# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Jian-Fang Ma' _publ_contact_author_address ; Key Lab for Polyoxometalate Science Department of Chemistry Northeast Normal University Changchun 130024 P.R.China ; _publ_contact_author_email jianfangma@yahoo.com.cn _publ_contact_author_phone +86-431-85098620 _publ_contact_author_fax +86-431-85098620 _publ_author_name 'Jian-Fang Ma' #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 734825' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27.50 Co N5 O5.25' _chemical_formula_weight 540.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3110(15) _cell_length_b 14.363(2) _cell_length_c 17.633(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.889(15) _cell_angle_gamma 90.00 _cell_volume 2579.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1126 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.83 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16114 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 26.45 _reflns_number_total 5210 _reflns_number_gt 3276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecules were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.89+-0.02 \%A with U~iso~ = 1.5U~eq~(O). The distance of water H...H was restrained to 1.44+-0.02 \%A. In order to give a reasonable H...H distance, the distance of H1A...H2B was restrained to 2.50+-0.02 \%A. ; _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^)+(0.0636P)^2^+1.1327P] 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 5210 _refine_ls_number_parameters 332 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.58555(4) 0.26467(3) 0.71721(3) 0.04606(18) Uani 1 1 d . . . C1 C 0.8741(4) 0.2763(3) 0.7211(2) 0.0567(9) Uani 1 1 d . . . H16 H 0.8843 0.2174 0.7432 0.068 Uiso 1 1 calc R . . C2 C 0.7898(4) 0.3996(3) 0.6689(3) 0.0623(11) Uani 1 1 d . . . H17 H 0.7286 0.4437 0.6477 0.075 Uiso 1 1 calc R . . C3 C 0.9208(4) 0.4089(3) 0.6754(3) 0.0670(11) Uani 1 1 d . . . H18 H 0.9663 0.4595 0.6597 0.080 Uiso 1 1 calc R . . C4 C 1.1122(4) 0.3052(4) 0.7259(2) 0.0718(12) Uani 1 1 d . . . H19A H 1.1283 0.2728 0.7747 0.086 Uiso 1 1 calc R . . H19B H 1.1644 0.3617 0.7308 0.086 Uiso 1 1 calc R . . C5 C 1.1558(4) 0.2445(3) 0.6649(2) 0.0739(13) Uani 1 1 d . . . H20A H 1.1064 0.1868 0.6619 0.089 Uiso 1 1 calc R . . H20B H 1.2478 0.2291 0.6801 0.089 Uiso 1 1 calc R . . C6 C 1.1382(4) 0.2892(3) 0.5855(2) 0.0672(11) Uani 1 1 d . . . H21A H 1.0454 0.2949 0.5655 0.081 Uiso 1 1 calc R . . H21B H 1.1764 0.3511 0.5888 0.081 Uiso 1 1 calc R . . C7 C 1.2052(5) 0.2290(4) 0.5320(2) 0.0783(13) Uani 1 1 d . . . H22A H 1.2980 0.2243 0.5522 0.094 Uiso 1 1 calc R . . H22B H 1.1684 0.1668 0.5304 0.094 Uiso 1 1 calc R . . C8 C 1.1296(4) 0.2260(3) 0.3902(2) 0.0563(9) Uani 1 1 d . . . H24 H 1.0870 0.1688 0.3892 0.068 Uiso 1 1 calc R . . C9 C 1.2079(5) 0.3520(3) 0.3554(3) 0.0767(13) Uani 1 1 d . . . H25 H 1.2305 0.4004 0.3249 0.092 Uiso 1 1 calc R . . C10 C 1.2413(5) 0.3473(3) 0.4321(3) 0.0840(14) Uani 1 1 d . . . H23 H 1.2896 0.3908 0.4638 0.101 Uiso 1 1 calc R . . C11 C 0.4504(3) 0.4102(2) 0.6614(2) 0.0521(9) Uani 1 1 d . . . C12 C 0.3746(3) 0.4990(2) 0.6479(2) 0.0467(8) Uani 1 1 d . . . C13 C 0.3860(3) 0.5519(2) 0.5841(2) 0.0489(9) Uani 1 1 d . . . H14 H 0.4405 0.5315 0.5502 0.059 Uiso 1 1 calc R . . C14 C 0.3171(4) 0.6361(2) 0.5691(2) 0.0509(9) Uani 1 1 d . . . C15 C 0.2310(4) 0.6612(3) 0.6196(2) 0.0582(10) Uani 1 1 d . . . H10 H 0.1812 0.7151 0.6105 0.070 Uiso 1 1 calc R . . C16 C 0.2189(4) 0.6072(3) 0.6827(2) 0.0609(10) Uani 1 1 d . . . H11 H 0.1597 0.6248 0.7148 0.073 Uiso 1 1 calc R . . C17 C 0.2925(4) 0.5276(2) 0.6994(2) 0.0556(9) Uani 1 1 d . . . H12 H 0.2876 0.4938 0.7438 0.067 Uiso 1 1 calc R . . C18 C 0.2821(5) 0.7804(3) 0.4924(2) 0.0662(11) Uani 1 1 d . . . H8A H 0.1910 0.7801 0.5003 0.079 Uiso 1 1 calc R . . H8B H 0.2835 0.7959 0.4390 0.079 Uiso 1 1 calc R . . C19 C 0.3541(4) 0.8564(2) 0.5422(2) 0.0513(9) Uani 1 1 d . . . C20 C 0.4870(4) 0.8585(3) 0.5599(3) 0.0677(11) Uani 1 1 d . . . H6 H 0.5354 0.8087 0.5455 0.081 Uiso 1 1 calc R . . C21 C 0.5523(4) 0.9326(3) 0.5986(3) 0.0644(11) Uani 1 1 d . . . H7 H 0.6435 0.9319 0.6095 0.077 Uiso 1 1 calc R . . C22 C 0.4843(3) 1.0070(2) 0.62109(19) 0.0443(8) Uani 1 1 d . . . C23 C 0.3496(4) 1.0039(2) 0.6072(2) 0.0575(10) Uani 1 1 d . . . H3 H 0.3012 1.0523 0.6241 0.069 Uiso 1 1 calc R . . C24 C 0.2850(4) 0.9293(3) 0.5681(2) 0.0630(11) Uani 1 1 d . . . H4 H 0.1937 0.9283 0.5592 0.076 Uiso 1 1 calc R . . C25 C 0.5531(4) 1.0914(2) 0.6577(2) 0.0502(9) Uani 1 1 d . . . N1 N 0.7601(3) 0.31548(19) 0.69815(17) 0.0500(7) Uani 1 1 d . . . N2 N 0.9733(3) 0.3302(2) 0.70909(17) 0.0542(8) Uani 1 1 d . . . N3 N 1.1903(3) 0.2662(2) 0.45394(18) 0.0609(8) Uani 1 1 d . . . N4 N 1.1370(3) 0.2764(2) 0.32891(18) 0.0528(8) Uani 1 1 d . . . O1 O 0.4745(3) 0.37786(17) 0.73000(16) 0.0616(7) Uani 1 1 d . . . O2 O 0.4890(3) 0.36862(18) 0.60672(16) 0.0642(7) Uani 1 1 d . . . O3 O 0.6728(3) 1.09439(18) 0.67625(16) 0.0666(7) Uani 1 1 d . . . O4 O 0.4794(2) 1.16136(16) 0.66741(15) 0.0600(7) Uani 1 1 d . . . O1W O 0.9188(4) 1.0145(3) 0.6434(2) 0.1170(13) Uani 1 1 d D . . H1A H 0.9584 1.0414 0.6870 0.176 Uiso 1 1 d RD . . H1B H 0.8316 1.0242 0.6463 0.176 Uiso 1 1 d RD . . O2W O 1.0229(13) 1.0661(10) 0.5059(7) 0.105(4) Uiso 0.25 1 d PD . . H2A H 1.0551 1.0223 0.4722 0.158 Uiso 0.25 1 d PRD . . H2B H 1.0185 1.0368 0.5544 0.158 Uiso 0.25 1 d PRD . . N5 N 0.3344(4) 0.6880(2) 0.5065(2) 0.0672(10) Uani 1 1 d . . . H5N H 0.384(4) 0.674(3) 0.481(3) 0.081 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0548(3) 0.0360(3) 0.0475(3) -0.0003(2) 0.0082(2) -0.0024(2) C1 0.057(2) 0.050(2) 0.063(2) 0.008(2) 0.0097(19) -0.0051(19) C2 0.061(2) 0.044(2) 0.082(3) 0.004(2) 0.010(2) -0.0052(18) C3 0.070(3) 0.050(2) 0.082(3) 0.002(2) 0.015(2) -0.016(2) C4 0.060(2) 0.095(3) 0.060(3) -0.003(3) 0.008(2) -0.008(2) C5 0.061(2) 0.104(4) 0.057(3) 0.009(3) 0.009(2) 0.015(2) C6 0.059(2) 0.083(3) 0.059(3) 0.002(2) 0.0075(19) 0.011(2) C7 0.092(3) 0.091(3) 0.052(2) 0.011(2) 0.011(2) 0.033(3) C8 0.061(2) 0.051(2) 0.056(2) -0.005(2) 0.0084(19) 0.0066(18) C9 0.119(4) 0.050(2) 0.059(3) -0.008(2) 0.011(3) -0.012(2) C10 0.125(4) 0.066(3) 0.059(3) -0.018(2) 0.008(3) -0.019(3) C11 0.053(2) 0.0388(19) 0.067(3) -0.005(2) 0.0169(19) -0.0057(16) C12 0.050(2) 0.0348(18) 0.057(2) -0.0084(18) 0.0145(17) -0.0032(15) C13 0.060(2) 0.0370(18) 0.054(2) -0.0107(18) 0.0209(17) -0.0038(16) C14 0.069(2) 0.0361(18) 0.048(2) -0.0073(18) 0.0104(18) -0.0067(17) C15 0.069(2) 0.039(2) 0.069(3) 0.000(2) 0.019(2) 0.0098(18) C16 0.067(2) 0.051(2) 0.070(3) -0.006(2) 0.030(2) 0.0045(19) C17 0.071(2) 0.043(2) 0.057(2) -0.0012(19) 0.0226(19) -0.0005(18) C18 0.103(3) 0.044(2) 0.048(2) -0.004(2) 0.002(2) -0.009(2) C19 0.078(3) 0.0316(18) 0.045(2) 0.0045(17) 0.0134(18) 0.0000(17) C20 0.078(3) 0.042(2) 0.087(3) -0.016(2) 0.026(2) 0.007(2) C21 0.061(2) 0.048(2) 0.085(3) -0.010(2) 0.014(2) 0.0045(19) C22 0.057(2) 0.0370(18) 0.0404(19) 0.0027(16) 0.0108(16) -0.0020(15) C23 0.067(3) 0.0396(19) 0.066(3) -0.0103(19) 0.0129(19) 0.0053(17) C24 0.063(2) 0.046(2) 0.076(3) -0.003(2) -0.002(2) 0.0006(18) C25 0.072(3) 0.0382(19) 0.042(2) 0.0030(17) 0.0154(19) -0.0043(18) N1 0.0620(18) 0.0359(16) 0.0532(18) 0.0014(15) 0.0121(14) -0.0023(14) N2 0.0531(18) 0.0564(19) 0.0537(19) -0.0044(16) 0.0108(14) -0.0074(15) N3 0.072(2) 0.063(2) 0.0469(19) -0.0012(18) 0.0074(16) 0.0136(18) N4 0.0705(19) 0.0397(17) 0.0479(18) -0.0014(16) 0.0077(15) 0.0042(14) O1 0.0793(18) 0.0429(14) 0.0649(18) 0.0009(14) 0.0183(14) 0.0083(13) O2 0.0742(17) 0.0505(15) 0.0716(18) -0.0135(14) 0.0236(14) 0.0113(13) O3 0.0629(17) 0.0598(17) 0.0760(19) -0.0067(15) 0.0073(14) -0.0129(13) O4 0.0707(16) 0.0379(13) 0.0699(18) -0.0090(13) 0.0062(13) -0.0034(12) O1W 0.103(3) 0.121(3) 0.126(3) 0.022(3) 0.011(2) 0.005(2) N5 0.114(3) 0.0376(18) 0.056(2) -0.0035(17) 0.0302(19) -0.0018(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 1.968(2) 1_545 ? Co1 N1 2.018(3) . ? Co1 O1 2.021(2) . ? Co1 N4 2.046(3) 4_566 ? C1 N1 1.310(4) . ? C1 N2 1.326(4) . ? C1 H16 0.9300 . ? C2 C3 1.345(5) . ? C2 N1 1.367(5) . ? C2 H17 0.9300 . ? C3 N2 1.351(5) . ? C3 H18 0.9300 . ? C4 N2 1.461(5) . ? C4 C5 1.506(6) . ? C4 H19A 0.9700 . ? C4 H19B 0.9700 . ? C5 C6 1.526(6) . ? C5 H20A 0.9700 . ? C5 H20B 0.9700 . ? C6 C7 1.522(6) . ? C6 H21A 0.9700 . ? C6 H21B 0.9700 . ? C7 N3 1.462(5) . ? C7 H22A 0.9700 . ? C7 H22B 0.9700 . ? C8 N4 1.313(5) . ? C8 N3 1.331(5) . ? C8 H24 0.9300 . ? C9 C10 1.344(6) . ? C9 N4 1.352(5) . ? C9 H25 0.9300 . ? C10 N3 1.358(5) . ? C10 H23 0.9300 . ? C11 O2 1.250(4) . ? C11 O1 1.283(4) . ? C11 C12 1.496(5) . ? C12 C13 1.377(5) . ? C12 C17 1.395(5) . ? C13 C14 1.406(5) . ? C13 H14 0.9300 . ? C14 N5 1.368(5) . ? C14 C15 1.398(5) . ? C15 C16 1.377(5) . ? C15 H10 0.9300 . ? C16 C17 1.379(5) . ? C16 H11 0.9300 . ? C17 H12 0.9300 . ? C18 N5 1.439(5) . ? C18 C19 1.521(5) . ? C18 H8A 0.9700 . ? C18 H8B 0.9700 . ? C19 C20 1.358(5) . ? C19 C24 1.384(5) . ? C20 C21 1.382(5) . ? C20 H6 0.9300 . ? C21 C22 1.370(5) . ? C21 H7 0.9300 . ? C22 C23 1.374(5) . ? C22 C25 1.500(5) . ? C23 C24 1.387(5) . ? C23 H3 0.9300 . ? C24 H4 0.9300 . ? C25 O3 1.228(4) . ? C25 O4 1.287(4) . ? N4 Co1 2.046(3) 4_665 ? O4 Co1 1.968(2) 1_565 ? O1W H1A 0.8988 . ? O1W H1B 0.9193 . ? O2W H2A 0.9601 . ? O2W H2B 0.9602 . ? N5 H5N 0.76(4) . ? 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 O4 Co1 N1 130.33(12) 1_545 . ? O4 Co1 O1 111.75(11) 1_545 . ? N1 Co1 O1 105.25(11) . . ? O4 Co1 N4 104.81(11) 1_545 4_566 ? N1 Co1 N4 99.18(12) . 4_566 ? O1 Co1 N4 101.05(12) . 4_566 ? N1 C1 N2 112.2(3) . . ? N1 C1 H16 123.9 . . ? N2 C1 H16 123.9 . . ? C3 C2 N1 109.6(4) . . ? C3 C2 H17 125.2 . . ? N1 C2 H17 125.2 . . ? C2 C3 N2 106.5(3) . . ? C2 C3 H18 126.8 . . ? N2 C3 H18 126.8 . . ? N2 C4 C5 112.9(3) . . ? N2 C4 H19A 109.0 . . ? C5 C4 H19A 109.0 . . ? N2 C4 H19B 109.0 . . ? C5 C4 H19B 109.0 . . ? H19A C4 H19B 107.8 . . ? C4 C5 C6 113.9(4) . . ? C4 C5 H20A 108.8 . . ? C6 C5 H20A 108.8 . . ? C4 C5 H20B 108.8 . . ? C6 C5 H20B 108.8 . . ? H20A C5 H20B 107.7 . . ? C7 C6 C5 109.2(3) . . ? C7 C6 H21A 109.8 . . ? C5 C6 H21A 109.8 . . ? C7 C6 H21B 109.8 . . ? C5 C6 H21B 109.8 . . ? H21A C6 H21B 108.3 . . ? N3 C7 C6 112.6(3) . . ? N3 C7 H22A 109.1 . . ? C6 C7 H22A 109.1 . . ? N3 C7 H22B 109.1 . . ? C6 C7 H22B 109.1 . . ? H22A C7 H22B 107.8 . . ? N4 C8 N3 112.1(4) . . ? N4 C8 H24 124.0 . . ? N3 C8 H24 124.0 . . ? C10 C9 N4 110.3(4) . . ? C10 C9 H25 124.8 . . ? N4 C9 H25 124.8 . . ? C9 C10 N3 106.2(4) . . ? C9 C10 H23 126.9 . . ? N3 C10 H23 126.9 . . ? O2 C11 O1 121.1(3) . . ? O2 C11 C12 120.3(4) . . ? O1 C11 C12 118.6(3) . . ? C13 C12 C17 120.4(3) . . ? C13 C12 C11 119.5(3) . . ? C17 C12 C11 120.1(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H14 119.2 . . ? C14 C13 H14 119.2 . . ? N5 C14 C15 123.3(3) . . ? N5 C14 C13 119.7(3) . . ? C15 C14 C13 117.0(3) . . ? C16 C15 C14 121.0(3) . . ? C16 C15 H10 119.5 . . ? C14 C15 H10 119.5 . . ? C15 C16 C17 121.6(4) . . ? C15 C16 H11 119.2 . . ? C17 C16 H11 119.2 . . ? C16 C17 C12 118.3(4) . . ? C16 C17 H12 120.8 . . ? C12 C17 H12 120.8 . . ? N5 C18 C19 115.2(3) . . ? N5 C18 H8A 108.5 . . ? C19 C18 H8A 108.5 . . ? N5 C18 H8B 108.5 . . ? C19 C18 H8B 108.5 . . ? H8A C18 H8B 107.5 . . ? C20 C19 C24 117.4(3) . . ? C20 C19 C18 122.3(3) . . ? C24 C19 C18 120.3(4) . . ? C19 C20 C21 121.9(4) . . ? C19 C20 H6 119.1 . . ? C21 C20 H6 119.1 . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H7 119.6 . . ? C20 C21 H7 119.6 . . ? C21 C22 C23 118.2(3) . . ? C21 C22 C25 121.7(3) . . ? C23 C22 C25 120.1(3) . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H3 119.7 . . ? C24 C23 H3 119.7 . . ? C19 C24 C23 121.1(4) . . ? C19 C24 H4 119.4 . . ? C23 C24 H4 119.4 . . ? O3 C25 O4 121.8(3) . . ? O3 C25 C22 122.1(3) . . ? O4 C25 C22 116.0(3) . . ? C1 N1 C2 104.7(3) . . ? C1 N1 Co1 125.0(2) . . ? C2 N1 Co1 129.8(3) . . ? C1 N2 C3 107.0(3) . . ? C1 N2 C4 125.5(4) . . ? C3 N2 C4 127.5(3) . . ? C8 N3 C10 106.6(3) . . ? C8 N3 C7 127.1(4) . . ? C10 N3 C7 126.3(4) . . ? C8 N4 C9 104.8(3) . . ? C8 N4 Co1 126.4(3) . 4_665 ? C9 N4 Co1 127.6(3) . 4_665 ? C11 O1 Co1 102.5(2) . . ? C25 O4 Co1 110.4(2) . 1_565 ? H1A O1W H1B 101.9 . . ? H2A O2W H2B 109.5 . . ? C14 N5 C18 123.4(3) . . ? C14 N5 H5N 121(4) . . ? C18 N5 H5N 114(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.2(5) . . . . ? N2 C4 C5 C6 60.0(5) . . . . ? C4 C5 C6 C7 170.9(4) . . . . ? C5 C6 C7 N3 178.8(4) . . . . ? N4 C9 C10 N3 0.3(6) . . . . ? O2 C11 C12 C13 -22.8(5) . . . . ? O1 C11 C12 C13 157.3(3) . . . . ? O2 C11 C12 C17 156.8(3) . . . . ? O1 C11 C12 C17 -23.1(5) . . . . ? C17 C12 C13 C14 0.6(5) . . . . ? C11 C12 C13 C14 -179.8(3) . . . . ? C12 C13 C14 N5 177.9(3) . . . . ? C12 C13 C14 C15 -3.4(5) . . . . ? N5 C14 C15 C16 -178.9(4) . . . . ? C13 C14 C15 C16 2.4(5) . . . . ? C14 C15 C16 C17 1.3(6) . . . . ? C15 C16 C17 C12 -4.1(6) . . . . ? C13 C12 C17 C16 3.1(5) . . . . ? C11 C12 C17 C16 -176.5(3) . . . . ? N5 C18 C19 C20 40.3(6) . . . . ? N5 C18 C19 C24 -143.1(4) . . . . ? C24 C19 C20 C21 -3.4(6) . . . . ? C18 C19 C20 C21 173.3(4) . . . . ? C19 C20 C21 C22 0.4(7) . . . . ? C20 C21 C22 C23 2.9(6) . . . . ? C20 C21 C22 C25 -175.2(4) . . . . ? C21 C22 C23 C24 -3.0(6) . . . . ? C25 C22 C23 C24 175.1(3) . . . . ? C20 C19 C24 C23 3.2(6) . . . . ? C18 C19 C24 C23 -173.6(4) . . . . ? C22 C23 C24 C19 0.0(6) . . . . ? C21 C22 C25 O3 -7.4(5) . . . . ? C23 C22 C25 O3 174.5(3) . . . . ? C21 C22 C25 O4 171.5(3) . . . . ? C23 C22 C25 O4 -6.5(5) . . . . ? N2 C1 N1 C2 0.7(4) . . . . ? N2 C1 N1 Co1 -172.2(2) . . . . ? C3 C2 N1 C1 -0.3(5) . . . . ? C3 C2 N1 Co1 172.1(3) . . . . ? O4 Co1 N1 C1 -76.3(3) 1_545 . . . ? O1 Co1 N1 C1 146.3(3) . . . . ? N4 Co1 N1 C1 42.1(3) 4_566 . . . ? O4 Co1 N1 C2 112.6(3) 1_545 . . . ? O1 Co1 N1 C2 -24.7(3) . . . . ? N4 Co1 N1 C2 -128.9(3) 4_566 . . . ? N1 C1 N2 C3 -0.9(5) . . . . ? N1 C1 N2 C4 -177.8(3) . . . . ? C2 C3 N2 C1 0.6(5) . . . . ? C2 C3 N2 C4 177.4(4) . . . . ? C5 C4 N2 C1 80.2(5) . . . . ? C5 C4 N2 C3 -96.1(5) . . . . ? N4 C8 N3 C10 -0.8(5) . . . . ? N4 C8 N3 C7 -178.0(3) . . . . ? C9 C10 N3 C8 0.2(5) . . . . ? C9 C10 N3 C7 177.5(4) . . . . ? C6 C7 N3 C8 -117.5(5) . . . . ? C6 C7 N3 C10 65.8(6) . . . . ? N3 C8 N4 C9 1.0(4) . . . . ? N3 C8 N4 Co1 169.5(2) . . . 4_665 ? C10 C9 N4 C8 -0.8(5) . . . . ? C10 C9 N4 Co1 -169.1(3) . . . 4_665 ? O2 C11 O1 Co1 3.3(4) . . . . ? C12 C11 O1 Co1 -176.8(2) . . . . ? O4 Co1 O1 C11 -74.6(2) 1_545 . . . ? N1 Co1 O1 C11 71.6(2) . . . . ? N4 Co1 O1 C11 174.4(2) 4_566 . . . ? O3 C25 O4 Co1 -1.9(4) . . . 1_565 ? C22 C25 O4 Co1 179.2(2) . . . 1_565 ? C15 C14 N5 C18 10.0(6) . . . . ? C13 C14 N5 C18 -171.4(4) . . . . ? C19 C18 N5 C14 75.0(5) . . . . ? 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 O3 0.92 2.06 2.922(5) 155.7 . O2W H2B O1W 0.96 2.03 2.895(13) 148.9 . N5 H5N O2 0.76(4) 2.26(4) 3.014(4) 173(5) 3_666 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.398 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.057 #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 806746' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H52 N10 O9 Zn2' _chemical_formula_weight 1067.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 21.832(3) _cell_length_b 8.627(5) _cell_length_c 25.840(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.013(4) _cell_angle_gamma 90.00 _cell_volume 4793(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 1.801 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.70 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9791 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.90 _diffrn_reflns_theta_max 67.05 _reflns_number_total 4101 _reflns_number_gt 2901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water and amine were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A with U~iso~ = 1.5U~eq~(O) and N---H = 0.87+-0.02 \%A with U~iso~ = 1.5U~eq~(N). The distance of H1WA...HW1B was restrained to 1.44+-0.02 \%A. ; _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^)+(0.1354P)^2^+14.0164P] 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 SHELXL _refine_ls_extinction_coef 0.00034(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4101 _refine_ls_number_parameters 331 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0834 _refine_ls_wR_factor_ref 0.2437 _refine_ls_wR_factor_gt 0.2194 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 0.57133(3) 0.25552(9) 0.11938(3) 0.0397(3) Uani 1 1 d . . . C1 C 0.5600(3) 0.3097(8) 0.0023(3) 0.0466(14) Uani 1 1 d . . . H1 H 0.5460 0.2090 -0.0051 0.056 Uiso 1 1 calc R . . C2 C 0.5906(3) 0.5203(8) 0.0444(3) 0.0525(16) Uani 1 1 d . . . H2 H 0.6023 0.5920 0.0712 0.063 Uiso 1 1 calc R . . C3 C 0.5888(3) 0.5461(9) -0.0072(3) 0.0597(18) Uani 1 1 d . . . H3 H 0.5984 0.6387 -0.0224 0.072 Uiso 1 1 calc R . . C4 C 0.5566(3) 0.3805(11) -0.0914(3) 0.066(2) Uani 1 1 d . . . H4A H 0.5617 0.2705 -0.0973 0.079 Uiso 1 1 calc R . . H4B H 0.5134 0.4065 -0.1045 0.079 Uiso 1 1 calc R . . C5 C 0.5967(3) 0.4688(10) -0.1222(3) 0.0599(18) Uani 1 1 d . . . H5A H 0.5901 0.5787 -0.1174 0.072 Uiso 1 1 calc R . . H5B H 0.5832 0.4458 -0.1592 0.072 Uiso 1 1 calc R . . C6 C 0.6653(3) 0.4368(10) -0.1085(3) 0.0638(19) Uani 1 1 d . . . H6A H 0.6727 0.3266 -0.1116 0.077 Uiso 1 1 calc R . . H6B H 0.6803 0.4672 -0.0724 0.077 Uiso 1 1 calc R . . C7 C 0.7008(3) 0.5265(9) -0.1451(3) 0.0612(18) Uani 1 1 d . . . H7A H 0.6871 0.4912 -0.1809 0.073 Uiso 1 1 calc R . . H7B H 0.6907 0.6357 -0.1437 0.073 Uiso 1 1 calc R . . C8 C 0.8088(3) 0.6127(8) -0.1069(3) 0.0557(17) Uani 1 1 d . . . H8 H 0.7992 0.7101 -0.0951 0.067 Uiso 1 1 calc R . . C9 C 0.8663(3) 0.5505(8) -0.1025(3) 0.0546(16) Uani 1 1 d . . . H9 H 0.9034 0.5986 -0.0879 0.065 Uiso 1 1 calc R . . C10 C 0.8009(3) 0.3831(7) -0.1410(3) 0.0496(15) Uani 1 1 d . . . H10 H 0.7838 0.2940 -0.1580 0.060 Uiso 1 1 calc R . . C11 C 0.6243(3) 0.4925(7) 0.1839(2) 0.0431(13) Uani 1 1 d . . . C12 C 0.6262(3) 0.6493(7) 0.2095(2) 0.0418(13) Uani 1 1 d . . . C13 C 0.6823(3) 0.7193(7) 0.2278(3) 0.0447(14) Uani 1 1 d . . . H13 H 0.7189 0.6662 0.2258 0.054 Uiso 1 1 calc R . . C14 C 0.6858(3) 0.8663(8) 0.2490(3) 0.0472(15) Uani 1 1 d . . . H14 H 0.7244 0.9097 0.2620 0.057 Uiso 1 1 calc R . . C15 C 0.6320(3) 0.9496(7) 0.2512(2) 0.0446(14) Uani 1 1 d . . . C16 C 0.5755(3) 0.8841(10) 0.2309(3) 0.066(2) Uani 1 1 d . . . H16 H 0.5393 0.9413 0.2303 0.079 Uiso 1 1 calc R . . C17 C 0.5717(3) 0.7333(9) 0.2113(3) 0.060(2) Uani 1 1 d . . . H17 H 0.5331 0.6885 0.1995 0.073 Uiso 1 1 calc R . . C18 C 0.6338(3) 1.1117(8) 0.2737(3) 0.0504(15) Uani 1 1 d . . . H18A H 0.6766 1.1470 0.2807 0.060 Uiso 1 1 calc R . . H18B H 0.6108 1.1804 0.2476 0.060 Uiso 1 1 calc R . . C19 C 0.6366(2) 1.0665(6) 0.3690(2) 0.0384(13) Uani 1 1 d . . . C20 C 0.6989(3) 1.0206(8) 0.3775(3) 0.0535(16) Uani 1 1 d . . . H20 H 0.7206 1.0228 0.3496 0.064 Uiso 1 1 calc R . . C21 C 0.7289(3) 0.9721(10) 0.4259(3) 0.068(2) Uani 1 1 d . . . H21 H 0.7704 0.9424 0.4301 0.082 Uiso 1 1 calc R . . C22 C 0.6988(4) 0.9666(11) 0.4683(3) 0.071(2) Uani 1 1 d . . . H22 H 0.7195 0.9361 0.5012 0.085 Uiso 1 1 calc R . . C23 C 0.6362(3) 1.0082(9) 0.4605(3) 0.0583(17) Uani 1 1 d . . . H23 H 0.6150 1.0026 0.4887 0.070 Uiso 1 1 calc R . . C24 C 0.6041(3) 1.0578(7) 0.4121(2) 0.0410(13) Uani 1 1 d . . . C25 C 0.5368(3) 1.0947(7) 0.4084(2) 0.0435(14) Uani 1 1 d . . . N1 N 0.5724(2) 0.3705(6) 0.0510(2) 0.0466(12) Uani 1 1 d . . . N2 N 0.5703(2) 0.4110(6) -0.0333(2) 0.0459(12) Uani 1 1 d . . . N3 N 0.7678(2) 0.5078(6) -0.1316(2) 0.0483(13) Uani 1 1 d . . . N4 N 0.8603(2) 0.4029(6) -0.12338(19) 0.0420(11) Uani 1 1 d . . . O1 O 0.57157(19) 0.4286(6) 0.17024(18) 0.0538(12) Uani 1 1 d . . . O2 O 0.6728(2) 0.4361(6) 0.1745(3) 0.0806(18) Uani 1 1 d . . . O4 O 0.51097(18) 1.1812(5) 0.37146(17) 0.0471(10) Uani 1 1 d . . . O5 O 0.5088(2) 1.0454(7) 0.4431(2) 0.0693(15) Uani 1 1 d . . . O1W O 0.5000 1.3091(13) 0.2500 0.081(2) Uani 1 2 d SD . . H1WA H 0.508(9) 1.388(17) 0.273(7) 0.122 Uiso 0.50 1 d PD . . H1WB H 0.521(10) 1.33(2) 0.224(7) 0.122 Uiso 0.50 1 d PD . . N5 N 0.6082(2) 1.1234(6) 0.3216(2) 0.0474(12) Uani 1 1 d D . . H5N H 0.5692(13) 1.150(9) 0.318(3) 0.057 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0283(5) 0.0391(5) 0.0539(5) -0.0010(3) 0.0129(3) 0.0010(3) C1 0.039(3) 0.043(3) 0.059(4) 0.003(3) 0.013(3) 0.005(3) C2 0.047(4) 0.039(3) 0.074(4) 0.004(3) 0.017(3) -0.004(3) C3 0.053(4) 0.050(4) 0.080(5) 0.026(4) 0.021(3) 0.005(3) C4 0.055(4) 0.084(6) 0.060(4) 0.006(4) 0.013(3) 0.011(4) C5 0.048(4) 0.070(5) 0.063(4) 0.014(4) 0.015(3) 0.012(3) C6 