# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wenlong Liu' _publ_contact_author_email LIUWL@YZU.EDU.CN _publ_section_title ; Hydrothermal syntheses?structures and luminescent properties of d10 metal-organic frameworks based on rigid 3, 3', 5, 5'-azobenzenetetracarboxylic acid ; loop_ _publ_author_name 'Wenlong Liu.' 'Jiaxun Jiang.' 'Xinfang Liu.' 'Chao Yan.' 'Lihua Ye.' ; Li-Min Yuan ; # Attachment 'Crystallographic_data_For_B806360E_.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 685286' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H18 Cd2 N10 O8' _chemical_formula_sum 'C28 H18 Cd2 N10 O8' _chemical_formula_weight 847.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8622(3) _cell_length_b 10.0043(2) _cell_length_c 14.8619(4) _cell_angle_alpha 83.7380(10) _cell_angle_beta 83.711(3) _cell_angle_gamma 80.314(2) _cell_volume 1430.58(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3129 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 21.88 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.780 _exptl_absorpt_correction_T_max 0.828 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 16364 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5603 _reflns_number_gt 4115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0389P)^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 5603 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.19708(3) 0.25144(3) 0.15921(2) 0.036 Uani 1 1 d . . . Cd2 Cd -0.00683(3) -0.00555(3) 0.31547(2) 0.033 Uani 1 1 d . . . C1 C 0.1292(4) 0.3291(4) 0.4121(3) 0.0347(9) Uani 1 1 d . . . C2 C 0.0852(4) 0.4577(4) 0.3680(3) 0.0347(9) Uani 1 1 d . . . H2 H 0.0335 0.4649 0.3185 0.042 Uiso 1 1 calc R . . C3 C 0.1178(4) 0.5735(4) 0.3969(3) 0.0351(9) Uani 1 1 d . . . C4 C 0.1947(4) 0.5618(5) 0.4703(3) 0.0371(9) Uani 1 1 d . . . H4 H 0.2166 0.6399 0.4902 0.045 Uiso 1 1 calc R . . C5 C 0.2405(4) 0.4344(4) 0.5153(3) 0.031 Uani 1 1 d . . . C6 C 0.2060(4) 0.3224(4) 0.4859(3) 0.037 Uani 1 1 d . . . H6 H 0.2348 0.2378 0.5161 0.045 Uiso 1 1 calc R . . C7 C 0.0920(4) 0.2069(4) 0.3787(3) 0.0347(9) Uani 1 1 d . . . C8 C 0.0637(4) 0.7134(4) 0.3520(3) 0.034 Uani 1 1 d . . . C9 C 0.3752(4) -0.4151(4) 0.2270(3) 0.031 Uani 1 1 d . . . C10 C 0.3176(4) -0.2833(4) 0.1941(3) 0.033 Uani 1 1 d . . . H10 H 0.2495 -0.2711 0.1540 0.040 Uiso 1 1 calc R . . C11 C 0.3634(4) -0.1688(4) 0.2220(3) 0.0321(9) Uani 1 1 d . . . C12 C 0.4631(4) -0.1895(4) 0.2832(2) 0.0333(9) Uani 1 1 d . . . H12 H 0.4938 -0.1149 0.3018 0.040 Uiso 1 1 calc R . . C13 C 0.5171(4) -0.3183(4) 0.3168(3) 0.034 Uani 1 1 d . . . C14 C 0.4749(4) -0.4325(4) 0.2888(3) 0.0348(9) Uani 1 1 d . . . H14 H 0.5130 -0.5196 0.3112 0.042 Uiso 1 1 calc R . . C15 C 0.3219(4) -0.5366(5) 0.2018(3) 0.037 Uani 1 1 d . . . C16 C 0.2973(4) -0.0262(4) 0.1899(3) 0.0364(9) Uani 1 1 d . . . C17 C 0.3018(4) 0.2446(4) -0.0789(3) 0.0367(9) Uani 1 1 d . . . H17 H 0.3969 0.2173 -0.0805 0.044 Uiso 1 1 calc R . . C18 C 0.2278(4) 0.2682(4) -0.1528(3) 0.030 Uani 1 1 d . . . H18 H 0.2637 0.2598 -0.2128 0.036 Uiso 1 1 calc R . . C19 C 0.0889(4) 0.3048(4) -0.0311(3) 0.0330(9) Uani 1 1 d . . . C20 C -0.0326(4) 0.3400(4) 0.0291(3) 0.0316(9) Uani 1 1 d . . . C21 C -0.2413(4) 0.4074(4) 0.0916(2) 0.0313(9) Uani 1 1 d . . . H21 H -0.3353 0.4405 0.0994 0.038 Uiso 1 1 calc R . . C22 C -0.1534(4) 0.3652(4) 0.1592(3) 0.0360(9) Uani 1 1 d . . . H22 H -0.1779 0.3637 0.2215 0.043 Uiso 1 1 calc R . . C23 C -0.1305(4) 0.0383(4) 0.1038(3) 0.034 Uani 1 1 d . . . H23 H -0.0482 0.0197 0.0670 0.040 Uiso 1 1 calc R . . C24 C -0.2561(5) 0.0683(4) 0.0729(3) 0.0391(10) Uani 1 1 d . . . H24 H -0.2761 0.0727 0.0128 0.047 Uiso 1 1 calc R . . C25 C -0.2727(4) 0.0747(4) 0.2193(3) 0.0328(9) Uani 1 1 d . . . C26 C -0.3174(4) 0.0989(4) 0.3130(3) 0.0358(9) Uani 1 1 d . . . C27 C -0.4322(4) 0.1597(4) 0.4391(3) 0.0378(10) Uani 1 1 d . . . H27 H -0.5016 0.1944 0.4818 0.045 Uiso 1 1 calc R . . C28 C -0.3055(4) 0.1009(4) 0.4561(3) 0.0333(9) Uani 1 1 d . . . H28 H -0.2717 0.0880 0.5130 0.040 Uiso 1 1 calc R . . N1 N 0.3203(3) 0.4373(3) 0.5929(2) 0.0311(7) Uani 1 1 d . . . N2 N 0.3848(3) 0.3234(4) 0.6152(2) 0.0367(8) Uani 1 1 d . . . N3 N -0.0214(3) 0.3254(3) 0.1171(2) 0.0341(8) Uani 1 1 d . . . N4 N 0.2144(3) 0.2672(3) -0.0020(2) 0.0364(8) Uani 1 1 d . . . N5 N -0.1618(3) 0.3907(3) 0.0108(2) 0.0354(8) Uani 1 1 d . . . H5 H -0.1902 0.4097 -0.0425 0.042 Uiso 1 1 calc R . . N6 N 0.0926(4) 0.3061(3) -0.1239(2) 0.0372(8) Uani 1 1 d . . . H6A H 0.0241 0.3265 -0.1567 0.045 Uiso 1 1 calc R . . N7 N -0.2311(3) 0.0618(4) 0.3761(2) 0.0364(8) Uani 1 1 d . . . N8 N -0.1390(3) 0.0385(3) 0.1949(2) 0.0315(7) Uani 1 1 d . . . N9 N -0.4436(3) 0.1605(3) 0.3478(2) 0.0346(8) Uani 1 1 d . . . H9 H -0.5146 0.1928 0.3188 0.042 Uiso 1 1 calc R . . N10 N -0.3509(4) 0.0914(3) 0.1489(2) 0.0359(8) Uani 1 1 d . . . H10A H -0.4394 0.1118 0.1503 0.043 Uiso 1 1 calc R . . O1 O 0.0679(3) 0.2098(3) 0.29625(18) 0.0346(6) Uani 1 1 d . . . O2 O 0.0861(3) 0.1014(3) 0.43219(18) 0.0382(7) Uani 1 1 d . . . O3 O -0.0128(3) 0.7232(3) 0.29095(17) 0.0348(6) Uani 