# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 909598' #TrackingRef '123-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H53 N14 O18.50 Zn3' _chemical_formula_weight 1318.24 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4581(4) _cell_length_b 11.6819(4) _cell_length_c 11.8696(6) _cell_angle_alpha 64.132(4) _cell_angle_beta 81.202(4) _cell_angle_gamma 72.663(3) _cell_volume 1364.15(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4716 _cell_measurement_theta_min 3.0670 _cell_measurement_theta_max 29.0339 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.395 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.87529 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details CRYSALISPRO _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8976 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4793 _reflns_number_gt 4201 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSALISPRO _computing_cell_refinement CRYSALISPRO _computing_data_reduction CRYSALISPRO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+7.4998P] 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 4793 _refine_ls_number_parameters 397 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.060 _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 1.0000 0.5000 0.0135(2) Uani 1 2 d S . . Zn2 Zn 0.0000 0.5000 0.5000 0.0141(2) Uani 1 2 d S . . Zn3 Zn 0.0000 1.0000 0.0000 0.0208(2) Uani 1 2 d S . . O1 O -0.0836(3) 0.8451(3) 0.5504(3) 0.0184(7) Uani 1 1 d . . . O2 O -0.0437(3) 0.6328(3) 0.5885(3) 0.0202(8) Uani 1 1 d . . . O3 O -0.0436(3) 1.0778(3) 0.3117(3) 0.0211(8) Uani 1 1 d . . . O4 O -0.0521(4) 1.1043(3) 0.1165(3) 0.0250(8) Uani 1 1 d . . . N1 N 0.0032(3) 0.6760(4) 0.3495(4) 0.0156(8) Uani 1 1 d . . . N6 N 0.1732(3) 0.8758(4) 0.4749(4) 0.0161(8) Uani 1 1 d . . . N4 N -0.2004(4) 0.5441(4) 0.4828(4) 0.0194(9) Uani 1 1 d . . . N2 N 0.0234(4) 0.7171(4) 0.2265(4) 0.0182(9) Uani 1 1 d . . . C19 C 0.2492(4) 0.9194(5) 0.3777(5) 0.0189(10) Uani 1 1 d . . . H19 H 0.2202 1.0007 0.3120 0.023 Uiso 1 1 calc R . . C2 C -0.0233(4) 0.7795(5) 0.3805(5) 0.0153(10) Uani 1 1 d . . . N3 N 0.0093(4) 0.8463(4) 0.1775(4) 0.0197(9) Uani 1 1 d . . . C4 C -0.0396(4) 1.0332(5) 0.2334(4) 0.0167(10) Uani 1 1 d . . . C7 C -0.4533(4) 0.6563(5) 0.4725(5) 0.0177(10) Uani 1 1 d . . . C16 C 0.3343(4) 0.6804(5) 0.5670(5) 0.0205(11) Uani 1 1 d . . . H16 H 0.3599 0.5981 0.6326 0.025 Uiso 1 1 calc R . . C18 C 0.3687(4) 0.8494(5) 0.3702(5) 0.0186(10) Uani 1 1 d . . . H18 H 0.4181 0.8829 0.3004 0.022 Uiso 1 1 calc R . . C9 C -0.2558(4) 0.6158(5) 0.3734(5) 0.0229(11) Uani 1 1 d . . . H9 H -0.2084 0.6278 0.3002 0.027 Uiso 1 1 calc R . . N5 N 0.1887(4) 0.9986(4) 0.0102(4) 0.0245(10) Uani 1 1 d . . . C1 C -0.0515(4) 0.7524(5) 0.5161(4) 0.0135(10) Uani 1 1 d . . . C3 C -0.0196(4) 0.8887(5) 0.2702(4) 0.0157(10) Uani 1 1 d . . . C17 C 0.4146(4) 0.7276(5) 0.4686(5) 0.0170(10) Uani 1 1 d . . . C15 C 0.2160(4) 0.7567(5) 0.5669(5) 0.0202(11) Uani 1 1 d . . . H15 H 0.1636 0.7238 0.6338 0.024 Uiso 1 1 calc R . . C8 C -0.3812(5) 0.6736(5) 0.3634(5) 0.0236(11) Uani 1 1 d . . . H8 H -0.4163 0.7229 0.2852 0.028 Uiso 1 1 calc R . . C6 C -0.3963(4) 0.5761(5) 0.5861(5) 0.0220(11) Uani 1 1 d . . . H6 H -0.4417 0.5581 0.6609 0.026 Uiso 1 1 calc R . . C5 C -0.2709(5) 0.5231(5) 0.5868(5) 0.0217(11) Uani 1 1 d . . . H5 H -0.2338 0.4702 0.6637 0.026 Uiso 1 1 calc R . . C12 C 0.4344(5) 0.9994(5) 0.0033(5) 0.0231(11) Uani 1 1 d . . . C11 C 0.4008(5) 0.8848(6) 0.0316(6) 0.0305(13) Uani 1 1 d . . . H11 H 0.4604 0.8056 0.0486 0.037 Uiso 1 1 calc R . . C14 C 0.2205(5) 1.1087(6) -0.0152(6) 0.0317(13) Uani 1 1 d . . . H14 H 0.1589 1.1863 -0.0316 0.038 Uiso 1 1 calc R . . C13 C 0.3391(5) 1.1134(6) -0.0183(6) 0.0314(13) Uani 1 1 d . . . H13 H 0.3561 1.1923 -0.0347 0.038 Uiso 1 1 calc R . . C10 C 0.2797(6) 0.8883(6) 0.0345(6) 0.0311(13) Uani 1 1 d . . . H10 H 0.2596 0.8100 0.0543 0.037 Uiso 1 1 calc R . . O11 O 0.6300(8) 0.5684(6) 0.1458(5) 0.090(2) Uani 1 1 d . . . C22 C 0.4934(7) 0.9526(8) 0.5618(8) 0.0555(19) Uani 1 1 d U . . N7 N 0.4533(8) 0.7656(9) 0.8098(9) 0.087(2) Uani 1 1 d U . . C21 C 0.5819(10) 0.8551(10) 0.6415(11) 0.079(3) Uani 1 1 d U . . H21 H 0.6626 0.8475 0.6119 0.094 Uiso 1 1 calc R . . C23 C 0.3789(10) 0.9555(12) 0.6194(11) 0.088(3) Uani 1 1 d U . . H23 H 0.3116 1.0220 0.5781 0.105 Uiso 1 1 calc R . . C20 C 0.5632(12) 0.7746(13) 0.7518(13) 0.098(3) Uani 1 1 d U . . H20 H 0.6319 0.7160 0.7973 0.117 Uiso 1 1 calc R . . C24 C 0.3627(12) 0.8594(13) 0.7393(12) 0.099(3) Uani 1 1 d U . . H24 H 0.2833 0.8616 0.7716 0.118 Uiso 1 1 calc R . . O10 O 0.3969(14) 0.5861(10) 0.0614(13) 0.186(5) Uani 1 1 d . . . O5 O 0.9114(17) 0.5015(13) 0.1747(12) 0.098(5) Uani 0.50 1 d P . . O7 O 0.9149(18) 0.3655(9) 0.0639(15) 0.259(10) Uani 1 1 d . . . O6 O 0.1757(16) 0.5353(18) 0.1190(17) 0.110(5) Uani 0.50 1 d PU . . O8 O 0.1378(14) 0.2684(16) 0.1859(15) 0.153(5) Uani 0.75 1 d PU . . O9 O 0.1068(17) 0.4059(19) 0.1701(18) 0.117(6) Uani 0.50 1 d PU . . 