0.047(4) 0.063(5) 0.082(5) 0.018(4) 0.013(3) 0.013(3) C7 0.040(4) 0.060(4) 0.085(5) 0.008(4) 0.014(3) 0.016(3) C8 0.057(4) 0.041(3) 0.073(4) -0.002(3) 0.020(3) 0.013(3) C9 0.044(3) 0.043(3) 0.078(5) -0.007(3) 0.014(3) 0.005(3) C10 0.038(3) 0.038(3) 0.077(4) 0.003(3) 0.022(3) 0.011(3) C11 0.036(3) 0.039(3) 0.055(3) -0.001(3) 0.010(2) -0.003(3) C12 0.032(3) 0.045(3) 0.049(3) -0.001(3) 0.008(2) -0.003(3) C13 0.021(3) 0.038(3) 0.075(4) -0.002(3) 0.007(2) -0.001(2) C14 0.023(3) 0.046(3) 0.071(4) -0.008(3) 0.003(2) 0.000(2) C15 0.036(3) 0.045(3) 0.057(4) -0.007(3) 0.021(3) -0.001(3) C16 0.029(3) 0.070(5) 0.101(6) -0.027(4) 0.018(3) 0.009(3) C17 0.023(3) 0.072(5) 0.088(5) -0.028(4) 0.015(3) -0.006(3) C18 0.046(3) 0.047(4) 0.065(4) -0.005(3) 0.027(3) 0.002(3) C19 0.025(3) 0.033(3) 0.059(3) -0.008(2) 0.009(2) 0.001(2) C20 0.038(3) 0.048(4) 0.077(5) -0.006(3) 0.014(3) 0.001(3) C21 0.034(4) 0.070(5) 0.093(6) -0.007(4) -0.008(4) 0.009(3) C22 0.050(4) 0.080(6) 0.072(5) 0.007(4) -0.017(4) 0.005(4) C23 0.050(4) 0.061(4) 0.063(4) 0.005(3) 0.007(3) 0.001(3) C24 0.027(3) 0.036(3) 0.061(4) -0.003(3) 0.012(2) 0.001(2) C25 0.041(3) 0.035(3) 0.058(4) -0.008(3) 0.017(3) -0.002(3) N1 0.032(2) 0.043(3) 0.068(3) 0.001(2) 0.016(2) -0.001(2) N2 0.039(3) 0.050(3) 0.052(3) 0.008(2) 0.018(2) 0.009(2) N3 0.037(3) 0.046(3) 0.064(3) 0.007(2) 0.016(2) 0.009(2) N4 0.038(3) 0.039(3) 0.051(3) 0.004(2) 0.012(2) 0.001(2) O1 0.041(2) 0.056(3) 0.068(3) -0.018(2) 0.019(2) -0.016(2) O2 0.041(3) 0.058(3) 0.143(5) -0.041(3) 0.017(3) 0.001(2) O4 0.032(2) 0.052(3) 0.059(3) 0.009(2) 0.0106(17) 0.0094(19) O5 0.050(3) 0.088(4) 0.076(3) 0.024(3) 0.028(2) 0.010(3) O1W 0.071(6) 0.100(7) 0.079(6) 0.000 0.033(5) 0.000 N5 0.039(3) 0.048(3) 0.058(3) 0.001(2) 0.019(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.961(4) 2_645 ? Zn1 O1 1.988(4) . ? Zn1 N4 2.014(5) 7_655 ? Zn1 N1 2.031(5) . ? C1 N2 1.317(8) . ? C1 N1 1.345(8) . ? C1 H1 0.9300 . ? C2 C3 1.347(10) . ? C2 N1 1.371(8) . ? C2 H2 0.9300 . ? C3 N2 1.372(10) . ? C3 H3 0.9300 . ? C4 C5 1.493(10) . ? C4 N2 1.502(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.502(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.533(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.452(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.351(9) . ? C8 N3 1.353(9) . ? C8 H8 0.9300 . ? C9 N4 1.381(8) . ? C9 H9 0.9300 . ? C10 N4 1.308(8) . ? C10 N3 1.342(8) . ? C10 H10 0.9300 . ? C11 O2 1.227(7) . ? C11 O1 1.270(7) . ? C11 C12 1.503(8) . ? C12 C13 1.375(8) . ? C12 C17 1.400(9) . ? C13 C14 1.379(9) . ? C13 H13 0.9300 . ? C14 C15 1.385(8) . ? C14 H14 0.9300 . ? C15 C16 1.375(9) . ? C15 C18 1.512(9) . ? C16 C17 1.393(10) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N5 1.447(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N5 1.365(8) . ? C19 C20 1.397(8) . ? C19 C24 1.422(8) . ? C20 C21 1.374(11) . ? C20 H20 0.9300 . ? C21 C22 1.372(12) . ? C21 H21 0.9300 . ? C22 C23 1.394(11) . ? C22 H22 0.9300 . ? C23 C24 1.389(9) . ? C23 H23 0.9300 . ? C24 C25 1.492(8) . ? C25 O5 1.244(8) . ? C25 O4 1.264(8) . ? N4 Zn1 2.014(5) 7_655 ? O4 Zn1 1.961(4) 2_665 ? O1W H1WA 0.90(2) . ? O1W H1WB 0.89(2) . ? N5 H5N 0.87(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 O4 Zn1 O1 93.61(17) 2_645 . ? O4 Zn1 N4 117.3(2) 2_645 7_655 ? O1 Zn1 N4 124.0(2) . 7_655 ? O4 Zn1 N1 114.48(19) 2_645 . ? O1 Zn1 N1 102.1(2) . . ? N4 Zn1 N1 104.8(2) 7_655 . ? N2 C1 N1 111.3(6) . . ? N2 C1 H1 124.3 . . ? N1 C1 H1 124.3 . . ? C3 C2 N1 108.6(6) . . ? C3 C2 H2 125.7 . . ? N1 C2 H2 125.7 . . ? C2 C3 N2 107.6(6) . . ? C2 C3 H3 126.2 . . ? N2 C3 H3 126.2 . . ? C5 C4 N2 114.2(7) . . ? C5 C4 H4A 108.7 . . ? N2 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? N2 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 115.7(6) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.4 . . ? C5 C6 C7 110.6(6) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N3 C7 C6 113.1(6) . . ? N3 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N3 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 N3 107.6(6) . . ? C9 C8 H8 126.2 . . ? N3 C8 H8 126.2 . . ? C8 C9 N4 108.1(6) . . ? C8 C9 H9 126.0 . . ? N4 C9 H9 126.0 . . ? N4 C10 N3 111.3(6) . . ? N4 C10 H10 124.3 . . ? N3 C10 H10 124.3 . . ? O2 C11 O1 123.0(6) . . ? O2 C11 C12 119.1(5) . . ? O1 C11 C12 117.8(5) . . ? C13 C12 C17 118.2(6) . . ? C13 C12 C11 120.1(5) . . ? C17 C12 C11 121.5(5) . . ? C12 C13 C14 121.7(6) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C15 120.4(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 118.8(6) . . ? C16 C15 C18 119.2(6) . . ? C14 C15 C18 122.0(6) . . ? C15 C16 C17 121.0(6) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C12 119.9(6) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? N5 C18 C15 114.0(5) . . ? N5 C18 H18A 108.8 . . ? C15 C18 H18A 108.8 . . ? N5 C18 H18B 108.8 . . ? C15 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? N5 C19 C20 121.4(6) . . ? N5 C19 C24 120.8(5) . . ? C20 C19 C24 117.8(6) . . ? C21 C20 C19 121.8(7) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C22 C21 C20 121.2(7) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 118.0(7) . . ? C21 C22 H22 121.0 . . ? C23 C22 H22 121.0 . . ? C24 C23 C22 122.5(7) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C19 118.6(5) . . ? C23 C24 C25 117.3(6) . . ? C19 C24 C25 124.0(5) . . ? O5 C25 O4 122.4(6) . . ? O5 C25 C24 118.9(6) . . ? O4 C25 C24 118.6(5) . . ? C1 N1 C2 105.6(6) . . ? C1 N1 Zn1 126.3(4) . . ? C2 N1 Zn1 127.9(5) . . ? C1 N2 C3 106.9(5) . . ? C1 N2 C4 123.6(6) . . ? C3 N2 C4 129.1(6) . . ? C10 N3 C8 106.8(5) . . ? C10 N3 C7 126.6(6) . . ? C8 N3 C7 126.6(6) . . ? C10 N4 C9 106.1(5) . . ? C10 N4 Zn1 127.6(4) . 7_655 ? C9 N4 Zn1 125.9(4) . 7_655 ? C11 O1 Zn1 114.0(4) . . ? C25 O4 Zn1 113.5(4) . 2_665 ? H1WA O1W H1WB 107(3) . . ? C19 N5 C18 124.1(5) . . ? C19 N5 H5N 118(5) . . ? C18 N5 H5N 116(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -1.0(8) . . . . ? N2 C4 C5 C6 60.9(10) . . . . ? C4 C5 C6 C7 176.4(7) . . . . ? C5 C6 C7 N3 176.3(6) . . . . ? N3 C8 C9 N4 -1.8(8) . . . . ? O2 C11 C12 C13 -7.9(10) . . . . ? O1 C11 C12 C13 176.1(6) . . . . ? O2 C11 C12 C17 166.6(7) . . . . ? O1 C11 C12 C17 -9.4(9) . . . . ? C17 C12 C13 C14 1.9(10) . . . . ? C11 C12 C13 C14 176.6(6) . . . . ? C12 C13 C14 C15 -1.8(11) . . . . ? C13 C14 C15 C16 -1.1(10) . . . . ? C13 C14 C15 C18 -179.5(6) . . . . ? C14 C15 C16 C17 3.6(12) . . . . ? C18 C15 C16 C17 -177.9(7) . . . . ? C15 C16 C17 C12 -3.5(13) . . . . ? C13 C12 C17 C16 0.6(11) . . . . ? C11 C12 C17 C16 -174.0(7) . . . . ? C16 C15 C18 N5 68.0(9) . . . . ? C14 C15 C18 N5 -113.6(7) . . . . ? N5 C19 C20 C21 176.0(7) . . . . ? C24 C19 C20 C21 -1.7(10) . . . . ? C19 C20 C21 C22 0.1(12) . . . . ? C20 C21 C22 C23 1.5(13) . . . . ? C21 C22 C23 C24 -1.5(13) . . . . ? C22 C23 C24 C19 -0.1(11) . . . . ? C22 C23 C24 C25 178.3(7) . . . . ? N5 C19 C24 C23 -176.0(6) . . . . ? C20 C19 C24 C23 1.6(9) . . . . ? N5 C19 C24 C25 5.8(9) . . . . ? C20 C19 C24 C25 -176.6(6) . . . . ? C23 C24 C25 O5 -17.3(9) . . . . ? C19 C24 C25 O5 160.9(6) . . . . ? C23 C24 C25 O4 159.3(6) . . . . ? C19 C24 C25 O4 -22.5(9) . . . . ? N2 C1 N1 C2 0.9(7) . . . . ? N2 C1 N1 Zn1 -174.1(4) . . . . ? C3 C2 N1 C1 0.1(7) . . . . ? C3 C2 N1 Zn1 175.0(4) . . . . ? O4 Zn1 N1 C1 -65.9(5) 2_645 . . . ? O1 Zn1 N1 C1 -165.6(5) . . . . ? N4 Zn1 N1 C1 64.0(5) 7_655 . . . ? O4 Zn1 N1 C2 120.1(5) 2_645 . . . ? O1 Zn1 N1 C2 20.4(5) . . . . ? N4 Zn1 N1 C2 -109.9(5) 7_655 . . . ? N1 C1 N2 C3 -1.5(7) . . . . ? N1 C1 N2 C4 -175.7(5) . . . . ? C2 C3 N2 C1 1.5(7) . . . . ? C2 C3 N2 C4 175.3(6) . . . . ? C5 C4 N2 C1 -152.3(6) . . . . ? C5 C4 N2 C3 34.9(10) . . . . ? N4 C10 N3 C8 0.5(8) . . . . ? N4 C10 N3 C7 -179.3(6) . . . . ? C9 C8 N3 C10 0.8(8) . . . . ? C9 C8 N3 C7 -179.3(6) . . . . ? C6 C7 N3 C10 75.9(9) . . . . ? C6 C7 N3 C8 -103.9(8) . . . . ? N3 C10 N4 C9 -1.6(7) . . . . ? N3 C10 N4 Zn1 172.0(4) . . . 7_655 ? C8 C9 N4 C10 2.1(8) . . . . ? C8 C9 N4 Zn1 -171.6(5) . . . 7_655 ? O2 C11 O1 Zn1 -12.7(9) . . . . ? C12 C11 O1 Zn1 163.2(4) . . . . ? O4 Zn1 O1 C11 167.1(5) 2_645 . . . ? N4 Zn1 O1 C11 40.5(5) 7_655 . . . ? N1 Zn1 O1 C11 -76.9(5) . . . . ? O5 C25 O4 Zn1 9.2(8) . . . 2_665 ? C24 C25 O4 Zn1 -167.3(4) . . . 2_665 ? C20 C19 N5 C18 13.6(9) . . . . ? C24 C19 N5 C18 -168.9(6) . . . . ? C15 C18 N5 C19 71.7(8) . . . . ? 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 H1WA O1 0.90(2) 2.49(16) 2.978(6) 115(13) 2_665 O1W H1WB O1 0.89(2) 2.10(5) 2.978(6) 166(16) 1_565 N5 H5N O4 0.87(2) 2.05(5) 2.715(6) 132(6) . _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 67.05 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.944 _refine_diff_density_min -1.250 _refine_diff_density_rms 0.123 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 806747' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H52 Co2 N10 O9' _chemical_formula_weight 1054.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 20.8269(4) _cell_length_b 8.8702(2) _cell_length_c 26.6257(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.073(2) _cell_angle_gamma 90.00 _cell_volume 4810.00(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 5.970 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.28 _exptl_absorpt_correction_T_max 0.34 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12957 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 4.92 _diffrn_reflns_theta_max 67.79 _reflns_number_total 4237 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0866P)^2^+1.7102P] 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 4237 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Co1 Co 0.42821(3) 0.74701(7) 0.88008(2) 0.0596(2) Uani 1 1 d . . . C1 C 0.2985(2) 0.9101(4) 0.85501(16) 0.0623(9) Uani 1 1 d . . . H1 H 0.2792 0.8308 0.8344 0.075 Uiso 1 1 calc R A . C2 C 0.3680(2) 1.0484(5) 0.90450(17) 0.0732(11) Uani 1 1 d . . . H2 H 0.4068 1.0834 0.9250 0.088 Uiso 1 1 calc R A . C3 C 0.3109(2) 1.1236(5) 0.89454(18) 0.0754(12) Uani 1 1 d . A . H3 H 0.3031 1.2184 0.9070 0.091 Uiso 1 1 calc R . . C4 C 0.1989(2) 1.0760(5) 0.83820(17) 0.0755(12) Uani 1 1 d . . . H4A H 0.1940 1.0654 0.8013 0.091 Uiso 1 1 calc R A . H4B H 0.1915 1.1812 0.8452 0.091 Uiso 1 1 calc R . . C5 C 0.1470(2) 0.9827(6) 0.85508(16) 0.0788(12) Uani 1 1 d . A . H5A H 0.1542 0.8772 0.8484 0.095 Uiso 1 1 calc R . . H5B H 0.1042 1.0109 0.8351 0.095 Uiso 1 1 calc R . . C6 C 0.1474(2) 1.0028(6) 0.91125(16) 0.0795(13) Uani 1 1 d . . . H6A H 0.1471 1.1096 0.9192 0.095 Uiso 1 1 calc R A . H6B H 0.1872 0.9594 0.9315 0.095 Uiso 1 1 calc R . . C7 C 0.0878(2) 0.9273(7) 0.92557(17) 0.0863(14) Uani 1 1 d . A . H7A H 0.0481 0.9707 0.9050 0.104 Uiso 1 1 calc R . . H7B H 0.0882 0.8208 0.9174 0.104 Uiso 1 1 calc R . . C8 C 0.0804(2) 0.8349(6) 1.01254(16) 0.0751(12) Uani 1 1 d . A . H8 H 0.0769 0.7334 1.0036 0.090 Uiso 1 1 calc R . . C9 C 0.0854(2) 1.0375(6) 1.05492(19) 0.0803(12) Uani 1 1 d . A . H9 H 0.0865 1.1052 1.0818 0.096 Uiso 1 1 calc R . . C10 C 0.0888(2) 1.0756(6) 1.0062(2) 0.0832(13) Uani 1 1 d . A . H10 H 0.0923 1.1722 0.9935 0.100 Uiso 1 1 calc R . . C11 C 0.5358(2) 0.8908(6) 0.8984(2) 0.0819(14) Uani 1 1 d . . . C12 C 0.6041(2) 0.9547(5) 0.90433(16) 0.0661(10) Uani 1 1 d . A . C13 C 0.6360(3) 0.9977(6) 0.9526(2) 0.0904(15) Uani 1 1 d . . . H13 H 0.6148 0.9862 0.9798 0.109 Uiso 1 1 calc R A . C14 C 0.6981(4) 1.0571(7) 0.9620(2) 0.1108(19) Uani 1 1 d . A . H14 H 0.7183 1.0894 0.9948 0.133 Uiso 1 1 calc R . . C15 C 0.7300(3) 1.0676(6) 0.9214(2) 0.0992(16) Uani 1 1 d . . . H15 H 0.7726 1.1049 0.9273 0.119 Uiso 1 1 calc R A . C16 C 0.7003(2) 1.0245(5) 0.8731(2) 0.0783(12) Uani 1 1 d . A . H16 H 0.7225 1.0351 0.8465 0.094 Uiso 1 1 calc R . . C17 C 0.63681(19) 0.9646(4) 0.86306(16) 0.0607(9) Uani 1 1 d . . . C18 C 0.6367(3) 0.9257(5) 0.77034(18) 0.0780(12) Uani 1 1 d . . . H18A H 0.6151 0.8541 0.7447 0.094 Uiso 1 1 calc R A . H18B H 0.6827 0.8984 0.7798 0.094 Uiso 1 1 calc R . . C19 C 0.6308(2) 1.0814(5) 0.74711(15) 0.0622(10) Uani 1 1 d . A . C20 C 0.68434(19) 1.1720(5) 0.74763(15) 0.0630(10) Uani 1 1 d . . . H20 H 0.7262 1.1368 0.7621 0.076 Uiso 1 1 calc R A . C21 C 0.6766(2) 1.3145(5) 0.72686(16) 0.0674(10) Uani 1 1 d . A . H21 H 0.7134 1.3743 0.7276 0.081 Uiso 1 1 calc R . . C22 C 0.6161(2) 1.3698(5) 0.70532(14) 0.0615(10) Uani 1 1 d . . . C23 C 0.5628(2) 1.2781(6) 0.7036(2) 0.0902(15) Uani 1 1 d . A . H23 H 0.5210 1.3130 0.6888 0.108 Uiso 1 1 calc R . . C24 C 0.5705(2) 1.1361(7) 0.7236(2) 0.0908(15) Uani 1 1 d . . . H24 H 0.5338 1.0746 0.7211 0.109 Uiso 1 1 calc R A . N1 N 0.36024(15) 0.9119(3) 0.87982(12) 0.0587(8) Uani 1 1 d . A . N2 N 0.26696(16) 1.0363(3) 0.86310(12) 0.0608(8) Uani 1 1 d . A . N3 N 0.08623(16) 0.9445(5) 0.98003(13) 0.0706(9) Uani 1 1 d . . . N4 N 0.08004(17) 0.8854(4) 1.05850(13) 0.0697(9) Uani 1 1 d . . . O2 O 0.50542(19) 0.8444(5) 0.85608(18) 0.1086(13) Uani 1 1 d . A . N5 N 0.60778(19) 0.9147(4) 0.81538(15) 0.0728(10) Uani 1 1 d . A . H1N H 0.572(2) 0.884(6) 0.8098(19) 0.087 Uiso 1 1 d . . . O1W O 0.5000 0.7045(8) 0.7500 0.117(2) Uani 1 2 d S . . H1WA H 0.529(9) 0.63(2) 0.771(8) 0.175 Uiso 0.50 1 d P . . H1WB H 0.520(10) 0.64(2) 0.723(7) 0.175 Uiso 0.50 1 d P . . C25 C 0.5998(5) 1.5124(9) 0.6794(3) 0.058(2) Uani 0.626(14) 1 d P A 1 O3 O 0.5413(4) 1.5486(8) 0.6577(2) 0.076(2) Uani 0.626(14) 1 d P . 1 O4 O 0.6476(5) 1.6023(7) 0.6757(3) 0.089(3) Uani 0.626(14) 1 d P . 1 O1 O 0.5070(3) 0.8603(11) 0.9323(2) 0.081(2) Uani 0.626(14) 1 d P A 1 C25' C 0.6297(7) 1.5488(18) 0.6847(4) 0.040(3) Uiso 0.374(14) 1 d P A 2 O3' O 0.5716(6) 1.6012(14) 0.6732(4) 0.067(3) Uiso 0.374(14) 1 d P . 2 O4' O 0.6779(8) 1.6006(17) 0.6867(6) 0.106(6) Uiso 0.374(14) 1 d P A 2 O1' O 0.5188(7) 0.9342(17) 0.9450(5) 0.092(4) Uiso 0.374(14) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0581(3) 0.0603(4) 0.0644(3) 0.0009(3) 0.0219(2) 0.0052(3) C1 0.070(2) 0.043(2) 0.076(2) -0.0002(18) 0.0195(19) 0.0052(19) C2 0.076(3) 0.060(3) 0.085(3) -0.017(2) 0.022(2) -0.008(2) C3 0.086(3) 0.056(2) 0.089(3) -0.014(2) 0.029(2) 0.003(2) C4 0.078(3) 0.072(3) 0.082(3) 0.014(2) 0.028(2) 0.020(2) C5 0.072(3) 0.090(3) 0.072(2) 0.003(2) 0.011(2) 0.011(3) C6 0.071(3) 0.093(4) 0.072(2) 0.008(2) 0.010(2) -0.003(2) C7 0.079(3) 0.113(4) 0.068(2) 0.010(3) 0.018(2) 0.007(3) C8 0.087(3) 0.066(3) 0.075(3) 0.016(2) 0.023(2) 0.012(2) C9 0.089(3) 0.071(3) 0.085(3) 0.005(2) 0.028(2) 0.006(2) C10 0.094(3) 0.066(3) 0.095(3) 0.015(3) 0.033(3) 0.011(3) C11 0.084(3) 0.067(3) 0.109(4) 0.034(3) 0.053(3) 0.022(3) C12 0.077(2) 0.050(2) 0.076(2) 0.012(2) 0.025(2) 0.009(2) C13 0.107(4) 0.085(4) 0.084(3) 0.012(3) 0.031(3) 0.010(3) C14 0.131(5) 0.100(4) 0.091(4) 0.005(3) -0.001(4) 0.001(4) C15 0.083(3) 0.094(4) 0.115(4) 0.010(3) 0.007(3) -0.010(3) C16 0.070(3) 0.064(3) 0.105(3) 0.008(3) 0.028(3) -0.005(2) C17 0.067(2) 0.041(2) 0.079(2) 0.0053(19) 0.0264(19) 0.0028(18) C18 0.103(3) 0.054(3) 0.092(3) 0.001(2) 0.055(3) -0.003(2) C19 0.071(2) 0.054(2) 0.068(2) -0.0016(18) 0.0316(19) -0.0049(19) C20 0.058(2) 0.054(2) 0.081(2) 0.010(2) 0.0222(18) 0.0026(18) C21 0.069(2) 0.058(2) 0.078(2) 0.002(2) 0.023(2) -0.015(2) C22 0.079(3) 0.053(2) 0.057(2) 0.0041(17) 0.0235(19) 0.010(2) C23 0.066(3) 0.107(4) 0.098(3) 0.032(3) 0.017(2) 0.014(3) C24 0.070(3) 0.100(4) 0.103(3) 0.009(3) 0.018(3) -0.027(3) N1 0.0630(19) 0.0511(19) 0.0649(17) -0.0004(15) 0.0202(15) 0.0014(15) N2 0.0709(19) 0.0449(17) 0.0716(18) 0.0042(15) 0.0262(16) 0.0063(16) N3 0.0612(18) 0.082(3) 0.0705(19) 0.0127(19) 0.0178(15) 0.0085(18) N4 0.071(2) 0.071(2) 0.067(2) 0.0047(17) 0.0159(16) 0.0134(18) O2 0.103(3) 0.100(3) 0.146(3) -0.043(3) 0.079(3) -0.040(2) N5 0.078(2) 0.063(2) 0.086(2) 0.0050(19) 0.038(2) -0.0151(19) O1W 0.142(5) 0.123(5) 0.097(4) 0.000 0.052(4) 0.000 C25 0.064(5) 0.046(5) 0.068(4) -0.006(3) 0.026(3) -0.004(4) O3 0.074(4) 0.082(4) 0.071(3) 0.006(3) 0.015(3) 0.017(3) O4 0.119(7) 0.045(3) 0.092(4) 0.022(3) -0.002(4) -0.034(3) O1 0.073(3) 0.109(6) 0.066(3) 0.012(3) 0.024(2) -0.023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3' 1.920(9) 2_646 ? Co1 N1 2.035(3) . ? Co1 O2 2.042(3) . ? Co1 N4 2.050(4) 7_567 ? Co1 O1 2.163(8) . ? Co1 O3 2.186(7) 2_646 ? Co1 O4 2.316(8) 2_646 ? C1 N1 1.317(5) . ? C1 N2 1.338(5) . ? C1 H1 0.9300 . ? C2 C3 1.340(6) . ? C2 N1 1.371(5) . ? C2 H2 0.9300 . ? C3 N2 1.349(6) . ? C3 H3 0.9300 . ? C4 N2 1.477(5) . ? C4 C5 1.502(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.505(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.465(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.305(5) . ? C8 N3 1.324(5) . ? C8 H8 0.9300 . ? C9 C10 1.356(7) . ? C9 N4 1.359(6) . ? C9 H9 0.9300 . ? C10 N3 1.351(6) . ? C10 H10 0.9300 . ? C11 O1 1.215(6) . ? C11 O2 1.243(7) . ? C11 O1' 1.413(13) . ? C11 C12 1.507(7) . ? C12 C13 1.372(7) . ? C12 C17 1.412(5) . ? C13 C14 1.372(8) . ? C13 H13 0.9300 . ? C14 C15 1.386(8) . ? C14 H14 0.9300 . ? C15 C16 1.359(7) . ? C15 H15 0.9300 . ? C16 C17 1.399(6) . ? C16 H16 0.9300 . ? C17 N5 1.361(6) . ? C18 N5 1.453(5) . ? C18 C19 1.508(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C24 1.370(7) . ? C19 C20 1.371(5) . ? C20 C21 1.376(6) . ? C20 H20 0.9300 . ? C21 C22 1.361(6) . ? C21 H21 0.9300 . ? C22 C23 1.370(6) . ? C22 C25 1.447(9) . ? C22 C25' 1.722(18) . ? C23 C24 1.364(7) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? N4 Co1 2.050(4) 7_567 ? N5 H1N 0.78(5) . ? O1W H1WA 1.01(16) . ? O1W H1WB 1.08(16) . ? C25 O3 1.276(11) . ? C25 O4 1.295(11) . ? O3 Co1 2.186(7) 2_666 ? O4 Co1 2.316(8) 2_666 ? C25' O4' 1.10(2) . ? C25' O3' 1.273(17) . ? O3' Co1 1.920(9) 2_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 O3' Co1 N1 126.2(4) 2_646 . ? O3' Co1 O2 86.0(3) 2_646 . ? N1 Co1 O2 106.72(15) . . ? O3' Co1 N4 102.5(4) 2_646 7_567 ? N1 Co1 N4 103.90(13) . 7_567 ? O2 Co1 N4 134.03(18) . 7_567 ? O3' Co1 O1 132.0(4) 2_646 . ? N1 Co1 O1 95.8(2) . . ? O2 Co1 O1 57.59(17) . . ? N4 Co1 O1 86.11(18) 7_567 . ? O3' Co1 O3 21.9(3) 2_646 2_646 ? N1 Co1 O3 147.8(2) . 2_646 ? O2 Co1 O3 82.71(17) . 2_646 ? N4 Co1 O3 89.2(2) 7_567 2_646 ? O1 Co1 O3 114.5(3) . 2_646 ? O3' Co1 O4 42.2(4) 2_646 2_646 ? N1 Co1 O4 90.9(2) . 2_646 ? O2 Co1 O4 120.6(3) . 2_646 ? N4 Co1 O4 91.9(2) 7_567 2_646 ? O1 Co1 O4 173.2(3) . 2_646 ? O3 Co1 O4 58.9(3) 2_646 2_646 ? N1 C1 N2 111.7(4) . . ? N1 C1 H1 124.2 . . ? N2 C1 H1 124.2 . . ? C3 C2 N1 109.6(4) . . ? C3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? C2 C3 N2 107.2(4) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 C5 114.7(4) . . ? N2 C4 H4A 108.6 . . ? C5 C4 H4A 108.6 . . ? N2 C4 H4B 108.6 . . ? C5 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 112.2(4) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 111.1(4) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N3 C7 C6 112.9(4) . . ? N3 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N3 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N4 C8 N3 112.4(4) . . ? N4 C8 H8 123.8 . . ? N3 C8 H8 123.8 . . ? C10 C9 N4 109.6(5) . . ? C10 C9 H9 125.2 . . ? N4 C9 H9 125.2 . . ? N3 C10 C9 105.9(4) . . ? N3 C10 H10 127.0 . . ? C9 C10 H10 127.0 . . ? O1 C11 O2 111.2(6) . . ? O2 C11 O1' 135.4(7) . . ? O1 C11 C12 127.5(6) . . ? O2 C11 C12 120.6(4) . . ? O1' C11 C12 102.2(8) . . ? C13 C12 C17 119.6(4) . . ? C13 C12 C11 117.6(4) . . ? C17 C12 C11 122.7(4) . . ? C14 C13 C12 122.1(5) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 118.1(6) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? C16 C15 C14 121.5(5) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 120.9(5) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? N5 C17 C16 121.4(4) . . ? N5 C17 C12 120.9(4) . . ? C16 C17 C12 117.8(4) . . ? N5 C18 C19 112.9(4) . . ? N5 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? N5 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C24 C19 C20 117.5(4) . . ? C24 C19 C18 120.0(4) . . ? C20 C19 C18 122.5(4) . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 121.4(4) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C21 C22 C23 118.2(4) . . ? C21 C22 C25 128.4(6) . . ? C23 C22 C25 113.3(6) . . ? C21 C22 C25' 105.5(6) . . ? C23 C22 C25' 136.3(6) . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C19 121.9(4) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.1 . . ? C1 N1 C2 104.8(3) . . ? C1 N1 Co1 126.7(3) . . ? C2 N1 Co1 128.4(3) . . ? C1 N2 C3 106.7(3) . . ? C1 N2 C4 125.8(4) . . ? C3 N2 C4 127.2(4) . . ? C8 N3 C10 107.1(4) . . ? C8 N3 C7 126.5(4) . . ? C10 N3 C7 126.4(4) . . ? C8 N4 C9 105.0(4) . . ? C8 N4 Co1 124.7(3) . 7_567 ? C9 N4 Co1 130.3(3) . 