# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Spyros P Perlepes' _publ_contact_author_email perlepes@patreas.upatras.gr loop_ _publ_author_name K.Konidaris C.Polyzou G.Kostakis A.Tasiopoulos O.Roubeau E.Manessi-Zoupa A.Powell S.Perlepes data_kk148c _database_code_depnum_ccdc_archive 'CCDC 846480' #TrackingRef '- Complex 1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N5 O9 Zn' _chemical_formula_weight 434.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.00202 0.00197 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.00306 0.00403 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.00415 0.00737 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Zn Zn 0.19405 1.67179 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6874(12) _cell_length_b 9.9484(16) _cell_length_c 11.4223(17) _cell_angle_alpha 96.499(3) _cell_angle_beta 96.478(4) _cell_angle_gamma 111.272(4) _cell_volume 797.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2239 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.89 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'ALS beamline 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5343 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.99 _reflns_number_total 3182 _reflns_number_gt 2768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. All non-hydrogens were refined anisotropically. Hydrogens were found in difference Fourier maps, including those on O1 and O3, and were placed geometrically on their riding atom. ; _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^)+(0.0585P)^2^+0.5361P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3182 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Zn1 Zn 0.54812(5) 0.18711(3) 0.82854(3) 0.02597(14) Uani 1 1 d . . . O1 O 0.5277(3) 0.5045(2) 0.7952(2) 0.0339(5) Uani 1 1 d . . . H1 H 0.4660 0.4552 0.7289 0.051 Uiso 1 1 calc R . . O2 O 0.5286(3) -0.0262(2) 0.8229(2) 0.0321(5) Uani 1 1 d . . . O3 O 0.6003(4) -0.2030(3) 0.7259(3) 0.0526(7) Uani 1 1 d . . . H3 H 0.6489 -0.2157 0.6654 0.079 Uiso 1 1 calc R . . O4 O 0.2993(4) 0.1770(3) 0.9508(2) 0.0449(6) Uani 1 1 d . . . O5 O 0.2657(3) 0.1330(3) 0.7602(2) 0.0475(7) Uani 1 1 d . . . N1 N 0.6008(3) 0.4206(3) 0.8574(2) 0.0258(5) Uani 1 1 d . . . N2 N 0.7348(3) 0.2648(3) 0.9868(2) 0.0255(5) Uani 1 1 d . . . N3 N 0.6649(3) 0.1611(2) 0.6786(2) 0.0231(5) Uani 1 1 d . . . N4 N 0.1934(4) 0.1476(3) 0.8522(3) 0.0361(7) Uani 1 1 d . . . N5 N 0.7203(4) -0.3962(3) 0.4723(2) 0.0270(5) Uani 1 1 d . . . C8 C 0.6710(4) 0.0275(3) 0.6520(3) 0.0236(6) Uani 1 1 d . . . C3 C 0.8767(4) 0.4670(3) 1.1455(3) 0.0306(7) Uani 1 1 d . . . H3A H 0.8996 0.5654 1.1775 0.037 Uiso 1 1 calc R . . C7 C 0.5949(4) -0.0710(3) 0.7391(3) 0.0270(6) Uani 1 1 d . . . C5 C 0.9141(5) 0.2416(4) 