# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Dong, Yu-Bin' _publ_contact_author_name 'Dong, Yu-Bin' _publ_contact_author_email yubindong@sdnu.edu.cn _publ_section_title ; NbO lattice MOFs based on octahedral M(II) and ditopic pyridyl substituted diketonate ligands: structure, encapsulation and guest-driven luminescent property ; data_101206em _database_code_depnum_ccdc_archive 'CCDC 833167' #TrackingRef '101206em.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31.67 H28.67 Cl2 N2 O4.67 Zn' _chemical_formula_weight 648.17 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 21.746(2) _cell_length_b 21.746(2) _cell_length_c 7.7165(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3160.1(8) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3902 _cell_measurement_theta_min 2.850 _cell_measurement_theta_max 22.483 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1002 _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7563 _exptl_absorpt_correction_T_max 0.8086 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16720 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.58 _reflns_number_total 3984 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1601P)^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 3984 _refine_ls_number_parameters 246 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2219 _refine_ls_wR_factor_gt 0.2117 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.009 _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 C1 C 0.67812(9) 0.03689(10) 0.6710(2) 0.1235(8) Uani 1 1 d U . . H1A H 0.6548 0.0369 0.5623 0.185 Uiso 1 1 calc R . . H1B H 0.6802 -0.0070 0.6795 0.185 Uiso 1 1 calc R . . H1C H 0.7264 0.0778 0.6731 0.185 Uiso 1 1 calc R . . C2 C 0.63636(7) 0.04140(7) 0.82236(17) 0.0658(5) Uani 1 1 d U . . C3 C 0.67383(7) 0.09743(7) 0.93939(16) 0.0707(5) Uani 1 1 d U . . H3 H 0.7225 0.1292 0.9142 0.085 Uiso 1 1 calc R . . C4 C 0.64662(6) 0.11107(5) 1.08924(14) 0.0492(4) Uani 1 1 d U . . C5 C 0.69618(6) 0.16709(6) 1.21254(14) 0.0523(4) Uani 1 1 d U . . C6 C 0.76829(7) 0.20942(8) 1.18421(18) 0.0811(6) Uani 1 1 d U . . H6 H 0.7887 0.2043 1.0801 0.097 Uiso 1 1 calc R . . C7 C 0.44798(8) 0.18938(6) 0.30488(18) 0.0747(5) Uani 1 1 d U . . H7 H 0.4257 0.1397 0.2841 0.090 Uiso 1 1 calc R . . C8 C 0.48566(7) 0.21604(5) 0.45357(15) 0.0599(4) Uani 1 1 d U . . C9 C 0.51776(10) 0.28798(7) 0.4790(2) 0.1398(7) Uani 1 1 d U . . H9 H 0.5461 0.3087 0.5791 0.168 Uiso 1 1 calc R . . C10 C 0.50898(10) 0.33049(7) 0.3595(2) 0.1226(6) Uani 1 1 d U . . H10 H 0.5304 0.3800 0.3814 0.147 Uiso 1 1 calc R . . C11 C 0.49173(7) 0.16820(5) 0.58158(15) 0.0579(4) Uani 1 1 d U . . C12 C 0.48633(6) 0.10535(5) 0.53502(14) 0.0510(3) Uani 1 1 d U . . H12 H 0.4808 0.0918 0.4165 0.061 Uiso 1 1 calc R . . C13 C 0.48889(7) 0.06181(5) 0.65811(14) 0.0544(4) Uani 1 1 d U . . H13 H 0.4834 0.0177 0.6211 0.065 Uiso 1 1 calc R . . C14 C 0.50786(9) 0.13951(6) 0.87155(17) 0.0906(5) Uani 1 1 d U . . H14 H 0.5158 0.1523 0.9905 0.109 Uiso 1 1 calc R . . C15 C 0.50667(9) 0.18665(6) 0.75700(17) 0.0980(5) Uani 1 1 d U . . H15 H 0.5159 0.2319 0.7959 0.118 Uiso 1 1 calc R . . N1 N 0.49842(5) 0.07658(4) 0.82502(11) 0.0483(3) Uani 1 1 d U . . O1 O 0.58200(4) 0.07892(4) 1.13490(9) 0.0472(3) Uani 1 1 d U . . O2 O 0.57230(4) -0.00546(4) 0.83303(10) 0.0493(3) Uani 1 1 d U . . Zn1 Zn 0.5000 0.0000 1.0000 0.03920(6) Uani 1 2 d S . . O4 O 0.66190(19) 0.30762(13) 0.1222(4) 0.0396(14) Uani 0.1608(8) 1 d PD . 1 H4A H 0.7033 0.3280 0.0884 0.048 Uiso 0.1608(8) 1 d PR . 1 C18 C 0.6466(2) 0.3496(2) 0.2421(7) 0.096(4) Uani 0.1608(8) 1 d PD . 1 H18A H 0.6711 0.3642 0.3501 0.144 Uiso 0.1608(8) 1 d PR . 1 H18B H 0.6532 0.3896 0.1756 0.144 Uiso 0.1608(8) 1 d PR . 1 H18C H 0.5964 0.3189 0.2638 0.144 Uiso 0.1608(8) 1 d PR . 1 C17 C 0.6667 0.3333 -0.0425(4) 0.0678(15) Uani 0.517(2) 3 d SPD . 2 H17A H 0.6392 0.3566 -0.0534 0.102 Uiso 0.1725(8) 1 d PR . 2 H17B H 0.6367 0.2855 -0.0028 0.102 Uiso 0.1725(8) 1 d PR . 2 H17C H 0.7043 0.3586 0.0394 0.102 Uiso 0.1725(8) 1 d PR . 2 O3 O 0.69877(19) 0.3343(2) -0.2075(4) 0.0864(18) Uani 0.1725(8) 1 d PD . 2 H3A H 0.6983 0.3549 -0.2959 0.104 Uiso 0.1725(8) 1 d PR . 2 C16 C 0.96477(12) 0.27173(14) 0.8120(3) 0.160(2) Uani 0.25 1 d PD A 3 H16A H 1.0142 0.2847 0.7833 0.192 Uiso 0.25 1 d PR A 3 H16B H 0.9610 0.3151 0.8213 0.192 Uiso 0.25 1 d PR A 3 Cl1 Cl 0.93438(19) 0.22089(18) 0.9927(4) 0.2412(19) Uani 0.25 1 d PD A 3 Cl2 Cl 0.9129(2) 0.2157(2) 0.6531(4) 0.294(2) Uani 0.25 1 d PD A 3 C16W C 0.96477(12) 0.27173(14) 0.8120(3) 0.160(2) Uani 0.25 1 d PD B 4 H16C H 0.9820 0.2968 0.9086 0.192 Uiso 0.25 1 d PR B 4 H16D H 0.9682 0.3074 0.7102 0.192 Uiso 0.25 1 d PR B 4 Cl3 Cl 1.03004(15) 0.2587(2) 0.7343(7) 0.3155(14) Uani 0.25 1 d PDU B 4 Cl4 Cl 0.88525(17) 0.2016(2) 0.7766(7) 0.2731(14) Uani 0.25 1 d PDU B 4 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 0.0806(9) 0.1463(12) 0.0950(9) -0.0753(7) 0.0061(7) 0.0203(9) C2 0.0700(7) 0.0674(7) 0.0453(6) -0.0195(5) -0.0121(5) 0.0233(5) C3 0.0602(7) 0.0595(7) 0.0554(6) -0.0229(5) -0.0011(5) 0.0022(6) C4 0.0590(6) 0.0346(5) 0.0338(5) -0.0005(4) -0.0094(5) 0.0081(4) C5 0.0541(6) 0.0435(5) 0.0321(5) -0.0043(4) -0.0070(5) 0.0040(5) C6 0.0575(7) 0.0973(9) 0.0517(7) -0.0382(7) -0.0055(6) 0.0112(6) C7 0.1199(8) 0.0431(5) 0.0565(7) 0.0053(5) -0.0276(6) 0.0374(5) C8 0.1101(6) 0.0520(4) 0.0368(6) -0.0008(4) -0.0112(5) 0.0549(3) C9 0.2989(13) 0.0616(5) 0.0756(8) -0.0246(5) -0.1018(8) 0.1026(6) C10 0.2575(12) 0.0620(5) 0.0726(8) -0.0163(5) -0.0711(8) 0.0980(5) C11 0.1046(6) 0.0468(4) 0.0354(5) -0.0003(4) -0.0114(5) 0.0477(3) C12 0.0878(6) 0.0431(4) 0.0307(5) -0.0022(4) -0.0122(5) 0.0391(3) C13 0.0943(6) 0.0388(4) 0.0341(5) -0.0026(4) -0.0104(5) 0.0363(4) C14 0.1937(10) 0.0687(5) 0.0376(6) -0.0149(4) -0.0320(7) 0.0868(5) C15 0.2171(10) 0.0704(5) 0.0405(6) -0.0115(4) -0.0325(7) 0.0974(5) N1 0.0789(5) 0.0334(3) 0.0318(4) -0.0021(3) -0.0136(4) 0.0275(3) O1 0.0535(4) 0.0341(3) 0.0375(4) -0.0074(3) -0.0117(3) 0.0094(3) O2 0.0621(4) 0.0387(3) 0.0414(4) -0.0133(3) -0.0163(3) 0.0207(3) Zn1 0.05487(9) 0.02376(6) 0.03008(9) -0.00214(6) -0.01667(6) 0.01300(5) O4 0.063(2) 0.0318(16) 0.0292(19) -0.0093(12) -0.017(2) 0.0271(15) C18 0.039(3) 0.043(3) 0.197(10) 0.026(5) -0.027(5) 0.013(2) C17 0.0727(18) 0.0727(18) 0.058(3) 0.000 0.000 0.0364(9) O3 0.143(2) 0.107(2) 0.068(3) -0.014(2) -0.025(2) 0.1063(15) C16 0.211(3) 0.146(2) 0.172(4) -0.046(3) -0.082(3) 0.1262(18) Cl1 0.242(2) 0.201(3) 0.281(3) -0.004(2) 0.118(2) 0.1105(18) Cl2 0.271(4) 0.307(3) 0.298(3) 0.204(2) 0.064(3) 0.141(3) C16W 0.211(3) 0.146(2) 0.172(4) -0.046(3) -0.082(3) 0.1262(18) Cl3 0.3148(18) 0.3123(19) 0.314(2) 0.0066(16) -0.0017(16) 0.1528(12) Cl4 0.2700(18) 0.2744(18) 0.2829(19) -0.0087(16) 0.0042(16) 0.1422(11) _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 C2 1.513(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O2 1.2515(13) . ? C2 C3 1.4040(17) . ? C3 C4 1.3966(19) . ? C3 H3 0.9500 . ? C4 O1 1.2670(14) . ? C4 C5 1.4960(14) . ? C5 C10 1.352(2) 2_656 ? C5 C6 1.3822(17) . ? C6 C7 1.369(2) 2_656 ? C6 H6 0.9500 . ? C7 C8 1.3598(18) . ? C7 C6 1.369(2) 3_664 ? C7 H7 0.9500 . ? C8 C9 1.3714(17) . ? C8 C11 1.4876(18) . