# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Enrique Colacio' _publ_contact_author_email ECOLACIO@UGR.ES _publ_section_title ; Double and Triple Stranded Mesocates Containing the Bis(bidentate) Bridging Ligand 1,3-bis(pyridine-2-carboxamide)benzene. Structure, Properties and DNA Interaction ; loop_ _publ_author_name 'Enrique Colacio' 'Joan Cano' 'Juan Herrera' 'Virtudes Moreno' 'Antonio J. Mota' 'M Angeles Palacios' ; A.Rodriguez-Dieguez ; 'A Sironi' data_4 _database_code_depnum_ccdc_archive 'CCDC 721059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H74 Co2 N12 O25' _chemical_formula_weight 1409.11 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 monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.347(3) _cell_length_b 22.288(5) _cell_length_c 18.484(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.15(3) _cell_angle_gamma 90.00 _cell_volume 6322(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 2.204 _cell_measurement_theta_max 23.619 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 40065 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 23.74 _reflns_number_total 9603 _reflns_number_gt 8206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+37.5312P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9603 _refine_ls_number_parameters 838 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1653 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.38285(4) 0.19508(3) 0.79954(4) 0.01578(18) Uani 1 1 d . . . Co2 Co 0.38744(5) 0.18343(3) 0.42937(4) 0.01907(19) Uani 1 1 d . . . N1 N 0.4664(3) 0.15225(19) 0.8589(2) 0.0201(10) Uani 1 1 d . . . C2 C 0.4499(4) 0.1188(3) 0.9173(3) 0.0276(13) Uani 1 1 d . . . H2 H 0.3926 0.1143 0.9326 0.033 Uiso 1 1 calc R . . C3 C 0.5154(4) 0.0908(3) 0.9553(3) 0.0324(15) Uani 1 1 d . . . H3 H 0.5021 0.0683 0.9962 0.039 Uiso 1 1 calc R . . C4 C 0.6000(4) 0.0960(3) 0.9333(3) 0.0328(15) Uani 1 1 d . . . H4 H 0.6449 0.0770 0.9582 0.039 Uiso 1 1 calc R . . C5 C 0.6166(4) 0.1308(3) 0.8719(3) 0.0258(13) Uani 1 1 d . . . H5 H 0.6734 0.1354 0.8553 0.031 Uiso 1 1 calc R . . C6 C 0.5498(3) 0.1577(2) 0.8368(3) 0.0190(12) Uani 1 1 d . . . C7 C 0.5613(3) 0.1953(2) 0.7703(3) 0.0197(12) Uani 1 1 d . . . O8 O 0.6364(2) 0.20251(17) 0.7447(2) 0.0243(9) Uani 1 1 d . . . N9 N 0.4873(3) 0.21720(19) 0.7452(2) 0.0162(9) Uani 1 1 d . . . C10 C 0.4905(3) 0.2493(2) 0.6784(3) 0.0166(11) Uani 1 1 d . . . C11 C 0.4982(3) 0.2163(2) 0.6150(3) 0.0155(11) Uani 1 1 d . . . H11 H 0.5077 0.1752 0.6174 0.019 Uiso 1 1 calc R . . C12 C 0.4826(3) 0.3113(2) 0.6751(3) 0.0173(11) Uani 1 1 d . . . H12 H 0.4789 0.3339 0.7173 0.021 Uiso 1 1 calc R . . C13 C 0.4805(3) 0.3393(2) 0.6079(3) 0.0206(12) Uani 1 1 d . . . H13 H 0.4773 0.3809 0.6054 0.025 Uiso 1 1 calc R . . C14 C 0.4831(3) 0.3062(2) 0.5445(3) 0.0167(11) Uani 1 1 d . . . H14 H 0.4792 0.3254 0.4999 0.020 Uiso 1 1 calc R . . C15 C 0.4916(3) 0.2444(2) 0.5480(3) 0.0167(11) Uani 1 1 d . . . N16 N 0.4912(3) 0.20777(19) 0.4841(2) 0.0178(10) Uani 1 1 d . . . O17 O 0.6364(2) 0.18333(17) 0.4981(2) 0.0254(9) Uani 1 1 d . . . C18 C 0.5640(4) 0.1800(2) 0.4669(3) 0.0200(12) Uani 1 1 d . . . C19 C 0.5538(4) 0.1399(2) 0.4027(3) 0.0232(12) Uani 1 1 d . . . C20 C 0.6220(4) 0.1080(3) 0.3736(3) 0.0286(14) Uani 1 1 d . . . H20 H 0.6772 0.1100 0.3944 0.034 Uiso 1 1 calc R . . C21 C 0.6075(4) 0.0729(3) 0.3132(3) 0.0364(16) Uani 1 1 d . . . H21 H 0.6523 0.0503 0.2932 0.044 Uiso 1 1 calc R . . C22 C 0.5258(4) 0.0721(3) 0.2835(3) 0.0336(15) Uani 1 1 d . . . H22 H 0.5152 0.0500 0.2417 0.040 Uiso 1 1 calc R . . C23 C 0.4587(4) 0.1041(3) 0.3156(3) 0.0290(14) Uani 1 1 d . . . H23 H 0.4031 0.1022 0.2956 0.035 Uiso 1 1 calc R . . N24 N 0.4723(3) 0.1375(2) 0.3747(2) 0.0232(10) Uani 1 1 d . . . N31 N 0.3977(3) 0.26963(19) 0.8535(2) 0.0183(10) Uani 1 1 d . . . C32 C 0.4494(4) 0.2792(3) 0.9101(3) 0.0246(13) Uani 1 1 d . . . H32 H 0.4806 0.2471 0.9293 0.030 Uiso 1 1 calc R . . C33 C 0.4583(4) 0.3347(3) 0.9411(3) 0.0319(14) Uani 1 1 d . . . H33 H 0.4951 0.3400 0.9806 0.038 Uiso 1 1 calc R . . C34 C 0.4117(4) 0.3830(3) 0.9130(3) 0.0347(15) Uani 1 1 d . . . H34 H 0.4158 0.4210 0.9336 0.042 Uiso 1 1 calc R . . C35 C 0.3595(4) 0.3728(3) 0.8537(3) 0.0270(13) Uani 1 1 d . . . H35 H 0.3286 0.4044 0.8329 0.032 Uiso 1 1 calc R . . C36 C 0.3526(4) 0.3160(2) 0.8248(3) 0.0235(13) Uani 1 1 d . . . C37 C 0.2970(3) 0.3009(2) 0.7616(3) 0.0203(12) Uani 1 1 d . . . O38 O 0.2524(3) 0.34076(16) 0.7316(2) 0.0267(9) Uani 1 1 d . . . N39 N 0.3028(3) 0.24373(19) 0.7423(2) 0.0178(10) Uani 1 1 d . . . C40 C 0.2587(3) 0.2260(2) 0.6772(3) 0.0184(11) Uani 1 1 d . . . C41 C 0.2952(3) 0.2431(2) 0.6120(3) 0.0180(11) Uani 1 1 d . . . H41 H 0.3427 0.2689 0.6117 0.022 Uiso 1 1 calc R . . C42 C 0.1842(3) 0.1914(2) 0.6779(3) 0.0211(12) Uani 1 1 d . . . H42 H 0.1585 0.1806 0.7215 0.025 Uiso 1 1 calc R . . C43 C 0.1479(3) 0.1726(2) 0.6128(3) 0.0242(13) Uani 1 1 d . . . H43 H 0.0966 0.1504 0.6130 0.029 Uiso 1 1 calc R . . C44 C 0.1874(3) 0.1867(2) 0.5475(3) 0.0234(12) Uani 1 1 d . . . H44 H 0.1639 0.1724 0.5044 0.028 Uiso 1 1 calc R . . C45 C 0.2616(3) 0.2219(2) 0.5465(3) 0.0184(11) Uani 1 1 d . . . N46 N 0.3070(3) 0.23563(19) 0.4817(2) 0.0191(10) Uani 1 1 d . . . O47 O 0.2605(3) 0.33380(17) 0.4869(2) 0.0280(9) Uani 1 1 d . . . C48 C 0.3037(3) 0.2919(2) 0.4591(3) 0.0208(12) Uani 1 1 d . . . C49 C 0.3568(3) 0.3030(2) 0.3930(3) 0.0208(12) Uani 1 1 d . . . C50 C 0.3602(4) 0.3573(3) 