1 1 d . . . O4 O 0.1107(3) 0.8104(3) 0.37850(19) 0.0380(7) Uani 1 1 d . . . O5 O 0.3757(3) -0.6531(3) 0.22936(18) 0.0375(6) Uani 1 1 d . . . O6 O 0.2208(3) -0.5151(3) 0.15362(17) 0.0320(6) Uani 1 1 d . . . O7 O 0.3669(3) 0.0682(3) 0.1853(2) 0.0417(7) Uani 1 1 d . . . O8 O 0.1782(3) -0.0088(3) 0.17107(18) 0.0349(6) 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 Cd1 0.037 0.037 0.035 -0.001 -0.006 -0.004 Cd2 0.035 0.029 0.034 -0.001 -0.010 -0.003 C1 0.032(2) 0.031(2) 0.040(2) -0.0099(18) 0.0015(17) -0.0014(17) C2 0.037(2) 0.031(2) 0.035(2) 0.0029(17) -0.0100(18) -0.0040(18) C3 0.0242(19) 0.037(2) 0.041(2) 0.0082(19) -0.0001(17) -0.0052(17) C4 0.034(2) 0.045(3) 0.033(2) -0.0158(19) -0.0017(17) -0.0005(19) C5 0.030 0.031 0.036 -0.011 -0.006 -0.005 C6 0.046 0.032 0.030 0.005 -0.009 0.004 C7 0.034(2) 0.031(2) 0.036(2) 0.0005(18) -0.0090(17) 0.0040(17) C8 0.032 0.032 0.034 0.003 0.006 -0.004 C9 0.034 0.026 0.033 -0.007 0.006 -0.003 C10 0.030 0.034 0.035 0.003 -0.008 -0.007 C11 0.035(2) 0.032(2) 0.031(2) -0.0061(17) 0.0034(16) -0.0096(17) C12 0.031(2) 0.046(2) 0.026(2) -0.0148(18) 0.0049(16) -0.0115(18) C13 0.033 0.035 0.033 0.000 -0.006 -0.005 C14 0.030(2) 0.042(2) 0.032(2) -0.0070(18) 0.0000(17) -0.0036(18) C15 0.038 0.046 0.032 -0.017 0.004 -0.015 C16 0.035(2) 0.041(2) 0.034(2) -0.0040(18) -0.0016(17) -0.0070(19) C17 0.036(2) 0.026(2) 0.044(2) -0.0049(18) 0.0026(18) 0.0042(17) C18 0.031 0.024 0.034 0.001 0.004 -0.013 C19 0.030(2) 0.032(2) 0.036(2) 0.0019(17) -0.0010(17) -0.0045(17) C20 0.029(2) 0.034(2) 0.032(2) -0.0017(17) -0.0086(16) -0.0019(17) C21 0.030(2) 0.031(2) 0.029(2) 0.0067(16) 0.0001(16) -0.0007(17) C22 0.037(2) 0.034(2) 0.036(2) -0.0026(18) 0.0018(18) -0.0081(18) C23 0.029 0.038 0.035 -0.007 -0.002 -0.010 C24 0.055(3) 0.031(2) 0.034(2) -0.0089(18) -0.0056(19) -0.0061(19) C25 0.032(2) 0.034(2) 0.028(2) 0.0028(17) -0.0008(16) 0.0021(17) C26 0.037(2) 0.039(2) 0.030(2) 0.0012(18) 0.0041(18) -0.0094(18) C27 0.033(2) 0.037(2) 0.037(2) -0.0122(18) 0.0125(18) 0.0080(18) C28 0.038(2) 0.032(2) 0.027(2) -0.0033(17) -0.0028(17) 0.0026(18) N1 0.0275(16) 0.0283(17) 0.0379(18) -0.0082(14) -0.0070(14) -0.0001(14) N2 0.0333(18) 0.041(2) 0.0372(19) -0.0157(16) -0.0115(15) 0.0028(16) N3 0.0424(19) 0.0279(18) 0.0303(18) -0.0039(14) -0.0045(15) 0.0007(15) N4 0.0391(19) 0.0323(19) 0.0348(19) -0.0016(15) -0.0010(15) -0.0001(15) N5 0.0364(19) 0.0301(18) 0.0383(19) 0.0009(15) -0.0047(15) -0.0034(15) N6 0.043(2) 0.037(2) 0.0350(19) -0.0044(15) -0.0069(15) -0.0130(16) N7 0.0379(18) 0.0349(19) 0.0336(19) 0.0020(15) -0.0046(15) -0.0001(15) N8 0.0365(18) 0.0345(19) 0.0237(17) -0.0008(14) 0.0008(14) -0.0100(15) N9 0.0326(18) 0.0309(18) 0.038(2) -0.0111(15) -0.0003(15) 0.0048(14) N10 0.0399(19) 0.0347(19) 0.0354(19) -0.0093(15) -0.0065(15) -0.0063(15) O1 0.0298(14) 0.0384(16) 0.0382(16) -0.0024(13) -0.0043(12) -0.0123(12) O2 0.0481(17) 0.0388(18) 0.0314(15) 0.0017(13) -0.0178(13) -0.0113(14) O3 0.0418(16) 0.0339(15) 0.0286(14) 0.0087(12) -0.0173(12) -0.0038(12) O4 0.0411(16) 0.0349(16) 0.0382(16) -0.0074(13) -0.0133(13) 0.0022(13) O5 0.0429(16) 0.0323(16) 0.0360(15) -0.0003(12) -0.0099(13) -0.0002(13) O6 0.0384(15) 0.0281(14) 0.0349(15) -0.0050(11) -0.0124(12) -0.0133(12) O7 0.0349(15) 0.0356(16) 0.0547(19) 0.0046(14) -0.0069(13) -0.0098(13) O8 0.0338(15) 0.0362(16) 0.0329(15) 0.0014(12) -0.0018(12) -0.0041(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 Cd1 N3 2.289(3) . ? Cd1 O7 2.296(3) . ? Cd1 O1 2.317(3) . ? Cd1 N4 2.372(3) . ? Cd1 O6 2.378(3) 1_565 ? Cd1 O5 2.508(3) 1_565 ? Cd1 O8 2.627(3) . ? Cd2 O4 2.181(3) 1_545 ? Cd2 N8 2.292(3) . ? Cd2 N7 2.314(3) . ? Cd2 O1 2.371(3) . ? Cd2 O2 2.465(3) . ? C1 C6 1.388(6) . ? C1 C2 1.401(5) . ? C1 C7 1.483(6) . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(6) . ? C3 C8 1.521(5) . ? C4 C5 1.401(6) . ? C4 H4 0.9300 . ? C5 C6 1.353(6) . ? C5 N1 1.472(5) . ? C6 H6 0.9300 . ? C7 O2 1.255(5) . ? C7 O1 1.270(5) . ? C8 O3 1.228(5) . ? C8 O4 1.259(5) . ? C9 C14 1.395(5) . ? C9 C10 1.403(5) . ? C9 C15 1.501(6) . ? C10 C11 1.416(6) . ? C10 H10 0.9300 . ? C11 C12 1.387(6) . ? C11 C16 1.515(6) . ? C12 C13 1.371(6) . ? C12 H12 0.9300 . ? C13 C14 1.398(6) . ? C13 N2 1.464(5) 2_656 ? C14 H14 0.9300 . ? C15 O5 1.242(5) . ? C15 O6 1.266(5) . ? C16 O8 1.216(5) . ? C16 O7 1.249(5) . ? C17 C18 1.362(6) . ? C17 N4 1.370(5) . ? C17 H17 0.9300 . ? C18 N6 1.358(5) . ? C18 H18 0.9300 . ? C19 N4 1.337(5) . ? C19 N6 1.374(5) . ? C19 C20 1.433(5) . ? C20 N3 1.315(5) . ? C20 N5 1.335(5) . ? C21 N5 1.370(5) . ? C21 C22 1.383(6) . ? C21 H21 0.9300 . ? C22 N3 1.395(5) . ? C22 H22 0.9300 . ? C23 C24 1.343(6) . ? C23 N8 1.348(5) . ? C23 H23 0.9300 . ? C24 N10 1.398(5) . ? C24 H24 0.9300 . ? C25 N8 1.328(5) . ? C25 N10 1.347(5) . ? C25 C26 1.448(5) . ? C26 N7 1.316(5) . ? C26 N9 1.366(5) . ? C27 C28 1.327(5) . ? C27 N9 1.373(5) . ? C27 H27 0.9300 . ? C28 N7 1.385(5) . ? C28 H28 0.9300 . ? N1 N2 1.238(4) . ? N2 C13 1.464(5) 2_656 ? N5 H5 0.8600 . ? N6 H6A 0.8600 . ? N9 H9 0.8600 . ? N10 H10A 0.8600 . ? O4 Cd2 2.181(3) 1_565 ? O5 Cd1 2.508(3) 1_545 ? O6 Cd1 2.378(3) 1_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cd1 O7 146.53(11) . . ? N3 Cd1 O1 79.63(10) . . ? O7 Cd1 O1 94.42(10) . . ? N3 Cd1 N4 73.30(11) . . ? O7 Cd1 N4 99.35(11) . . ? O1 Cd1 N4 148.58(11) . . ? N3 Cd1 O6 86.89(10) . 