7_567 ? C11 O2 Co1 98.1(3) . . ? C17 N5 C18 124.6(4) . . ? C17 N5 H1N 121(4) . . ? C18 N5 H1N 114(4) . . ? H1WA O1W H1WB 73(10) . . ? O3 C25 O4 119.1(7) . . ? O3 C25 C22 122.9(7) . . ? O4 C25 C22 117.8(8) . . ? C25 O3 Co1 94.0(5) . 2_666 ? C25 O4 Co1 87.6(6) . 2_666 ? C11 O1 Co1 93.0(5) . . ? O4' C25' O3' 132.4(18) . . ? O4' C25' C22 125.6(12) . . ? O3' C25' C22 101.7(12) . . ? C25' O3' Co1 106.0(9) . 2_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 N1 C2 C3 N2 -0.7(5) . . . . ? N2 C4 C5 C6 63.1(5) . . . . ? C4 C5 C6 C7 170.9(4) . . . . ? C5 C6 C7 N3 -179.9(4) . . . . ? N4 C9 C10 N3 -0.6(6) . . . . ? O1 C11 C12 C13 -6.7(9) . . . . ? O2 C11 C12 C13 -177.2(5) . . . . ? O1' C11 C12 C13 15.6(7) . . . . ? O1 C11 C12 C17 170.1(7) . . . . ? O2 C11 C12 C17 -0.4(7) . . . . ? O1' C11 C12 C17 -167.6(6) . . . . ? C17 C12 C13 C14 3.1(8) . . . . ? C11 C12 C13 C14 180.0(5) . . . . ? C12 C13 C14 C15 -2.6(9) . . . . ? C13 C14 C15 C16 1.8(9) . . . . ? C14 C15 C16 C17 -1.5(8) . . . . ? C15 C16 C17 N5 -176.9(4) . . . . ? C15 C16 C17 C12 1.9(7) . . . . ? C13 C12 C17 N5 176.2(4) . . . . ? C11 C12 C17 N5 -0.6(6) . . . . ? C13 C12 C17 C16 -2.6(6) . . . . ? C11 C12 C17 C16 -179.4(4) . . . . ? N5 C18 C19 C24 -68.7(6) . . . . ? N5 C18 C19 C20 112.5(5) . . . . ? C24 C19 C20 C21 2.5(6) . . . . ? C18 C19 C20 C21 -178.7(4) . . . . ? C19 C20 C21 C22 0.0(6) . . . . ? C20 C21 C22 C23 -1.6(7) . . . . ? C20 C21 C22 C25 -176.1(5) . . . . ? C20 C21 C22 C25' -180.0(5) . . . . ? C21 C22 C23 C24 0.7(7) . . . . ? C25 C22 C23 C24 176.0(5) . . . . ? C25' C22 C23 C24 178.4(6) . . . . ? C22 C23 C24 C19 1.9(8) . . . . ? C20 C19 C24 C23 -3.4(7) . . . . ? C18 C19 C24 C23 177.7(4) . . . . ? N2 C1 N1 C2 -0.7(4) . . . . ? N2 C1 N1 Co1 179.8(2) . . . . ? C3 C2 N1 C1 0.8(5) . . . . ? C3 C2 N1 Co1 -179.7(3) . . . . ? O3' Co1 N1 C1 26.3(5) 2_646 . . . ? O2 Co1 N1 C1 123.7(3) . . . . ? N4 Co1 N1 C1 -91.0(3) 7_567 . . . ? O1 Co1 N1 C1 -178.4(3) . . . . ? O3 Co1 N1 C1 20.5(5) 2_646 . . . ? O4 Co1 N1 C1 1.2(4) 2_646 . . . ? O3' Co1 N1 C2 -153.1(5) 2_646 . . . ? O2 Co1 N1 C2 -55.6(4) . . . . ? N4 Co1 N1 C2 89.6(3) 7_567 . . . ? O1 Co1 N1 C2 2.2(4) . . . . ? O3 Co1 N1 C2 -158.8(4) 2_646 . . . ? O4 Co1 N1 C2 -178.1(4) 2_646 . . . ? N1 C1 N2 C3 0.3(5) . . . . ? N1 C1 N2 C4 175.2(4) . . . . ? C2 C3 N2 C1 0.2(5) . . . . ? C2 C3 N2 C4 -174.6(4) . . . . ? C5 C4 N2 C1 70.3(5) . . . . ? C5 C4 N2 C3 -115.9(5) . . . . ? N4 C8 N3 C10 -1.0(5) . . . . ? N4 C8 N3 C7 -179.5(4) . . . . ? C9 C10 N3 C8 1.0(5) . . . . ? C9 C10 N3 C7 179.5(4) . . . . ? C6 C7 N3 C8 -126.9(5) . . . . ? C6 C7 N3 C10 54.9(6) . . . . ? N3 C8 N4 C9 0.6(5) . . . . ? N3 C8 N4 Co1 179.9(3) . . . 7_567 ? C10 C9 N4 C8 0.1(6) . . . . ? C10 C9 N4 Co1 -179.2(3) . . . 7_567 ? O1 C11 O2 Co1 -0.8(6) . . . . ? O1' C11 O2 Co1 -26.9(10) . . . . ? C12 C11 O2 Co1 171.1(3) . . . . ? O3' Co1 O2 C11 -146.6(5) 2_646 . . . ? N1 Co1 O2 C11 86.8(4) . . . . ? N4 Co1 O2 C11 -43.0(4) 7_567 . . . ? O1 Co1 O2 C11 0.5(4) . . . . ? O3 Co1 O2 C11 -124.7(4) 2_646 . . . ? O4 Co1 O2 C11 -171.8(3) 2_646 . . . ? C16 C17 N5 C18 -3.7(7) . . . . ? C12 C17 N5 C18 177.5(4) . . . . ? C19 C18 N5 C17 -78.3(6) . . . . ? C21 C22 C25 O3 175.3(5) . . . . ? C23 C22 C25 O3 0.5(8) . . . . ? C25' C22 C25 O3 -175.2(17) . . . . ? C21 C22 C25 O4 -0.2(9) . . . . ? C23 C22 C25 O4 -175.0(6) . . . . ? C25' C22 C25 O4 9.2(11) . . . . ? O4 C25 O3 Co1 6.1(7) . . . 2_666 ? C22 C25 O3 Co1 -169.4(5) . . . 2_666 ? O3 C25 O4 Co1 -5.7(7) . . . 2_666 ? C22 C25 O4 Co1 170.0(5) . . . 2_666 ? O2 C11 O1 Co1 0.8(6) . . . . ? O1' C11 O1 Co1 145.5(13) . . . . ? C12 C11 O1 Co1 -170.4(4) . . . . ? O3' Co1 O1 C11 46.4(9) 2_646 . . . ? N1 Co1 O1 C11 -106.6(5) . . . . ? O2 Co1 O1 C11 -0.5(4) . . . . ? N4 Co1 O1 C11 149.8(5) 7_567 . . . ? O3 Co1 O1 C11 62.4(6) 2_646 . . . ? C21 C22 C25' O4' 3.8(15) . . . . ? C23 C22 C25' O4' -174.1(12) . . . . ? C25 C22 C25' O4' -168(2) . . . . ? C21 C22 C25' O3' -169.6(7) . . . . ? C23 C22 C25' O3' 12.4(11) . . . . ? C25 C22 C25' O3' 18.1(10) . . . . ? O4' C25' O3' Co1 36(2) . . . 2_666 ? C22 C25' O3' Co1 -151.4(6) . . . 2_666 ? 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 N5 H1N O2 0.78(5) 2.07(5) 2.660(5) 133(5) . O1W H1WB O3' 1.08(16) 1.90(15) 2.919(10) 156(15) 1_545 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 67.79 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.297 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.050 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 806748' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H52 Cd2 N10 O9' _chemical_formula_weight 1161.84 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 C2/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 21.332(1) _cell_length_b 8.884(3) _cell_length_c 26.584(6) _cell_angle_alpha 90.000 _cell_angle_beta 103.110(4) _cell_angle_gamma 90.000 _cell_volume 4907(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2360 _exptl_absorpt_coefficient_mu 0.934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.79 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19564 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 29.20 _reflns_number_total 5896 _reflns_number_gt 3149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A. The distance of H1WA...HW1B was restrained to 1.44+-0.02 \%A. For C7 and O1 atoms, some anisotropic displacement ellipsoids were rather elongated which led us to use the ISOR restraints. For O1, O2 and C15 atoms, SIMU restraint was used to make them behave similar anisotropic displacement parameters. ; _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^)+(0.0647P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5896 _refine_ls_number_parameters 330 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd -0.065429(14) -0.29030(4) 0.886218(13) 0.05916(15) Uani 1 1 d . . . C1 C 0.1082(3) -1.0531(6) 0.68142(19) 0.0677(13) Uani 1 1 d . . . C2 C 0.11652(19) -0.9001(5) 0.70513(16) 0.0535(11) Uani 1 1 d . . . C3 C 0.1767(2) -0.8430(5) 0.7236(2) 0.0635(12) Uani 1 1 d . . . H3 H 0.2125 -0.9012 0.7222 0.076 Uiso 1 1 calc R . . C4 C 0.1852(2) -0.6997(5) 0.7442(2) 0.0653(13) Uani 1 1 d . . . H4 H 0.2267 -0.6632 0.7568 0.078 Uiso 1 1 calc R . . C5 C 0.1334(2) -0.6104(5) 0.74658(18) 0.0585(11) Uani 1 1 d . . . C6 C 0.0735(2) -0.6655(6) 0.7263(2) 0.0896(18) Uani 1 1 d . . . H6 H 0.0377 -0.6054 0.7261 0.107 Uiso 1 1 calc R . . C7 C 0.0648(3) -0.8077(6) 0.7061(2) 0.0821(15) Uani 1 1 d U . . H7 H 0.0233 -0.8427 0.6927 0.099 Uiso 1 1 calc R . . C8 C 0.1397(2) -0.4550(5) 0.7694(2) 0.0704(13) Uani 1 1 d . . . H8A H 0.1847 -0.4259 0.7770 0.085 Uiso 1 1 calc R . . H8B H 0.1163 -0.3849 0.7439 0.085 Uiso 1 1 calc R . . C9 C 0.14693(19) -0.4907(4) 0.86361(19) 0.0510(11) Uani 1 1 d . . . C10 C 0.2097(2) -0.5492(5) 0.8715(2) 0.0696(14) Uani 1 1 d . . . H10 H 0.2288 -0.5607 0.8435 0.083 Uiso 1 1 calc R . . C11 C 0.2430(3) -0.5894(6) 0.9199(3) 0.0866(18) Uani 1 1 d . . . H11 H 0.2838 -0.6309 0.9240 0.104 Uiso 1 1 calc R . . C12 C 0.2182(3) -0.5704(7) 0.9619(3) 0.093(2) Uani 1 1 d . . . H12 H 0.2422 -0.5941 0.9947 0.111 Uiso 1 1 calc R . . C13 C 0.1558(3) -0.5147(5) 0.9551(2) 0.0764(15) Uani 1 1 d . . . H13 H 0.1383 -0.5020 0.9839 0.092 Uiso 1 1 calc R . . C14 C 0.11925(19) -0.4779(4) 0.90715(18) 0.0522(11) Uani 1 1 d . . . C15 C 0.0523(2) -0.4241(5) 0.9018(2) 0.0612(11) Uani 1 1 d U . . C16 C -0.0726(2) -0.1850(5) 0.9995(2) 0.0688(13) Uani 1 1 d . . . H16 H -0.0664 -0.2842 1.0107 0.083 Uiso 1 1 calc R . . C17 C -0.0825(2) 0.0101(5) 0.9533(2) 0.0667(13) Uani 1 1 d . . . H17 H -0.0848 0.0736 0.9251 0.080 Uiso 1 1 calc R . . C18 C -0.0866(2) 0.0535(6) 1.0004(2) 0.0744(14) Uani 1 1 d . . . H18 H -0.0925 0.1514 1.0108 0.089 Uiso 1 1 calc R . . C19 C -0.0812(3) -0.0770(7) 1.0846(2) 0.0967(19) Uani 1 1 d . . . H19A H -0.0426 -0.0294 1.1047 0.116 Uiso 1 1 calc R . . H19B H -0.0811 -0.1813 1.0954 0.116 Uiso 1 1 calc R . . C20 C -0.1448(3) 0.0083(8) 1.0957(2) 0.0978(19) Uani 1 1 d . . . H20A H -0.1444 0.1133 1.0858 0.117 Uiso 1 1 calc R . . H20B H -0.1835 -0.0377 1.0751 0.117 Uiso 1 1 calc R . . C21 C -0.1452(3) -0.0028(8) 1.1494(3) 0.103(2) Uani 1 1 d . . . H21A H -0.1034 0.0262 1.1701 0.124 Uiso 1 1 calc R . . H21B H -0.1534 -0.1061 1.1578 0.124 Uiso 1 1 calc R . . C22 C -0.1958(3) 0.0971(6) 1.1616(3) 0.0876(17) Uani 1 1 d . . . H22A H -0.1929 0.0920 1.1985 0.105 Uiso 1 1 calc R . . H22B H -0.1858 0.1998 1.1537 0.105 Uiso 1 1 calc R . . C23 C -0.2975(2) -0.0531(5) 1.1423(2) 0.0626(12) Uani 1 1 d . . . H23 H -0.2814 -0.1348 1.1631 0.075 Uiso 1 1 calc R . . N4 N -0.35722(17) -0.0418(4) 1.11648(15) 0.0576(9) Uani 1 1 d . . . C25 C -0.3030(3) 0.1591(6) 1.1026(2) 0.0804(16) Uani 1 1 d . . . H25 H -0.2928 0.2518 1.0903 0.096 Uiso 1 1 calc R . . N1 N -0.07456(16) -0.1422(4) 0.95295(16) 0.0597(9) Uani 1 1 d . . . N2 N -0.08061(18) -0.0703(5) 1.02999(17) 0.0670(11) Uani 1 1 d . . . N3 N -0.26221(19) 0.0668(4) 1.13535(17) 0.0653(10) Uani 1 1 d . . . C24 C -0.3604(3) 0.0919(6) 1.0914(2) 0.0790(15) Uani 1 1 d . . . H24 H -0.3972 0.1310 1.0696 0.095 Uiso 1 1 calc R . . O1 O 0.0311(2) -0.4074(5) 0.94168(18) 0.1014(12) Uani 1 1 d U . . O2 O 0.01740(15) -0.3922(4) 0.85916(14) 0.0786(10) Uani 1 1 d U . . O3 O 0.15401(17) -1.1300(4) 0.67745(15) 0.0811(10) Uani 1 1 d . . . O4 O 0.04970(17) -1.0952(4) 0.66379(16) 0.0890(11) Uani 1 1 d . . . O1W O 0.0000 -1.2467(8) 0.7500 0.114(2) Uani 1 2 d SD . . H1WB H 0.013(10) -1.179(17) 0.732(5) 0.171 Uiso 0.50 1 d PD . . H1WA H -0.001(11) -1.216(17) 0.780(3) 0.171 Uiso 0.50 1 d PD . . N5 N 0.11579(19) -0.4427(4) 0.81626(17) 0.0619(10) Uani 1 1 d . . . H5N H 0.079(2) -0.420(5) 0.813(2) 0.074 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0514(2) 0.0668(2) 0.0653(3) -0.00158(18) 0.02578(15) 0.00173(16) C1 0.076(3) 0.078(3) 0.056(3) -0.004(3) 0.028(3) -0.017(3) C2 0.049(2) 0.068(3) 0.046(3) -0.001(2) 0.0164(19) 0.004(2) C3 0.048(2) 0.065(3) 0.081(4) -0.005(3) 0.022(2) 0.010(2) C4 0.048(2) 0.069(3) 0.084(4) -0.008(3) 0.027(2) -0.007(2) C5 0.059(3) 0.061(3) 0.063(3) 0.000(2) 0.031(2) 0.001(2) C6 0.061(3) 0.095(4) 0.114(5) -0.028(4) 0.020(3) 0.021(3) C7 0.0796(17) 0.0838(18) 0.0829(18) -0.0041(10) 0.0184(10) 0.0007(10) C8 0.076(3) 0.069(3) 0.078(4) 0.002(3) 0.043(3) 0.008(2) C9 0.051(2) 0.038(2) 0.066(3) -0.007(2) 0.017(2) -0.0012(18) C10 0.055(3) 0.063(3) 0.093(4) -0.003(3) 0.021(3) 0.013(2) C11 0.057(3) 0.075(4) 0.121(6) -0.004(4) 0.005(4) 0.008(3) C12 0.081(4) 0.091(4) 0.086(5) -0.002(3) -0.022(4) 0.011(3) C13 0.086(4) 0.074(3) 0.064(4) -0.008(3) 0.006(3) -0.004(3) C14 0.049(2) 0.044(2) 0.062(3) -0.008(2) 0.009(2) -0.0020(18) C15 0.066(3) 0.072(3) 0.055(3) -0.015(2) 0.033(2) -0.007(2) C16 0.077(3) 0.057(3) 0.078(4) -0.004(3) 0.030(3) -0.006(2) C17 0.071(3) 0.063(3) 0.072(4) 0.001(3) 0.030(3) 0.003(2) C18 0.072(3) 0.063(3) 0.096(4) -0.013(3) 0.037(3) -0.008(2) C19 0.117(5) 0.098(4) 0.084(5) -0.009(3) 0.042(4) -0.029(4) C20 0.100(4) 0.122(5) 0.069(4) -0.016(4) 0.015(3) 0.006(4) C21 0.099(4) 0.119(5) 0.088(5) -0.010(4) 0.013(4) -0.024(4) C22 0.073(3) 0.076(3) 0.122(5) -0.002(3) 0.040(3) -0.015(3) C23 0.071(3) 0.045(2) 0.081(4) 0.005(2) 0.036(3) -0.001(2) N4 0.057(2) 0.054(2) 0.067(3) -0.0024(19) 0.0255(19) 0.0009(17) C25 0.103(4) 0.056(3) 0.090(4) 0.014(3) 0.037(3) -0.002(3) N1 0.057(2) 0.061(2) 0.065(3) -0.006(2) 0.0217(19) -0.0038(18) N2 0.071(2) 0.069(3) 0.068(3) -0.008(2) 0.032(2) -0.0114(19) N3 0.073(2) 0.054(2) 0.078(3) -0.002(2) 0.036(2) -0.006(2) C24 0.085(4) 0.063(3) 0.089(4) 0.013(3) 0.021(3) 0.007(3) O1 0.1003(14) 0.1063(15) 0.0989(15) -0.0024(10) 0.0253(10) 0.0056(9) O2 0.0604(18) 0.117(3) 0.065(2) 0.009(2) 0.0267(17) 0.0265(18) O3 0.078(2) 0.070(2) 0.098(3) -0.017(2) 0.025(2) 0.0058(19) O4 0.078(2) 0.101(3) 0.096(3) -0.032(2) 0.034(2) -0.030(2) O1W 0.141(6) 0.130(6) 0.086(5) 0.000 0.056(5) 0.000 N5 0.060(2) 0.069(2) 0.065(3) 0.001(2) 0.032(2) 0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N4 2.213(4) 7_447 y Cd1 O2 2.244(3) . y Cd1 N1 2.252(4) . y Cd1 O4 2.255(4) 2_566 y Cd1 O1 2.474(4) . y Cd1 O3 2.648(3) 2_566 y Cd1 C15 2.724(5) . y C1 O3 1.217(6) . ? C1 O4 1.285(6) . ? C1 C2 1.491(7) . ? C2 C3 1.363(6) . ? C2 C7 1.379(7) . ? C3 C4 1.383(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(6) . ? C4 H4 0.9300 . ? C5 C6 1.361(7) . ? C5 C8 1.502(7) . ? C6 C7 1.368(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N5 1.455(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N5 1.352(6) . ? C9 C10 1.407(6) . ? C9 C14 1.418(6) . ? C10 C11 1.369(8) . ? C10 H10 0.9300 . ? C11 C12 1.349(8) . ? C11 H11 0.9300 . ? C12 C13 1.393(8) . ? C12 H12 0.9300 . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C14 C15 1.482(6) . ? C15 O2 1.239(6) . ? C15 O1 1.253(6) . ? C16 N1 1.286(6) . ? C16 N2 1.336(6) . ? C16 H16 0.9300 . ? C17 C18 1.331(7) . ? C17 N1 1.365(6) . ? C17 H17 0.9300 . ? C18 N2 1.342(6) . ? C18 H18 0.9300 . ? C19 N2 1.456(7) . ? C19 C20 1.639(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.433(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.489(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N3 1.455(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N4 1.307(6) . ? C23 N3 1.341(6) . ? C23 H23 0.9300 . ? N4 C24 1.357(6) . ? N4 Cd1 2.213(4) 7_447 ? C25 C24 1.334(7) . ? C25 N3 1.358(6) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? O3 Cd1 2.648(3) 2_546 ? O4 Cd1 2.255(4) 2_546 ? O1W H1WB 0.86(2) . ? O1W H1WA 0.86(2) . ? N5 H5N 0.80(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cd1 O2 110.68(14) 7_447 . y N4 Cd1 N1 102.83(14) 7_447 . y O2 Cd1 N1 134.69(13) . . y N4 Cd1 O4 135.10(14) 7_447 2_566 y O2 Cd1 O4 83.56(14) . 2_566 y N1 Cd1 O4 93.81(16) . 2_566 y N4 Cd1 O1 104.44(14) 7_447 . y O2 Cd1 O1 53.98(14) . . y N1 Cd1 O1 89.15(14) . . y O4 Cd1 O1 117.37(14) 2_566 . y N4 Cd1 O3 85.58(13) 7_447 2_566 y O2 Cd1 O3 120.77(13) . 2_566 y N1 Cd1 O3 90.73(13) . 2_566 y O4 Cd1 O3 52.41(12) 2_566 2_566 y O1 Cd1 O3 169.74(13) . 2_566 y N4 Cd1 C15 111.45(14) 7_447 . y O2 Cd1 C15 26.73(12) . . y N1 Cd1 C15 112.13(14) . . y O4 Cd1 C15 99.77(14) 2_566 . y O1 Cd1 C15 27.35(14) . . y O3 Cd1 C15 146.25(14) 2_566 . y O3 C1 O4 122.5(5) . . ? O3 C1 C2 121.9(4) . . ? O4 C1 C2 115.6(5) . . ? C3 C2 C7 117.6(4) . . ? C3 C2 C1 120.2(4) . . ? C7 C2 C1 122.1(4) . . ? C2 C3 C4 120.9(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 117.9(4) . . ? C6 C5 C8 118.8(4) . . ? C4 C5 C8 123.3(4) . . ? C5 C6 C7 121.3(5) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C2 121.3(5) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? N5 C8 C5 113.4(4) . . ? N5 C8 H8A 108.9 . . ? C5 C8 H8A 108.9 . . ? N5 C8 H8B 108.9 . . ? C5 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N5 C9 C10 120.3(5) . . ? N5 C9 C14 121.8(4) . . ? C10 C9 C14 117.8(4) . . ? C11 C10 C9 120.6(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 121.9(5) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 118.7(5) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 121.9(6) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C9 119.0(4) . . ? C13 C14 C15 119.8(5) . . ? C9 C14 C15 121.2(4) . . ? O2 C15 O1 119.3(5) . . ? O2 C15 C14 121.8(4) . . ? O1 C15 C14 118.8(5) . . ? O2 C15 Cd1 54.5(2) . . ? O1 C15 Cd1 65.1(3) . . ? C14 C15 Cd1 172.1(3) . . ? N1 C16 N2 112.2(4) . . ? N1 C16 H16 123.9 . . ? N2 C16 H16 123.9 . . ? C18 C17 N1 109.1(5) . . ? C18 C17 H17 125.4 . . ? N1 C17 H17 125.4 . . ? C17 C18 N2 107.3(5) . . ? C17 C18 H18 126.4 . . ? N2 C18 H18 126.4 . . ? N2 C19 C20 110.8(5) . . ? N2 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C19 109.8(5) . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 C22 110.0(6) . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? N3 C22 C21 117.4(5) . . ? N3 C22 H22A 107.9 . . ? C21 C22 H22A 107.9 . . ? N3 C22 H22B 107.9 . . ? C21 C22 H22B 107.9 . . ? H22A C22 H22B 107.2 . . ? N4 C23 N3 112.2(4) . . ? N4 C23 H23 123.9 . . ? N3 C23 H23 123.9 . . ? C23 N4 C24 105.1(4) . . ? C23 N4 Cd1 126.6(3) . 7_447 ? C24 N4 Cd1 128.3(3) . 7_447 ? C24 C25 N3 107.2(4) . . ? C24 C25 H25 126.4 . . ? N3 C25 H25 126.4 . . ? C16 N1 C17 105.3(4) . . ? C16 N1 Cd1 126.6(3) . . ? C17 N1 Cd1 128.1(4) . . ? C16 N2 C18 106.1(5) . . ? C16 N2 C19 127.2(5) . . ? C18 N2 C19 126.7(5) . . ? C23 N3 C25 105.7(4) . . ? C23 N3 C22 126.7(4) . . ? C25 N3 C22 127.4(4) . . ? C25 C24 N4 109.9(5) . . ? C25 C24 H24 125.0 . . ? N4 C24 H24 125.0 . . ? C15 O1 Cd1 87.5(3) . . ? C15 O2 Cd1 98.8(3) . . ? C1 O3 Cd1 83.5(3) . 2_546 ? C1 O4 Cd1 100.2(3) . 2_546 ? H1WB O1W H1WA 113(4) . . ? C9 N5 C8 125.5(4) . . ? C9 N5 H5N 117(4) . . ? C8 N5 H5N 117(4) . . ? 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 O3 C1 C2 C3 -0.6(7) . . . . ? O4 C1 C2 C3 -178.0(4) . . . . ? O3 C1 C2 C7 174.8(5) . . . . ? O4 C1 C2 C7 -2.6(7) . . . . ? C7 C2 C3 C4 2.5(7) . . . . ? C1 C2 C3 C4 178.1(5) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 -2.2(8) . . . . ? C3 C4 C5 C8 179.0(5) . . . . ? C4 C5 C6 C7 2.7(9) . . . . ? C8 C5 C6 C7 -178.5(5) . . . . ? C5 C6 C7 C2 -0.6(10) . . . . ? C3 C2 C7 C6 -2.0(8) . . . . ? C1 C2 C7 C6 -177.5(5) . . . . ? C6 C5 C8 N5 67.7(6) . . . . ? C4 C5 C8 N5 -113.5(5) . . . . ? N5 C9 C10 C11 176.0(4) . . . . ? C14 C9 C10 C11 -1.2(6) . . . . ? C9 C10 C11 C12 -2.1(8) . . . . ? C10 C11 C12 C13 3.0(9) . . . . ? C11 C12 C13 C14 -0.4(8) . . . . ? C12 C13 C14 C9 -2.9(7) . . . . ? C12 C13 C14 C15 177.8(5) . . . . ? N5 C9 C14 C13 -173.6(4) . . . . ? C10 C9 C14 C13 3.6(6) . . . . ? N5 C9 C14 C15 5.7(6) . . . . ? C10 C9 C14 C15 -177.1(4) . . . . ? C13 C14 C15 O2 -178.7(4) . . . . ? C9 C14 C15 O2 2.0(7) . . . . ? C13 C14 C15 O1 2.9(6) . . . . ? C9 C14 C15 O1 -176.4(4) . . . . ? C13 C14 C15 Cd1 121(2) . . . . ? C9 C14 C15 Cd1 -58(3) . . . . ? N4 Cd1 C15 O2 93.6(3) 7_447 . . . ? N1 Cd1 C15 O2 -151.7(3) . . . . ? O4 Cd1 C15 O2 -53.5(3) 2_566 . . . ? O1 Cd1 C15 O2 173.5(5) . . . . ? O3 Cd1 C15 O2 -22.4(4) 2_566 . . . ? N4 Cd1 C15 O1 -79.8(3) 7_447 . . . ? O2 Cd1 C15 O1 -173.5(5) . . . . ? N1 Cd1 C15 O1 34.8(3) . . . . ? O4 Cd1 C15 O1 133.0(3) 2_566 . . . ? O3 Cd1 C15 O1 164.1(3) 2_566 . . . ? N4 Cd1 C15 C14 158(2) 7_447 . . . ? O2 Cd1 C15 C14 65(2) . . . . ? N1 Cd1 C15 C14 -87(2) . . . . ? O4 Cd1 C15 C14 11(3) 2_566 . . . ? O1 Cd1 C15 C14 -122(3) . . . . ? O3 Cd1 C15 C14 42(3) 2_566 . . . ? N1 C17 C18 N2 0.6(5) . . . . ? N2 C19 C20 C21 178.6(5) . . . . ? C19 C20 C21 C22 169.7(5) . . . . ? C20 C21 C22 N3 61.5(7) . . . . ? N3 C23 N4 C24 0.3(6) . . . . ? N3 C23 N4 Cd1 179.0(3) . . . 7_447 ? N2 C16 N1 C17 1.7(6) . . . . ? N2 C16 N1 Cd1 -178.9(3) . . . . ? C18 C17 N1 C16 -1.4(5) . . . . ? C18 C17 N1 Cd1 179.3(3) . . . . ? N4 Cd1 N1 C16 55.9(4) 7_447 . . . ? O2 Cd1 N1 C16 -81.4(4) . . . . ? O4 Cd1 N1 C16 -166.1(4) 2_566 . . . ? O1 Cd1 N1 C16 -48.7(4) . . . . ? O3 Cd1 N1 C16 141.5(4) 2_566 . . . ? C15 Cd1 N1 C16 -63.9(4) . . . . ? N4 Cd1 N1 C17 -124.9(4) 7_447 . . . ? O2 Cd1 N1 C17 97.9(4) . . . . ? O4 Cd1 N1 C17 13.1(4) 2_566 . . . ? O1 Cd1 N1 C17 130.5(4) . . . . ? O3 Cd1 N1 C17 -39.2(4) 2_566 . . . ? C15 Cd1 N1 C17 115.3(4) . . . . ? N1 C16 N2 C18 -1.4(6) . . . . ? N1 C16 N2 C19 180.0(5) . . . . ? C17 C18 N2 C16 0.4(5) . . . . ? C17 C18 N2 C19 179.1(5) . . . . ? C20 C19 N2 C16 -129.3(6) . . . . ? C20 C19 N2 C18 52.4(7) . . . . ? N4 C23 N3 C25 -0.2(6) . . . . ? N4 C23 N3 C22 174.4(5) . . . . ? C24 C25 N3 C23 0.1(6) . . . . ? C24 C25 N3 C22 -174.5(5) . . . . ? C21 C22 N3 C23 68.5(8) . . . . ? C21 C22 N3 C25 -118.1(6) . . . . ? N3 C25 C24 N4 0.1(7) . . . . ? C23 N4 C24 C25 -0.2(6) . . . . ? Cd1 N4 C24 C25 -179.0(4) 7_447 . . . ? O2 C15 O1 Cd1 -6.1(5) . . . . ? C14 C15 O1 Cd1 172.3(4) . . . . ? N4 Cd1 O1 C15 108.9(3) 7_447 . . . ? O2 Cd1 O1 C15 3.6(3) . . . . ? N1 Cd1 O1 C15 -148.1(3) . . . . ? O4 Cd1 O1 C15 -54.2(3) 2_566 . . . ? O3 Cd1 O1 C15 -58.7(9) 2_566 . . . ? O1 C15 O2 Cd1 6.8(5) . . . . ? C14 C15 O2 Cd1 -171.6(4) . . . . ? N4 Cd1 O2 C15 -96.9(3) 7_447 . . . ? N1 Cd1 O2 C15 38.1(4) . . . . ? O4 Cd1 O2 C15 127.1(3) 2_566 . . . ? O1 Cd1 O2 C15 -3.7(3) . . . . ? O3 Cd1 O2 C15 165.7(3) 2_566 . . . ? O4 C1 O3 Cd1 11.2(5) . . . 2_546 ? C2 C1 O3 Cd1 -166.0(4) . . . 2_546 ? O3 C1 O4 Cd1 -13.3(6) . . . 2_546 ? C2 C1 O4 Cd1 164.1(3) . . . 2_546 ? C10 C9 N5 C8 4.6(6) . . . . ? C14 C9 N5 C8 -178.3(4) . . . . ? C5 C8 N5 C9 77.3(6) . . . . ? 