0.3586(3) 0.0277(13) Uani 1 1 d . . . H50 H 0.3303 0.3902 0.3770 0.033 Uiso 1 1 calc R . . C51 C 0.4095(4) 0.3626(3) 0.2953(3) 0.0344(15) Uani 1 1 d . . . H51 H 0.4130 0.3991 0.2710 0.041 Uiso 1 1 calc R . . C52 C 0.4526(4) 0.3130(3) 0.2700(3) 0.0345(15) Uani 1 1 d . . . H52 H 0.4846 0.3151 0.2275 0.041 Uiso 1 1 calc R . . C53 C 0.4479(4) 0.2596(3) 0.3083(3) 0.0290(14) Uani 1 1 d . . . H53 H 0.4785 0.2265 0.2915 0.035 Uiso 1 1 calc R . . N54 N 0.4006(3) 0.2542(2) 0.3688(2) 0.0228(10) Uani 1 1 d . . . N61 N 0.2827(3) 0.16906(19) 0.8561(2) 0.0215(10) Uani 1 1 d . . . C62 C 0.2453(4) 0.1973(3) 0.9111(3) 0.0331(15) Uani 1 1 d . . . H62 H 0.2698 0.2328 0.9280 0.040 Uiso 1 1 calc R . . C63 C 0.1711(5) 0.1754(3) 0.9440(4) 0.053(2) Uani 1 1 d . . . H63 H 0.1464 0.1957 0.9828 0.064 Uiso 1 1 calc R . . C64 C 0.1342(5) 0.1233(3) 0.9189(4) 0.050(2) Uani 1 1 d . . . H64 H 0.0838 0.1082 0.9400 0.060 Uiso 1 1 calc R . . C65 C 0.1723(4) 0.0939(3) 0.8626(4) 0.0336(15) Uani 1 1 d . . . H65 H 0.1482 0.0586 0.8447 0.040 Uiso 1 1 calc R . . C66 C 0.2472(3) 0.1173(2) 0.8324(3) 0.0221(12) Uani 1 1 d . . . C67 C 0.2928(3) 0.0890(2) 0.7705(3) 0.0193(12) Uani 1 1 d . . . O68 O 0.2657(2) 0.04025(16) 0.7451(2) 0.0242(9) Uani 1 1 d . . . N69 N 0.3603(3) 0.12066(18) 0.7474(2) 0.0165(9) Uani 1 1 d . . . C70 C 0.4042(3) 0.0997(2) 0.6841(3) 0.0174(11) Uani 1 1 d . . . C71 C 0.3644(3) 0.1077(2) 0.6175(3) 0.0165(11) Uani 1 1 d . . . H71 H 0.3077 0.1224 0.6155 0.020 Uiso 1 1 calc R . . C72 C 0.4861(3) 0.0736(2) 0.6872(3) 0.0199(12) Uani 1 1 d . . . H72 H 0.5131 0.0671 0.7316 0.024 Uiso 1 1 calc R . . C73 C 0.5277(3) 0.0569(2) 0.6233(3) 0.0210(12) Uani 1 1 d . . . H73 H 0.5819 0.0384 0.6255 0.025 Uiso 1 1 calc R . . C74 C 0.4895(3) 0.0677(2) 0.5567(3) 0.0189(12) Uani 1 1 d . . . H74 H 0.5182 0.0573 0.5143 0.023 Uiso 1 1 calc R . . C75 C 0.4076(3) 0.0944(2) 0.5541(3) 0.0192(12) Uani 1 1 d . . . N76 N 0.3666(3) 0.11102(19) 0.4869(2) 0.0198(10) Uani 1 1 d . . . O77 O 0.2843(3) 0.02463(18) 0.4874(2) 0.0367(11) Uani 1 1 d . . . C78 C 0.3063(4) 0.0747(3) 0.4618(3) 0.0262(13) Uani 1 1 d . . . C79 C 0.2584(4) 0.0996(3) 0.3978(3) 0.0290(14) Uani 1 1 d . . . C80 C 0.1855(5) 0.0722(3) 0.3692(4) 0.0475(19) Uani 1 1 d . . . H80 H 0.1661 0.0356 0.3871 0.057 Uiso 1 1 calc R . . C81 C 0.1423(5) 0.1003(3) 0.3133(5) 0.063(2) Uani 1 1 d . . . H81 H 0.0931 0.0830 0.2925 0.075 Uiso 1 1 calc R . . C82 C 0.1734(5) 0.1551(3) 0.2884(4) 0.054(2) Uani 1 1 d . . . H82 H 0.1452 0.1749 0.2508 0.065 Uiso 1 1 calc R . . C83 C 0.2462(4) 0.1799(3) 0.3198(3) 0.0369(16) Uani 1 1 d . . . H83 H 0.2669 0.2164 0.3027 0.044 Uiso 1 1 calc R . . N84 N 0.2882(3) 0.1528(2) 0.3747(2) 0.0249(11) Uani 1 1 d . . . O1W O 0.4096(4) 0.9739(2) 0.8832(3) 0.0568(14) Uani 1 1 d . . . O2W O 0.4050(5) 0.0550(3) 0.1225(3) 0.086(2) Uani 1 1 d . . . O3W O 0.3104(4) 0.0408(3) 0.9941(3) 0.0711(18) Uani 1 1 d . . . O4W O 0.2825(6) 0.0060(4) 0.2095(7) 0.174(6) Uani 1 1 d . . . O5W O 0.2538(3) 0.90878(19) 0.4427(2) 0.0373(11) Uani 1 1 d . . . O6W O 0.1883(3) 0.94773(18) 0.8167(2) 0.0329(10) Uani 1 1 d . . . O7W O 0.1929(3) 0.0089(2) 0.6143(3) 0.0431(12) Uani 1 1 d . . . O8W O 0.1198(4) 0.0234(3) 0.1450(5) 0.107(3) Uani 1 1 d . . . O9W O 0.9801(4) 0.0285(3) 0.2281(4) 0.081(2) Uani 1 1 d . . . O10W O 0.2027(6) 0.1251(4) 0.1043(5) 0.111(3) Uani 1 1 d . . . O11W O 0.3828(3) 0.2588(2) 0.0839(3) 0.0643(16) Uani 1 1 d . . . O12W O 0.4192(3) 0.3791(2) 0.1015(3) 0.0477(12) Uani 1 1 d . . . O13W O 0.4509(4) 0.4605(3) 0.4625(4) 0.086(2) Uani 1 1 d . . . O14W O 0.4815(5) 0.5269(3) 0.8578(5) 0.106(3) Uani 1 1 d . . . O15W O 0.3058(4) 0.4458(2) 0.5346(3) 0.0514(13) Uani 1 1 d . . . O16W O 0.4707(3) 0.1690(2) 0.1515(3) 0.0551(14) Uani 1 1 d . . . O17W O 0.7042(3) 0.2469(2) 0.6153(2) 0.0345(10) Uani 1 1 d . . . O18W O 0.7239(3) 0.0946(2) 0.7103(3) 0.0442(12) Uani 1 1 d . . . O19W O 0.1459(3) 0.35103(19) 0.6099(2) 0.0341(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0168(4) 0.0140(4) 0.0165(4) 0.0010(3) 0.0011(3) 0.0004(3) Co2 0.0225(4) 0.0179(4) 0.0168(4) -0.0022(3) -0.0031(3) 0.0029(3) N1 0.024(3) 0.019(2) 0.017(2) 0.0018(19) 0.0007(19) 0.001(2) C2 0.026(3) 0.028(3) 0.028(3) 0.010(3) 0.001(3) -0.001(3) C3 0.036(4) 0.031(3) 0.031(3) 0.021(3) -0.003(3) -0.005(3) C4 0.033(4) 0.029(3) 0.037(4) 0.010(3) -0.011(3) 0.004(3) C5 0.023(3) 0.027(3) 0.028(3) 0.003(3) -0.003(3) 0.000(3) C6 0.022(3) 0.016(3) 0.019(3) -0.001(2) 0.000(2) -0.002(2) C7 0.024(3) 0.016(3) 0.019(3) -0.002(2) -0.003(2) -0.003(2) O8 0.016(2) 0.030(2) 0.027(2) 0.0068(17) 0.0007(16) -0.0012(16) N9 0.016(2) 0.016(2) 0.017(2) 0.0015(18) 0.0003(18) 0.0015(18) C10 0.012(3) 0.019(3) 0.018(3) 0.003(2) 0.000(2) -0.002(2) C11 0.010(2) 0.017(3) 0.019(3) 0.000(2) 0.001(2) -0.003(2) C12 0.018(3) 0.017(3) 0.017(3) 0.000(2) 0.001(2) -0.002(2) C13 0.023(3) 0.013(3) 0.025(3) 0.003(2) 0.002(2) 0.000(2) C14 0.013(3) 0.018(3) 0.019(3) 0.003(2) -0.004(2) 0.001(2) C15 0.015(3) 0.018(3) 0.017(3) -0.001(2) 0.000(2) 0.000(2) N16 0.021(2) 0.016(2) 0.016(2) -0.0002(18) 0.0008(18) 0.0013(19) O17 0.021(2) 0.026(2) 0.029(2) -0.0023(17) 0.0002(17) 0.0023(17) C18 0.023(3) 0.014(3) 0.023(3) 0.005(2) 0.006(2) 0.001(2) C19 0.029(3) 0.021(3) 0.020(3) 0.005(2) 0.004(2) 0.001(2) C20 0.029(3) 0.025(3) 0.032(3) -0.001(3) 0.006(3) 0.002(3) C21 0.046(4) 0.025(3) 0.037(4) -0.006(3) 0.020(3) 0.003(3) C22 0.052(4) 0.025(3) 0.023(3) -0.001(3) 0.007(3) 0.005(3) C23 0.046(4) 