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 0.0110(4) 0.0103(4) 0.0176(4) -0.0058(3) -0.0016(3) 0.0001(3) Zn2 0.0113(4) 0.0077(4) 0.0197(4) -0.0024(3) 0.0009(3) -0.0029(3) Zn3 0.0315(5) 0.0202(5) 0.0113(4) -0.0017(3) -0.0014(3) -0.0146(4) O1 0.0175(17) 0.0156(17) 0.0236(18) -0.0094(15) 0.0040(14) -0.0065(14) O2 0.0251(19) 0.0146(18) 0.0176(18) -0.0031(15) 0.0013(14) -0.0069(14) O3 0.0291(19) 0.0135(17) 0.0197(18) -0.0065(15) -0.0050(15) -0.0025(15) O4 0.042(2) 0.0150(18) 0.0159(18) -0.0016(15) -0.0038(16) -0.0107(16) N1 0.015(2) 0.013(2) 0.017(2) -0.0050(17) 0.0017(16) -0.0047(16) N6 0.0134(19) 0.013(2) 0.020(2) -0.0066(17) -0.0012(16) -0.0021(16) N4 0.013(2) 0.016(2) 0.027(2) -0.0084(19) 0.0006(17) -0.0038(17) N2 0.020(2) 0.016(2) 0.018(2) -0.0054(17) 0.0028(17) -0.0089(17) C19 0.020(2) 0.015(2) 0.020(3) -0.006(2) -0.004(2) -0.003(2) C2 0.010(2) 0.014(2) 0.020(3) -0.005(2) -0.0005(18) -0.0045(18) N3 0.024(2) 0.015(2) 0.020(2) -0.0054(18) -0.0006(17) -0.0087(18) C4 0.017(2) 0.012(2) 0.017(2) -0.002(2) -0.0007(19) -0.0047(19) C7 0.013(2) 0.014(2) 0.028(3) -0.011(2) 0.001(2) -0.0033(19) C16 0.014(2) 0.013(2) 0.031(3) -0.006(2) 0.000(2) -0.0027(19) C18 0.016(2) 0.021(3) 0.019(3) -0.008(2) 0.0011(19) -0.006(2) C9 0.015(2) 0.028(3) 0.023(3) -0.010(2) 0.004(2) -0.005(2) N5 0.035(3) 0.023(2) 0.019(2) -0.0051(19) -0.0017(19) -0.019(2) C1 0.009(2) 0.014(2) 0.014(2) -0.0032(19) -0.0015(17) -0.0024(18) C3 0.014(2) 0.016(2) 0.015(2) -0.004(2) -0.0013(18) -0.0058(19) C17 0.013(2) 0.015(2) 0.026(3) -0.011(2) -0.0010(19) -0.0026(19) C15 0.012(2) 0.015(2) 0.031(3) -0.008(2) 0.004(2) -0.0044(19) C8 0.018(3) 0.025(3) 0.024(3) -0.008(2) -0.002(2) -0.003(2) C6 0.017(2) 0.023(3) 0.023(3) -0.009(2) 0.004(2) -0.004(2) C5 0.018(2) 0.020(3) 0.022(3) -0.005(2) 0.000(2) -0.003(2) C12 0.034(3) 0.026(3) 0.013(2) -0.007(2) 0.000(2) -0.015(2) C11 0.035(3) 0.028(3) 0.033(3) -0.013(3) -0.005(3) -0.012(3) C14 0.034(3) 0.023(3) 0.038(3) -0.008(3) -0.002(3) -0.013(2) C13 0.036(3) 0.026(3) 0.035(3) -0.009(3) 0.004(3) -0.019(3) C10 0.042(3) 0.021(3) 0.034(3) -0.010(2) -0.004(3) -0.015(3) O11 0.189(8) 0.040(3) 0.044(3) -0.015(3) -0.006(4) -0.034(4) C22 0.049(3) 0.059(4) 0.082(4) -0.046(3) -0.007(3) -0.018(3) N7 0.073(4) 0.097(4) 0.107(5) -0.056(4) -0.001(3) -0.022(3) C21 0.082(5) 0.059(4) 0.105(5) -0.042(4) -0.018(4) -0.012(3) C23 0.079(5) 0.106(5) 0.087(5) -0.057(4) 0.001(4) -0.011(4) C20 0.093(5) 0.092(5) 0.120(6) -0.054(4) 0.010(4) -0.032(4) C24 0.089(5) 0.117(6) 0.094(5) -0.049(4) -0.007(4) -0.023(4) O10 0.256(15) 0.076(6) 0.202(13) -0.055(8) -0.015(11) -0.008(8) O5 0.183(16) 0.056(8) 0.051(8) -0.021(6) -0.011(9) -0.021(9) O7 0.45(3) 0.049(5) 0.268(17) 0.011(8) -0.179(17) -0.089(10) O6 0.111(6) 0.111(6) 0.110(6) -0.046(3) -0.003(2) -0.029(2) O8 0.154(6) 0.153(6) 0.153(6) -0.063(3) -0.004(2) -0.042(2) O9 0.118(6) 0.117(6) 0.117(6) -0.049(2) -0.0029(11) -0.0303(18) _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 O3 2.090(3) 2_576 ? Zn1 O3 2.090(3) . ? Zn1 O1 2.112(3) 2_576 ? Zn1 O1 2.112(3) . ? Zn1 N6 2.148(4) 2_576 ? Zn1 N6 2.148(4) . ? Zn2 N1 2.059(4) 2_566 ? Zn2 N1 2.059(4) . ? Zn2 O2 2.136(3) 2_566 ? Zn2 O2 2.136(3) . ? Zn2 N4 2.219(4) . ? Zn2 N4 2.219(4) 2_566 ? Zn3 N3 2.081(4) . ? Zn3 N3 2.081(4) 2_575 ? Zn3 O4 2.130(4) 2_575 ? Zn3 O4 2.130(4) . ? Zn3 N5 2.178(4) . ? Zn3 N5 2.179(4) 2_575 ? O1 C1 1.255(6) . ? O2 C1 1.265(6) . ? O3 C4 1.237(6) . ? O4 C4 1.273(6) . ? N1 N2 1.329(6) . ? N1 C2 1.351(6) . ? N6 C19 1.339(7) . ? N6 C15 1.342(6) . ? N4 C9 1.333(7) . ? N4 C5 1.337(7) . ? N2 N3 1.327(6) . ? C19 C18 1.382(7) . ? C19 H19 0.9300 . ? C2 C3 1.379(7) . ? C2 C1 1.501(7) . ? N3 C3 1.354(6) . ? C4 C3 1.500(7) . ? C7 C6 1.387(7) . ? C7 C8 1.395(7) . ? C7 C17 1.491(6) 1_455 ? C16 C15 1.382(7) . ? C16 C17 1.388(7) . ? C16 H16 0.9300 . ? C18 C17 1.399(7) . ? C18 H18 0.9300 . ? C9 C8 1.393(7) . ? C9 H9 0.9300 . ? N5 C14 1.336(7) . ? N5 C10 1.341(8) . ? C17 C7 1.491(6) 1_655 ? C15 H15 0.9300 . ? C8 H8 0.9300 . ? C6 C5 1.384(7) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C12 C11 1.389(8) . ? C12 C13 1.398(8) . ? C12 C12 1.497(11) 2_675 ? C11 C10 1.372(8) . ? C11 H11 0.9300 . ? C14 C13 1.370(8) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C10 H10 0.9300 . ? C22 C21 1.373(12) . ? C22 C23 1.382(13) . ? C22 C22 1.420(17) 2_676 ? N7 C24 1.328(14) . ? N7 C20 1.350(14) . ? C21 C20 1.267(15) . ? C21 H21 0.9300 . ? C23 C24 1.403(16) . ? C23 H23 0.9300 . ? C20 H20 0.9300 . ? C24 H24 0.9300 . ? O6 O9 1.74(3) . ? O8 O9 1.47(2) . ? 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 Zn1 O3 179.999(1) 2_576 . ? O3 Zn1 O1 92.72(14) 2_576 2_576 ? O3 Zn1 O1 87.28(14) . 2_576 ? O3 Zn1 O1 87.28(14) 2_576 . ? O3 Zn1 O1 92.72(14) . . ? O1 Zn1 O1 179.999(1) 2_576 . ? O3 Zn1 N6 93.18(15) 2_576 2_576 ? O3 Zn1 N6 86.82(15) . 2_576 ? O1 Zn1 N6 90.37(14) 2_576 2_576 ? O1 Zn1 N6 89.63(14) . 2_576 ? O3 Zn1 N6 86.82(15) 2_576 . ? O3 Zn1 N6 93.18(15) . . ? O1 Zn1 N6 89.63(14) 2_576 . ? O1 Zn1 N6 90.37(14) . . ? N6 Zn1 N6 180.0 2_576 . ? N1 Zn2 N1 179.999(1) 2_566 . ? N1 Zn2 O2 78.44(14) 2_566 2_566 ? N1 Zn2 O2 101.56(14) . 2_566 ? N1 Zn2 O2 101.56(14) 2_566 . ? N1 Zn2 O2 78.44(14) . . ? O2 Zn2 O2 180.0 2_566 . ? N1 Zn2 N4 89.77(15) 2_566 . ? N1 Zn2 N4 90.22(15) . . ? O2 Zn2 N4 94.12(14) 2_566 . ? O2 Zn2 N4 85.88(14) . . ? N1 Zn2 N4 90.23(15) 2_566 2_566 ? N1 Zn2 N4 89.78(15) . 2_566 ? O2 Zn2 N4 85.88(14) 2_566 2_566 ? O2 Zn2 N4 94.12(14) . 2_566 ? N4 Zn2 N4 180.0 . 2_566 ? N3 Zn3 N3 180.0 . 2_575 ? N3 Zn3 O4 101.56(15) . 2_575 ? N3 Zn3 O4 78.44(15) 2_575 2_575 ? N3 Zn3 O4 78.44(15) . . ? N3 Zn3 O4 101.56(15) 2_575 . ? O4 Zn3 O4 180.0 2_575 . ? N3 Zn3 N5 90.66(16) . . ? N3 Zn3 N5 89.34(16) 2_575 . ? O4 Zn3 N5 91.80(16) 2_575 . ? O4 Zn3 N5 88.20(16) . . ? N3 Zn3 N5 89.34(16) . 2_575 ? N3 Zn3 N5 90.66(16) 2_575 2_575 ? O4 Zn3 N5 88.20(16) 2_575 2_575 ? O4 Zn3 N5 91.80(16) . 2_575 ? N5 Zn3 N5 180.0 . 2_575 ? C1 O1 Zn1 127.3(3) . . ? C1 O2 Zn2 115.7(3) . . ? C4 O3 Zn1 136.2(3) . . ? C4 O4 Zn3 115.4(3) . . ? N2 N1 C2 109.5(4) . . ? N2 N1 Zn2 136.8(3) . . ? C2 N1 Zn2 113.7(3) . . ? C19 N6 C15 117.3(4) . . ? C19 N6 Zn1 122.2(3) . . ? C15 N6 Zn1 119.8(3) . . ? C9 N4 C5 117.4(4) . . ? C9 N4 Zn2 122.6(3) . . ? C5 N4 Zn2 118.4(3) . . ? N3 N2 N1 108.1(4) . . ? N6 C19 C18 123.2(5) . . ? N6 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? N1 C2 C3 106.4(4) . . ? N1 C2 C1 117.2(4) . . ? C3 C2 C1 136.4(4) . . ? N2 N3 C3 109.2(4) . . ? N2 N3 Zn3 137.5(3) . . ? C3 N3 Zn3 112.8(3) . . ? O3 C4 O4 123.7(4) . . ? O3 C4 C3 121.9(4) . . ? O4 C4 C3 114.4(4) . . ? C6 C7 C8 117.6(4) . . ? C6 C7 C17 120.7(5) . 