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 H1WA O4 0.86(2) 2.27(10) 3.048(5) 152(18) 2_556 O1W H1WB O4 0.86(2) 2.25(9) 3.048(5) 154(17) . N5 H5N O2 0.80(5) 2.01(5) 2.645(5) 137(5) . _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.833 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.070 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 806749' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 N5 O5 Zn' _chemical_formula_weight 542.89 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2094(3) _cell_length_b 14.3216(3) _cell_length_c 17.7147(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.170(3) _cell_angle_gamma 90.00 _cell_volume 2557.05(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11703 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 29.31 _reflns_number_total 5938 _reflns_number_gt 3119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water and amine were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A with U~iso~ = 1.5U~eq~(O) and N---H = 0.87+-0.02 \%A with U~iso~ = 1.5U~eq~(N). The distance of H1WA...HW1B was restrained to 1.44+-0.02 \%A. ; _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^)+(0.0500P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5938 _refine_ls_number_parameters 335 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.826 _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 0.0637(3) 0.08707(18) 0.15989(15) 0.0437(7) Uani 1 1 d . . . C2 C -0.0116(3) 0.00516(16) 0.12210(15) 0.0410(7) Uani 1 1 d . . . C3 C 0.0540(3) -0.0689(2) 0.09602(19) 0.0613(9) Uani 1 1 d . . . H3 H 0.1462 -0.0709 0.1054 0.074 Uiso 1 1 calc R . . C4 C -0.0164(4) -0.1410(2) 0.0558(2) 0.0656(9) Uani 1 1 d . . . H4 H 0.0298 -0.1900 0.0378 0.079 Uiso 1 1 calc R . . C5 C -0.1531(3) -0.14168(17) 0.04184(15) 0.0460(7) Uani 1 1 d . . . C6 C -0.2176(3) -0.07002(19) 0.07182(18) 0.0564(8) Uani 1 1 d . . . H6 H -0.3098 -0.0703 0.0655 0.068 Uiso 1 1 calc R . . C7 C -0.1482(3) 0.00291(18) 0.11143(17) 0.0532(8) Uani 1 1 d . . . H7 H -0.1944 0.0508 0.1310 0.064 Uiso 1 1 calc R . . C8 C -0.2291(4) -0.21406(18) -0.00929(16) 0.0575(8) Uani 1 1 d . . . H8A H -0.3210 -0.2124 -0.0016 0.069 Uiso 1 1 calc R . . H8B H -0.2270 -0.1968 -0.0620 0.069 Uiso 1 1 calc R . . C9 C -0.1960(3) -0.36156(17) 0.06422(15) 0.0431(7) Uani 1 1 d . . . C10 C -0.2829(3) -0.33795(19) 0.11427(17) 0.0506(7) Uani 1 1 d . . . H10 H -0.3343 -0.2843 0.1054 0.061 Uiso 1 1 calc R . . C11 C -0.2937(3) -0.39325(19) 0.17701(17) 0.0509(8) Uani 1 1 d . . . H11 H -0.3529 -0.3766 0.2095 0.061 Uiso 1 1 calc R . . C12 C -0.2181(3) -0.47251(18) 0.19207(16) 0.0458(7) Uani 1 1 d . . . H12 H -0.2227 -0.5076 0.2358 0.055 Uiso 1 1 calc R . . C13 C -0.1343(3) -0.49973(17) 0.14109(15) 0.0407(7) Uani 1 1 d . . . C14 C -0.1247(3) -0.44528(17) 0.07816(16) 0.0439(7) Uani 1 1 d . . . H14 H -0.0695 -0.4644 0.0441 0.053 Uiso 1 1 calc R . . C15 C -0.0560(3) -0.58882(18) 0.15250(18) 0.0458(7) Uani 1 1 d . . . C16 C 0.2914(3) 0.39825(19) 0.17405(18) 0.0548(8) Uani 1 1 d . . . H16 H 0.2311 0.4443 0.1547 0.066 Uiso 1 1 calc R . . C17 C 0.4233(3) 0.4051(2) 0.18096(18) 0.0579(8) Uani 1 1 d . . . H17 H 0.4707 0.4563 0.1676 0.070 Uiso 1 1 calc R . . C18 C 0.3733(3) 0.2703(2) 0.22177(16) 0.0476(7) Uani 1 1 d . . . H18 H 0.3815 0.2103 0.2421 0.057 Uiso 1 1 calc R . . C19 C 0.6149(3) 0.2969(2) 0.22743(17) 0.0578(8) Uani 1 1 d . . . H19A H 0.6307 0.2632 0.2755 0.069 Uiso 1 1 calc R . . H19B H 0.6690 0.3529 0.2332 0.069 Uiso 1 1 calc R . . C20 C 0.6571(3) 0.2370(2) 0.16614(16) 0.0570(8) Uani 1 1 d . . . H20A H 0.6072 0.1791 0.1631 0.068 Uiso 1 1 calc R . . H20B H 0.7502 0.2214 0.1808 0.068 Uiso 1 1 calc R . . C21 C 0.6378(3) 0.2819(2) 0.08731(16) 0.0544(8) Uani 1 1 d . . . H21A H 0.5438 0.2867 0.0676 0.065 Uiso 1 1 calc R . . H21B H 0.6749 0.3445 0.0910 0.065 Uiso 1 1 calc R . . C22 C 0.7053(4) 0.2242(2) 0.03357(16) 0.0670(9) Uani 1 1 d . . . H22A H 0.7995 0.2213 0.0532 0.080 Uiso 1 1 calc R . . H22B H 0.6707 0.1611 0.0322 0.080 Uiso 1 1 calc R . . C23 C 0.7315(4) 0.3444(2) -0.0658(2) 0.0762(11) Uani 1 1 d . . . H23 H 0.7781 0.3893 -0.0345 0.091 Uiso 1 1 calc R . . C24 C 0.6950(4) 0.3491(2) -0.14196(19) 0.0688(10) Uani 1 1 d . . . H24 H 0.7126 0.3991 -0.1723 0.083 Uiso 1 1 calc R . . C25 C 0.6269(3) 0.2188(2) -0.10675(17) 0.0500(7) Uani 1 1 d . . . H25 H 0.5884 0.1599 -0.1072 0.060 Uiso 1 1 calc R . . N1 N 0.2594(2) 0.31306(14) 0.19987(12) 0.0428(6) Uani 1 1 d . . . N2 N 0.4751(2) 0.32368(16) 0.21107(13) 0.0459(6) Uani 1 1 d . . . N3 N 0.6869(3) 0.26121(17) -0.04380(13) 0.0540(6) Uani 1 1 d . . . N4 N 0.6283(2) 0.27018(16) -0.16842(13) 0.0472(6) Uani 1 1 d . . . O1 O -0.00819(19) 0.15813(12) 0.17112(11) 0.0530(5) Uani 1 1 d . . . O2 O 0.1844(2) 0.08594(13) 0.17736(12) 0.0584(6) Uani 1 1 d . . . O3 O -0.0339(2) -0.62259(12) 0.22067(12) 0.0533(5) Uani 1 1 d . . . O4 O -0.0158(2) -0.62622(13) 0.09781(12) 0.0616(6) Uani 1 1 d . . . Zn1 Zn 0.08275(3) 0.26646(2) 0.219833(18) 0.04107(12) Uani 1 1 d . . . N5 N -0.1814(3) -0.30840(17) 0.00219(15) 0.0597(7) Uani 1 1 d D . . H5N H -0.125(2) -0.3291(17) -0.0213(14) 0.036(8) Uiso 1 1 d D . . O1W O 0.5674(3) -0.0105(2) -0.14887(17) 0.0976(9) Uani 1 1 d D . . H1WA H 0.536(4) 0.009(3) -0.1962(15) 0.146 Uiso 1 1 d D . . H1WB H 0.646(3) -0.035(3) -0.154(3) 0.146 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.054(2) 0.0384(15) 0.0396(17) 0.0040(12) 0.0094(15) -0.0004(15) C2 0.051(2) 0.0339(14) 0.0392(15) 0.0024(12) 0.0091(14) 0.0009(13) C3 0.047(2) 0.0518(18) 0.086(2) -0.0141(17) 0.0147(18) 0.0056(15) C4 0.077(3) 0.0408(17) 0.083(2) -0.0210(16) 0.026(2) 0.0090(16) C5 0.065(2) 0.0334(15) 0.0399(16) 0.0014(12) 0.0097(15) 0.0011(14) C6 0.053(2) 0.0460(17) 0.068(2) -0.0034(15) 0.0031(17) -0.0004(15) C7 0.056(2) 0.0395(16) 0.065(2) -0.0097(14) 0.0127(17) 0.0059(14) C8 0.089(3) 0.0379(17) 0.0437(17) -0.0028(13) 0.0041(17) -0.0040(15) C9 0.053(2) 0.0355(15) 0.0417(16) -0.0087(13) 0.0097(15) -0.0038(13) C10 0.053(2) 0.0419(15) 0.0561(19) -0.0049(14) 0.0079(16) 0.0083(14) C11 0.051(2) 0.0473(17) 0.059(2) -0.0106(15) 0.0222(16) 0.0034(14) C12 0.0507(19) 0.0435(15) 0.0459(17) -0.0001(13) 0.0159(14) -0.0028(14) C13 0.0394(18) 0.0369(14) 0.0459(17) -0.0068(12) 0.0069(14) -0.0018(12) C14 0.0446(18) 0.0399(15) 0.0502(18) -0.0096(13) 0.0170(14) -0.0054(13) C15 0.0405(18) 0.0380(15) 0.059(2) -0.0072(15) 0.0094(16) -0.0022(13) C16 0.050(2) 0.0414(16) 0.073(2) 0.0031(15) 0.0099(17) 0.0005(14) C17 0.056(2) 0.0439(17) 0.074(2) 0.0029(16) 0.0126(18) -0.0115(15) C18 0.0469(19) 0.0437(15) 0.0530(17) 0.0062(14) 0.0109(14) -0.0043(15) C19 0.043(2) 0.082(2) 0.0478(18) -0.0006(16) 0.0056(15) -0.0024(15) C20 0.0451(19) 0.075(2) 0.0504(18) 0.0050(16) 0.0076(15) 0.0054(15) C21 0.0440(18) 0.066(2) 0.0523(18) -0.0027(16) 0.0056(15) 0.0009(15) C22 0.077(2) 0.081(2) 0.0436(18) 0.0072(17) 0.0107(17) 0.0235(18) C23 0.108(3) 0.067(2) 0.052(2) -0.0163(17) 0.008(2) -0.020(2) C24 0.106(3) 0.0498(19) 0.052(2) -0.0056(15) 0.016(2) -0.0141(18) C25 0.058(2) 0.0443(16) 0.0494(19) -0.0011(15) 0.0128(15) 0.0095(14) N1 0.0434(15) 0.0375(12) 0.0488(14) 0.0018(10) 0.0116(12) -0.0002(11) N2 0.0420(15) 0.0519(14) 0.0441(14) -0.0024(11) 0.0074(12) -0.0035(12) N3 0.0640(17) 0.0581(16) 0.0401(14) -0.0047(13) 0.0086(12) 0.0087(13) N4 0.0547(16) 0.0426(13) 0.0446(14) -0.0018(12) 0.0092(12) 0.0073(12) O1 0.0547(14) 0.0393(10) 0.0645(14) -0.0095(9) 0.0079(11) 0.0009(9) O2 0.0488(15) 0.0506(12) 0.0737(15) -0.0041(10) 0.0030(12) -0.0014(10) O3 0.0585(14) 0.0428(11) 0.0600(14) 0.0024(10) 0.0131(11) 0.0080(9) O4 0.0664(15) 0.0560(12) 0.0642(14) -0.0105(11) 0.0158(12) 0.0184(10) Zn1 0.0428(2) 0.03680(17) 0.0442(2) -0.00058(15) 0.00865(14) -0.00070(15) N5 0.096(2) 0.0383(14) 0.0498(17) -0.0071(12) 0.0277(16) 0.0018(14) O1W 0.085(2) 0.098(2) 0.110(2) 0.0153(17) 0.0160(18) 0.0122(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.222(3) . ? C1 O1 1.288(3) . ? C1 C2 1.500(4) . ? C2 C3 1.374(4) . ? C2 C7 1.378(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(4) . ? C4 H4 0.9300 . ? C5 C6 1.371(4) . ? C5 C8 1.507(4) . ? C6 C7 1.388(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N5 1.440(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N5 1.365(4) . ? C9 C10 1.392(4) . ? C9 C14 1.404(4) . ? C10 C11 1.383(4) . ? C10 H10 0.9300 . ? C11 C12 1.375(4) . ? C11 H11 0.9300 . ? C12 C13 1.395(4) . ? C12 H12 0.9300 . ? C13 C14 1.377(4) . ? C13 C15 1.502(4) . ? C14 H14 0.9300 . ? C15 O4 1.233(3) . ? C15 O3 1.287(3) . ? C16 C17 1.336(4) . ? C16 N1 1.361(3) . ? C16 H16 0.9300 . ? C17 N2 1.355(4) . ? C17 H17 0.9300 . ? C18 N1 1.317(3) . ? C18 N2 1.328(3) . ? C18 H18 0.9300 . ? C19 N2 1.461(4) . ? C19 C20 1.500(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.522(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.508(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N3 1.453(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.342(4) . ? C23 N3 1.355(4) . ? C23 H23 0.9300 . ? C24 N4 1.364(4) . ? C24 H24 0.9300 . ? C25 N4 1.319(3) . ? C25 N3 1.331(4) . ? C25 H25 0.9300 . ? N1 Zn1 2.007(2) . y N4 Zn1 2.029(2) 4_665 y O1 Zn1 1.9387(18) . y O3 Zn1 1.9873(18) 1_545 y Zn1 O3 1.9873(18) 1_565 y Zn1 N4 2.029(2) 4_566 y N5 H5N 0.815(16) . ? O1W H1WA 0.894(18) . ? O1W H1WB 0.891(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 123.2(3) . . ? O2 C1 C2 121.8(3) . . ? O1 C1 C2 115.0(3) . . ? C3 C2 C7 118.2(3) . . ? C3 C2 C1 120.8(3) . . ? C7 C2 C1 121.0(2) . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 117.4(3) . . ? C6 C5 C8 121.0(3) . . ? C4 C5 C8 121.5(3) . . ? C5 C6 C7 121.4(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C2 C7 C6 120.7(3) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N5 C8 C5 115.5(3) . . ? N5 C8 H8A 108.4 . . ? C5 C8 H8A 108.4 . . ? N5 C8 H8B 108.4 . . ? C5 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? N5 C9 C10 122.7(3) . . ? N5 C9 C14 119.8(3) . . ? C10 C9 C14 117.4(3) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 C15 119.0(2) . . ? C12 C13 C15 121.2(2) . . ? C13 C14 C9 121.6(2) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? O4 C15 O3 122.9(3) . . ? O4 C15 C13 120.0(3) . . ? O3 C15 C13 117.1(2) . . ? C17 C16 N1 109.1(3) . . ? C17 C16 H16 125.4 . . ? N1 C16 H16 125.4 . . ? C16 C17 N2 107.3(3) . . ? C16 C17 H17 126.3 . . ? N2 C17 H17 126.3 . . ? N1 C18 N2 111.4(3) . . ? N1 C18 H18 124.3 . . ? N2 C18 H18 124.3 . . ? N2 C19 C20 113.0(2) . . ? N2 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? N2 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 C21 114.3(3) . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20B 108.7 . . ? C21 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C22 C21 C20 110.0(2) . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? N3 C22 C21 113.1(3) . . ? N3 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? N3 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 N3 106.4(3) . . ? C24 C23 H23 126.8 . . ? N3 C23 H23 126.8 . . ? C23 C24 N4 110.3(3) . . ? C23 C24 H24 124.9 . . ? N4 C24 H24 124.9 . . ? N4 C25 N3 112.0(3) . . ? N4 C25 H25 124.0 . . ? N3 C25 H25 124.0 . . ? C18 N1 C16 105.5(2) . . ? C18 N1 Zn1 124.75(18) . . ? C16 N1 Zn1 128.9(2) . . ? C18 N2 C17 106.6(2) . . ? C18 N2 C19 125.6(3) . . ? C17 N2 C19 127.7(3) . . ? C25 N3 C23 106.9(3) . . ? C25 N3 C22 126.7(3) . . ? C23 N3 C22 126.4(3) . . ? C25 N4 C24 104.4(2) . . ? C25 N4 Zn1 129.2(2) . 4_665 y C24 N4 Zn1 125.0(2) . 4_665 y C1 O1 Zn1 117.18(19) . . y C15 O3 Zn1 108.01(17) . 1_545 y O1 Zn1 O3 113.45(8) . 1_565 y O1 Zn1 N1 124.60(8) . . y O3 Zn1 N1 106.98(8) 1_565 . y O1 Zn1 N4 104.27(9) . 4_566 y O3 Zn1 N4 104.12(9) 1_565 4_566 y N1 Zn1 N4 100.67(9) . 4_566 y C9 N5 C8 124.0(3) . . ? C9 N5 H5N 112.6(19) . . ? C8 N5 H5N 121.2(19) . . ? H1WA O1W H1WB 103(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -9.3(4) . . . . ? O1 C1 C2 C3 169.7(3) . . . . ? O2 C1 C2 C7 171.8(3) . . . . ? O1 C1 C2 C7 -9.2(4) . . . . ? C7 C2 C3 C4 4.0(5) . . . . ? C1 C2 C3 C4 -174.9(3) . . . . ? C2 C3 C4 C5 -1.2(5) . . . . ? C3 C4 C5 C6 -2.4(5) . . . . ? C3 C4 C5 C8 173.0(3) . . . . ? C4 C5 C6 C7 3.1(4) . . . . ? C8 C5 C6 C7 -172.3(3) . . . . ? C3 C2 C7 C6 -3.3(4) . . . . ? C1 C2 C7 C6 175.6(3) . . . . ? C5 C6 C7 C2 -0.3(5) . . . . ? C6 C5 C8 N5 -140.7(3) . . . . ? C4 C5 C8 N5 44.0(4) . . . . ? N5 C9 C10 C11 -179.3(3) . . . . ? C14 C9 C10 C11 2.6(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 -3.2(4) . . . . ? C11 C12 C13 C14 2.4(4) . . . . ? C11 C12 C13 C15 -176.2(3) . . . . ? C12 C13 C14 C9 0.9(4) . . . . ? C15 C13 C14 C9 179.6(2) . . . . ? N5 C9 C14 C13 178.4(3) . . . . ? C10 C9 C14 C13 -3.4(4) . . . . ? C14 C13 C15 O4 -20.8(4) . . . . ? C12 C13 C15 O4 157.9(3) . . . . ? C14 C13 C15 O3 159.1(2) . . . . ? C12 C13 C15 O3 -22.2(4) . . . . ? N1 C16 C17 N2 0.2(3) . . . . ? N2 C19 C20 C21 58.9(4) . . . . ? C19 C20 C21 C22 169.8(3) . . . . ? C20 C21 C22 N3 177.9(3) . . . . ? N3 C23 C24 N4 -0.2(4) . . . . ? N2 C18 N1 C16 -0.1(3) . . . . ? N2 C18 N1 Zn1 -170.50(17) . . . . ? C17 C16 N1 C18 -0.1(3) . . . . ? C17 C16 N1 Zn1 169.8(2) . . . . ? N1 C18 N2 C17 0.2(3) . . . . ? N1 C18 N2 C19 -178.4(2) . . . . ? C16 C17 N2 C18 -0.3(3) . . . . ? C16 C17 N2 C19 178.3(3) . . . . ? C20 C19 N2 C18 79.9(3) . . . . ? C20 C19 N2 C17 -98.5(4) . . . . ? N4 C25 N3 C23 -0.8(3) . . . . ? N4 C25 N3 C22 -178.9(3) . . . . ? C24 C23 N3 C25 0.6(4) . . . . ? C24 C23 N3 C22 178.7(3) . . . . ? C21 C22 N3 C25 -118.2(3) . . . . ? C21 C22 N3 C23 64.0(4) . . . . ? N3 C25 N4 C24 0.7(3) . . . . ? N3 C25 N4 Zn1 167.85(19) . . . 4_665 ? C23 C24 N4 C25 -0.3(4) . . . . ? C23 C24 N4 Zn1 -168.2(2) . . . 4_665 ? O2 C1 O1 Zn1 -1.1(4) . . . . ? C2 C1 O1 Zn1 179.95(16) . . . . ? O4 C15 O3 Zn1 4.3(3) . . . 1_545 ? C13 C15 O3 Zn1 -175.53(18) . . . 1_545 ? C1 O1 Zn1 O3 171.73(18) . . . 1_565 ? C1 O1 Zn1 N1 38.4(2) . . . . ? C1 O1 Zn1 N4 -75.6(2) . . . 4_566 ? C18 N1 Zn1 O1 -70.4(2) . . . . ? C16 N1 Zn1 O1 121.5(2) . . . . ? C18 N1 Zn1 O3 153.8(2) . . . 1_565 ? C16 N1 Zn1 O3 -14.2(3) . . . 1_565 ? C18 N1 Zn1 N4 45.3(2) . . . 4_566 ? C16 N1 Zn1 N4 -122.7(2) . . . 4_566 ? C10 C9 N5 C8 14.4(5) . . . . ? C14 C9 N5 C8 -167.6(3) . . . . ? C5 C8 N5 C9 72.2(4) . . . . ? 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 N5 H5N O4 0.815(16) 2.224(17) 3.034(4) 173(3) 3_545 O1W H1WA O3 0.894(18) 2.23(3) 3.047(3) 151(4) 4_655 O1W H1WB O2 0.891(18) 1.98(2) 2.872(4) 174(4) 3_655 _diffrn_measured_fraction_theta_max 0.849 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.931 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.054 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 806750' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cd N3 O5' _chemical_formula_weight 494.79 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 9.617(3) _cell_length_b 10.173(5) _cell_length_c 11.458(4) _cell_angle_alpha 108.033(5) _cell_angle_beta 97.015(3) _cell_angle_gamma 105.519(5) _cell_volume 1001.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.673 _exptl_absorpt_correction_T_max 0.798 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10876 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 29.24 _reflns_number_total 4655 _reflns_number_gt 3360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0402P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4655 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _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 0.195428(19) 0.018014(17) -0.00628(2) 0.04745(8) Uani 1 1 d . . . C1 C 0.2723(3) -0.2730(2) -0.0400(3) 0.0426(6) Uani 1 1 d . . . H1 H 0.3705 -0.2178 -0.0007 0.051 Uiso 1 1 calc R . . C2 C 0.0422(3) -0.3342(3) -0.1224(3) 0.0515(7) Uani 1 1 d . . . H2 H -0.0503 -0.3288 -0.1507 0.062 Uiso 1 1 calc R . . C3 C 0.0723(3) -0.4584(3) -0.1315(3) 0.0541(7) Uani 1 1 d . . . H3 H 0.0059 -0.5530 -0.1674 0.065 Uiso 1 1 calc R . . C4 C 0.3024(3) -0.5200(2) -0.0731(3) 0.0472(6) Uani 1 1 d . . . H4A H 0.3061 -0.5737 -0.1583 0.057 Uiso 1 1 calc R . . H4B H 0.2496 -0.5901 -0.0393 0.057 Uiso 1 1 calc R . . C5 C 0.4572(3) -0.4457(2) 0.0050(3) 0.0396(6) Uani 1 1 d . . . H5A H 0.4542 -0.4009 0.0924 0.048 Uiso 1 1 calc R . . H5B H 0.5079 -0.3690 -0.0230 0.048 Uiso 1 1 calc R . . C6 C 0.3901(3) 0.2461(3) 0.1863(2) 0.0391(5) Uani 1 1 d . . . C7 C 0.5057(3) 0.3759(2) 0.2850(2) 0.0390(5) Uani 1 1 d . . . C8 C 0.6437(3) 0.3676(3) 0.3270(3) 0.0466(6) Uani 1 1 d . . . H8 H 0.6627 0.2797 0.2963 0.056 Uiso 1 1 calc R . . C9 C 0.7531(3) 0.4889(3) 0.4142(3) 0.0521(7) Uani 1 1 d . . . H9 H 0.8455 0.4823 0.4407 0.063 Uiso 1 1 calc R . . C10 C 0.7263(3) 0.6200(3) 0.4623(3) 0.0501(7) Uani 1 1 d . . . C11 C 0.5886(4) 0.6273(3) 0.4205(3) 0.0565(7) Uani 1 1 d . . . H11 H 0.5692 0.7148 0.4523 0.068 Uiso 1 1 calc R . . C12 C 0.4790(3) 0.5071(3) 0.3321(3) 0.0489(6) Uani 1 1 d . . . H12 H 0.3875 0.5146 0.3044 0.059 Uiso 1 1 calc R . . C13 C 0.8425(4) 0.7523(3) 0.5622(3) 0.0677(9) Uani 1 1 d . . . H13A H 0.8256 0.8398 0.5555 0.081 Uiso 1 1 calc R . . H13B H 0.8301 0.7505 0.6445 0.081 Uiso 1 1 calc R . . C14 C 1.0560(3) 0.8022(3) 0.4632(3) 0.0541(7) Uani 1 1 d . . . C15 C 1.2024(4) 0.8140(4) 0.4622(3) 0.0759(10) Uani 1 1 d . . . H15 H 1.2579 0.7949 0.5236 0.091 Uiso 1 1 calc R . . C16 C 1.2676(4) 0.8533(4) 0.3726(4) 0.0792(10) Uani 1 1 d . . . H16 H 1.3654 0.8578 0.3726 0.095 Uiso 1 1 calc R . . C17 C 1.1891(3) 0.8863(3) 0.2821(3) 0.0582(7) Uani 1 1 d . . . H17 H 1.2343 0.9151 0.2228 0.070 Uiso 1 1 calc R . . C18 C 1.0432(3) 0.8761(2) 0.2812(2) 0.0403(6) Uani 1 1 d . . . C19 C 0.9758(3) 0.8327(2) 0.3701(2) 0.0452(6) Uani 1 1 d . . . H19 H 0.8766 0.8238 0.3677 0.054 Uiso 1 1 calc R . . C20 C 0.9563(3) 0.9169(2) 0.1884(2) 0.0411(6) Uani 1 1 d . . . N1 N 0.1687(2) -0.2172(2) -0.0653(2) 0.0430(5) Uani 1 1 d . . . N2 N 0.2194(2) -0.41872(19) -0.0776(2) 0.0396(5) Uani 1 1 d . . . O1 O 0.4124(2) 0.12460(18) 0.1506(2) 0.0584(5) Uani 1 1 d . . . O2 O 0.27493(19) 0.25949(19) 0.1366(2) 0.0556(5) Uani 1 1 d . . . O3 O 1.0197(2) 0.9759(2) 0.11943(19) 0.0536(5) Uani 1 1 d . . . O4 O 0.8216(2) 0.8931(3) 0.1807(2) 0.0718(6) Uani 1 1 d . . . O1W O 0.4083(4) 0.0323(4) -0.1286(4) 0.0979(10) Uani 0.80 1 d P . . O1W' O 0.4532(9) 0.0678(9) -0.2334(8) 0.045(2) Uiso 0.20 1 d P . . N3 N 0.9923(3) 0.7614(3) 0.5542(2) 0.0712(8) Uani 1 1 d . . . H3N H 1.048(4) 0.769(4) 0.613(4) 0.085 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03696(11) 0.03068(10) 0.06795(16) 0.01386(8) -0.00682(8) 0.01290(7) C1 0.0339(12) 0.0296(11) 0.0615(18) 0.0130(11) 0.0055(12) 0.0122(9) C2 0.0352(13) 0.0424(13) 0.073(2) 0.0158(13) 0.0022(13) 0.0164(11) C3 0.0358(14) 0.0358(13) 0.081(2) 0.0135(13) 0.0038(13) 0.0094(10) C4 0.0475(15) 0.0324(12) 0.0664(19) 0.0195(12) 0.0102(13) 0.0194(11) C5 0.0457(14) 0.0354(12) 0.0474(16) 0.0195(11) 0.0137(12) 0.0213(10) C6 0.0353(13) 0.0414(13) 0.0417(15) 0.0180(11) 0.0134(11) 0.0083(10) C7 0.0417(13) 0.0396(12) 0.0345(14) 0.0152(11) 0.0083(11) 0.0090(10) C8 0.0485(15) 0.0413(13) 0.0434(16) 0.0127(12) 0.0011(12) 0.0109(11) C9 0.0480(15) 0.0543(16) 0.0433(17) 0.0161(13) -0.0021(12) 0.0066(12) C10 0.0598(17) 0.0473(14) 0.0325(15) 0.0116(12) 0.0125(13) 0.0024(12) C11 0.077(2) 0.0381(13) 0.0496(18) 0.0096(13) 0.0227(16) 0.0145(13) C12 0.0532(16) 0.0430(14) 0.0479(17) 0.0126(12) 0.0136(13) 0.0148(12) C13 0.082(2) 0.0551(17) 0.0361(17) 0.0043(13) 0.0086(15) -0.0097(15) C14 0.0586(18) 0.0409(14) 0.0446(17) 0.0152(12) -0.0034(13) -0.0058(12) C15 0.066(2) 0.090(2) 0.080(3) 0.057(2) -0.0043(18) 0.0154(18) C16 0.0523(19) 0.111(3) 0.103(3) 0.068(2) 0.0171(19) 0.0371(19) C17 0.0572(18) 0.0706(18) 0.067(2) 0.0427(17) 0.0176(15) 0.0300(15) C18 0.0422(13) 0.0302(11) 0.0444(16) 0.0120(11) 0.0030(11) 0.0099(10) C19 0.0454(14) 0.0345(12) 0.0437(16) 0.0086(11) 0.0035(12) 0.0031(10) C20 0.0426(14) 0.0273(11) 0.0449(16) 0.0041(10) 0.0030(12) 0.0115(10) N1 0.0356(11) 0.0329(10) 0.0599(14) 0.0136(10) 0.0045(10) 0.0165(8) N2 0.0375(11) 0.0309(9) 0.0538(14) 0.0151(9) 0.0099(10) 0.0166(8) O1 0.0413(10) 0.0389(9) 0.0779(14) 0.0063(9) -0.0048(9) 0.0110(8) O2 0.0394(10) 0.0483(10) 0.0703(14) 0.0150(9) -0.0014(9) 0.0135(8) O3 0.0510(11) 0.0591(11) 0.0667(13) 0.0400(10) 0.0126(10) 0.0226(9) O4 0.0393(11) 0.0949(16) 0.0874(17) 0.0434(14) 0.0101(11) 0.0211(10) O1W 0.074(2) 0.097(2) 0.134(3) 0.044(2) 0.020(2) 0.0443(18) N3 0.075(2) 0.0700(16) 0.0411(16) 0.0226(14) -0.0071(13) -0.0150(14) _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 N1 2.208(2) . ? Cd1 O1 2.329(2) . ? Cd1 O3 2.3297(19) 2_665 ? Cd1 O2 2.345(2) . ? Cd1 O3 2.3881(19) 1_445 ? Cd1 O4 2.441(2) 2_665 ? Cd1 O1W 2.616(3) . ? Cd1 C6 2.693(3) . ? Cd1 C20 2.748(3) 2_665 ? C1 N1 1.317(3) . ? C1 N2 1.337(3) . ? C1 H1 0.9300 . ? C2 C3 1.347(3) . ? C2 N1 1.369(3) . ? C2 H2 0.9300 . ? C3 N2 1.368(3) . ? C3 H3 0.9300 . ? C4 N2 1.471(3) . ? C4 C5 1.498(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.531(4) 2_645 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.243(3) . ? C6 O1 1.261(3) . ? C6 C7 1.498(3) . ? C7 C12 1.382(3) . ? C7 C8 1.389(4) . ? C8 C9 1.383(4) . ? C8 H8 0.9300 . ? C9 C10 1.383(4) . ? C9 H9 0.9300 . ? C10 C11 1.381(4) . ? C10 C13 1.516(4) . ? C11 C12 1.383(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N3 1.435(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.382(4) . ? C14 N3 1.386(4) . ? C14 C19 1.400(4) . ? C15 C16 1.373(5) . ? C15 H15 0.9300 . ? C16 C17 1.384(4) . ? C16 H16 0.9300 . ? C17 C18 1.378(4) . ? C17 H17 0.9300 . ? C18 C19 1.393(4) . ? C18 C20 1.497(3) . ? C19 H19 0.9300 . ? C20 O4 1.239(3) . ? C20 O3 1.255(3) . ? C20 Cd1 2.748(3) 2_665 ? O3 Cd1 2.3297(19) 2_665 ? O3 Cd1 2.3881(19) 1_665 ? O4 Cd1 2.441(2) 2_665 ? O1W O1W' 1.439(9) . ? N3 H3N 0.78(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O1 102.91(7) . . ? N1 Cd1 O3 103.70(7) . 