0.023(3) 0.019(3) -0.002(2) -0.003(3) 0.005(3) N24 0.032(3) 0.020(2) 0.018(2) -0.0017(19) -0.001(2) 0.003(2) N31 0.019(2) 0.021(2) 0.016(2) -0.0016(19) 0.0040(19) 0.0016(19) C32 0.027(3) 0.024(3) 0.023(3) -0.003(2) -0.001(2) 0.008(2) C33 0.034(3) 0.037(4) 0.025(3) -0.009(3) -0.010(3) 0.000(3) C34 0.045(4) 0.025(3) 0.034(4) -0.010(3) -0.002(3) -0.001(3) C35 0.035(3) 0.019(3) 0.027(3) -0.003(2) 0.000(3) 0.004(3) C36 0.031(3) 0.024(3) 0.016(3) 0.001(2) 0.007(2) 0.001(3) C37 0.020(3) 0.018(3) 0.024(3) 0.000(2) 0.004(2) -0.001(2) O38 0.035(2) 0.018(2) 0.028(2) -0.0012(17) -0.0059(18) 0.0099(18) N39 0.019(2) 0.017(2) 0.017(2) -0.0009(18) -0.0009(18) 0.0005(18) C40 0.018(3) 0.015(3) 0.022(3) -0.002(2) -0.003(2) 0.005(2) C41 0.014(3) 0.012(3) 0.028(3) -0.002(2) -0.005(2) 0.002(2) C42 0.020(3) 0.018(3) 0.025(3) 0.000(2) 0.000(2) 0.001(2) C43 0.015(3) 0.023(3) 0.035(3) 0.000(3) -0.004(2) -0.002(2) C44 0.020(3) 0.022(3) 0.028(3) -0.002(2) -0.007(2) 0.000(2) C45 0.021(3) 0.016(3) 0.018(3) 0.000(2) -0.001(2) 0.007(2) N46 0.020(2) 0.020(2) 0.018(2) -0.0009(19) -0.0052(19) 0.0035(19) O47 0.035(2) 0.021(2) 0.028(2) 0.0021(17) 0.0036(18) 0.0068(18) C48 0.018(3) 0.018(3) 0.027(3) -0.007(2) -0.008(2) 0.000(2) C49 0.020(3) 0.022(3) 0.020(3) 0.001(2) -0.007(2) 0.001(2) C50 0.029(3) 0.025(3) 0.029(3) 0.000(3) -0.006(3) 0.001(3) C51 0.036(4) 0.032(4) 0.035(4) 0.012(3) 0.002(3) 0.002(3) C52 0.035(4) 0.043(4) 0.025(3) 0.006(3) 0.003(3) 0.005(3) C53 0.036(3) 0.030(3) 0.021(3) 0.002(3) 0.000(3) 0.006(3) N54 0.025(3) 0.022(2) 0.021(3) 0.000(2) -0.004(2) 0.005(2) N61 0.023(2) 0.018(2) 0.024(3) 0.004(2) 0.006(2) 0.004(2) C62 0.043(4) 0.016(3) 0.040(4) -0.003(3) 0.020(3) -0.002(3) C63 0.057(5) 0.026(4) 0.077(5) -0.014(4) 0.049(4) -0.005(3) C64 0.048(4) 0.023(4) 0.080(6) -0.005(3) 0.045(4) -0.003(3) C65 0.025(3) 0.017(3) 0.059(4) -0.001(3) 0.016(3) -0.003(3) C66 0.021(3) 0.016(3) 0.030(3) 0.005(2) 0.002(2) -0.001(2) C67 0.016(3) 0.019(3) 0.023(3) 0.004(2) -0.004(2) 0.002(2) O68 0.029(2) 0.017(2) 0.027(2) -0.0017(17) 0.0009(17) -0.0053(17) N69 0.016(2) 0.013(2) 0.020(2) 0.0014(18) -0.0010(18) -0.0001(18) C70 0.020(3) 0.012(3) 0.021(3) -0.002(2) 0.003(2) -0.003(2) C71 0.018(3) 0.008(2) 0.024(3) -0.001(2) 0.001(2) 0.001(2) C72 0.022(3) 0.015(3) 0.022(3) 0.002(2) -0.002(2) -0.001(2) C73 0.018(3) 0.015(3) 0.030(3) -0.001(2) 0.002(2) 0.004(2) C74 0.022(3) 0.013(3) 0.022(3) 0.000(2) 0.003(2) 0.003(2) C75 0.025(3) 0.011(3) 0.022(3) 0.000(2) -0.002(2) 0.001(2) N76 0.023(2) 0.018(2) 0.019(2) -0.0030(19) -0.0026(19) -0.0003(19) O77 0.049(3) 0.026(2) 0.035(2) -0.0028(19) -0.009(2) -0.012(2) C78 0.030(3) 0.023(3) 0.025(3) -0.006(3) -0.005(3) 0.002(3) C79 0.034(3) 0.021(3) 0.032(3) -0.007(3) -0.011(3) 0.000(3) C80 0.056(5) 0.030(4) 0.056(5) -0.002(3) -0.030(4) -0.009(3) C81 0.065(5) 0.042(4) 0.080(6) 0.000(4) -0.052(5) -0.013(4) C82 0.067(5) 0.042(4) 0.054(5) -0.003(4) -0.040(4) -0.002(4) C83 0.046(4) 0.029(3) 0.036(4) -0.002(3) -0.019(3) 0.002(3) N84 0.026(3) 0.023(3) 0.026(3) -0.009(2) -0.010(2) 0.005(2) O1W 0.062(3) 0.058(3) 0.050(3) -0.002(3) 0.001(3) -0.012(3) O2W 0.116(5) 0.091(5) 0.051(4) -0.004(3) 0.008(3) -0.062(4) O3W 0.065(4) 0.081(4) 0.067(4) 0.035(3) -0.013(3) -0.035(3) O4W 0.125(7) 0.126(7) 0.272(13) 0.135(8) 0.124(8) 0.076(6) O5W 0.037(2) 0.031(2) 0.044(3) -0.005(2) -0.009(2) 0.005(2) O6W 0.037(2) 0.026(2) 0.037(2) 0.0031(19) -0.0009(19) -0.0019(19) O7W 0.050(3) 0.033(3) 0.046(3) 0.002(2) -0.005(2) -0.014(2) O8W 0.070(4) 0.066(4) 0.186(8) 0.026(5) 0.031(5) 0.004(4) O9W 0.051(3) 0.090(5) 0.102(5) 0.026(4) -0.032(3) -0.021(3) O10W 0.123(7) 0.088(5) 0.123(7) 0.015(5) 0.027(5) 0.008(5) O11W 0.042(3) 0.052(3) 0.098(5) 0.021(3) 0.006(3) 0.002(3) O12W 0.046(3) 0.048(3) 0.049(3) -0.008(2) -0.001(2) -0.002(2) O13W 0.084(5) 0.084(5) 0.089(5) -0.009(4) 0.005(4) -0.002(4) O14W 0.071(4) 0.095(5) 0.152(7) -0.058(5) -0.002(4) -0.020(4) O15W 0.075(4) 0.036(3) 0.044(3) -0.005(2) -0.014(3) 0.008(3) O16W 0.052(3) 0.050(3) 0.063(3) 0.009(3) 0.001(3) 0.005(3) O17W 0.028(2) 0.043(3) 0.033(2) 0.008(2) 0.0016(18) -0.009(2) O18W 0.042(3) 0.045(3) 0.045(3) 0.002(2) -0.001(2) 0.004(2) O19W 0.029(2) 0.034(2) 0.040(3) 0.002(2) -0.0009(19) 0.0110(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 1.937(4) . ? Co1 N39 1.949(4) . ? Co1 N69 1.949(4) . ? Co1 N61 1.950(4) . ? Co1 N31 1.951(4) . ? Co1 N9 1.957(4) . ? Co2 N24 1.942(5) . ? Co2 N54 1.945(5) . ? Co2 N84 1.949(5) . ? Co2 N46 1.954(4) . ? Co2 N76 1.960(4) . ? Co2 N16 1.961(4) . ? N1 C2 1.337(7) . ? N1 C6 1.349(7) . ? C2 C3 1.376(8) . ? C3 C4 1.366(9) . ? C4 C5 1.398(8) . ? C5 C6 1.353(8) . ? C6 C7 1.498(7) . ? C7 O8 1.258(6) . ? C7 N9 1.319(7) . ? N9 C10 1.428(7) . ? C10 C11 1.388(7) . ? C10 C12 1.390(7) . ? C11 C15 1.392(7) . ? C12 C13 1.391(7) . ? C13 C14 1.385(7) . ? C14 C15 1.387(7) . ? C15 N16 1.434(7) . ? N16 C18 1.317(7) . ? O17 C18 1.253(7) . ? C18 C19 1.493(8) . ? C19 N24 1.354(7) . ? C19 C20 1.377(8) . ? C20 C21 1.380(9) . ? C21 C22 1.368(9) . ? C22 C23 1.386(8) . ? C23 N24 1.339(7) . ? N31 C32 1.328(7) . ? N31 C36 1.351(7) . ? C32 C33 1.370(8) . ? C33 C34 1.393(9) . ? C34 C35 1.376(9) . ? C35 C36 1.378(8) . ? C36 C37 1.484(8) . ? C37 O38 1.251(6) . ? C37 N39 1.326(7) . ? N39 C40 1.435(7) . ? C40 C42 1.380(8) . ? C40 C41 1.384(8) . ? C41 C45 1.395(7) . ? C42 C43 1.388(8) . ? C43 C44 1.388(8) . ? C44 C45 1.384(8) . ? C45 N46 1.422(7) . ? N46 C48 1.322(7) . ? O47 C48 