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C10 C5 1.352(2) 3_664 ? C10 H10 0.9500 . ? C11 C12 1.3602(18) . ? C11 C15 1.4030(18) . ? C12 C13 1.3618(17) . ? C12 H12 0.9500 . ? C13 N1 1.3185(14) . ? C13 H13 0.9500 . ? C14 N1 1.3278(18) . ? C14 C15 1.364(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? N1 Zn1 2.1573(10) . ? O1 Zn1 2.0368(7) . ? O2 Zn1 2.0815(9) . ? Zn1 O1 2.0368(7) 4_657 ? Zn1 O2 2.0815(9) 4_657 ? Zn1 N1 2.1573(10) 4_657 ? O4 O4 0.892(5) 2_655 ? O4 O4 0.892(5) 3_665 ? O4 C18 0.956(6) 2_655 ? O4 C18 1.324(6) 3_665 ? O4 C18 1.450(6) . ? O4 H4A 0.8223 . ? O4 H17B 1.0951 . ? O4 H17C 1.2108 . ? C18 O4 0.956(6) 3_665 ? C18 C18 1.185(10) 3_665 ? C18 C18 1.185(10) 2_655 ? C18 O4 1.324(6) 2_655 ? C18 H18A 0.9535 . ? C18 H18B 0.9575 . ? C18 H18C 0.9680 . ? C17 O3 1.447(4) . ? C17 O3 1.447(4) 3_665 ? C17 O3 1.447(4) 2_655 ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O3 O3 1.191(8) 2_655 ? O3 O3 1.191(8) 3_665 ? O3 H3A 0.8184 . ? C16 Cl1 1.695(4) . ? C16 Cl2 1.699(4) . ? C16 H16A 0.9898 . ? C16 H16B 0.9900 . ? C16 H16C 0.8878 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 126.23(13) . . ? O2 C2 C1 117.25(11) . . ? C3 C2 C1 116.50(12) . . ? C4 C3 C2 126.38(12) . . ? C4 C3 H3 116.8 . . ? C2 C3 H3 116.8 . . ? O1 C4 C3 125.72(10) . . ? O1 C4 C5 114.91(10) . . ? C3 C4 C5 119.36(11) . . ? C10 C5 C6 117.29(12) 2_656 . ? C10 C5 C4 118.84(11) 2_656 . ? C6 C5 C4 123.86(12) . . ? C7 C6 C5 120.57(13) 2_656 . ? C7 C6 H6 119.7 2_656 . ? C5 C6 H6 119.7 . . ? C8 C7 C6 122.15(12) . 3_664 ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 3_664 . ? C7 C8 C9 117.51(13) . . ? C7 C8 C11 120.48(10) . . ? C9 C8 C11 122.01(11) . . ? C8 C9 C10 120.29(14) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 122.11(12) 3_664 . ? C5 C10 H10 118.9 3_664 . ? C9 C10 H10 118.9 . . ? C12 C11 C15 115.69(12) . . ? C12 C11 C8 122.28(11) . . ? C15 C11 C8 121.96(12) . . ? C11 C12 C13 120.09(11) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? N1 C13 C12 124.61(11) . . ? N1 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? N1 C14 C15 123.25(12) . . ? N1 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? C14 C15 C11 119.94(13) . . ? C14 C15 H15 120.0 . . ? C11 C15 H15 120.0 . . ? C13 N1 C14 116.08(11) . . ? C13 N1 Zn1 118.99(8) . . ? C14 N1 Zn1 124.92(8) . . ? C4 O1 Zn1 125.80(7) . . ? C2 O2 Zn1 124.01(9) . . ? O1 Zn1 O1 180.00(6) . 4_657 ? O1 Zn1 O2 89.79(3) . . ? O1 Zn1 O2 90.21(3) 4_657 . ? O1 Zn1 O2 90.21(3) . 4_657 ? O1 Zn1 O2 89.79(3) 4_657 4_657 ? O2 Zn1 O2 180.00(3) . 4_657 ? O1 Zn1 N1 90.84(3) . . ? O1 Zn1 N1 89.16(3) 4_657 . ? O2 Zn1 N1 87.74(4) . . ? O2 Zn1 N1 92.26(4) 4_657 . ? O1 Zn1 N1 89.16(3) . 4_657 ? O1 Zn1 N1 90.84(3) 4_657 4_657 ? O2 Zn1 N1 92.26(4) . 4_657 ? O2 Zn1 N1 87.74(4) 4_657 4_657 ? N1 Zn1 N1 180.00(3) . 4_657 ? O4 O4 O4 60.000(1) 2_655 3_665 ? O4 O4 C18 103.2(4) 2_655 2_655 ? O4 O4 C18 91.5(5) 3_665 2_655 ? O4 O4 C18 46.2(3) 2_655 3_665 ? O4 O4 C18 79.0(2) 3_665 3_665 ? C18 O4 C18 60.0(6) 2_655 3_665 ? O4 O4 C18 63.8(3) 2_655 . ? O4 O4 C18 39.9(3) 3_665 . ? C18 O4 C18 54.4(5) 2_655 . ? C18 O4 C18 50.3(4) 3_665 . ? O4 O4 H4A 52.9 2_655 . ? O4 O4 H4A 109.4 3_665 . ? C18 O4 H4A 121.3 2_655 . ? C18 O4 H4A 70.8 3_665 . ? C18 O4 H4A 113.4 . . ? O4 O4 H17B 115.0 2_655 . ? O4 O4 H17B 91.6 3_665 . ? C18 O4 H17B 137.2 2_655 . ? C18 O4 H17B 161.2 3_665 . ? C18 O4 H17B 128.1 . . ? H4A O4 H17B 97.5 . . ? O4 O4 H17C 33.5 2_655 . ? O4 O4 H17C 73.9 3_665 . ? C18 O4 H17C 135.9 2_655 . ? C18 O4 H17C 76.3 3_665 . ? C18 O4 H17C 94.0 . . ? H4A O4 H17C 37.9 . . ? H17B O4 H17C 85.5 . . ? O4 C18 C18 84.5(4) 3_665 3_665 ? O4 C18 C18 75.6(4) 3_665 2_655 ? C18 C18 C18 60.0 3_665 2_655 ? O4 C18 O4 42.3(4) 3_665 2_655 ? C18 C18 O4 44.4(3) 3_665 2_655 ? C18 C18 O4 70.3(3) 2_655 2_655 ? O4 C18 O4 36.8(3) 3_665 . ? C18 C18 O4 59.4(2) 3_665 . ? C18 C18 O4 41.0(2) 2_655 . ? O4 C18 O4 37.2(2) 2_655 . ? O4 C18 H18A 150.2 3_665 . ? C18 C18 H18A 65.9 3_665 . ? C18 C18 H18A 91.4 2_655 . ? O4 C18 H18A 108.2 2_655 . ? O4 C18 H18A 120.1 . . ? O4 C18 H18B 72.0 3_665 . ? C18 C18 H18B 105.0 3_665 . ? C18 C18 H18B 145.6 2_655 . ? O4 C18 H18B 77.9 2_655 . ? O4 C18 H18B 104.6 . . ? H18A C18 H18B 111.2 . . ? O4 C18 H18C 96.8 3_665 . ? C18 C18 H18C 144.8 3_665 . ? C18 C18 H18C 86.2 2_655 . ? O4 C18 H18C 135.9 2_655 . ? O4 C18 H18C 102.1 . . ? H18A C18 H18C 109.2 . . ? H18B C18 H18C 108.8 . . ? O3 C17 O3 48.6(3) . 3_665 ? O3 C17 O3 48.6(3) . 2_655 ? O3 C17 O3 48.6(3) 3_665 2_655 ? O3 C17 H4A 111.4 . . ? O3 C17 H4A 141.7 3_665 . ? O3 C17 H4A 149.4 2_655 . ? O3 C17 H17A 109.7 . . ? O3 C17 H17A 85.0 3_665 . ? O3 C17 H17A 61.2 2_655 . ? H4A C17 H17A 132.2 . . ? O3 C17 H17B 111.0 . . ? O3 C17 H17B 81.8 3_665 . ? O3 C17 H17B 128.8 2_655 . ? H4A C17 H17B 77.0 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 107.7 . . ? O3 C17 H17C 156.2 3_665 . ? O3 C17 H17C 121.2 2_655 . ? H4A C17 H17C 34.1 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 O3 O3 60.000(1) 2_655 3_665 ? O3 O3 C17 65.69(15) 2_655 . ? O3 O3 C17 65.69(15) 3_665 . ? O3 O3 H3A 61.6 2_655 . ? O3 O3 H3A 90.3 3_665 . ? C17 O3 H3A 127.2 . . ? Cl1 C16 Cl2 102.92(19) . . ? Cl1 C16 H16A 112.6 . . ? Cl2 C16 H16A 106.3 . . ? Cl1 C16 H16B 111.8 . . ? Cl2 C16 H16B 113.2 . . ? H16A C16 H16B 109.9 . . ? Cl1 C16 H16C 67.4 . . ? Cl2 C16 H16C 166.1 . . ? H16A C16 H16C 87.0 . . ? H16B C16 H16C 64.2 . . ? Cl1 C16 H16D 158.6 . . ? Cl2 C16 H16D 76.9 . . ? H16A C16 H16D 87.5 . . ? H16B C16 H16D 51.4 . . ? H16C C16 H16D 108.3 . . ? C16 Cl1 H16C 31.2 . . ? C16 Cl2 H16D 35.9 . . ? 