1_455 ? C8 C7 C17 121.6(5) . 1_455 ? C15 C16 C17 119.5(5) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C19 C18 C17 119.3(5) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? N4 C9 C8 123.2(5) . . ? N4 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? C14 N5 C10 116.7(5) . . ? C14 N5 Zn3 121.8(4) . . ? C10 N5 Zn3 121.3(4) . . ? O1 C1 O2 124.5(4) . . ? O1 C1 C2 120.5(4) . . ? O2 C1 C2 115.0(4) . . ? N3 C3 C2 106.8(4) . . ? N3 C3 C4 117.3(4) . . ? C2 C3 C4 135.9(5) . . ? C16 C17 C18 117.4(4) . . ? C16 C17 C7 121.2(4) . 1_655 ? C18 C17 C7 121.3(4) . 1_655 ? N6 C15 C16 123.2(5) . . ? N6 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C9 C8 C7 118.9(5) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C5 C6 C7 119.3(5) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N4 C5 C6 123.4(5) . . ? N4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C11 C12 C13 116.4(5) . . ? C11 C12 C12 121.8(6) . 2_675 ? C13 C12 C12 121.8(6) . 2_675 ? C10 C11 C12 120.0(6) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N5 C14 C13 123.6(6) . . ? N5 C14 H14 118.2 . . ? C13 C14 H14 118.2 . . ? C14 C13 C12 119.9(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N5 C10 C11 123.5(5) . . ? N5 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C21 C22 C23 110.9(10) . . ? C21 C22 C22 129.2(10) . 2_676 ? C23 C22 C22 119.8(10) . 2_676 ? C24 N7 C20 111.5(12) . . ? C20 C21 C22 125.7(12) . . ? C20 C21 H21 117.1 . . ? C22 C21 H21 117.1 . . ? C22 C23 C24 120.9(11) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C21 C20 N7 126.3(13) . . ? C21 C20 H20 116.9 . . ? N7 C20 H20 116.9 . . ? N7 C24 C23 124.4(12) . . ? N7 C24 H24 117.8 . . ? C23 C24 H24 117.8 . . ? O8 O9 O6 139.3(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.607 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.125 data_2 _database_code_depnum_ccdc_archive 'CCDC 909599' #TrackingRef '123-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H30 N16 O13 Zn3' _chemical_formula_weight 1054.92 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 orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 39.4912(15) _cell_length_b 23.7984(12) _cell_length_c 8.9131(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8376.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3236 _cell_measurement_theta_min 2.4890 _cell_measurement_theta_max 29.068 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4208 _exptl_absorpt_coefficient_mu 1.787 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.87529 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details CRYSALISPRO _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19282 _diffrn_reflns_av_R_equivalents 0.0739 _diffrn_reflns_av_sigmaI/netI 0.1065 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.01 _reflns_number_total 7375 _reflns_number_gt 4494 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSALISPRO _computing_cell_refinement CRYSALISPRO _computing_data_reduction CRYSALISPRO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+38.8276P] 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 7375 _refine_ls_number_parameters 614 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.02164(2) 0.66373(3) 0.58594(9) 0.0134(2) Uani 1 1 d . . . Zn2 Zn -0.09973(2) 0.83276(4) 0.42846(9) 0.0159(2) Uani 1 1 d . . . Zn3 Zn 0.14428(2) 0.82962(4) 0.41948(9) 0.0164(2) Uani 1 1 d . . . C7 C 0.11932(17) 0.7285(3) 0.5776(8) 0.0149(16) Uani 1 1 d U . . N3 N -0.02384(15) 0.7107(2) 0.5319(6) 0.0146(13) Uani 1 1 d . . . N13 N 0.18584(15) 0.8874(3) 0.3926(7) 0.0186(15) Uani 1 1 d . . . N16 N 0.35708(15) 1.1140(3) 0.1064(7) 0.0204(15) Uani 1 1 d . . . N2 N -0.03159(14) 0.7565(3) 0.4573(7) 0.0175(15) Uani 1 1 d . . . N1 N -0.06355(15) 0.7700(3) 0.4896(6) 0.0171(15) Uani 1 1 d . . . N6 N 0.10747(14) 0.7659(3) 0.4771(6) 0.0153(14) Uani 1 1 d . . . N4 N 0.06616(15) 0.7082(2) 0.5269(6) 0.0151(14) Uani 1 1 d . . . N5 N 0.07551(14) 0.7536(3) 0.4474(6) 0.0151(14) Uani 1 1 d . . . C2 C -0.07548(16) 0.7318(3) 0.5899(8) 0.0129(16) Uani 1 1 d . . . C6 C 0.09349(17) 0.6915(3) 0.6110(8) 0.0115(16) Uani 1 1 d U . . C3 C -0.04995(17) 0.6935(3) 0.6163(8) 0.0138(16) Uani 1 1 d . . . C28 C 0.2446(2) 0.9055(4) 0.4133(10) 0.036(2) Uani 1 1 d . . . H28 H 0.2655 0.8950 0.4523 0.044 Uiso 1 1 calc R . . C24 C 0.21619(19) 0.8743(4) 0.4444(10) 0.031(2) Uani 1 1 d . . . H24 H 0.2184 0.8425 0.5045 0.037 Uiso 1 1 calc R . . C26 C 0.2099(2) 0.9666(4) 0.2680(10) 0.031(2) Uani 1 1 d . . . H26 H 0.2071 0.9980 0.2071 0.037 Uiso 1 1 calc R . . N14 N 0.27226(17) 0.9838(3) 0.2978(9) 0.038(2) Uani 1 1 d . . . C27 C 0.24174(19) 0.9524(4) 0.3239(9) 0.029(2) Uani 1 1 d . . . C29 C 0.3004(2) 1.0496(4) 0.1699(10) 0.032(2) Uani 1 1 d . . . C32 C 0.3549(2) 1.0837(4) 0.2307(10) 0.033(2) Uani 1 1 d . . . H32 H 0.3730 1.0850 0.2978 0.039 Uiso 1 1 calc R . . C31 C 0.3316(2) 1.1117(5) 0.0138(10) 0.049(3) Uani 1 1 d . . . H31 H 0.3328 1.1321 -0.0750 0.059 Uiso 1 1 calc R . . C33 C 0.3276(2) 1.0507(4) 0.2661(10) 0.033(2) Uani 1 1 d . . . H33 H 0.3275 1.0294 0.3536 0.039 Uiso 1 1 calc R . . N15 N 0.26983(17) 1.0176(4) 0.1934(9) 0.043(2) Uani 1 1 d . . . C30 C 0.3026(3) 1.0804(5) 0.0413(12) 0.064(4) Uani 1 1 d . . . H30 H 0.2848 1.0805 -0.0273 0.077 Uiso 1 1 calc R . . C25 C 0.1827(2) 0.9332(4) 0.3048(9) 0.028(2) Uani 1 1 d . . . H25 H 0.1614 0.9425 0.2677 0.034 Uiso 1 1 calc R . . O1 O -0.12680(12) 0.7822(2) 0.5841(6) 0.0238(13) Uani 1 1 d . . . O8 O 0.17185(12) 0.7738(2) 0.5567(6) 0.0210(13) Uani 1 1 d . . . O5 O 0.06057(12) 0.6152(2) 0.6888(5) 0.0174(12) Uani 1 1 d . . . C5 C 0.08838(18) 0.6405(3) 0.7055(8) 0.0145(17) Uani 