1_565 ? O7 Cd1 O6 126.24(10) . 1_565 ? O1 Cd1 O6 104.41(9) . 1_565 ? N4 Cd1 O6 89.94(10) . 1_565 ? N3 Cd1 O5 137.27(10) . 1_565 ? O7 Cd1 O5 75.66(10) . 1_565 ? O1 Cd1 O5 94.29(9) . 1_565 ? N4 Cd1 O5 116.40(11) . 1_565 ? O6 Cd1 O5 53.41(8) 1_565 1_565 ? N3 Cd1 O8 95.27(10) . . ? O7 Cd1 O8 51.74(9) . . ? O1 Cd1 O8 74.77(9) . . ? N4 Cd1 O8 91.92(10) . . ? O6 Cd1 O8 177.48(8) 1_565 . ? O5 Cd1 O8 124.14(9) 1_565 . ? O4 Cd2 N8 133.94(11) 1_545 . ? O4 Cd2 N7 118.00(11) 1_545 . ? N8 Cd2 N7 73.88(11) . . ? O4 Cd2 O1 123.75(10) 1_545 . ? N8 Cd2 O1 94.82(10) . . ? N7 Cd2 O1 98.62(11) . . ? O4 Cd2 O2 82.33(10) 1_545 . ? N8 Cd2 O2 143.70(10) . . ? N7 Cd2 O2 91.37(11) . . ? O1 Cd2 O2 54.00(9) . . ? C6 C1 C2 118.0(4) . . ? C6 C1 C7 122.9(4) . . ? C2 C1 C7 119.1(4) . . ? C3 C2 C1 120.8(4) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.2(4) . . ? C2 C3 C8 120.7(4) . . ? C4 C3 C8 120.1(4) . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 118.4(4) . . ? C6 C5 N1 126.3(4) . . ? C4 C5 N1 115.3(3) . . ? C5 C6 C1 122.5(4) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? O2 C7 O1 120.9(4) . . ? O2 C7 C1 119.5(4) . . ? O1 C7 C1 119.6(4) . . ? O3 C8 O4 125.5(4) . . ? O3 C8 C3 119.6(4) . . ? O4 C8 C3 114.8(4) . . ? C14 C9 C10 119.8(4) . . ? C14 C9 C15 119.8(4) . . ? C10 C9 C15 120.2(4) . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 118.9(4) . . ? C12 C11 C16 120.8(4) . . ? C10 C11 C16 120.1(4) . . ? C13 C12 C11 121.1(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.7(4) . . ? C12 C13 N2 114.7(4) . 2_656 ? C14 C13 N2 124.6(4) . 2_656 ? C9 C14 C13 119.6(4) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O5 C15 O6 122.5(4) . . ? O5 C15 C9 119.8(4) . . ? O6 C15 C9 117.7(4) . . ? O8 C16 O7 123.2(4) . . ? O8 C16 C11 118.3(4) . . ? O7 C16 C11 118.5(4) . . ? C18 C17 N4 109.4(4) . . ? C18 C17 H17 125.3 . . ? N4 C17 H17 125.3 . . ? N6 C18 C17 108.4(3) . . ? N6 C18 H18 125.8 . . ? C17 C18 H18 125.8 . . ? N4 C19 N6 111.9(3) . . ? N4 C19 C20 122.7(4) . . ? N6 C19 C20 125.4(4) . . ? N3 C20 N5 111.3(3) . . ? N3 C20 C19 118.5(3) . . ? N5 C20 C19 130.2(4) . . ? N5 C21 C22 106.1(3) . . ? N5 C21 H21 126.9 . . ? C22 C21 H21 126.9 . . ? C21 C22 N3 107.7(3) . . ? C21 C22 H22 126.1 . . ? N3 C22 H22 126.1 . . ? C24 C23 N8 111.2(4) . . ? C24 C23 H23 124.4 . . ? N8 C23 H23 124.4 . . ? C23 C24 N10 106.5(4) . . ? C23 C24 H24 126.7 . . ? N10 C24 H24 126.7 . . ? N8 C25 N10 113.0(3) . . ? N8 C25 C26 119.3(4) . . ? N10 C25 C26 127.6(4) . . ? N7 C26 N9 112.1(3) . . ? N7 C26 C25 120.1(4) . . ? N9 C26 C25 127.8(4) . . ? C28 C27 N9 108.4(3) . . ? C28 C27 H27 125.8 . . ? N9 C27 H27 125.8 . . ? C27 C28 N7 109.5(3) . . ? C27 C28 H28 125.2 . . ? N7 C28 H28 125.2 . . ? N2 N1 C5 111.5(3) . . ? N1 N2 C13 116.0(3) . 2_656 ? C20 N3 C22 106.6(3) . . ? C20 N3 Cd1 115.6(3) . . ? C22 N3 Cd1 137.9(3) . . ? C19 N4 C17 105.1(3) . . ? C19 N4 Cd1 109.8(2) . . ? C17 N4 Cd1 144.9(3) . . ? C20 N5 C21 108.2(3) . . ? C20 N5 H5 125.9 . . ? C21 N5 H5 125.9 . . ? C18 N6 C19 105.2(3) . . ? C18 N6 H6A 127.4 . . ? C19 N6 H6A 127.4 . . ? C26 N7 C28 105.1(3) . . ? C26 N7 Cd2 112.5(3) . . ? C28 N7 Cd2 141.1(3) . . ? C25 N8 C23 104.6(3) . . ? C25 N8 Cd2 113.3(2) . . ? C23 N8 Cd2 142.0(3) . . ? C26 N9 C27 104.9(3) . . ? C26 N9 H9 127.6 . . ? C27 N9 H9 127.6 . . ? C25 N10 C24 104.5(3) . . ? C25 N10 H10A 127.8 . . ? C24 N10 H10A 127.8 . . ? C7 O1 Cd1 133.2(2) . . ? C7 O1 Cd2 94.3(2) . . ? Cd1 O1 Cd2 114.02(11) . . ? C7 O2 Cd2 90.3(2) . . ? C8 O4 Cd2 105.1(2) . 1_565 ? C15 O5 Cd1 89.3(2) . 1_545 ? C15 O6 Cd1 94.7(2) . 1_545 ? C16 O7 Cd1 99.7(3) . . ? C16 O8 Cd1 84.8(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.571 _refine_diff_density_min -0.900 _refine_diff_density_rms 0.091 # Attachment '2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 685287' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C20 H11 Cd N3 O4), H4 O2, H4 O2' _chemical_formula_sum 'C80 H52 Cd4 N12 O20' _chemical_formula_weight 1950.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.9618(17) _cell_length_b 13.7136(11) _cell_length_c 16.205(2) _cell_angle_alpha 90.00 _cell_angle_beta 128.8420(10) _cell_angle_gamma 90.00 _cell_volume 3801.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9648 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.61 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 1.