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 O2 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 -178.68(17) . . . . ? C2 C3 C4 O1 -7.1(3) . . . . ? C2 C3 C4 C5 171.61(15) . . . . ? O1 C4 C5 C10 0.6(2) . . . 2_656 ? C3 C4 C5 C10 -178.22(16) . . . 2_656 ? O1 C4 C5 C6 -178.14(15) . . . . ? C3 C4 C5 C6 3.0(2) . . . . ? C10 C5 C6 C7 2.6(3) 2_656 . . 2_656 ? C4 C5 C6 C7 -178.56(15) . . . 2_656 ? C6 C7 C8 C9 -0.6(3) 3_664 . . . ? C6 C7 C8 C11 179.90(15) 3_664 . . . ? C7 C8 C9 C10 2.6(3) . . . . ? C11 C8 C9 C10 -177.92(17) . . . . ? C8 C9 C10 C5 -2.0(3) . . . 3_664 ? C7 C8 C11 C12 26.3(2) . . . . ? C9 C8 C11 C12 -153.19(16) . . . . ? C7 C8 C11 C15 -156.69(15) . . . . ? C9 C8 C11 C15 23.8(2) . . . . ? C15 C11 C12 C13 5.94(19) . . . . ? C8 C11 C12 C13 -176.88(12) . . . . ? C11 C12 C13 N1 -2.0(2) . . . . ? N1 C14 C15 C11 3.0(3) . . . . ? C12 C11 C15 C14 -6.4(2) . . . . ? C8 C11 C15 C14 176.37(15) . . . . ? C12 C13 N1 C14 -1.80(19) . . . . ? C12 C13 N1 Zn1 179.50(10) . . . . ? C15 C14 N1 C13 1.2(2) . . . . ? C15 C14 N1 Zn1 179.84(13) . . . . ? C3 C4 O1 Zn1 -1.3(2) . . . . ? C5 C4 O1 Zn1 179.95(8) . . . . ? C3 C2 O2 Zn1 13.2(2) . . . . ? C1 C2 O2 Zn1 -167.95(12) . . . . ? C4 O1 Zn1 O1 148(18) . . . 4_657 ? C4 O1 Zn1 O2 9.63(10) . . . . ? C4 O1 Zn1 O2 -170.37(10) . . . 4_657 ? C4 O1 Zn1 N1 -78.10(11) . . . . ? C4 O1 Zn1 N1 101.90(11) . . . 4_657 ? C2 O2 Zn1 O1 -15.31(11) . . . . ? C2 O2 Zn1 O1 164.69(11) . . . 4_657 ? C2 O2 Zn1 O2 -161(100) . . . 4_657 ? C2 O2 Zn1 N1 75.54(11) . . . . ? C2 O2 Zn1 N1 -104.46(11) . . . 4_657 ? C13 N1 Zn1 O1 139.22(9) . . . . ? C14 N1 Zn1 O1 -39.35(12) . . . . ? C13 N1 Zn1 O1 -40.78(9) . . . 4_657 ? C14 N1 Zn1 O1 140.65(12) . . . 4_657 ? C13 N1 Zn1 O2 49.46(9) . . . . ? C14 N1 Zn1 O2 -129.11(12) . . . . ? C13 N1 Zn1 O2 -130.54(9) . . . 4_657 ? C14 N1 Zn1 O2 50.89(12) . . . 4_657 ? C13 N1 Zn1 N1 -84(100) . . . 4_657 ? C14 N1 Zn1 N1 98(100) . . . 4_657 ? O4 O4 C18 O4 73.8(3) 2_655 . . 3_665 ? C18 O4 C18 O4 -154.5(9) 2_655 . . 3_665 ? C18 O4 C18 O4 127.3(7) 3_665 . . 3_665 ? O4 O4 C18 C18 -53.6(4) 2_655 . . 3_665 ? O4 O4 C18 C18 -127.3(7) 3_665 . . 3_665 ? C18 O4 C18 C18 78.2(3) 2_655 . . 3_665 ? O4 O4 C18 C18 -131.8(5) 2_655 . . 2_655 ? O4 O4 C18 C18 154.5(9) 3_665 . . 2_655 ? C18 O4 C18 C18 -78.2(3) 3_665 . . 2_655 ? O4 O4 C18 O4 -73.8(3) 3_665 . . 2_655 ? C18 O4 C18 O4 131.8(5) 2_655 . . 2_655 ? C18 O4 C18 O4 53.6(4) 3_665 . . 2_655 ? O3 C17 O3 O3 66.55(9) 3_665 . . 2_655 ? O3 C17 O3 O3 -66.55(9) 2_655 . . 3_665 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.58 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.841 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.133 # Attachment '71023b.cif' data_71023b _database_code_depnum_ccdc_archive 'CCDC 833168' #TrackingRef '71023b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H62 Cu3 N6 O19' _chemical_formula_weight 1289.72 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 26.718(5) _cell_length_b 26.718(5) _cell_length_c 7.7553(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4794.3(17) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2457 _cell_measurement_theta_min 2.640 _cell_measurement_theta_max 25.416 _exptl_crystal_description bar _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2001 _exptl_absorpt_coefficient_mu 1.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6194 _exptl_absorpt_correction_T_max 0.9200 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8105 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1877 _reflns_number_gt 1549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+1.4160P] 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 1877 _refine_ls_number_parameters 121 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.3333 0.1667 0.6667 0.0345(2) Uani 1 2 d S . . C1 C 0.1815(2) 0.1193(2) 0.3721(6) 0.0905(16) Uani 1 1 d . . . H1A H 0.1994 0.1285 0.2605 0.136 Uiso 1 1 calc R . . H1B H 0.1554 0.1340 0.3811 0.136 Uiso 1 1 calc R . . H1C H 0.1606 0.0782 0.3873 0.136 Uiso 1 1 calc R . . C2 C 0.22706(15) 0.14637(16) 0.5086(4) 0.0542(9) Uani 1 1 d . . . C3 C 0.22438(16) 0.18590(17) 0.6211(4) 0.0627(10) Uani 1 1 d . . . H3 H 0.1975 0.1973 0.5962 0.075 Uiso 1 1 calc R . . C4 C 0.25830(13) 0.20955(13) 0.7662(4) 0.0407(7) Uani 1 1 d . . . C5 C 0.24182(13) 0.24136(13) 0.8922(4) 0.0393(7) Uani 1 1 d . . . C6 C 0.20678(14) 0.26380(14) 0.8509(4) 0.0463(8) Uani 1 1 d . . . H6 H 0.1942 0.2622 0.7381 0.056 Uiso 1 1 calc R . . C7 C 0.26021(17) 0.24769(17) 1.0617(4) 0.0613(10) Uani 1 1 d . . . H7 H 0.2851 0.2346 1.0958 0.074 Uiso 1 1 calc R . . C8 C 0.24168(17) 0.27327(18) 1.1797(4) 0.0641(11) Uani 1 1 d . . . H8 H 0.2544 0.2766 1.2930 0.077 Uiso 1 1 calc R . . C9 C 0.19070(14) 0.28851(15) 0.9778(4) 0.0494(8) Uani 1 1 d . . . H9 H 0.1667 0.3030 0.9469 0.059 Uiso 1 1 calc R . . N1 N 0.20679(12) 0.29335(12) 1.1414(3) 0.0483(7) Uani 1 1 d . . . O1 O 0.30168(9) 0.20490(8) 0.8085(2) 0.0402(5) Uani 1 1 d . . . O2 O 0.26452(9) 0.13103(9) 0.5132(3) 0.0460(5) Uani 1 1 d . . . O3 O 0.0000 0.0000 0.5000 0.435(17) Uiso 1 6 d SD . . O4 O 0.0451(4) 0.0998(7) 0.0845(14) 0.599(14) Uiso 1 1 d D . . H4A H 0.0703 0.1359 0.0952 0.719 Uiso 1 1 d RD . . H3B H 0.0361 0.0124 0.4833 0.719 Uiso 0.17 1 d PRD . . H4B H 0.0367 0.0835 0.1840 0.719 Uiso 1 1 d RD . . H3A H -0.0073 0.0128 0.5941 0.719 Uiso 0.17 1 d PRD . . 