2_665 ? O1 Cd1 O3 152.85(7) . 2_665 ? N1 Cd1 O2 154.72(8) . . ? O1 Cd1 O2 55.34(6) . . ? O3 Cd1 O2 97.53(7) 2_665 . ? N1 Cd1 O3 87.20(7) . 1_445 ? O1 Cd1 O3 99.45(8) . 1_445 ? O3 Cd1 O3 76.59(7) 2_665 1_445 ? O2 Cd1 O3 84.49(7) . 1_445 ? N1 Cd1 O4 113.88(8) . 2_665 ? O1 Cd1 O4 118.32(7) . 2_665 ? O3 Cd1 O4 53.80(6) 2_665 2_665 ? O2 Cd1 O4 89.71(8) . 2_665 ? O3 Cd1 O4 128.78(6) 1_445 2_665 ? N1 Cd1 O1W 84.93(9) . . ? O1 Cd1 O1W 75.44(10) . . ? O3 Cd1 O1W 112.25(10) 2_665 . ? O2 Cd1 O1W 99.69(9) . . ? O3 Cd1 O1W 169.37(8) 1_445 . ? O4 Cd1 O1W 61.34(9) 2_665 . ? N1 Cd1 C6 130.00(8) . . ? O1 Cd1 C6 27.89(7) . . ? O3 Cd1 C6 124.96(8) 2_665 . ? O2 Cd1 C6 27.46(7) . . ? O3 Cd1 C6 92.94(7) 1_445 . ? O4 Cd1 C6 104.55(8) 2_665 . ? O1W Cd1 C6 86.67(10) . . ? N1 Cd1 C20 112.08(8) . 2_665 ? O1 Cd1 C20 139.11(7) . 2_665 ? O3 Cd1 C20 27.04(6) 2_665 2_665 ? O2 Cd1 C20 93.05(7) . 2_665 ? O3 Cd1 C20 102.66(7) 1_445 2_665 ? O4 Cd1 C20 26.79(7) 2_665 2_665 ? O1W Cd1 C20 86.95(10) . 2_665 ? C6 Cd1 C20 116.56(7) . 2_665 ? N1 C1 N2 111.8(2) . . ? N1 C1 H1 124.1 . . ? N2 C1 H1 124.1 . . ? C3 C2 N1 109.5(2) . . ? C3 C2 H2 125.3 . . ? N1 C2 H2 125.3 . . ? C2 C3 N2 106.8(2) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 C5 113.58(18) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C5 111.1(2) . 2_645 ? C4 C5 H5A 109.4 . . ? C5 C5 H5A 109.4 2_645 . ? C4 C5 H5B 109.4 . . ? C5 C5 H5B 109.4 2_645 . ? H5A C5 H5B 108.0 . . ? O2 C6 O1 120.2(2) . . ? O2 C6 C7 119.9(2) . . ? O1 C6 C7 119.8(2) . . ? O2 C6 Cd1 60.47(14) . . ? O1 C6 Cd1 59.79(13) . . ? C7 C6 Cd1 174.93(16) . . ? C12 C7 C8 119.0(2) . . ? C12 C7 C6 120.7(2) . . ? C8 C7 C6 120.2(2) . . ? C9 C8 C7 120.5(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 118.5(3) . . ? C11 C10 C13 120.1(3) . . ? C9 C10 C13 121.4(3) . . ? C10 C11 C12 121.4(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C7 C12 C11 120.0(3) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N3 C13 C10 114.4(3) . . ? N3 C13 H13A 108.7 . . ? C10 C13 H13A 108.7 . . ? N3 C13 H13B 108.7 . . ? C10 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 N3 120.3(3) . . ? C15 C14 C19 117.9(2) . . ? N3 C14 C19 121.8(3) . . ? C16 C15 C14 121.4(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 120.7(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 119.2(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 C20 120.9(2) . . ? C19 C18 C20 118.9(2) . . ? C18 C19 C14 120.7(2) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? O4 C20 O3 120.1(2) . . ? O4 C20 C18 119.8(2) . . ? O3 C20 C18 120.2(2) . . ? O4 C20 Cd1 62.64(15) . 2_665 ? O3 C20 Cd1 57.56(13) . 2_665 ? C18 C20 Cd1 176.26(17) . 2_665 ? C1 N1 C2 105.39(19) . . ? C1 N1 Cd1 125.62(16) . . ? C2 N1 Cd1 128.67(15) . . ? C1 N2 C3 106.48(19) . . ? C1 N2 C4 127.8(2) . . ? C3 N2 C4 125.53(19) . . ? C6 O1 Cd1 92.32(16) . . ? C6 O2 Cd1 92.07(15) . . ? C20 O3 Cd1 95.41(15) . 2_665 ? C20 O3 Cd1 155.60(16) . 1_665 ? Cd1 O3 Cd1 103.41(7) 2_665 1_665 ? C20 O4 Cd1 90.57(16) . 2_665 ? O1W' O1W Cd1 142.6(4) . . ? C14 N3 C13 122.6(3) . . ? C14 N3 H3N 115(3) . . ? C13 N3 H3N 119(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 0.8(3) . . . . ? N2 C4 C5 C5 -174.1(2) . . . 2_645 ? N1 Cd1 C6 O2 -160.93(14) . . . . ? O1 Cd1 C6 O2 -176.8(2) . . . . ? O3 Cd1 C6 O2 3.57(17) 2_665 . . . ? O3 Cd1 C6 O2 -72.11(15) 1_445 . . . ? O4 Cd1 C6 O2 59.29(16) 2_665 . . . ? O1W Cd1 C6 O2 118.53(16) . . . . ? C20 Cd1 C6 O2 33.62(17) 2_665 . . . ? N1 Cd1 C6 O1 15.91(18) . . . . ? O3 Cd1 C6 O1 -179.60(14) 2_665 . . . ? O2 Cd1 C6 O1 176.8(2) . . . . ? O3 Cd1 C6 O1 104.73(15) 1_445 . . . ? O4 Cd1 C6 O1 -123.87(15) 2_665 . . . ? O1W Cd1 C6 O1 -64.63(16) . . . . ? C20 Cd1 C6 O1 -149.54(15) 2_665 . . . ? N1 Cd1 C6 C7 103(2) . . . . ? O1 Cd1 C6 C7 87(2) . . . . ? O3 Cd1 C6 C7 -92(2) 2_665 . . . ? O2 Cd1 C6 C7 -96(2) . . . . ? O3 Cd1 C6 C7 -168(2) 1_445 . . . ? O4 Cd1 C6 C7 -37(2) 2_665 . . . ? O1W Cd1 C6 C7 23(2) . . . . ? C20 Cd1 C6 C7 -62(2) 2_665 . . . ? O2 C6 C7 C12 7.4(3) . . . . ? O1 C6 C7 C12 -175.2(2) . . . . ? Cd1 C6 C7 C12 101(2) . . . . ? O2 C6 C7 C8 -170.0(2) . . . . ? O1 C6 C7 C8 7.3(3) . . . . ? Cd1 C6 C7 C8 -77(2) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? C6 C7 C8 C9 177.2(2) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C8 C9 C10 C13 177.3(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C13 C10 C11 C12 -178.1(2) . . . . ? C8 C7 C12 C11 -0.5(4) . . . . ? C6 C7 C12 C11 -178.0(2) . . . . ? C10 C11 C12 C7 0.8(4) . . . . ? C11 C10 C13 N3 -150.3(3) . . . . ? C9 C10 C13 N3 31.8(4) . . . . ? N3 C14 C15 C16 179.6(3) . . . . ? C19 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C17 1.8(6) . . . . ? C15 C16 C17 C18 -1.5(5) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C16 C17 C18 C20 177.4(3) . . . . ? C17 C18 C19 C14 1.5(4) . . . . ? C20 C18 C19 C14 -176.1(2) . . . . ? C15 C14 C19 C18 -1.2(4) . . . . ? N3 C14 C19 C18 178.8(2) . . . . ? C17 C18 C20 O4 172.7(3) . . . . ? C19 C18 C20 O4 -9.7(3) . . . . ? C17 C18 C20 O3 -7.8(4) . . . . ? C19 C18 C20 O3 169.8(2) . . . . ? C17 C18 C20 Cd1 44(3) . . . 2_665 ? C19 C18 C20 Cd1 -139(2) . . . 2_665 ? N2 C1 N1 C2 0.0(3) . . . . ? N2 C1 N1 Cd1 173.95(16) . . . . ? C3 C2 N1 C1 -0.5(3) . . . . ? C3 C2 N1 Cd1 -174.3(2) . . . . ? O1 Cd1 N1 C1 -15.9(2) . . . . ? O3 Cd1 N1 C1 169.5(2) 2_665 . . . ? O2 Cd1 N1 C1 -44.2(3) . . . . ? O3 Cd1 N1 C1 -115.0(2) 1_445 . . . ? O4 Cd1 N1 C1 113.4(2) 2_665 . . . ? O1W Cd1 N1 C1 57.8(2) . . . . ? C6 Cd1 N1 C1 -23.5(3) . . . . ? C20 Cd1 N1 C1 142.5(2) 2_665 . . . ? O1 Cd1 N1 C2 156.6(2) . . . . ? O3 Cd1 N1 C2 -17.9(2) 2_665 . . . ? O2 Cd1 N1 C2 128.4(2) . . . . ? O3 Cd1 N1 C2 57.6(2) 1_445 . . . ? O4 Cd1 N1 C2 -74.1(2) 2_665 . . . ? O1W Cd1 N1 C2 -129.6(3) . . . . ? C6 Cd1 N1 C2 149.1(2) . . . . ? C20 Cd1 N1 C2 -45.0(2) 2_665 . . . ? N1 C1 N2 C3 0.6(3) . . . . ? N1 C1 N2 C4 175.8(2) . . . . ? C2 C3 N2 C1 -0.8(3) . . . . ? C2 C3 N2 C4 -176.2(2) . . . . ? C5 C4 N2 C1 12.5(4) . . . . ? C5 C4 N2 C3 -173.2(2) . . . . ? O2 C6 O1 Cd1 3.2(2) . . . . ? C7 C6 O1 Cd1 -174.16(18) . . . . ? N1 Cd1 O1 C6 -167.56(15) . . . . ? O3 Cd1 O1 C6 0.7(2) 2_665 . . . ? O2 Cd1 O1 C6 -1.77(14) . . . . ? O3 Cd1 O1 C6 -78.28(15) 1_445 . . . ? O4 Cd1 O1 C6 65.91(17) 2_665 . . . ? O1W Cd1 O1 C6 111.25(16) . . . . ? C20 Cd1 O1 C6 43.8(2) 2_665 . . . ? O1 C6 O2 Cd1 -3.2(2) . . . . ? C7 C6 O2 Cd1 174.18(18) . . . . ? N1 Cd1 O2 C6 35.9(2) . . . . ? O1 Cd1 O2 C6 1.80(14) . . . . ? O3 Cd1 O2 C6 -177.05(14) 2_665 . . . ? O3 Cd1 O2 C6 107.30(15) 1_445 . . . ? O4 Cd1 O2 C6 -123.67(15) 2_665 . . . ? O1W Cd1 O2 C6 -62.84(17) . . . . ? C20 Cd1 O2 C6 -150.26(15) 2_665 . . . ? O4 C20 O3 Cd1 -4.0(3) . . . 2_665 ? C18 C20 O3 Cd1 176.52(18) . . . 2_665 ? O4 C20 O3 Cd1 -144.6(3) . . . 1_665 ? C18 C20 O3 Cd1 35.9(5) . . . 1_665 ? Cd1 C20 O3 Cd1 -140.6(5) 2_665 . . 1_665 ? O3 C20 O4 Cd1 3.8(2) . . . 2_665 ? C18 C20 O4 Cd1 -176.72(19) . . . 2_665 ? N1 Cd1 O1W O1W' 117.9(7) . . . . ? O1 Cd1 O1W O1W' -137.3(7) . . . . ? O3 Cd1 O1W O1W' 15.2(7) 2_665 . . . ? O2 Cd1 O1W O1W' -87.1(7) . . . . ? O3 Cd1 O1W O1W' 160.4(6) 1_445 . . . ? O4 Cd1 O1W O1W' -2.8(6) 2_665 . . . ? C6 Cd1 O1W O1W' -111.4(7) . . . . ? C20 Cd1 O1W O1W' 5.4(7) 2_665 . . . ? C15 C14 N3 C13 177.8(3) . . . . ? C19 C14 N3 C13 -2.2(4) . . . . ? C10 C13 N3 C14 74.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.385 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.062 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 806751' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 N5 O4 Zn, H2 O' _chemical_formula_sum 'C25 H27 N5 O5 Zn' _chemical_formula_weight 542.89 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 pna21 _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.5487(16) _cell_length_b 9.8461(10) _cell_length_c 13.2847(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2426.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7187 _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_sigmaI/netI 0.2498 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 25.37 _reflns_number_total 3793 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water and amine were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.89+-0.02 \%A with U~iso~ = 1.5U~eq~(O) and N---H = 0.87+-0.02 \%A with U~iso~ = 1.5U~eq~(N). The distance of H1WA...HW1B was restrained to 1.44+-0.02 \%A. In order to give a reasonable C...H distance, the distance of C18...H5N was restrained to 2.00+-0.02 \%A. ; _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^)+(0.0000P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.624(14) _refine_ls_number_reflns 3793 _refine_ls_number_parameters 335 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0506 _refine_ls_wR_factor_gt 0.0398 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_restrained_S_all 0.569 _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 0.44547(3) 0.07558(7) -0.40373(6) 0.04389(17) Uani 1 1 d . . . C1 C 0.4108(3) -0.2258(6) -0.3873(5) 0.0451(16) Uani 1 1 d . . . H1 H 0.4243 -0.2295 -0.3199 0.054 Uiso 1 1 calc R . . C2 C 0.3854(3) -0.1514(7) -0.5325(5) 0.0583(19) Uani 1 1 d . . . H2 H 0.3783 -0.0933 -0.5868 0.070 Uiso 1 1 calc R . . C3 C 0.3763(3) -0.2869(9) -0.5353(5) 0.063(2) Uani 1 1 d . . . H3 H 0.3610 -0.3381 -0.5901 0.075 Uiso 1 1 calc R . . C4 C 0.3920(3) -0.4744(5) -0.4105(7) 0.0536(16) Uani 1 1 d . . . H4A H 0.4247 -0.4859 -0.3543 0.064 Uiso 1 1 calc R . . H4B H 0.4089 -0.5316 -0.4651 0.064 Uiso 1 1 calc R . . C5 C 0.3162(3) -0.5218(5) -0.3787(5) 0.0494(19) Uani 1 1 d . . . H5A H 0.2833 -0.5103 -0.4348 0.059 Uiso 1 1 calc R . . H5B H 0.3179 -0.6178 -0.3623 0.059 Uiso 1 1 calc R . . C6 C 0.2879(3) -0.4442(6) -0.2891(4) 0.0483(16) Uani 1 1 d . . . H6A H 0.2803 -0.3503 -0.3085 0.058 Uiso 1 1 calc R . . H6B H 0.3239 -0.4455 -0.2363 0.058 Uiso 1 1 calc R . . C7 C 0.2174(3) -0.5014(6) -0.2475(4) 0.0492(18) Uani 1 1 d . . . H7A H 0.2238 -0.5971 -0.2327 0.059 Uiso 1 1 calc R . . H7B H 0.2058 -0.4555 -0.1849 0.059 Uiso 1 1 calc R . . C8 C 0.0980(3) -0.5597(7) -0.3214(4) 0.0447(15) Uani 1 1 d . . . H8 H 0.0915 -0.6372 -0.2824 0.054 Uiso 1 1 calc R . . C9 C 0.0814(3) -0.4009(7) -0.4255(5) 0.068(2) Uani 1 1 d . . . H9 H 0.0607 -0.3455 -0.4742 0.082 Uiso 1 1 calc R . . C11 C 0.3745(5) 0.2159(7) -0.5446(5) 0.0524(19) Uani 1 1 d . . . C12 C 0.3549(4) 0.3039(7) -0.6314(5) 0.0396(17) Uani 1 1 d . . . C13 C 0.2847(3) 0.3481(7) -0.6419(5) 0.0510(18) Uani 1 1 d . . . H13 H 0.2497 0.3185 -0.5969 0.061 Uiso 1 1 calc R . . C14 C 0.2661(3) 0.4355(7) -0.7182(5) 0.0541(17) Uani 1 1 d . . . H14 H 0.2185 0.4636 -0.7247 0.065 Uiso 1 1 calc R . . C15 C 0.3174(4) 0.4821(8) -0.7857(5) 0.050(2) Uani 1 1 d . . . C16 C 0.3876(4) 0.4385(7) -0.7758(5) 0.051(2) Uani 1 1 d . . . H16 H 0.4228 0.4690 -0.8202 0.061 Uiso 1 1 calc R . . C17 C 0.4056(4) 0.3474(8) -0.6979(4) 0.053(2) Uani 1 1 d . . . H17 H 0.4528 0.3167 -0.6920 0.064 Uiso 1 1 calc R . . C18 C 0.3483(3) 0.6143(6) -0.9409(4) 0.057(2) Uani 1 1 d D . . H18A H 0.3923 0.6470 -0.9097 0.069 Uiso 1 1 calc R . . H18B H 0.3273 0.6897 -0.9775 0.069 Uiso 1 1 calc R . . C19 C 0.3680(4) 0.5071(7) -1.0146(5) 0.0431(18) Uani 1 1 d . . . C20 C 0.3249(4) 0.4018(7) -1.0395(4) 0.046(2) Uani 1 1 d . . . H20 H 0.2810 0.3930 -1.0063 0.055 Uiso 1 1 calc R . . C21 C 0.3428(3) 0.3056(7) -1.1125(5) 0.0488(19) Uani 1 1 d . . . H21 H 0.3119 0.2335 -1.1265 0.059 Uiso 1 1 calc R . . C22 C 0.4070(4) 0.3194(8) -1.1632(5) 0.0425(18) Uani 1 1 d . . . C23 C 0.4527(3) 0.4246(8) -1.1366(4) 0.0535(16) Uani 1 1 d . . . H23 H 0.4970 0.4333 -1.1687 0.064 Uiso 1 1 calc R . . C24 C 0.4335(4) 0.5172(6) -1.0627(5) 0.0530(18) Uani 1 1 d . . . H24 H 0.4651 0.5867 -1.0454 0.064 Uiso 1 1 calc R . . C25 C 0.4291(5) 0.2265(9) -1.2505(5) 0.055(2) Uani 1 1 d . . . C030 C 0.1472(3) -0.3817(6) -0.3844(6) 0.064(2) Uani 1 1 d . . . H030 H 0.1793 -0.3118 -0.3986 0.077 Uiso 1 1 calc R . . N1 N 0.4061(2) -0.1121(5) -0.4404(3) 0.0408(13) Uani 1 1 d . . . N2 N 0.3939(2) -0.3342(5) -0.4428(3) 0.0396(13) Uani 1 1 d . . . N3 N 0.1572(3) -0.4851(5) -0.3180(3) 0.0393(12) Uani 1 1 d . . . N4 N 0.0494(3) -0.5145(4) -0.3848(4) 0.0389(13) Uani 1 1 d . . . O1 O 0.4408(3) 0.1784(5) -0.5342(3) 0.0540(14) Uani 1 1 d . . . O2 O 0.3267(3) 0.1684(5) -0.4878(3) 0.0724(14) Uani 1 1 d . . . O3 O 0.4766(3) 0.2668(5) -1.3080(3) 0.0808(18) Uani 1 1 d . . . O4 O 0.3966(3) 0.1183(5) -1.2636(3) 0.0699(16) Uani 1 1 d . . . O1W O 0.5717(4) 0.1406(5) -0.6550(5) 0.124(2) Uani 1 1 d D . . H1WA H 0.536(3) 0.139(8) -0.610(5) 0.185 Uiso 1 1 d D . . H1WB H 0.584(5) 0.053(4) -0.667(7) 0.185 Uiso 1 1 d D . . N5 N 0.2988(3) 0.5756(7) -0.8616(4) 0.0642(18) Uani 1 1 d D . . H5N H 0.2543(9) 0.589(6) -0.874(3) 0.077 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0458(3) 0.0412(4) 0.0447(3) -0.0005(5) -0.0040(5) 0.0011(5) C1 0.054(3) 0.046(4) 0.035(4) 0.004(4) -0.008(3) -0.010(4) C2 0.081(5) 0.039(5) 0.055(5) 0.006(4) -0.025(4) -0.005(4) C3 0.072(5) 0.064(6) 0.051(5) -0.014(4) -0.006(4) 0.005(4) C4 0.061(4) 0.033(4) 0.067(4) -0.011(5) 0.009(5) 0.003(3) C5 0.051(4) 0.038(4) 0.060(6) -0.008(3) -0.005(3) -0.002(3) C6 0.042(4) 0.046(4) 0.057(4) -0.016(4) -0.012(3) 0.006(4) C7 0.044(4) 0.059(5) 0.045(4) 0.003(3) -0.002(4) -0.004(4) C8 0.042(4) 0.043(4) 0.049(4) 0.008(4) 0.002(3) -0.002(4) C9 0.054(4) 0.070(5) 0.079(7) 0.040(5) 0.000(4) 0.004(4) C11 0.085(6) 0.030(5) 0.043(4) -0.003(4) 0.000(5) -0.001(4) C12 0.037(4) 0.041(5) 0.040(4) -0.003(3) -0.015(3) 0.000(4) C13 0.058(5) 0.052(5) 0.042(4) 0.001(3) 0.006(4) -0.010(4) C14 0.039(4) 0.060(5) 0.064(4) -0.009(5) 0.005(4) 0.004(4) C15 0.058(5) 0.059(6) 0.032(4) -0.001(4) -0.012(4) 0.007(5) C16 0.044(5) 0.065(6) 0.044(4) 0.014(4) 0.006(3) 0.000(4) C17 0.047(5) 0.073(6) 0.038(5) -0.005(4) -0.009(4) 0.002(5) C18 0.091(5) 0.047(5) 0.034(4) 0.004(3) -0.005(4) 0.009(4) C19 0.059(5) 0.036(5) 0.034(4) 0.007(3) -0.006(4) -0.004(4) C20 0.048(5) 0.059(6) 0.031(4) 0.002(4) -0.002(3) 0.005(4) C21 0.049(5) 0.052(5) 0.046(4) 0.009(4) -0.009(4) -0.016(4) C22 0.038(4) 0.041(5) 0.049(4) 0.009(4) -0.003(4) 0.007(4) C23 0.041(4) 0.059(5) 0.061(4) 0.015(4) 0.000(3) 0.008(5) C24 0.057(5) 0.048(5) 0.054(4) -0.005(3) -0.013(4) -0.005(4) C25 0.070(7) 0.048(6) 0.046(5) -0.006(4) -0.021(4) 0.035(5) C030 0.034(3) 0.063(5) 0.094(6) 0.024(6) -0.011(5) -0.005(3) N1 0.049(3) 0.033(3) 0.041(3) 0.002(3) -0.013(2) 0.000(3) N2 0.045(3) 0.032(4) 0.041(3) 0.001(3) 0.001(2) -0.004(3) N3 0.042(3) 0.031(3) 0.044(3) 0.012(3) 0.002(3) -0.005(3) N4 0.050(3) 0.034(3) 0.033(4) 0.005(3) -0.003(3) -0.001(3) O1 0.050(3) 0.053(4) 0.059(3) 0.017(2) -0.006(3) 0.001(3) O2 0.090(4) 0.058(4) 0.069(3) 0.023(3) 0.013(3) 0.005(3) O3 0.108(5) 0.074(4) 0.060(3) 0.013(3) 0.017(3) 0.031(3) O4 0.077(4) 0.063(4) 0.070(3) -0.024(3) -0.014(3) 0.007(3) O1W 0.155(6) 0.099(5) 0.117(4) 0.022(4) 0.067(4) 0.025(5) N5 0.057(4) 0.084(5) 0.052(4) -0.004(4) -0.015(3) 0.027(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 Zn1 O1 2.009(4) . ? Zn1 N1 2.046(5) . ? Zn1 N4 2.035(5) 4_545 ? Zn1 O4 2.113(5) 1_556 ? Zn1 O3 2.344(5) 1_556 ? Zn1 C25 2.538(8) 1_556 ? C1 N1 1.326(6) . ? C1 N2 1.335(6) . ? C1 H1 0.9300 . ? C2 C3 1.345(7) . ? C2 N1 1.339(6) . ? C2 H2 0.9300 . ? C3 N2 1.354(7) . ? C3 H3 0.9300 . ? C4 N2 1.446(6) . ? C4 C5 1.540(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.509(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.467(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.312(6) . ? C8 N3 1.321(6) . ? C8 H8 0.9300 . ? C9 C030 1.351(7) . ? C9 N4 1.377(6) . ? C9 H9 0.9300 . ? C11 O2 1.255(7) . ? C11 O1 1.292(8) . ? C11 C12 1.487(8) . ? C12 C17 1.360(8) . ? C12 C13 1.380(8) . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C14 C15 1.384(8) . ? C14 H14 0.9300 . ? C15 C16 1.377(8) . ? C15 N5 1.409(8) . ? C16 C17 1.410(8) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N5 1.449(7) . ? C18 C19 1.485(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.350(8) . ? C19 C24 1.375(8) . ? C20 C21 1.396(8) . ? C20 H20 0.9300 . ? C21 C22 1.375(8) . ? C21 H21 0.9300 . ? C22 C23 1.385(8) . ? C22 C25 1.534(10) . ? C23 C24 1.387(8) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O3 1.232(9) . ? C25 O4 1.236(8) . ? C25 Zn1 2.538(8) 1_554 ? C030 N3 1.359(7) . ? C030 H030 0.9300 . ? N4 Zn1 2.035(5) 4_445 ? O3 Zn1 2.344(5) 1_554 ? O4 Zn1 2.113(5) 1_554 ? O1W H1WA 0.89(2) . ? O1W H1WB 0.91(2) . ? N5 H5N 0.853(18) . ? 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 N1 103.53(18) . . ? O1 Zn1 N4 107.26(18) . 4_545 ? N1 Zn1 N4 95.79(17) . 4_545 ? O1 Zn1 O4 129.89(18) . 1_556 ? N1 Zn1 O4 103.70(18) . 1_556 ? N4 Zn1 O4 110.85(19) 4_545 1_556 ? O1 Zn1 O3 94.24(18) . 1_556 ? N1 Zn1 O3 160.51(17) . 1_556 ? N4 Zn1 O3 86.37(17) 4_545 1_556 ? O4 Zn1 O3 57.84(17) 1_556 1_556 ? O1 Zn1 C25 113.1(2) . 1_556 ? N1 Zn1 C25 132.6(2) . 1_556 ? N4 Zn1 C25 100.8(2) 4_545 1_556 ? O4 Zn1 C25 29.0(2) 1_556 1_556 ? O3 Zn1 C25 28.9(2) 1_556 1_556 ? N1 C1 N2 111.4(5) . . ? N1 C1 H1 124.3 . . ? N2 C1 H1 124.3 . . ? C3 C2 N1 110.4(6) . . ? C3 C2 H2 124.8 . . ? N1 C2 H2 124.8 . . ? C2 C3 N2 106.6(6) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 C5 113.2(4) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 112.4(5) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 113.4(5) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N3 C7 C6 112.4(5) . . ? N3 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? N3 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? N4 C8 N3 113.8(6) . . ? N4 C8 H8 123.1 . . ? N3 C8 H8 123.1 . . ? C030 C9 N4 110.1(6) . . ? C030 C9 H9 124.9 . . ? N4 C9 H9 124.9 . . ? O2 C11 O1 120.1(6) . . ? O2 C11 C12 120.8(7) . . ? O1 C11 C12 118.8(7) . . ? C17 C12 C13 119.1(6) . . ? C17 C12 C11 121.3(6) . . ? C13 C12 C11 119.5(7) . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.9(6) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.0(6) . . ? C16 C15 N5 120.2(7) . . ? C14 C15 N5 120.8(7) . . ? C15 C16 C17 119.5(6) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 120.9(6) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? N5 C18 C19 116.7(6) . . ? N5 C18 H18A 108.1 . . ? C19 C18 H18A 108.1 . . ? N5 C18 H18B 108.1 . . ? C19 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C20 C19 C24 117.7(7) . . ? C20 C19 C18 124.2(7) . . ? C24 C19 C18 118.1(7) . . ? C19 C20 C21 123.4(6) . . ? C19 C20 H20 118.3 . . ? C21 C20 H20 118.3 . . ? C22 C21 C20 118.6(6) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 118.7(7) . . ? C21 C22 C25 122.9(7) . . ? C23 C22 C25 118.4(6) . . ? C24 C23 C22 121.0(6) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C19 120.6(6) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? O3 C25 O4 122.6(8) . . ? O3 C25 C22 117.9(8) . . ? O4 C25 C22 119.3(8) . . ? O3 C25 Zn1 66.8(4) . 1_554 ? O4 C25 Zn1 56.0(4) . 1_554 ? C22 C25 Zn1 171.0(5) . 1_554 ? C9 C030 N3 106.3(6) . . ? C9 C030 H030 126.9 . . ? N3 C030 H030 126.9 . . ? C1 N1 C2 105.1(5) . . ? C1 N1 Zn1 127.7(4) . . ? C2 N1 Zn1 125.5(4) . . ? C1 N2 C3 106.5(5) . . ? C1 N2 C4 127.3(6) . . ? C3 N2 C4 126.2(6) . . ? C8 N3 C030 106.4(5) . . ? C8 N3 C7 126.4(5) . . ? C030 N3 C7 126.8(5) . . ? C8 N4 C9 103.4(5) . . ? C8 N4 Zn1 129.1(4) . 4_445 ? C9 N4 Zn1 126.8(4) . 4_445 ? C11 O1 Zn1 106.1(4) . . ? C25 O3 Zn1 84.3(5) . 1_554 ? C25 O4 Zn1 95.0(5) . 