C 0.0879(3) 0.0929(5) 0.4262(4) 0.0378(16) Uani 1 1 d . . . C3 C 0.0531(3) 0.0997(6) 0.4813(5) 0.0460(19) Uani 1 1 d . . . H3 H 0.0321 0.1514 0.4755 0.055 Uiso 1 1 calc R . . C4 C 0.0484(3) 0.0316(6) 0.5456(5) 0.052(2) Uani 1 1 d . . . H4 H 0.0249 0.0395 0.5835 0.063 Uiso 1 1 calc R . . C5 C 0.0777(3) -0.0479(5) 0.5552(4) 0.0391(17) Uani 1 1 d . . . C6 C 0.1119(3) -0.0586(6) 0.4980(5) 0.062(3) Uani 1 1 d . . . H6 H 0.1320 -0.1122 0.5023 0.075 Uiso 1 1 calc R . . C7 C 0.1162(3) 0.0105(7) 0.4347(6) 0.065(3) Uani 1 1 d . . . H7 H 0.1392 0.0016 0.3957 0.078 Uiso 1 1 calc R . . C8 C 0.0722(3) 0.1238(5) 0.1247(5) 0.0439(18) Uani 1 1 d . . . C9 C 0.0560(3) 0.4124(5) 0.1323(4) 0.0332(15) Uani 1 1 d . . . C10 C 0.0263(2) 0.4576(5) 0.0646(4) 0.0321(15) Uani 1 1 d . . . C11 C -0.0178(2) 0.4250(5) 0.0497(4) 0.0391(16) Uani 1 1 d . . . H11 H -0.0298 0.3748 0.0834 0.047 Uiso 1 1 calc R . . C12 C 0.0441(3) 0.5347(5) 0.0139(4) 0.0423(17) Uani 1 1 d . . . H12 H 0.0735 0.5581 0.0236 0.051 Uiso 1 1 calc R . . C13 C 0.1657(3) 0.3929(7) 0.4047(5) 0.062(2) Uani 1 1 d . . . H13 H 0.1790 0.3301 0.4104 0.074 Uiso 1 1 calc R . . C14 C 0.1236(3) 0.5131(6) 0.3585(4) 0.0418(17) Uani 1 1 d . . . C15 C 0.0886(4) 0.5701(7) 0.3120(7) 0.078(3) Uani 1 1 d . . . H15A H 0.1010 0.5948 0.2603 0.117 Uiso 1 1 calc R . . H15B H 0.0788 0.6254 0.3459 0.117 Uiso 1 1 calc R . . H15C H 0.0632 0.5272 0.2995 0.117 Uiso 1 1 calc R . . C16 C 0.1740(4) 0.4715(7) 0.4564(6) 0.067(3) Uani 1 1 d . . . H16 H 0.1940 0.4736 0.5023 0.080 Uiso 1 1 calc R . . C17 C 0.1452(3) 0.6470(6) 0.4660(5) 0.060(2) Uani 1 1 d . . . H17A H 0.1412 0.6397 0.5264 0.072 Uiso 1 1 calc R . . H17B H 0.1195 0.6844 0.4435 0.072 Uiso 1 1 calc R . . C18 C 0.1898(3) 0.7059(6) 0.4494(6) 0.058(2) Uani 1 1 d . . . H18A H 0.1897 0.7671 0.4823 0.069 Uiso 1 1 calc R . . H18B H 0.2156 0.6659 0.4682 0.069 Uiso 1 1 calc R . . C19 C 0.3047(3) 0.2315(7) 0.1418(6) 0.057(2) Uani 1 1 d . . . H19A H 0.3058 0.1706 0.1751 0.069 Uiso 1 1 calc R . . H19B H 0.3298 0.2740 0.1601 0.069 Uiso 1 1 calc R . . C20 C 0.2564(3) 0.3864(7) 0.1550(6) 0.067(3) Uani 1 1 d . . . H20 H 0.2784 0.4341 0.1432 0.080 Uiso 1 1 calc R . . C21 C 0.2127(3) 0.4038(6) 0.1740(5) 0.0475(19) Uani 1 1 d . . . H21 H 0.1991 0.4665 0.1775 0.057 Uiso 1 1 calc R . . C22 C 0.2225(3) 0.2423(5) 0.1770(5) 0.0383(16) Uani 1 1 d . . . C23 C 0.2125(3) 0.1339(6) 0.1803(6) 0.058(2) Uani 1 1 d . . . H23A H 0.2208 0.1032 0.1279 0.087 Uiso 1 1 calc R . . H23B H 0.1806 0.1241 0.1893 0.087 Uiso 1 1 calc R . . H23C H 0.2296 0.1038 0.2257 0.087 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 Cd1 0.0306(3) 0.0289(3) 0.0241(3) 0.00206(18) -0.00060(19) -0.00036(19) Cd2 0.0419(5) 0.0478(5) 0.0372(4) 0.000 0.0031(3) 0.000 N1 0.047(4) 0.052(4) 0.034(3) -0.005(3) -0.004(3) -0.001(3) N2 0.052(4) 0.053(4) 0.038(3) -0.007(3) 0.006(3) -0.016(3) N3 0.033(3) 0.037(3) 0.047(4) -0.001(3) 0.003(3) 0.002(3) N4 0.041(4) 0.047(4) 0.066(5) -0.007(3) 0.003(3) 0.004(3) O1 0.041(3) 0.033(2) 0.032(2) 0.0037(19) -0.003(2) 0.008(2) O2 0.053(4) 0.050(3) 0.048(3) 0.020(2) 0.013(3) 0.004(3) O3 0.051(3) 0.043(3) 0.042(3) 0.014(2) -0.008(2) 0.003(3) O4 0.040(3) 0.057(3) 0.030(2) 0.009(2) -0.005(2) 0.000(3) O5 0.056(4) 0.061(4) 0.051(3) -0.029(3) 0.002(3) -0.002(3) O6 0.062(4) 