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 0.0436(3) 0.0341(3) 0.0317(3) -0.00014(19) 0.00314(19) 0.0239(2) C1 0.092(3) 0.124(4) 0.080(3) -0.053(3) -0.036(3) 0.072(3) C2 0.059(2) 0.067(2) 0.0441(19) -0.0119(17) -0.0073(16) 0.0370(19) C3 0.069(2) 0.090(3) 0.054(2) -0.024(2) -0.0164(18) 0.058(2) C4 0.0468(18) 0.0451(17) 0.0373(17) 0.0004(13) 0.0054(13) 0.0283(15) C5 0.0432(17) 0.0453(17) 0.0357(16) -0.0020(13) -0.0005(13) 0.0267(14) C6 0.0564(19) 0.062(2) 0.0329(16) -0.0028(15) -0.0050(14) 0.0386(17) C7 0.081(3) 0.091(3) 0.047(2) -0.0145(19) -0.0141(18) 0.069(2) C8 0.089(3) 0.097(3) 0.0387(19) -0.0170(19) -0.0155(18) 0.071(3) C9 0.058(2) 0.069(2) 0.0415(18) -0.0038(16) -0.0055(16) 0.0470(18) N1 0.0578(17) 0.0657(18) 0.0363(15) -0.0069(13) -0.0024(12) 0.0421(15) O1 0.0512(12) 0.0456(12) 0.0358(11) -0.0022(9) 0.0005(9) 0.0331(10) O2 0.0549(13) 0.0474(13) 0.0419(12) -0.0101(9) -0.0020(10) 0.0302(11) _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 O1 1.9572(18) 13_556 ? Cu1 O1 1.9573(18) . ? Cu1 O2 1.988(2) 13_556 ? Cu1 O2 1.988(2) . ? Cu1 N1 2.377(2) 11_557 ? Cu1 N1 2.377(2) 5_554 ? C1 C2 1.498(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O2 1.258(4) . ? C2 C3 1.399(5) . ? C3 C4 1.384(4) . ? C3 H3 0.9300 . ? C4 O1 1.269(3) . ? C4 C5 1.498(4) . ? C5 C6 1.378(4) . ? C5 C7 1.384(5) . ? C6 C9 1.368(4) . ? C6 H6 0.9300 . ? C7 C8 1.374(4) . ? C7 H7 0.9300 . ? C8 N1 1.321(4) . ? C8 H8 0.9300 . ? C9 N1 1.325(4) . ? C9 H9 0.9300 . ? N1 Cu1 2.377(2) 9 ? O3 H3B 0.8584 . ? O3 H3A 0.8681 . ? O4 H4A 0.8619 . ? O4 H4B 0.8588 . ? 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 Cu1 O1 180.0 13_556 . ? O1 Cu1 O2 92.81(8) 13_556 13_556 ? O1 Cu1 O2 87.20(8) . 13_556 ? O1 Cu1 O2 87.20(8) 13_556 . ? O1 Cu1 O2 92.80(8) . . ? O2 Cu1 O2 180.0 13_556 . ? O1 Cu1 N1 89.94(9) 13_556 11_557 ? O1 Cu1 N1 90.06(9) . 11_557 ? O2 Cu1 N1 87.03(9) 13_556 11_557 ? O2 Cu1 N1 92.97(9) . 11_557 ? O1 Cu1 N1 90.07(9) 13_556 5_554 ? O1 Cu1 N1 89.93(9) . 5_554 ? O2 Cu1 N1 92.97(9) 13_556 5_554 ? O2 Cu1 N1 87.02(9) . 5_554 ? N1 Cu1 N1 180.0 11_557 5_554 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 125.3(3) . . ? O2 C2 C1 116.7(3) . . ? C3 C2 C1 118.0(3) . . ? C4 C3 C2 125.6(3) . . ? C4 C3 H3 117.2 . . ? C2 C3 H3 117.2 . . ? O1 C4 C3 126.0(3) . . ? O1 C4 C5 115.4(3) . . ? C3 C4 C5 118.6(3) . . ? C6 C5 C7 116.4(3) . . ? C6 C5 C4 123.5(3) . . ? C7 C5 C4 120.1(3) . . ? C9 C6 C5 119.2(3) . . ? C9 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C5 120.0(3) . . ? C8 C7 H7 120.0 . . ? C5 C7 H7 120.0 . . ? N1 C8 C7 123.7(3) . . ? N1 C8 H8 118.1 . . ? C7 C8 H8 118.1 . . ? N1 C9 C6 124.8(3) . . ? N1 C9 H9 117.6 . . ? C6 C9 H9 117.6 . . ? C8 N1 C9 115.9(3) . . ? C8 N1 Cu1 127.6(2) . 9 ? C9 N1 Cu1 116.5(2) . 9 ? C4 O1 Cu1 124.06(19) . . ? C2 O2 Cu1 123.9(2) . . ? H3B O3 H3A 113.9 . . ? H4A O4 H4B 109.9 . . ? 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 O2 C2 C3 C4 -7.5(6) . . . . ? C1 C2 C3 C4 171.8(4) . . . . ? C2 C3 C4 O1 9.3(6) . . . . ? C2 C3 C4 C5 -167.4(3) . . . . ? O1 C4 C5 C6 162.4(3) . . . . ? C3 C4 C5 C6 -20.5(5) . . . . ? O1 C4 C5 C7 -20.0(5) . . . . ? C3 C4 C5 C7 157.1(4) . . . . ? C7 C5 C6 C9 -2.4(5) . . . . ? C4 C5 C6 C9 175.3(3) . . . . ? C6 C5 C7 C8 2.4(6) . . . . ? C4 C5 C7 C8 -175.4(3) . . . . ? C5 C7 C8 N1 -0.6(7) . . . . ? C5 C6 C9 N1 0.7(5) . . . . ? C7 C8 N1 C9 -1.2(6) . . . . ? C7 C8 N1 Cu1 176.0(3) . . . 9 ? C6 C9 N1 C8 1.2(5) . . . . ? C6 C9 N1 Cu1 -176.4(3) . . . 9 ? C3 C4 O1 Cu1 4.2(4) . . . . ? C5 C4 O1 Cu1 -178.98(18) . . . . ? O1 Cu1 O1 C4 27(3) 13_556 . . . ? O2 Cu1 O1 C4 167.0(2) 13_556 . . . ? O2 Cu1 O1 C4 -13.0(2) . . . . ? N1 Cu1 O1 C4 -106.0(2) 11_557 . . . ? N1 Cu1 O1 C4 74.0(2) 5_554 . . . ? C3 C2 O2 Cu1 -7.1(5) . . . . ? C1 C2 O2 Cu1 173.6(3) . . . . ? O1 Cu1 O2 C2 -165.5(3) 13_556 . . . ? O1 Cu1 O2 C2 14.4(3) . . . . ? O2 Cu1 O2 C2 -1.8(10) 13_556 . . . ? N1 Cu1 O2 C2 104.7(3) 11_557 . . . ? N1 Cu1 O2 C2 -75.3(3) 5_554 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.504 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.080 # Attachment '71216dm.cif' data_71216dm _database_code_depnum_ccdc_archive 'CCDC 833169' #TrackingRef '71216dm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H48 Cu3 N6 O12' _chemical_formula_weight 1163.60 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 26.473(4) _cell_length_b 26.473(4) _cell_length_c 7.635(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4633.8(17) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1163 _cell_measurement_theta_min 2.665 _cell_measurement_theta_max 19.103 _exptl_crystal_description plan _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1791 _exptl_absorpt_coefficient_mu 1.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7034 _exptl_absorpt_correction_T_max 0.9380 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8103 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.48 _reflns_number_total 1915 _reflns_number_gt 1304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^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 1915 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.85459(18) 0.62200(18) 0.3162(5) 0.0718(11) Uani 1 1 d . . . H1 H 0.8300 0.6362 0.2846 0.086 Uiso 1 1 calc R . . C2 C 0.9066(2) 0.60772(19) 0.5212(5) 0.0818(13) Uani 1 1 d . . . H2 H 0.9198 0.6117 0.6360 0.098 Uiso 1 1 calc R . . C3 C 0.88988(19) 0.47802(19) -0.1602(5) 0.0721(11) Uani 1 1 d . . . C4 C 0.88730(18) 0.51720(19) -0.0416(5) 0.0796(12) Uani 1 1 d . . . H4 H 0.8590 0.5274 -0.0626 0.095 Uiso 1 1 calc R . . C5 C 0.92259(17) 0.54211(15) 0.1032(4) 0.0581(10) Uani 1 1 d . . . C6 C 0.90614(16) 0.57436(15) 0.2301(4) 0.0572(9) Uani 1 1 d . . . C7 C 0.87083(17) 0.59699(17) 0.1892(4) 0.0668(10) Uani 1 1 d . . . H7 H 0.8581 0.5952 0.0747 0.080 Uiso 1 1 calc R . . C8 C 0.92479(19) 0.58146(19) 0.4024(5) 0.0791(13) Uani 1 1 d . . . H8 H 0.9499 0.5683 0.4376 0.095 Uiso 1 1 calc R . . C9 C 0.8427(2) 0.4516(2) -0.2961(6) 0.1105(18) Uani 1 1 d . . . H9A H 0.8578 0.4433 -0.3998 0.166 Uiso 1 1 calc R . . H9B H 0.8295 0.4784 -0.3240 0.166 Uiso 1 1 calc R . . H9C H 0.8107 0.4161 -0.2515 0.166 Uiso 1 1 calc R . . Cu1 Cu 1.0000 0.5000 0.0000 0.0499(3) Uani 1 2 d S . . N1 N 0.87131(14) 0.62755(14) 0.4818(4) 0.0659(8) Uani 1 1 d . . . O1 O 0.96725(11) 0.53863(10) 0.1418(3) 0.0577(6) Uani 1 1 d . . . O2 O 0.92739(12) 0.46298(11) -0.1600(3) 0.0685(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.091(3) 0.101(3) 0.045(2) -0.001(2) -0.004(2) 0.064(3) C2 0.115(4) 0.101(3) 0.051(2) -0.014(2) -0.019(2) 0.069(3) C3 0.083(3) 0.085(3) 0.048(2) -0.003(2) -0.003(2) 0.041(3) C4 0.091(3) 0.110(3) 0.062(2) -0.022(2) -0.019(2) 0.068(3) C5 0.071(3) 0.059(2) 0.045(2) 0.0086(17) 0.0050(19) 0.033(2) C6 0.065(2) 0.063(2) 0.0426(19) 0.0028(17) -0.0018(18) 0.032(2) C7 0.087(3) 0.087(3) 0.0402(19) 0.001(2) -0.003(2) 0.054(2) C8 0.099(3) 0.104(3) 0.061(2) -0.012(2) -0.018(2) 0.070(3) C9 0.123(4) 0.134(5) 0.090(4) -0.042(3) -0.040(3) 0.076(4) Cu1 0.0650(4) 0.0488(4) 0.0378(4) 0.0050(3) 0.0012(3) 0.0298(3) N1 0.084(2) 0.080(2) 0.0437(18) -0.0002(16) -0.0030(16) 0.049(2) O1 0.0683(16) 0.0636(15) 0.0460(13) 0.0039(11) -0.0008(12) 0.0365(13) O2 0.0843(19) 0.0703(17) 0.0583(16) -0.0047(13) -0.0017(14) 0.0441(16) _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 N1 1.323(4) . ? C1 C7 1.360(5) . ? C1 H1 0.9300 . ? C2 N1 1.314(5) . ? C2 C8 1.369(5) . ? C2 H2 0.9300 . ? C3 O2 1.241(4) . ? C3 C4 1.404(5) . ? C3 C9 1.500(5) . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 O1 1.266(4) . ? C5 C6 1.493(5) . ? C6 C7 1.375(5) . ? C6 C8 1.385(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cu1 O1 1.964(2) . ? Cu1 O1 1.964(2) 10_765 ? Cu1 O2 2.065(3) . ? Cu1 O2 2.065(3) 10_765 ? Cu1 N1 2.262(3) 5_654 ? Cu1 N1 2.262(3) 17 ? N1 Cu1 2.262(3) 9_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 N1 C1 C7 124.5(4) . . ? N1 C1 H1 117.8 . . ? C7 C1 H1 117.8 . . ? N1 C2 C8 123.5(4) . . ? N1 C2 H2 118.2 . . ? C8 C2 H2 118.2 . . ? O2 C3 C4 125.4(4) . . ? O2 C3 C9 117.6(4) . . ? C4 C3 C9 117.0(4) . . ? C5 C4 C3 126.6(4) . . ? C5 C4 H4 116.7 . . ? C3 C4 H4 116.7 . . ? O1 C5 C4 125.7(4) . . ? O1 C5 C6 116.1(3) . . ? C4 C5 C6 118.1(3) . . ? C7 C6 C8 115.5(3) . . ? C7 C6 C5 123.9(3) . . ? C8 C6 C5 120.5(3) . . ? C1 C7 C6 120.0(3) . . ? C1 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C2 C8 C6 120.4(4) . . ? C2 C8 H8 119.8 . . ? C6 C8 H8 119.8 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 Cu1 O1 180.00(10) . 10_765 ? O1 Cu1 O2 91.42(10) . . ? O1 Cu1 O2 88.58(10) 10_765 . ? O1 Cu1 O2 88.58(10) . 10_765 ? O1 Cu1 O2 91.42(10) 10_765 10_765 ? O2 Cu1 O2 180.00(12) . 10_765 ? O1 Cu1 N1 89.78(10) . 5_654 ? O1 Cu1 N1 90.22(10) 10_765 5_654 ? O2 Cu1 N1 87.52(10) . 5_654 ? O2 Cu1 N1 92.48(10) 10_765 5_654 ? O1 Cu1 N1 90.22(10) . 17 ? O1 Cu1 N1 89.78(10) 10_765 17 ? O2 Cu1 N1 92.48(10) . 17 ? O2 Cu1 N1 87.52(10) 10_765 17 ? N1 Cu1 N1 180.000(2) 5_654 17 ? C2 N1 C1 116.1(3) . . ? C2 N1 Cu1 127.4(3) . 9_665 ? C1 N1 Cu1 116.5(3) . 9_665 ? C5 O1 Cu1 125.5(2) . . ? C3 O2 Cu1 123.6(3) . . ? 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 O2 C3 C4 C5 -5.6(7) . . . . ? C9 C3 C4 C5 173.3(4) . . . . ? C3 C4 C5 O1 8.3(7) . . . . ? C3 C4 C5 C6 -169.4(4) . . . . ? O1 C5 C6 C7 160.5(3) . . . . ? C4 C5 C6 C7 -21.6(5) . . . . ? O1 C5 C6 C8 -21.8(5) . . . . ? C4 C5 C6 C8 156.1(4) . . . . ? N1 C1 C7 C6 1.3(6) . . . . ? C8 C6 C7 C1 -2.7(6) . . . . ? C5 C6 C7 C1 175.2(3) . . . . ? N1 C2 C8 C6 -0.1(7) . . . . ? C7 C6 C8 C2 2.2(6) . . . . ? C5 C6 C8 C2 -175.7(4) . . . . ? C8 C2 N1 C1 -1.4(7) . . . . ? C8 C2 N1 Cu1 176.0(3) . . . 9_665 ? C7 C1 N1 C2 0.9(6) . . . . ? C7 C1 N1 Cu1 -176.8(3) . . . 9_665 ? C4 C5 O1 Cu1 3.0(5) . . . . ? C6 C5 O1 Cu1 -179.2(2) . . . . ? O1 Cu1 O1 C5 172(100) 10_765 . . . ? O2 Cu1 O1 C5 -10.7(3) . . . . ? O2 Cu1 O1 C5 169.3(3) 10_765 . . . ? N1 Cu1 O1 C5 76.8(3) 5_654 . . . ? N1 Cu1 O1 C5 -103.2(3) 17 . . . ? C4 C3 O2 Cu1 -7.2(6) . . . . ? C9 C3 O2 Cu1 173.9(3) . . . . ? O1 Cu1 O2 C3 12.7(3) . . . . ? O1 Cu1 O2 C3 -167.3(3) 10_765 . . . ? O2 Cu1 O2 C3 61(100) 10_765 . . . ? N1 Cu1 O2 C3 -77.0(3) 5_654 . . . ? N1 Cu1 O2 C3 103.0(3) 17 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.389 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.069 # Attachment '90710cm.cif' data_90710cm _database_code_depnum_ccdc_archive 'CCDC 833170' #TrackingRef '90710cm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H62 Cu3 N6 O19' _chemical_formula_weight 1289.72 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 26.642(4) _cell_length_b 26.642(4) _cell_length_c 7.741(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4758.3(16) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1926 _cell_measurement_theta_min 2.648 _cell_measurement_theta_max 24.627 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2001 _exptl_absorpt_coefficient_mu 1.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8563 _exptl_absorpt_correction_T_max 0.9007 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7504 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1953 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^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 1953 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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 0.4530(2) 0.8482(2) 1.2979(6) 0.0671(15) Uani 1 1 d . . . H1A H 0.4551 0.8663 1.4070 0.101 Uiso 1 1 calc R . . H1B H 0.4736 0.8272 1.3053 0.101 Uiso 1 1 calc R . . H1C H 0.4132 0.8219 1.2693 0.101 Uiso 1 1 calc R . . C2 C 0.48004(17) 0.89386(17) 1.1601(5) 0.0397(9) Uani 1 1 d . . . C3 C 0.52031(19) 0.89152(18) 1.0491(5) 0.0476(11) Uani 1 1 d . . . H3 H 0.5323 0.8651 1.0759 0.057 Uiso 1 1 calc R . . C4 C 0.54388(15) 0.92529(15) 0.9021(4) 0.0298(8) Uani 1 1 d . . . C5 C 0.57552(14) 0.90853(14) 0.7763(4) 0.0288(8) Uani 1 1 d . . . C6 C 0.58129(18) 0.92709(18) 0.6056(5) 0.0429(10) Uani 1 1 d . . . H6 H 0.5680 0.9519 0.5722 0.051 Uiso 1 1 calc R . . C7 C 0.60674(18) 0.90857(18) 0.4871(5) 0.0447(10) Uani 1 1 d . . . H7 H 0.6101 0.9215 0.3739 0.054 Uiso 1 1 calc R . . C8 C 0.62234(16) 0.85682(16) 0.6895(5) 0.0345(9) Uani 1 1 d . . . H8 H 0.6367 0.8326 0.7197 0.041 Uiso 1 1 calc R . . C9 C 0.59794(15) 0.87320(15) 0.8176(5) 0.0328(8) Uani 1 1 d . . . H9 H 0.5965 0.8607 0.9306 0.039 Uiso 1 1 calc R . . Cu1 Cu 0.5000 1.0000 1.0000 0.0252(2) Uani 1 2 d S . . N1 N 0.62693(13) 0.87314(13) 0.5248(4) 0.0341(7) Uani 1 1 d . . . O2 O 0.46430(10) 0.93107(10) 1.1538(3) 0.0327(6) Uani 1 1 d . . . O1 O 0.53839(10) 0.96816(10) 0.8590(3) 0.0293(6) Uani 1 1 d . . . O4 O 0.3333 0.6667 0.1667 0.396(19) Uiso 1 6 d S . . H4B H 0.3125 0.6745 0.1013 0.476 Uiso 0.17 1 d PR . . H4A H 0.3666 0.6949 0.1419 0.476 Uiso 0.17 1 d PR . . O3 O 0.4465(8) 0.7188(8) 0.562(2) 0.462(10) Uiso 1 1 d . . . H3A H 0.4817 0.7443 0.5444 0.555 Uiso 1 1 d R . . H3B H 0.4287 0.7148 0.6565 0.555 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.095(4) 0.065(3) 0.056(3) 0.027(2) 0.040(3) 0.051(3) C2 0.048(2) 0.041(2) 0.032(2) 0.0052(17) 0.0095(18) 0.024(2) C3 0.071(3) 0.055(3) 0.039(3) 0.011(2) 0.019(2) 0.048(2) C4 0.0335(19) 0.036(2) 0.0255(19) -0.0025(15) 0.0008(15) 0.0215(17) C5 0.0331(19) 0.0325(19) 0.0232(19) -0.0011(15) 0.0030(15) 0.0181(16) C6 0.064(3) 0.060(3) 