# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Feng Luo' 'Guo-lin Huang' 'Mingbiao Luo' _publ_contact_author_name 'Feng Luo' _publ_contact_author_email ECIT.LUOFENG@GMAIL.COM _publ_section_title ; Chiral or achiral camphorate-based complexes controlled by the configuration of N-donor co-ligands ; # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 761487' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 N O4 Zn' _chemical_formula_weight 340.67 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7056(15) _cell_length_b 11.588(2) _cell_length_c 17.604(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.37(3) _cell_angle_gamma 90.00 _cell_volume 1535.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3980 _cell_measurement_theta_min 2.1192 _cell_measurement_theta_max 27.1171 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 1.613 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7385 _exptl_absorpt_correction_T_max 0.7939 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11412 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.1434 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5076 _reflns_number_gt 3555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0775P)^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 SHELXL _refine_ls_extinction_coef 0.0026(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 5076 _refine_ls_number_parameters 387 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3052(12) 0.0663(9) 0.6718(6) 0.038(3) Uani 1 1 d . . . H1 H 0.3131 0.1234 0.6340 0.046 Uiso 1 1 calc R . . C2 C 0.2910(11) 0.4971(11) 0.6263(6) 0.030(2) Uani 1 1 d . . . C3 C 0.4254(11) -0.0221(8) 0.6818(6) 0.033(2) Uani 1 1 d . . . H3 H 0.5167 -0.0237 0.6531 0.039 Uiso 1 1 calc R . . C4 C 0.3095(12) 0.5801(9) 0.5049(6) 0.028(3) Uani 1 1 d . . . C5 C 0.4128(14) -0.1089(9) 0.7339(6) 0.032(3) Uani 1 1 d . . . C6 C 0.3045(14) 0.6276(10) 1.0023(7) 0.039(3) Uani 1 1 d . . . C7 C 0.2760(11) -0.1033(9) 0.7737(6) 0.028(3) Uani 1 1 d . . . H7 H 0.2595 -0.1632 0.8084 0.034 Uiso 1 1 calc R . . C8 C 0.2920(12) 0.7184(11) 1.1267(6) 0.031(2) Uani 1 1 d . . . C9 C 0.1636(11) -0.0083(10) 0.7618(6) 0.028(2) Uani 1 1 d . . . H9 H 0.0725 -0.0041 0.7905 0.034 Uiso 1 1 calc R . . C10 C 0.1791(12) 0.7656(9) 1.1800(7) 0.032(3) Uani 1 1 d . . . C11 C 0.5527(11) -0.2018(9) 0.7523(6) 0.030(2) Uani 1 1 d . . . C12 C 0.7107(12) -0.1920(9) 0.7297(6) 0.030(3) Uani 1 1 d . . . H12 H 0.7352 -0.1249 0.7029 0.036 Uiso 1 1 calc R . . C13 C 0.8371(11) -0.2806(10) 0.7460(6) 0.028(2) Uani 1 1 d . . . H13 H 0.9490 -0.2713 0.7324 0.034 Uiso 1 1 calc R . . C14 C 0.5083(12) -0.3077(9) 0.7837(7) 0.040(3) Uani 1 1 d . . . H14 H 0.3947 -0.3211 0.7949 0.048 Uiso 1 1 calc R . . C15 C 0.6441(13) -0.3920(9) 0.7974(7) 0.043(3) Uani 1 1 d . . . H15 H 0.6197 -0.4630 0.8200 0.051 Uiso 1 1 calc R . . C16 C 0.2008(12) 0.5992(10) 0.9206(7) 0.032(3) Uani 1 1 d . . . C17 C 0.1834(11) 0.4375(8) 0.6792(7) 0.027(3) Uani 1 1 d . . . C18 C 0.2206(12) 0.6118(9) 0.4207(6) 0.031(3) Uani 1 1 d . . . C19 C 0.1775(12) 0.5576(8) 0.5561(6) 0.034(2) Uani 1 1 d . . . C20 C 0.4110(13) 0.4157(10) 0.5935(7) 0.061(4) Uani 1 1 d . . . H20A H 0.3623 0.3363 0.5897 0.073 Uiso 1 1 calc R . . H20B H 0.5315 0.4144 0.6273 0.073 Uiso 1 1 calc R . . C21 C 0.4179(13) 0.4629(10) 0.5108(6) 0.046(3) Uani 1 1 d . . . H21A H 0.3616 0.4081 0.4697 0.055 Uiso 1 1 calc R . . H21B H 0.5420 0.4769 0.5062 0.055 Uiso 1 1 calc R . . C22 C 0.0263(14) 0.4792(11) 0.5128(6) 0.040(3) Uani 1 1 d . . . H22A H 0.0773 0.4115 0.4923 0.059 Uiso 1 1 calc R . . H22B H -0.0474 0.5222 0.4697 0.059 Uiso 1 1 calc R . . H22C H -0.0470 0.4540 0.5488 0.059 Uiso 1 1 calc R . . C23 C 0.0872(16) 0.6678(9) 0.5788(7) 0.063(3) Uani 1 1 d . . . H23A H -0.0188 0.6463 0.5978 0.095 Uiso 1 1 calc R . . H23B H 0.0530 0.7177 0.5331 0.095 Uiso 1 1 calc R . . H23C H 0.1703 0.7091 0.6197 0.095 Uiso 1 1 calc R . . C24 C 0.3116(14) 0.5298(9) 1.0636(6) 0.048(3) Uani 1 1 d . . . H24A H 0.1970 0.4880 1.0552 0.058 Uiso 1 1 calc R . . H24B H 0.4072 0.4740 1.0607 0.058 Uiso 1 1 calc R . . C25 C 0.3493(16) 0.5920(10) 1.1421(7) 0.061(3) Uani 1 1 d . . . H25A H 0.4774 0.5877 1.1665 0.073 Uiso 1 1 calc R . . H25B H 0.2815 0.5557 1.1776 0.073 Uiso 1 1 calc R . . C26 C 0.2008(12) 0.7260(9) 1.0411(6) 0.036(2) Uani 1 1 d . . . C27 C 0.4375(15) 0.6807(10) 0.5361(7) 0.060(3) Uani 1 1 d . . . H27A H 0.3701 0.7529 0.5330 0.091 Uiso 1 1 calc R . . H27B H 0.5275 0.6874 0.5046 0.091 Uiso 1 1 calc R . . H27C H 0.4957 0.6655 0.5903 0.091 Uiso 1 1 calc R . . C28 C 0.4872(14) 0.6687(12) 0.9969(8) 0.066(4) Uani 1 1 d . . . H28A H 0.5413 0.6126 0.9673 0.100 Uiso 1 1 calc R . . H28B H 0.5614 0.6764 1.0493 0.100 Uiso 1 1 calc R . . H28C H 0.4777 0.7436 0.9705 0.100 Uiso 1 1 calc R . . C29 C 0.2243(16) 0.8464(10) 1.0089(8) 0.070(4) Uani 1 1 d . . . H29A H 0.1587 0.8510 0.9547 0.105 Uiso 1 1 calc R . . H29B H 0.3507 0.8607 1.0113 0.105 Uiso 1 1 calc R . . H29C H 0.1785 0.9044 1.0400 0.105 Uiso 1 1 calc R . . C30 C 0.0020(11) 0.6944(12) 1.0256(6) 0.048(3) Uani 1 1 d . . . H30A H -0.0573 0.7420 1.0585 0.072 Uiso 1 1 calc R . . H30B H -0.0108 0.6127 1.0378 0.072 Uiso 1 1 calc R . . H30C H -0.0524 0.7084 0.9708 0.072 Uiso 1 1 calc R . . N1 N 0.8019(10) -0.3793(8) 0.7810(5) 0.028(2) Uani 1 1 d . . . N2 N 0.1758(11) 0.0777(7) 0.7124(6) 0.029(2) Uani 1 1 d . . . O1 O 0.1365(8) 0.4926(7) 0.9103(4) 0.0320(16) Uani 1 1 d . . . O2 O 0.1800(8) 0.8729(6) 1.1900(4) 0.0311(19) Uani 1 1 d . . . O3 O 0.1845(9) 0.6667(6) 0.8655(4) 0.0330(19) Uani 1 1 d . . . O4 O 0.0868(9) 0.6989(7) 1.2119(4) 0.0368(18) Uani 1 1 d . . . O5 O 0.1790(9) 0.3304(6) 0.6823(5) 0.040(2) Uani 1 1 d . . . O6 O 0.1041(9) 0.5065(8) 0.7178(4) 0.0386(19) Uani 1 1 d . . . O7 O 0.2095(9) 0.5377(6) 0.3683(5) 0.038(2) Uani 1 1 d . . . O8 O 0.1455(8) 0.7087(7) 0.4081(4) 0.0332(17) Uani 1 1 d . . . Zn1 Zn 0.00258(13) 0.20972(7) 0.69495(7) 0.0293(4) Uani 1 1 d . . . Zn2 Zn -0.00791(13) 0.49556(6) 0.80499(7) 0.0284(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(6) 0.044(7) 0.026(7) 0.005(5) 0.007(5) 0.004(5) C2 0.030(5) 0.034(6) 0.031(7) -0.001(6) 0.017(5) 0.004(5) C3 0.027(5) 0.034(6) 0.041(7) 0.009(4) 0.017(4) -0.002(4) C4 0.034(5) 0.028(6) 0.022(7) -0.006(5) 0.005(5) 0.002(4) C5 0.045(5) 0.024(5) 0.029(7) 0.006(4) 0.016(5) 0.000(4) C6 0.048(7) 0.031(7) 0.045(9) -0.003(6) 0.022(6) 0.001(5) C7 0.027(5) 0.027(6) 0.032(7) 0.003(5) 0.011(5) 0.004(4) C8 0.047(6) 0.033(6) 0.014(6) -0.010(5) 