1.258(6) . ? C48 C49 1.490(8) . ? C49 N54 1.355(7) . ? C49 C50 1.369(8) . ? C50 C51 1.400(9) . ? C51 C52 1.372(9) . ? C52 C53 1.386(8) . ? C53 N54 1.340(7) . ? N61 C62 1.328(7) . ? N61 C66 1.348(7) . ? C62 C63 1.382(9) . ? C63 C64 1.372(10) . ? C64 C65 1.362(9) . ? C65 C66 1.381(8) . ? C66 C67 1.482(8) . ? C67 O68 1.254(6) . ? C67 N69 1.326(7) . ? N69 C70 1.430(7) . ? C70 C72 1.385(7) . ? C70 C71 1.386(7) . ? C71 C75 1.381(7) . ? C72 C73 1.394(8) . ? C73 C74 1.383(8) . ? C74 C75 1.392(7) . ? C75 N76 1.439(7) . ? N76 C78 1.313(7) . ? O77 C78 1.258(7) . ? C78 C79 1.497(8) . ? C79 N84 1.342(8) . ? C79 C80 1.379(9) . ? C80 C81 1.378(10) . ? C81 C82 1.389(11) . ? C82 C83 1.373(9) . ? C83 N84 1.344(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N39 175.71(19) . . ? N1 Co1 N69 88.71(18) . . ? N39 Co1 N69 95.39(18) . . ? N1 Co1 N61 94.11(19) . . ? N39 Co1 N61 87.67(18) . . ? N69 Co1 N61 82.68(18) . . ? N1 Co1 N31 93.09(18) . . ? N39 Co1 N31 82.89(18) . . ? N69 Co1 N31 176.38(18) . . ? N61 Co1 N31 94.05(18) . . ? N1 Co1 N9 82.68(18) . . ? N39 Co1 N9 95.62(18) . . ? N69 Co1 N9 96.06(18) . . ? N61 Co1 N9 176.59(18) . . ? N31 Co1 N9 87.30(18) . . ? N24 Co2 N54 93.26(19) . . ? N24 Co2 N84 93.99(19) . . ? N54 Co2 N84 93.9(2) . . ? N24 Co2 N46 175.24(19) . . ? N54 Co2 N46 82.46(19) . . ? N84 Co2 N46 88.38(18) . . ? N24 Co2 N76 87.67(19) . . ? N54 Co2 N76 176.02(19) . . ? N84 Co2 N76 82.21(19) . . ? N46 Co2 N76 96.74(18) . . ? N24 Co2 N16 82.51(18) . . ? N54 Co2 N16 89.29(18) . . ? N84 Co2 N16 175.43(18) . . ? N46 Co2 N16 95.33(18) . . ? N76 Co2 N16 94.67(18) . . ? C2 N1 C6 118.5(5) . . ? C2 N1 Co1 127.3(4) . . ? C6 N1 Co1 114.2(3) . . ? N1 C2 C3 121.7(5) . . ? C4 C3 C2 120.2(5) . . ? C3 C4 C5 117.7(5) . . ? C6 C5 C4 119.7(5) . . ? N1 C6 C5 122.2(5) . . ? N1 C6 C7 114.4(5) . . ? C5 C6 C7 123.4(5) . . ? O8 C7 N9 127.5(5) . . ? O8 C7 C6 119.4(5) . . ? N9 C7 C6 113.1(5) . . ? C7 N9 C10 117.3(4) . . ? C7 N9 Co1 115.6(3) . . ? C10 N9 Co1 126.8(3) . . ? C11 C10 C12 119.8(5) . . ? C11 C10 N9 118.0(5) . . ? C12 C10 N9 122.2(5) . . ? C10 C11 C15 120.5(5) . . ? C10 C12 C13 119.2(5) . . ? C14 C13 C12 121.1(5) . . ? C13 C14 C15 119.6(5) . . ? C14 C15 C11 119.6(5) . . ? C14 C15 N16 121.8(5) . . ? C11 C15 N16 118.5(5) . . ? C18 N16 C15 117.6(4) . . ? C18 N16 Co2 115.7(4) . . ? C15 N16 Co2 125.7(3) . . ? O17 C18 N16 127.8(5) . . ? O17 C18 C19 119.5(5) . . ? N16 C18 C19 112.7(5) . . ? N24 C19 C20 122.1(5) . . ? N24 C19 C18 115.0(5) . . ? C20 C19 C18 122.8(5) . . ? C19 C20 C21 119.3(6) . . ? C22 C21 C20 118.5(6) . . ? C21 C22 C23 120.2(6) . . ? N24 C23 C22 121.4(6) . . ? C23 N24 C19 118.5(5) . . ? C23 N24 Co2 128.0(4) . . ? C19 N24 Co2 113.6(4) . . ? C32 N31 C36 119.4(5) . . ? C32 N31 Co1 127.4(4) . . ? C36 N31 Co1 113.1(4) . . ? N31 C32 C33 122.1(5) . . ? C32 C33 C34 119.5(5) . . ? C35 C34 C33 117.8(6) . . ? C34 C35 C36 120.3(6) . . ? N31 C36 C35 120.8(5) . . ? N31 C36 C37 115.4(5) . . ? C35 C36 C37 123.8(5) . . ? O38 C37 N39 126.9(5) . . ? O38 C37 C36 120.1(5) . . ? N39 C37 C36 113.0(5) . . ? C37 N39 C40 117.2(4) . . ? C37 N39 Co1 115.6(4) . . ? C40 N39 Co1 126.7(3) . . ? C42 C40 C41 119.9(5) . . ? C42 C40 N39 122.4(5) . . ? C41 C40 N39 117.7(5) . . ? C40 C41 C45 120.9(5) . . ? C40 C42 C43 119.4(5) . . ? C44 C43 C42 120.7(5) . . ? C45 C44 C43 120.0(5) . . ? C44 C45 C41 118.9(5) . . ? C44 C45 N46 122.6(5) . . ? C41 C45 N46 118.5(5) . . ? C48 N46 C45 116.9(4) . . ? C48 N46 Co2 115.6(4) . . ? C45 N46 Co2 126.9(3) . . ? O47 C48 N46 126.5(5) . . ? O47 C48 C49 120.1(5) . . ? N46 C48 C49 113.3(5) . . ? N54 C49 C50 122.5(5) . . ? N54 C49 C48 114.2(5) . . ? C50 C49 C48 123.3(5) . . ? C49 C50 C51 119.0(6) . . ? C52 C51 C50 118.6(6) . . ? C51 C52 C53 119.5(6) . . ? N54 C53 C52 122.2(6) . . ? C53 N54 C49 118.2(5) . . ? C53 N54 Co2 127.7(4) . . ? C49 N54 Co2 114.1(4) . . ? C62 N61 C66 118.7(5) . . ? C62 N61 Co1 127.8(4) . . ? C66 N61 Co1 113.5(4) . . ? N61 C62 C63 121.8(6) . . ? C64 C63 C62 119.3(6) . . ? C65 C64 C63 119.2(6) . . ? C64 C65 C66 119.2(6) . . ? N61 C66 C65 121.8(5) . . ? N61 C66 C67 115.1(5) . . ? C65 C66 C67 123.1(5) . . ? O68 C67 N69 126.8(5) . . ? O68 C67 C66 120.0(5) . . ? N69 C67 C66 113.1(5) . . ? C67 N69 C70 117.4(4) . . ? C67 N69 Co1 115.6(4) . . ? C70 N69 Co1 126.8(3) . . ? C72 C70 C71 119.3(5) . . ? C72 C70 N69 122.3(5) . . ? C71 C70 N69 118.4(5) . . ? C75 C71 C70 121.0(5) . . ? C70 C72 C73 119.7(5) . . ? C74 C73 C72 120.9(5) . . ? C73 C74 C75 119.2(5) . . ? C71 C75 C74 119.8(5) . . ? C71 C75 N76 117.8(5) . . ? C74 C75 N76 122.3(5) . . ? C78 N76 C75 116.9(5) . . ? C78 N76 Co2 115.6(4) . . ? C75 N76 Co2 127.5(3) . . ? O77 C78 N76 127.1(5) . . ? O77 C78 C79 119.6(5) . . ? N76 C78 C79 113.2(5) . . ? N84 C79 C80 123.1(6) . . ? N84 C79 C78 114.4(5) . . ? C80 C79 C78 122.3(6) . . ? C81 C80 C79 118.3(7) . . ? C80 C81 C82 118.8(7) . . ? C83 C82 C81 119.6(7) . . ? N84 C83 C82 121.8(6) . . ? C79 N84 C83 118.3(5) . . ? C79 N84 Co2 114.3(4) . . ? C83 N84 Co2 127.4(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.316 _refine_diff_density_min -0.753 _refine_diff_density_rms 0.095 # Attachment 'B905330A_Final.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 723672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H36 Cu2 F12 Mn N10 O10' _chemical_formula_weight 1346.91 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.248(2) _cell_length_b 12.108(2) _cell_length_c 12.458(2) _cell_angle_alpha 72.468(2) _cell_angle_beta 71.400(2) _cell_angle_gamma 63.689(2) _cell_volume 1415.