0.050(3) 0.053(3) -0.021(3) 0.007(3) 0.005(3) C1 0.045(4) 0.031(4) 0.030(3) 0.003(3) 0.009(3) 0.000(3) C2 0.041(4) 0.043(4) 0.029(3) 0.009(3) 0.004(3) 0.008(3) C3 0.035(4) 0.054(5) 0.050(4) 0.022(4) 0.015(3) 0.019(4) C4 0.054(5) 0.058(5) 0.046(4) 0.024(4) 0.011(4) 0.021(4) C5 0.040(4) 0.047(4) 0.031(4) 0.015(3) 0.006(3) 0.000(3) C6 0.071(6) 0.051(5) 0.065(5) 0.032(4) 0.023(5) 0.030(5) C7 0.061(6) 0.070(6) 0.065(5) 0.028(5) 0.040(5) 0.030(5) C8 0.058(5) 0.032(4) 0.041(4) -0.011(3) -0.005(4) -0.003(4) C9 0.044(4) 0.031(3) 0.025(3) 0.005(3) 0.002(3) 0.006(3) C10 0.027(3) 0.042(4) 0.027(3) 0.009(3) 0.002(3) 0.006(3) C11 0.034(4) 0.041(4) 0.042(4) 0.015(3) -0.004(3) -0.002(3) C12 0.035(4) 0.049(4) 0.043(4) 0.009(3) -0.006(3) 0.001(3) C13 0.079(7) 0.054(5) 0.051(5) -0.002(4) -0.031(5) -0.002(5) C14 0.045(4) 0.041(4) 0.039(4) -0.008(3) 0.012(3) -0.010(3) C15 0.090(8) 0.059(6) 0.083(7) -0.017(5) -0.031(6) 0.020(6) C16 0.077(7) 0.068(6) 0.055(5) -0.002(5) -0.029(5) -0.017(5) C17 0.075(6) 0.052(5) 0.054(5) -0.030(4) 0.019(5) -0.022(5) C18 0.056(6) 0.058(5) 0.059(5) -0.025(4) 0.016(4) -0.023(4) C19 0.038(5) 0.074(6) 0.060(5) 0.009(4) 0.016(4) 0.016(4) C20 0.055(6) 0.050(5) 0.096(7) -0.003(5) 0.024(5) -0.003(5) C21 0.043(5) 0.037(4) 0.063(5) 0.000(4) 0.012(4) 0.000(3) C22 0.032(4) 0.041(4) 0.042(4) 0.000(3) 0.006(3) -0.001(3) C23 0.057(6) 0.045(5) 0.072(6) 0.013(4) 0.022(5) 0.010(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 Cd1 O5 2.290(5) . ? Cd1 N1 2.321(6) . ? Cd1 N3 2.328(6) . ? Cd1 O4 2.350(5) . ? Cd1 O2 2.373(5) . ? Cd1 O1 2.556(5) . ? Cd2 O6 2.219(5) 2 ? Cd2 O6 2.219(5) . ? Cd2 O3 2.287(5) 2 ? Cd2 O3 2.287(5) . ? Cd2 O1 2.322(5) 2 ? Cd2 O1 2.322(5) . ? N1 C14 1.327(9) . ? N1 C13 1.372(10) . ? N2 C14 1.347(9) . ? N2 C16 1.381(12) . ? N2 C17 1.463(9) . ? N3 C22 1.331(9) . ? N3 C21 1.361(9) . ? N4 C22 1.330(10) . ? N4 C20 1.397(11) . ? N4 C19 1.445(10) . ? O1 C1 1.251(8) . ? O2 C1 1.263(9) . ? O3 C9 1.277(8) . ? O4 C9 1.245(8) . ? O5 C8 1.261(9) . ? O6 C8 1.291(10) . ? C1 C2 1.474(9) . ? C2 C3 1.359(10) . ? C2 C7 1.385(11) . ? C3 C4 1.374(10) . ? C3 H3 0.9300 . ? C4 C5 1.373(10) . ? C4 H4 0.9300 . ? C5 C6 1.372(11) . ? C5 C8 1.507(9) 6_556 ? C6 C7 1.370(11) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C5 1.507(9) 6 ? C9 C10 1.499(9) . ? C10 C11 1.385(10) . ? C10 C12 1.412(9) . ? C11 C12 1.371(9) 5_565 ? C11 H11 0.9300 . ? C12 C11 1.371(9) 5_565 ? C12 H12 0.9300 . ? C13 C16 1.350(12) . ? C13 H13 0.9300 . ? C14 C15 1.468(12) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16 0.9300 . ? C17 C18 1.554(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.496(12) 4 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C18 1.496(12) 4_545 ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.342(12) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.479(11) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 O5 Cd1 N1 175.9(2) . . ? O5 Cd1 N3 88.1(2) . . ? N1 Cd1 N3 90.8(2) . . ? O5 Cd1 O4 88.8(2) . . ? N1 Cd1 O4 95.2(2) . . ? N3 Cd1 O4 89.23(19) . . ? O5 Cd1 O2 86.7(2) . . ? N1 Cd1 O2 89.4(2) . . ? N3 Cd1 O2 92.6(2) . . ? O4 Cd1 O2 175.00(19) . . ? O5 Cd1 O1 93.44(19) . . ? N1 Cd1 O1 85.20(19) . . ? N3 Cd1 O1 145.31(18) . . ? O4 Cd1 O1 125.43(16) . . ? O2 Cd1 O1 52.97(17) . . ? O6 Cd2 O6 97.3(3) 2 . ? O6 Cd2 O3 90.3(2) 2 2 ? O6 Cd2 O3 171.1(2) . 