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7803 _exptl_absorpt_correction_T_max 0.8707 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 13675 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3393 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0588P)^2^+12.3989P] 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 3393 _refine_ls_number_parameters 265 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.108949(14) -0.052021(18) 0.394661(18) 0.02946(13) Uani 1 1 d . . . C1 C 0.3233(2) -0.1074(3) 0.6982(3) 0.0310(8) Uani 1 1 d . . . C2 C 0.3601(2) -0.1955(3) 0.7097(3) 0.0307(7) Uani 1 1 d . . . H2 H 0.3354 -0.2398 0.6539 0.037 Uiso 1 1 calc R . . C3 C 0.4337(2) -0.2171(2) 0.8046(3) 0.0286(7) Uani 1 1 d . . . C4 C 0.4731(2) -0.1490(2) 0.8867(3) 0.0286(7) Uani 1 1 d . . . H4 H 0.5239 -0.1610 0.9478 0.034 Uiso 1 1 calc R . . C5 C 0.4351(2) -0.0625(2) 0.8757(3) 0.0292(8) Uani 1 1 d . . . C6 C 0.3606(2) -0.0423(2) 0.7828(3) 0.0316(8) Uani 1 1 d . . . H6 H 0.3354 0.0149 0.7771 0.038 Uiso 1 1 calc R . . C7 C 0.2450(2) -0.0843(3) 0.5948(3) 0.0349(8) Uani 1 1 d U . . C8 C 0.4713(2) -0.3142(3) 0.8187(3) 0.0310(8) Uani 1 1 d . . . C9 C -0.0130(2) 0.0816(3) 0.3947(3) 0.040 Uani 1 1 d . . . H9 H -0.0309 0.0215 0.3983 0.047 Uiso 1 1 calc R . . C10 C -0.0477(3) 0.1668(3) 0.3973(3) 0.0464(10) Uani 1 1 d . . . H10 H -0.0873 0.1629 0.4029 0.056 Uiso 1 1 calc R . . C11 C -0.0222(3) 0.2543(3) 0.3916(3) 0.0478(10) Uani 1 1 d . . . H11 H -0.0452 0.3114 0.3912 0.057 Uiso 1 1 calc R . . C12 C 0.0398(3) 0.2590(3) 0.3861(3) 0.0399(9) Uani 1 1 d . . . C13 C 0.0699(3) 0.3498(3) 0.3813(4) 0.0535(12) Uani 1 1 d . . . H13 H 0.0492 0.4082 0.3830 0.064 Uiso 1 1 calc R . . C14 C 0.1274(3) 0.3511(3) 0.3746(4) 0.0529(12) Uani 1 1 d . . . H14 H 0.1467 0.4108 0.3728 0.063 Uiso 1 1 calc R . . C15 C 0.1603(3) 0.2627(3) 0.3701(3) 0.0445(10) Uani 1 1 d . . . C16 C 0.2190(3) 0.2613(4) 0.3595(4) 0.0558(12) Uani 1 1 d . . . H16 H 0.2386 0.3196 0.3554 0.067 Uiso 1 1 calc R . . C17 C 0.2472(3) 0.1745(4) 0.3551(4) 0.0582(13) Uani 1 1 d . . . H17 H 0.2858 0.1729 0.3475 0.070 Uiso 1 1 calc R . . C18 C 0.2174(3) 0.0886(4) 0.3623(4) 0.0497(10) Uani 1 1 d . . . H18 H 0.2375 0.0298 0.3603 0.060 Uiso 1 1 calc R . . C19 C 0.1322(2) 0.1723(3) 0.3752(3) 0.0353(8) Uani 1 1 d . . . C20 C 0.0709(2) 0.1705(3) 0.3837(3) 0.0320(8) Uani 1 1 d . . . N1 N 0.46870(19) 0.0107(2) 0.9574(2) 0.0363(7) Uani 1 1 d . . . N2 N 0.04392(18) 0.0831(2) 0.3874(2) 0.0311(6) Uani 1 1 d . . . N3 N 0.16147(19) 0.0858(2) 0.3719(2) 0.0368(7) Uani 1 1 d . . . O1 O 0.22553(16) -0.1276(2) 0.5124(2) 0.050 Uani 1 1 d U . . O2 O 0.20132(18) -0.0233(3) 0.5911(2) 0.059 Uani 1 1 d U . . O3 O 0.54399(16) -0.3202(2) 0.8898(2) 0.0455(7) Uani 1 1 d . . . O4 O 0.42759(16) -0.38451(18) 0.7615(2) 0.0381(6) Uani 1 1 d . . . O1W O 0.1919(4) 0.1115(4) 0.7107(5) 0.0474(15) Uani 0.50 1 d PD . . H1A H 0.153(3) 0.118(8) 0.6462(19) 0.057 Uiso 0.50 1 d PD . . H1B H 0.174(4) 0.101(7) 0.743(5) 0.057 Uiso 0.50 1 d PD . . O2W O 0.1716(4) 0.6897(8) 0.5932(8) 0.093(3) Uani 0.50 1 d PD . . H2A H 0.212(5) 0.676(10) 0.656(3) 0.111 Uiso 0.50 1 d PD . . H2B H 0.177(8) 0.658(10) 0.553(7) 0.111 Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02563(18) 0.02395(18) 0.02372(18) -0.00146(9) 0.00818(14) -0.00010(9) C1 0.0274(17) 0.0271(18) 0.0244(17) -0.0002(14) 0.0095(15) 0.0007(14) C2 0.0304(17) 0.0261(17) 0.0228(16) -0.0037(14) 0.0104(15) -0.0031(14) C3 0.0284(17) 0.0240(17) 0.0246(16) -0.0012(14) 0.0124(14) 0.0011(14) C4 0.0285(17) 0.0242(17) 0.0202(16) 0.0001(13) 0.0089(14) 0.0022(14) C5 0.0311(19) 0.0238(17) 0.0215(17) -0.0017(13) 0.0111(15) -0.0019(13) C6 0.0327(19) 0.0243(18) 0.0284(19) 0.0009(14) 0.0145(17) 0.0048(14) C7 0.0273(18) 0.0290(18) 0.0296(19) 0.0009(15) 0.0088(16) 0.0012(15) C8 0.0361(19) 0.0284(18) 0.0221(16) 0.0000(14) 0.0152(15) 0.0046(15) C9 0.039 0.041 0.032 0.000 0.019 0.000 C10 0.046(2) 0.057(3) 0.036(2) -0.002(2) 0.0258(19) 0.006(2) C11 0.056(3) 0.043(2) 0.038(2) -0.0009(19) 0.027(2) 0.014(2) C12 0.049(2) 0.032(2) 0.0296(19) -0.0001(16) 0.0204(18) 0.0055(17) C13 0.075(3) 0.025(2) 0.052(3) 0.0006(19) 0.035(3) 0.001(2) C14 0.071(3) 0.029(2) 0.048(3) 0.0004(19) 0.032(2) -0.009(2) C15 0.047(2) 0.041(2) 0.033(2) -0.0018(18) 0.0188(18) -0.0125(19) C16 0.055(3) 0.059(3) 0.048(3) 0.000(2) 0.030(2) -0.019(2) C17 0.050(3) 0.079(4) 0.054(3) -0.005(3) 0.037(2) -0.014(3) C18 0.044(2) 0.057(3) 0.049(3) -0.007(2) 0.029(2) -0.001(2) C19 0.039(2) 0.034(2) 0.0246(17) -0.0021(15) 0.0159(16) -0.0041(16) C20 0.0339(19) 0.0292(19) 0.0222(17) -0.0003(14) 0.0124(15) 0.0007(15) N1 0.0375(16) 0.0265(16) 0.0250(14) -0.0055(13) 0.0100(12) 0.0023(13) N2 0.0308(15) 0.0292(15) 0.0259(15) -0.0009(13) 0.0141(13) 0.0002(13) N3 0.0346(16) 0.0367(17) 0.0309(16) -0.0037(14) 0.0167(14) -0.0025(14) O1 0.037 0.047 0.027 -0.008 0.001 0.011 O2 0.041 0.069 0.035 -0.002 0.008 0.028 O3 0.0340(15) 0.0408(16) 0.0389(15) -0.0051(13) 0.0119(13) 0.0108(12) O4 0.0465(15) 0.0252(13) 0.0348(14) -0.0060(11) 0.0217(13) -0.0005(11) O1W 0.066(4) 0.036(3) 0.084(4) -0.029(3) 0.068(4) -0.023(3) O2W 0.041(4) 0.116(8) 0.083(6) 0.044(6) 0.021(4) -0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O3 2.230(3) 8_445 ? Cd1 O1 2.268(3) . ? Cd1 O4 2.293(3) 7_546 ? Cd1 N2 2.296(3) . ? Cd1 N3 2.360(3) . ? Cd1 O2 2.510(3) . ? Cd1 C7 2.736(4) . ? C1 C6 1.394(5) . ? C1 C2 1.398(5) . ? C1 C7 1.500(5) . ? C2 C3 1.396(5) . ? C2 H2 0.9300 . ? C3 C4 1.396(5) . ? C3 C8 1.506(5) . ? C4 C5 1.397(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(5) . ? C5 