0.006(4) 0.016(5) C9 0.035(5) 0.019(5) 0.038(7) 0.001(5) 0.025(5) 0.005(4) C10 0.031(5) 0.032(7) 0.035(8) -0.006(5) 0.013(5) -0.008(4) C11 0.030(5) 0.030(5) 0.033(7) 0.003(5) 0.012(4) 0.010(4) C12 0.036(5) 0.025(6) 0.034(7) 0.009(5) 0.019(5) 0.000(4) C13 0.034(5) 0.020(6) 0.029(7) 0.003(5) 0.004(4) -0.001(4) C14 0.043(5) 0.033(6) 0.051(7) 0.014(5) 0.022(5) 0.007(4) C15 0.055(6) 0.020(5) 0.061(9) 0.025(5) 0.030(6) 0.011(4) C16 0.024(5) 0.032(6) 0.046(9) -0.015(6) 0.020(5) 0.010(4) C17 0.027(5) 0.015(5) 0.035(8) -0.001(5) -0.005(5) -0.004(4) C18 0.032(5) 0.025(6) 0.039(8) -0.002(5) 0.017(5) 0.000(4) C19 0.047(5) 0.022(5) 0.032(6) 0.003(4) 0.009(5) 0.005(4) C20 0.043(6) 0.063(8) 0.084(10) 0.034(7) 0.030(6) 0.022(5) C21 0.049(6) 0.054(7) 0.040(7) 0.008(5) 0.025(5) 0.005(5) C22 0.053(6) 0.051(7) 0.015(6) 0.004(5) 0.009(5) -0.024(5) C23 0.103(9) 0.033(6) 0.065(9) 0.012(6) 0.042(7) 0.020(6) C24 0.054(6) 0.032(6) 0.050(8) -0.002(5) -0.009(5) 0.008(4) C25 0.073(8) 0.059(8) 0.053(9) 0.013(6) 0.018(7) 0.036(6) C26 0.049(5) 0.030(5) 0.031(6) 0.009(5) 0.014(5) 0.002(4) C27 0.072(7) 0.062(8) 0.047(8) 0.008(6) 0.012(6) -0.030(6) C28 0.054(7) 0.089(10) 0.057(9) -0.020(7) 0.013(6) -0.004(6) C29 0.089(8) 0.036(7) 0.091(11) 0.038(7) 0.033(8) 0.006(6) C30 0.023(5) 0.079(10) 0.042(8) -0.021(7) 0.009(5) 0.010(5) N1 0.017(4) 0.032(5) 0.036(6) 0.004(4) 0.009(4) 0.002(3) N2 0.038(4) 0.014(4) 0.038(6) -0.005(4) 0.013(4) -0.007(3) O1 0.048(4) 0.019(4) 0.031(4) -0.002(4) 0.014(3) 0.005(4) O2 0.034(4) 0.016(4) 0.045(5) -0.003(3) 0.014(4) -0.004(3) O3 0.038(4) 0.037(5) 0.029(5) 0.004(4) 0.018(3) -0.003(3) O4 0.061(4) 0.023(4) 0.030(5) 0.006(4) 0.018(4) -0.014(4) O5 0.037(4) 0.028(5) 0.060(6) -0.005(4) 0.022(4) 0.004(3) O6 0.056(4) 0.029(4) 0.040(5) 0.003(4) 0.031(4) 0.006(4) O7 0.041(4) 0.031(5) 0.044(6) -0.008(4) 0.013(4) 0.003(3) O8 0.052(4) 0.012(3) 0.036(5) 0.000(4) 0.009(3) -0.001(4) Zn1 0.0369(7) 0.0197(7) 0.0332(9) 0.0008(6) 0.0119(6) 0.0037(5) Zn2 0.0371(7) 0.0184(7) 0.0328(9) 0.0015(6) 0.0141(6) 0.0044(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.353(12) . ? C1 C3 1.367(13) . ? C1 H1 0.9500 . ? C2 C20 1.520(14) . ? C2 C19 1.524(13) . ? C2 C17 1.536(14) . ? C3 C5 1.379(13) . ? C3 H3 0.9500 . ? C4 C19 1.519(13) . ? C4 C18 1.538(14) . ? C4 C27 1.550(13) . ? C4 C21 1.587(13) . ? C5 C7 1.387(12) . ? C5 C11 1.509(10) . ? C6 C28 1.509(14) . ? C6 C16 1.525(16) . ? C6 C24 1.558(15) . ? C6 C26 1.625(14) . ? C7 C9 1.389(14) . ? C7 H7 0.9500 . ? C8 C10 1.513(14) . ? C8 C26 1.523(13) . ? C8 C25 1.537(16) . ? C9 N2 1.339(14) . ? C9 H9 0.9500 . ? C10 O2 1.256(13) . ? C10 O4 1.261(12) . ? C11 C12 1.364(11) . ? C11 C14 1.417(15) . ? C12 C13 1.402(14) . ? C12 H12 0.9500 . ? C13 N1 1.353(14) . ? C13 H13 0.9500 . ? C14 C15 1.414(13) . ? C14 H14 0.9500 . ? C15 N1 1.317(11) . ? C15 H15 0.9500 . ? C16 O3 1.231(13) . ? C16 O1 1.329(14) . ? C17 O5 1.243(12) . ? C17 O6 1.285(12) . ? C18 O7 1.250(12) . ? C18 O8 1.262(13) . ? C19 C22 1.545(13) . ? C19 C23 1.546(13) . ? C20 C21 1.567(14) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.531(15) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C29 1.531(13) . ? C26 C30 1.542(12) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N1 Zn2 2.041(8) 1_645 ? N2 Zn1 2.010(8) . ? O1 Zn2 1.948(7) . ? O2 Zn2 1.959(6) 2_557 ? O4 Zn1 1.914(7) 2_557 ? O5 Zn1 1.996(7) . ? O6 Zn2 1.920(7) . ? O8 Zn1 1.925(7) 2_556 ? Zn1 O4 1.914(7) 2_547 ? Zn1 O8 1.925(7) 2_546 ? Zn2 O2 1.959(7) 2_547 ? Zn2 N1 2.041(8) 1_465 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C3 124.2(10) . . ? N2 C1 H1 117.9 . . ? C3 C1 H1 117.9 . . ? C20 C2 C19 105.5(8) . . ? C20 C2 C17 113.8(10) . . ? C19 C2 C17 114.1(8) . . ? C1 C3 C5 119.3(9) . . ? C1 C3 H3 120.4 . . ? C5 C3 H3 120.4 . . ? C19 C4 C18 113.3(8) . . ? C19 C4 C27 112.1(9) . . ? C18 C4 C27 106.2(9) . . ? C19 C4 C21 103.0(8) . . ? C18 C4 C21 112.7(9) . . ? C27 C4 C21 109.6(8) . . ? C3 C5 C7 118.2(10) . . ? C3 C5 C11 121.0(8) . . ? C7 C5 C11 120.6(8) . . ? C28 C6 C16 108.4(9) . . ? C28 C6 C24 112.3(10) . . ? C16 C6 C24 115.5(9) . . ? C28 C6 C26 110.8(9) . . ? C16 C6 C26 110.0(8) . . ? C24 C6 C26 99.7(8) . . ? C5 C7 C9 118.5(10) . . ? C5 C7 H7 120.8 . . ? C9 C7 H7 120.8 . . ? C10 C8 C26 112.8(8) . . ? C10 C8 C25 114.6(10) . . ? C26 C8 C25 106.5(9) . . ? N2 C9 C7 124.1(8) . . ? N2 C9 H9 118.0 . . ? C7 C9 H9 118.0 . . ? O2 C10 O4 122.1(10) . . ? O2 C10 C8 117.3(10) . . ? O4 C10 C8 120.6(10) . . ? C12 C11 C14 119.4(9) . . ? C12 C11 C5 121.3(9) . . ? C14 C11 C5 118.7(8) . . ? C11 C12 C13 120.3(10) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? N1 C13 C12 120.9(8) . . ? N1 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C11 115.6(8) . . ? C15 C14 H14 122.2 . . ? C11 C14 H14 122.2 . . ? N1 C15 C14 124.7(9) . . ? N1 C15 H15 117.6 . . ? C14 C15 H15 117.6 . . ? O3 C16 O1 120.8(11) . . ? O3 C16 C6 123.4(10) . . ? O1 C16 C6 115.7(11) . . ? O5 C17 O6 125.3(10) . . ? O5 C17 C2 119.9(10) . . ? O6 C17 C2 114.8(9) . . ? O7 C18 O8 121.6(11) . . ? O7 C18 C4 119.6(9) . . ? O8 C18 C4 118.4(9) . . ? C4 C19 C2 102.7(7) . . ? C4 C19 C22 109.7(9) . . ? C2 C19 C22 111.7(9) . . ? C4 C19 C23 114.0(8) . . ? C2 C19 C23 112.5(9) . . ? C22 C19 C23 106.3(8) . . ? C2 C20 C21 106.4(8) . . ? C2 C20 H20A 110.5 . . ? C21 C20 H20A 110.5 . . ? C2 C20 H20B 110.5 . . ? C21 C20 H20B 110.5 . . ? H20A C20 H20B 108.6 . . ? C20 C21 C4 103.7(8) . . ? C20 C21 H21A 111.0 . . ? C4 C21 H21A 111.0 . . ? C20 C21 H21B 111.0 . . ? C4 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C6 104.7(9) . . ? C25 C24 H24A 110.8 . . ? C6 C24 H24A 110.8 . . ? C25 C24 H24B 110.8 . . ? C6 C24 H24B 110.8 . . ? H24A C24 H24B 108.9 . . ? C24 C25 C8 107.3(9) . . ? C24 C25 H25A 110.3 . . ? C8 C25 H25A 110.3 . . ? C24 C25 H25B 110.3 . . ? C8 C25 H25B 110.3 . . ? H25A C25 H25B 108.5 . . ? C8 C26 C29 110.7(10) . . ? C8 C26 C30 113.0(8) . . ? C29 C26 C30 110.1(9) . . ? C8 C26 C6 102.1(8) . . ? C29 C26 C6 112.1(9) . . ? C30 C26 C6 108.6(9) . . ? C4 C27 H27A 109.5 . . ? C4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C6 C28 H28A 109.5 . . ? C6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C15 N1 C13 118.6(9) . . ? C15 N1 Zn2 122.1(7) . 1_645 ? C13 N1 Zn2 119.3(6) . 1_645 ? C9 N2 C1 115.6(9) . . ? C9 N2 Zn1 122.0(7) . . ? C1 N2 Zn1 122.3(7) . . ? C16 O1 Zn2 103.5(8) . . ? C10 O2 Zn2 137.8(6) . 2_557 ? C10 O4 Zn1 133.0(8) . 2_557 ? C17 O5 Zn1 136.9(7) . . ? C17 O6 Zn2 136.7(8) . . ? C18 O8 Zn1 109.2(7) . 