2 ? O6 Cd2 O3 171.1(2) 2 . ? O6 Cd2 O3 90.3(2) . . ? O3 Cd2 O3 82.5(3) 2 . ? O6 Cd2 O1 88.05(19) 2 2 ? O6 Cd2 O1 92.71(19) . 2 ? O3 Cd2 O1 82.93(17) 2 2 ? O3 Cd2 O1 96.20(17) . 2 ? O6 Cd2 O1 92.71(19) 2 . ? O6 Cd2 O1 88.05(19) . . ? O3 Cd2 O1 96.20(17) 2 . ? O3 Cd2 O1 82.93(17) . . ? O1 Cd2 O1 178.9(2) 2 . ? C14 N1 C13 105.5(7) . . ? C14 N1 Cd1 133.8(5) . . ? C13 N1 Cd1 120.5(5) . . ? C14 N2 C16 107.5(7) . . ? C14 N2 C17 129.7(8) . . ? C16 N2 C17 122.9(7) . . ? C22 N3 C21 107.8(6) . . ? C22 N3 Cd1 131.0(5) . . ? C21 N3 Cd1 120.8(5) . . ? C22 N4 C20 107.2(7) . . ? C22 N4 C19 127.8(7) . . ? C20 N4 C19 124.9(8) . . ? C1 O1 Cd2 137.3(5) . . ? C1 O1 Cd1 88.2(4) . . ? Cd2 O1 Cd1 95.99(15) . . ? C1 O2 Cd1 96.4(4) . . ? C9 O3 Cd2 164.3(5) . . ? C9 O4 Cd1 96.3(4) . . ? C8 O5 Cd1 132.4(5) . . ? C8 O6 Cd2 132.1(5) . . ? O1 C1 O2 122.5(6) . . ? O1 C1 C2 120.6(6) . . ? O2 C1 C2 116.9(6) . . ? C3 C2 C7 116.6(7) . . ? C3 C2 C1 121.5(7) . . ? C7 C2 C1 122.0(6) . . ? C2 C3 C4 121.1(7) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.6(7) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 118.2(6) . . ? C6 C5 C8 120.0(7) . 6_556 ? C4 C5 C8 121.8(7) . 6_556 ? C7 C6 C5 119.3(7) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 123.0(7) . . ? C6 C7 H7 118.5 . . ? C2 C7 H7 118.5 . . ? O5 C8 O6 125.8(7) . . ? O5 C8 C5 117.2(7) . 6 ? O6 C8 C5 117.0(7) . 6 ? O4 C9 O3 121.8(6) . . ? O4 C9 C10 120.1(6) . . ? O3 C9 C10 118.0(6) . . ? C11 C10 C12 119.0(6) . . ? C11 C10 C9 122.0(6) . . ? C12 C10 C9 119.0(6) . . ? C12 C11 C10 121.3(7) 5_565 . ? C12 C11 H11 119.4 5_565 . ? C10 C11 H11 119.4 . . ? C11 C12 C10 119.7(7) 5_565 . ? C11 C12 H12 120.2 5_565 . ? C10 C12 H12 120.2 . . ? C16 C13 N1 110.5(8) . . ? C16 C13 H13 124.7 . . ? N1 C13 H13 124.7 . . ? N1 C14 N2 110.9(7) . . ? N1 C14 C15 124.8(7) . . ? N2 C14 C15 124.1(7) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 N2 105.6(7) . . ? C13 C16 H16 127.2 . . ? N2 C16 H16 127.2 . . ? N2 C17 C18 110.9(7) . . ? N2 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 112.5(8) 4 . ? C19 C18 H18A 109.1 4 . ? C17 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 4 . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? N4 C19 C18 111.7(7) . 4_545 ? N4 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 4_545 . ? N4 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 4_545 . ? H19A C19 H19B 108.0 . . ? C21 C20 N4 106.6(8) . . ? C21 C20 H20 126.7 . . ? N4 C20 H20 126.7 . . ? C20 C21 N3 108.5(7) . . ? C20 C21 H21 125.7 . . ? N3 C21 H21 125.7 . . ? N4 C22 N3 109.7(6) . . ? N4 C22 C23 125.5(7) . . ? N3 C22 C23 124.6(7) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cd1 N1 C14 -175(3) . . . . ? N3 Cd1 N1 C14 110.4(7) . . . . ? O4 Cd1 N1 C14 21.1(7) . . . . ? O2 Cd1 N1 C14 -157.0(7) . . . . ? O1 Cd1 N1 C14 -104.1(7) . . . . ? O5 Cd1 N1 C13 11(4) . . . . ? N3 Cd1 N1 C13 -63.4(7) . . . . ? O4 Cd1 N1 C13 -152.7(7) . . . . ? O2 Cd1 N1 C13 29.2(7) . . . . ? O1 Cd1 N1 C13 82.0(7) . . . . ? O5 Cd1 N3 C22 -54.0(7) . . . . ? N1 Cd1 N3 C22 122.0(7) . . . . ? O4 Cd1 N3 C22 -142.8(7) . . . . ? O2 Cd1 N3 C22 32.5(7) . . . . ? O1 Cd1 N3 C22 39.3(8) . . . . ? O5 Cd1 N3 C21 133.7(6) . . . . ? N1 Cd1 N3 C21 -50.3(6) . . . . ? O4 Cd1 N3 C21 44.9(6) . . . . ? O2 Cd1 N3 C21 -139.8(6) . . . . ? O1 Cd1 N3 C21 -133.0(5) . . . . ? O6 Cd2 O1 C1 69.7(7) 2 . . . ? O6 Cd2 O1 C1 -27.6(7) . . . . ? O3 Cd2 O1 C1 160.3(7) 2 . . . ? O3 Cd2 O1 C1 -118.1(7) . . . . ? O1 Cd2 O1 C1 -159.0(6) 2 . . . ? O6 Cd2 O1 Cd1 163.45(19) 2 . . . ? O6 Cd2 O1 Cd1 66.22(19) . . . . ? O3 Cd2 O1 Cd1 -105.95(17) 2 . . . ? O3 Cd2 O1 Cd1 -24.32(17) . . . . ? O1 Cd2 O1 Cd1 -65.18(12) 2 . . . ? O5 Cd1 O1 C1 83.3(4) . . . . ? N1 Cd1 O1 C1 -92.8(4) . . . . ? N3 Cd1 O1 C1 -8.4(6) . . . . ? O4 Cd1 O1 C1 174.2(4) . . . . ? O2 Cd1 O1 C1 0.1(4) . . . . ? O5 Cd1 O1 Cd2 -54.1(2) . . . . ? N1 Cd1 O1 Cd2 129.8(2) . . . . ? N3 Cd1 O1 Cd2 -145.8(3) . . . . ? O4 Cd1 O1 Cd2 36.8(2) . . . . ? O2 Cd1 O1 Cd2 -137.3(3) . . . . ? O5 Cd1 O2 C1 -96.9(5) . . . . ? N1 Cd1 O2 C1 84.4(5) . . . . ? N3 Cd1 O2 C1 175.1(5) . . . . ? O4 Cd1 O2 C1 -73(2) . . . . ? O1 Cd1 O2 C1 -0.1(4) . . . . ? O6 Cd2 O3 C9 -168.5(16) 2 . . . ? O6 Cd2 O3 C9 42.5(18) . . . . ? O3 Cd2 O3 C9 -132.3(19) 2 . . . ? O1 Cd2 O3 C9 -50.3(18) 2 . . . ? O1 Cd2 O3 C9 130.5(18) . . . . ? O5 Cd1 O4 C9 69.6(4) . . . . ? N1 Cd1 O4 C9 -111.6(4) . . . . ? N3 Cd1 O4 C9 157.7(4) . . . . ? O2 Cd1 O4 C9 46(2) . . . . ? O1 Cd1 O4 C9 -23.8(5) . . . . ? N1 Cd1 O5 C8 84(3) . . . . ? N3 Cd1 O5 C8 159.1(7) . . . . ? O4 Cd1 O5 C8 -111.7(7) . . . . ? O2 Cd1 O5 C8 66.3(7) . . . . ? O1 Cd1 O5 C8 13.8(7) . . . . ? O6 Cd2 O6 C8 -159.7(8) 2 . . . ? O3 Cd2 O6 C8 51.6(16) 2 . . . ? O3 Cd2 O6 C8 15.7(7) . . . . ? O1 Cd2 O6 C8 111.9(7) 2 . . . ? O1 Cd2 O6 C8 -67.2(7) . . . . ? Cd2 O1 C1 O2 96.7(9) . . . . ? Cd1 O1 C1 O2 -0.1(7) . . . . ? Cd2 O1 C1 C2 -83.9(8) . . . . ? Cd1 O1 C1 C2 179.3(6) . . . . ? Cd1 O2 C1 O1 0.1(8) . . . . ? Cd1 O2 C1 C2 -179.3(5) . . . . ? O1 C1 C2 C3 -17.5(11) . . . . ? O2 C1 C2 C3 162.0(8) . . . . ? O1 C1 C2 C7 161.9(8) . . . . ? O2 C1 C2 C7 -18.7(12) . . . . ? C7 C2 C3 C4 4.2(13) . . . . ? C1 C2 C3 C4 -176.4(8) . . . . ? C2 C3 C4 C5 -2.2(14) . . . . ? C3 C4 C5 C6 -0.6(13) . . . . ? C3 C4 C5 C8 -178.9(8) . . . 6_556 ? C4 C5 C6 C7 1.0(14) . . . . ? C8 C5 C6 C7 179.4(9) 6_556 . . . ? C5 C6 C7 C2 1.3(16) . . . . ? C3 C2 C7 C6 -3.9(15) . . . . ? C1 C2 C7 C6 176.7(9) . . . . ? Cd1 O5 C8 O6 10.0(13) . . . . ? Cd1 O5 C8 C5 -170.7(5) . . . 6 ? Cd2 O6 C8 O5 21.3(13) . . . . ? Cd2 O6 C8 C5 -158.1(5) . . . 6 ? Cd1 O4 C9 O3 12.6(7) . . . . ? Cd1 O4 C9 C10 -168.2(5) . . . . ? Cd2 O3 C9 O4 -118.9(17) . . . . ? Cd2 O3 C9 C10 62(2) . . . . ? O4 C9 C10 C11 168.9(7) . . . . ? O3 C9 C10 C11 -11.9(10) . . . . ? O4 C9 C10 C12 -10.2(10) . . . . ? O3 C9 C10 C12 169.0(6) . . . . ? C12 C10 C11 C12 0.9(12) . . . 5_565 ? C9 C10 C11 C12 -178.3(7) . . . 5_565 ? C11 C10 C12 C11 -0.9(12) . . . 5_565 ? C9 C10 C12 C11 178.3(7) . . . 5_565 ? C14 N1 C13 C16 -1.4(11) . . . . ? Cd1 N1 C13 C16 174.0(7) . . . . ? C13 N1 C14 N2 0.7(9) . . . . ? Cd1 N1 C14 N2 -173.7(5) . . . . ? C13 N1 C14 C15 -175.0(9) . . . . ? Cd1 N1 C14 C15 10.6(13) . . . . ? C16 N2 C14 N1 0.1(9) . . . . ? C17 N2 C14 N1 179.4(7) . . . . ? C16 N2 C14 C15 175.8(9) . . . . ? C17 N2 C14 C15 -4.8(13) . . . . ? N1 C13 C16 N2 1.4(12) . . . . ? C14 N2 C16 C13 -0.9(10) . . . . ? C17 N2 C16 C13 179.7(8) . . . . ? C14 N2 C17 C18 -108.0(10) . . . . ? C16 N2 C17 C18 71.2(11) . . . . ? N2 C17 C18 C19 66.4(11) . . . 