0.028(2) 0.0087(18) 0.0076(19) 0.049(2) C7 0.066(3) 0.060(3) 0.026(2) 0.0096(19) 0.0104(19) 0.045(2) C8 0.047(2) 0.044(2) 0.0268(19) 0.0019(17) 0.0015(17) 0.0333(19) C9 0.043(2) 0.042(2) 0.0220(18) 0.0033(16) 0.0003(16) 0.0272(18) Cu1 0.0259(4) 0.0322(4) 0.0212(3) -0.0023(2) 0.0002(2) 0.0173(3) N1 0.0453(18) 0.0409(17) 0.0251(17) 0.0006(13) 0.0018(14) 0.0283(15) O2 0.0363(14) 0.0401(14) 0.0269(13) 0.0033(11) 0.0071(11) 0.0231(12) O1 0.0352(13) 0.0393(14) 0.0213(12) -0.0009(10) 0.0015(10) 0.0246(11) _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 C2 1.504(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O2 1.256(4) . ? C2 C3 1.400(5) . ? C3 C4 1.390(5) . ? C3 H3 0.9300 . ? C4 O1 1.267(4) . ? C4 C5 1.495(5) . ? C5 C9 1.381(5) . ? C5 C6 1.391(5) . ? C6 C7 1.371(5) . ? C6 H6 0.9300 . ? C7 N1 1.332(5) . ? C7 H7 0.9300 . ? C8 N1 1.333(4) . ? C8 C9 1.371(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? Cu1 O1 1.955(2) 10_677 ? Cu1 O1 1.955(2) . ? Cu1 O2 1.987(2) . ? Cu1 O2 1.987(2) 10_677 ? Cu1 N1 2.359(3) 9_565 ? Cu1 N1 2.359(3) 15_556 ? N1 Cu1 2.359(3) 5_664 ? O4 H4B 0.8500 . ? O4 H4A 0.8499 . ? O3 H3A 0.8500 . ? O3 H3B 0.8500 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 125.2(3) . . ? O2 C2 C1 117.0(3) . . ? C3 C2 C1 117.8(4) . . ? C4 C3 C2 125.6(3) . . ? C4 C3 H3 117.2 . . ? C2 C3 H3 117.2 . . ? O1 C4 C3 125.5(3) . . ? O1 C4 C5 115.8(3) . . ? C3 C4 C5 118.7(3) . . ? C9 C5 C6 117.0(3) . . ? C9 C5 C4 123.6(3) . . ? C6 C5 C4 119.4(3) . . ? C7 C6 C5 119.6(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N1 C7 C6 123.8(3) . . ? N1 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? N1 C8 C9 124.7(3) . . ? N1 C8 H8 117.7 . . ? C9 C8 H8 117.7 . . ? C8 C9 C5 119.0(3) . . ? C8 C9 H9 120.5 . . ? C5 C9 H9 120.5 . . ? O1 Cu1 O1 180.000(1) 10_677 . ? O1 Cu1 O2 87.37(10) 10_677 . ? O1 Cu1 O2 92.63(9) . . ? O1 Cu1 O2 92.63(9) 10_677 10_677 ? O1 Cu1 O2 87.37(10) . 10_677 ? O2 Cu1 O2 180.00(11) . 10_677 ? O1 Cu1 N1 90.13(10) 10_677 9_565 ? O1 Cu1 N1 89.87(10) . 9_565 ? O2 Cu1 N1 86.90(10) . 9_565 ? O2 Cu1 N1 93.10(10) 10_677 9_565 ? O1 Cu1 N1 89.87(10) 10_677 15_556 ? O1 Cu1 N1 90.13(10) . 15_556 ? O2 Cu1 N1 93.10(10) . 15_556 ? O2 Cu1 N1 86.90(10) 10_677 15_556 ? N1 Cu1 N1 180.000(1) 9_565 15_556 ? C7 N1 C8 115.9(3) . . ? C7 N1 Cu1 127.8(2) . 5_664 ? C8 N1 Cu1 116.3(2) . 5_664 ? C2 O2 Cu1 124.0(2) . . ? C4 O1 Cu1 124.5(2) . . ? H4B O4 H4A 99.7 . . ? H3A O3 H3B 124.1 . . ? 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 O2 C2 C3 C4 -8.3(7) . . . . ? C1 C2 C3 C4 171.4(4) . . . . ? C2 C3 C4 O1 9.7(7) . . . . ? C2 C3 C4 C5 -166.2(4) . . . . ? O1 C4 C5 C9 163.5(3) . . . . ? C3 C4 C5 C9 -20.1(5) . . . . ? O1 C4 C5 C6 -19.1(5) . . . . ? C3 C4 C5 C6 157.2(4) . . . . ? C9 C5 C6 C7 2.0(6) . . . . ? C4 C5 C6 C7 -175.5(4) . . . . ? C5 C6 C7 N1 0.0(7) . . . . ? N1 C8 C9 C5 0.9(6) . . . . ? C6 C5 C9 C8 -2.3(5) . . . . ? C4 C5 C9 C8 175.1(3) . . . . ? C6 C7 N1 C8 -1.5(6) . . . . ? C6 C7 N1 Cu1 176.1(3) . . . 5_664 ? C9 C8 N1 C7 1.1(6) . . . . ? C9 C8 N1 Cu1 -176.8(3) . . . 5_664 ? C3 C2 O2 Cu1 -7.1(6) . . . . ? C1 C2 O2 Cu1 173.2(3) . . . . ? O1 Cu1 O2 C2 -164.9(3) 10_677 . . . ? O1 Cu1 O2 C2 15.1(3) . . . . ? O2 Cu1 O2 C2 -27(100) 10_677 . . . ? N1 Cu1 O2 C2 -74.6(3) 9_565 . . . ? N1 Cu1 O2 C2 105.4(3) 15_556 . . . ? C3 C4 O1 Cu1 4.8(5) . . . . ? C5 C4 O1 Cu1 -179.1(2) . . . . ? O1 Cu1 O1 C4 138(100) 10_677 . . . ? O2 Cu1 O1 C4 -14.0(3) . . . . ? O2 Cu1 O1 C4 166.0(3) 10_677 . . . ? N1 Cu1 O1 C4 72.9(3) 9_565 . . . ? N1 Cu1 O1 C4 -107.1(3) 15_556 . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.787 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.075 # Attachment '- 4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 839195' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Fe0 N2 O4 Zn' _chemical_formula_weight 541.88 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' Fe Fe 0.3463 0.8444 '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 Trigonal _symmetry_space_group_name_H-M P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 21.7437(16) _cell_length_b 21.7437(16) _cell_length_c 15.438(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6320.8(11) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3888 _cell_measurement_theta_min 2.163 _cell_measurement_theta_max 23.196 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.854 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8485 _exptl_absorpt_correction_T_max 0.8681 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33395 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7853 _reflns_number_gt 3752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^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 7853 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 0.831 _refine_ls_restrained_S_all 0.831 _refine_ls_shift/su_max 0.002 _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 Zn1 Zn 0.499499(19) 1.002124(16) 0.75148(2) 0.03857(12) Uani 1 1 d . . . O3 O 0.50240(10) 0.92252(9) 0.81803(11) 0.0446(5) Uani 1 1 d . . . O2 O 0.08009(9) 0.58474(10) 0.31626(10) 0.0428(5) Uani 1 1 d . . . O4 O 0.57848(10) 1.00812(10) 0.66881(11) 0.0467(5) Uani 1 1 d . . . O1 O -0.00261(10) 0.57482(10) 0.16391(11) 0.0468(5) Uani 1 1 d . . . N2 N 0.42089(12) 0.92574(11) 0.66530(14) 0.0480(7) Uani 1 1 d . . . N1 N 0.49799(12) 0.57770(12) 1.16057(13) 0.0417(6) Uani 1 1 d . . . C12 C 0.38215(15) 0.89276(14) 0.51963(15) 0.0503(8) Uani 1 1 d . . . H12 H 0.3924 0.9038 0.4599 0.060 Uiso 1 1 calc R . . C19 C 0.53453(17) 0.89116(14) 0.79475(17) 0.0471(8) Uani 1 1 d . . . C27 C 0.51588(15) 0.62049(14) 1.01463(17) 0.0490(8) Uani 1 1 d . . . H27 H 0.5261 0.6154 0.9561 0.059 Uiso 1 1 calc R . . C4 C 0.11258(14) 0.64960(17) 0.29420(17) 0.0476(8) Uani 1 1 d . . . C5 C 0.16833(15) 0.69888(16) 0.35481(17) 0.0528(9) Uani 1 1 d . . . C26 C 0.50282(15) 0.67474(15) 1.03973(18) 0.0475(8) Uani 1 1 d . . . C28 C 0.51342(15) 0.57502(15) 1.07771(17) 0.0493(8) Uani 1 1 d . . . H28 H 0.5235 0.5389 1.0611 0.059 Uiso 1 1 calc R . . C11 C 0.32213(16) 0.83559(16) 0.54180(17) 0.0590(9) Uani 1 1 d . . . C20 C 0.52780(17) 0.83338(15) 0.85616(17) 0.0498(8) Uani 1 1 d . . . C18 C 0.57571(18) 0.90471(16) 0.72108(19) 0.0665(10) Uani 1 1 d . . . H18 H 0.5912 0.8720 0.7074 0.080 