2_556 ? O4 Zn1 O8 123.9(3) 2_547 2_546 ? O4 Zn1 O5 121.4(4) 2_547 . ? O8 Zn1 O5 100.3(3) 2_546 . ? O4 Zn1 N2 99.7(4) 2_547 . ? O8 Zn1 N2 112.3(4) 2_546 . ? O5 Zn1 N2 96.0(3) . . ? O6 Zn2 O1 120.0(3) . . ? O6 Zn2 O2 120.6(4) . 2_547 ? O1 Zn2 O2 101.5(3) . 2_547 ? O6 Zn2 N1 102.3(3) . 1_465 ? O1 Zn2 N1 116.6(3) . 1_465 ? O2 Zn2 N1 93.6(3) 2_547 1_465 ? 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 N2 C1 C3 C5 2.7(17) . . . . ? C1 C3 C5 C7 0.7(16) . . . . ? C1 C3 C5 C11 -174.1(9) . . . . ? C3 C5 C7 C9 -2.9(16) . . . . ? C11 C5 C7 C9 172.0(9) . . . . ? C5 C7 C9 N2 1.8(18) . . . . ? C26 C8 C10 O2 -82.3(13) . . . . ? C25 C8 C10 O2 155.5(10) . . . . ? C26 C8 C10 O4 96.8(13) . . . . ? C25 C8 C10 O4 -25.4(15) . . . . ? C3 C5 C11 C12 12.2(15) . . . . ? C7 C5 C11 C12 -162.5(12) . . . . ? C3 C5 C11 C14 -158.8(10) . . . . ? C7 C5 C11 C14 26.5(14) . . . . ? C14 C11 C12 C13 -7.7(17) . . . . ? C5 C11 C12 C13 -178.6(10) . . . . ? C11 C12 C13 N1 3.1(17) . . . . ? C12 C11 C14 C15 7.0(16) . . . . ? C5 C11 C14 C15 178.2(9) . . . . ? C11 C14 C15 N1 -2.0(17) . . . . ? C28 C6 C16 O3 -52.2(13) . . . . ? C24 C6 C16 O3 -179.2(9) . . . . ? C26 C6 C16 O3 69.0(12) . . . . ? C28 C6 C16 O1 123.6(10) . . . . ? C24 C6 C16 O1 -3.3(12) . . . . ? C26 C6 C16 O1 -115.1(9) . . . . ? C20 C2 C17 O5 -10.7(15) . . . . ? C19 C2 C17 O5 110.4(11) . . . . ? C20 C2 C17 O6 168.9(9) . . . . ? C19 C2 C17 O6 -70.0(13) . . . . ? C19 C4 C18 O7 -102.8(10) . . . . ? C27 C4 C18 O7 133.8(10) . . . . ? C21 C4 C18 O7 13.8(13) . . . . ? C19 C4 C18 O8 70.4(12) . . . . ? C27 C4 C18 O8 -53.1(12) . . . . ? C21 C4 C18 O8 -173.1(8) . . . . ? C18 C4 C19 C2 164.8(9) . . . . ? C27 C4 C19 C2 -75.0(10) . . . . ? C21 C4 C19 C2 42.6(10) . . . . ? C18 C4 C19 C22 45.8(11) . . . . ? C27 C4 C19 C22 166.0(9) . . . . ? C21 C4 C19 C22 -76.3(10) . . . . ? C18 C4 C19 C23 -73.2(12) . . . . ? C27 C4 C19 C23 47.0(12) . . . . ? C21 C4 C19 C23 164.6(9) . . . . ? C20 C2 C19 C4 -40.2(10) . . . . ? C17 C2 C19 C4 -165.8(9) . . . . ? C20 C2 C19 C22 77.3(10) . . . . ? C17 C2 C19 C22 -48.3(12) . . . . ? C20 C2 C19 C23 -163.2(9) . . . . ? C17 C2 C19 C23 71.2(12) . . . . ? C19 C2 C20 C21 21.2(12) . . . . ? C17 C2 C20 C21 147.0(9) . . . . ? C2 C20 C21 C4 5.1(11) . . . . ? C19 C4 C21 C20 -29.4(10) . . . . ? C18 C4 C21 C20 -151.9(9) . . . . ? C27 C4 C21 C20 90.0(10) . . . . ? C28 C6 C24 C25 78.0(11) . . . . ? C16 C6 C24 C25 -157.1(9) . . . . ? C26 C6 C24 C25 -39.3(10) . . . . ? C6 C24 C25 C8 21.7(12) . . . . ? C10 C8 C25 C24 132.3(10) . . . . ? C26 C8 C25 C24 6.7(12) . . . . ? C10 C8 C26 C29 82.8(11) . . . . ? C25 C8 C26 C29 -150.6(9) . . . . ? C10 C8 C26 C30 -41.1(14) . . . . ? C25 C8 C26 C30 85.5(11) . . . . ? C10 C8 C26 C6 -157.6(9) . . . . ? C25 C8 C26 C6 -31.0(10) . . . . ? C28 C6 C26 C8 -75.2(11) . . . . ? C16 C6 C26 C8 164.9(9) . . . . ? C24 C6 C26 C8 43.2(10) . . . . ? C28 C6 C26 C29 43.3(13) . . . . ? C16 C6 C26 C29 -76.6(12) . . . . ? C24 C6 C26 C29 161.7(10) . . . . ? C28 C6 C26 C30 165.1(10) . . . . ? C16 C6 C26 C30 45.3(11) . . . . ? C24 C6 C26 C30 -76.5(10) . . . . ? C14 C15 N1 C13 -2.5(18) . . . . ? C14 C15 N1 Zn2 178.6(9) . . . 1_645 ? C12 C13 N1 C15 2.0(17) . . . . ? C12 C13 N1 Zn2 -179.0(7) . . . 1_645 ? C7 C9 N2 C1 1.4(17) . . . . ? C7 C9 N2 Zn1 177.5(8) . . . . ? C3 C1 N2 C9 -3.7(16) . . . . ? C3 C1 N2 Zn1 -179.9(8) . . . . ? O3 C16 O1 Zn2 -10.5(10) . . . . ? C6 C16 O1 Zn2 173.5(6) . . . . ? O4 C10 O2 Zn2 -42(2) . . . 2_557 ? C8 C10 O2 Zn2 136.9(9) . . . 2_557 ? O2 C10 O4 Zn1 -26.2(17) . . . 2_557 ? C8 C10 O4 Zn1 154.7(7) . . . 2_557 ? O6 C17 O5 Zn1 35.1(19) . . . . ? C2 C17 O5 Zn1 -145.4(8) . . . . ? O5 C17 O6 Zn2 14.4(18) . . . . ? C2 C17 O6 Zn2 -165.2(7) . . . . ? O7 C18 O8 Zn1 7.4(12) . . . 2_556 ? C4 C18 O8 Zn1 -165.6(7) . . . 2_556 ? C17 O5 Zn1 O4 -63.7(13) . . . 2_547 ? C17 O5 Zn1 O8 77.0(13) . . . 2_546 ? C17 O5 Zn1 N2 -168.9(12) . . . . ? C9 N2 Zn1 O4 20.8(9) . . . 2_547 ? C1 N2 Zn1 O4 -163.3(8) . . . 2_547 ? C9 N2 Zn1 O8 -112.2(9) . . . 2_546 ? C1 N2 Zn1 O8 63.7(9) . . . 2_546 ? C9 N2 Zn1 O5 144.0(9) . . . . ? C1 N2 Zn1 O5 -40.1(8) . . . . ? C17 O6 Zn2 O1 79.3(11) . . . . ? C17 O6 Zn2 O2 -48.1(11) . . . 2_547 ? C17 O6 Zn2 N1 -149.8(10) . . . 1_465 ? C16 O1 Zn2 O6 70.0(7) . . . . ? C16 O1 Zn2 O2 -154.2(5) . . . 2_547 ? C16 O1 Zn2 N1 -54.3(6) . . . 1_465 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.735 _refine_diff_density_min -1.156 _refine_diff_density_rms 0.144 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 761488' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 Cu N2 O10' _chemical_formula_weight 654.20 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' _cell_length_a 21.073(4) _cell_length_b 21.073(4) _cell_length_c 6.9309(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3077.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9398 _cell_measurement_theta_min 1.9321 _cell_measurement_theta_max 27.4990 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8614 _exptl_absorpt_correction_T_max 0.8934 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25255 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3532 _reflns_number_gt 3396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.9835P] 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 refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(12) _refine_ls_number_reflns 3532 _refine_ls_number_parameters 232 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C23 C 0.34971(10) 0.52680(10) 0.0092(3) 0.0279(4) Uani 1 1 d . . . H23 H 0.3084 0.5113 0.0121 0.026(6) Uiso 1 1 calc R . . C24 C 0.35936(12) 0.59188(10) 0.0108(4) 0.0365(5) Uani 1 1 d . . . H24 H 0.3251 0.6197 0.0150 0.053(8) Uiso 1 1 calc R . . C25 C 0.42079(12) 0.61462(11) 0.0061(4) 0.0382(5) Uani 1 1 d . . . H25 H 0.4283 0.6581 0.0062 0.045(7) Uiso 1 1 calc R . . C26 C 0.47124(12) 0.57240(10) 0.0013(4) 0.0327(5) Uani 1 1 d . . . H26 H 0.5129 0.5870 -0.0018 0.028(6) Uiso 1 1 calc R . . C27 C 0.45822(10) 0.50798(10) 0.0013(3) 0.0243(4) Uani 1 1 d . . . C28 C 0.27944(9) 0.39488(10) 0.1655(3) 0.0218(4) Uani 1 1 d . . . C29 C 0.20892(9) 0.40371(9) 0.2044(3) 0.0226(4) Uani 1 1 d . . . C30 C 0.17026(11) 0.42794(12) 0.0333(4) 0.0347(6) Uani 1 1 d . . . H30A H 0.1921 0.4191 -0.0870 0.060(9) Uiso 1 1 calc R . . H30B H 0.1636 0.4734 0.0434 0.049(8) Uiso 1 1 calc R . . C31 C 0.10650(10) 0.39232(11) 0.0414(3) 0.0317(5) Uani 1 1 d . . . H31A H 0.0714 0.4217 0.0262 0.038(7) Uiso 1 1 calc R . . H31B H 0.1042 0.3607 -0.0602 0.057(9) Uiso 1 1 calc R . . C32 C 0.10400(10) 0.36043(9) 0.2405(3) 0.0245(4) Uani 1 1 d . . . C33 C 0.07881(11) 0.40789(11) 0.3906(4) 0.0359(6) Uani 1 1 d . . . H33A H 0.0357 0.4187 0.3604 0.035(7) Uiso 1 1 calc R . . H33B H 0.1044 0.4455 0.3886 0.034(6) Uiso 1 1 calc R . . H33C H 0.0806 0.3891 0.5166 0.040(7) Uiso 1 1 calc R . . C34 C 0.17553(10) 0.34282(9) 0.2795(3) 0.0235(4) Uani 1 1 d . . . C35 C 0.19600(11) 0.28493(10) 0.1610(4) 0.0300(5) Uani 1 1 d . . . H35A H 0.2407 0.2780 0.1775 0.038(7) Uiso 1 1 calc R . . H35B H 0.1870 0.2923 0.0271 0.040(7) Uiso 1 1 calc R . . H35C H 0.1731 0.2482 0.2042 0.031(6) Uiso 1 1 calc R . . C36 C 0.19044(11) 0.32966(11) 0.4924(4) 0.0326(5) Uani 1 1 d . . . H36A H 0.1644 0.2954 0.5377 0.049(8) Uiso 1 1 calc R . . H36B H 0.1819 0.3670 0.5673 0.055(9) Uiso 1 1 calc R . . H36C H 0.2344 0.3184 0.5055 0.053(8) Uiso 1 1 calc R . . C37 C 0.06234(9) 0.30123(10) 0.2355(3) 0.0252(4) Uani 1 1 d . . . Cu1 Cu 0.390605(10) 0.390605(10) 0.0000 0.01850(10) Uani 1 2 d S . . H1A H 0.9271(9) 0.1944(13) 0.291(2) 0.043(8) Uiso 1 1 d D . . H2A H 0.9238(9) 0.2027(12) 0.471(2) 0.039(8) Uiso 1 1 d D . . H3A H 0.2041(13) 0.4313(12) 0.310(4) 0.043(8) Uiso 1 1 d . . . H4A H 0.0155(14) 0.2576(14) 0.392(5) 0.047(9) Uiso 1 1 d . . . N1 N 0.39793(8) 0.48564(7) 0.0034(2) 0.0221(3) Uani 1 1 d . . . O1 O 0.31837(7) 0.39207(8) 0.30031(19) 0.0281(3) Uani 1 1 d . . . O2 O 0.29821(6) 0.39166(7) -0.01080(19) 0.0223(3) Uani 1 1 d . . . O3 O 0.05166(8) 0.27051(8) 0.0920(2) 0.0328(4) Uani 1 1 d . . . O4 O 0.03914(9) 0.28554(9) 0.4064(2) 0.0393(5) Uani 1 1 d . . . O5 O 0.95177(7) 0.19919(7) 0.3854(2) 0.0252(3) Uani 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 C23 0.0323(11) 0.0245(10) 0.0268(10) -0.0025(10) -0.0013(10) -0.0011(9) C24 0.0511(14) 0.0255(11) 0.0329(11) -0.0012(10) 0.0008(12) -0.0010(11) C25 0.0615(15) 0.0213(10) 0.0319(11) 0.0003(11) 0.0039(11) -0.0118(11) C26 0.0443(13) 0.0288(12) 0.0251(10) -0.0005(11) 0.0030(11) -0.0155(10) C27 0.0297(10) 0.0279(10) 0.0155(8) -0.0017(9) -0.0002(9) -0.0126(8) C28 0.0227(9) 0.0186(9) 0.0240(9) 0.0023(8) 0.0018(7) -0.0004(9) C29 0.0204(9) 0.0221(10) 0.0254(11) 0.0016(8) 0.0011(7) 0.0003(8) C30 0.0218(11) 0.0386(13) 0.0436(15) 0.0155(11) -0.0029(10) -0.0016(9) C31 0.0241(10) 0.0312(11) 0.0399(12) 0.0067(9) -0.0054(9) -0.0020(11) C32 0.0200(9) 0.0243(9) 0.0291(10) -0.0018(8) 0.0027(10) 0.0000(8) C33 0.0259(12) 0.0304(13) 0.0514(16) -0.0141(11) 0.0045(11) -0.0006(10) C34 0.0224(10) 0.0198(9) 0.0282(11) 0.0001(8) 0.0032(9) 0.0013(8) C35 0.0248(11) 0.0226(11) 0.0427(13) -0.0049(9) 0.0034(10) 0.0016(9) C36 0.0314(11) 0.0353(12) 0.0310(11) 0.0067(11) 0.0034(11) -0.0038(10) C37 0.0177(9) 0.0280(10) 0.0301(11) -0.0027(9) 0.0026(9) -0.0004(8) Cu1 0.01877(12) 0.01877(12) 0.01795(15) 0.00021(9) -0.00021(9) -0.00334(14) N1 0.0286(9) 0.0203(8) 0.0174(7) -0.0008(7) 0.0000(10) -0.0070(7) O1 0.0226(7) 0.0396(9) 0.0222(7) 0.0008(7) -0.0021(5) 0.0030(7) O2 0.0224(6) 0.0251(7) 0.0193(6) 0.0018(8) 0.0008(5) -0.0032(6) O3 0.0305(9) 0.0373(10) 0.0304(8) -0.0072(7) 0.0036(7) -0.0076(7) O4 0.0447(11) 0.0424(11) 0.0309(9) -0.0061(8) 0.0108(8) -0.0204(9) O5 0.0246(8) 0.0302(8) 0.0209(7) 0.0020(6) 0.0040(6) -0.0014(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 C23 N1 1.336(3) . ? C23 C24 1.386(3) . ? C24 C25 1.381(3) . ? C25 C26 1.387(3) . ? C26 C27 1.385(3) . ? C27 N1 1.355(2) . ? C27 C27 1.483(4) 6 ? C28 O1 1.245(2) . ? C28 O2 1.286(2) . ? C28 C29 1.522(3) . ? C29 C30 1.527(3) . ? C29 C34 1.553(3) . ? C30 C31 1.540(3) . ? C31 C32 1.536(3) . ? C32 C37 1.526(3) . ? C32 C33 1.538(3) . ? C32 C34 1.576(3) . ? C34 C35 1.532(3) . ? C34 C36 1.534(3) . ? C37 O3 1.207(3) . ? C37 O4 1.324(3) . ? Cu1 O2 1.9485(13) 6 ? Cu1 O2 1.9485(13) . ? Cu1 N1 2.0088(16) 6 ? Cu1 N1 2.0088(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 N1 C23 C24 122.1(2) . . ? C25 C24 C23 118.7(2) . . ? C24 C25 C26 119.79(19) . . ? C27 C26 C25 118.5(2) . . ? N1 C27 C26 121.8(2) . . ? N1 C27 C27 114.68(11) . 6 ? C26 C27 C27 123.57(13) . 6 ? O1 C28 O2 120.53(18) . . ? O1 C28 C29 121.07(17) . . ? O2 C28 C29 118.39(17) . . ? C28 C29 C30 115.09(17) . . ? C28 C29 C34 113.63(16) . . ? C30 C29 C34 107.14(17) . . ? C29 C30 C31 105.90(18) . . ? C32 C31 C30 106.04(17) . . ? C37 C32 C31 110.91(18) . . ? C37 C32 C33 110.42(17) . . ? C31 C32 C33 109.58(18) . . ? C37 C32 C34 111.21(16) . . ? C31 C32 C34 102.95(16) . . ? C33 C32 C34 111.56(17) . . ? C35 C34 C36 108.29(18) . . ? C35 C34 C29 110.53(17) . . ? C36 C34 C29 112.25(17) . . ? C35 C34 C32 111.41(17) . . ? C36 C34 C32 113.79(17) . . ? C29 C34 C32 100.46(15) . . ? O3 C37 O4 122.29(19) . . ? O3 C37 C32 124.4(2) . . ? O4 C37 C32 113.33(19) . . ? O2 Cu1 O2 91.39(8) 6 . ? O2 Cu1 N1 93.78(7) 6 6 ? O2 Cu1 N1 174.18(6) . 6 ? O2 Cu1 N1 174.18(6) 6 . ? O2 Cu1 N1 93.78(7) . . ? N1 Cu1 N1 81.20(10) 6 . ? C23 N1 C27 119.19(17) . . ? C23 N1 Cu1 126.08(14) . . ? C27 N1 Cu1 114.72(14) . . ? C28 O2 Cu1 105.75(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C23 C24 C25 0.1(4) . . . . ? C23 C24 C25 C26 -0.5(4) . . . . ? C24 C25 C26 C27 0.0(4) . . . . ? C25 C26 C27 N1 0.8(4) . . . . ? C25 C26 C27 C27 -179.3(3) . . . 6 ? O1 C28 C29 C30 160.6(2) . . . . ? O2 C28 C29 C30 -18.0(3) . . . . ? O1 C28 C29 C34 -75.3(3) . . . . ? O2 C28 C29 C34 106.1(2) . . . . ? C28 C29 C30 C31 141.61(19) . . . . ? C34 C29 C30 C31 14.2(2) . . . . ? C29 C30 C31 C32 12.7(2) . . . . ? C30 C31 C32 C37 -153.14(18) . . . . ? C30 C31 C32 C33 84.7(2) . . . . ? C30 C31 C32 C34 -34.1(2) . . . . ? C28 C29 C34 C35 -44.9(2) . . . . ? C30 C29 C34 C35 83.4(2) . . . . ? C28 C29 C34 C36 76.1(2) . . . . ? C30 C29 C34 C36 -155.61(19) . . . . ? C28 C29 C34 C32 -162.62(16) . . . . ? C30 C29 C34 C32 -34.4(2) . . . . ? C37 C32 C34 C35 43.1(2) . . . . ? C31 C32 C34 C35 -75.7(2) . . . . ? C33 C32 C34 C35 166.91(19) . . . . ? C37 C32 C34 C36 -79.6(2) . . . . ? C31 C32 C34 C36 161.57(18) . . . . ? C33 C32 C34 C36 44.1(2) . . . . ? C37 C32 C34 C29 160.24(17) . . . . ? C31 C32 C34 C29 41.42(19) . . . . ? C33 C32 C34 C29 -76.0(2) . . . . ? C31 C32 C37 O3 24.8(3) . . . . ? C33 C32 C37 O3 146.4(2) . . . . ? C34 C32 C37 O3 -89.2(3) . . . . ? C31 C32 C37 O4 -156.22(19) . . . . ? C33 C32 C37 O4 -34.5(3) . . . . ? C34 C32 C37 O4 89.9(2) . . . . ? C24 C23 N1 C27 0.8(3) . . . . ? C24 C23 N1 Cu1 -179.91(17) . . . . ? C26 C27 N1 C23 -1.2(3) . . . . ? C27 C27 N1 C23 178.9(2) 6 . . . ? C26 C27 N1 Cu1 179.37(18) . . . . ? C27 C27 N1 Cu1 -0.5(3) 6 . . . ? O2 Cu1 N1 C23 -148.8(5) 6 . . . ? O2 Cu1 N1 C23 3.79(19) . . . . ? N1 Cu1 N1 C23 -179.2(2) 6 . . . ? O2 Cu1 N1 C27 30.6(7) 6 . . . ? O2 Cu1 N1 C27 -176.85(15) . . . . ? N1 Cu1 N1 C27 0.21(12) 6 . . . ? O1 C28 O2 Cu1 -5.1(2) . . . . ? C29 C28 O2 Cu1 173.47(14) . . . . ? O2 Cu1 O2 C28 90.78(13) 6 . . . ? N1 Cu1 O2 C28 -116.6(6) 6 . . . ? N1 Cu1 O2 C28 -86.54(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.393 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.046 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 761489' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 N6 O8 Zn3' _chemical_formula_weight 826.76 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0548(18) _cell_length_b 9.1122(18) _cell_length_c 11.912(2) _cell_angle_alpha 107.17(3) _cell_angle_beta 104.62(3) _cell_angle_gamma 93.42(3) _cell_volume 899.