4 ? C22 N4 C19 C18 92.0(11) . . . 4_545 ? C20 N4 C19 C18 -91.2(11) . . . 4_545 ? C22 N4 C20 C21 -0.7(10) . . . . ? C19 N4 C20 C21 -178.1(8) . . . . ? N4 C20 C21 N3 0.2(11) . . . . ? C22 N3 C21 C20 0.4(10) . . . . ? Cd1 N3 C21 C20 174.3(6) . . . . ? C20 N4 C22 N3 1.0(9) . . . . ? C19 N4 C22 N3 178.3(8) . . . . ? C20 N4 C22 C23 175.7(8) . . . . ? C19 N4 C22 C23 -7.0(13) . . . . ? C21 N3 C22 N4 -0.9(9) . . . . ? Cd1 N3 C22 N4 -173.9(5) . . . . ? C21 N3 C22 C23 -175.7(7) . . . . ? Cd1 N3 C22 C23 11.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.817 _refine_diff_density_min -2.521 _refine_diff_density_rms 0.172 _database_code_depnum_ccdc_archive 'CCDC 950269' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H40 Co3 N4 O12' _chemical_formula_weight 1101.68 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' O O 0.0106 0.0060 '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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.9345(14) _cell_length_b 26.096(3) _cell_length_c 19.2265(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6991.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1820 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 17.38 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.047 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2252 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8829 _exptl_absorpt_correction_T_max 0.9219 _exptl_absorpt_process_details sadabs _exptl_special_details ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.010 1428 312 ' ' 2 0.500 0.000 0.159 1427 311 ' ' _platon_squeeze_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 34702 _diffrn_reflns_av_R_equivalents 0.1027 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.55 _reflns_number_total 6528 _reflns_number_gt 3701 _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^)+(0.1391P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6528 _refine_ls_number_parameters 326 _refine_ls_number_restraints 81 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2365 _refine_ls_wR_factor_gt 0.2160 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 1.000 _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 1.02263(5) 0.14303(3) 0.06568(4) 0.0365(3) Uani 1 1 d . . . Co2 Co 1.0000 0.14389(3) 0.2500 0.0311(3) Uani 1 2 d S . . O1 O 1.1006(3) 0.14350(15) 0.16889(19) 0.0496(10) Uani 1 1 d . . . O5 O 0.5423(3) -0.29263(14) 0.0869(2) 0.0571(11) Uani 1 1 d . . . O3 O 0.9541(3) 0.07934(15) 0.0864(2) 0.0624(12) Uani 1 1 d . . . O4 O 0.9230(3) 0.08850(15) 0.1999(2) 0.0625(12) Uani 1 1 d . . . O6 O 0.5735(3) -0.29785(16) 0.2005(2) 0.0627(12) Uani 1 1 d . . . O2 O 1.1697(3) 0.14943(17) 0.0688(2) 0.0620(12) Uani 1 1 d . . . C1 C 1.1763(4) 0.1481(2) 0.1343(3) 0.0439(13) Uani 1 1 d . . . C21 C 0.5760(4) -0.2760(2) 0.1444(3) 0.0501(16) Uani 1 1 d . . . C2 C 1.2709(4) 0.1511(2) 0.1686(3) 0.0451(14) Uani 1 1 d . . . C18 C 0.6211(5) -0.2242(2) 0.1429(3) 0.0600(18) Uani 1 1 d . . . C5 C 1.4514(4) 0.1540(3) 0.2327(3) 0.0591(17) Uani 1 1 d . . . C15 C 0.7064(6) -0.1263(3) 0.1416(3) 0.071(2) Uani 1 1 d U . . C17 C 0.6435(6) -0.1998(2) 0.0823(3) 0.072(2) Uani 1 1 d . . . H17A H 0.6297 -0.2157 0.0402 0.087 Uiso 1 1 calc R . . C16 C 0.6867(6) -0.1517(2) 0.0822(3) 