1 1 d . . . C1 C -0.11096(19) 0.7428(3) 0.6475(8) 0.0188(18) Uani 1 1 d . . . C8 C 0.15499(17) 0.7371(3) 0.6277(8) 0.0127(16) Uani 1 1 d . . . O6 O 0.11159(12) 0.6236(2) 0.7921(5) 0.0176(12) Uani 1 1 d . . . O7 O 0.16681(12) 0.7095(2) 0.7345(6) 0.0218(13) Uani 1 1 d . . . O4 O -0.01752(12) 0.6165(2) 0.6896(6) 0.0207(12) Uani 1 1 d . . . O2 O -0.12195(12) 0.7144(2) 0.7539(6) 0.0242(13) Uani 1 1 d . . . C4 C -0.04535(18) 0.6403(3) 0.7042(8) 0.0153(17) Uani 1 1 d . . . O3 O -0.06954(12) 0.6228(2) 0.7832(6) 0.0200(12) Uani 1 1 d . . . N7 N 0.01890(15) 0.6164(3) 0.3862(7) 0.0217(15) Uani 1 1 d . . . C13 C 0.01604(19) 0.5609(3) 0.3923(9) 0.0226(19) Uani 1 1 d . . . H13 H 0.0172 0.5439 0.4861 0.027 Uiso 1 1 calc R . . C9 C 0.0181(2) 0.6404(3) 0.2506(9) 0.030(2) Uani 1 1 d . . . H9 H 0.0198 0.6793 0.2454 0.037 Uiso 1 1 calc R . . N9 N 0.13153(16) 0.8756(3) 0.6277(7) 0.0231(16) Uani 1 1 d . . . C18 C 0.1067(2) 0.9128(4) 0.6299(10) 0.029(2) Uani 1 1 d . . . H18 H 0.0936 0.9171 0.5440 0.035 Uiso 1 1 calc R . . C14 C 0.1502(2) 0.8698(4) 0.7516(9) 0.031(2) Uani 1 1 d . . . H14 H 0.1680 0.8441 0.7507 0.037 Uiso 1 1 calc R . . N12 N 0.08426(18) 1.1101(3) 1.3883(7) 0.0274(17) Uani 1 1 d . . . C10 C 0.0149(2) 0.6111(3) 0.1182(9) 0.033(2) Uani 1 1 d . . . H10 H 0.0158 0.6289 0.0254 0.040 Uiso 1 1 calc R . . C15 C 0.1443(2) 0.9005(4) 0.8824(9) 0.031(2) Uani 1 1 d . . . H15 H 0.1576 0.8953 0.9672 0.037 Uiso 1 1 calc R . . C16 C 0.1186(2) 0.9379(4) 0.8824(8) 0.025(2) Uani 1 1 d . . . N8 N 0.0081(2) 0.5220(3) -0.0080(8) 0.043(2) Uani 1 1 d . . . C17 C 0.0992(2) 0.9457(4) 0.7537(10) 0.031(2) Uani 1 1 d . . . H17 H 0.0818 0.9721 0.7510 0.037 Uiso 1 1 calc R . . C21 C 0.0866(2) 1.0558(4) 1.4039(10) 0.043(3) Uani 1 1 d . . . H21 H 0.0867 1.0418 1.5013 0.051 Uiso 1 1 calc R . . C11 C 0.0101(2) 0.5530(4) 0.1312(9) 0.032(2) Uani 1 1 d . . . C12 C 0.0114(2) 0.5266(4) 0.2691(9) 0.033(2) Uani 1 1 d . . . H12 H 0.0093 0.4878 0.2784 0.039 Uiso 1 1 calc R . . C22 C 0.0810(3) 1.1270(4) 1.2492(11) 0.064(4) Uani 1 1 d . . . H22 H 0.0777 1.1652 1.2333 0.077 Uiso 1 1 calc R . . N11 N 0.09071(18) 1.0035(3) 1.0135(8) 0.0313(18) Uani 1 1 d . . . N10 N 0.11463(19) 0.9713(3) 1.0173(8) 0.0356(19) Uani 1 1 d . . . C19 C 0.0879(2) 1.0375(3) 1.1469(9) 0.026(2) Uani 1 1 d . . . C20 C 0.0887(3) 1.0174(4) 1.2891(10) 0.044(3) Uani 1 1 d . . . H20 H 0.0907 0.9791 1.3084 0.053 Uiso 1 1 calc R . . C23 C 0.0820(3) 1.0930(5) 1.1250(11) 0.069(4) Uani 1 1 d . . . H23 H 0.0787 1.1075 1.0292 0.083 Uiso 1 1 calc R . . O9 O 0.02147(13) 0.7151(2) 0.7786(6) 0.0292(14) Uani 1 1 d . . . H9A H 0.0070 0.7029 0.8456 0.044 Uiso 1 1 d R . . H9B H 0.0415 0.7145 0.8196 0.044 Uiso 1 1 d R . . O14 O -0.21905(18) 0.7794(4) 0.5701(8) 0.079(3) Uani 1 1 d . . . O10 O 0.2218(3) 0.7826(6) 0.8489(14) 0.056(4) Uani 0.50 1 d P . . O15 O -0.2632(3) 0.8588(6) 0.6484(15) 0.054(4) Uani 0.50 1 d P . . O16 O -0.2908(4) 0.8798(7) 0.3651(17) 0.069(5) Uani 0.50 1 d P . . O11 O 0.2409(5) 0.7697(8) 1.096(2) 0.114(8) Uani 0.50 1 d PU . . O12 O -0.1929(3) 0.7173(7) 0.7861(15) 0.047(4) Uani 0.50 1 d P . . O13 O -0.1850(4) 0.7677(8) 0.8399(16) 0.067(5) Uani 0.50 1 d P . . 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 0.0120(4) 0.0129(4) 0.0152(4) -0.0023(4) 0.0007(4) 0.0009(4) Zn2 0.0171(4) 0.0166(5) 0.0140(4) 0.0013(4) 0.0006(4) 0.0069(4) Zn3 0.0162(4) 0.0184(5) 0.0148(4) -0.0003(4) 0.0012(4) -0.0053(4) C7 0.015(3) 0.015(3) 0.015(3) -0.002(3) 0.007(3) 0.004(3) N3 0.018(3) 0.009(3) 0.016(3) -0.002(3) 0.001(3) 0.003(3) N13 0.018(3) 0.021(4) 0.017(3) -0.007(3) -0.002(3) -0.010(3) N16 0.021(3) 0.022(4) 0.019(4) 0.006(3) -0.003(3) -0.010(3) N2 0.011(3) 0.018(4) 0.023(4) -0.001(3) 0.003(3) 0.003(3) N1 0.019(3) 0.018(4) 0.015(3) 0.001(3) 0.000(3) 0.003(3) N6 0.011(3) 0.020(4) 0.015(3) 0.001(3) 0.000(3) -0.001(3) N4 0.014(3) 0.016(3) 0.015(3) 0.003(3) 0.002(3) 0.001(3) N5 0.014(3) 0.019(3) 0.013(3) 0.001(3) 0.000(3) -0.001(3) C2 0.012(3) 0.012(4) 0.014(4) -0.003(3) 0.001(3) 0.001(3) C6 0.0119(17) 0.0112(18) 0.0115(18) -0.0009(10) -0.0001(10) -0.0003(10) C3 0.007(3) 0.018(4) 0.016(4) 0.002(3) 0.003(3) -0.004(3) C28 0.025(5) 0.039(6) 0.045(6) 0.010(5) -0.003(5) -0.010(4) C24 0.023(4) 0.029(5) 0.042(6) 0.006(4) -0.009(4) -0.015(4) C26 0.023(4) 0.028(5) 0.041(5) 0.003(4) -0.006(4) -0.006(4) N14 0.024(4) 0.040(5) 0.049(5) 0.014(4) 0.003(4) -0.015(4) C27 0.021(5) 0.034(5) 0.031(5) 0.001(4) 0.007(4) -0.015(4) C29 0.020(4) 0.038(6) 0.039(6) 0.006(5) -0.004(4) -0.019(4) C32 0.022(4) 0.033(5) 0.043(6) 0.012(5) -0.003(4) -0.004(4) C31 0.038(5) 0.072(8) 0.037(6) 0.035(6) -0.016(5) -0.022(6) C33 0.032(5) 0.031(5) 0.035(5) 0.014(4) 0.001(4) -0.006(4) N15 0.025(4) 0.052(6) 0.051(5) 0.009(5) -0.010(4) -0.020(4) C30 0.045(6) 0.089(9) 0.059(7) 0.032(7) -0.030(6) -0.047(7) C25 0.017(4) 0.024(5) 0.044(6) 0.008(4) 0.000(4) -0.003(4) O1 0.019(3) 0.030(3) 0.023(3) 0.009(3) 0.004(3) 0.009(3) O8 0.018(3) 0.022(3) 0.023(3) 0.008(2) -0.001(3) -0.005(3) O5 0.015(3) 0.012(3) 0.025(3) 0.001(2) 0.000(2) -0.002(2) C5 0.015(4) 0.014(4) 0.015(4) -0.002(3) 0.006(3) 0.008(4) C1 0.021(4) 0.019(5) 0.016(4) 0.002(4) -0.005(4) 0.010(4) C8 0.013(3) 0.014(4) 0.011(4) 0.000(3) -0.002(3) 0.008(3) O6 0.015(3) 0.016(3) 0.022(3) 0.003(2) 0.002(2) 0.003(2) O7 0.017(3) 0.027(3) 0.021(3) 0.006(3) -0.002(3) 0.001(3) O4 0.019(3) 0.015(3) 0.028(3) 0.006(2) 0.002(3) 0.004(3) O2 0.015(3) 0.035(4) 0.022(3) 0.008(3) 0.001(2) -0.002(3) C4 0.013(4) 0.018(4) 0.015(4) -0.003(3) -0.004(3) -0.006(4) O3 0.017(3) 0.019(3) 0.024(3) -0.004(2) 0.010(3) -0.003(3) N7 0.015(3) 0.022(4) 0.028(4) -0.008(3) 0.000(3) -0.003(3) C13 0.026(4) 0.019(4) 0.023(4) -0.003(4) -0.002(4) 0.002(4) C9 0.047(6) 0.012(4) 0.032(5) -0.001(4) 0.003(5) 0.001(4) N9 0.024(4) 0.025(4) 