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5283 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.50 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 2.041 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6857 _exptl_absorpt_correction_T_max 0.7773 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8802 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.1097 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4074 _reflns_number_gt 2538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1016P)^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 refu _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.043(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4074 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2070 _refine_ls_wR_factor_gt 0.1797 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.5932(8) 0.3030(7) 0.7334(6) 0.0441(15) Uani 1 1 d . . . C2 C 0.6014(8) 0.4615(8) 0.7567(6) 0.0467(16) Uani 1 1 d . . . C3 C 0.6503(12) 0.5689(9) 0.8763(8) 0.078(3) Uani 1 1 d . . . H3 H 0.6599 0.6757 0.8916 0.094 Uiso 1 1 calc R . . C4 C 0.6826(14) 0.5038(10) 0.9682(8) 0.097(4) Uani 1 1 d . . . H4 H 0.7129 0.5690 1.0490 0.117 Uiso 1 1 calc R . . C5 C 0.6720(13) 0.3448(10) 0.9458(8) 0.088(3) Uani 1 1 d . . . H5 H 0.6960 0.3082 1.0124 0.106 Uiso 1 1 calc R . . C6 C 0.6282(9) 0.2402(8) 0.8312(7) 0.058(2) Uani 1 1 d . . . H6 H 0.6215 0.1338 0.8176 0.070 Uiso 1 1 calc R . . C7 C 0.3346(7) -0.1155(7) 0.6879(6) 0.0404(14) Uani 1 1 d . A . C8 C 0.2213(7) -0.0403(7) 0.7532(6) 0.0387(14) Uani 1 1 d . . . C9 C 0.1841(8) 0.1102(7) 0.7259(9) 0.061(2) Uani 1 1 d . A . H9A H 0.2566 0.1984 0.7849 0.073 Uiso 1 1 calc R . . H9B H 0.1898 0.1037 0.6444 0.073 Uiso 1 1 calc R . . C10 C 0.0209(8) 0.1272(8) 0.7353(8) 0.0548(19) Uani 1 1 d . . . H10A H -0.0427 0.1402 0.6611 0.066 Uiso 1 1 calc R A . H10B H 0.0226 0.2175 0.8040 0.066 Uiso 1 1 calc R . . C11 C -0.0447(7) -0.0207(7) 0.7539(6) 0.0372(13) Uani 1 1 d . A . C12 C 0.2973(15) 0.0023(16) 0.8858(13) 0.043(4) Uani 0.467(13) 1 d P A 1 H12A H 0.3269 -0.0886 0.9055 0.064 Uiso 0.467(13) 1 calc PR A 1 H12B H 0.2271 0.0458 0.9306 0.064 Uiso 0.467(13) 1 calc PR A 1 H12C H 0.3873 0.0774 0.9077 0.064 Uiso 0.467(13) 1 calc PR A 1 C13 C 0.0611(7) -0.1441(6) 0.7085(6) 0.0387(14) Uani 1 1 d . A . C14 C 0.0080(8) -0.2125(9) 0.5690(7) 0.0572(19) Uani 1 1 d . . . H14A H 0.0779 -0.2805 0.5418 0.086 Uiso 1 1 calc R A . H14B H 0.0064 -0.1301 0.5340 0.086 Uiso 1 1 calc R . . H14C H -0.0937 -0.2699 0.5435 0.086 Uiso 1 1 calc R . . C15 C 0.0598(9) -0.2742(9) 0.7640(8) 0.061(2) Uani 1 1 d . . . H15A H -0.0444 -0.3230 0.7450 0.092 Uiso 1 1 calc R A . H15B H 0.1027 -0.2323 0.8513 0.092 Uiso 1 1 calc R . . H15C H 0.1203 -0.3495 0.7308 0.092 Uiso 1 1 calc R . . C16 C -0.2129(7) -0.0790(6) 0.6835(6) 0.0350(13) Uani 1 1 d . . . C12' C -0.0236(16) 0.014(2) 0.8886(14) 0.067(5) Uani 0.533(13) 1 d P A 2 H12D H -0.0864 0.0912 0.9151 0.100 Uiso 0.533(13) 1 calc PR A 2 H12E H 0.0828 0.0532 0.9323 0.100 Uiso 0.533(13) 1 calc PR A 2 H12F H -0.0535 -0.0786 0.9045 0.100 Uiso 0.533(13) 1 calc PR A 2 N1 N 0.5585(7) 0.4862(6) 0.6455(5) 0.0466(14) Uani 1 1 d . . . N3 N 0.5253(5) 0.3466(5) 0.5607(4) 0.0366(12) Uani 1 1 d . . . N4 N 0.5461(6) 0.2341(5) 0.6116(5) 0.0375(12) Uani 1 1 d . . . O1 O 0.3748(6) -0.2395(5) 0.7052(5) 0.0557(13) Uani 1 1 d . . . O2 O 0.3893(6) -0.0550(5) 0.6226(5) 0.0534(12) Uani 1 1 d . . . O3 O -0.2736(5) -0.1847(5) 0.7140(4) 0.0501(12) Uani 1 1 d . . . O4 O -0.2799(5) -0.0260(5) 0.6033(4) 0.0458(11) Uani 1 1 d . . . Zn1 Zn 0.5000 0.0000 0.5000 0.0355(3) Uani 1 2 d S . . Zn2 Zn 0.52926(8) -0.30704(7) 0.62099(7) 0.0372(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(4) 0.030(3) 0.046(4) 0.008(3) 0.011(3) 0.008(3) C2 0.060(4) 0.039(3) 0.043(4) 0.018(3) 0.010(3) 0.014(3) C3 0.127(8) 0.039(4) 0.055(5) 0.005(4) 0.014(5) 0.011(5) C4 0.172(11) 0.052(5) 0.044(5) 0.005(4) 0.002(6) 0.017(6) C5 0.150(10) 0.050(5) 0.045(5) 0.017(4) -0.009(5) 0.014(5) C6 0.073(5) 0.032(3) 0.069(5) 0.024(4) 0.009(4) 0.008(3) C7 0.032(3) 0.037(3) 0.046(4) 0.010(3) 0.008(3) 0.000(3) C8 0.028(3) 0.035(3) 0.048(4) 0.010(3) 0.007(3) 0.003(2) C9 0.050(4) 0.031(3) 0.106(7) 0.023(4) 0.030(4) 0.004(3) C10 0.044(4) 0.040(4) 0.075(5) 0.012(4) 0.016(4) 0.001(3) C11 0.031(3) 0.032(3) 0.044(4) 0.008(3) 0.009(3) 0.002(2) C12 0.029(7) 0.049(8) 0.044(9) 0.008(6) 0.010(6) -0.003(6) C13 0.036(3) 0.027(3) 0.056(4) 0.011(3) 0.021(3) 0.006(2) C14 0.046(4) 0.048(4) 0.062(5) -0.003(3) 0.014(4) 0.009(3) C15 0.046(4) 0.055(4) 0.101(7) 0.048(5) 0.024(4) 0.017(4) C16 0.033(3) 0.024(3) 0.046(4) 0.006(3) 0.014(3) 0.002(2) C12' 0.040(8) 0.092(12) 0.065(10) 0.013(8) 0.025(7) 0.014(8) N1 0.058(4) 0.026(2) 0.052(4) 0.010(2) 0.013(3) 0.003(2) N3 0.044(3) 0.019(2) 0.047(3) 0.013(2) 0.010(2) 0.006(2) N4 0.038(3) 0.020(2) 0.056(4) 0.015(2) 0.014(2) 0.000(2) O1 0.055(3) 0.044(3) 0.082(4) 0.031(3) 0.029(3) 0.016(2) O2 0.056(3) 0.046(3) 0.059(3) 0.015(2) 0.021(3) 0.000(2) O3 0.040(3) 0.049(3) 0.062(3) 0.026(2) 0.007(2) -0.003(2) O4 0.036(2) 0.042(2) 0.059(3) 0.019(2) 0.010(2) 0.006(2) Zn1 0.0372(6) 0.0205(5) 0.0485(7) 0.0115(4) 0.0112(5) 0.0041(4) Zn2 0.0388(5) 0.0231(4) 0.0500(5) 0.0123(3) 0.0123(3) 0.0055(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 C1 N4 1.341(8) . ? C1 C2 1.381(9) . ? C1 C6 1.420(9) . ? C2 N1 1.372(8) . ? C2 C3 1.411(11) . ? C3 C4 1.371(11) . ? C3 H3 0.9300 . ? C4 C5 1.386(11) . ? C4 H4 0.9300 . ? C5 C6 1.358(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O2 1.253(7) . ? C7 O1 1.266(7) . ? C7 C8 1.516(8) . ? C8 C12 1.475(15) . ? C8 C9 1.537(8) . ? C8 C13 1.560(8) . ? C9 C10 1.524(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.538(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12' 1.499(15) . ? C11 C16 1.517(8) . ? C11 C13 1.583(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C15 1.519(8) . ? C13 C14 1.526(9) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O4 1.237(7) . ? C16 O3 1.267(7) . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? N1 N3 1.331(7) . ? N1 Zn2 2.013(5) 1_565 ? N3 N4 1.336(6) . ? N3 Zn2 2.009(5) 2_656 ? N4 Zn1 2.105(5) . ? O1 Zn2 1.946(5) . ? O2 Zn1 2.121(5) . ? O3 Zn2 1.922(5) 1_455 ? O4 Zn1 2.129(4) 1_455 ? Zn1 N4 2.105(5) 2_656 ? Zn1 O2 2.121(5) 2_656 ? Zn1 O4 2.129(4) 2_556 ? Zn1 O4 2.129(4) 1_655 ? Zn2 O3 1.922(5) 1_655 ? Zn2 N3 2.009(5) 2_656 ? Zn2 N1 2.013(5) 1_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 C2 108.1(5) . . ? N4 C1 C6 131.3(6) . . ? C2 C1 C6 120.6(6) . . ? N1 C2 C1 107.1(6) . . ? N1 C2 C3 130.1(6) . . ? C1 C2 C3 122.7(6) . . ? C4 C3 C2 114.9(7) . . ? C4 C3 H3 122.6 . . ? C2 C3 H3 122.6 . . ? C3 C4 C5 122.8(8) . . ? C3 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C6 C5 C4 123.0(8) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C5 C6 C1 115.9(6) . . ? C5 C6 H6 122.0 . . ? C1 C6 H6 122.0 . . ? O2 C7 O1 121.5(6) . . ? O2 C7 C8 121.4(5) . . ? O1 C7 C8 117.0(6) . . ? C12 C8 C7 106.9(7) . . ? C12 C8 C9 107.3(8) . . ? C7 C8 C9 111.7(5) . . ? C12 C8 C13 114.7(7) . . ? C7 C8 C13 112.3(5) . . ? C9 C8 C13 103.9(5) . . ? C10 C9 C8 106.3(5) . . ? C10 C9 H9A 110.5 . . ? C8 C9 H9A 110.5 . . ? C10 C9 H9B 110.5 . . ? C8 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C9 C10 C11 107.7(5) . . ? C9 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? C9 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? C12' C11 C16 110.2(7) . . ? C12' C11 C10 107.2(8) . . ? C16 C11 C10 114.2(5) . . ? C12' C11 C13 110.4(7) . . ? C16 C11 C13 110.7(5) . . ? C10 C11 C13 104.0(5) . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? C15 C13 C14 109.5(6) . . ? C15 C13 C8 112.9(6) . . ? C14 C13 C8 111.1(5) . . ? C15 C13 C11 112.0(5) . . ? C14 C13 C11 110.0(5) . . ? C8 C13 C11 101.2(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 O3 125.0(6) . . ? O4 C16 C11 121.0(5) . . ? O3 C16 C11 114.0(5) . . ? C11 C12' H12D 109.5 . . ? C11 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? N3 N1 C2 106.3(5) . . ? N3 N1 Zn2 127.9(4) . 1_565 ? C2 N1 Zn2 125.4(4) . 1_565 ? N1 N3 N4 111.3(5) . . ? N1 N3 Zn2 125.1(4) . 2_656 ? N4 N3 Zn2 123.3(4) . 2_656 ? N3 N4 C1 107.1(5) . . ? N3 N4 Zn1 120.0(4) . . ? C1 N4 Zn1 132.9(4) . . ? C7 O1 Zn2 109.6(4) . . ? C7 O2 Zn1 167.4(4) . . ? C16 O3 Zn2 123.0(4) . 1_455 ? C16 O4 Zn1 144.3(4) . 1_455 ? N4 Zn1 N4 180.00(14) . 2_656 ? N4 Zn1 O2 90.69(19) . 2_656 ? N4 Zn1 O2 89.31(19) 2_656 2_656 ? N4 Zn1 O2 89.31(19) . . ? N4 Zn1 O2 90.69(19) 2_656 . ? O2 Zn1 O2 180.000(1) 2_656 . ? N4 Zn1 O4 92.99(18) . 2_556 ? N4 Zn1 O4 87.01(18) 2_656 2_556 ? O2 Zn1 O4 92.22(18) 2_656 2_556 ? O2 Zn1 O4 87.78(18) . 2_556 ? N4 Zn1 O4 87.01(18) . 1_655 ? N4 Zn1 O4 92.99(18) 2_656 1_655 ? O2 Zn1 O4 87.78(18) 2_656 1_655 ? O2 Zn1 O4 92.22(18) . 1_655 ? O4 Zn1 O4 180.0(3) 2_556 1_655 ? O3 Zn2 O1 109.7(2) 1_655 . ? O3 Zn2 N3 115.6(2) 1_655 2_656 ? O1 Zn2 N3 118.3(2) . 2_656 ? O3 Zn2 N1 102.0(2) 1_655 1_545 ? O1 Zn2 N1 102.7(2) . 1_545 ? N3 Zn2 N1 106.16(19) 2_656 1_545 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 N1 -0.3(8) . . . . ? C6 C1 C2 N1 -178.7(7) . . . . ? N4 C1 C2 C3 -178.8(8) . . . . ? C6 C1 C2 C3 2.8(12) . . . . ? N1 C2 C3 C4 179.1(9) . . . . ? C1 C2 C3 C4 -2.8(14) . . . . ? C2 C3 C4 C5 1.6(18) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C4 C5 C6 C1 0.1(16) . . . . ? N4 C1 C6 C5 -179.4(8) . . . . ? C2 C1 C6 C5 -1.3(12) . . . . ? O2 C7 C8 C12 -115.8(8) . . . . ? O1 C7 C8 C12 62.1(9) . . . . ? O2 C7 C8 C9 1.2(9) . . . . ? O1 C7 C8 C9 179.1(6) . . . . ? O2 C7 C8 C13 117.5(7) . . . . ? O1 C7 C8 C13 -64.6(8) . . . . ? C12 C8 C9 C10 -92.2(8) . . . . ? C7 C8 C9 C10 150.9(6) . . . . ? C13 C8 C9 C10 29.6(8) . . . . ? C8 C9 C10 C11 -6.1(8) . . . . ? C9 C10 C11 C12' 97.6(8) . . . . ? C9 C10 C11 C16 -140.0(6) . . . . ? C9 C10 C11 C13 -19.3(7) . . . . ? C12 C8 C13 C15 -43.7(9) . . . . ? C7 C8 C13 C15 78.7(7) . . . . ? C9 C8 C13 C15 -160.4(6) . . . . ? C12 C8 C13 C14 -167.1(7) . . . . ? C7 C8 C13 C14 -44.8(7) . . . . ? C9 C8 C13 C14 76.1(6) . . . . ? C12 C8 C13 C11 76.2(8) . . . . ? C7 C8 C13 C11 -161.5(5) . . . . ? C9 C8 C13 C11 -40.6(6) . . . . ? C12' C11 C13 C15 42.4(10) . . . . ? C16 C11 C13 C15 -79.8(7) . . . . ? C10 C11 C13 C15 157.1(6) . . . . ? C12' C11 C13 C14 164.4(8) . . . . ? C16 C11 C13 C14 42.2(7) . . . . ? C10 C11 C13 C14 -80.9(6) . . . . ? C12' C11 C13 C8 -78.1(8) . . . . ? C16 C11 C13 C8 159.7(5) . . . . ? C10 C11 C13 C8 36.6(6) . . . . ? C12' C11 C16 O4 132.4(9) . . . . ? C10 C11 C16 O4 11.7(8) . . . . ? C13 C11 C16 O4 -105.3(6) . . . . ? C12' C11 C16 O3 -48.3(9) . . . . ? C10 C11 C16 O3 -169.0(5) . . . . ? C13 C11 C16 O3 74.1(6) . . . . ? C1 C2 N1 N3 0.5(7) . . . . ? C3 C2 N1 N3 178.9(9) . . . . ? C1 C2 N1 Zn2 174.1(5) . . . 1_565 ? C3 C2 N1 Zn2 -7.6(12) . . . 1_565 ? C2 N1 N3 N4 -0.6(7) . . . . ? Zn2 N1 N3 N4 -173.9(4) 1_565 . . . ? C2 N1 N3 Zn2 -175.0(4) . . . 2_656 ? Zn2 N1 N3 Zn2 11.7(8) 1_565 . . 2_656 ? N1 N3 N4 C1 0.5(7) . . . . ? Zn2 N3 N4 C1 175.0(4) 2_656 . . . ? N1 N3 N4 Zn1 179.3(4) . . . . ? Zn2 N3 N4 Zn1 -6.2(6) 2_656 . . . ? C2 C1 N4 N3 -0.1(7) . . . . ? C6 C1 N4 N3 178.1(7) . . . . ? C2 C1 N4 Zn1 -178.7(5) . . . . ? C6 C1 N4 Zn1 -0.5(12) . . . . ? O2 C7 O1 Zn2 1.4(8) . . . . ? C8 C7 O1 Zn2 -176.5(4) . . . . ? O1 C7 O2 Zn1 13(3) . . . . ? C8 C7 O2 Zn1 -169.3(18) . . . . ? O4 C16 O3 Zn2 11.4(8) . . . 1_455 ? C11 C16 O3 Zn2 -167.9(4) . . . 1_455 ? O3 C16 O4 Zn1 20.6(11) . . . 1_455 ? C11 C16 O4 Zn1 -160.2(5) . . . 1_455 ? N3 N4 Zn1 N4 -126(100) . . . 2_656 ? C1 N4 Zn1 N4 52(100) . . . 2_656 ? N3 N4 Zn1 O2 43.3(4) . . . 2_656 ? C1 N4 Zn1 O2 -138.3(6) . . . 2_656 ? N3 N4 Zn1 O2 -136.7(4) . . . . ? C1 N4 Zn1 O2 41.7(6) . . . . ? N3 N4 Zn1 O4 -49.0(4) . . . 2_556 ? C1 N4 Zn1 O4 129.4(6) . . . 2_556 ? N3 N4 Zn1 O4 131.0(4) . . . 1_655 ? C1 N4 Zn1 O4 -50.6(6) . . . 1_655 ? C7 O2 Zn1 N4 -149(2) . . . . ? C7 O2 Zn1 N4 31(2) . . . 2_656 ? C7 O2 Zn1 O2 59(100) . . . 2_656 ? C7 O2 Zn1 O4 118(2) . . . 2_556 ? C7 O2 Zn1 O4 -62(2) . . . 1_655 ? C7 O1 Zn2 O3 77.9(5) . . . 1_655 ? C7 O1 Zn2 N3 -57.7(5) . . . 