1.1607(3) 0.0351(7) Uani 1 1 d . . . H5A H 0.9654 0.1834 1.2023 0.042 Uiso 1 1 calc R . . C2 C 0.7733(4) 0.4054(3) 1.0340(3) 0.0257(6) Uani 1 1 d . . . C6 C 0.8057(4) 0.1857(3) 1.0494(3) 0.0317(7) Uani 1 1 d . . . H6A H 0.7802 0.0873 1.0158 0.038 Uiso 1 1 calc R . . C9 C 0.7417(4) -0.0098(3) 0.5531(3) 0.0286(7) Uani 1 1 d . . . H9A H 0.7423 -0.1052 0.5345 0.034 Uiso 1 1 calc R . . C1 C 0.6961(4) 0.4869(3) 0.9591(3) 0.0257(6) Uani 1 1 d . . . H1A H 0.7167 0.5863 0.9857 0.031 Uiso 1 1 calc R . . C4 C 0.9479(5) 0.3833(4) 1.2115(3) 0.0344(7) Uani 1 1 d . . . H4A H 1.0181 0.4228 1.2897 0.041 Uiso 1 1 calc R . . C11 C 0.8073(4) 0.2314(3) 0.5095(3) 0.0295(7) Uani 1 1 d . . . H11A H 0.8557 0.3044 0.4618 0.035 Uiso 1 1 calc R . . C12 C 0.7311(4) 0.2596(3) 0.6082(3) 0.0260(6) Uani 1 1 d . . . H12A H 0.7253 0.3533 0.6270 0.031 Uiso 1 1 calc R . . C10 C 0.8118(5) 0.0935(3) 0.4814(3) 0.0321(7) Uani 1 1 d . . . H10A H 0.8626 0.0703 0.4133 0.038 Uiso 1 1 calc R . . O8 O 0.6000(4) -0.3555(3) 0.4207(2) 0.0391(6) Uani 1 1 d . . . O6 O 0.0290(4) 0.1351(4) 0.8434(3) 0.0613(8) Uani 1 1 d . . . O9 O 0.7693(4) -0.4870(3) 0.4176(2) 0.0418(6) Uani 1 1 d . . . O7 O 0.7873(3) -0.3425(3) 0.5791(2) 0.0366(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0284(2) 0.02394(19) 0.0240(2) -0.00015(13) 0.00235(14) 0.01001(14) O1 0.0498(13) 0.0269(10) 0.0256(13) 0.0007(9) -0.0077(10) 0.0203(10) O2 0.0398(12) 0.0255(10) 0.0313(13) 0.0051(9) 0.0097(10) 0.0115(9) O3 0.0648(18) 0.0407(14) 0.0564(19) 0.0069(12) 0.0154(14) 0.0237(13) O4 0.0406(14) 0.0352(12) 0.0493(17) 0.0102(11) -0.0070(12) 0.0067(11) O5 0.0362(13) 0.0462(14) 0.0489(17) -0.0150(12) 0.0086(12) 0.0091(11) N1 0.0298(13) 0.0261(12) 0.0237(14) 0.0060(10) 0.0024(11) 0.0135(10) N2 0.0251(12) 0.0260(12) 0.0255(14) 0.0041(10) 0.0037(10) 0.0101(10) N3 0.0241(11) 0.0198(11) 0.0235(14) -0.0003(9) -0.0001(10) 0.0086(9) N4 0.0311(14) 0.0295(13) 0.0458(19) -0.0004(12) 0.0049(13) 0.0117(11) N5 0.0305(13) 0.0245(12) 0.0269(15) 0.0048(10) 0.0020(11) 0.0122(10) C8 0.0224(13) 0.0220(13) 0.0239(16) 0.0001(11) -0.0031(11) 0.0086(11) C3 0.0316(16) 0.0294(15) 0.0266(18) 0.0016(12) 0.0036(13) 0.0080(13) C7 0.0278(14) 0.0221(13) 0.0276(17) 0.0024(11) -0.0009(12) 0.0077(11) C5 0.0332(16) 0.0383(17) 0.036(2) 0.0166(14) 0.0017(14) 0.0139(14) C2 0.0259(14) 0.0276(14) 0.0239(16) 0.0028(12) 0.0051(12) 0.0105(11) C6 0.0305(15) 0.0288(15) 0.037(2) 0.0099(13) 0.0045(14) 0.0115(13) C9 0.0336(15) 0.0225(13) 0.0282(18) -0.0013(12) 0.0019(13) 0.0115(12) C1 0.0290(14) 0.0258(13) 0.0213(16) 0.0023(11) 0.0025(12) 0.0103(11) C4 0.0317(16) 0.0393(17) 0.0262(18) 0.0072(14) -0.0032(13) 0.0083(14) C11 0.0307(15) 0.0297(15) 0.0272(18) 0.0065(12) 0.0019(13) 0.0107(12) C12 0.0271(14) 0.0218(13) 0.0273(17) 