0.020(4) -0.003(3) 0.004(3) -0.007(3) C18 0.021(4) 0.039(6) 0.028(5) 0.003(4) 0.004(4) -0.004(4) C14 0.039(5) 0.031(5) 0.021(5) -0.009(4) 0.001(4) 0.009(5) N12 0.045(4) 0.018(4) 0.019(4) -0.006(3) -0.008(4) 0.016(4) C10 0.061(7) 0.022(5) 0.017(4) 0.002(4) -0.002(4) -0.009(5) C15 0.043(5) 0.026(5) 0.025(5) -0.004(4) -0.007(4) 0.007(5) C16 0.027(4) 0.032(5) 0.016(4) -0.001(4) 0.003(4) -0.009(4) N8 0.075(6) 0.027(4) 0.025(4) -0.011(4) -0.008(4) -0.003(4) C17 0.024(4) 0.030(5) 0.038(5) -0.008(4) 0.014(4) 0.007(4) C21 0.061(6) 0.046(6) 0.021(5) -0.006(5) 0.011(5) -0.016(6) C11 0.042(5) 0.030(5) 0.024(5) -0.005(4) -0.005(4) -0.005(5) C12 0.043(5) 0.026(5) 0.029(5) 0.002(4) -0.002(4) -0.009(5) C22 0.121(11) 0.020(6) 0.050(7) -0.011(5) -0.040(7) 0.024(6) N11 0.034(4) 0.021(4) 0.039(4) -0.010(3) 0.003(4) 0.002(4) N10 0.040(4) 0.039(5) 0.028(4) -0.011(4) -0.002(4) -0.006(4) C19 0.037(5) 0.021(5) 0.019(4) -0.010(4) 0.002(4) 0.011(4) C20 0.083(8) 0.020(5) 0.030(5) -0.006(4) 0.011(6) -0.011(5) C23 0.117(11) 0.058(8) 0.033(6) -0.018(6) -0.027(7) 0.012(8) O9 0.015(3) 0.049(4) 0.024(3) -0.018(3) -0.001(3) -0.004(3) O14 0.052(5) 0.123(8) 0.062(5) 0.008(5) 0.002(4) -0.009(5) O10 0.037(7) 0.088(12) 0.043(8) 0.018(8) -0.003(7) -0.027(8) O15 0.048(8) 0.065(10) 0.050(8) -0.002(8) 0.025(7) 0.002(8) O16 0.063(10) 0.081(12) 0.062(10) 0.002(9) -0.006(9) 0.015(10) O11 0.105(11) 0.130(12) 0.106(9) 0.012(8) 0.002(8) -0.026(9) O12 0.019(6) 0.076(11) 0.046(8) -0.006(8) 0.001(6) -0.011(7) O13 0.046(9) 0.099(14) 0.057(10) -0.001(10) 0.011(8) 0.035(10) _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 O9 2.107(5) . ? Zn1 N7 2.110(6) . ? Zn1 N4 2.119(6) . ? Zn1 O4 2.123(5) . ? Zn1 O5 2.130(5) . ? Zn1 N3 2.169(6) . ? Zn2 O3 2.053(5) 8_575 ? Zn2 O2 2.110(5) 8_575 ? Zn2 O1 2.125(5) . ? Zn2 N1 2.138(6) . ? Zn2 N16 2.148(6) 3_475 ? Zn2 N12 2.211(6) 5_577 ? Zn3 O6 2.048(5) 8_575 ? Zn3 O7 2.092(5) 8_575 ? Zn3 O8 2.109(5) . ? Zn3 N13 2.154(6) . ? Zn3 N6 2.163(6) . ? Zn3 N9 2.212(6) . ? C7 N6 1.346(9) . ? C7 C6 1.380(9) . ? C7 C8 1.491(9) . ? N3 N2 1.315(8) . ? N3 C3 1.340(8) . ? N13 C24 1.322(10) . ? N13 C25 1.347(10) . ? N16 C31 1.304(10) . ? N16 C32 1.324(10) . ? N16 Zn2 2.148(6) 3_575 ? N2 N1 1.334(8) . ? N1 C2 1.359(9) . ? N6 N5 1.322(8) . ? N4 N5 1.343(8) . ? N4 C6 1.372(8) . ? C2 C3 1.379(9) . ? C2 C1 1.515(10) . ? C6 C5 1.492(10) . ? C3 C4 1.500(10) . ? C28 C24 1.373(11) . ? C28 C27 1.377(11) . ? C28 H28 0.9300 . ? C24 H24 0.9300 . ? C26 C25 1.377(11) . ? C26 C27 1.393(11) . ? C26 H26 0.9300 . ? N14 N15 1.234(9) . ? N14 C27 1.437(9) . ? C29 C30 1.364(12) . ? C29 C33 1.375(11) . ? C29 N15 1.443(10) . ? C32 C33 1.372(11) . ? C32 H32 0.9300 . ? C31 C30 1.387(12) . ? C31 H31 0.9300 . ? C33 H33 0.9300 . ? C30 H30 0.9300 . ? C25 H25 0.9300 . ? O1 C1 1.261(8) . ? O8 C8 1.267(8) . ? O5 C5 1.261(8) . ? C5 O6 1.264(8) . ? C1 O2 1.242(9) . ? C8 O7 1.247(8) . ? O6 Zn3 2.048(5) 8_576 ? O7 Zn3 2.092(5) 8_576 ? O4 C4 1.244(8) . ? O2 Zn2 2.110(5) 8_576 ? C4 O3 1.258(8) . ? O3 Zn2 2.053(5) 8_576 ? N7 C13 1.327(9) . ? N7 C9 1.338(10) . ? C13 C12 1.380(11) . ? C13 H13 0.9300 . ? C9 C10 1.376(11) . ? C9 H9 0.9300 . ? N9 C18 1.322(10) . ? N9 C14 1.335(10) . ? C18 C17 1.385(11) . ? C18 H18 0.9300 . ? C14 C15 1.397(11) . ? C14 H14 0.9300 . ? N12 C21 1.303(11) . ? N12 C22 1.310(11) . ? N12 Zn2 2.211(6) 5_577 ? C10 C11 1.399(11) . ? C10 H10 0.9300 . ? C15 C16 1.348(11) . ? C15 H15 0.9300 . ? C16 C17 1.393(11) . ? C16 N10 1.451(10) . ? N8 N8 1.237(14) 5_565 ? N8 C11 1.446(10) . ? C17 H17 0.9300 . ? C21 C20 1.374(12) . ? C21 H21 0.9300 . ? C11 C12 1.382(11) . ? C12 H12 0.9300 . ? C22 C23 1.372(13) . ? C22 H22 0.9300 . ? N11 N10 1.215(9) . ? N11 C19 1.443(10) . ? C19 C20 1.355(11) . ? C19 C23 1.357(13) . ? C20 H20 0.9300 . ? C23 H23 0.9300 . ? O9 H9A 0.8744 . ? O9 H9B 0.8697 . ? O11 O11 1.18(4) 2_565 ? O12 O13 1.329(19) . ? 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 O9 Zn1 N7 175.6(2) . . ? O9 Zn1 N4 85.1(2) . . ? N7 Zn1 N4 95.7(2) . . ? O9 Zn1 O4 87.1(2) . . ? N7 Zn1 O4 92.7(2) . . ? N4 Zn1 O4 167.7(2) . . ? O9 Zn1 O5 88.0(2) . . ? N7 Zn1 O5 96.4(2) . . ? N4 Zn1 O5 77.2(2) . . ? O4 Zn1 O5 92.95(18) . . ? O9 Zn1 N3 83.1(2) . . ? N7 Zn1 N3 92.6(2) . . ? N4 Zn1 N3 112.0(2) . . ? O4 Zn1 N3 76.5(2) . . ? O5 Zn1 N3 166.5(2) . . ? O3 Zn2 O2 92.9(2) 8_575 8_575 ? O3 Zn2 O1 174.5(2) 8_575 . ? O2 Zn2 O1 88.3(2) 8_575 . ? O3 Zn2 N1 97.6(2) 8_575 . ? O2 Zn2 N1 95.4(2) 8_575 . ? O1 Zn2 N1 76.9(2) . . ? O3 Zn2 N16 93.8(2) 8_575 3_475 ? O2 Zn2 N16 82.9(2) 8_575 3_475 ? O1 Zn2 N16 91.7(2) . 3_475 ? N1 Zn2 N16 168.6(2) . 3_475 ? O3 Zn2 N12 89.4(2) 8_575 5_577 ? O2 Zn2 N12 170.7(2) 8_575 5_577 ? O1 Zn2 N12 90.3(2) . 5_577 ? N1 Zn2 N12 93.2(2) . 5_577 ? N16 Zn2 N12 87.9(2) 3_475 5_577 ? O6 Zn3 O7 94.2(2) 8_575 8_575 ? O6 Zn3 O8 171.65(19) 8_575 . ? O7 Zn3 O8 87.6(2) 8_575 . ? O6 Zn3 N13 94.1(2) 8_575 . ? O7 Zn3 N13 82.7(2) 8_575 . ? O8 Zn3 N13 94.2(2) . . ? O6 Zn3 N6 95.1(2) 8_575 . ? O7 Zn3 N6 99.3(2) 8_575 . ? O8 Zn3 N6 76.5(2) . . ? N13 Zn3 N6 170.4(2) . . ? O6 Zn3 N9 93.0(2) 8_575 . ? O7 Zn3 N9 167.9(2) 8_575 . ? O8 Zn3 N9 86.7(2) . . ? N13 Zn3 N9 87.2(2) . . ? N6 Zn3 N9 89.7(2) . . ? N6 C7 C6 107.9(6) . . ? N6 C7 C8 116.0(6) . . ? C6 C7 C8 136.1(7) . . ? N2 N3 C3 111.0(6) . . ? N2 N3 Zn1 137.1(5) . . ? C3 N3 Zn1 110.8(4) . . ? C24 N13 C25 118.5(7) . . ? C24 N13 Zn3 120.1(5) . . ? C25 N13 Zn3 120.8(5) . . ? C31 N16 C32 117.3(7) . . ? C31 N16 Zn2 123.1(6) . 3_575 ? C32 N16 Zn2 119.5(5) . 