2_656 ? C7 O1 Zn2 N1 -174.2(4) . . . 1_545 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.081 _refine_diff_density_min -1.319 _refine_diff_density_rms 0.147 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 761490' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 Co3 N6 O8' _chemical_formula_weight 807.44 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' O O 0.0106 0.0060 '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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0109(18) _cell_length_b 9.0814(18) _cell_length_c 11.788(2) _cell_angle_alpha 106.73(3) _cell_angle_beta 103.76(3) _cell_angle_gamma 95.01(3) _cell_volume 884.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5524 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 413 _exptl_absorpt_coefficient_mu 1.447 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7607 _exptl_absorpt_correction_T_max 0.8342 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8817 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.1123 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4031 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+3.9354P] 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 SHELXL _refine_ls_extinction_coef 0.020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4031 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1150 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1978 _refine_ls_wR_factor_gt 0.1756 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 C1 C 0.8309(7) 0.3748(8) 0.1881(6) 0.0309(14) Uani 1 1 d . A . C2 C 0.7197(7) 0.4582(8) 0.2497(6) 0.0297(14) Uani 1 1 d . . . C3 C 0.7949(15) 0.5066(17) 0.3856(13) 0.040(4) Uani 0.518(15) 1 d P A 1 H3A H 0.8041 0.4155 0.4109 0.059 Uiso 0.518(15) 1 calc PR A 1 H3B H 0.7327 0.5691 0.4289 0.059 Uiso 0.518(15) 1 calc PR A 1 H3C H 0.8960 0.5661 0.4042 0.059 Uiso 0.518(15) 1 calc PR A 1 C4 C 0.5468(9) 0.2293(10) 0.2706(9) 0.053(2) Uani 1 1 d . . . H4A H 0.6081 0.1531 0.2414 0.079 Uiso 1 1 calc R A . H4B H 0.4411 0.1798 0.2503 0.079 Uiso 1 1 calc R . . H4C H 0.5862 0.2753 0.3584 0.079 Uiso 1 1 calc R . . C5 C 0.5550(7) 0.3563(7) 0.2096(6) 0.0307(14) Uani 1 1 d . A . C6 C 0.5030(9) 0.2797(10) 0.0685(7) 0.049(2) Uani 1 1 d . . . H6A H 0.5064 0.3589 0.0296 0.074 Uiso 1 1 calc R A . H6B H 0.3991 0.2238 0.0439 0.074 Uiso 1 1 calc R . . H6C H 0.5711 0.2087 0.0442 0.074 Uiso 1 1 calc R . . C7 C 0.4540(7) 0.4835(8) 0.2503(6) 0.0303(14) Uani 1 1 d . . . C8 C 0.2846(7) 0.4279(7) 0.1816(6) 0.0294(14) Uani 1 1 d . A . C9 C 0.5287(8) 0.6304(8) 0.2317(8) 0.0411(17) Uani 1 1 d . A . H9A H 0.5370 0.7211 0.3022 0.049 Uiso 1 1 calc R . . H9B H 0.4660 0.6469 0.1587 0.049 Uiso 1 1 calc R . . C10 C 0.6908(8) 0.6055(8) 0.2172(8) 0.0445(19) Uani 1 1 d . A . H10A H 0.6938 0.5926 0.1332 0.053 Uiso 1 1 calc R . . H10B H 0.7685 0.6938 0.2723 0.053 Uiso 1 1 calc R . . C11 C 1.0951(8) 0.8046(8) 0.2367(6) 0.0318(14) Uani 1 1 d . . . C12 C 1.1295(10) 0.7426(9) 0.3359(7) 0.0477(19) Uani 1 1 d . . . H12 H 1.1205 0.6358 0.3227 0.057 Uiso 1 1 calc R . . C13 C 1.1760(12) 0.8471(10) 0.4503(8) 0.063(3) Uani 1 1 d . . . H13 H 1.2035 0.8109 0.5173 0.076 Uiso 1 1 calc R . . C14 C 1.1844(14) 1.0089(10) 0.4723(8) 0.072(3) Uani 1 1 d . . . H14 H 1.2146 1.0753 0.5533 0.087 Uiso 1 1 calc R . . C15 C 1.1501(12) 1.0710(9) 0.3798(8) 0.062(3) Uani 1 1 d . . . H15 H 1.1570 1.1780 0.3947 0.074 Uiso 1 1 calc R . . C16 C 1.1038(8) 0.9650(8) 0.2603(6) 0.0350(15) Uani 1 1 d . . . C3' C 0.4697(16) 0.523(2) 0.3851(13) 0.045(5) Uani 0.482(15) 1 d P A 2 H3'1 H 0.4136 0.6058 0.4101 0.067 Uiso 0.482(15) 1 calc PR A 2 H3'2 H 0.5772 0.5549 0.4301 0.067 Uiso 0.482(15) 1 calc PR A 2 H3'3 H 0.4284 0.4325 0.4018 0.067 Uiso 0.482(15) 1 calc PR A 2 Co1 Co 1.0000 0.5000 0.0000 0.0248(3) Uani 1 2 d S . . Co2 Co 0.97917(10) 0.80681(10) -0.12060(8) 0.0285(3) Uani 1 1 d . . . N1 N 1.0468(6) 0.7352(6) 0.1131(5) 0.0267(11) Uani 1 1 d . . . N2 N 1.0287(6) 0.8482(6) 0.0615(5) 0.0290(12) Uani 1 1 d . . . N3 N 1.0609(7) 0.9887(6) 0.1486(5) 0.0341(13) Uani 1 1 d . . . O1 O 0.8997(5) 0.4310(6) 0.1258(4) 0.0396(12) Uani 1 1 d . . . O2 O 0.8607(6) 0.2473(6) 0.2069(5) 0.0453(13) Uani 1 1 d . . . O3 O 0.2218(5) 0.4821(5) 0.0993(4) 0.0344(11) Uani 1 1 d . . . O4 O 0.2176(5) 0.3232(6) 0.2116(5) 0.0368(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(3) 0.034(4) 0.036(4) 0.011(3) 0.009(3) 0.004(3) C2 0.021(3) 0.033(3) 0.035(3) 0.009(3) 0.009(3) 0.003(3) C3 0.025(7) 0.051(9) 0.049(9) 0.024(7) 0.012(6) 0.009(6) C4 0.039(4) 0.061(5) 0.086(6) 0.053(5) 0.027(4) 0.020(4) C5 0.031(3) 0.027(3) 0.034(3) 0.008(3) 0.011(3) 0.006(3) C6 0.045(4) 0.048(5) 0.040(4) -0.005(4) 0.008(3) 0.012(4) C7 0.025(3) 0.033(3) 0.037(4) 0.015(3) 0.010(3) 0.008(3) C8 0.028(3) 0.028(3) 0.030(3) 0.005(3) 0.006(3) 0.008(3) C9 0.028(3) 0.031(4) 0.065(5) 0.014(4) 0.015(3) 0.008(3) C10 0.037(4) 0.030(4) 0.071(5) 0.014(4) 0.025(4) 0.007(3) C11 0.032(3) 0.027(3) 0.034(4) 0.010(3) 0.006(3) 0.006(3) C12 0.064(5) 0.035(4) 0.045(4) 0.021(4) 0.006(4) 0.008(4) C13 0.096(7) 0.053(5) 0.036(4) 0.024(4) -0.001(5) 0.006(5) C14 0.123(9) 0.038(5) 0.039(5) 0.001(4) 0.006(5) 0.011(5) C15 0.095(7) 0.024(4) 0.048(5) -0.003(4) 0.006(5) 0.002(4) C16 0.046(4) 0.029(3) 0.029(3) 0.009(3) 0.007(3) 0.008(3) C3' 0.025(7) 0.073(12) 0.030(8) 0.006(8) 0.005(6) 0.013(7) Co1 0.0225(6) 0.0212(6) 0.0329(7) 0.0114(5) 0.0077(5) 0.0046(5) Co2 0.0281(5) 0.0204(5) 0.0380(5) 0.0100(4) 0.0100(4) 0.0040(3) N1 0.029(3) 0.022(3) 0.032(3) 0.010(2) 0.010(2) 0.008(2) N2 0.032(3) 0.022(2) 0.036(3) 0.011(2) 0.011(2) 0.009(2) N3 0.039(3) 0.024(3) 0.038(3) 0.007(2) 0.014(3) 0.009(2) O1 0.034(3) 0.046(3) 0.044(3) 0.017(2) 0.017(2) 0.007(2) O2 0.037(3) 0.044(3) 0.072(4) 0.031(3) 0.026(3) 0.016(2) O3 0.023(2) 0.035(3) 0.045(3) 0.017(2) 0.004(2) 0.005(2) O4 0.023(2) 0.041(3) 0.049(3) 0.020(2) 0.009(2) 0.001(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 C1 O1 1.250(8) . ? C1 O2 1.279(8) . ? C1 C2 1.506(9) . ? C2 C3 1.498(15) . ? C2 C10 1.521(9) . ? C2 C5 1.568(9) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.530(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.541(9) . ? C5 C7 1.570(9) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C3' 1.493(15) . ? C7 C8 1.511(9) . ? C7 C9 1.537(9) . ? C8 O3 1.252(7) . ? C8 O4 1.261(8) . ? C9 C10 1.539(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.354(8) . ? C11 C16 1.393(9) . ? C11 C12 1.421(9) . ? C12 C13 1.349(11) . ? C12 H12 0.9300 . ? C13 C14 1.408(12) . ? C13 H13 0.9300 . ? C14 C15 1.352(12) . ? C14 H14 0.9300 . ? C15 C16 1.397(10) . ? C15 H15 0.9300 . ? C16 N3 1.366(8) . ? C3' H3'1 0.9600 . ? C3' H3'2 0.9600 . ? C3' H3'3 0.9600 . ? Co1 O3 2.108(4) 2_665 ? Co1 O3 2.108(4) 1_655 ? Co1 N1 2.110(5) . ? Co1 N1 2.110(5) 2_765 ? Co1 O1 2.117(5) 2_765 ? Co1 O1 2.117(5) . ? Co2 O4 1.921(5) 2_665 ? Co2 O2 1.973(5) 2_765 ? Co2 N2 1.999(5) . ? Co2 N3 2.025(5) 2_775 ? N1 N2 1.338(7) . ? N2 N3 1.344(7) . ? N3 Co2 2.025(5) 2_775 ? O2 Co2 1.973(5) 2_765 ? O3 Co1 2.108(4) 1_455 ? O4 Co2 1.921(5) 2_665 ? 