0.0016(11) -0.0012(12) 0.0096(11) C10 0.0370(17) 0.0325(15) 0.0274(18) 0.0016(13) 0.0061(14) 0.0148(13) O8 0.0489(14) 0.0414(13) 0.0317(14) -0.0026(10) -0.0092(11) 0.0298(11) O6 0.0284(13) 0.091(2) 0.063(2) -0.0015(16) 0.0046(13) 0.0263(14) O9 0.0533(15) 0.0406(13) 0.0402(15) -0.0008(11) 0.0044(12) 0.0311(12) O7 0.0431(13) 0.0451(13) 0.0232(13) 0.0013(10) -0.0019(10) 0.0220(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.054(3) . ? Zn1 N3 2.055(2) . ? Zn1 O2 2.065(2) . ? Zn1 O5 2.071(3) . ? Zn1 N1 2.187(2) . ? Zn1 O4 2.473(3) . ? O1 N1 1.379(3) . ? O1 H1 0.8400 . ? O2 C7 1.246(4) . ? O3 C7 1.320(4) . ? O3 H3 0.8400 . ? O4 N4 1.250(4) . ? O5 N4 1.261(4) . ? N1 C1 1.267(4) . ? N2 C6 1.333(4) . ? N2 C2 1.352(4) . ? N3 C12 1.332(4) . ? N3 C8 1.348(3) . ? N4 O6 1.216(4) . ? N5 O9 1.233(3) . ? N5 O7 1.245(3) . ? N5 O8 1.253(3) . ? C8 C9 1.379(4) . ? C8 C7 1.493(4) . ? C3 C2 1.368(4) . ? C3 C4 1.393(5) . ? C3 H3A 0.9500 . ? C5 C6 1.373(5) . ? C5 C4 1.381(5) . ? C5 H5A 0.9500 . ? C2 C1 1.460(4) . ? C6 H6A 0.9500 . ? C9 C10 1.380(5) . ? C9 H9A 0.9500 . ? C1 H1A 0.9500 . ? C4 H4A 0.9500 . ? C11 C12 1.376(4) . ? C11 C10 1.386(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C10 H10A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N3 115.66(10) . . ? N2 Zn1 O2 94.65(9) . . ? N3 Zn1 O2 79.60(9) . . ? N2 Zn1 O5 141.04(10) . . ? N3 Zn1 O5 103.16(10) . . ? O2 Zn1 O5 95.41(10) . . ? N2 Zn1 N1 77.01(9) . . ? N3 Zn1 N1 103.06(9) . . ? O2 Zn1 N1 171.61(9) . . ? O5 Zn1 N1 91.73(10) . . ? N2 Zn1 O4 86.02(9) . . ? N3 Zn1 O4 158.27(9) . . ? O2 Zn1 O4 98.16(9) . . ? O5 Zn1 O4 55.31(9) . . ? N1 Zn1 O4 82.31(9) . . ? N1 O1 H1 109.5 . . ? C7 O2 Zn1 114.2(2) . . ? C7 O3 H3 109.5 . . ? N4 O4 Zn1 84.42(19) . . ? N4 O5 Zn1 103.3(2) . . ? C1 N1 O1 113.6(2) . . ? C1 N1 Zn1 113.1(2) . . ? O1 N1 Zn1 132.47(18) . . ? C6 N2 C2 118.8(3) . . ? C6 N2 Zn1 125.6(2) . . ? C2 N2 Zn1 115.3(2) . . ? C12 N3 C8 119.1(2) . . ? C12 N3 Zn1 127.20(18) . . ? C8 N3 Zn1 113.7(2) . . ? O6 N4 O4 122.6(3) . . ? O6 N4 O5 120.6(3) . . ? O4 N4 O5 116.8(3) . . ? O9 N5 O7 121.8(3) . . ? O9 N5 O8 120.1(3) . . ? O7 N5 O8 118.1(2) . . ? N3 C8 C9 121.5(3) . . ? N3 C8 C7 113.4(2) . . ? C9 C8 C7 125.1(3) . . ? C2 C3 C4 119.0(3) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? O2 C7 O3 121.7(3) . . ? O2 C7 C8 119.0(3) . . ? O3 C7 C8 119.3(3) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? N2 C2 C3 122.0(3) . . ? N2 C2 C1 115.9(3) . . ? C3 C2 C1 122.1(3) . . ? N2 C6 C5 122.2(3) . . ? N2 C6 H6A 118.9 . . ? C5 C6 H6A 118.9 . . ? C8 C9 C10 119.0(3) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? N1 C1 C2 117.8(3) . . ? N1 C1 H1A 121.1 . . ? C2 C1 H1A 121.1 . . ? C5 C4 C3 118.6(3) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C12 C11 C10 118.3(3) . . ? C12 C11 H11A 120.9 . . ? C10 C11 H11A 120.9 . . ? N3 C12 C11 122.7(3) . . ? N3 C12 H12A 118.6 . . ? C11 C12 H12A 118.6 . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10A 120.3 . . ? C11 C10 H10A 120.3 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.771 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.084 # Attachment '- Complex 2.cif' data_cp53c _database_code_depnum_ccdc_archive 'CCDC 846481' #TrackingRef '- Complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 N6 O10 Zn' _chemical_formula_weight 469.68 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.8777(6) _cell_length_b 11.2057(11) _cell_length_c 12.8526(12) _cell_angle_alpha 90.00 _cell_angle_beta 113.523(7) _cell_angle_gamma 90.00 _cell_volume 908.23(15) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9410 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 27.32 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6362 _exptl_absorpt_correction_T_max 0.7268 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5330 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.75 _reflns_number_total 1900 _reflns_number_gt 1706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.1829P] 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 1900 _refine_ls_number_parameters 145 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.055 _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 0.5000 0.0000 0.0000 0.04436(11) Uani 1 2 d S . . O1 O 0.73109(19) -0.13076(10) 0.03656(12) 0.0544(3) Uani 1 1 d . . . O2 O 0.4434(4) -0.05348(15) 0.14389(14) 0.0848(6) Uani 1 1 d D . . H21 H 0.394(6) -0.118(3) 0.150(3) 0.127 Uiso 1 1 d D . . H22 H 0.456(7) -0.016(3) 0.198(3) 0.127 Uiso 1 1 d D . . N1 N 0.7940(2) -0.32003(14) 0.00463(13) 0.0471(3) Uani 1 1 d D . . H1N H 0.755(3) -0.3855(18) -0.0296(18) 0.056 Uiso 1 1 d D . . H2N H 0.926(3) -0.3053(19) 0.0431(18) 0.056 Uiso 1 1 d D . . N2 N 0.3190(2) -0.14763(11) -0.08550(10) 0.0379(3) Uani 1 1 d . . . C1 C 0.6662(2) -0.23002(14) -0.00650(13) 0.0410(3) Uani 1 1 d . . . C2 C 0.4318(2) -0.24809(13) -0.07274(12) 0.0354(3) Uani 1 1 d . . . C3 C 0.1080(2) -0.15315(15) -0.13972(13) 0.0435(3) Uani 1 1 d . . . H3A H 0.0273 -0.0822 -0.1484 0.052 Uiso 1 1 calc R . . C4 C 0.0040(3) -0.25845(16) -0.18341(14) 0.0464(4) Uani 1 1 d . . . H4A H -0.1459 -0.2597 -0.2228 0.056 Uiso 1 1 calc R . . C5 C 0.1197(3) -0.36139(15) -0.16923(14) 0.0458(4) Uani 1 1 d . . . H5A H 0.0506 -0.4351 -0.1977 0.055 Uiso 1 1 calc R . . C6 C 0.3383(2) -0.35679(14) -0.11293(13) 0.0404(3) Uani 1 1 d . . . H6A H 0.4218 -0.4269 -0.1023 0.049 Uiso 1 1 calc R . . O3 O 0.75629(18) 0.23206(10) 0.37435(10) 0.0454(3) Uani 1 1 d . . . O4 O 0.7599(2) 0.04048(12) 0.37677(14) 0.0616(4) Uani 1 1 d . . . O5 O 0.46500(19) 0.13301(13) 