3_575 ? N3 N2 N1 108.1(6) . . ? N2 N1 C2 108.0(6) . . ? N2 N1 Zn2 138.2(5) . . ? C2 N1 Zn2 113.8(4) . . ? N5 N6 C7 108.6(6) . . ? N5 N6 Zn3 138.5(5) . . ? C7 N6 Zn3 112.8(5) . . ? N5 N4 C6 107.7(5) . . ? N5 N4 Zn1 139.5(5) . . ? C6 N4 Zn1 111.9(4) . . ? N6 N5 N4 109.6(6) . . ? N1 C2 C3 107.5(6) . . ? N1 C2 C1 115.3(6) . . ? C3 C2 C1 137.1(7) . . ? N4 C6 C7 106.2(6) . . ? N4 C6 C5 115.9(6) . . ? C7 C6 C5 137.8(6) . . ? N3 C3 C2 105.4(6) . . ? N3 C3 C4 117.2(6) . . ? C2 C3 C4 137.3(6) . . ? C24 C28 C27 119.3(8) . . ? C24 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? N13 C24 C28 122.8(8) . . ? N13 C24 H24 118.6 . . ? C28 C24 H24 118.6 . . ? C25 C26 C27 118.5(8) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? N15 N14 C27 113.3(7) . . ? C28 C27 C26 118.5(8) . . ? C28 C27 N14 116.5(7) . . ? C26 C27 N14 124.9(8) . . ? C30 C29 C33 117.7(8) . . ? C30 C29 N15 117.3(8) . . ? C33 C29 N15 125.0(8) . . ? N16 C32 C33 123.6(8) . . ? N16 C32 H32 118.2 . . ? C33 C32 H32 118.2 . . ? N16 C31 C30 123.3(8) . . ? N16 C31 H31 118.4 . . ? C30 C31 H31 118.4 . . ? C32 C33 C29 118.9(8) . . ? C32 C33 H33 120.6 . . ? C29 C33 H33 120.6 . . ? N14 N15 C29 112.8(7) . . ? C29 C30 C31 119.3(9) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? N13 C25 C26 122.4(7) . . ? N13 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C1 O1 Zn2 117.7(5) . . ? C8 O8 Zn3 116.9(4) . . ? C5 O5 Zn1 114.9(5) . . ? O5 C5 O6 123.4(7) . . ? O5 C5 C6 116.1(6) . . ? O6 C5 C6 120.4(6) . . ? O2 C1 O1 124.9(7) . . ? O2 C1 C2 119.2(7) . . ? O1 C1 C2 115.8(7) . . ? O7 C8 O8 123.2(6) . . ? O7 C8 C7 120.7(7) . . ? O8 C8 C7 116.1(6) . . ? C5 O6 Zn3 128.5(5) . 8_576 ? C8 O7 Zn3 132.6(5) . 8_576 ? C4 O4 Zn1 116.7(5) . . ? C1 O2 Zn2 135.0(5) . 8_576 ? O4 C4 O3 125.4(7) . . ? O4 C4 C3 115.9(6) . . ? O3 C4 C3 118.7(6) . . ? C4 O3 Zn2 128.5(5) . 8_576 ? C13 N7 C9 117.4(7) . . ? C13 N7 Zn1 120.1(5) . . ? C9 N7 Zn1 122.4(5) . . ? N7 C13 C12 124.6(8) . . ? N7 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? N7 C9 C10 124.1(7) . . ? N7 C9 H9 117.9 . . ? C10 C9 H9 117.9 . . ? C18 N9 C14 117.9(7) . . ? C18 N9 Zn3 120.8(6) . . ? C14 N9 Zn3 121.1(6) . . ? N9 C18 C17 123.3(8) . . ? N9 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? N9 C14 C15 122.9(8) . . ? N9 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C21 N12 C22 114.3(7) . . ? C21 N12 Zn2 120.8(6) . 5_577 ? C22 N12 Zn2 122.6(6) . 5_577 ? C9 C10 C11 116.2(8) . . ? C9 C10 H10 121.9 . . ? C11 C10 H10 121.9 . . ? C16 C15 C14 118.1(8) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 C17 120.2(8) . . ? C15 C16 N10 116.3(7) . . ? C17 C16 N10 123.3(8) . . ? N8 N8 C11 111.2(9) 5_565 . ? C18 C17 C16 117.5(8) . . ? C18 C17 H17 121.2 . . ? C16 C17 H17 121.2 . . ? N12 C21 C20 125.8(9) . . ? N12 C21 H21 117.1 . . ? C20 C21 H21 117.1 . . ? C12 C11 C10 121.2(8) . . ? C12 C11 N8 122.2(8) . . ? C10 C11 N8 116.1(7) . . ? C13 C12 C11 116.3(8) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? N12 C22 C23 125.5(9) . . ? N12 C22 H22 117.3 . . ? C23 C22 H22 117.3 . . ? N10 N11 C19 112.9(7) . . ? N11 N10 C16 114.0(7) . . ? C20 C19 C23 118.8(8) . . ? C20 C19 N11 124.9(8) . . ? C23 C19 N11 116.2(8) . . ? C19 C20 C21 117.4(9) . . ? C19 C20 H20 121.3 . . ? C21 C20 H20 121.3 . . ? C19 C23 C22 117.6(9) . . ? C19 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? Zn1 O9 H9A 111.5 . . ? Zn1 O9 H9B 109.3 . . ? H9A O9 H9B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.527 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.116 data_3 _database_code_depnum_ccdc_archive 'CCDC 909600' #TrackingRef '123-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cd2 K3 N9 O16' _chemical_formula_weight 876.37 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 7.9992(4) _cell_length_b 7.6259(3) _cell_length_c 20.6651(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.391(4) _cell_angle_gamma 90.00 _cell_volume 1250.11(10) _cell_formula_units_Z 2 _cell_measurement_temperature 121.2 _cell_measurement_reflns_used 3813 _cell_measurement_theta_min 2.5624 _cell_measurement_theta_max 29.2776 _exptl_crystal_description block _exptl_crystal_colour clourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.296 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7102 _exptl_absorpt_correction_T_max 0.8029 _exptl_absorpt_process_details CrysAlisPro _exptl_special_details ; ? ; _diffrn_ambient_temperature 121.2 _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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4561 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2200 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0710P)^2^+7.3129P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2200 _refine_ls_number_parameters 194 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.053 _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 0.50811(5) 0.48730(5) 0.606766(17) 0.0123(2) Uani 1 1 d . . . O3 O -0.1599(5) 0.1423(5) 0.51523(19) 0.0213(9) Uani 1 1 d . . . O5 O 0.5602(5) 0.1913(5) 0.61737(17) 0.0157(8) Uani 1 1 d . . . N5 N 0.7500 0.5506(9) 0.7500 0.0150(13) Uani 1 2 d S . . O2 O 0.0015(5) 0.2451(6) 0.61740(19) 0.0226(9) Uani 1 1 d . . . N2 N 0.2950(6) 0.4194(6) 0.4564(2) 0.0165(10) Uani 1 1 d . . . O4 O -0.1382(5) 0.1354(5) 0.40942(19) 0.0212(9) Uani 1 1 d . . . N3 N 0.1576(6) 0.3318(6) 0.4290(2) 0.0171(10) Uani 1 1 d . . . C4 C -0.0838(6) 0.1800(7) 0.4654(3) 0.0154(11) Uani 1 1 d . . . N4 N 0.6739(6) 0.4466(6) 0.7027(2) 0.0125(9) Uani 1 1 d . . . N1 N 0.3009(6) 0.4241(6) 0.5212(2) 0.0145(9) Uani 1 1 d . . . O1 O 0.2457(5) 0.3822(6) 0.64809(17) 0.0215(9) Uani 1 1 d . . . C1 C 0.1356(7) 0.3215(7) 0.6056(2) 0.0153(11) Uani 1 1 d . . . C2 C 0.1633(6) 0.3386(7) 0.5362(3) 0.0138(11) Uani 1 1 d . . . C5 C 0.7021(6) 0.2773(6) 0.7196(2) 0.0095(10) Uani 1 1 d . . . C6 C 0.6362(6) 0.1380(7) 0.6711(2) 0.0111(10) Uani 1 1 d . . . O7 O 0.4570(6) 0.7751(6) 0.6151(3) 0.0461(14) Uani 1 1 d U . . H7A H 0.3575 0.8200 0.6091 0.055 Uiso 1 1 d R . . H7B H 0.5006 0.8080 0.6540 0.055 Uiso 1 1 d R . . C3 C 0.0747(6) 0.2806(7) 0.4787(2) 0.0129(10) Uani 1 1 d . . . O6 O 0.6583(6) -0.0181(5) 0.6862(2) 0.0207(10) Uani 1 1 d . . . O8 O 1.2500 0.0937(8) 0.7500 0.0399(17) Uani 1 2 d S . . H8 H 1.2743 0.1611 0.7200 0.048 Uiso 1 1 d R . . O9 O 1.2500 -0.3761(8) 0.7500 0.0250(13) Uani 1 2 d S . . H9 H 1.2749 -0.4391 0.7192 0.030 Uiso 1 1 d R . . K1 K 0.97810(18) -0.1587(2) 0.70344(7) 0.0324(4) Uani 1 1 d . . . K2 K 0.5000 0.0000 0.5000 0.0594(8) Uani 1 2 d S . . 