N1 1.441(4) . ? C6 H6 0.9300 . ? C7 O2 1.245(5) . ? C7 O1 1.267(5) . ? C8 O3 1.256(5) . ? C8 O4 1.263(4) . ? C9 N2 1.329(5) . ? C9 C10 1.409(6) . ? C9 H9 0.9300 . ? C10 C11 1.353(7) . ? C10 H10 0.9300 . ? C11 C12 1.421(6) . ? C11 H11 0.9300 . ? C12 C20 1.405(5) . ? C12 C13 1.434(6) . ? C13 C14 1.333(8) . ? C13 H13 0.9300 . ? C14 C15 1.435(7) . ? C14 H14 0.9300 . ? C15 C16 1.403(7) . ? C15 C19 1.410(5) . ? C16 C17 1.365(8) . ? C16 H16 0.9300 . ? C17 C18 1.388(7) . ? C17 H17 0.9300 . ? C18 N3 1.332(5) . ? C18 H18 0.9300 . ? C19 N3 1.366(5) . ? C19 C20 1.438(6) . ? C20 N2 1.354(5) . ? N1 N1 1.225(6) 5_657 ? O3 Cd1 2.230(3) 8_546 ? O4 Cd1 2.293(3) 7_546 ? O1W H1A 0.842(10) . ? O1W H1B 0.837(10) . ? O2W H2A 0.844(10) . ? O2W H2B 0.850(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cd1 O1 91.73(11) 8_445 . ? O3 Cd1 O4 83.66(11) 8_445 7_546 ? O1 Cd1 O4 100.58(10) . 7_546 ? O3 Cd1 N2 105.57(12) 8_445 . ? O1 Cd1 N2 138.57(10) . . ? O4 Cd1 N2 118.26(10) 7_546 . ? O3 Cd1 N3 171.23(10) 8_445 . ? O1 Cd1 N3 95.33(12) . . ? O4 Cd1 N3 89.92(10) 7_546 . ? N2 Cd1 N3 72.26(12) . . ? O3 Cd1 O2 99.10(12) 8_445 . ? O1 Cd1 O2 54.34(10) . . ? O4 Cd1 O2 154.68(10) 7_546 . ? N2 Cd1 O2 85.46(10) . . ? N3 Cd1 O2 89.26(12) . . ? O3 Cd1 C7 96.51(11) 8_445 . ? O1 Cd1 C7 27.34(11) . . ? O4 Cd1 C7 127.81(11) 7_546 . ? N2 Cd1 C7 111.89(11) . . ? N3 Cd1 C7 92.15(11) . . ? O2 Cd1 C7 27.00(11) . . ? C6 C1 C2 119.3(3) . . ? C6 C1 C7 121.1(3) . . ? C2 C1 C7 119.6(3) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 C8 119.5(3) . . ? C2 C3 C8 120.0(3) . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 N1 115.7(3) . . ? C4 C5 N1 123.5(3) . . ? C5 C6 C1 120.3(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 O1 121.6(3) . . ? O2 C7 C1 120.4(3) . . ? O1 C7 C1 118.0(3) . . ? O2 C7 Cd1 66.3(2) . . ? O1 C7 Cd1 55.27(18) . . ? C1 C7 Cd1 172.9(3) . . ? O3 C8 O4 124.5(3) . . ? O3 C8 C3 117.3(3) . . ? O4 C8 C3 118.1(3) . . ? N2 C9 C10 123.2(4) . . ? N2 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C11 C10 C9 118.5(4) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 C12 120.0(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C20 C12 C11 117.6(4) . . ? C20 C12 C13 120.0(4) . . ? C11 C12 C13 122.4(4) . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 121.6(4) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C19 117.6(4) . . ? C16 C15 C14 123.2(4) . . ? C19 C15 C14 119.2(4) . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 118.9(4) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N3 C18 C17 123.5(5) . . ? N3 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? N3 C19 C15 121.9(4) . . ? N3 C19 C20 118.7(3) . . ? C15 C19 C20 119.4(4) . . ? N2 C20 C12 122.1(4) . . ? N2 C20 C19 118.8(3) . . ? C12 C20 C19 119.2(3) . . ? N1 N1 C5 115.9(4) 5_657 . ? C9 N2 C20 118.6(3) . . ? C9 N2 Cd1 125.0(3) . . ? C20 N2 Cd1 116.2(2) . . ? C18 N3 C19 118.0(4) . . ? C18 N3 Cd1 128.2(3) . . ? C19 N3 Cd1 113.7(3) . . ? C7 O1 Cd1 97.4(2) . . ? C7 O2 Cd1 86.7(2) . . ? C8 O3 Cd1 120.1(2) . 8_546 ? C8 O4 Cd1 132.8(2) . 7_546 ? H1A O1W H1B 106.8(18) . . ? H2A O2W H2B 105.5(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1B O4 0.837(10) 2.20(5) 2.930(6) 146(7) 4_556 O2W H2A O1W 0.844(10) 2.05(4) 2.878(10) 165(12) 4_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.830 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.110 # Attachment '3.cif' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 685288' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C20 H11 N3 O4 Zn), H4 O2' _chemical_formula_sum 'C80 H48 N12 O18 Zn4' _chemical_formula_weight 1726.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.9780(3) _cell_length_b 13.1721(2) _cell_length_c 16.6474(4) _cell_angle_alpha 90.00 _cell_angle_beta 129.015(2) _cell_angle_gamma 90.00 _cell_volume 3574.17(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6558 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.13 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6769 _exptl_absorpt_correction_T_max 0.7338 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 22249 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3515 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0700P)^2^+1.2200P] 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 3515 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.1375(2) 0.6571(3) 0.6978(3) 0.0390(8) Uani 1 1 d . . . C2 C 0.1099(3) 0.5641(3) 0.7029(3) 0.0458(10) Uani 1 1 d . . . H2 H 0.0811 0.5214 0.6456 0.055 Uiso 1 1 calc R . . C3 C 0.1251(2) 0.5340(3) 0.7942(3) 0.0406(9) Uani 1 1 d . . . C4 C 0.1673(2) 0.5974(3) 0.8802(3) 0.0412(9) Uani 1 1 d . . . H4 H 0.1752 0.5790 0.9398 0.049 Uiso 1 1 calc R . . C5 C 0.1977(2) 0.6894(3) 0.8749(3) 0.0427(9) Uani 1 1 d . . . C6 C 0.1833(3) 0.7198(3) 0.7858(3) 0.0463(10) Uani 1 1 d . . . H6 H 0.2037 0.7815 0.7837 0.056 Uiso 1 1 calc R . . C7 C 0.1210(2) 0.6918(3) 0.5997(3) 0.041 Uani 1 1 d . . . C8 C 0.0959(2) 0.4319(3) 0.8005(3) 0.0368(8) Uani 1 1 d . . . C9 C 0.1617(2) 0.8175(3) 0.3867(3) 0.0422(9) Uani 