0.080(3) Uani 1 1 d . . . H16A H 0.7024 -0.1366 0.0399 0.096 Uiso 1 1 calc R . . C20 C 0.6816(7) -0.1508(3) 0.2027(4) 0.103(3) Uani 1 1 d U . . H20A H 0.6939 -0.1344 0.2447 0.123 Uiso 1 1 calc R . . C6 C 1.3684(5) 0.1484(3) 0.2724(4) 0.084(3) Uani 1 1 d . . . H6A H 1.3720 0.1461 0.3206 0.101 Uiso 1 1 calc R . . C4 C 1.4419(5) 0.1590(3) 0.1619(3) 0.085(3) Uani 1 1 d . . . H4A H 1.4968 0.1630 0.1350 0.101 Uiso 1 1 calc R . . C19 C 0.6397(7) -0.1983(3) 0.2036(4) 0.103(3) Uani 1 1 d . . . H19A H 0.6237 -0.2132 0.2460 0.124 Uiso 1 1 calc R . . C3 C 1.3534(5) 0.1582(3) 0.1293(3) 0.082(2) Uani 1 1 d . . . H3A H 1.3492 0.1625 0.0813 0.099 Uiso 1 1 calc R . . C8 C 0.9167(4) 0.0653(2) 0.1440(3) 0.0502(15) Uani 1 1 d . . . C9 C 0.8586(6) 0.0169(2) 0.1426(3) 0.064(2) Uani 1 1 d . . . C10 C 0.8496(8) -0.0112(3) 0.0829(4) 0.117(4) Uani 1 1 d . . . H10A H 0.8789 0.0002 0.0423 0.141 Uiso 1 1 calc R . . C11 C 0.7974(8) -0.0564(3) 0.0822(4) 0.118(4) Uani 1 1 d . . . H11A H 0.7906 -0.0742 0.0406 0.142 Uiso 1 1 calc R . . C14 C 0.8164(6) -0.0009(3) 0.2007(4) 0.076(2) Uani 1 1 d . . . H14A H 0.8214 0.0177 0.2418 0.092 Uiso 1 1 calc R . . C7 C 1.2798(4) 0.1462(3) 0.2386(3) 0.078(2) Uani 1 1 d . . . H7A H 1.2247 0.1411 0.2651 0.093 Uiso 1 1 calc R . . C12 C 0.7556(6) -0.0754(3) 0.1414(3) 0.076(2) Uani 1 1 d . . . C13 C 0.7657(6) -0.0463(3) 0.2001(3) 0.085(3) Uani 1 1 d . . . H13A H 0.7373 -0.0576 0.2412 0.101 Uiso 1 1 calc R . . N1 N 0.9999(5) 0.1410(3) -0.0388(3) 0.100(2) Uani 1 1 d DU . . C24 C 0.9620(8) 0.1017(4) -0.0769(4) 0.155(3) Uani 1 1 d DU . . H24A H 0.9309 0.0727 -0.0600 0.186 Uiso 1 1 calc R . . C22 C 1.0370(8) 0.1742(4) -0.0840(5) 0.154(3) Uani 1 1 d DU . . C25 C 1.0724(10) 0.2214(4) -0.0683(5) 0.157(4) Uani 1 1 d U . . H25A H 1.0746 0.2256 -0.0187 0.235 Uiso 1 1 calc R . . H25B H 1.0317 0.2473 -0.0881 0.235 Uiso 1 1 calc R . . H25C H 1.1360 0.2248 -0.0871 0.235 Uiso 1 1 calc R . . C27 C 1.0000 0.2041(9) -0.2500 0.231(6) Uani 1 2 d SDU . . H27A H 1.0283 0.2255 -0.2850 0.277 Uiso 1 1 d R . . C23 C 0.9793(9) 0.1138(5) -0.1455(5) 0.194(4) Uani 1 1 d DU . . H23A H 0.9615 0.0936 -0.1832 0.232 Uiso 1 1 calc R . . C26 C 1.0770(11) 0.1722(6) -0.2175(6) 0.220(4) Uani 1 1 d DU . . H26A H 1.1351 0.1918 -0.2091 0.264 Uiso 1 1 calc R . . H26B H 1.0919 0.1421 -0.2450 0.264 Uiso 1 1 calc R . . N2 N 1.0254(8) 0.1586(5) -0.1502(4) 0.202(3) Uani 1 1 d DU . . 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 0.0364(4) 0.0345(4) 0.0387(4) -0.0007(3) -0.0020(3) 0.0013(3) Co2 0.0305(5) 0.0271(5) 0.0358(6) 0.000 -0.0014(4) 0.000 O1 0.030(2) 0.072(3) 0.046(2) 0.001(2) 0.0015(17) 0.0026(19) O5 0.079(3) 0.042(2) 0.050(2) 0.005(2) -0.005(2) -0.022(2) O3 0.088(3) 0.047(3) 0.052(3) -0.005(2) -0.001(2) -0.029(2) O4 0.072(3) 0.061(3) 0.054(3) -0.019(2) 0.017(2) -0.029(2) O6 0.072(3) 0.060(3) 0.056(3) 0.016(2) -0.009(2) -0.032(2) O2 0.039(2) 0.107(4) 0.040(2) 0.008(2) -0.0015(18) 0.000(2) C1 0.035(3) 0.052(4) 0.045(3) 0.004(3) 0.007(3) -0.003(3) C21 0.058(4) 0.029(3) 0.063(4) 0.006(3) 0.012(3) -0.014(3) C2 0.030(3) 0.063(4) 0.042(3) -0.001(3) -0.003(2) -0.003(3) C18 0.070(5) 0.049(4) 0.061(4) 0.006(3) 0.002(3) -0.020(3) C5 0.031(3) 0.089(5) 0.057(4) -0.004(3) -0.003(3) -0.005(3) C15 0.109(6) 0.050(4) 0.055(4) -0.010(3) 0.020(4) -0.044(4) C17 