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 0.0172(3) 0.0102(3) 0.0075(3) 0.00083(12) -0.00563(17) -0.00179(14) O3 0.0159(19) 0.024(2) 0.023(2) -0.0019(17) 0.0008(16) -0.0040(17) O5 0.0223(19) 0.0111(18) 0.0120(18) -0.0013(14) -0.0050(15) -0.0020(16) N5 0.023(3) 0.010(3) 0.009(3) 0.000 -0.011(3) 0.000 O2 0.019(2) 0.030(2) 0.019(2) -0.0022(17) 0.0025(16) -0.0033(17) N2 0.021(2) 0.018(2) 0.008(2) 0.0030(18) -0.0065(17) -0.007(2) O4 0.0137(18) 0.029(2) 0.020(2) -0.0087(17) -0.0044(15) -0.0020(17) N3 0.019(2) 0.015(2) 0.015(2) -0.0003(18) -0.0062(18) -0.0033(19) C4 0.012(2) 0.012(3) 0.020(3) -0.002(2) -0.003(2) 0.005(2) N4 0.018(2) 0.011(2) 0.007(2) -0.0023(17) -0.0047(17) -0.0011(19) N1 0.021(2) 0.011(2) 0.010(2) 0.0014(17) -0.0061(17) -0.0023(19) O1 0.022(2) 0.029(2) 0.0115(19) -0.0059(16) -0.0026(16) 0.0002(17) C1 0.017(3) 0.016(3) 0.013(3) -0.002(2) 0.000(2) 0.007(2) C2 0.013(3) 0.010(2) 0.017(3) 0.000(2) -0.002(2) 0.003(2) C5 0.012(2) 0.006(2) 0.010(2) 0.0022(19) 0.0002(19) 0.0000(19) C6 0.011(2) 0.014(3) 0.008(2) -0.0010(19) -0.0017(19) -0.003(2) O7 0.022(2) 0.024(2) 0.084(4) -0.023(2) -0.025(2) 0.006(2) C3 0.013(2) 0.013(2) 0.012(2) -0.001(2) -0.0028(19) 0.002(2) O6 0.031(2) 0.0075(19) 0.019(2) -0.0007(14) -0.0138(18) -0.0006(16) O8 0.074(5) 0.022(3) 0.022(3) 0.000 -0.002(3) 0.000 O9 0.035(3) 0.020(3) 0.020(3) 0.000 0.004(2) 0.000 K1 0.0285(7) 0.0395(9) 0.0283(8) -0.0075(6) 0.0001(6) 0.0045(6) K2 0.066(2) 0.0622(19) 0.0498(18) -0.0033(12) 0.0049(15) -0.0101(13) _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 O7 2.243(5) . ? Cd1 N4 2.260(4) . ? Cd1 N2 2.285(5) 3_666 ? Cd1 O5 2.301(4) . ? Cd1 N1 2.314(4) . ? Cd1 O1 2.498(4) . ? O3 C4 1.293(7) . ? O3 K2 2.908(4) 1_455 ? O5 C6 1.262(6) . ? O5 K2 2.818(4) . ? N5 N4 1.342(6) 2_656 ? N5 N4 1.342(6) . ? N5 K1 3.102(5) 1_565 ? N5 K1 3.102(5) 2_666 ? O2 C1 1.271(7) . ? N2 N1 1.333(6) . ? N2 N3 1.347(6) . ? N2 Cd1 2.285(4) 3_666 ? O4 C4 1.231(6) . ? O4 K1 2.807(4) 3_656 ? N3 C3 1.350(7) . ? N3 K1 3.106(5) 3_656 ? C4 C3 1.477(7) . ? N4 C5 1.349(7) . ? N1 C2 1.349(7) . ? O1 C1 1.250(6) . ? C1 C2 1.486(7) . ? C2 C3 1.376(7) . ? C5 C5 1.386(10) 2_656 ? C5 C6 1.509(7) . ? C6 O6 1.238(6) . ? O7 K2 2.988(6) 1_565 ? O7 H7A 0.8603 . ? O7 H7B 0.8704 . ? O6 K1 2.754(5) . ? O6 K1 2.861(5) 2_656 ? O8 K1 2.970(4) 2_756 ? O8 K1 2.970(4) . ? O8 H8 0.8459 . ? O9 K1 2.805(4) . ? O9 K1 2.805(4) 2_756 ? O9 H9 0.8416 . ? K1 O4 2.807(4) 3_656 ? K1 O6 2.861(5) 2_656 ? K1 N5 3.102(5) 1_545 ? K1 N3 3.106(5) 3_656 ? K1 K1 4.339(3) 2_656 ? K1 K1 4.525(3) 2_756 ? K2 O5 2.818(4) 3_656 ? K2 O3 2.908(4) 1_655 ? K2 O3 2.908(4) 3_556 ? K2 O7 2.988(6) 1_545 ? K2 O7 2.988(6) 3_666 ? 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 O7 Cd1 N4 99.16(17) . . ? O7 Cd1 N2 83.4(2) . 3_666 ? N4 Cd1 N2 100.01(16) . 3_666 ? O7 Cd1 O5 170.13(18) . . ? N4 Cd1 O5 72.74(14) . . ? N2 Cd1 O5 103.32(15) 3_666 . ? O7 Cd1 N1 98.20(16) . . ? N4 Cd1 N1 157.48(17) . . ? N2 Cd1 N1 96.13(15) 3_666 . ? O5 Cd1 N1 88.37(14) . . ? O7 Cd1 O1 96.79(18) . . ? N4 Cd1 O1 94.61(14) . . ? N2 Cd1 O1 165.17(13) 3_666 . ? O5 Cd1 O1 78.61(14) . . ? N1 Cd1 O1 69.13(14) . . ? C4 O3 K2 121.7(3) . 1_455 ? C6 O5 Cd1 117.4(3) . . ? C6 O5 K2 126.9(3) . . ? Cd1 O5 K2 114.65(14) . . ? N4 N5 N4 107.6(6) 2_656 . ? N4 N5 K1 114.7(2) 2_656 1_565 ? N4 N5 K1 115.2(2) . 1_565 ? N4 N5 K1 115.2(2) 2_656 2_666 ? N4 N5 K1 114.7(2) . 2_666 ? K1 N5 K1 88.75(18) 1_565 2_666 ? N1 N2 N3 111.0(4) . . ? N1 N2 Cd1 128.8(3) . 3_666 ? N3 N2 Cd1 119.9(3) . 3_666 ? C4 O4 K1 128.3(3) . 3_656 ? N2 N3 C3 106.1(4) . . ? N2 N3 K1 139.0(3) . 3_656 ? C3 N3 K1 113.4(3) . 3_656 ? O4 C4 O3 122.8(5) . . ? O4 C4 C3 120.6(5) . . ? O3 C4 C3 116.7(5) . . ? N5 N4 C5 109.4(4) . . ? N5 N4 Cd1 135.9(4) . . ? C5 N4 Cd1 114.7(3) . . ? N2 N1 C2 107.0(4) . . ? N2 N1 Cd1 134.6(3) . . ? C2 N1 Cd1 116.8(3) . . ? C1 O1 Cd1 115.2(3) . . ? O1 C1 O2 124.8(5) . . ? O1 C1 C2 117.8(5) . . ? O2 C1 C2 117.4(5) . . ? N1 C2 C3 107.6(5) . . ? N1 C2 C1 119.5(4) . . ? C3 C2 C1 133.0(5) . . ? N4 C5 C5 106.8(3) . 2_656 ? N4 C5 C6 118.0(4) . . ? C5 C5 C6 135.1(3) 2_656 . ? O6 C6 O5 124.7(5) . . ? O6 C6 C5 118.9(4) . . ? O5 C6 C5 116.4(4) . . ? Cd1 O7 K2 117.4(2) . 1_565 ? Cd1 O7 H7A 123.5 . . ? K2 O7 H7A 81.7 1_565 . ? Cd1 O7 H7B 107.3 . . ? K2 O7 H7B 119.7 1_565 . ? H7A O7 H7B 105.8 . . ? N3 C3 C2 108.4(5) . . ? N3 C3 C4 120.2(4) . . ? C2 C3 C4 131.4(5) . . ? C6 O6 K1 120.5(4) . . ? C6 O6 K1 120.3(4) . 2_656 ? K1 O6 K1 101.19(13) . 2_656 ? K1 O8 K1 99.2(2) 2_756 . ? K1 O8 H8 113.8 2_756 . ? K1 O8 H8 112.6 . . ? K1 O9 K1 107.5(2) . 2_756 ? K1 O9 H9 109.0 . . ? K1 O9 H9 110.4 2_756 . ? O6 K1 O9 160.19(12) . . ? O6 K1 O4 112.53(13) . 3_656 ? O9 K1 O4 84.60(9) . 3_656 ? O6 K1 O6 60.93(15) . 2_656 ? O9 K1 O6 107.85(9) . 2_656 ? O4 K1 O6 154.21(13) 3_656 2_656 ? O6 K1 O8 114.76(13) . . ? O9 K1 O8 76.63(14) . . ? O4 K1 O8 80.49(9) 3_656 . ? O6 K1 O8 80.64(10) 2_656 . ? O6 K1 N5 75.22(11) . 1_545 ? O9 K1 N5 86.11(11) . 1_545 ? O4 K1 N5 130.72(11) 3_656 1_545 ? O6 K1 N5 73.78(11) 2_656 1_545 ? O8 K1 N5 142.95(7) . 1_545 ? O6 K1 N3 80.67(13) . 3_656 ? O9 K1 N3 102.63(12) . 3_656 ? O4 K1 N3 55.93(12) 3_656 3_656 ? O6 K1 N3 137.40(13) 2_656 3_656 ? O8 K1 N3 135.99(10) . 3_656 ? N5 K1 N3 79.44(10) 1_545 3_656 ? O6 K1 K1 40.30(10) . 