0.30473(14) 0.0653(4) Uani 1 1 d . . . N3 N 0.6591(2) 0.13540(11) 0.35206(10) 0.0383(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.05485(18) 0.02909(15) 0.04720(16) -0.00275(9) 0.01832(12) -0.00534(10) O1 0.0434(6) 0.0390(6) 0.0690(8) -0.0090(5) 0.0099(5) -0.0054(5) O2 0.1549(17) 0.0539(9) 0.0631(9) -0.0201(7) 0.0618(10) -0.0492(10) N1 0.0360(7) 0.0443(8) 0.0583(8) -0.0058(6) 0.0160(6) 0.0001(6) N2 0.0406(6) 0.0322(6) 0.0395(6) 0.0011(5) 0.0144(5) -0.0006(5) C1 0.0388(8) 0.0389(8) 0.0442(8) -0.0006(6) 0.0155(6) -0.0032(6) C2 0.0378(7) 0.0337(7) 0.0358(6) -0.0001(5) 0.0158(6) -0.0014(6) C3 0.0406(8) 0.0432(8) 0.0441(8) 0.0060(6) 0.0143(6) 0.0058(6) C4 0.0363(7) 0.0559(10) 0.0435(8) 0.0006(7) 0.0121(6) -0.0023(7) C5 0.0445(8) 0.0446(9) 0.0480(8) -0.0091(7) 0.0181(7) -0.0114(7) C6 0.0426(8) 0.0357(7) 0.0453(8) -0.0038(6) 0.0200(6) -0.0021(6) O3 0.0425(6) 0.0332(6) 0.0586(7) -0.0007(5) 0.0180(5) -0.0020(4) O4 0.0594(8) 0.0342(6) 0.0979(10) 0.0101(7) 0.0384(7) 0.0088(6) O5 0.0355(6) 0.0585(8) 0.0881(10) -0.0023(7) 0.0100(6) -0.0036(5) N3 0.0400(7) 0.0350(7) 0.0403(6) -0.0012(5) 0.0164(5) 0.0009(5) _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 2.0731(12) 3_655 ? Zn1 O1 2.0731(12) . ? Zn1 N2 2.0980(12) 3_655 ? Zn1 N2 2.0981(12) . ? Zn1 O2 2.1227(15) . ? Zn1 O2 2.1227(15) 3_655 ? O1 C1 1.2431(19) . ? O2 H21 0.81(3) . ? O2 H22 0.78(3) . ? N1 C1 1.308(2) . ? N1 H1N 0.84(2) . ? N1 H2N 0.86(2) . ? N2 C3 1.337(2) . ? N2 C2 1.3394(19) . ? C1 C2 1.506(2) . ? C2 C6 1.378(2) . ? C3 C4 1.378(2) . ? C3 H3A 0.9500 . ? C4 C5 1.372(2) . ? C4 H4A 0.9500 . ? C5 C6 1.385(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? O3 N3 1.2447(16) . ? O4 N3 1.2399(18) . ? O5 N3 1.2267(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 179.998(1) 3_655 . ? O1 Zn1 N2 78.60(5) 3_655 3_655 ? O1 Zn1 N2 101.40(5) . 3_655 ? O1 Zn1 N2 101.40(5) 3_655 . ? O1 Zn1 N2 78.60(5) . . ? N2 Zn1 N2 180.0 3_655 . ? O1 Zn1 O2 90.37(8) 3_655 . ? O1 Zn1 O2 89.63(8) . . ? N2 Zn1 O2 92.47(5) 3_655 . ? N2 Zn1 O2 87.53(5) . . ? O1 Zn1 O2 89.63(8) 3_655 3_655 ? O1 Zn1 O2 90.37(8) . 3_655 ? N2 Zn1 O2 87.53(5) 3_655 3_655 ? N2 Zn1 O2 92.47(5) . 3_655 ? O2 Zn1 O2 180.0 . 3_655 ? C1 O1 Zn1 115.14(10) . . ? Zn1 O2 H21 124(3) . . ? Zn1 O2 H22 128(3) . . ? H21 O2 H22 107(3) . . ? C1 N1 H1N 123.6(14) . . ? C1 N1 H2N 115.1(15) . . ? H1N N1 H2N 121(2) . . ? C3 N2 C2 118.67(13) . . ? C3 N2 Zn1 127.09(11) . . ? C2 N2 Zn1 113.90(10) . . ? O1 C1 N1 122.33(15) . . ? O1 C1 C2 119.02(14) . . ? N1 C1 C2 118.64(14) . . ? N2 C2 C6 122.44(13) . . ? N2 C2 C1 113.14(13) . . ? C6 C2 C1 124.37(14) . . ? N2 C3 C4 122.08(15) . . ? N2 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C5 C4 C3 119.11(14) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 119.30(15) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C2 C6 C5 118.39(15) . . ? C2 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? O5 N3 O4 119.67(14) . . ? O5 N3 O3 120.75(13) . . ? O4 N3 O3 119.57(13) . . ? 