0.120(7) 0.055(4) 0.041(4) -0.001(3) 0.002(4) -0.037(4) C16 0.134(8) 0.056(4) 0.049(4) 0.010(3) 0.017(4) -0.045(4) C20 0.167(7) 0.080(5) 0.061(4) -0.021(4) 0.017(5) -0.069(5) C6 0.035(4) 0.169(8) 0.047(4) 0.024(4) -0.001(3) 0.002(4) C4 0.027(3) 0.170(8) 0.057(4) 0.006(5) 0.007(3) -0.005(4) C19 0.186(10) 0.071(5) 0.053(5) 0.003(4) 0.019(5) -0.076(6) C3 0.049(4) 0.158(8) 0.040(4) 0.006(4) 0.001(3) -0.020(4) C8 0.057(4) 0.039(3) 0.054(4) -0.001(3) -0.002(3) -0.017(3) C9 0.093(6) 0.053(4) 0.047(4) -0.009(3) 0.011(3) -0.033(4) C10 0.199(10) 0.084(6) 0.068(5) -0.019(4) 0.024(6) -0.095(6) C11 0.206(11) 0.101(6) 0.048(4) -0.025(4) 0.032(5) -0.104(7) C14 0.107(6) 0.060(4) 0.063(5) -0.021(4) 0.012(4) -0.035(4) C7 0.024(3) 0.149(8) 0.060(4) 0.008(4) 0.005(3) -0.002(4) C12 0.118(7) 0.052(4) 0.056(4) -0.009(3) 0.015(4) -0.039(4) C13 0.122(7) 0.076(5) 0.055(4) -0.014(4) 0.027(4) -0.052(5) N1 0.141(6) 0.113(5) 0.046(3) 0.015(3) -0.033(3) -0.035(4) C24 0.224(8) 0.184(7) 0.059(4) -0.012(5) -0.035(5) -0.053(6) C22 0.228(8) 0.165(7) 0.069(4) 0.024(5) -0.032(5) -0.058(6) C25 0.223(12) 0.162(9) 0.084(6) 0.033(6) -0.008(7) -0.068(9) C27 0.338(15) 0.233(13) 0.121(9) 0.000 -0.032(10) 0.000 C23 0.282(9) 0.231(8) 0.068(5) -0.018(5) -0.035(6) -0.080(7) C26 0.324(12) 0.230(10) 0.106(6) 0.023(6) -0.014(7) -0.038(7) N2 0.308(9) 0.219(7) 0.078(4) 0.011(5) -0.018(5) -0.070(6) _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 O5 1.951(4) 8_765 ? Co1 O3 1.958(4) . ? Co1 N1 2.034(6) . ? Co1 O2 2.057(4) . ? Co1 O1 2.262(4) . ? Co1 C1 2.518(6) . ? Co2 O4 2.041(4) . ? Co2 O4 2.041(4) 3_755 ? Co2 O6 2.065(4) 6_666 ? Co2 O6 2.065(4) 8_765 ? Co2 O1 2.097(4) 3_755 ? Co2 O1 2.097(4) . ? O1 C1 1.253(6) . ? O5 C21 1.277(7) . ? O5 Co1 1.951(4) 8_755 ? O3 C8 1.277(6) . ? O4 C8 1.237(6) . ? O6 C21 1.222(6) . ? O6 Co2 2.065(4) 6_556 ? O2 C1 1.263(6) . ? C1 C2 1.476(8) . ? C21 C18 1.490(8) . ? C2 C7 1.359(8) . ? C2 C3 1.388(8) . ? C18 C17 1.364(8) . ? C18 C19 1.374(9) . ? C5 C4 1.373(9) . ? C5 C6 1.393(9) . ? C5 C5 1.510(12) 3_855 ? C15 C16 1.349(9) . ? C15 C20 1.380(9) . ? C15 C12 1.494(9) . ? C17 C16 1.392(8) . ? C17 H17A 0.9300 . ? C16 H16A 0.9300 . ? C20 C19 1.371(8) . ? C20 H20A 0.9300 . ? C6 C7 1.397(9) . ? C6 H6A 0.9300 . ? C4 C3 1.384(9) . ? C4 H4A 0.9300 . ? C19 H19A 0.9300 . ? C3 H3A 0.9300 . ? C8 C9 1.501(8) . ? C9 C14 1.345(8) . ? C9 C10 1.367(9) . ? C10 C11 1.386(9) . ? C10 H10A 0.9300 . ? C11 C12 1.371(9) . ? C11 H11A 0.9300 . ? C14 C13 1.381(8) . ? C14 H14A 0.9300 . ? C7 H7A 0.9300 . ? C12 C13 1.369(8) . ? C13 H13A 0.9300 . ? N1 C22 1.332(8) . ? N1 C24 1.368(8) . ? C24 C23 1.376(8) . ? C24 H24A 0.9300 . ? C22 N2 1.346(8) . ? C22 C25 1.362(13) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C27 C26 1.494(9) 3_754 ? C27 C26 1.494(9) . ? C27 H27A 0.9600 . ? C23 N2 1.337(9) . ? C23 H23A 0.9300 . ? C26 N2 1.522(9) . ? C26 H26A 0.9700 . ? C26 H26B 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 O5 Co1 O3 117.5(2) 8_765 . ? O5 Co1 N1 99.0(2) 8_765 . ? O3 Co1 N1 95.9(2) . . ? O5 Co1 O2 112.72(18) 8_765 . ? O3 Co1 O2 123.30(19) . . ? N1 Co1 O2 100.7(2) . . ? O5 Co1 O1 91.98(16) 8_765 . ? O3 Co1 O1 93.44(16) . . ? N1 Co1 O1 160.2(2) . . ? O2 Co1 O1 59.72(14) . . ? O5 Co1 C1 103.88(18) 8_765 . ? O3 Co1 C1 110.63(18) . . ? N1 Co1 C1 130.6(2) . . ? O2 Co1 C1 29.95(15) . . ? O1 Co1 C1 29.77(15) . . ? O4 Co2 O4 89.8(3) . 