Uiso 1 1 calc R . . C3 C 0.10010(16) 0.67520(16) 0.21840(19) 0.0695(10) Uani 1 1 d . . . H3 H 0.1324 0.7236 0.2053 0.083 Uiso 1 1 calc R . . C2 C 0.04448(17) 0.63751(19) 0.15765(19) 0.0594(9) Uani 1 1 d . . . C13 C 0.43018(15) 0.93665(15) 0.58020(17) 0.0572(9) Uani 1 1 d . . . H13 H 0.4724 0.9771 0.5604 0.069 Uiso 1 1 calc R . . C17 C 0.59655(17) 0.96259(17) 0.66489(19) 0.0587(9) Uani 1 1 d . . . C23 C 0.51075(17) 0.72850(15) 0.97431(17) 0.0507(8) Uani 1 1 d . . . C8 C 0.26836(16) 0.78662(16) 0.47979(18) 0.0652(10) Uani 1 1 d . . . C25 C 0.4817(2) 0.81439(17) 0.9226(2) 0.0764(11) Uani 1 1 d . . . H25 H 0.4548 0.8377 0.9285 0.092 Uiso 1 1 calc R . . C30 C 0.48659(19) 0.67743(16) 1.12436(18) 0.0707(11) Uani 1 1 d . . . H30 H 0.4756 0.7125 1.1431 0.085 Uiso 1 1 calc R . . C24 C 0.47131(19) 0.76307(17) 0.9824(2) 0.0765(11) Uani 1 1 d . . . H24 H 0.4381 0.7514 1.0283 0.092 Uiso 1 1 calc R . . C7 C 0.26550(17) 0.81118(17) 0.39809(19) 0.0729(11) Uani 1 1 d . . . H7 H 0.2986 0.8589 0.3829 0.088 Uiso 1 1 calc R . . C6 C 0.21590(17) 0.76799(16) 0.33869(18) 0.0672(10) Uani 1 1 d . . . H6 H 0.2148 0.7873 0.2839 0.081 Uiso 1 1 calc R . . C15 C 0.3177(2) 0.8192(2) 0.6332(2) 0.132(2) Uani 1 1 d . . . H15 H 0.2806 0.7752 0.6547 0.159 Uiso 1 1 calc R . . C1 C 0.04459(19) 0.67972(18) 0.0797(2) 0.0978(14) Uani 1 1 d . . . H1A H 0.0491 0.6574 0.0268 0.147 Uiso 1 1 calc R . . H1B H 0.0847 0.7284 0.0839 0.147 Uiso 1 1 calc R . . H1C H 0.0000 0.6807 0.0779 0.147 Uiso 1 1 calc R . . C22 C 0.55678(18) 0.74659(18) 0.90613(18) 0.0702(10) Uani 1 1 d . . . H22 H 0.5838 0.7236 0.8992 0.084 Uiso 1 1 calc R . . C29 C 0.48611(18) 0.62921(17) 1.18283(19) 0.0693(10) Uani 1 1 d . . . H29 H 0.4768 0.6334 1.2420 0.083 Uiso 1 1 calc R . . C21 C 0.56459(19) 0.79794(17) 0.84701(19) 0.0720(11) Uani 1 1 d . . . H21 H 0.5960 0.8087 0.7994 0.086 Uiso 1 1 calc R . . C9 C 0.2182(2) 0.71939(19) 0.4975(2) 0.1242(19) Uani 1 1 d . . . H9 H 0.2148 0.7026 0.5551 0.149 Uiso 1 1 calc R . . C10 C 0.1722(2) 0.6742(2) 0.4374(2) 0.135(2) Uani 1 1 d . . . H10 H 0.1424 0.6255 0.4515 0.162 Uiso 1 1 calc R . . C16 C 0.6451(2) 0.9693(2) 0.5889(2) 0.1169(17) Uani 1 1 d . . . H16A H 0.6271 0.9790 0.5355 0.175 Uiso 1 1 calc R . . H16B H 0.6459 0.9249 0.5824 0.175 Uiso 1 1 calc R . . H16C H 0.6933 1.0084 0.6002 0.175 Uiso 1 1 calc R . . C14 C 0.3664(2) 0.8664(2) 0.68692(19) 0.123(2) Uani 1 1 d . . . H14 H 0.3602 0.8551 0.7469 0.148 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0514(2) 0.02301(16) 0.03036(16) 0.00199(11) -0.01414(12) 0.01044(13) O3 0.0648(14) 0.0336(12) 0.0368(11) 0.0053(9) -0.0028(10) 0.0257(11) O2 0.0283(11) 0.0489(13) 0.0334(11) -0.0110(9) -0.0081(8) 0.0060(10) O4 0.0610(14) 0.0374(12) 0.0355(11) 0.0068(9) -0.0059(9) 0.0200(11) O1 0.0353(12) 0.0568(14) 0.0430(12) -0.0137(10) -0.0140(9) 0.0189(11) N2 0.0557(17) 0.0314(14) 0.0326(14) -0.0002(11) -0.0134(12) 0.0035(13) N1 0.0603(16) 0.0553(16) 0.0277(13) 0.0061(11) 0.0090(11) 0.0427(14) C12 0.062(2) 0.0445(19) 0.0159(14) 0.0072(13) -0.0095(14) 0.0056(16) C19 0.073(2) 0.0323(17) 0.0345(18) 0.0036(14) -0.0088(16) 0.0254(17) C27 0.070(2) 0.0455(19) 0.0408(18) 0.0076(15) 0.0086(15) 0.0355(17) C4 0.0337(18) 0.058(2) 0.0345(18) -0.0087(16) 0.0015(14) 0.0107(16) C5 0.0394(18) 0.049(2) 0.0350(18) -0.0093(15) -0.0002(14) -0.0040(16) C26 0.067(2) 0.0490(19) 0.0409(18) 0.0103(15) 0.0056(15) 0.0397(17) C28 0.077(2) 0.059(2) 0.0324(17) 0.0096(14) 0.0035(15) 0.0493(18) C11 0.056(2) 0.050(2) 0.0282(17) 0.0028(14) -0.0108(15) -0.0055(17) C20 0.081(2) 0.0403(19) 0.0323(18) 0.0058(14) 0.0031(16) 0.0333(18) C18 0.103(3) 0.060(2) 0.054(2) 0.0280(17) 0.0202(19) 0.054(2) C3 0.065(2) 0.057(2) 0.048(2) 0.0018(17) -0.0122(17) 0.0010(18) C2 0.054(2) 0.076(3) 0.0368(19) -0.0114(18) -0.0123(16) 0.024(2) C13 0.054(2) 0.0449(19) 0.0338(18) 0.0149(14) -0.0096(15) -0.0048(16) C17 0.072(2) 0.059(2) 0.047(2) 0.0171(17) 0.0086(17) 0.034(2) C23 0.083(2) 0.050(2) 0.0337(17) 0.0138(14) 0.0054(16) 0.0438(19) C8 0.061(2) 0.057(2) 0.0318(18) 0.0066(15) -0.0076(16) -0.0048(18) C25 0.129(3) 0.085(3) 0.059(2) 0.0345(19) 0.035(2) 0.086(3) C30 0.147(3) 0.066(2) 0.0380(19) 0.0256(16) 0.0310(19) 0.082(2) C24 0.120(3) 0.082(3) 0.068(2) 0.0377(19) 0.046(2) 0.081(2) C7 0.065(2) 0.052(2) 0.055(2) -0.0058(17) -0.0203(17) -0.0059(18) C6 0.073(2) 0.064(2) 0.0344(18) -0.0029(16) -0.0183(16) 0.011(2) C15 0.143(4) 0.081(3) 0.043(2) 0.000(2) -0.002(2) -0.042(3) C1 0.108(3) 0.084(3) 0.076(3) -0.005(2) -0.052(2) 0.029(2) C22 0.105(3) 0.094(3) 0.050(2) 0.0292(18) 0.0262(19) 0.078(2) C29 0.119(3) 0.067(2) 0.052(2) 0.0122(17) 0.0243(19) 0.069(2) C21 0.107(3) 0.075(2) 0.054(2) 0.0377(18) 0.0334(19) 0.061(2) C9 0.123(4) 0.080(3) 0.044(2) 0.0206(19) -0.042(2) -0.044(3) C10 0.121(4) 0.080(3) 0.063(3) 0.025(2) -0.049(2) -0.056(2) C16 0.203(5) 0.109(3) 0.089(3) 0.055(2) 0.076(3) 0.116(4) C14 0.111(3) 0.098(3) 0.0217(18) 0.0106(19) -0.0183(19) -0.051(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 Zn1 O2 2.0319(17) 6_666 ? Zn1 O3 2.0407(18) . ? Zn1 O1 2.0839(19) 6_666 ? Zn1 O4 2.0908(19) . ? Zn1 N2 2.147(2) . ? Zn1 N1 2.171(2) 5_567 ? O3 C19 1.248(3) . ? O2 C4 1.268(3) . ? O2 Zn1 2.0319(17) 5_456 ? O4 C17 1.236(3) . ? O1 C2 1.233(3) . ? O1 Zn1 2.0839(19) 5_456 ? N2 C14 1.286(3) . ? N2 C13 1.332(3) . ? N1 C29 1.315(3) . ? N1 C28 1.331(3) . ? N1 Zn1 2.171(2) 6_657 ? C12 C11 1.320(3) . ? C12 C13 1.371(3) . ? C12 H12 0.9500 . ? C19 C18 1.385(4) . ? C19 C20 1.521(3) . ? C27 C28 1.370(3) . ? C27 C26 1.399(3) . ? C27 H27 0.9500 . ? C4 C3 1.380(4) . ? C4 C5 1.481(3) . ? C5 C6 1.355(4) . ? C5 C10 1.403(4) . ? C26 C30 1.362(3) . ? C26 C23 1.488(3) . ? C28 H28 0.9500 . ? C11 C15 1.447(4) . ? C11 C8 1.474(4) . ? C20 C25 1.347(4) . ? C20 C21 1.368(4) . ? C18 C17 1.404(4) . ? C18 H18 0.9500 . ? C3 C2 1.422(4) . ? C3 H3 0.9500 . ? C2 C1 1.513(4) . ? C13 H13 0.9500 . ? C17 C16 1.536(4) . ? C23 C22 1.368(4) . ? C23 C24 1.400(4) . ? C8 C9 1.344(4) . ? C8 C7 1.383(4) . ? C25 C24 1.378(4) . ? C25 H25 0.9500 . ? C30 C29 1.380(4) . ? C30 H30 0.9500 . ? C24 H24 0.9500 . ? C7 C6 1.369(3) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? C15 C14 1.332(4) . ? C15 H15 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C22 C21 1.385(4) . ? C22 H22 0.9500 . ? C29 H29 0.9500 . ? C21 H21 0.9500 . ? C9 C10 1.357(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C14 H14 0.9500 . ? 