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3450 _cell_measurement_theta_min 2.212 _cell_measurement_theta_max 22.438 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 677 _exptl_absorpt_coefficient_mu 1.068 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.647 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _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 ? _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 16405 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6279 _reflns_number_gt 4622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1212P)^2^+1.5429P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6279 _refine_ls_number_parameters 368 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.2107 _refine_ls_wR_factor_gt 0.1935 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.064 _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 Cu1 Cu 0.11250(5) 0.16192(6) 0.63443(5) 0.0401(2) Uani 1 1 d . . . Mn2 Mn 0.5000 0.0000 0.0000 0.0317(2) Uani 1 2 d S . . N1C N -0.2912(4) -0.1800(4) 0.4073(3) 0.0396(8) Uiso 1 1 d . . . C2C C -0.3498(6) -0.1994(5) 0.3413(5) 0.0568(13) Uiso 1 1 d . . . H2C H -0.3040 -0.2086 0.2659 0.068 Uiso 1 1 calc R . . C3C C -0.4743(6) -0.2062(6) 0.3798(5) 0.0648(17) Uani 1 1 d . . . H3C H -0.5116 -0.2214 0.3316 0.078 Uiso 1 1 calc R . . C4C C -0.5433(6) -0.1911(5) 0.4883(5) 0.0561(13) Uiso 1 1 d . . . H4C H -0.6285 -0.1958 0.5159 0.067 Uiso 1 1 calc R . . C5C C -0.4856(5) -0.1683(5) 0.5579(5) 0.0490(12) Uiso 1 1 d . . . H5C H -0.5320 -0.1555 0.6325 0.059 Uiso 1 1 calc R . . C6C C -0.3584(4) -0.1650(4) 0.5148(4) 0.0355(9) Uiso 1 1 d . . . C7C C -0.2875(4) -0.1444(4) 0.5859(4) 0.0357(9) Uani 1 1 d . . . O8C O -0.3429(4) -0.1369(4) 0.6885(3) 0.0520(9) Uani 1 1 d . . . N9C N -0.1678(4) -0.1414(3) 0.5288(3) 0.0340(8) Uiso 1 1 d . . . N1D N -0.0437(4) 0.3356(4) 0.6738(4) 0.0423(9) Uani 1 1 d . . . C2D C -0.0375(6) 0.4431(5) 0.6762(5) 0.0581(14) Uani 1 1 d . . . H2D H 0.0468 0.4491 0.6549 0.070 Uiso 1 1 calc R . . C3D C -0.1507(7) 0.5442(5) 0.7087(6) 0.0683(17) Uani 1 1 d . . . H3D H -0.1428 0.6173 0.7092 0.082 Uiso 1 1 calc R . . C4D C -0.2747(7) 0.5368(6) 0.7402(6) 0.0693(17) Uani 1 1 d . . . H4D H -0.3526 0.6045 0.7631 0.083 Uiso 1 1 calc R . . C5D C -0.2831(5) 0.4271(5) 0.7377(5) 0.0550(14) Uani 1 1 d . . . H5D H -0.3671 0.4205 0.7576 0.066 Uiso 1 1 calc R . . C6D C -0.1653(5) 0.3273(4) 0.7054(4) 0.0382(10) Uani 1 1 d . . . C7D C -0.1681(5) 0.2042(4) 0.7069(4) 0.0379(10) Uani 1 1 d . . . O8D O -0.2798(3) 0.1937(3) 0.7370(3) 0.0527(9) Uani 1 1 d . . . N9D N -0.0466(3) 0.1180(3) 0.6762(3) 0.0323(8) Uani 1 1 d . . . C11E C 0.0853(5) -0.1031(5) 0.6881(4) 0.0394(10) Uani 1 1 d . . . H11E H 0.1431 -0.0949 0.7218 0.047 Uiso 1 1 calc R . . C12E C 0.1146(5) -0.2195(5) 0.6637(4) 0.0454(11) Uani 1 1 d . . . H12E H 0.1909 -0.2888 0.6824 0.055 Uiso 1 1 calc R . . C13E C 0.0305(5) -0.2311(5) 0.6119(4) 0.0431(11) Uani 1 1 d . . . H13E H 0.0514 -0.3076 0.5936 0.052 Uiso 1 1 calc R . . C14E C -0.0860(4) -0.1286(4) 0.5869(3) 0.0328(9) Uani 1 1 d . . . C15E C -0.1158(4) -0.0144(4) 0.6127(3) 0.0341(9) Uani 1 1 d . . . H15E H -0.1942 0.0537 0.5967 0.041 Uiso 1 1 calc R . . C16E C -0.0297(4) -0.0002(4) 0.6622(3) 0.0301(8) Uani 1 1 d . . . C4I C 0.6476(5) 0.2566(5) 0.0601(5) 0.0503(13) Uani 1 1 d D . . C5I C 0.5550(5) 0.2165(4) 0.0259(4) 0.0370(10) Uani 1 1 d . . . O6I O 0.5936(3) 0.1025(3) 0.0360(3) 0.0393(7) Uani 1 1 d . . . C4K C 0.2331(9) 0.4036(6) -0.0864(9) 0.105(3) Uani 1 1 d D . . C5K C 0.3512(5) 0.2888(4) -0.0479(5) 0.0448(11) Uani 1 1 d . . . O6K O 0.3577(3) 0.1880(3) -0.0597(3) 0.0450(8) Uani 1 1 d . . . C7K C 0.4400(5) 0.3124(5) -0.0105(5) 0.0460(12) Uani 1 1 d . . . O1G O 0.3645(4) 0.0038(4) 0.1636(3) 0.0511(10) Uani 1 1 d . . . N1O N 0.1278(5) 0.1044(5) 0.8173(4) 0.0516(11) Uani 1 1 d . . . C2O C 0.1125(5) 0.1019(5) 0.9112(5) 0.0466(12) Uani 1 1 d . . . C3O C 0.0890(6) 0.0998(7) 1.0335(5) 0.0629(16) Uani 1 1 d . . . H3O1 H -0.0027 0.1549 1.0599 0.094 Uiso 1 1 calc R . . H3O2 H 0.1510 0.1272 1.0455 0.094 Uiso 1 1 calc R . . H3O3 H 0.1029 0.0160 1.0757 0.094 Uiso 1 1 calc R . . F1 F 0.7714(4) 0.2158(5) -0.0021(4) 0.0902(13) Uani 1 1 d D . . F2 F 0.6588(5) 0.2085(5) 0.1660(3) 0.0984(15) Uani 1 1 d D . . F3 F 0.6112(5) 0.3773(4) 0.0459(6) 0.123(2) Uani 1 1 d D . . F4 F 0.1946(6) 0.4998(5) -0.0471(7) 0.161(3) Uani 1 1 d D . . F5 F 0.1386(7) 0.3816(5) -0.0919(11) 0.212(5) Uani 1 1 d D . . F6 F 0.2686(11) 0.4479(9) -0.1967(8) 0.281(7) Uani 1 1 d D . . H7K H 0.417(5) 0.400(5) -0.007(4) 0.046(14) Uiso 1 1 d . . . H1G H 0.338(6) -0.045(5) 0.184(5) 0.042(16) Uiso 1 1 d . . . H2G H 0.347(6) 0.051(6) 0.202(6) 0.059(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0363(3) 0.0589(4) 0.0386(3) -0.0241(3) 0.0053(2) -0.0296(3) Mn2 0.0323(5) 0.0342(5) 0.0317(5) -0.0112(4) -0.0005(4) -0.0166(4) C3C 0.063(4) 0.095(5) 0.059(3) 0.000(3) -0.024(3) -0.052(3) C7C 0.034(2) 0.041(2) 0.037(2) -0.0148(19) 0.0013(18) -0.0201(19) O8C 0.052(2) 0.080(3) 0.0397(18) -0.0281(18) 0.0104(16) -0.042(2) N1D 0.038(2) 0.042(2) 0.050(2) -0.0149(18) -0.0018(17) -0.0203(18) C2D 0.058(3) 0.051(3) 0.074(4) -0.015(3) -0.004(3) -0.033(3) C3D 0.075(4) 0.044(3) 0.084(4) -0.018(3) 0.001(3) -0.029(3) C4D 0.068(4) 0.051(3) 0.078(4) -0.026(3) 0.000(3) -0.016(3) C5D 0.043(3) 0.049(3) 0.064(3) -0.016(3) 