1_554 ? H1WA O1W H1WB 106(3) . . ? C15 N5 C18 122.5(5) . . ? C15 N5 H5N 119(3) . . ? C18 N5 H5N 115(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -1.8(8) . . . . ? N2 C4 C5 C6 -62.6(8) . . . . ? C4 C5 C6 C7 -172.4(5) . . . . ? C5 C6 C7 N3 -66.8(6) . . . . ? O2 C11 C12 C17 -174.9(7) . . . . ? O1 C11 C12 C17 -1.5(10) . . . . ? O2 C11 C12 C13 8.5(10) . . . . ? O1 C11 C12 C13 -178.1(6) . . . . ? C17 C12 C13 C14 -0.3(10) . . . . ? C11 C12 C13 C14 176.4(6) . . . . ? C12 C13 C14 C15 -0.6(10) . . . . ? C13 C14 C15 C16 0.6(10) . . . . ? C13 C14 C15 N5 -177.6(6) . . . . ? C14 C15 C16 C17 0.3(10) . . . . ? N5 C15 C16 C17 178.5(6) . . . . ? C13 C12 C17 C16 1.2(10) . . . . ? C11 C12 C17 C16 -175.5(6) . . . . ? C15 C16 C17 C12 -1.2(10) . . . . ? N5 C18 C19 C20 28.2(9) . . . . ? N5 C18 C19 C24 -153.4(5) . . . . ? C24 C19 C20 C21 -1.5(10) . . . . ? C18 C19 C20 C21 176.9(6) . . . . ? C19 C20 C21 C22 -1.2(10) . . . . ? C20 C21 C22 C23 3.0(9) . . . . ? C20 C21 C22 C25 -174.9(6) . . . . ? C21 C22 C23 C24 -2.2(9) . . . . ? C25 C22 C23 C24 175.8(5) . . . . ? C22 C23 C24 C19 -0.6(10) . . . . ? C20 C19 C24 C23 2.3(10) . . . . ? C18 C19 C24 C23 -176.1(5) . . . . ? C21 C22 C25 O3 160.9(6) . . . . ? C23 C22 C25 O3 -17.0(9) . . . . ? C21 C22 C25 O4 -15.5(10) . . . . ? C23 C22 C25 O4 166.7(6) . . . . ? C21 C22 C25 Zn1 41(4) . . . 1_554 ? C23 C22 C25 Zn1 -137(4) . . . 1_554 ? N4 C9 C030 N3 0.7(8) . . . . ? N2 C1 N1 C2 0.0(7) . . . . ? N2 C1 N1 Zn1 -166.0(3) . . . . ? C3 C2 N1 C1 1.1(7) . . . . ? C3 C2 N1 Zn1 167.5(4) . . . . ? O1 Zn1 N1 C1 165.4(5) . . . . ? N4 Zn1 N1 C1 56.0(5) 4_545 . . . ? O4 Zn1 N1 C1 -57.1(5) 1_556 . . . ? O3 Zn1 N1 C1 -39.5(8) 1_556 . . . ? C25 Zn1 N1 C1 -54.4(6) 1_556 . . . ? O1 Zn1 N1 C2 2.0(5) . . . . ? N4 Zn1 N1 C2 -107.3(5) 4_545 . . . ? O4 Zn1 N1 C2 139.6(5) 1_556 . . . ? O3 Zn1 N1 C2 157.2(5) 1_556 . . . ? C25 Zn1 N1 C2 142.3(5) 1_556 . . . ? N1 C1 N2 C3 -1.1(7) . . . . ? N1 C1 N2 C4 -179.0(5) . . . . ? C2 C3 N2 C1 1.7(7) . . . . ? C2 C3 N2 C4 179.7(5) . . . . ? C5 C4 N2 C1 95.3(7) . . . . ? C5 C4 N2 C3 -82.3(8) . . . . ? N4 C8 N3 C030 0.0(7) . . . . ? N4 C8 N3 C7 173.2(5) . . . . ? C9 C030 N3 C8 -0.4(7) . . . . ? C9 C030 N3 C7 -173.6(6) . . . . ? C6 C7 N3 C8 155.5(5) . . . . ? C6 C7 N3 C030 -32.6(8) . . . . ? N3 C8 N4 C9 0.4(7) . . . . ? N3 C8 N4 Zn1 -170.5(4) . . . 4_445 ? C030 C9 N4 C8 -0.7(7) . . . . ? C030 C9 N4 Zn1 170.5(4) . . . 4_445 ? O2 C11 O1 Zn1 -11.1(8) . . . . ? C12 C11 O1 Zn1 175.5(5) . . . . ? N1 Zn1 O1 C11 79.4(4) . . . . ? N4 Zn1 O1 C11 180.0(4) 4_545 . . . ? O4 Zn1 O1 C11 -41.8(5) 1_556 . . . ? O3 Zn1 O1 C11 -92.5(5) 1_556 . . . ? C25 Zn1 O1 C11 -69.9(5) 1_556 . . . ? O4 C25 O3 Zn1 4.6(7) . . . 1_554 ? C22 C25 O3 Zn1 -171.6(6) . . . 1_554 ? O3 C25 O4 Zn1 -5.1(8) . . . 1_554 ? C22 C25 O4 Zn1 171.0(5) . . . 1_554 ? C16 C15 N5 C18 9.4(11) . . . . ? C14 C15 N5 C18 -172.4(6) . . . . ? C19 C18 N5 C15 67.2(7) . . . . ? 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 H1WB O4 0.91(2) 2.15(4) 2.987(8) 153(8) 2_655 N5 H5N O2 0.853(18) 2.27(3) 3.010(7) 146(3) 3_554 O1W H1WA O1 0.89(2) 2.07(3) 2.935(7) 163(8) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.206 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.043 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 806752' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 Co N5 O5' _chemical_formula_weight 536.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.3946(7) _cell_length_b 9.8739(3) _cell_length_c 13.2948(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2414.69(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 0.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12642 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 29.71 _reflns_number_total 5259 _reflns_number_gt 2884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined with distance restraints of O---H = 0.85+-0.02 \%A. The distance of H1WA...HW1B was restrained to 1.44+-0.05 \%A. ; _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^)+(0.0107P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.542(11) _refine_ls_number_reflns 5259 _refine_ls_number_parameters 335 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0478 _refine_ls_wR_factor_gt 0.0436 _refine_ls_goodness_of_fit_ref 0.807 _refine_ls_restrained_S_all 0.807 _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 Co1 Co 0.059638(16) 0.07863(3) 0.27775(3) 0.03993(9) Uani 1 1 d . . . C1 C 0.09292(13) -0.2241(3) 0.2662(3) 0.0464(7) Uani 1 1 d . . . H1 H 0.0815 -0.2276 0.1981 0.056 Uiso 1 1 calc R . . C2 C 0.11530(17) -0.1516(3) 0.4120(2) 0.0590(9) Uani 1 1 d . . . H2 H 0.1224 -0.0939 0.4664 0.071 Uiso 1 1 calc R . . C3 C 0.12235(17) -0.2871(4) 0.4157(3) 0.0594(9) Uani 1 1 d . . . H3 H 0.1349 -0.3390 0.4714 0.071 Uiso 1 1 calc R . . C4 C 0.10936(13) -0.4726(2) 0.2878(3) 0.0514(8) Uani 1 1 d . . . H4A H 0.0760 -0.4832 0.2318 0.062 Uiso 1 1 calc R . . H4B H 0.0927 -0.5308 0.3418 0.062 Uiso 1 1 calc R . . C5 C 0.18509(13) -0.5183(2) 0.2549(2) 0.0466(8) Uani 1 1 d . . . H5A H 0.2186 -0.5049 0.3103 0.056 Uiso 1 1 calc R . . H5B H 0.1837 -0.6145 0.2401 0.056 Uiso 1 1 calc R . . C6 C 0.21328(14) -0.4446(3) 0.1645(2) 0.0428(7) Uani 1 1 d . . . H6A H 0.2206 -0.3502 0.1821 0.051 Uiso 1 1 calc R . . H6B H 0.1768 -0.4480 0.1119 0.051 Uiso 1 1 calc R . . C7 C 0.28355(13) -0.5011(3) 0.1239(2) 0.0445(7) Uani 1 1 d . . . H7A H 0.2769 -0.5966 0.1095 0.053 Uiso 1 1 calc R . . H7B H 0.2949 -0.4560 0.0610 0.053 Uiso 1 1 calc R . . C10 C 0.35573(15) -0.3837(3) 0.2589(3) 0.0599(10) Uani 1 1 d . . . H8 H 0.3230 -0.3154 0.2750 0.072 Uiso 1 1 calc R . . C8 C 0.40546(15) -0.5602(3) 0.1935(2) 0.0428(7) Uani 1 1 d . . . H9 H 0.4121 -0.6370 0.1541 0.051 Uiso 1 1 calc R . . C9 C 0.42335(14) -0.4004(3) 0.2976(3) 0.0612(10) Uani 1 1 d . . . H10 H 0.4451 -0.3440 0.3449 0.073 Uiso 1 1 calc R . . C11 C 0.07523(17) 0.2285(3) 0.1259(3) 0.0436(8) Uani 1 1 d . . . C12 C 0.09488(16) 0.3175(3) 0.0391(2) 0.0381(7) Uani 1 1 d . . . C13 C 0.04942(15) 0.4260(3) 0.0138(2) 0.0484(7) Uani 1 1 d . . . H13 H 0.0057 0.4372 0.0478 0.058 Uiso 1 1 calc R . . C14 C 0.06814(15) 0.5153(3) -0.0595(2) 0.0472(7) Uani 1 1 d . . . H14 H 0.0361 0.5846 -0.0764 0.057 Uiso 1 1 calc R . . C15 C 0.13378(16) 0.5055(3) -0.1096(2) 0.0413(8) Uani 1 1 d . . . C16 C 0.17896(17) 0.3970(3) -0.0872(2) 0.0476(8) Uani 1 1 d . . . H16 H 0.2228 0.3866 -0.1213 0.057 Uiso 1 1 calc R . . C17 C 0.15869(15) 0.3030(3) -0.0134(2) 0.0422(7) Uani 1 1 d . . . H17 H 0.1889 0.2297 0.0002 0.051 Uiso 1 1 calc R . . C18 C 0.15355(17) 0.6113(3) -0.1844(2) 0.0550(9) Uani 1 1 d . . . H18A H 0.1090 0.6445 -0.2147 0.066 Uiso 1 1 calc R . . H18B H 0.1753 0.6865 -0.1483 0.066 Uiso 1 1 calc R . . C19 C 0.18196(17) 0.4810(3) -0.3399(2) 0.0408(7) Uani 1 1 d . . . C20 C 0.11136(15) 0.4357(3) -0.3482(2) 0.0441(7) Uani 1 1 d . . . H20 H 0.0763 0.4650 -0.3027 0.053 Uiso 1 1 calc R . . C21 C 0.09250(15) 0.3465(3) -0.4244(2) 0.0429(8) Uani 1 1 d . . . H21 H 0.0448 0.3156 -0.4285 0.052 Uiso 1 1 calc R . . C22 C 0.14235(15) 0.3025(3) -0.4940(2) 0.0359(7) Uani 1 1 d . . . C23 C 0.21362(15) 0.3467(3) -0.4851(2) 0.0450(8) Uani 1 1 d . . . H23 H 0.2485 0.3165 -0.5305 0.054 Uiso 1 1 calc R . . C24 C 0.23326(14) 0.4348(3) -0.4095(2) 0.0451(7) Uani 1 1 d . . . H24 H 0.2812 0.4639 -0.4047 0.054 Uiso 1 1 calc R . . C25 C 0.11982(18) 0.2117(3) -0.5792(2) 0.0435(8) Uani 1 1 d . . . N1 N 0.09650(11) -0.1105(2) 0.31855(17) 0.0396(6) Uani 1 1 d . . . N2 N 0.10748(11) -0.3328(2) 0.32170(19) 0.0413(6) Uani 1 1 d . . . N3 N 0.34497(12) -0.4858(2) 0.19220(17) 0.0412(6) Uani 1 1 d . . . N4 N 0.45450(11) -0.51355(19) 0.25599(18) 0.0434(7) Uani 1 1 d . . . O1 O 0.10741(11) 0.11624(19) 0.13710(14) 0.0518(6) Uani 1 1 d . . . O2 O 0.02923(10) 0.26732(18) 0.18888(15) 0.0533(5) Uani 1 1 d . . . O3 O 0.05292(11) 0.17670(19) -0.58585(15) 0.0531(6) Uani 1 1 d . . . O4 O 0.16481(11) 0.17266(19) -0.64155(16) 0.0575(6) Uani 1 1 d . . . N5 N 0.20304(15) 0.5726(3) -0.2656(2) 0.0644(8) Uani 1 1 d . . . H5N H 0.2421(15) 0.586(3) -0.244(3) 0.077 Uiso 1 1 d . . . O1W O 0.07950(17) -0.1426(3) 0.0278(2) 0.0997(10) Uani 1 1 d D . . H1WB H 0.054(2) -0.144(4) -0.026(2) 0.150 Uiso 1 1 d D . . H1WA H 0.075(3) -0.068(3) 0.060(3) 0.150 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.04045(17) 0.03619(17) 0.04314(19) -0.0025(2) -0.0024(3) 0.00006(18) C1 0.0510(15) 0.0449(16) 0.0433(19) -0.0036(19) -0.0084(19) 0.0076(14) C2 0.082(2) 0.053(2) 0.042(2) -0.0077(19) -0.0176(18) 0.0009(18) C3 0.076(2) 0.061(2) 0.041(2) 0.005(2) -0.0181(18) -0.0023(18) C4 0.0480(16) 0.0341(14) 0.072(2) 0.008(2) 0.0121(19) -0.0062(11) C5 0.0451(15) 0.0377(14) 0.057(3) 0.0031(17) 0.0028(15) 0.0011(12) C6 0.0383(16) 0.0444(17) 0.0457(18) 0.0060(16) -0.0009(14) 0.0002(14) C7 0.0390(18) 0.0494(17) 0.0452(19) -0.0049(16) -0.0026(15) -0.0013(14) C10 0.0437(17) 0.0551(19) 0.081(3) -0.022(2) -0.0028(19) 0.0086(13) C8 0.0441(17) 0.0366(16) 0.0478(18) -0.0071(16) 0.0001(15) 0.0024(15) C9 0.0492(18) 0.058(2) 0.077(3) -0.027(2) -0.0056(18) 0.0042(14) C11 0.043(2) 0.041(2) 0.047(2) -0.0043(17) -0.0071(17) -0.0101(17) C12 0.0428(18) 0.0349(17) 0.0367(19) -0.0059(16) -0.0025(15) -0.0018(15) C13 0.0431(17) 0.0455(17) 0.0567(19) -0.0010(18) 0.0035(15) -0.0005(16) C14 0.0497(19) 0.0421(17) 0.050(2) 0.0026(16) -0.0133(17) 0.0023(15) C15 0.047(2) 0.0412(19) 0.0353(19) -0.0091(16) -0.0045(15) -0.0035(16) C16 0.0480(19) 0.048(2) 0.047(2) -0.0130(18) 0.0007(16) -0.0034(16) C17 0.0485(19) 0.0348(17) 0.043(2) -0.0043(16) -0.0039(16) 0.0066(14) C18 0.079(2) 0.0429(19) 0.043(2) -0.0067(16) -0.0049(18) -0.0088(16) C19 0.0484(19) 0.0404(18) 0.0335(19) 0.0075(16) -0.0098(16) -0.0071(16) C20 0.0420(18) 0.061(2) 0.0299(17) -0.0037(17) -0.0004(14) 0.0006(16) C21 0.0345(17) 0.054(2) 0.040(2) -0.0022(17) -0.0042(15) -0.0060(16) C22 0.0383(17) 0.0371(17) 0.0323(17) 0.0041(14) -0.0042(14) 0.0042(14) C23 0.0389(18) 0.0450(18) 0.051(2) 0.0045(16) 0.0022(15) 0.0038(15) C24 0.0361(16) 0.0506(18) 0.0486(19) 0.0040(18) -0.0026(15) -0.0133(15) C25 0.055(2) 0.0320(17) 0.044(2) 0.0106(17) 0.0005(17) -0.0039(16) N1 0.0439(13) 0.0361(14) 0.0387(15) -0.0010(12) -0.0071(10) -0.0004(10) N2 0.0373(13) 0.0353(14) 0.0514(17) 0.0061(13) 0.0017(12) 0.0030(11) N3 0.0389(14) 0.0367(13) 0.0479(15) -0.0069(13) 0.0018(12) 0.0006(11) N4 0.0440(13) 0.0379(12) 0.048(2) -0.0056(12) -0.0065(13) 0.0019(10) O1 0.0604(14) 0.0424(13) 0.0525(14) 0.0044(11) 0.0030(11) 0.0063(11) O2 0.0625(14) 0.0425(12) 0.0551(14) -0.0027(11) 0.0132(12) -0.0033(10) O3 0.0459(13) 0.0619(14) 0.0516(14) -0.0162(12) -0.0052(11) -0.0026(11) O4 0.0645(13) 0.0517(14) 0.0564(15) -0.0165(11) 0.0180(12) -0.0082(11) N5 0.0638(19) 0.0751(18) 0.0543(19) -0.0031(16) -0.0130(17) -0.0296(17) O1W 0.119(2) 0.0803(19) 0.100(2) 0.0057(18) -0.0541(19) -0.0098(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 Co1 N4 2.058(2) 4_445 ? Co1 N1 2.059(2) . ? Co1 O3 2.0594(19) 1_556 ? Co1 O1 2.0993(19) . ? Co1 O2 2.2759(19) . ? Co1 O4 2.399(2) 1_556 ? Co1 C11 2.520(3) . ? C1 N1 1.322(3) . ? C1 N2 1.329(3) . ? C1 H1 0.9300 . ? C2 C3 1.346(4) . ? C2 N1 1.352(3) . ? C2 H2 0.9300 . ? C3 N2 1.356(3) . ? C3 H3 0.9300 . ? C4 N2 1.453(3) . ? C4 C5 1.528(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.497(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.508(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.457(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C10 C9 1.356(4) . ? C10 N3 1.357(3) . ? C10 H8 0.9300 . ? C8 N4 1.310(3) . ? C8 N3 1.333(3) . ? C8 H9 0.9300 . ? C9 N4 1.373(3) . ? C9 H10 0.9300 . ? C11 O2 1.251(3) . ? C11 O1 1.265(3) . ? C11 C12 1.495(4) . ? C12 C17 1.373(4) . ? C12 C13 1.400(4) . ? C13 C14 1.359(4) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 C16 1.388(4) . ? C15 C18 1.488(4) . ? C16 C17 1.401(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N5 1.463(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.378(4) . ? C19 N5 1.394(4) . ? C19 C24 1.398(4) . ? C20 C21 1.387(4) . ? C20 H20 0.9300 . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C22 C23 1.387(3) . ? C22 C25 1.502(4) . ? C23 C24 1.378(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O4 1.234(3) . ? C25 O3 1.281(3) . ? N4 Co1 2.058(2) 4_545 ? O3 Co1 2.0594(19) 1_554 ? O4 Co1 2.399(2) 1_554 ? N5 H5N 0.78(3) . ? O1W H1WB 0.851(18) . ? O1W H1WA 0.861(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Co1 N1 93.63(8) 4_445 . ? N4 Co1 O3 102.37(8) 4_445 1_556 ? N1 Co1 O3 102.37(9) . 1_556 ? N4 Co1 O1 108.87(9) 4_445 . ? N1 Co1 O1 104.90(8) . . ? O3 Co1 O1 136.58(8) 1_556 . ? N4 Co1 O2 87.23(8) 4_445 . ? N1 Co1 O2 163.72(9) . . ? O3 Co1 O2 93.29(8) 1_556 . ? O1 Co1 O2 59.71(7) . . ? N4 Co1 O4 160.28(8) 4_445 1_556 ? N1 Co1 O4 88.14(8) . 1_556 ? O3 Co1 O4 58.18(7) 1_556 1_556 ? O1 Co1 O4 89.56(8) . 1_556 ? O2 Co1 O4 96.52(7) . 1_556 ? N4 Co1 C11 100.23(9) 4_445 . ? N1 Co1 C11 134.91(10) . . ? O3 Co1 C11 115.88(9) 1_556 . ? O1 Co1 C11 30.07(8) . . ? O2 Co1 C11 29.69(8) . . ? O4 Co1 C11 92.26(8) 1_556 . ? N1 C1 N2 112.5(3) . . ? N1 C1 H1 123.8 . . ? N2 C1 H1 123.8 . . ? C3 C2 N1 110.9(3) . . ? C3 C2 H2 124.6 . . ? N1 C2 H2 124.6 . . ? C2 C3 N2 106.1(3) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N2 C4 C5 113.02(19) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 113.7(2) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 113.8(2) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? N3 C7 C6 113.8(2) . . ? N3 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C10 N3 107.0(2) . . ? C9 C10 H8 126.5 . . ? N3 C10 H8 126.5 . . ? N4 C8 N3 112.9(2) . . ? N4 C8 H9 123.6 . . ? N3 C8 H9 123.6 . . ? C10 C9 N4 109.1(3) . . ? C10 C9 H10 125.4 . . ? N4 C9 H10 125.4 . . ? O2 C11 O1 120.4(3) . . ? O2 C11 C12 120.0(3) . . ? O1 C11 C12 119.5(3) . . ? O2 C11 Co1 64.30(16) . . ? O1 C11 Co1 56.25(15) . . ? C12 C11 Co1 172.5(2) . . ? C17 C12 C13 117.9(3) . . ? C17 C12 C11 122.5(3) . . ? C13 C12 C11 119.4(3) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C15 C16 118.3(3) . . ? C14 C15 C18 119.1(3) . . ? C16 C15 C18 122.6(3) . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 121.0(3) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? N5 C18 C15 117.5(3) . . ? N5 C18 H18A 107.9 . . ? C15 C18 H18A 107.9 . . ? N5 C18 H18B 107.9 . . ? C15 C18 H18B 107.9 . . ? H18A C18 H18B 107.2 . . ? C20 C19 N5 122.0(3) . . ? C20 C19 C24 118.5(3) . . ? N5 C19 C24 119.5(3) . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 121.8(3) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 118.3(3) . . ? C21 C22 C25 120.8(3) . . ? C23 C22 C25 120.9(3) . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 120.8(2) . . ? C23 C24 H24 119.6 . . ? C19 C24 H24 119.6 . . ? O4 C25 O3 120.9(3) . . ? O4 C25 C22 120.6(3) . . ? O3 C25 C22 118.6(3) . . ? C1 N1 C2 104.0(2) . . ? C1 N1 Co1 127.91(19) . . ? C2 N1 Co1 126.8(2) . . ? C1 N2 C3 106.5(2) . . ? C1 N2 C4 126.8(3) . . ? C3 N2 C4 126.7(3) . . ? C8 N3 C10 106.2(2) . . ? C8 N3 C7 126.7(2) . . ? C10 N3 C7 126.7(2) . . ? C8 N4 C9 104.8(2) . . ? C8 N4 Co1 128.78(19) . 4_545 ? C9 N4 Co1 126.13(18) . 4_545 ? C11 O1 Co1 93.68(19) . . ? C11 O2 Co1 86.01(18) . . ? C25 O3 Co1 97.50(18) . 1_554 ? C25 O4 Co1 83.15(17) . 1_554 ? C19 N5 C18 121.3(2) . . ? C19 N5 H5N 128(3) . . ? C18 N5 H5N 105(3) . . ? H1WB O1W H1WA 112(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 0.0(4) . . . . ? N2 C4 C5 C6 -64.6(4) . . . . ? C4 C5 C6 C7 -172.6(2) . . . . ? C5 C6 C7 N3 -65.7(3) . . . . ? N3 C10 C9 N4 -0.6(4) . . . . ? N4 Co1 C11 O2 65.45(17) 4_445 . . . ? N1 Co1 C11 O2 171.16(14) . . . . ? O3 Co1 C11 O2 -43.78(19) 1_556 . . . ? O1 Co1 C11 O2 175.6(3) . . . . ? O4 Co1 C11 O2 -99.22(16) 1_556 . . . ? N4 Co1 C11 O1 -110.13(16) 4_445 . . . ? N1 Co1 C11 O1 -4.4(2) . . . . ? O3 Co1 C11 O1 140.64(15) 1_556 . . . ? O2 Co1 C11 O1 -175.6(3) . . . . ? O4 Co1 C11 O1 85.21(16) 1_556 . . . ? N4 Co1 C11 C12 -168.2(18) 4_445 . . . ? N1 Co1 C11 C12 -62.5(18) . . . . ? O3 Co1 C11 C12 82.6(18) 1_556 . . . ? O1 Co1 C11 C12 -58.0(17) . . . . ? O2 Co1 C11 C12 126.4(18) . . . . ? O4 Co1 C11 C12 27.2(18) 1_556 . . . ? O2 C11 C12 C17 159.0(3) . . . . ? O1 C11 C12 C17 -18.3(4) . . . . ? Co1 C11 C12 C17 35.9(19) . . . . ? O2 C11 C12 C13 -16.5(4) . . . . ? O1 C11 C12 C13 166.2(3) . . . . ? Co1 C11 C12 C13 -139.6(17) . . . . ? C17 C12 C13 C14 -0.8(4) . . . . ? C11 C12 C13 C14 174.9(2) . . . . ? C12 C13 C14 C15 -2.3(4) . . . . ? C13 C14 C15 C16 3.5(4) . . . . ? C13 C14 C15 C18 -176.0(2) . . . . ? C14 C15 C16 C17 -1.8(4) . . . . ? C18 C15 C16 C17 177.7(2) . . . . ? C13 C12 C17 C16 2.5(4) . . . . ? C11 C12 C17 C16 -173.1(3) . . . . ? C15 C16 C17 C12 -1.2(4) . . . . ? C14 C15 C18 N5 -153.4(3) . . . . ? C16 C15 C18 N5 27.1(4) . . . . ? N5 C19 C20 C21 178.8(3) . . . . ? C24 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C20 C21 C22 C23 1.7(4) . . . . ? C20 C21 C22 C25 -176.7(3) . . . . ? C21 C22 C23 C24 -1.4(4) . . . . ? C25 C22 C23 C24 177.0(3) . . . . ? C22 C23 C24 C19 0.3(4) . . . . ? C20 C19 C24 C23 0.4(4) . . . . ? N5 C19 C24 C23 -178.5(3) . . . . ? C21 C22 C25 O4 179.9(3) . . . . ? C23 C22 C25 O4 1.5(4) . . . . ? C21 C22 C25 O3 0.4(4) . . . . ? C23 C22 C25 O3 -178.0(3) . . . . ? N2 C1 N1 C2 0.7(3) . . . . ? N2 C1 N1 Co1 -166.65(16) . . . . ? C3 C2 N1 C1 -0.4(3) . . . . ? C3 C2 N1 Co1 167.2(2) . . . . ? N4 Co1 N1 C1 57.4(2) 4_445 . . . ? O3 Co1 N1 C1 160.9(2) 1_556 . . . ? O1 Co1 N1 C1 -53.3(2) . . . . ? O2 Co1 N1 C1 -35.2(4) . . . . ? O4 Co1 N1 C1 -142.3(2) 1_556 . . . ? C11 Co1 N1 C1 -51.0(3) . . . . ? N4 Co1 N1 C2 -107.3(2) 4_445 . . . ? O3 Co1 N1 C2 -3.8(2) 1_556 . . . ? O1 Co1 N1 C2 142.1(2) . . . . ? O2 Co1 N1 C2 160.1(2) . . . . ? O4 Co1 N1 C2 53.0(2) 1_556 . . . ? C11 Co1 N1 C2 144.4(2) . . . . ? N1 C1 N2 C3 -0.8(3) . . . . ? N1 C1 N2 C4 -179.0(2) . . . . ? C2 C3 N2 C1 0.5(3) . . . . ? C2 C3 N2 C4 178.7(2) . . . . ? C5 C4 N2 C1 92.2(3) . . . . ? C5 C4 N2 C3 -85.7(4) . . . . ? N4 C8 N3 C10 -0.1(3) . . . . ? N4 C8 N3 C7 173.0(2) . . . . ? C9 C10 N3 C8 0.4(3) . . . . ? C9 C10 N3 C7 -172.6(3) . . . . ? C6 C7 N3 C8 156.7(2) . . . . ? C6 C7 N3 C10 -31.7(4) . . . . ? N3 C8 N4 C9 -0.3(3) . . . . ? N3 C8 N4 Co1 -173.98(17) . . . 4_545 ? C10 C9 N4 C8 0.6(3) . . . . ? C10 C9 N4 Co1 174.5(2) . . . 4_545 ? O2 C11 O1 Co1 -4.6(3) . . . . ? C12 C11 O1 Co1 172.7(2) . . . . ? N4 Co1 O1 C11 77.54(17) 4_445 . . . ? N1 Co1 O1 C11 176.76(16) . . . . ? O3 Co1 O1 C11 -56.1(2) 1_556 . . . ? O2 Co1 O1 C11 2.53(16) . . . . ? O4 Co1 O1 C11 -95.28(16) 1_556 . . . ? O1 C11 O2 Co1 4.3(3) . . . . ? C12 C11 O2 Co1 -173.0(2) . . . . ? N4 Co1 O2 C11 -116.34(17) 4_445 . . . ? N1 Co1 O2 C11 -22.9(4) . . . . ? O3 Co1 O2 C11 141.42(17) 1_556 . . . ? O1 Co1 O2 C11 -2.56(16) . . . . ? O4 Co1 O2 C11 83.09(17) 1_556 . . . ? O4 C25 O3 Co1 -6.0(3) . . . 1_554 ? C22 C25 O3 Co1 173.6(2) . . . 1_554 ? O3 C25 O4 Co1 5.1(3) . . . 1_554 ? C22 C25 O4 Co1 -174.4(2) . . . 1_554 ? C20 C19 N5 C18 8.3(4) . . . . ? C24 C19 N5 C18 -172.8(3) . . . . ? C15 C18 N5 C19 67.5(3) . . . . ? 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 N5 H5N O4 0.78(3) 2.35(3) 3.099(3) 160(3) 3 O1W H1WB O3 0.851(18) 2.15(3) 2.886(3) 144(4) 2 O1W H1WA O1 0.861(18) 2.17(2) 2.984(3) 158(4) . _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.478 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.039 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 806753' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Cd N3 O7' _chemical_formula_weight 530.82 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 p21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8208(12) _cell_length_b 9.8968(7) _cell_length_c 17.2355(15) _cell_angle_alpha 90.00 _cell_angle_beta 105.965(10) _cell_angle_gamma 90.00 _cell_volume 2102.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.83 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9814 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 29.28 _reflns_number_total 4903 _reflns_number_gt 3733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water and amine were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A with U~iso~ = 1.5U~eq~(O) and N---H = 0.87+-0.02 \%A with U~iso~ = 1.5U~eq~(N). The distance of H3WA...H3WB was restrained to 1.30+-0.02 \%A. In order to give a reasonable H...H distance, the distance of H2WA...H3WB was restrained to 3.20+-0.02 \%A. ; _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^)+(0.0362P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4903 _refine_ls_number_parameters 306 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.246052(14) 0.115920(16) 0.729143(10) 0.03226(7) Uani 1 1 d . . . C1 C 0.18526(19) 0.3682(2) 0.62876(15) 0.0307(5) Uani 1 1 d . . . C2 C 0.16271(18) 0.4566(2) 0.55539(14) 0.0288(5) Uani 1 1 d . . . C3 C 0.11910(19) 0.5850(2) 0.55584(16) 0.0337(5) Uani 1 1 d . . . H3 H 0.1074 0.6190 0.6031 0.040 Uiso 1 1 calc R . . C4 C 0.0929(2) 0.6625(2) 0.48625(16) 0.0366(6) Uani 1 1 d . . . H4 H 0.0639 0.7483 0.4874 0.044 Uiso 1 1 calc R . . C5 C 0.10903(18) 0.6148(2) 0.41522(15) 0.0338(5) Uani 1 1 d . . . C6 C 0.1551(2) 0.4876(2) 0.41479(16) 0.0391(6) Uani 1 1 d . . . H6 H 0.1685 0.4549 0.3679 0.047 Uiso 1 1 calc R . . C7 C 0.1807(2) 0.4099(2) 0.48405(16) 0.0367(6) Uani 1 1 d . . . H7 H 0.2107 0.3246 0.4830 0.044 Uiso 1 1 calc R . . C8 C 0.0706(2) 0.6951(3) 0.33803(18) 0.0465(7) Uani 1 1 d . . . H8A H -0.0072 0.6830 0.3172 0.056 Uiso 1 1 calc R . . H8B H 0.0836 0.7901 0.3509 0.056 Uiso 1 1 calc R . . C9 C 0.2247(2) 0.6994(3) 0.27721(16) 0.0370(6) Uani 1 1 d . . . C10 C 0.2873(2) 0.7803(3) 0.33877(17) 0.0409(6) Uani 1 1 d . . . H10 H 0.2597 0.8080 0.3807 0.049 Uiso 1 1 calc R . . C11 C 0.3907(2) 0.8194(2) 0.33767(17) 0.0391(6) Uani 1 1 d . . . H11 H 0.4313 0.8737 0.3791 0.047 Uiso 1 1 calc R . . C12 C 0.4351(2) 0.7798(2) 0.27630(16) 0.0338(5) Uani 1 1 d . . . C13 C 0.3729(2) 0.6966(2) 0.21541(16) 0.0386(6) Uani 1 1 d . . . H13 H 0.4017 0.6667 0.1744 0.046 Uiso 1 1 calc R . . C14 C 0.2702(2) 0.6586(3) 0.21533(16) 0.0413(6) Uani 1 1 d . . . H14 H 0.2296 0.6048 0.1736 0.050 Uiso 1 1 calc R . . C15 C 0.5466(2) 0.8233(2) 0.27593(16) 0.0354(6) Uani 1 1 d . . . C16 C 0.0623(2) 0.0810(2) 0.81945(16) 0.0355(6) Uani 1 1 d . . . H16 H 0.0445 -0.0016 0.7935 0.043 Uiso 1 1 calc R . . C17 C 0.1392(2) 0.2698(2) 0.85856(17) 0.0382(6) Uani 1 1 d . . . H17 H 0.1858 0.3435 0.8646 0.046 Uiso 1 1 calc R . . C18 C 0.0611(2) 0.2549(2) 0.89649(17) 0.0428(6) Uani 1 1 d . . . H18 H 0.0438 0.3147 0.9327 0.051 Uiso 1 1 calc R . . C19 C -0.0774(2) 0.0713(3) 0.89577(18) 0.0470(7) Uani 1 1 d . . . H19A H -0.1275 0.0289 0.8496 0.056 Uiso 1 1 calc R A 1 H19B H -0.1166 0.1406 0.9161 0.056 Uiso 1 1 calc R A 1 C20' C -0.0341(6) -0.0343(9) 0.9615(5) 0.030(3) Uiso 0.336(11) 1 d P . 