1 1 d . . . H9 H 0.1823 0.7545 0.3879 0.051 Uiso 1 1 calc R . . C10 C 0.2011(2) 0.9059(3) 0.3898(3) 0.0454(9) Uani 1 1 d . . . H10 H 0.2475 0.9012 0.3944 0.054 Uiso 1 1 calc R . . C11 C 0.1699(2) 0.9995(3) 0.3860(3) 0.0427(9) Uani 1 1 d . . . H11 H 0.1942 1.0585 0.3861 0.051 Uiso 1 1 calc R . . C12 C 0.1007(2) 1.0050(3) 0.3820(3) 0.0435(9) Uani 1 1 d . . . C13 C 0.0645(2) 1.0998(3) 0.3784(3) 0.0425(9) Uani 1 1 d . . . H13 H 0.0870 1.1608 0.3788 0.051 Uiso 1 1 calc R . . C14 C -0.0019(2) 1.1006(3) 0.3745(3) 0.0405(9) Uani 1 1 d . . . H14 H -0.0240 1.1625 0.3727 0.049 Uiso 1 1 calc R . . C15 C -0.0390(2) 1.0086(3) 0.3729(3) 0.0386(8) Uani 1 1 d . . . C16 C -0.1090(2) 1.0058(3) 0.3679(3) 0.0382(8) Uani 1 1 d . . . H16 H -0.1333 1.0658 0.3658 0.046 Uiso 1 1 calc R . . C17 C -0.1399(2) 0.9152(3) 0.3661(3) 0.0385(8) Uani 1 1 d . . . H17 H -0.1859 0.9123 0.3627 0.046 Uiso 1 1 calc R . . C18 C -0.1022(2) 0.8251(3) 0.3696(3) 0.0371(8) Uani 1 1 d . . . H18 H -0.1246 0.7635 0.3678 0.045 Uiso 1 1 calc R . . C19 C -0.0052(2) 0.9152(3) 0.3766(3) 0.0379(8) Uani 1 1 d . . . C20 C 0.0658(2) 0.9132(3) 0.3809(3) 0.0388(8) Uani 1 1 d . . . N1 N 0.2487(2) 0.7574(3) 0.9623(2) 0.0385(7) Uani 1 1 d . . . N2 N -0.0360(2) 0.8236(2) 0.3753(3) 0.0423(8) Uani 1 1 d . . . N3 N 0.0960(2) 0.8209(3) 0.3821(3) 0.0424(8) Uani 1 1 d . . . O1 O 0.06529(16) 0.6405(2) 0.5178(2) 0.0416(6) Uani 1 1 d . . . O2 O 0.15667(16) 0.7641(2) 0.5999(2) 0.0447(7) Uani 1 1 d . . . O3 O 0.06871(16) 0.3706(2) 0.7270(2) 0.0427(6) Uani 1 1 d . . . O4 O 0.10022(17) 0.4152(2) 0.8783(2) 0.0459(7) Uani 1 1 d . . . O1W O 0.0866(4) 0.5992(5) 1.0059(5) 0.0524(15) Uani 0.50 1 d P . . H1A H 0.100(7) 0.540(9) 1.001(8) 0.063 Uiso 0.50 1 d P . . H1B H 0.038(7) 0.612(8) 0.953(9) 0.063 Uiso 0.50 1 d P . . Zn1 Zn 0.03716(3) 0.69732(3) 0.38886(3) 0.037 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 0.039(2) 0.0268(18) 0.035(2) 0.0063(15) 0.0158(17) 0.0074(15) C2 0.056(3) 0.030(2) 0.026(2) -0.0081(15) 0.0142(19) -0.0056(17) C3 0.0309(18) 0.041(2) 0.035(2) 0.0016(16) 0.0134(16) -0.0021(15) C4 0.037(2) 0.037(2) 0.031(2) -0.0004(16) 0.0124(17) 0.0001(15) C5 0.0287(17) 0.038(2) 0.035(2) -0.0023(17) 0.0079(16) 0.0026(16) C6 0.043(2) 0.044(2) 0.034(2) 0.0000(17) 0.0157(18) -0.0100(17) C7 0.048 0.035 0.032 0.007 0.022 0.014 C8 0.042(2) 0.0312(19) 0.0281(19) -0.0009(15) 0.0181(17) -0.0084(15) C9 0.040(2) 0.040(2) 0.031(2) -0.0051(16) 0.0151(17) 0.0086(16) C10 0.036(2) 0.045(2) 0.032(2) -0.0037(17) 0.0106(17) 0.0010(17) C11 0.040(2) 0.034(2) 0.035(2) -0.0048(16) 0.0143(17) -0.0079(16) C12 0.037(2) 0.036(2) 0.032(2) -0.0012(16) 0.0095(17) -0.0029(16) C13 0.036(2) 0.039(2) 0.036(2) -0.0027(16) 0.0140(18) -0.0062(16) C14 0.0334(18) 0.036(2) 0.036(2) 0.0013(16) 0.0141(17) 0.0026(15) C15 0.0297(17) 0.035(2) 0.031(2) -0.0014(15) 0.0095(16) -0.0015(15) C16 0.0297(17) 0.039(2) 0.034(2) -0.0010(16) 0.0145(16) 0.0001(15) C17 0.0373(19) 0.048(2) 0.0294(19) -0.0012(16) 0.0207(17) -0.0078(16) C18 0.045(2) 0.035(2) 0.033(2) -0.0070(15) 0.0249(18) -0.0179(16) C19 0.0299(17) 0.036(2) 0.030(2) 0.0018(15) 0.0104(16) -0.0023(15) C20 0.0312(18) 0.039(2) 0.031(2) -0.0068(16) 0.0119(16) -0.0048(15) N1 0.0373(16) 0.0481(19) 0.0294(17) -0.0012(14) 0.0207(14) -0.0078(14) N2 0.0372(16) 0.0349(18) 0.0340(18) -0.0047(14) 0.0124(15) -0.0118(13) N3 0.0381(17) 0.0337(17) 0.0351(18) -0.0006(14) 0.0133(15) 0.0022(13) O1 0.0371(14) 0.0326(14) 0.0320(14) 0.0001(11) 0.0107(12) -0.0055(11) O2 0.0333(13) 0.0426(16) 0.0362(16) 0.0024(12) 0.0113(12) -0.0083(11) O3 0.0359(14) 0.0414(15) 0.0306(14) -0.0100(12) 0.0112(12) -0.0178(12) O4 0.0471(16) 0.0453(16) 0.0270(14) -0.0051(12) 0.0145(12) -0.0143(13) O1W 0.041(3) 0.045(4) 0.050(4) -0.018(3) 0.019(3) -0.014(3) Zn1 0.039 0.033 0.032 -0.002 0.020 -0.003 _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 1.381(6) . ? C1 C6 1.407(6) . ? C1 C7 1.512(6) . ? C2 C3 1.398(6) . ? C2 H2 0.9300 . ? C3 C4 1.392(6) . ? C3 C8 1.509(5) . ? C4 C5 1.398(6) . ? C4 H4 0.9300 . ? C5 C6 1.373(6) . ? C5 N1 1.450(5) . ? C6 H6 0.9300 . ? C7 O2 1.209(5) . ? C7 O1 1.294(5) . ? C8 O4 1.260(5) . ? C8 O3 1.263(5) . ? C9 N3 1.332(6) . ? C9 C10 1.410(6) . ? C9 H9 0.9300 . ? C10 C11 1.378(6) . ? C10 H10 0.9300 . ? C11 C12 1.412(6) . ? C11 H11 0.9300 . ? C12 C20 1.407(6) . ? C12 C13 1.442(6) . ? C13 C14 1.352(6) . ? C13 H13 0.9300 . ? C14 C15 1.432(5) . ? C14 H14 0.9300 . ? C15 C19 1.403(5) . ? C15 C16 1.416(6) . ? C16 C17 1.351(6) . ? C16 H16 0.9300 . ? C17 C18 1.407(6) . ? C17 H17 0.9300 . ? C18 N2 1.330(5) . ? C18 H18 0.9300 . ? C19 N2 1.363(5) . ? C19 C20 1.446(6) . ? C20 N3 1.364(5) . ? N1 N1 1.236(6) 7_567 ? N2 Zn1 2.177(4) . ? N3 Zn1 2.089(4) . ? O1 Zn1 1.980(3) . ? O3 Zn1 2.015(2) 5_566 ? O4 Zn1 2.066(3) 6_566 ? O1W H1A 0.85(11) . ? O1W H1B 0.85(11) . ? Zn1 O3 2.015(2) 5_566 ? Zn1 O4 2.066(3) 6_565 ? 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 C6 119.6(4) . . ? C2 C1 C7 121.0(4) . . ? C6 C1 C7 119.3(4) . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.7(4) . . ? C4 C3 C8 119.1(4) . . ? C2 C3 C8 120.2(4) . . ? C3 C4 C5 118.4(4) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 121.5(4) . . ? C6 C5 N1 115.2(4) . . ? C4 C5 N1 123.3(4) . . ? C5 C6 C1 119.7(4) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 124.1(4) . . ? O2 C7 C1 120.9(4) . . ? O1 C7 C1 114.9(4) . . ? O4 C8 O3 125.5(3) . . ? O4 C8 C3 117.3(3) . . ? O3 C8 C3 117.2(3) . . ? N3 C9 C10 122.3(4) . . ? N3 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C11 C10 C9 119.1(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C20 C12 C11 117.7(4) . . ? C20 C12 C13 119.3(4) . . ? C11 C12 C13 123.0(4) . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.8(4) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C19 C15 C16 117.2(3) . . ? C19 C15 C14 119.1(4) . . ? C16 C15 C14 123.7(4) . . ? C17 C16 C15 119.4(4) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 119.5(4) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? N2 C18 C17 123.5(3) . . ? N2 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? N2 C19 C15 123.6(4) . . ? N2 C19 C20 116.7(3) . . ? C15 C19 C20 119.7(3) . . ? N3 C20 C12 122.3(4) . . ? N3 C20 C19 118.1(3) . . ? C12 C20 C19 119.7(4) . . ? N1 N1 C5 117.1(4) 7_567 . ? C18 N2 C19 116.8(3) . . ? C18 N2 Zn1 130.9(3) . . ? C19 N2 Zn1 112.2(3) . . ? C9 N3 C20 119.0(4) . . ? C9 N3 Zn1 126.5(3) . . ? C20 N3 Zn1 114.3(3) . . ? C7 O1 Zn1 113.6(2) . . ? C8 O3 Zn1 139.9(3) . 5_566 ? C8 O4 Zn1 125.3(2) . 6_566 ? H1A O1W H1B 109(10) . . ? O1 Zn1 O3 105.46(11) . 5_566 ? O1 Zn1 O4 92.95(11) . 6_565 ? O3 Zn1 O4 88.79(12) 5_566 6_565 ? O1 Zn1 N3 124.73(12) . . ? O3 Zn1 N3 128.87(13) 5_566 . ? O4 Zn1 N3 97.06(13) 6_565 . ? O1 Zn1 N2 96.34(12) . . ? O3 Zn1 N2 87.69(12) 5_566 . ? O4 Zn1 N2 170.65(13) 6_565 . ? N3 Zn1 N2 78.51(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.620 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.074 # Attachment '4.cif' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 685289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 N6 O10 Zn3' _chemical_formula_sum 'C36 H28 N6 O10 Zn3' _chemical_formula_weight 900.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.264(4) _cell_length_b 5.8069(7) _cell_length_c 21.163(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.1500(10) _cell_angle_gamma 90.00 _cell_volume 3444.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5618 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 27.24 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 2.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5411 _exptl_absorpt_correction_T_max 0.6238 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 12743 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3364 _reflns_number_gt 2680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0600P)^2^+1.9900P] 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 3364 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Zn1 Zn 0.0000 0.08886(11) 0.2500 0.03555(18) Uani 1 2 d S . . Zn2 Zn 0.233718(15) 0.82219(7) 0.69744(2) 0.03546(15) Uani 1 1 d . . . O1 O 0.00926(9) 0.2885(4) 0.32807(14) 0.0386(6) Uani 1 1 d . . . O2 O 0.07216(10) 0.0804(5) 0.39019(14) 0.0403(6) Uani 1 1 d . . . O3 O 0.16706(9) 0.7596(5) 0.64094(13) 0.0373(6) Uani 1 1 d . . . O4 O 0.18536(10) 0.4176(5) 0.60877(14) 0.0437(7) Uani 1 1 d . . . O5 O 0.26058(9) 0.6467(4) 0.77988(14) 0.0393(6) Uani 1 1 d . . . H5 H 0.2777 0.7195 0.8142 0.047 Uiso 1 1 d R . . N1 N -0.00347(12) 0.9300(6) 0.47561(17) 0.0400(8) Uani 1 1 d . . . N2 N 0.05305(11) -0.1183(6) 0.24584(17) 0.036 Uani 1 1 d . . . N3 N 0.27162(10) 0.7764(5) 0.63557(15) 0.030 Uani 1 1 d . . . C1 C 0.05462(13) 0.4198(7) 0.43980(19) 0.0355(8) Uani 1 1 d . . . C2 C 0.09773(14) 0.4068(7) 0.4961(2) 0.0365(8) Uani 1 1 d . . . H2 H 0.1186 0.2849 0.5005 0.044 Uiso 1 1 calc R . . C3 C 0.10894(14) 0.5787(7) 0.5454(2) 0.0400(9) Uani 1 1 d . . . C4 C 0.07672(13) 0.7543(7) 0.54007(19) 0.0364(8) Uani 1 1 d . . . H4 H 0.0844 0.8695 0.5730 0.044 Uiso 1 1 calc R . . C5 C 0.03310(13) 0.7590(7) 0.4859(2) 0.0378(9) Uani 1 1 d . . . C6 C 0.02230(13) 0.5913(6) 0.43486(19) 0.0352(8) Uani 1 1 d . . . H6 H -0.0066 0.5960 0.3978 0.042 Uiso 1 1 calc R . . C7 C 0.04491(13) 0.2457(7) 0.3822(2) 0.0372(9) Uani 1 1 d . . . C8 C 0.15785(13) 0.5818(7) 0.60322(19) 0.035 Uani 1 1 d . . . C9 C 0.07683(15) -0.0665(7) 0.2059(2) 0.0455(10) Uani 1 1 d . . . H9 H 0.0696 0.0703 0.1812 0.055 Uiso 1 1 calc R . . C10 C 0.11218(14) -0.2094(8) 0.1996(2) 0.0428(10) Uani 1 1 d . . . H10 H 0.1286 -0.1683 0.1719 0.051 Uiso 1 1 calc R . . C11 C 0.12184(14) -0.4117(7) 0.2354(2) 0.0436(10) Uani 1 1 d . . . H11 H 0.1445 -0.5127 0.2313 0.052 Uiso 1 1 calc R . . C12 C 0.09802(15) -0.4654(7) 0.2775(2) 0.0439(10) Uani 1 1 d . . . H12 H 0.1047 -0.6005 0.3030 0.053 Uiso 1 1 calc R . . C13 C 0.06395(15) -0.3137(7) 0.2807(2) 0.045 Uani 1 1 d . . . H13 H 0.0477 -0.3503 0.3090 0.054 Uiso 1 1 calc R . . C14 C 0.27370(15) 0.9354(7) 0.5922(2) 0.040 Uani 1 1 d . . . H14 H 0.2559 1.0693 0.5876 0.047 Uiso 1 1 calc R . . C15 C 0.30196(16) 0.9102(8) 0.5528(2) 0.0505(11) Uani 1 1 d . . . H15 H 0.3029 1.0250 