0.006(2) -0.018(2) C6D 0.038(2) 0.042(2) 0.036(2) -0.0111(19) -0.0022(19) -0.018(2) C7D 0.038(2) 0.047(3) 0.034(2) -0.0102(19) -0.0024(19) -0.024(2) O8D 0.0329(17) 0.054(2) 0.075(3) -0.0263(18) 0.0063(16) -0.0236(16) N9D 0.0301(18) 0.042(2) 0.0308(18) -0.0141(15) -0.0009(14) -0.0184(16) C11E 0.036(2) 0.054(3) 0.036(2) -0.011(2) -0.0088(19) -0.022(2) C12E 0.039(3) 0.043(3) 0.051(3) -0.005(2) -0.014(2) -0.012(2) C13E 0.045(3) 0.040(2) 0.048(3) -0.008(2) -0.007(2) -0.021(2) C14E 0.032(2) 0.048(2) 0.0256(19) -0.0080(18) -0.0009(16) -0.0245(19) C15E 0.031(2) 0.045(2) 0.028(2) -0.0108(18) 0.0019(17) -0.0193(19) C16E 0.028(2) 0.040(2) 0.0251(19) -0.0102(17) 0.0015(16) -0.0179(18) C4I 0.048(3) 0.048(3) 0.068(4) -0.013(3) -0.023(3) -0.021(2) C5I 0.037(2) 0.040(2) 0.040(2) -0.0125(19) -0.0040(19) -0.020(2) O6I 0.0368(16) 0.0372(17) 0.0508(19) -0.0134(14) -0.0117(14) -0.0156(14) C4K 0.114(7) 0.046(4) 0.183(10) -0.026(5) -0.111(7) 0.003(4) C5K 0.040(3) 0.038(2) 0.058(3) -0.013(2) -0.016(2) -0.009(2) O6K 0.0397(17) 0.0452(19) 0.056(2) -0.0138(16) -0.0173(15) -0.0142(15) C7K 0.044(3) 0.035(2) 0.064(3) -0.016(2) -0.019(2) -0.011(2) O1G 0.065(2) 0.064(3) 0.0365(19) -0.0207(18) 0.0140(17) -0.045(2) N1O 0.056(3) 0.073(3) 0.040(2) -0.009(2) -0.010(2) -0.037(2) C2O 0.038(2) 0.064(3) 0.046(3) -0.008(2) -0.010(2) -0.028(2) C3O 0.056(3) 0.105(5) 0.040(3) -0.019(3) -0.007(2) -0.042(3) F1 0.059(2) 0.132(4) 0.106(3) -0.041(3) -0.003(2) -0.058(2) F2 0.120(4) 0.160(4) 0.065(2) -0.008(3) -0.037(2) -0.094(3) F3 0.124(4) 0.055(2) 0.240(7) -0.030(3) -0.109(4) -0.030(2) F4 0.131(5) 0.083(3) 0.289(9) -0.098(4) -0.142(6) 0.046(3) F5 0.117(5) 0.078(4) 0.483(16) -0.052(6) -0.187(8) 0.007(3) F6 0.276(13) 0.192(9) 0.211(10) 0.038(7) -0.150(9) 0.069(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N9D 1.959(3) . ? Cu1 N9C 1.986(4) 2_556 ? Cu1 N1C 2.004(4) 2_556 ? Cu1 N1D 2.132(4) . ? Cu1 N1O 2.212(4) . ? Mn2 O1G 2.119(4) 2_655 ? Mn2 O1G 2.119(4) . ? Mn2 O6I 2.155(3) . ? Mn2 O6I 2.155(3) 2_655 ? Mn2 O6K 2.192(3) . ? Mn2 O6K 2.192(3) 2_655 ? N1C C2C 1.329(7) . ? N1C C6C 1.332(6) . ? N1C Cu1 2.004(4) 2_556 ? C2C C3C 1.360(8) . ? C3C C4C 1.347(8) . ? C4C C5C 1.383(8) . ? C5C C6C 1.373(7) . ? C6C C7C 1.498(6) . ? C7C O8C 1.241(5) . ? C7C N9C 1.318(5) . ? N9C C14E 1.419(5) . ? N9C Cu1 1.986(4) 2_556 ? N1D C6D 1.339(6) . ? N1D C2D 1.344(6) . ? C2D C3D 1.367(8) . ? C3D C4D 1.359(9) . ? C4D C5D 1.384(8) . ? C5D C6D 1.383(7) . ? C6D C7D 1.498(6) . ? C7D O8D 1.244(5) . ? C7D N9D 1.321(6) . ? N9D C16E 1.415(5) . ? C11E C16E 1.388(6) . ? C11E C12E 1.404(7) . ? C12E C13E 1.375(7) . ? C13E C14E 1.393(7) . ? C14E C15E 1.384(6) . ? C15E C16E 1.392(6) . ? C4I F2 1.294(6) . ? C4I F3 1.302(6) . ? C4I F1 1.309(6) . ? C4I C5I 1.536(6) . ? C5I O6I 1.228(5) . ? C5I C7K 1.397(7) . ? C4K F5 1.231(8) . ? C4K F4 1.243(8) . ? C4K F6 1.316(12) . ? C4K C5K 1.515(8) . ? C5K O6K 1.239(6) . ? C5K C7K 1.389(7) . ? N1O C2O 1.120(6) . ? C2O C3O 1.455(7) . ? 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 N9D Cu1 N9C 96.47(14) . 2_556 ? N9D Cu1 N1C 171.63(15) . 2_556 ? N9C Cu1 N1C 81.44(15) 2_556 2_556 ? N9D Cu1 N1D 80.26(15) . . ? N9C Cu1 N1D 117.07(15) 2_556 . ? N1C Cu1 N1D 107.94(15) 2_556 . ? N9D Cu1 N1O 89.82(15) . . ? N9C Cu1 N1O 154.55(17) 2_556 . ? N1C Cu1 N1O 88.77(16) 2_556 . ? N1D Cu1 N1O 88.26(17) . . ? O1G Mn2 O1G 180.0(3) 2_655 . ? O1G Mn2 O6I 87.28(14) 2_655 . ? O1G Mn2 O6I 92.72(14) . . ? O1G Mn2 O6I 92.72(14) 2_655 2_655 ? O1G Mn2 O6I 87.28(14) . 2_655 ? O6I Mn2 O6I 180.00(15) . 2_655 ? O1G Mn2 O6K 92.06(16) 2_655 . ? O1G Mn2 O6K 87.94(16) . . ? O6I Mn2 O6K 83.43(12) . . ? O6I Mn2 O6K 96.57(12) 2_655 . ? O1G Mn2 O6K 87.94(16) 2_655 2_655 ? O1G Mn2 O6K 92.06(16) . 2_655 ? O6I Mn2 O6K 96.57(12) . 2_655 ? O6I Mn2 O6K 83.43(12) 2_655 2_655 ? O6K Mn2 O6K 180.0(3) . 2_655 ? C2C N1C C6C 118.4(4) . . ? C2C N1C Cu1 128.5(4) . 2_556 ? C6C N1C Cu1 113.0(3) . 2_556 ? N1C C2C C3C 122.5(6) . . ? C4C C3C C2C 119.6(6) . . ? C3C C4C C5C 118.9(5) . . ? C6C C5C C4C 118.7(5) . . ? N1C C6C C5C 121.8(4) . . ? N1C C6C C7C 116.4(4) . . ? C5C C6C C7C 121.8(4) . . ? O8C C7C N9C 128.4(4) . . ? O8C C7C C6C 118.6(4) . . ? N9C C7C C6C 112.9(4) . . ? C7C N9C C14E 119.2(4) . . ? C7C N9C Cu1 116.2(3) . 2_556 ? C14E N9C Cu1 124.5(3) . 2_556 ? C6D N1D C2D 118.5(4) . . ? C6D N1D Cu1 110.3(3) . . ? C2D N1D Cu1 131.2(4) . . ? N1D C2D C3D 122.5(5) . . ? C4D C3D C2D 119.5(5) . . ? C3D C4D C5D 118.9(6) . . ? C6D C5D C4D 119.3(5) . . ? N1D C6D C5D 121.4(4) . . ? N1D C6D C7D 117.2(4) . . ? C5D C6D C7D 121.4(4) . . ? O8D C7D N9D 127.9(4) . . ? O8D C7D C6D 118.4(4) . . ? N9D C7D C6D 113.7(4) . . ? C7D N9D C16E 121.8(3) . . ? C7D N9D Cu1 118.6(3) . . ? C16E N9D Cu1 119.3(3) . . ? C16E C11E C12E 120.2(4) . . ? C13E C12E C11E 119.9(4) . . ? C12E C13E C14E 120.2(4) . . ? C15E C14E C13E 119.7(4) . . ? C15E C14E N9C 121.1(4) . . ? C13E C14E N9C 119.1(4) . . ? C14E C15E C16E 120.8(4) . . ? C11E C16E C15E 119.1(4) . . ? C11E C16E N9D 117.9(4) . . ? C15E C16E N9D 122.6(4) . . ? F2 C4I F3 107.8(5) . . ? F2 C4I F1 105.4(5) . . ? F3 C4I F1 105.5(5) . . ? F2 C4I C5I 112.0(4) . . ? F3 C4I C5I 114.9(4) . . ? F1 C4I C5I 110.6(4) . . ? O6I C5I C7K 129.4(4) . . ? O6I C5I C4I 113.9(4) . . ? C7K C5I C4I 116.7(4) . . ? C5I O6I Mn2 128.3(3) . . ? F5 C4K F4 113.2(8) . . ? F5 C4K F6 97.7(8) . . ? F4 C4K F6 99.4(8) . . ? F5 C4K C5K 114.7(6) . . ? F4 C4K C5K 118.7(6) . . ? F6 C4K C5K 109.7(8) . . ? O6K