1 H20A H -0.0943 -0.0821 0.9729 0.036 Uiso 0.336(11) 1 calc PR . 1 H20B H 0.0100 -0.0996 0.9428 0.036 Uiso 0.336(11) 1 calc PR . 1 C20 C -0.0486(4) 0.0445(6) 0.9862(3) 0.0503(18) Uani 0.664(11) 1 d P . 2 H20C H -0.0345 0.1298 1.0149 0.060 Uiso 0.664(11) 1 calc PR . 2 H20D H -0.1098 0.0021 0.9993 0.060 Uiso 0.664(11) 1 calc PR . 2 N1 N 0.14026(16) 0.16124(19) 0.80987(12) 0.0332(4) Uani 1 1 d . . . N2 N 0.01230(16) 0.13327(19) 0.87089(12) 0.0353(5) Uani 1 1 d . . . O1 O 0.18670(16) 0.24137(15) 0.61611(11) 0.0449(5) Uani 1 1 d . . . O2 O 0.19890(14) 0.41640(15) 0.69763(11) 0.0369(4) Uani 1 1 d . . . O3 O 0.59001(14) 0.77099(16) 0.22503(11) 0.0383(4) Uani 1 1 d . . . O4 O 0.59488(16) 0.91160(18) 0.32485(13) 0.0490(5) Uani 1 1 d . . . O1W O 0.12036(19) -0.0386(2) 0.65089(13) 0.0549(5) Uani 1 1 d D . . H1WA H 0.109(3) -0.109(2) 0.673(2) 0.082 Uiso 1 1 d D . . H1WB H 0.097(3) -0.027(4) 0.6036(12) 0.082 Uiso 1 1 d D . . O2W O 0.1241(4) 0.0520(3) 0.4866(2) 0.1453(17) Uani 1 1 d D . . H2WA H 0.130(5) 0.121(5) 0.517(4) 0.218 Uiso 1 1 d D . . H2WB H 0.182(4) 0.007(8) 0.490(5) 0.218 Uiso 1 1 d D . . O3W O 0.3726(5) 0.0624(4) 0.5045(2) 0.1375(15) Uani 1 1 d D . . H3WB H 0.372(5) 0.145(2) 0.500(4) 0.206 Uiso 1 1 d D . . H3WA H 0.385(6) 0.055(7) 0.5554(14) 0.206 Uiso 1 1 d D . . N3 N 0.12037(19) 0.6612(3) 0.27496(15) 0.0479(6) Uani 1 1 d D . . H3N H 0.084(2) 0.615(3) 0.2348(15) 0.058 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03627(11) 0.03094(10) 0.03299(11) 0.00363(7) 0.01525(7) -0.00126(8) C1 0.0292(12) 0.0301(11) 0.0352(13) 0.0045(10) 0.0125(10) -0.0031(10) C2 0.0255(11) 0.0277(11) 0.0343(13) 0.0020(9) 0.0101(10) -0.0047(10) C3 0.0344(13) 0.0316(11) 0.0349(14) -0.0025(10) 0.0091(11) -0.0019(10) C4 0.0345(13) 0.0279(11) 0.0454(15) 0.0034(11) 0.0076(11) 0.0034(11) C5 0.0229(11) 0.0399(12) 0.0389(13) 0.0116(11) 0.0091(10) -0.0038(11) C6 0.0414(14) 0.0449(14) 0.0358(14) 0.0056(11) 0.0187(12) 0.0016(12) C7 0.0430(14) 0.0307(12) 0.0409(14) 0.0059(10) 0.0189(12) 0.0051(11) C8 0.0309(14) 0.0561(16) 0.0565(18) 0.0254(14) 0.0185(13) 0.0079(12) C9 0.0343(13) 0.0407(13) 0.0366(14) 0.0186(11) 0.0106(11) 0.0023(11) C10 0.0397(15) 0.0436(13) 0.0458(16) 0.0024(12) 0.0223(13) 0.0016(12) C11 0.0415(15) 0.0347(12) 0.0449(16) -0.0042(11) 0.0184(12) -0.0038(11) C12 0.0368(13) 0.0277(11) 0.0422(15) 0.0046(10) 0.0198(12) 0.0020(10) C13 0.0451(15) 0.0383(13) 0.0365(14) 0.0031(11) 0.0182(12) 0.0023(12) C14 0.0444(15) 0.0428(13) 0.0347(14) 0.0054(11) 0.0078(12) -0.0030(12) C15 0.0392(14) 0.0259(11) 0.0460(15) 0.0069(11) 0.0199(12) 0.0026(11) C16 0.0392(14) 0.0315(11) 0.0381(14) 0.0017(10) 0.0148(11) -0.0057(11) C17 0.0430(15) 0.0305(12) 0.0437(16) 0.0015(11) 0.0165(12) -0.0049(11) C18 0.0527(17) 0.0370(13) 0.0432(16) -0.0018(11) 0.0209(13) -0.0007(12) C19 0.0335(14) 0.0647(17) 0.0448(17) 0.0135(13) 0.0143(12) -0.0076(13) C20 0.045(3) 0.059(3) 0.058(3) 0.025(2) 0.032(2) 0.011(2) N1 0.0363(11) 0.0295(9) 0.0364(12) 0.0053(9) 0.0145(9) 0.0004(9) N2 0.0339(11) 0.0397(11) 0.0346(11) 0.0078(9) 0.0134(9) -0.0018(9) O1 0.0721(13) 0.0263(8) 0.0375(11) 0.0043(7) 0.0173(10) -0.0014(8) O2 0.0450(10) 0.0338(8) 0.0325(9) -0.0003(7) 0.0118(8) -0.0074(8) O3 0.0389(10) 0.0382(9) 0.0449(11) -0.0010(8) 0.0233(9) 0.0020(8) O4 0.0510(12) 0.0420(10) 0.0621(14) -0.0149(9) 0.0294(10) -0.0165(9) O1W 0.0725(15) 0.0418(10) 0.0440(12) 0.0091(10) 0.0054(11) -0.0125(10) O2W 0.269(5) 0.070(2) 0.084(3) -0.0100(18) 0.028(3) -0.027(3) O3W 0.250(5) 0.100(2) 0.064(2) -0.0015(17) 0.045(3) -0.002(3) N3 0.0376(13) 0.0673(15) 0.0358(13) 0.0141(11) 0.0049(10) -0.0075(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 N1 2.239(2) . ? Cd1 O1 2.2583(17) . ? Cd1 O3 2.3197(17) 3_666 ? Cd1 O2 2.3452(16) 2_546 ? Cd1 O1W 2.358(2) . ? Cd1 O4 2.4786(19) 3_666 ? Cd1 C15 2.750(2) 3_666 ? C1 O2 1.246(3) . ? C1 O1 1.275(3) . ? C1 C2 1.499(3) . ? C2 C3 1.389(3) . ? C2 C7 1.391(3) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 C8 1.511(3) . ? C6 C7 1.381(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N3 1.443(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N3 1.381(3) . ? C9 C10 1.393(4) . ? C9 C14 1.408(4) . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 H11 0.9300 . ? C12 C13 1.398(4) . ? C12 C15 1.495(3) . ? C13 C14 1.370(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O4 1.253(3) . ? C15 O3 1.271(3) . ? C15 Cd1 2.750(2) 3_666 ? C16 N1 1.322(3) . ? C16 N2 1.333(3) . ? C16 H16 0.9300 . ? C17 C18 1.346(4) . ? C17 N1 1.365(3) . ? C17 H17 0.9300 . ? C18 N2 1.372(3) . ? C18 H18 0.9300 . ? C19 N2 1.468(3) . ? C19 C20 1.523(5) . ? C19 C20' 1.529(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20' C20' 1.534(16) 3_557 ? C20' H20A 0.9700 . ? C20' H20B 0.9700 . ? C20 C20 1.492(10) 3_557 ? C20 H20C 0.9700 . ? C20 H20D 0.9700 . ? O2 Cd1 2.3452(16) 2_556 ? O3 Cd1 2.3197(17) 3_666 ? O4 Cd1 2.4786(19) 3_666 ? O1W H1WA 0.827(18) . ? O1W H1WB 0.796(18) . ? O2W H2WA 0.85(6) . ? O2W H2WB 0.85(6) . ? O3W H3WB 0.821(19) . ? O3W H3WA 0.85(2) . ? N3 H3N 0.853(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O1 107.93(7) . . ? N1 Cd1 O3 109.80(7) . 3_666 ? O1 Cd1 O3 95.00(7) . 3_666 ? N1 Cd1 O2 88.76(6) . 2_546 ? O1 Cd1 O2 155.13(6) . 2_546 ? O3 Cd1 O2 96.47(6) 3_666 2_546 ? N1 Cd1 O1W 92.86(8) . . ? O1 Cd1 O1W 81.25(7) . . ? O3 Cd1 O1W 156.99(7) 3_666 . ? O2 Cd1 O1W 79.57(7) 2_546 . ? N1 Cd1 O4 163.10(7) . 3_666 ? O1 Cd1 O4 81.57(7) . 3_666 ? O3 Cd1 O4 54.47(6) 3_666 3_666 ? O2 Cd1 O4 87.28(6) 2_546 3_666 ? O1W Cd1 O4 102.56(7) . 3_666 ? N1 Cd1 C15 137.04(8) . 3_666 ? O1 Cd1 C15 87.22(7) . 3_666 ? O3 Cd1 C15 27.39(7) 3_666 3_666 ? O2 Cd1 C15 92.91(7) 2_546 3_666 ? O1W Cd1 C15 129.66(8) . 3_666 ? O4 Cd1 C15 27.10(7) 3_666 3_666 ? O2 C1 O1 122.4(2) . . ? O2 C1 C2 121.59(19) . . ? O1 C1 C2 116.0(2) . . ? C3 C2 C7 118.3(2) . . ? C3 C2 C1 120.9(2) . . ? C7 C2 C1 120.8(2) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 118.8(2) . . ? C4 C5 C8 120.6(2) . . ? C6 C5 C8 120.5(2) . . ? C7 C6 C5 120.0(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 121.4(2) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? N3 C8 C5 115.8(2) . . ? N3 C8 H8A 108.3 . . ? C5 C8 H8A 108.3 . . ? N3 C8 H8B 108.3 . . ? C5 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? N3 C9 C10 122.0(2) . . ? N3 C9 C14 120.0(3) . . ? C10 C9 C14 118.0(2) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C13 118.0(2) . . ? C11 C12 C15 121.0(2) . . ? C13 C12 C15 121.0(2) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 121.3(3) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? O4 C15 O3 121.3(2) . . ? O4 C15 C12 119.6(2) . . ? O3 C15 C12 119.1(2) . . ? O4 C15 Cd1 64.30(13) . 3_666 ? O3 C15 Cd1 57.11(12) . 3_666 ? C12 C15 Cd1 175.61(17) . 3_666 ? N1 C16 N2 111.6(2) . . ? N1 C16 H16 124.2 . . ? N2 C16 H16 124.2 . . ? C18 C17 N1 110.3(2) . . ? C18 C17 H17 124.9 . . ? N1 C17 H17 124.9 . . ? C17 C18 N2 105.9(2) . . ? C17 C18 H18 127.0 . . ? N2 C18 H18 127.0 . . ? N2 C19 C20 112.5(3) . . ? N2 C19 C20' 110.3(3) . . ? C20 C19 C20' 35.6(3) . . ? N2 C19 H19A 109.6 . . ? C20 C19 H19A 133.2 . . ? C20' C19 H19A 109.6 . . ? N2 C19 H19B 109.6 . . ? C20 C19 H19B 76.0 . . ? C20' C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C20' C20' C19 110.0(8) 3_557 . ? C20' C20' H20A 109.7 3_557 . ? C19 C20' H20A 109.7 . . ? C20' C20' H20B 109.7 3_557 . ? C19 C20' H20B 109.7 . . ? H20A C20' H20B 108.2 . . ? C20 C20 C19 112.1(5) 3_557 . ? C20 C20 H20C 109.2 3_557 . ? C19 C20 H20C 109.2 . . ? C20 C20 H20D 109.2 3_557 . ? C19 C20 H20D 109.2 . . ? H20C C20 H20D 107.9 . . ? C16 N1 C17 105.1(2) . . ? C16 N1 Cd1 124.42(17) . . ? C17 N1 Cd1 130.51(16) . . ? C16 N2 C18 107.1(2) . . ? C16 N2 C19 126.3(2) . . ? C18 N2 C19 126.7(2) . . ? C1 O1 Cd1 114.27(15) . . ? C1 O2 Cd1 141.05(15) . 2_556 ? C15 O3 Cd1 95.50(15) . 3_666 ? C15 O4 Cd1 88.60(14) . 3_666 ? Cd1 O1W H1WA 118(3) . . ? Cd1 O1W H1WB 120(3) . . ? H1WA O1W H1WB 121(4) . . ? H2WA O2W H2WB 116(7) . . ? H3WB O3W H3WA 100(7) . . ? C9 N3 C8 122.7(2) . . ? C9 N3 H3N 119(2) . . ? C8 N3 H3N 119(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -22.8(3) . . . . ? O1 C1 C2 C3 155.4(2) . . . . ? O2 C1 C2 C7 159.9(2) . . . . ? O1 C1 C2 C7 -21.9(3) . . . . ? C7 C2 C3 C4 1.1(3) . . . . ? C1 C2 C3 C4 -176.3(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C3 C4 C5 C8 174.3(2) . . . . ? C4 C5 C6 C7 1.9(4) . . . . ? C8 C5 C6 C7 -174.1(2) . . . . ? C5 C6 C7 C2 -0.7(4) . . . . ? C3 C2 C7 C6 -0.8(4) . . . . ? C1 C2 C7 C6 176.6(2) . . . . ? C4 C5 C8 N3 160.7(2) . . . . ? C6 C5 C8 N3 -23.4(4) . . . . ? N3 C9 C10 C11 -178.3(2) . . . . ? C14 C9 C10 C11 0.6(4) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C10 C11 C12 C15 179.8(2) . . . . ? C11 C12 C13 C14 1.7(4) . . . . ? C15 C12 C13 C14 -179.0(2) . . . . ? C12 C13 C14 C9 -1.4(4) . . . . ? N3 C9 C14 C13 179.1(2) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? C11 C12 C15 O4 -10.1(4) . . . . ? C13 C12 C15 O4 170.6(2) . . . . ? C11 C12 C15 O3 170.8(2) . . . . ? C13 C12 C15 O3 -8.4(4) . . . . ? C11 C12 C15 Cd1 142(2) . . . 3_666 ? C13 C12 C15 Cd1 -37(3) . . . 3_666 ? N1 C17 C18 N2 0.2(3) . . . . ? N2 C19 C20' C20' 66.1(9) . . . 3_557 ? C20 C19 C20' C20' -34.5(6) . . . 3_557 ? N2 C19 C20 C20 -57.8(6) . . . 3_557 ? C20' C19 C20 C20 36.1(6) . . . 3_557 ? N2 C16 N1 C17 0.3(3) . . . . ? N2 C16 N1 Cd1 -179.87(15) . . . . ? C18 C17 N1 C16 -0.3(3) . . . . ? C18 C17 N1 Cd1 179.89(18) . . . . ? O1 Cd1 N1 C16 103.0(2) . . . . ? O3 Cd1 N1 C16 -154.62(19) 3_666 . . . ? O2 Cd1 N1 C16 -58.2(2) 2_546 . . . ? O1W Cd1 N1 C16 21.3(2) . . . . ? O4 Cd1 N1 C16 -134.6(2) 3_666 . . . ? C15 Cd1 N1 C16 -151.13(18) 3_666 . . . ? O1 Cd1 N1 C17 -77.2(2) . . . . ? O3 Cd1 N1 C17 25.2(2) 3_666 . . . ? O2 Cd1 N1 C17 121.6(2) 2_546 . . . ? O1W Cd1 N1 C17 -158.9(2) . . . . ? O4 Cd1 N1 C17 45.1(4) 3_666 . . . ? C15 Cd1 N1 C17 28.6(3) 3_666 . . . ? N1 C16 N2 C18 -0.2(3) . . . . ? N1 C16 N2 C19 -179.7(2) . . . . ? C17 C18 N2 C16 0.0(3) . . . . ? C17 C18 N2 C19 179.5(2) . . . . ? C20 C19 N2 C16 119.0(4) . . . . ? C20' C19 N2 C16 80.7(5) . . . . ? C20 C19 N2 C18 -60.5(4) . . . . ? C20' C19 N2 C18 -98.7(5) . . . . ? O2 C1 O1 Cd1 -10.7(3) . . . . ? C2 C1 O1 Cd1 171.08(15) . . . . ? N1 Cd1 O1 C1 57.21(18) . . . . ? O3 Cd1 O1 C1 -55.48(17) 3_666 . . . ? O2 Cd1 O1 C1 -172.71(16) 2_546 . . . ? O1W Cd1 O1 C1 147.39(18) . . . . ? O4 Cd1 O1 C1 -108.41(17) 3_666 . . . ? C15 Cd1 O1 C1 -81.77(18) 3_666 . . . ? O1 C1 O2 Cd1 156.87(18) . . . 2_556 ? C2 C1 O2 Cd1 -25.0(4) . . . 2_556 ? O4 C15 O3 Cd1 3.5(3) . . . 3_666 ? C12 C15 O3 Cd1 -177.48(19) . . . 3_666 ? O3 C15 O4 Cd1 -3.3(2) . . . 3_666 ? C12 C15 O4 Cd1 177.7(2) . . . 3_666 ? C10 C9 N3 C8 -3.6(4) . . . . ? C14 C9 N3 C8 177.5(2) . . . . ? C5 C8 N3 C9 -75.1(3) . . . . ? 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 H1WA O3 0.827(18) 1.884(19) 2.711(2) 177(4) 4_566 O3W H3WA O4 0.85(2) 2.03(3) 2.867(4) 165(6) 3_666 O1W H1WB O2W 0.796(18) 2.28(3) 2.984(5) 148(4) . O2W H2WA O1 0.85(6) 2.05(3) 2.856(4) 159(7) . _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.385 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.070 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 806754' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N5 O6 Zn' _chemical_formula_sum 'C26 H25 N5 O6 Zn' _chemical_formula_weight 568.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 p21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.7551(7) _cell_length_b 12.4113(7) _cell_length_c 16.3819(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.267(5) _cell_angle_gamma 90.00 _cell_volume 2623.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; Higashi,T (1995) Program for absorption correction. Rigaku Corporation, Tokyo, Japan. ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12202 _diffrn_reflns_av_R_equivalents 0.1003 _diffrn_reflns_av_sigmaI/netI 0.2288 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4775 _reflns_number_gt 1888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0145P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4775 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1460 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0563 _refine_ls_goodness_of_fit_ref 0.822 _refine_ls_restrained_S_all 0.700 _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 0.39778(3) 0.04501(5) 0.10437(3) 0.03888(15) Uani 1 1 d . . . C1 C 0.2166(4) 0.0063(3) 0.1652(3) 0.0552(15) Uani 1 1 d . . . H1 H 0.1724 -0.0120 0.1096 0.066 Uiso 1 1 calc R . . C2 C 0.3452(3) 0.0614(5) 0.2687(3) 0.0842(19) Uani 1 1 d . . . H2 H 0.4100 0.0894 0.3007 0.101 Uiso 1 1 calc R . . C3 C 0.2730(4) 0.0330(6) 0.3019(3) 0.097(2) Uani 1 1 d . . . H3 H 0.2786 0.0372 0.3601 0.117 Uiso 1 1 calc R . . C4 C 0.0949(3) -0.0474(5) 0.2425(3) 0.0849(16) Uani 1 1 d . . . H4A H 0.1123 -0.1065 0.2839 0.102 Uiso 1 1 calc R . . H4B H 0.0527 -0.0763 0.1863 0.102 Uiso 1 1 calc R . . C5 C 0.0315(3) 0.0365(5) 0.2713(3) 0.0686(14) Uani 1 1 d . . . H5A H -0.0204 -0.0003 0.2888 0.082 Uiso 1 1 calc R . . H5B H 0.0770 0.0750 0.3216 0.082 Uiso 1 1 calc R . . C6 C -0.0199(4) 0.1138(4) 0.2027(3) 0.0690(15) Uani 1 1 d . . . H6A H -0.0561 0.0748 0.1495 0.083 Uiso 1 1 calc R . . H6B H 0.0322 0.1586 0.1921 0.083 Uiso 1 1 calc R . . C7 C -0.0970(3) 0.1861(4) 0.2248(3) 0.0631(15) Uani 1 1 d . . . H7A H -0.1340 0.2290 0.1740 0.076 Uiso 1 1 calc R . . H7B H -0.1474 0.1410 0.2378 0.076 Uiso 1 1 calc R . . C8 C -0.0055(3) 0.3528(4) 0.2948(3) 0.0456(12) Uani 1 1 d . . . H8 H -0.0012 0.3823 0.2439 0.055 Uiso 1 1 calc R . . C9 C 0.0094(3) 0.3292(4) 0.4275(3) 0.0417(12) Uani 1 1 d . . . H9 H 0.0266 0.3399 0.4870 0.050 Uiso 1 1 calc R . . C10 C -0.0412(3) 0.2423(4) 0.3833(3) 0.0471(13) Uani 1 1 d . . . H10 H -0.0652 0.1834 0.4058 0.057 Uiso 1 1 calc R . . C11 C 0.5551(3) 0.1699(4) 0.2035(3) 0.0379(12) Uani 1 1 d . . . C12 C 0.6243(3) 0.2674(4) 0.2323(3) 0.0329(11) Uani 1 1 d . . . C13 C 0.6671(3) 0.2859(4) 0.3219(2) 0.0352(11) Uani 1 1 d . . . H13 H 0.6536 0.2391 0.3610 0.042 Uiso 1 1 calc R . . C14 C 0.7308(3) 0.3764(4) 0.3518(2) 0.0322(11) Uani 1 1 d . . . C15 C 0.7522(2) 0.4441(4) 0.2939(2) 0.0321(10) Uani 1 1 d . . . H15 H 0.7973 0.5016 0.3148 0.039 Uiso 1 1 calc R . . C16 C 0.7075(3) 0.4283(3) 0.2042(2) 0.0302(11) Uani 1 1 d . . . C17 C 0.6431(2) 0.3383(3) 0.1745(2) 0.0322(11) Uani 1 1 d . . . H17 H 0.6126 0.3262 0.1150 0.039 Uiso 1 1 calc R . . C18 C 0.7767(3) 0.3948(4) 0.4482(3) 0.0389(12) Uani 1 1 d . . . C19 C 0.7004(3) 0.4875(4) 0.0563(2) 0.0501(14) Uani 1 1 d . . . H19A H 0.6962 0.5562 0.0270 0.060 Uiso 1 1 calc R . . H19B H 0.6335 0.4524 0.0320 0.060 Uiso 1 1 calc R . . C20 C 0.7811(3) 0.4189(4) 0.0390(2) 0.0423(13) Uani 1 1 d . . . C21 C 0.8813(3) 0.4526(4) 0.0606(2) 0.0533(12) Uani 1 1 d . . . H21 H 0.8988 0.5204 0.0856 0.064 Uiso 1 1 calc R . . C22 C 0.9577(3) 0.3911(5) 0.0472(3) 0.0558(14) Uani 1 1 d . . . H22 H 1.0253 0.4169 0.0634 0.067 Uiso 1 1 calc R . . C23 C 0.9325(4) 0.2897(5) 0.0089(3) 0.0511(14) Uani 1 1 d . . . C24 C 0.8328(4) 0.2559(5) -0.0137(3) 0.0724(17) Uani 1 1 d . . . H24 H 0.8146 0.1888 -0.0398 0.087 Uiso 1 1 calc R . . C25 C 0.7587(4) 0.3181(5) 0.0009(3) 0.0630(15) Uani 1 1 d . . . H25 H 0.6913 0.2921 -0.0152 0.076 Uiso 1 1 calc R . . C26 C 1.0139(5) 0.2227(6) -0.0049(3) 0.0698(17) Uani 1 1 d . . . N1 N 0.3108(2) 0.0437(3) 0.18164(18) 0.0453(9) Uani 1 1 d . . . N2 N 0.1910(3) -0.0028(3) 0.2358(3) 0.0574(12) Uani 1 1 d . . . N3 N -0.0497(2) 0.2587(3) 0.2987(2) 0.0417(10) Uani 1 1 d . . . N4 N 0.0318(2) 0.3994(3) 0.3719(2) 0.0381(9) Uani 1 1 d . . . O1 O 0.49200(18) 0.1705(2) 0.12494(17) 0.0464(8) Uani 1 1 d . . . O2 O 0.56189(18) 0.0963(3) 0.25654(18) 0.0479(8) Uani 1 1 d . . . O3 O 0.7596(2) 0.3305(3) 0.49956(18) 0.0662(11) Uani 1 1 d . . . O4 O 0.83514(19) 0.4738(3) 0.47435(15) 0.0473(8) Uani 1 1 d . . . O5 O 0.9985(3) 0.1331(4) -0.0350(3) 0.1089(15) Uani 1 1 d . . . O6 O 1.1052(3) 0.2708(3) 0.0180(2) 0.0901(12) Uani 1 1 d . . . H6 H 1.1474 0.2302 0.0089 0.135 Uiso 1 1 calc R . . N5 N 0.7220(2) 0.5069(3) 0.1486(2) 0.0460(11) Uani 1 1 d . . . H5N H 0.783(3) 0.530(3) 0.171(2) 0.055 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0470(3) 0.0397(3) 0.0280(2) -0.0016(3) 0.01052(19) -0.0023(3) C1 0.062(3) 0.052(4) 0.051(3) -0.014(2) 0.019(3) 0.011(2) C2 0.053(3) 0.170(6) 0.033(3) -0.024(4) 0.018(2) -0.024(4) C3 0.062(3) 0.192(7) 0.043(3) 0.000(4) 0.025(3) -0.004(4) C4 0.078(3) 0.083(5) 0.116(4) -0.003(4) 0.062(3) -0.001(4) C5 0.065(3) 0.069(4) 0.086(4) -0.006(4) 0.045(3) -0.001(3) C6 0.094(4) 0.042(4) 0.066(3) -0.005(3) 0.022(3) -0.007(3) C7 0.059(3) 0.063(4) 0.056(3) -0.013(3) 0.005(3) -0.010(3) C8 0.062(3) 0.036(4) 0.036(3) -0.007(3) 0.015(2) -0.007(3) C9 0.052(3) 0.044(4) 0.033(3) 0.014(3) 0.020(2) 0.010(3) C10 0.049(3) 0.044(4) 0.052(3) 0.014(3) 0.022(2) 0.004(2) C11 0.040(3) 0.036(4) 0.041(3) -0.011(3) 0.018(2) 0.001(2) C12 0.025(2) 0.040(3) 0.032(3) 0.001(2) 0.0083(19) 0.004(2) C13 0.040(2) 0.035(3) 0.031(3) -0.001(2) 0.0120(19) 0.004(2) C14 0.033(2) 0.037(3) 0.027(2) 0.000(2) 0.0103(19) 0.002(2) C15 0.031(2) 0.037(3) 0.027(2) -0.004(2) 0.0075(17) -0.004(2) C16 0.031(2) 0.031(3) 0.030(2) 0.009(2) 0.0125(18) 0.002(2) C17 0.030(2) 0.039(3) 0.027(2) 0.001(2) 0.0087(19) 0.004(2) C18 0.035(2) 0.043(4) 0.033(3) -0.003(3) 0.004(2) -0.003(2) C19 0.055(3) 0.054(4) 0.041(3) 0.008(2) 0.018(2) 0.001(2) C20 0.049(3) 0.047(4) 0.031(2) -0.003(2) 0.013(2) -0.010(2) C21 0.058(3) 0.052(4) 0.057(3) -0.011(3) 0.029(2) -0.013(3) C22 0.057(3) 0.064(5) 0.052(3) -0.008(3) 0.026(3) -0.002(3) C23 0.067(4) 0.053(4) 0.038(3) -0.013(3) 0.025(3) 0.000(3) C24 0.071(4) 0.067(5) 0.078(4) -0.025(3) 0.025(3) -0.019(3) C25 0.057(3) 0.073(5) 0.057(3) -0.017(3) 0.019(3) -0.018(3) C26 0.083(4) 0.070(6) 0.058(4) -0.009(3) 0.027(3) -0.007(4) N1 0.0393(19) 0.058(3) 0.037(2) -0.006(2) 0.0104(16) 0.001(2) N2 0.052(2) 0.066(4) 0.062(3) -0.006(2) 0.031(2) -0.0011(19) N3 0.042(2) 0.038(3) 0.043(3) -0.006(2) 0.0107(19) -0.007(2) N4 0.050(2) 0.031(3) 0.029(2) -0.002(2) 0.0071(17) -0.0036(17) O1 0.0504(17) 0.045(2) 0.0321(18) 0.0009(15) 0.0002(14) -0.0099(15) O2 0.0546(18) 0.041(2) 0.0449(19) 0.0016(16) 0.0131(15) -0.0073(15) O3 0.076(2) 0.088(3) 0.0261(17) 0.0046(19) 0.0078(16) -0.037(2) O4 0.0562(17) 0.047(3) 0.0263(15) -0.0016(15) -0.0015(13) -0.0023(16) O5 0.125(3) 0.073(4) 0.143(4) -0.047(3) 0.064(3) 0.000(3) O6 0.084(2) 0.083(4) 0.113(3) -0.019(2) 0.047(2) 0.019(2) N5 0.049(2) 0.055(3) 0.037(2) 0.001(2) 0.0178(18) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.979(3) . ? Zn1 O4 2.016(2) 4_565 ? Zn1 N1 2.021(3) . ? Zn1 N4 2.024(3) 2_545 ? C1 N1 1.313(5) . ? C1 N2 1.326(5) . ? C1 H1 0.9300 . ? C2 C3 1.334(5) . ? C2 N1 1.356(4) . ? C2 H2 0.9300 . ? C3 N2 1.340(5) . ? C3 H3 0.9300 . ? C4 N2 1.472(5) . ? C4 C5 1.534(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.461(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.525(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.468(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.321(5) . ? C8 N3 1.329(5) . ? C8 H8 0.9300 . ? C9 C10 1.351(5) . ? C9 N4 1.369(5) . ? C9 H9 0.9300 . ? C10 N3 1.365(5) . ? C10 H10 0.9300 . ? C11 O2 1.242(5) . ? C11 O1 1.279(4) . ? C11 C12 1.511(6) . ? C12 C17 1.380(5) . ? C12 C13 1.399(5) . ? C13 C14 1.404(5) . ? C13 H13 0.9300 . ? C14 C15 1.373(5) . ? C14 C18 1.502(5) . ? C15 C16 1.397(4) . ? C15 H15 0.9300 . ? C16 N5 1.395(4) . ? C16 C17 1.404(5) . ? C17 H17 0.9300 . ? C18 O3 1.239(5) . ? C18 O4 1.246(5) . ? C19 N5 1.456(4) . ? C19 C20 1.502(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.365(5) . ? C20 C25 1.384(6) . ? C21 C22 1.377(5) . ? C21 H21 0.9300 . ? C22 C23 1.396(6) . ? C22 H22 0.9300 . ? C23 C24 1.357(6) . ? C23 C26 1.474(7) . ? C24 C25 1.365(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 O5 1.204(7) . ? C26 O6 1.323(6) . ? N4 Zn1 2.024(3) 2 ? O4 Zn1 2.016(2) 4_666 ? O6 H6 0.8200 . ? N5 H5N 0.84(3) . ? 