3_755 ? O4 Co2 O6 177.58(18) . 6_666 ? O4 Co2 O6 92.50(19) 3_755 6_666 ? O4 Co2 O6 92.50(19) . 8_765 ? O4 Co2 O6 177.58(18) 3_755 8_765 ? O6 Co2 O6 85.2(3) 6_666 8_765 ? O4 Co2 O1 89.76(15) . 3_755 ? O4 Co2 O1 89.84(15) 3_755 3_755 ? O6 Co2 O1 89.59(15) 6_666 3_755 ? O6 Co2 O1 90.83(16) 8_765 3_755 ? O4 Co2 O1 89.84(15) . . ? O4 Co2 O1 89.76(15) 3_755 . ? O6 Co2 O1 90.83(16) 6_666 . ? O6 Co2 O1 89.59(15) 8_765 . ? O1 Co2 O1 179.4(2) 3_755 . ? C1 O1 Co2 163.2(4) . . ? C1 O1 Co1 86.5(3) . . ? Co2 O1 Co1 109.33(16) . . ? C21 O5 Co1 130.2(4) . 8_755 ? C8 O3 Co1 128.2(4) . . ? C8 O4 Co2 142.5(4) . . ? C21 O6 Co2 139.9(4) . 6_556 ? C1 O2 Co1 95.7(3) . . ? O1 C1 O2 118.1(5) . . ? O1 C1 C2 121.3(5) . . ? O2 C1 C2 120.6(5) . . ? O1 C1 Co1 63.8(3) . . ? O2 C1 Co1 54.4(3) . . ? C2 C1 Co1 175.0(4) . . ? O6 C21 O5 126.5(5) . . ? O6 C21 C18 116.9(6) . . ? O5 C21 C18 116.6(5) . . ? C7 C2 C3 118.5(6) . . ? C7 C2 C1 121.3(5) . . ? C3 C2 C1 120.2(5) . . ? C17 C18 C19 117.0(6) . . ? C17 C18 C21 122.4(6) . . ? C19 C18 C21 120.7(6) . . ? C4 C5 C6 118.3(6) . . ? C4 C5 C5 121.6(7) . 3_855 ? C6 C5 C5 120.2(7) . 3_855 ? C16 C15 C20 116.2(6) . . ? C16 C15 C12 121.8(6) . . ? C20 C15 C12 122.0(6) . . ? C18 C17 C16 121.4(6) . . ? C18 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C15 C16 C17 122.0(6) . . ? C15 C16 H16A 119.0 . . ? C17 C16 H16A 119.0 . . ? C19 C20 C15 122.5(7) . . ? C19 C20 H20A 118.7 . . ? C15 C20 H20A 118.7 . . ? C5 C6 C7 118.9(6) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C5 C4 C3 122.3(6) . . ? C5 C4 H4A 118.9 . . ? C3 C4 H4A 118.9 . . ? C20 C19 C18 120.9(6) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C4 C3 C2 119.5(6) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? O4 C8 O3 125.8(5) . . ? O4 C8 C9 117.8(5) . . ? O3 C8 C9 116.4(5) . . ? C14 C9 C10 118.1(6) . . ? C14 C9 C8 120.7(6) . . ? C10 C9 C8 121.1(6) . . ? C9 C10 C11 120.9(7) . . ? C9 C10 H10A 119.6 . . ? C11 C10 H10A 119.6 . . ? C12 C11 C10 121.6(7) . . ? C12 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C9 C14 C13 120.9(6) . . ? C9 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C2 C7 C6 122.5(6) . . ? C2 C7 H7A 118.7 . . ? C6 C7 H7A 118.7 . . ? C13 C12 C11 116.1(6) . . ? C13 C12 C15 122.5(6) . . ? C11 C12 C15 121.3(6) . . ? C12 C13 C14 122.4(6) . . ? C12 C13 H13A 118.8 . . ? C14 C13 H13A 118.8 . . ? C22 N1 C24 106.7(8) . . ? C22 N1 Co1 124.5(6) . . ? C24 N1 Co1 127.5(6) . . ? N1 C24 C23 105.9(9) . . ? N1 C24 H24A 127.0 . . ? C23 C24 H24A 127.0 . . ? N1 C22 N2 111.9(9) . . ? N1 C22 C25 125.8(9) . . ? N2 C22 C25 121.8(10) . . ? 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 . . ? C26 C27 C26 112(2) 3_754 . ? C26 C27 H27A 109.1 3_754 . ? C26 C27 H27A 108.8 . . ? N2 C23 C24 110.4(10) . . ? N2 C23 H23A 124.8 . . ? C24 C23 H23A 124.8 . . ? C27 C26 N2 98.5(10) . . ? C27 C26 H26A 112.1 . . ? N2 C26 H26A 112.1 . . ? C27 C26 H26B 112.1 . . ? N2 C26 H26B 112.1 . . ? H26A C26 H26B 109.7 . . ? C23 N2 C22 105.0(9) . . ? C23 N2 C26 119.2(10) . . ? C22 N2 C26 132.6(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.119 _refine_diff_density_min -0.996 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 950270'