C5K C7K 129.5(4) . . ? O6K C5K C4K 115.0(5) . . ? C7K C5K C4K 115.4(5) . . ? C5K O6K Mn2 126.5(3) . . ? C5K C7K C5I 122.2(4) . . ? C2O N1O Cu1 163.9(5) . . ? N1O C2O C3O 178.5(5) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.610 _refine_diff_density_min -0.705 _refine_diff_density_rms 0.111 data_2 _database_code_depnum_ccdc_archive 'CCDC 723673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H73 N13 O26 Zn2' _chemical_formula_weight 1450.99 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 hexagonal _symmetry_space_group_name_H-M P63/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' '-x+y, -x, z' 'x-y, x, z+1/2' 'y, -x+y, z+1/2' '-x, -y, -z' 'x, y, -z-1/2' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, -x, -z-1/2' '-y, x-y, -z-1/2' _cell_length_a 13.645(2) _cell_length_b 13.645(2) _cell_length_c 22.394(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3610.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1813 _cell_measurement_theta_min 2.480 _cell_measurement_theta_max 19.210 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.783 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 13275 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 19.52 _reflns_number_total 1082 _reflns_number_gt 863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.2000P)^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 1082 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1894 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.6667 0.3333 0.09823(5) 0.0655(8) Uani 1 3 d S . . N1 N 0.5310(6) 0.2055(5) 0.0404(2) 0.0758(18) Uani 1 1 d . . . C2 C 0.5370(7) 0.1601(8) -0.0118(3) 0.095(2) Uani 1 1 d . . . H2 H 0.6077 0.1839 -0.0285 0.114 Uiso 1 1 calc R . . C3 C 0.4430(13) 0.0804(10) -0.0410(4) 0.133(4) Uani 1 1 d . . . H3 H 0.4521 0.0505 -0.0765 0.160 Uiso 1 1 calc R . . C4 C 0.3391(10) 0.0441(9) -0.0207(5) 0.127(3) Uani 1 1 d . . . H4 H 0.2757 -0.0064 -0.0425 0.152 Uiso 1 1 calc R . . C5 C 0.3289(8) 0.0853(7) 0.0353(4) 0.109(3) Uani 1 1 d . . . H5 H 0.2585 0.0596 0.0529 0.131 Uiso 1 1 calc R . . C6 C 0.4286(8) 0.1664(6) 0.0637(3) 0.076(2) Uani 1 1 d . . . C7 C 0.4220(7) 0.2199(6) 0.1215(3) 0.0647(19) Uani 1 1 d . . . O8 O 0.3258(5) 0.1823(5) 0.1437(2) 0.1017(19) Uani 1 1 d . . . N9 N 0.7004(5) 0.2162(4) 0.1414(2) 0.0630(16) Uani 1 1 d . . . C10 C 0.6462(6) 0.1610(6) 0.1968(3) 0.0587(18) Uani 1 1 d . . . C11 C 0.7004(8) 0.2079(8) 0.2500 0.060(3) Uani 1 2 d S . . H11 H 0.7729 0.2707 0.2500 0.072 Uiso 1 2 calc SR . . C12 C 0.5410(6) 0.0685(6) 0.1960(3) 0.071(2) Uani 1 1 d . . . H12 H 0.5035 0.0381 0.1602 0.085 Uiso 1 1 calc R . . C13 C 0.4917(9) 0.0211(8) 0.2500 0.077(3) Uani 1 2 d S . . H13 H 0.4222 -0.0456 0.2500 0.093 Uiso 1 2 calc SR . . 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 Zn1 0.0849(10) 0.0849(10) 0.0267(11) 0.000 0.000 0.0425(5) N1 0.106(5) 0.092(4) 0.034(4) -0.011(3) -0.015(4) 0.053(4) C2 0.122(7) 0.121(7) 0.040(5) -0.013(5) -0.008(5) 0.059(6) C3 0.203(12) 0.166(10) 0.067(7) -0.064(7) -0.037(8) 0.119(10) C4 0.129(9) 0.134(8) 0.101(8) -0.059(7) -0.022(7) 0.054(7) C5 0.109(7) 0.092(6) 0.099(7) -0.020(6) -0.019(6) 0.030(6) C6 0.097(7) 0.078(5) 0.049(5) 0.010(4) -0.011(5) 0.040(5) C7 0.059(5) 0.075(5) 0.041(5) 0.007(4) 0.008(4) 0.019(5) O8 0.083(4) 0.124(4) 0.064(4) -0.013(3) -0.007(3) 0.026(4) N9 0.078(4) 0.077(4) 0.037(3) -0.002(3) 0.000(3) 0.041(3) C10 0.076(5) 0.078(5) 0.030(4) 0.003(4) 0.003(4) 0.044(4) C11 0.081(6) 0.080(6) 0.034(6) 0.000 0.000 0.050(6) C12 0.086(6) 0.073(5) 0.042(4) -0.012(4) 0.000(4) 0.032(5) C13 0.099(8) 0.058(6) 0.051(7) 0.000 0.000 0.021(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 Zn1 N9 2.106(5) . ? Zn1 N9 2.106(5) 3_655 ? Zn1 N9 2.106(5) 4_665 ? Zn1 N1 2.218(6) 3_655 ? Zn1 N1 2.218(6) . ? Zn1 N1 2.218(6) 4_665 ? N1 C2 1.343(9) . ? N1 C6 1.328(9) . ? C2 C3 1.365(13) . ? C3 C4 1.326(13) . ? C4 C5 1.409(12) . ? C5 C6 1.405(11) . ? C6 C7 1.510(10) . ? C7 O8 1.250(7) . ? C7 N9 1.276(8) 4_665 ? N9 C7 1.276(8) 3_655 ? N9 C10 1.448(8) . ? C10 C12 1.357(9) . ? C10 C11 1.380(8) . ? C11 C10 1.380(8) 8_556 ? C12 C13 1.378(8) . ? C13 C12 1.378(8) 8_556 ? 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 N9 Zn1 N9 100.63(18) . 3_655 ? N9 Zn1 N9 100.63(18) . 4_665 ? N9 Zn1 N9 100.63(18) 3_655 4_665 ? N9 Zn1 N1 75.9(2) . 3_655 ? N9 Zn1 N1 94.8(2) 3_655 3_655 ? N9 Zn1 N1 164.5(2) 4_665 3_655 ? N9 Zn1 N1 94.8(2) . . ? N9 Zn1 N1 164.5(2) 3_655 . ? N9 Zn1 N1 75.9(2) 4_665 . ? N1 Zn1 N1 89.3(2) 3_655 . ? N9 Zn1 N1 164.5(2) . 4_665 ? N9 Zn1 N1 75.9(2) 3_655 4_665 ? N9 Zn1 N1 94.8(2) 4_665 4_665 ? N1 Zn1 N1 89.3(2) 3_655 4_665 ? N1 Zn1 N1 89.3(2) . 4_665 ? C2 N1 C6 116.8(6) . . ? C2 N1 Zn1 130.6(6) . . ? C6 N1 Zn1 112.5(5) . . ? N1 C2 C3 122.4(8) . . ? C4 C3 C2 122.4(9) . . ? C3 C4 C5 117.1(9) . . ? C6 C5 C4 117.9(9) . . ? N1 C6 C5 123.2(7) . . ? N1 C6 C7 116.6(7) . . ? C5 C6 C7 120.1(9) . . ? O8 C7 N9 127.7(6) . 4_665 ? O8 C7 C6 116.5(7) . . ? N9 C7 C6 115.8(7) 4_665 . ? C7 N9 C10 118.2(5) 3_655 . ? C7 N9 Zn1 118.7(5) 3_655 . ? C10 N9 Zn1 122.6(4) . . ? C12 C10 C11 121.0(6) . . ? C12 C10 N9 120.0(6) . . ? C11 C10 N9 118.9(6) . . ? C10 C11 C10 119.5(9) . 8_556 ? C10 C12 C13 117.8(7) . . ? C12 C13 C12 122.7(9) 8_556 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 19.