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 O4 106.62(11) . 4_565 ? O1 Zn1 N1 113.24(14) . . ? O4 Zn1 N1 122.13(11) 4_565 . ? O1 Zn1 N4 115.37(11) . 2_545 ? O4 Zn1 N4 95.76(13) 4_565 2_545 ? N1 Zn1 N4 102.75(15) . 2_545 ? N1 C1 N2 113.0(4) . . ? N1 C1 H1 123.5 . . ? N2 C1 H1 123.5 . . ? C3 C2 N1 110.4(4) . . ? C3 C2 H2 124.8 . . ? N1 C2 H2 124.8 . . ? C2 C3 N2 107.1(4) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 C5 112.9(5) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 112.6(4) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 113.3(4) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N3 C7 C6 114.2(3) . . ? N3 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N3 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N4 C8 N3 111.8(4) . . ? N4 C8 H8 124.1 . . ? N3 C8 H8 124.1 . . ? C10 C9 N4 110.1(4) . . ? C10 C9 H9 124.9 . . ? N4 C9 H9 124.9 . . ? C9 C10 N3 105.8(4) . . ? C9 C10 H10 127.1 . . ? N3 C10 H10 127.1 . . ? O2 C11 O1 124.6(4) . . ? O2 C11 C12 119.0(4) . . ? O1 C11 C12 116.4(4) . . ? C17 C12 C13 120.3(4) . . ? C17 C12 C11 122.9(4) . . ? C13 C12 C11 116.7(4) . . ? C12 C13 C14 118.8(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 120.4(4) . . ? C15 C14 C18 121.4(4) . . ? C13 C14 C18 118.1(4) . . ? C14 C15 C16 121.3(4) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? N5 C16 C15 118.5(4) . . ? N5 C16 C17 123.1(3) . . ? C15 C16 C17 118.2(4) . . ? C12 C17 C16 120.9(4) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? O3 C18 O4 121.7(4) . . ? O3 C18 C14 120.5(4) . . ? O4 C18 C14 117.8(4) . . ? N5 C19 C20 113.0(3) . . ? N5 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? N5 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C25 116.2(4) . . ? C21 C20 C19 121.6(4) . . ? C25 C20 C19 122.3(4) . . ? C20 C21 C22 123.2(5) . . ? C20 C21 H21 118.4 . . ? C22 C21 H21 118.4 . . ? C21 C22 C23 119.2(4) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C24 C23 C22 118.1(5) . . ? C24 C23 C26 122.2(5) . . ? C22 C23 C26 119.6(5) . . ? C23 C24 C25 121.5(5) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C24 C25 C20 121.8(4) . . ? C24 C25 H25 119.1 . . ? C20 C25 H25 119.1 . . ? O5 C26 O6 123.2(6) . . ? O5 C26 C23 123.3(6) . . ? O6 C26 C23 113.5(6) . . ? C1 N1 C2 103.5(4) . . ? C1 N1 Zn1 129.0(3) . . ? C2 N1 Zn1 126.2(3) . . ? C1 N2 C3 105.9(4) . . ? C1 N2 C4 127.8(4) . . ? C3 N2 C4 126.2(4) . . ? C8 N3 C10 107.5(4) . . ? C8 N3 C7 125.4(4) . . ? C10 N3 C7 127.1(4) . . ? C8 N4 C9 104.8(4) . . ? C8 N4 Zn1 125.2(3) . 2 ? C9 N4 Zn1 130.0(3) . 2 ? C11 O1 Zn1 110.1(3) . . ? C18 O4 Zn1 105.1(3) . 4_666 ? C26 O6 H6 109.5 . . ? C16 N5 C19 122.5(3) . . ? C16 N5 H5N 107(3) . . ? C19 N5 H5N 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.3(7) . . . . ? N2 C4 C5 C6 73.2(5) . . . . ? C4 C5 C6 C7 170.5(4) . . . . ? C5 C6 C7 N3 65.2(6) . . . . ? N4 C9 C10 N3 0.4(5) . . . . ? O2 C11 C12 C17 162.0(4) . . . . ? O1 C11 C12 C17 -18.6(5) . . . . ? O2 C11 C12 C13 -20.2(5) . . . . ? O1 C11 C12 C13 159.2(3) . . . . ? C17 C12 C13 C14 -1.2(6) . . . . ? C11 C12 C13 C14 -179.1(3) . . . . ? C12 C13 C14 C15 -1.3(5) . . . . ? C12 C13 C14 C18 -179.6(3) . . . . ? C13 C14 C15 C16 3.3(6) . . . . ? C18 C14 C15 C16 -178.5(3) . . . . ? C14 C15 C16 N5 172.2(3) . . . . ? C14 C15 C16 C17 -2.6(6) . . . . ? C13 C12 C17 C16 1.8(6) . . . . ? C11 C12 C17 C16 179.6(3) . . . . ? N5 C16 C17 C12 -174.5(4) . . . . ? C15 C16 C17 C12 0.1(5) . . . . ? C15 C14 C18 O3 -177.3(4) . . . . ? C13 C14 C18 O3 1.0(6) . . . . ? C15 C14 C18 O4 0.0(6) . . . . ? C13 C14 C18 O4 178.3(4) . . . . ? N5 C19 C20 C21 -63.6(5) . . . . ? N5 C19 C20 C25 116.1(4) . . . . ? C25 C20 C21 C22 -0.9(6) . . . . ? C19 C20 C21 C22 178.8(4) . . . . ? C20 C21 C22 C23 0.7(6) . . . . ? C21 C22 C23 C24 0.1(7) . . . . ? C21 C22 C23 C26 -179.3(4) . . . . ? C22 C23 C24 C25 -0.6(7) . . . . ? C26 C23 C24 C25 178.8(5) . . . . ? C23 C24 C25 C20 0.3(8) . . . . ? C21 C20 C25 C24 0.4(7) . . . . ? C19 C20 C25 C24 -179.3(4) . . . . ? C24 C23 C26 O5 -1.8(8) . . . . ? C22 C23 C26 O5 177.6(6) . . . . ? C24 C23 C26 O6 177.5(5) . . . . ? C22 C23 C26 O6 -3.1(7) . . . . ? N2 C1 N1 C2 -1.4(5) . . . . ? N2 C1 N1 Zn1 166.4(3) . . . . ? C3 C2 N1 C1 1.1(6) . . . . ? C3 C2 N1 Zn1 -167.2(4) . . . . ? O1 Zn1 N1 C1 148.1(4) . . . . ? O4 Zn1 N1 C1 18.5(4) 4_565 . . . ? N4 Zn1 N1 C1 -86.7(4) 2_545 . . . ? O1 Zn1 N1 C2 -46.6(5) . . . . ? O4 Zn1 N1 C2 -176.2(4) 4_565 . . . ? N4 Zn1 N1 C2 78.5(5) 2_545 . . . ? N1 C1 N2 C3 1.3(5) . . . . ? N1 C1 N2 C4 -176.1(4) . . . . ? C2 C3 N2 C1 -0.5(6) . . . . ? C2 C3 N2 C4 176.9(5) . . . . ? C5 C4 N2 C1 -116.4(5) . . . . ? C5 C4 N2 C3 66.7(6) . . . . ? N4 C8 N3 C10 0.0(5) . . . . ? N4 C8 N3 C7 -179.0(3) . . . . ? C9 C10 N3 C8 -0.2(5) . . . . ? C9 C10 N3 C7 178.7(4) . . . . ? C6 C7 N3 C8 82.2(6) . . . . ? C6 C7 N3 C10 -96.5(5) . . . . ? N3 C8 N4 C9 0.2(5) . . . . ? N3 C8 N4 Zn1 -178.4(3) . . . 2 ? C10 C9 N4 C8 -0.4(4) . . . . ? C10 C9 N4 Zn1 178.2(3) . . . 2 ? O2 C11 O1 Zn1 5.9(5) . . . . ? C12 C11 O1 Zn1 -173.4(3) . . . . ? O4 Zn1 O1 C11 -162.3(2) 4_565 . . . ? N1 Zn1 O1 C11 60.6(3) . . . . ? N4 Zn1 O1 C11 -57.4(3) 2_545 . . . ? O3 C18 O4 Zn1 6.6(5) . . . 4_666 ? C14 C18 O4 Zn1 -170.7(3) . . . 4_666 ? C15 C16 N5 C19 165.2(3) . . . . ? C17 C16 N5 C19 -20.2(5) . . . . ? C20 C19 N5 C16 -75.0(5) . . . . ? 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 O6 H6 O3 0.82 1.77 2.573(4) 165.8 4_665 N5 H5N O2 0.84(3) 2.21(3) 3.046(4) 174(4) 2_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.420 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.053 #===END data_11 _database_code_depnum_ccdc_archive 'CCDC 806755' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H46 Cd2 N6 O17' _chemical_formula_weight 1131.64 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 c2/c _symmetry_space_group_name_Hall -C2yc 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 14.081(5) _cell_length_b 14.731(3) _cell_length_c 22.623(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.225(4) _cell_angle_gamma 90.00 _cell_volume 4603(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.704 _exptl_absorpt_correction_T_max 0.818 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11037 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 29.17 _reflns_number_total 5335 _reflns_number_gt 3562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water and amine were located in difference Fourier maps and refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A with U~iso~ = 1.5U~eq~(O) and N---H = 0.87+-0.02 \%A with U~iso~ = 1.5U~eq~(N). The distance of H1WA...H1WB was restrained to 1.44+-0.02 \%A. In order to give a reasonable O...O distances, the distances of O3W...O4W and O2W...O4W were restrained to 3.20+-0.02 and 3.00+-0.02 \%A, respectively. ; _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^)+(0.0487P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5335 _refine_ls_number_parameters 318 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.466176(17) 0.267223(17) 0.521242(12) 0.03014(10) Uani 1 1 d . . . C1 C 0.4323(3) 0.4283(3) 0.61148(19) 0.0397(9) Uani 1 1 d . . . H1 H 0.4765 0.4650 0.5971 0.048 Uiso 1 1 calc R . . C2 C 0.3415(3) 0.3173(3) 0.6240(2) 0.0565(12) Uani 1 1 d . . . H2 H 0.3111 0.2609 0.6201 0.068 Uiso 1 1 calc R . . C3 C 0.3246(3) 0.3837(3) 0.6611(2) 0.0623(13) Uani 1 1 d . . . H3 H 0.2808 0.3820 0.6870 0.075 Uiso 1 1 calc R . . C4 C 0.3880(4) 0.5413(3) 0.6846(2) 0.0613(13) Uani 1 1 d . . . H4A H 0.3228 0.5611 0.6861 0.074 Uiso 1 1 calc R . . H4B H 0.4164 0.5859 0.6617 0.074 Uiso 1 1 calc R . . C5 C 0.4474(4) 0.5375(3) 0.7487(2) 0.0622(13) Uani 1 1 d . . . H5A H 0.4308 0.5893 0.7711 0.075 Uiso 1 1 calc R . . H5B H 0.4301 0.4830 0.7683 0.075 Uiso 1 1 calc R . . C6 C 0.3665(2) 0.1033(2) 0.49288(18) 0.0313(8) Uani 1 1 d . . . C7 C 0.3304(2) 0.0100(2) 0.47385(16) 0.0273(8) Uani 1 1 d . . . C8 C 0.2464(2) -0.0235(2) 0.48912(15) 0.0262(8) Uani 1 1 d . . . H8 H 0.2115 0.0120 0.5114 0.031 Uiso 1 1 calc R . . C9 C 0.2146(2) -0.1099(2) 0.47119(15) 0.0264(7) Uani 1 1 d . . . C10 C 0.2673(2) -0.1638(2) 0.43855(16) 0.0276(7) Uani 1 1 d . . . H11 H 0.2448 -0.2214 0.4260 0.033 Uiso 1 1 calc R . . C11 C 0.3538(2) -0.1321(2) 0.42450(15) 0.0266(7) Uani 1 1 d . . . C12 C 0.3837(2) -0.0445(2) 0.44144(16) 0.0302(8) Uani 1 1 d . . . H12 H 0.4399 -0.0218 0.4311 0.036 Uiso 1 1 calc R . . C13 C 0.1239(2) -0.1473(2) 0.48759(17) 0.0304(8) Uani 1 1 d . . . C14 C 0.4653(3) -0.1514(3) 0.35222(19) 0.0450(10) Uani 1 1 d . . . H14A H 0.4958 -0.2004 0.3343 0.054 Uiso 1 1 calc R . . H14B H 0.5165 -0.1128 0.3737 0.054 Uiso 1 1 calc R . . C15 C 0.4046(3) -0.0960(3) 0.30176(19) 0.0460(10) Uani 1 1 d . . . C16 C 0.3370(4) -0.1368(3) 0.2580(2) 0.0601(13) Uani 1 1 d . . . H16 H 0.3277 -0.1992 0.2592 0.072 Uiso 1 1 calc R . . C17 C 0.2826(4) -0.0862(3) 0.2122(2) 0.0590(12) Uani 1 1 d . . . H17 H 0.2380 -0.1148 0.1822 0.071 Uiso 1 1 calc R . . C18 C 0.2944(3) 0.0072(3) 0.2109(2) 0.0528(11) Uani 1 1 d . . . C19 C 0.3609(4) 0.0484(3) 0.2539(2) 0.0574(12) Uani 1 1 d . . . H19 H 0.3694 0.1110 0.2529 0.069 Uiso 1 1 calc R . . C20 C 0.4163(3) -0.0029(3) 0.2995(2) 0.0556(12) Uani 1 1 d . . . H20 H 0.4619 0.0258 0.3289 0.067 Uiso 1 1 calc R . . C21 C 0.2329(4) 0.0639(3) 0.1630(2) 0.0592(12) Uani 1 1 d . . . N1 N 0.4103(2) 0.3452(2) 0.59274(15) 0.0381(7) Uani 1 1 d . . . N2 N 0.3833(2) 0.4535(2) 0.65361(15) 0.0440(8) Uani 1 1 d . . . O1 O 0.33114(19) 0.14621(18) 0.53053(14) 0.0469(7) Uani 1 1 d . . . O2 O 0.43573(18) 0.13417(16) 0.47127(13) 0.0440(7) Uani 1 1 d . . . O3 O 0.09254(18) -0.11273(19) 0.53089(13) 0.0461(7) Uani 1 1 d . . . O4 O 0.08130(18) -0.21225(17) 0.45898(13) 0.0443(7) Uani 1 1 d . . . O5 O 0.1793(3) 0.0171(2) 0.12021(16) 0.0734(10) Uani 1 1 d . . . H5 H 0.1480 0.0518 0.0955 0.110 Uiso 1 1 calc R . . O6 O 0.2307(3) 0.1459(3) 0.1644(2) 0.1035(15) Uani 1 1 d . . . O1W O 0.3543(2) 0.3380(2) 0.44704(16) 0.0555(8) Uani 1 1 d D . . H1WA H 0.367(3) 0.378(3) 0.423(2) 0.083 Uiso 1 1 d D . . H1WB H 0.300(2) 0.341(3) 0.457(2) 0.083 Uiso 1 1 d D . . O2W O 0.3815(5) 0.2376(5) 0.3494(3) 0.0693(19) Uani 0.50 1 d PD . . O3W O 0.5802(8) 0.1109(7) 0.3967(5) 0.132(4) Uiso 0.50 1 d PD . . O4W O 0.5639(11) 0.2490(10) 0.3043(8) 0.207(7) Uiso 0.50 1 d PD . . H2W H 0.436(5) 0.240(9) 0.340(7) 0.310 Uiso 1 1 d D . . N3 N 0.4118(2) -0.1910(2) 0.39681(14) 0.0325(7) Uani 1 1 d D . . H3N H 0.381(3) -0.232(2) 0.3807(18) 0.039 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02707(14) 0.02574(14) 0.03984(17) -0.00319(12) 0.01202(10) -0.00431(11) C1 0.035(2) 0.040(2) 0.044(3) -0.0041(18) 0.0066(18) 0.0000(17) C2 0.053(3) 0.061(3) 0.064(3) -0.015(2) 0.032(2) -0.015(2) C3 0.051(3) 0.075(3) 0.070(4) -0.017(3) 0.035(2) -0.005(3) C4 0.066(3) 0.061(3) 0.049(3) -0.021(2) -0.008(2) 0.022(2) C5 0.080(3) 0.061(3) 0.043(3) -0.010(2) 0.007(3) 0.004(2) C6 0.0233(17) 0.0232(18) 0.044(2) 0.0013(16) -0.0010(16) -0.0026(15) C7 0.0240(17) 0.0242(17) 0.032(2) 0.0017(14) 0.0025(15) -0.0037(14) C8 0.0238(16) 0.0249(18) 0.031(2) -0.0001(14) 0.0086(15) -0.0018(14) C9 0.0226(16) 0.0278(18) 0.029(2) 0.0020(14) 0.0054(14) -0.0054(14) C10 0.0285(18) 0.0213(16) 0.032(2) 0.0004(13) 0.0036(15) -0.0025(14) C11 0.0242(16) 0.0271(18) 0.028(2) 0.0023(14) 0.0048(14) 0.0018(14) C12 0.0248(17) 0.0289(19) 0.037(2) 0.0009(15) 0.0072(15) -0.0067(15) C13 0.0239(17) 0.0339(19) 0.034(2) 0.0062(16) 0.0061(15) -0.0047(16) C14 0.044(2) 0.051(2) 0.043(3) 0.0050(19) 0.0160(19) 0.0121(19) C15 0.046(2) 0.053(3) 0.044(3) 0.001(2) 0.018(2) 0.008(2) C16 0.078(3) 0.047(3) 0.053(3) -0.003(2) 0.007(3) 0.010(2) C17 0.079(3) 0.054(3) 0.040(3) 0.000(2) 0.001(2) 0.013(2) C18 0.063(3) 0.055(3) 0.044(3) 0.005(2) 0.019(2) 0.016(2) C19 0.063(3) 0.050(3) 0.062(3) 0.012(2) 0.018(3) 0.008(2) C20 0.055(3) 0.057(3) 0.057(3) 0.013(2) 0.015(2) -0.001(2) C21 0.075(3) 0.053(3) 0.050(3) 0.007(2) 0.016(3) 0.014(3) N1 0.0367(17) 0.0374(18) 0.042(2) -0.0058(14) 0.0125(15) -0.0011(14) N2 0.0450(19) 0.046(2) 0.038(2) -0.0115(15) 0.0022(15) 0.0147(17) O1 0.0475(16) 0.0345(15) 0.062(2) -0.0166(13) 0.0191(14) -0.0104(12) O2 0.0367(14) 0.0266(13) 0.072(2) -0.0049(13) 0.0179(14) -0.0129(12) O3 0.0379(15) 0.0580(18) 0.0478(18) -0.0150(14) 0.0219(13) -0.0192(13) O4 0.0346(13) 0.0386(16) 0.062(2) -0.0151(13) 0.0161(13) -0.0214(12) O5 0.097(3) 0.067(2) 0.053(2) 0.0119(18) 0.006(2) 0.026(2) O6 0.142(4) 0.059(2) 0.095(3) 0.019(2) -0.011(3) 0.019(2) O1W 0.0496(18) 0.0561(19) 0.062(2) 0.0149(15) 0.0145(16) 0.0115(15) O2W 0.079(5) 0.062(4) 0.063(5) -0.018(3) 0.005(4) 0.014(4) N3 0.0299(16) 0.0302(16) 0.039(2) -0.0060(14) 0.0104(13) -0.0032(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 N1 2.247(3) . ? Cd1 O2 2.261(2) . ? Cd1 O1W 2.314(3) . ? Cd1 O4 2.365(3) 3 ? Cd1 O3 2.488(3) 3 ? Cd1 N3 2.532(3) 5_656 ? Cd1 O1 2.644(3) . ? C1 N1 1.312(5) . ? C1 N2 1.334(5) . ? C1 H1 0.9300 . ? C2 C3 1.339(6) . ? C2 N1 1.370(5) . ? C2 H2 0.9300 . ? C3 N2 1.351(6) . ? C3 H3 0.9300 . ? C4 N2 1.466(5) . ? C4 C5 1.528(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.470(10) 2_656 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O1 1.240(4) . ? C6 O2 1.257(4) . ? C6 C7 1.500(5) . ? C7 C8 1.386(5) . ? C7 C12 1.400(5) . ? C8 C9 1.384(5) . ? C8 H8 0.9300 . ? C9 C10 1.393(5) . ? C9 C13 1.502(5) . ? C10 C11 1.397(5) . ? C10 H11 0.9300 . ? C11 C12 1.388(5) . ? C11 N3 1.418(4) . ? C12 H12 0.9300 . ? C13 O4 1.242(4) . ? C13 O3 1.258(4) . ? C14 N3 1.490(5) . ? C14 C15 1.523(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.371(6) . ? C15 C20 1.384(6) . ? C16 C17 1.381(6) . ? C16 H16 0.9300 . ? C17 C18 1.387(6) . ? C17 H17 0.9300 . ? C18 C19 1.356(7) . ? C18 C21 1.503(7) . ? C19 C20 1.389(7) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 O6 1.209(6) . ? C21 O5 1.303(6) . ? O3 Cd1 2.488(2) 3_445 ? O4 Cd1 2.365(3) 3_445 ? O5 H5 0.8200 . ? O1W H1WA 0.84(4) . ? O1W H1WB 0.842(19) . ? O2W H2W 0.84(2) . ? N3 Cd1 2.532(3) 5_656 ? N3 H3N 0.797(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 N1 Cd1 O2 138.07(10) . . ? N1 Cd1 O1W 90.44(12) . . ? O2 Cd1 O1W 89.52(11) . . ? N1 Cd1 O4 137.72(10) . 3 ? O2 Cd1 O4 84.16(9) . 3 ? O1W Cd1 O4 87.66(11) . 3 ? N1 Cd1 O3 85.30(10) . 3 ? O2 Cd1 O3 136.27(9) . 3 ? O1W Cd1 O3 96.76(11) . 3 ? O4 Cd1 O3 53.12(9) 3 3 ? N1 Cd1 N3 88.99(11) . 5_656 ? O2 Cd1 N3 90.99(10) . 5_656 ? O1W Cd1 N3 179.41(11) . 5_656 ? O4 Cd1 N3 92.68(10) 3 5_656 ? O3 Cd1 N3 83.06(10) 3 5_656 ? N1 Cd1 O1 85.96(10) . . ? O2 Cd1 O1 52.14(9) . . ? O1W Cd1 O1 87.86(10) . . ? O4 Cd1 O1 136.09(9) 3 . ? O3 Cd1 O1 170.14(9) 3 . ? N3 Cd1 O1 92.22(9) 5_656 . ? N1 C1 N2 111.7(3) . . ? N1 C1 H1 124.2 . . ? N2 C1 H1 124.2 . . ? C3 C2 N1 109.5(4) . . ? C3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? C2 C3 N2 106.9(4) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 C5 112.8(4) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C5 C5 C4 113.5(5) 2_656 . ? C5 C5 H5A 108.9 2_656 . ? C4 C5 H5A 108.9 . . ? C5 C5 H5B 108.9 2_656 . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 C6 O2 121.9(3) . . ? O1 C6 C7 120.4(3) . . ? O2 C6 C7 117.7(3) . . ? C8 C7 C12 119.8(3) . . ? C8 C7 C6 120.8(3) . . ? C12 C7 C6 119.3(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 C13 120.5(3) . . ? C10 C9 C13 119.3(3) . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H11 119.7 . . ? C11 C10 H11 119.7 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 N3 121.3(3) . . ? C10 C11 N3 119.9(3) . . ? C11 C12 C7 120.8(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? O4 C13 O3 120.7(3) . . ? O4 C13 C9 120.1(3) . . ? O3 C13 C9 119.2(3) . . ? N3 C14 C15 115.7(3) . . ? N3 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? N3 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C20 118.6(4) . . ? C16 C15 C14 121.1(4) . . ? C20 C15 C14 120.3(4) . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 120.0(4) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 119.9(4) . . ? C19 C18 C21 119.2(4) . . ? C17 C18 C21 120.8(4) . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 120.9(5) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? O6 C21 O5 122.3(5) . . ? O6 C21 C18 123.5(5) . . ? O5 C21 C18 114.2(4) . . ? C1 N1 C2 105.0(3) . . ? C1 N1 Cd1 128.0(3) . . ? C2 N1 Cd1 126.9(3) . . ? C1 N2 C3 106.9(3) . . ? C1 N2 C4 127.3(4) . . ? C3 N2 C4 125.7(4) . . ? C6 O1 Cd1 84.1(2) . . ? C6 O2 Cd1 101.8(2) . . ? C13 O3 Cd1 89.9(2) . 3_445 ? C13 O4 Cd1 96.1(2) . 3_445 ? C21 O5 H5 109.5 . . ? Cd1 O1W H1WA 126(3) . . ? Cd1 O1W H1WB 111(3) . . ? H1WA O1W H1WB 116(3) . . ? C11 N3 C14 118.0(3) . . ? C11 N3 Cd1 108.4(2) . 5_656 ? C14 N3 Cd1 108.0(2) . 5_656 ? C11 N3 H3N 111(3) . . ? C14 N3 H3N 107(3) . . ? Cd1 N3 H3N 103(3) 5_656 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.4(6) . . . . ? N2 C4 C5 C5 77.5(4) . . . 2_656 ? O1 C6 C7 C8 11.7(5) . . . . ? O2 C6 C7 C8 -171.1(3) . . . . ? O1 C6 C7 C12 -166.8(3) . . . . ? O2 C6 C7 C12 10.4(5) . . . . ? C12 C7 C8 C9 -1.3(5) . . . . ? C6 C7 C8 C9 -179.8(3) . . . . ? C7 C8 C9 C10 0.9(5) . . . . ? C7 C8 C9 C13 179.8(3) . . . . ? C8 C9 C10 C11 1.2(5) . . . . ? C13 C9 C10 C11 -177.7(3) . . . . ? C9 C10 C11 C12 -2.7(5) . . . . ? C9 C10 C11 N3 173.4(3) . . . . ? C10 C11 C12 C7 2.3(5) . . . . ? N3 C11 C12 C7 -173.9(3) . . . . ? C8 C7 C12 C11 -0.3(5) . . . . ? C6 C7 C12 C11 178.3(3) . . . . ? C8 C9 C13 O4 160.5(3) . . . . ? C10 C9 C13 O4 -20.6(5) . . . . ? C8 C9 C13 O3 -20.3(5) . . . . ? C10 C9 C13 O3 158.6(3) . . . . ? N3 C14 C15 C16 -68.9(5) . . . . ? N3 C14 C15 C20 110.6(4) . . . . ? C20 C15 C16 C17 0.8(7) . . . . ? C14 C15 C16 C17 -179.7(4) . . . . ? C15 C16 C17 C18 -1.5(7) . . . . ? C16 C17 C18 C19 1.4(7) . . . . ? C16 C17 C18 C21 -177.3(4) . . . . ? C17 C18 C19 C20 -0.6(7) . . . . ? C21 C18 C19 C20 178.1(4) . . . . ? C16 C15 C20 C19 0.0(6) . . . . ? C14 C15 C20 C19 -179.5(4) . . . . ? C18 C19 C20 C15 -0.1(7) . . . . ? C19 C18 C21 O6 -9.3(8) . . . . ? C17 C18 C21 O6 169.5(5) . . . . ? C19 C18 C21 O5 172.7(4) . . . . ? C17 C18 C21 O5 -8.5(7) . . . . ? N2 C1 N1 C2 1.5(5) . . . . ? N2 C1 N1 Cd1 178.4(2) . . . . ? C3 C2 N1 C1 -0.6(5) . . . . ? C3 C2 N1 Cd1 -177.5(3) . . . . ? O2 Cd1 N1 C1 -172.0(3) . . . . ? O1W Cd1 N1 C1 -82.3(3) . . . . ? O4 Cd1 N1 C1 4.7(4) 3 . . . ? O3 Cd1 N1 C1 14.5(3) 3 . . . ? N3 Cd1 N1 C1 97.6(3) 5_656 . . . ? O1 Cd1 N1 C1 -170.1(3) . . . . ? O2 Cd1 N1 C2 4.2(4) . . . . ? O1W Cd1 N1 C2 94.0(4) . . . . ? O4 Cd1 N1 C2 -179.0(3) 3 . . . ? O3 Cd1 N1 C2 -169.3(4) 3 . . . ? N3 Cd1 N1 C2 -86.2(4) 5_656 . . . ? O1 Cd1 N1 C2 6.1(4) . . . . ? N1 C1 N2 C3 -1.8(5) . . . . ? N1 C1 N2 C4 -179.4(4) . . . . ? C2 C3 N2 C1 1.3(5) . . . . ? C2 C3 N2 C4 179.0(4) . . . . ? C5 C4 N2 C1 -103.4(5) . . . . ? C5 C4 N2 C3 79.4(6) . . . . ? O2 C6 O1 Cd1 -1.6(3) . . . . ? C7 C6 O1 Cd1 175.4(3) . . . . ? N1 Cd1 O1 C6 -177.4(2) . . . . ? O2 Cd1 O1 C6 1.0(2) . . . . ? O1W Cd1 O1 C6 92.0(2) . . . . ? O4 Cd1 O1 C6 7.6(3) 3 . . . ? O3 Cd1 O1 C6 -149.7(5) 3 . . . ? N3 Cd1 O1 C6 -88.5(2) 5_656 . . . ? O1 C6 O2 Cd1 2.0(4) . . . . ? C7 C6 O2 Cd1 -175.2(2) . . . . ? N1 Cd1 O2 C6 1.5(3) . . . . ? O1W Cd1 O2 C6 -88.6(2) . . . . ? O4 Cd1 O2 C6 -176.3(2) 3 . . . ? O3 Cd1 O2 C6 172.0(2) 3 . . . ? N3 Cd1 O2 C6 91.1(2) 5_656 . . . ? O1 Cd1 O2 C6 -1.0(2) . . . . ? O4 C13 O3 Cd1 5.1(4) . . . 3_445 ? C9 C13 O3 Cd1 -174.1(3) . . . 3_445 ? O3 C13 O4 Cd1 -5.4(4) . . . 3_445 ? C9 C13 O4 Cd1 173.8(3) . . . 3_445 ? C12 C11 N3 C14 -38.7(5) . . . . ? C10 C11 N3 C14 145.2(3) . . . . ? C12 C11 N3 Cd1 84.3(3) . . . 5_656 ? C10 C11 N3 Cd1 -91.8(3) . . . 5_656 ? C15 C14 N3 C11 -52.2(5) . . . . ? C15 C14 N3 Cd1 -175.5(3) . . . 5_656 ? 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 H1WA O5 0.84(4) 2.30(3) 3.037(5) 145(4) 4 O1W H1WB O1 0.842(19) 1.93(2) 2.765(4) 173(5) 7_556 _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.938 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.093 #===END