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 O2 Zn1 O3 178.98(8) 6_666 . ? O2 Zn1 O1 89.68(7) 6_666 6_666 ? O3 Zn1 O1 90.40(8) . 6_666 ? O2 Zn1 O4 90.66(8) 6_666 . ? O3 Zn1 O4 89.28(7) . . ? O1 Zn1 O4 178.67(8) 6_666 . ? O2 Zn1 N2 88.63(8) 6_666 . ? O3 Zn1 N2 90.35(8) . . ? O1 Zn1 N2 92.36(9) 6_666 . ? O4 Zn1 N2 88.93(8) . . ? O2 Zn1 N1 91.02(8) 6_666 5_567 ? O3 Zn1 N1 90.00(8) . 5_567 ? O1 Zn1 N1 86.79(8) 6_666 5_567 ? O4 Zn1 N1 91.92(8) . 5_567 ? N2 Zn1 N1 179.08(10) . 5_567 ? C19 O3 Zn1 125.55(17) . . ? C4 O2 Zn1 126.53(17) . 5_456 ? C17 O4 Zn1 124.07(19) . . ? C2 O1 Zn1 123.74(19) . 5_456 ? C14 N2 C13 114.6(2) . . ? C14 N2 Zn1 126.4(2) . . ? C13 N2 Zn1 118.82(18) . . ? C29 N1 C28 116.7(2) . . ? C29 N1 Zn1 125.24(19) . 6_657 ? C28 N1 Zn1 118.01(18) . 6_657 ? C11 C12 C13 121.9(3) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? O3 C19 C18 126.8(3) . . ? O3 C19 C20 115.0(3) . . ? C18 C19 C20 118.2(3) . . ? C28 C27 C26 117.4(3) . . ? C28 C27 H27 121.3 . . ? C26 C27 H27 121.3 . . ? O2 C4 C3 124.3(3) . . ? O2 C4 C5 115.7(3) . . ? C3 C4 C5 119.9(3) . . ? C6 C5 C10 115.7(3) . . ? C6 C5 C4 125.5(3) . . ? C10 C5 C4 118.8(3) . . ? C30 C26 C27 117.9(3) . . ? C30 C26 C23 123.2(3) . . ? C27 C26 C23 118.8(3) . . ? N1 C28 C27 124.8(3) . . ? N1 C28 H28 117.6 . . ? C27 C28 H28 117.6 . . ? C12 C11 C15 113.4(3) . . ? C12 C11 C8 124.4(3) . . ? C15 C11 C8 121.6(3) . . ? C25 C20 C21 117.5(3) . . ? C25 C20 C19 118.5(3) . . ? C21 C20 C19 124.0(3) . . ? C19 C18 C17 125.6(3) . . ? C19 C18 H18 117.2 . . ? C17 C18 H18 117.2 . . ? C4 C3 C2 127.5(3) . . ? C4 C3 H3 116.2 . . ? C2 C3 H3 116.2 . . ? O1 C2 C3 125.6(3) . . ? O1 C2 C1 118.8(3) . . ? C3 C2 C1 115.6(3) . . ? N2 C13 C12 123.6(3) . . ? N2 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? O4 C17 C18 126.8(3) . . ? O4 C17 C16 116.1(3) . . ? C18 C17 C16 117.1(3) . . ? C22 C23 C24 118.1(3) . . ? C22 C23 C26 121.9(3) . . ? C24 C23 C26 119.9(3) . . ? C9 C8 C7 115.9(3) . . ? C9 C8 C11 125.0(3) . . ? C7 C8 C11 119.1(3) . . ? C20 C25 C24 123.6(3) . . ? C20 C25 H25 118.2 . . ? C24 C25 H25 118.2 . . ? C26 C30 C29 119.9(3) . . ? C26 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C5 C6 C7 122.7(3) . . ? C5 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C14 C15 C11 119.2(3) . . ? C14 C15 H15 120.4 . . ? C11 C15 H15 120.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? N1 C29 C30 123.1(3) . . ? N1 C29 H29 118.4 . . ? C30 C29 H29 118.4 . . ? C20 C21 C22 121.0(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C8 C9 C10 123.6(3) . . ? C8 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C9 C10 C5 120.5(3) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C14 C15 126.2(3) . . ? N2 C14 H14 116.9 . . ? C15 C14 H14 116.9 . . ? 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 O2 Zn1 O3 C19 77(5) 6_666 . . . ? O1 Zn1 O3 C19 171.2(2) 6_666 . . . ? O4 Zn1 O3 C19 -10.1(2) . . . . ? N2 Zn1 O3 C19 78.8(2) . . . . ? N1 Zn1 O3 C19 -102.0(2) 5_567 . . . ? O2 Zn1 O4 C17 -165.3(2) 6_666 . . . ? O3 Zn1 O4 C17 13.7(2) . . . . ? O1 Zn1 O4 C17 90(4) 6_666 . . . ? N2 Zn1 O4 C17 -76.7(2) . . . . ? N1 Zn1 O4 C17 103.6(2) 5_567 . . . ? O2 Zn1 N2 C14 -136.3(4) 6_666 . . . ? O3 Zn1 N2 C14 43.7(4) . . . . ? O1 Zn1 N2 C14 -46.7(4) 6_666 . . . ? O4 Zn1 N2 C14 133.0(4) . . . . ? N1 Zn1 N2 C14 -68(6) 5_567 . . . ? O2 Zn1 N2 C13 48.7(2) 6_666 . . . ? O3 Zn1 N2 C13 -131.3(2) . . . . ? O1 Zn1 N2 C13 138.3(2) 6_666 . . . ? O4 Zn1 N2 C13 -42.0(2) . . . . ? N1 Zn1 N2 C13 117(6) 5_567 . . . ? Zn1 O3 C19 C18 1.6(4) . . . . ? Zn1 O3 C19 C20 -179.69(17) . . . . ? Zn1 O2 C4 C3 -0.5(4) 5_456 . . . ? Zn1 O2 C4 C5 -178.95(17) 5_456 . . . ? O2 C4 C5 C6 170.2(3) . . . . ? C3 C4 C5 C6 -8.3(5) . . . . ? O2 C4 C5 C10 -12.0(5) . . . . ? C3 C4 C5 C10 169.5(4) . . . . ? C28 C27 C26 C30 -1.8(4) . . . . ? C28 C27 C26 C23 175.2(3) . . . . ? C29 N1 C28 C27 -1.8(5) . . . . ? Zn1 N1 C28 C27 180.0(2) 6_657 . . . ? C26 C27 C28 N1 1.6(5) . . . . ? C13 C12 C11 C15 -8.5(5) . . . . ? C13 C12 C11 C8 179.7(3) . . . . ? O3 C19 C20 C25 8.6(4) . . . . ? C18 C19 C20 C25 -172.6(3) . . . . ? O3 C19 C20 C21 -173.1(3) . . . . ? C18 C19 C20 C21 5.7(5) . . . . ? O3 C19 C18 C17 9.0(6) . . . . ? C20 C19 C18 C17 -169.6(3) . . . . ? O2 C4 C3 C2 8.7(6) . . . . ? C5 C4 C3 C2 -172.9(3) . . . . ? Zn1 O1 C2 C3 -15.7(5) 5_456 . . . ? Zn1 O1 C2 C1 164.6(2) 5_456 . . . ? C4 C3 C2 O1 0.7(6) . . . . ? C4 C3 C2 C1 -179.6(3) . . . . ? C14 N2 C13 C12 6.9(5) . . . . ? Zn1 N2 C13 C12 -177.5(2) . . . . ? C11 C12 C13 N2 0.1(5) . . . . ? Zn1 O4 C17 C18 -9.2(5) . . . . ? Zn1 O4 C17 C16 168.9(2) . . . . ? C19 C18 C17 O4 -4.5(6) . . . . ? C19 C18 C17 C16 177.4(3) . . . . ? C30 C26 C23 C22 148.3(3) . . . . ? C27 C26 C23 C22 -28.6(5) . . . . ? C30 C26 C23 C24 -30.6(5) . . . . ? C27 C26 C23 C24 152.6(3) . . . . ? C12 C11 C8 C9 160.0(4) . . . . ? C15 C11 C8 C9 -11.2(7) . . . . ? C12 C11 C8 C7 -23.6(6) . . . . ? C15 C11 C8 C7 165.2(4) . . . . ? C21 C20 C25 C24 1.9(6) . . . . ? C19 C20 C25 C24 -179.7(3) . . . . ? C27 C26 C30 C29 2.5(5) . . . . ? C23 C26 C30 C29 -174.4(3) . . . . ? C20 C25 C24 C23 0.0(6) . . . . ? C22 C23 C24 C25 -1.2(5) . . . . ? C26 C23 C24 C25 177.7(3) . . . . ? C9 C8 C7 C6 -2.4(6) . . . . ? C11 C8 C7 C6 -179.1(3) . . . . ? C10 C5 C6 C7 1.0(5) . . . . ? C4 C5 C6 C7 178.9(3) . . . . ? C8 C7 C6 C5 -1.9(6) . . . . ? C12 C11 C15 C14 10.3(6) . . . . ? C8 C11 C15 C14 -177.7(4) . . . . ? C24 C23 C22 C21 0.4(5) . . . . ? C26 C23 C22 C21 -178.5(3) . . . . ? C28 N1 C29 C30 2.4(5) . . . . ? Zn1 N1 C29 C30 -179.5(3) 6_657 . . . ? C26 C30 C29 N1 -2.8(6) . . . . ? C25 C20 C21 C22 -2.7(5) . . . . ? C19 C20 C21 C22 179.0(3) . . . . ? C23 C22 C21 C20 1.6(6) . . . . ? C7 C8 C9 C10 7.7(8) . . . . ? C11 C8 C9 C10 -175.8(4) . . . . ? C8 C9 C10 C5 -8.8(8) . . . . ? C6 C5 C10 C9 4.1(7) . . . . ? C4 C5 C10 C9 -174.0(4) . . . . ? C13 N2 C14 C15 -4.8(7) . . . . ? Zn1 N2 C14 C15 180.0(4) . . . . ? C11 C15 C14 N2 -3.8(8) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.013 2535 1088 ' ' 2 0.667 0.333 0.473 199 92 ' ' 3 0.333 0.667 0.527 199 95 ' ' _platon_squeeze_details ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.408 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.049