0.5227 0.061 Uiso 1 1 calc R . . C16 C 0.32790(15) 0.7132(7) 0.5599(2) 0.0476(10) Uani 1 1 d . . . H16 H 0.3474 0.6938 0.5352 0.057 Uiso 1 1 calc R . . C17 C 0.32533(15) 0.5448(8) 0.6032(2) 0.0452(10) Uani 1 1 d . . . H17 H 0.3424 0.4084 0.6077 0.054 Uiso 1 1 calc R . . C18 C 0.29647(14) 0.5814(7) 0.6408(2) 0.0388(9) Uani 1 1 d . . . H18 H 0.2945 0.4666 0.6703 0.047 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 0.0353(3) 0.0309(3) 0.0363(3) 0.000 0.0087(3) 0.000 Zn2 0.0297(2) 0.0295(2) 0.0391(3) -0.00143(18) 0.00375(18) -0.00029(18) O1 0.0358(14) 0.0307(14) 0.0427(15) -0.0117(11) 0.0075(12) -0.0040(11) O2 0.0410(15) 0.0444(16) 0.0390(15) -0.0022(12) 0.0191(12) -0.0002(13) O3 0.0314(13) 0.0415(15) 0.0288(13) -0.0114(11) -0.0002(10) -0.0033(11) O4 0.0376(14) 0.0443(16) 0.0354(14) 0.0054(12) -0.0019(11) 0.0140(13) O5 0.0331(13) 0.0289(14) 0.0407(14) 0.0005(11) -0.0034(11) -0.0008(11) N1 0.0381(18) 0.0313(17) 0.0432(18) -0.0042(13) 0.0068(15) 0.0092(14) N2 0.028 0.034 0.047 -0.001 0.014 -0.001 N3 0.032 0.030 0.032 -0.003 0.014 -0.002 C1 0.0341(19) 0.0328(19) 0.0353(19) -0.0008(16) 0.0082(16) -0.0026(16) C2 0.0331(19) 0.0325(19) 0.041(2) 0.0006(16) 0.0102(16) 0.0011(15) C3 0.0308(19) 0.034(2) 0.044(2) 0.0026(17) 0.0010(16) -0.0025(16) C4 0.0339(19) 0.035(2) 0.035(2) -0.0066(16) 0.0066(15) 0.0020(16) C5 0.035(2) 0.032(2) 0.041(2) -0.0010(16) 0.0085(16) 0.0057(16) C6 0.0295(18) 0.0309(19) 0.0376(19) 0.0006(16) 0.0038(15) 0.0003(15) C7 0.0314(19) 0.035(2) 0.045(2) -0.0028(17) 0.0141(17) -0.0046(16) C8 0.028 0.036 0.037 0.005 0.007 0.001 C9 0.042(2) 0.035(2) 0.045(2) 0.0061(18) -0.0001(18) 0.0025(18) C10 0.039(2) 0.053(3) 0.043(2) 0.0016(19) 0.0230(18) -0.0110(19) C11 0.034(2) 0.038(2) 0.046(2) -0.0090(18) 0.0010(17) 0.0097(17) C12 0.044(2) 0.026(2) 0.048(2) 0.0019(17) 0.0022(19) 0.0093(17) C13 0.041 0.052 0.044 0.002 0.020 -0.014 C14 0.041 0.039 0.040 0.003 0.016 0.000 C15 0.046(2) 0.050(3) 0.052(3) 0.010(2) 0.0146(19) -0.014(2) C16 0.046(2) 0.043(3) 0.052(3) -0.010(2) 0.0162(19) -0.0100(19) C17 0.044(2) 0.049(3) 0.042(2) -0.0092(19) 0.0146(18) 0.0035(19) C18 0.038(2) 0.035(2) 0.050(2) 0.0016(17) 0.0253(18) -0.0012(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 Zn1 O1 1.950(3) . ? Zn1 O1 1.950(3) 2 ? Zn1 N2 2.035(3) 2 ? Zn1 N2 2.035(3) . ? Zn2 O5 1.917(3) . ? Zn2 O5 1.936(3) 4_556 ? Zn2 O3 1.953(2) . ? Zn2 N3 2.058(3) . ? O1 C7 1.267(5) . ? O2 C7 1.235(5) . ? O3 C8 1.270(5) . ? O4 C8 1.242(5) . ? O5 Zn2 1.936(3) 4_546 ? O5 H5 0.8311 . ? N1 N1 1.268(6) 5_576 ? N1 C5 1.441(5) . ? N2 C13 1.326(5) . ? N2 C9 1.335(6) . ? N3 C14 1.319(5) . ? N3 C18 1.341(5) . ? C1 C6 1.372(6) . ? C1 C2 1.398(5) . ? C1 C7 1.525(6) . ? C2 C3 1.390(6) . ? C2 H2 0.9300 . ? C3 C4 1.386(6) . ? C3 C8 1.524(5) . ? C4 C5 1.385(5) . ? C4 H4 0.9300 . ? C5 C6 1.398(5) . ? C6 H6 0.9300 . ? C9 C10 1.400(6) . ? C9 H9 0.9300 . ? C10 C11 1.369(6) . ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.378(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.410(6) . ? C14 H14 0.9300 . ? C15 C16 1.363(7) . ? C15 H15 0.9300 . ? C16 C17 1.362(6) . ? C16 H16 0.9300 . ? C17 C18 1.402(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 Zn1 O1 107.04(17) . 2 ? O1 Zn1 N2 100.29(12) . 2 ? O1 Zn1 N2 121.64(12) 2 2 ? O1 Zn1 N2 121.64(12) . . ? O1 Zn1 N2 100.28(12) 2 . ? N2 Zn1 N2 107.50(18) 2 . ? O5 Zn2 O5 108.93(6) . 4_556 ? O5 Zn2 O3 116.37(12) . . ? O5 Zn2 O3 107.93(11) 4_556 . ? O5 Zn2 N3 111.32(12) . . ? O5 Zn2 N3 105.34(12) 4_556 . ? O3 Zn2 N3 106.34(12) . . ? C7 O1 Zn1 116.8(2) . . ? C8 O3 Zn2 117.9(2) . . ? Zn2 O5 Zn2 135.29(15) . 4_546 ? Zn2 O5 H5 115.8 . . ? Zn2 O5 H5 108.1 4_546 . ? N1 N1 C5 115.9(4) 5_576 . ? C13 N2 C9 117.8(4) . . ? C13 N2 Zn1 121.1(3) . . ? C9 N2 Zn1 121.1(3) . . ? C14 N3 C18 118.4(3) . . ? C14 N3 Zn2 122.4(3) . . ? C18 N3 Zn2 119.1(3) . . ? C6 C1 C2 120.9(4) . . ? C6 C1 C7 120.2(3) . . ? C2 C1 C7 118.8(3) . . ? C3 C2 C1 119.1(4) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 C8 119.8(3) . . ? C2 C3 C8 120.0(4) . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 N1 125.2(3) . . ? C6 C5 N1 114.9(3) . . ? C1 C6 C5 119.6(3) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O2 C7 O1 125.0(4) . . ? O2 C7 C1 119.2(3) . . ? O1 C7 C1 115.7(3) . . ? O4 C8 O3 125.8(3) . . ? O4 C8 C3 118.7(3) . . ? O3 C8 C3 115.5(3) . . ? N2 C9 C10 122.7(4) . . ? N2 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 117.9(4) . . ? C11 C10 H10 121.1 . . ? C9 C10 H10 121.1 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.2(4) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? N2 C13 C12 123.6(4) . . ? N2 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? N3 C14 C15 122.5(4) . . ? N3 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C16 C15 C14 118.3(4) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 118.6(4) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N3 C18 C17 122.1(4) . . ? N3 C18 H18 118.9 . . ? C17 C18 H18 118.9 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.420 _refine_diff_density_min -0.915 _refine_diff_density_rms 0.082