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 C1 O2 120.0(6) . . ? O1 C1 C2 121.8(6) . . ? O2 C1 C2 118.0(6) . . ? C3 C2 C1 106.3(7) . . ? C3 C2 C10 107.4(8) . . ? C1 C2 C10 112.8(6) . . ? C3 C2 C5 113.3(7) . . ? C1 C2 C5 112.4(5) . . ? C10 C2 C5 104.6(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C4 C5 C6 109.0(6) . . ? C4 C5 C2 113.6(5) . . ? C6 C5 C2 109.9(6) . . ? C4 C5 C7 112.5(6) . . ? C6 C5 C7 110.4(5) . . ? C2 C5 C7 101.3(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3' C7 C8 108.4(7) . . ? C3' C7 C9 106.5(9) . . ? C8 C7 C9 115.1(5) . . ? C3' C7 C5 110.2(8) . . ? C8 C7 C5 111.5(5) . . ? C9 C7 C5 105.0(5) . . ? O3 C8 O4 124.7(6) . . ? O3 C8 C7 120.4(6) . . ? O4 C8 C7 114.9(6) . . ? C7 C9 C10 107.7(5) . . ? C7 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? C7 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? C2 C10 C9 105.6(6) . . ? C2 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? C2 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.8 . . ? N1 C11 C16 107.9(6) . . ? N1 C11 C12 131.9(6) . . ? C16 C11 C12 120.2(6) . . ? C13 C12 C11 116.3(7) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? C12 C13 C14 122.7(8) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C15 C14 C13 122.2(8) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 116.1(7) . . ? C14 C15 H15 121.9 . . ? C16 C15 H15 121.9 . . ? N3 C16 C11 106.8(6) . . ? N3 C16 C15 130.8(7) . . ? C11 C16 C15 122.5(7) . . ? C7 C3' H3'1 109.5 . . ? C7 C3' H3'2 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? C7 C3' H3'3 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? O3 Co1 O3 180.0(3) 2_665 1_655 ? O3 Co1 N1 93.62(19) 2_665 . ? O3 Co1 N1 86.38(19) 1_655 . ? O3 Co1 N1 86.38(19) 2_665 2_765 ? O3 Co1 N1 93.62(19) 1_655 2_765 ? N1 Co1 N1 180.0(3) . 2_765 ? O3 Co1 O1 90.59(18) 2_665 2_765 ? O3 Co1 O1 89.41(18) 1_655 2_765 ? N1 Co1 O1 88.9(2) . 2_765 ? N1 Co1 O1 91.1(2) 2_765 2_765 ? O3 Co1 O1 89.41(18) 2_665 . ? O3 Co1 O1 90.59(18) 1_655 . ? N1 Co1 O1 91.1(2) . . ? N1 Co1 O1 88.9(2) 2_765 . ? O1 Co1 O1 180.0 2_765 . ? O4 Co2 O2 111.2(2) 2_665 2_765 ? O4 Co2 N2 114.1(2) 2_665 . ? O2 Co2 N2 119.9(2) 2_765 . ? O4 Co2 N3 100.6(2) 2_665 2_775 ? O2 Co2 N3 101.9(2) 2_765 2_775 ? N2 Co2 N3 106.1(2) . 2_775 ? N2 N1 C11 107.4(5) . . ? N2 N1 Co1 119.7(4) . . ? C11 N1 Co1 132.9(4) . . ? N1 N2 N3 110.5(5) . . ? N1 N2 Co2 122.8(4) . . ? N3 N2 Co2 126.5(4) . . ? N2 N3 C16 107.4(5) . . ? N2 N3 Co2 126.1(4) . 2_775 ? C16 N3 Co2 125.9(4) . 2_775 ? C1 O1 Co1 172.3(5) . . ? C1 O2 Co2 103.1(4) . 2_765 ? C8 O3 Co1 140.4(4) . 1_455 ? C8 O4 Co2 126.1(4) . 2_665 ? 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 O1 C1 C2 C3 -111.9(9) . . . . ? O2 C1 C2 C3 64.2(9) . . . . ? O1 C1 C2 C10 5.5(9) . . . . ? O2 C1 C2 C10 -178.4(6) . . . . ? O1 C1 C2 C5 123.6(7) . . . . ? O2 C1 C2 C5 -60.4(8) . . . . ? C3 C2 C5 C4 -44.1(9) . . . . ? C1 C2 C5 C4 76.5(7) . . . . ? C10 C2 C5 C4 -160.8(6) . . . . ? C3 C2 C5 C6 -166.6(8) . . . . ? C1 C2 C5 C6 -46.0(7) . . . . ? C10 C2 C5 C6 76.8(7) . . . . ? C3 C2 C5 C7 76.7(8) . . . . ? C1 C2 C5 C7 -162.7(5) . . . . ? C10 C2 C5 C7 -39.9(6) . . . . ? C4 C5 C7 C3' 40.8(10) . . . . ? C6 C5 C7 C3' 162.8(9) . . . . ? C2 C5 C7 C3' -80.8(9) . . . . ? C4 C5 C7 C8 -79.6(7) . . . . ? C6 C5 C7 C8 42.4(8) . . . . ? C2 C5 C7 C8 158.8(5) . . . . ? C4 C5 C7 C9 155.2(6) . . . . ? C6 C5 C7 C9 -82.8(7) . . . . ? C2 C5 C7 C9 33.5(6) . . . . ? C3' C7 C8 O3 131.6(9) . . . . ? C9 C7 C8 O3 12.5(9) . . . . ? C5 C7 C8 O3 -106.9(7) . . . . ? C3' C7 C8 O4 -50.3(10) . . . . ? C9 C7 C8 O4 -169.4(6) . . . . ? C5 C7 C8 O4 71.2(7) . . . . ? C3' C7 C9 C10 101.4(8) . . . . ? C8 C7 C9 C10 -138.4(6) . . . . ? C5 C7 C9 C10 -15.5(8) . . . . ? C3 C2 C10 C9 -89.6(8) . . . . ? C1 C2 C10 C9 153.6(6) . . . . ? C5 C2 C10 C9 31.1(8) . . . . ? C7 C9 C10 C2 -9.7(8) . . . . ? N1 C11 C12 C13 179.9(8) . . . . ? C16 C11 C12 C13 -2.7(12) . . . . ? C11 C12 C13 C14 2.6(15) . . . . ? C12 C13 C14 C15 -1.7(18) . . . . ? C13 C14 C15 C16 0.7(17) . . . . ? N1 C11 C16 N3 -0.4(8) . . . . ? C12 C11 C16 N3 -178.4(7) . . . . ? N1 C11 C16 C15 179.9(8) . . . . ? C12 C11 C16 C15 1.9(12) . . . . ? C14 C15 C16 N3 179.5(9) . . . . ? C14 C15 C16 C11 -0.9(14) . . . . ? C16 C11 N1 N2 1.0(7) . . . . ? C12 C11 N1 N2 178.7(7) . . . . ? C16 C11 N1 Co1 -178.9(5) . . . . ? C12 C11 N1 Co1 -1.3(12) . . . . ? O3 Co1 N1 N2 -51.8(4) 2_665 . . . ? O3 Co1 N1 N2 128.2(4) 1_655 . . . ? N1 Co1 N1 N2 -122(100) 2_765 . . . ? O1 Co1 N1 N2 38.8(4) 2_765 . . . ? O1 Co1 N1 N2 -141.2(4) . . . . ? O3 Co1 N1 C11 128.2(6) 2_665 . . . ? O3 Co1 N1 C11 -51.8(6) 1_655 . . . ? N1 Co1 N1 C11 58(100) 2_765 . . . ? O1 Co1 N1 C11 -141.3(6) 2_765 . . . ? O1 Co1 N1 C11 38.7(6) . . . . ? C11 N1 N2 N3 -1.3(7) . . . . ? Co1 N1 N2 N3 178.7(4) . . . . ? C11 N1 N2 Co2 173.6(4) . . . . ? Co1 N1 N2 Co2 -6.4(6) . . . . ? O4 Co2 N2 N1 63.4(5) 2_665 . . . ? O2 Co2 N2 N1 -72.3(5) 2_765 . . . ? N3 Co2 N2 N1 173.3(4) 2_775 . . . ? O4 Co2 N2 N3 -122.6(5) 2_665 . . . ? O2 Co2 N2 N3 101.8(5) 2_765 . . . ? N3 Co2 N2 N3 -12.7(6) 2_775 . . . ? N1 N2 N3 C16 1.0(7) . . . . ? Co2 N2 N3 C16 -173.7(4) . . . . ? N1 N2 N3 Co2 -170.2(4) . . . 2_775 ? Co2 N2 N3 Co2 15.1(8) . . . 2_775 ? C11 C16 N3 N2 -0.3(7) . . . . ? C15 C16 N3 N2 179.3(9) . . . . ? C11 C16 N3 Co2 170.9(5) . . . 2_775 ? C15 C16 N3 Co2 -9.5(12) . . . 2_775 ? O2 C1 O1 Co1 67(4) . . . . ? C2 C1 O1 Co1 -117(3) . . . . ? O3 Co1 O1 C1 63(3) 2_665 . . . ? O3 Co1 O1 C1 -117(3) 1_655 . . . ? N1 Co1 O1 C1 157(3) . . . . ? N1 Co1 O1 C1 -23(3) 2_765 . . . ? O1 Co1 O1 C1 -73(100) 2_765 . . . ? O1 C1 O2 Co2 0.6(7) . . . 2_765 ? C2 C1 O2 Co2 -175.5(5) . . . 2_765 ? O4 C8 O3 Co1 19.9(11) . . . 1_455 ? C7 C8 O3 Co1 -162.3(5) . . . 1_455 ? O3 C8 O4 Co2 13.1(9) . . . 2_665 ? C7 C8 O4 Co2 -164.9(4) . . . 2_665 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.751 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.141