2_656 ? O9 K1 K1 120.47(6) . 2_656 ? O4 K1 K1 150.24(10) 3_656 2_656 ? O6 K1 K1 38.51(9) 2_656 2_656 ? O8 K1 K1 118.61(6) . 2_656 ? N5 K1 K1 45.62(9) 1_545 2_656 ? N3 K1 K1 99.92(10) 3_656 2_656 ? O6 K1 K1 151.78(9) . 2_756 ? O9 K1 K1 36.24(10) . 2_756 ? O4 K1 K1 80.62(8) 3_656 2_756 ? O6 K1 K1 96.04(10) 2_656 2_756 ? O8 K1 K1 40.39(10) . 2_756 ? N5 K1 K1 116.09(6) 1_545 2_756 ? N3 K1 K1 125.64(10) 3_656 2_756 ? K1 K1 K1 128.96(7) 2_656 2_756 ? O5 K2 O5 180.0 . 3_656 ? O5 K2 O3 70.11(11) . 1_655 ? O5 K2 O3 109.88(11) 3_656 1_655 ? O5 K2 O3 109.89(11) . 3_556 ? O5 K2 O3 70.11(11) 3_656 3_556 ? O3 K2 O3 180.0 1_655 3_556 ? O5 K2 O7 68.68(12) . 1_545 ? O5 K2 O7 111.33(12) 3_656 1_545 ? O3 K2 O7 109.27(11) 1_655 1_545 ? O3 K2 O7 70.73(12) 3_556 1_545 ? O5 K2 O7 111.32(12) . 3_666 ? O5 K2 O7 68.68(12) 3_656 3_666 ? O3 K2 O7 70.73(12) 1_655 3_666 ? O3 K2 O7 109.27(11) 3_556 3_666 ? O7 K2 O7 180.00(15) 1_545 3_666 ? 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 O7 Cd1 O5 C6 -28.2(10) . . . . ? N4 Cd1 O5 C6 7.4(4) . . . . ? N2 Cd1 O5 C6 103.9(4) 3_666 . . . ? N1 Cd1 O5 C6 -160.2(4) . . . . ? O1 Cd1 O5 C6 -91.2(4) . . . . ? O7 Cd1 O5 K2 162.8(8) . . . . ? N4 Cd1 O5 K2 -161.6(2) . . . . ? N2 Cd1 O5 K2 -65.08(18) 3_666 . . . ? N1 Cd1 O5 K2 30.83(17) . . . . ? O1 Cd1 O5 K2 99.86(16) . . . . ? N1 N2 N3 C3 0.2(6) . . . . ? Cd1 N2 N3 C3 174.4(3) 3_666 . . . ? N1 N2 N3 K1 -164.2(4) . . . 3_656 ? Cd1 N2 N3 K1 10.0(7) 3_666 . . 3_656 ? K1 O4 C4 O3 -170.7(3) 3_656 . . . ? K1 O4 C4 C3 9.1(7) 3_656 . . . ? K2 O3 C4 O4 -10.9(7) 1_455 . . . ? K2 O3 C4 C3 169.2(3) 1_455 . . . ? N4 N5 N4 C5 -0.3(3) 2_656 . . . ? K1 N5 N4 C5 129.1(4) 1_565 . . . ? K1 N5 N4 C5 -130.0(4) 2_666 . . . ? N4 N5 N4 Cd1 177.0(5) 2_656 . . . ? K1 N5 N4 Cd1 -53.7(4) 1_565 . . . ? K1 N5 N4 Cd1 47.3(5) 2_666 . . . ? O7 Cd1 N4 N5 -9.5(4) . . . . ? N2 Cd1 N4 N5 75.3(4) 3_666 . . . ? O5 Cd1 N4 N5 176.3(4) . . . . ? N1 Cd1 N4 N5 -149.5(4) . . . . ? O1 Cd1 N4 N5 -107.2(4) . . . . ? O7 Cd1 N4 C5 167.7(4) . . . . ? N2 Cd1 N4 C5 -107.5(4) 3_666 . . . ? O5 Cd1 N4 C5 -6.5(3) . . . . ? N1 Cd1 N4 C5 27.7(6) . . . . ? O1 Cd1 N4 C5 70.0(4) . . . . ? N3 N2 N1 C2 -0.4(6) . . . . ? Cd1 N2 N1 C2 -174.0(4) 3_666 . . . ? N3 N2 N1 Cd1 164.0(4) . . . . ? Cd1 N2 N1 Cd1 -9.5(7) 3_666 . . . ? O7 Cd1 N1 N2 91.6(5) . . . . ? N4 Cd1 N1 N2 -128.2(5) . . . . ? N2 Cd1 N1 N2 7.5(6) 3_666 . . . ? O5 Cd1 N1 N2 -95.8(5) . . . . ? O1 Cd1 N1 N2 -174.2(5) . . . . ? O7 Cd1 N1 C2 -105.0(4) . . . . ? N4 Cd1 N1 C2 35.1(7) . . . . ? N2 Cd1 N1 C2 170.8(4) 3_666 . . . ? O5 Cd1 N1 C2 67.6(4) . . . . ? O1 Cd1 N1 C2 -10.8(3) . . . . ? O7 Cd1 O1 C1 106.0(4) . . . . ? N4 Cd1 O1 C1 -154.2(4) . . . . ? N2 Cd1 O1 C1 16.2(8) 3_666 . . . ? O5 Cd1 O1 C1 -82.9(4) . . . . ? N1 Cd1 O1 C1 9.8(4) . . . . ? Cd1 O1 C1 O2 172.3(4) . . . . ? Cd1 O1 C1 C2 -7.3(6) . . . . ? N2 N1 C2 C3 0.5(6) . . . . ? Cd1 N1 C2 C3 -167.2(3) . . . . ? N2 N1 C2 C1 179.7(4) . . . . ? Cd1 N1 C2 C1 12.0(6) . . . . ? O1 C1 C2 N1 -2.6(7) . . . . ? O2 C1 C2 N1 177.7(5) . . . . ? O1 C1 C2 C3 176.3(5) . . . . ? O2 C1 C2 C3 -3.4(9) . . . . ? N5 N4 C5 C5 0.8(6) . . . 2_656 ? Cd1 N4 C5 C5 -177.1(4) . . . 2_656 ? N5 N4 C5 C6 -176.4(4) . . . . ? Cd1 N4 C5 C6 5.7(6) . . . . ? Cd1 O5 C6 O6 172.6(4) . . . . ? K2 O5 C6 O6 -19.9(7) . . . . ? Cd1 O5 C6 C5 -6.8(6) . . . . ? K2 O5 C6 C5 160.6(3) . . . . ? N4 C5 C6 O6 -178.8(5) . . . . ? C5 C5 C6 O6 5.1(10) 2_656 . . . ? N4 C5 C6 O5 0.7(7) . . . . ? C5 C5 C6 O5 -175.4(7) 2_656 . . . ? N4 Cd1 O7 K2 132.20(18) . . . 1_565 ? N2 Cd1 O7 K2 33.08(18) 3_666 . . 1_565 ? O5 Cd1 O7 K2 166.5(7) . . . 1_565 ? N1 Cd1 O7 K2 -62.2(2) . . . 1_565 ? O1 Cd1 O7 K2 -131.99(17) . . . 1_565 ? N2 N3 C3 C2 0.1(6) . . . . ? K1 N3 C3 C2 169.1(3) 3_656 . . . ? N2 N3 C3 C4 180.0(4) . . . . ? K1 N3 C3 C4 -11.1(6) 3_656 . . . ? N1 C2 C3 N3 -0.4(6) . . . . ? C1 C2 C3 N3 -179.5(5) . . . . ? N1 C2 C3 C4 179.8(5) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? O4 C4 C3 N3 3.1(8) . . . . ? O3 C4 C3 N3 -177.0(5) . . . . ? O4 C4 C3 C2 -177.1(5) . . . . ? O3 C4 C3 C2 2.8(8) . . . . ? O5 C6 O6 K1 113.7(5) . . . . ? C5 C6 O6 K1 -66.9(6) . . . . ? O5 C6 O6 K1 -119.0(5) . . . 2_656 ? C5 C6 O6 K1 60.4(6) . . . 2_656 ? C6 O6 K1 O9 151.8(4) . . . . ? K1 O6 K1 O9 16.2(4) 2_656 . . . ? C6 O6 K1 O4 -59.9(4) . . . 3_656 ? K1 O6 K1 O4 164.57(11) 2_656 . . 3_656 ? C6 O6 K1 O6 92.3(4) . . . 2_656 ? K1 O6 K1 O6 -43.22(15) 2_656 . . 2_656 ? C6 O6 K1 O8 29.8(4) . . . . ? K1 O6 K1 O8 -105.75(12) 2_656 . . . ? C6 O6 K1 N5 171.7(4) . . . 1_545 ? K1 O6 K1 N5 36.18(10) 2_656 . . 1_545 ? C6 O6 K1 N3 -106.8(4) . . . 3_656 ? K1 O6 K1 N3 117.63(13) 2_656 . . 3_656 ? C6 O6 K1 K1 135.6(4) . . . 2_656 ? C6 O6 K1 K1 53.7(5) . . . 2_756 ? K1 O6 K1 K1 -81.9(2) 2_656 . . 2_756 ? K1 O9 K1 O6 -127.6(4) 2_756 . . . ? K1 O9 K1 O4 81.49(9) 2_756 . . 3_656 ? K1 O9 K1 O6 -75.39(10) 2_756 . . 2_656 ? K1 O9 K1 O8 0.0 2_756 . . . ? K1 O9 K1 N5 -146.97(7) 2_756 . . 1_545 ? K1 O9 K1 N3 134.77(10) 2_756 . . 3_656 ? K1 O9 K1 K1 -115.55(8) 2_756 . . 2_656 ? K1 O8 K1 O6 162.81(12) 2_756 . . . ? K1 O8 K1 O9 -0.001(1) 2_756 . . . ? K1 O8 K1 O4 -86.66(9) 2_756 . . 3_656 ? K1 O8 K1 O6 111.00(9) 2_756 . . 2_656 ? K1 O8 K1 N5 64.50(19) 2_756 . . 1_545 ? K1 O8 K1 N3 -94.45(17) 2_756 . . 3_656 ? K1 O8 K1 K1 117.65(8) 2_756 . . 2_656 ? C6 O5 K2 O5 -148(10) . . . 3_656 ? Cd1 O5 K2 O5 20(10) . . . 3_656 ? C6 O5 K2 O3 -81.7(4) . . . 1_655 ? Cd1 O5 K2 O3 86.07(17) . . . 1_655 ? C6 O5 K2 O3 98.3(4) . . . 3_556 ? Cd1 O5 K2 O3 -93.93(17) . . . 3_556 ? C6 O5 K2 O7 39.5(4) . . . 1_545 ? Cd1 O5 K2 O7 -152.7(2) . . . 1_545 ? C6 O5 K2 O7 -140.5(4) . . . 3_666 ? Cd1 O5 K2 O7 27.3(2) . . . 3_666 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.499 _refine_diff_density_min -2.333 _refine_diff_density_rms 0.172