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.416 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.057 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 -0.013 -0.010 -0.001 1576 255 ' ' _platon_squeeze_details ; ; data_3 _database_code_depnum_ccdc_archive 'CCDC 723674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H69 Cl N12 Ni2 O25' _chemical_formula_weight 1439.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P63/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' '-x+y, -x, z' 'x-y, x, z+1/2' 'y, -x+y, z+1/2' '-x, -y, -z' 'x, y, -z-1/2' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, -x, -z-1/2' '-y, x-y, -z-1/2' _cell_length_a 13.6913(19) _cell_length_b 13.6913(19) _cell_length_c 22.130(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3592.5(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11343 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 24.19 _exptl_crystal_description prismatic _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 0.642 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 44296 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 29.46 _reflns_number_total 3306 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1089P)^2^+0.2445P] 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 3306 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 Ni1 Ni 0.6667 0.3333 0.093340(16) 0.04061(18) Uani 1 3 d S . . N1 N 0.53540(15) 0.20685(14) 0.04108(7) 0.0501(4) Uani 1 1 d . . . C2 C 0.5449(2) 0.1611(2) -0.01083(10) 0.0663(6) Uani 1 1 d . . . H2 H 0.6162 0.1833 -0.0262 0.080 Uiso 1 1 calc R . . C3 C 0.4496(3) 0.0809(3) -0.04203(12) 0.0831(8) Uani 1 1 d . . . H3 H 0.4575 0.0500 -0.0779 0.100 Uiso 1 1 calc R . . C4 C 0.3463(3) 0.0486(3) -0.01985(14) 0.0885(9) Uani 1 1 d . . . H4 H 0.2824 -0.0033 -0.0408 0.106 Uiso 1 1 calc R . . C5 C 0.3358(2) 0.0926(2) 0.03393(13) 0.0712(7) Uani 1 1 d . . . H5 H 0.2650 0.0695 0.0503 0.085 Uiso 1 1 calc R . . C6 C 0.43287(17) 0.17227(16) 0.06334(9) 0.0501(5) Uani 1 1 d . . . C7 C 0.42653(16) 0.22774(17) 0.12089(9) 0.0499(4) Uani 1 1 d . . . O8 O 0.33027(12) 0.19335(18) 0.14369(8) 0.0758(5) Uani 1 1 d . . . N9 N 0.69204(13) 0.21540(12) 0.13996(6) 0.0429(4) Uani 1 1 d . . . C10 C 0.63781(16) 0.16126(15) 0.19543(7) 0.0415(4) Uani 1 1 d . . . C11 C 0.6926(2) 0.2055(2) 0.2500 0.0415(5) Uani 1 2 d S . . H11 H 0.7666 0.2652 0.2500 0.050 Uiso 1 2 calc SR . . C12 C 0.52968(18) 0.07022(16) 0.19534(8) 0.0513(5) Uani 1 1 d . . . H12 H 0.4930 0.0398 0.1590 0.062 Uiso 1 1 calc R . . C13 C 0.4755(3) 0.0239(2) 0.2500 0.0560(7) Uani 1 2 d S . . H13 H 0.4029 -0.0381 0.2500 0.067 Uiso 1 2 calc SR . . 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 Ni1 0.0469(2) 0.0469(2) 0.0281(2) 0.000 0.000 0.02343(11) N1 0.0616(10) 0.0545(9) 0.0348(7) -0.0066(6) -0.0073(7) 0.0296(8) C2 0.0797(16) 0.0752(15) 0.0478(11) -0.0204(10) -0.0128(11) 0.0416(13) C3 0.098(2) 0.0845(18) 0.0666(16) -0.0401(14) -0.0264(14) 0.0459(16) C4 0.086(2) 0.0736(17) 0.0868(18) -0.0388(15) -0.0313(16) 0.0260(15) C5 0.0603(13) 0.0653(14) 0.0766(16) -0.0185(12) -0.0163(12) 0.0229(11) C6 0.0559(11) 0.0488(10) 0.0418(10) -0.0028(8) -0.0102(8) 0.0233(9) C7 0.0488(10) 0.0587(11) 0.0399(9) 0.0008(8) -0.0040(8) 0.0251(9) O8 0.0444(8) 0.1019(13) 0.0648(11) -0.0121(9) 0.0001(7) 0.0244(8) N9 0.0530(8) 0.0462(8) 0.0300(7) -0.0019(6) 0.0015(6) 0.0252(7) C10 0.0551(10) 0.0422(9) 0.0319(8) -0.0010(6) 0.0014(7) 0.0279(8) C11 0.0490(13) 0.0421(12) 0.0360(11) 0.000 0.000 0.0247(11) C12 0.0663(12) 0.0453(10) 0.0373(9) -0.0058(7) -0.0056(8) 0.0242(9) C13 0.0589(16) 0.0426(14) 0.0485(15) 0.000 0.000 0.0118(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N9 2.0864(15) . ? Ni1 N9 2.0864(15) 3_655 ? Ni1 N9 2.0864(15) 4_665 ? Ni1 N1 2.1105(16) 3_655 ? Ni1 N1 2.1105(16) . ? Ni1 N1 2.1105(16) 4_665 ? N1 C6 1.331(3) . ? N1 C2 1.345(3) . ? C2 C3 1.398(3) . ? C3 C4 1.345(4) . ? C4 C5 1.374(4) . ? C5 C6 1.389(3) . ? C6 C7 1.507(3) . ? C7 O8 1.262(2) . ? C7 N9 1.298(2) 4_665 ? N9 C7 1.298(2) 3_655 ? N9 C10 1.434(2) . ? C10 C12 1.378(3) . ? C10 C11 1.391(2) . ? C11 C10 1.391(2) 8_556 ? C12 C13 1.395(2) . ? C13 C12 1.395(2) 8_556 ? 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 N9 Ni1 N9 97.66(5) . 3_655 ? N9 Ni1 N9 97.66(5) . 4_665 ? N9 Ni1 N9 97.66(5) 3_655 4_665 ? N9 Ni1 N1 77.89(6) . 3_655 ? N9 Ni1 N1 92.23(6) 3_655 3_655 ? N9 Ni1 N1 169.64(6) 4_665 3_655 ? N9 Ni1 N1 92.23(6) . . ? N9 Ni1 N1 169.64(6) 3_655 . ? N9 Ni1 N1 77.89(6) 4_665 . ? N1 Ni1 N1 92.84(6) 3_655 . ? N9 Ni1 N1 169.64(6) . 4_665 ? N9 Ni1 N1 77.89(6) 3_655 4_665 ? N9 Ni1 N1 92.23(6) 4_665 4_665 ? N1 Ni1 N1 92.84(6) 3_655 4_665 ? N1 Ni1 N1 92.84(6) . 4_665 ? C6 N1 C2 118.74(18) . . ? C6 N1 Ni1 113.75(12) . . ? C2 N1 Ni1 127.50(16) . . ? N1 C2 C3 121.2(2) . . ? C4 C3 C2 119.5(2) . . ? C3 C4 C5 119.7(2) . . ? C4 C5 C6 118.8(3) . . ? N1 C6 C5 122.0(2) . . ? N1 C6 C7 116.72(16) . . ? C5 C6 C7 121.2(2) . . ? O8 C7 N9 128.30(19) . 4_665 ? O8 C7 C6 117.53(17) . . ? N9 C7 C6 114.15(17) 4_665 . ? C7 N9 C10 116.89(16) 3_655 . ? C7 N9 Ni1 117.23(12) 3_655 . ? C10 N9 Ni1 125.43(11) . . ? C12 C10 C11 119.80(17) . . ? C12 C10 N9 120.69(15) . . ? C11 C10 N9 119.39(17) . . ? C10 C11 C10 120.5(2) . 8_556 ? C10 C12 C13 119.78(18) . . ? C12 C13 C12 120.3(3) 8_556 . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 29.46 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.489 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.082 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 -0.013 -0.010 -0.001 1600 62 ' ' _platon_squeeze_details ; ;