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 O2 H21 O3 0.81(3) 1.93(3) 2.7310(18) 166(4) 2_645 O2 H22 O5 0.78(3) 2.15(3) 2.901(2) 161(3) . O2 H22 O4 0.78(3) 2.50(4) 3.099(2) 135(4) . N1 H1N O4 0.84(2) 2.12(2) 2.924(2) 159(2) 4 N1 H2N O3 0.86(2) 2.05(2) 2.9129(19) 176(2) 2_745 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.232 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.038 # Attachment '- Complex 3.cif' data_kk135d _database_code_depnum_ccdc_archive 'CCDC 846482' #TrackingRef '- Complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 F2 N8 O10 P2 Zn2 ' _chemical_formula_sum 'C24 H24 F2 N8 O10 P2 Zn2 ' _chemical_formula_weight 815.23 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 1 21/n 1' _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 9.1885(3) _cell_length_b 12.1035(5) _cell_length_c 13.9159(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.663(3) _cell_angle_gamma 90.00 _cell_volume 1547.53(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8696 _cell_measurement_theta_min 3.1286 _cell_measurement_theta_max 30.3464 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6410 _exptl_absorpt_correction_T_max 0.7857 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-3 with Sapphire CCD' _diffrn_measurement_method '\w/\f scans' _diffrn_detector_area_resol_mean 16.0288 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12593 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3695 _reflns_number_gt 3031 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997' _computing_molecular_graphics ; PLATON (Spek, 1990); MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999' _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^)+(0.0380P)^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 3695 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0582 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.025 _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 Zn Zn 0.170520(17) 0.163697(13) 0.020383(11) 0.01406(6) Uani 1 1 d . . . C1 C 0.40926(17) 0.19167(12) 0.18279(11) 0.0188(3) Uani 1 1 d . . . H1 H 0.3302 0.2009 0.2232 0.023 Uiso 1 1 calc R . . C2 C 0.54785(17) 0.20074(13) 0.22179(12) 0.0210(3) Uani 1 1 d . . . H2 H 0.5618 0.2174 0.2865 0.025 Uiso 1 1 calc R . . C3 C 0.66499(18) 0.18439(13) 0.16225(12) 0.0239(4) Uani 1 1 d . . . H3 H 0.7595 0.1904 0.1862 0.029 Uiso 1 1 calc R . . C4 C 0.64029(17) 0.15893(12) 0.06643(12) 0.0224(3) Uani 1 1 d . . . H4 H 0.7178 0.1457 0.0256 0.027 Uiso 1 1 calc R . . C5 C 0.49818(16) 0.15348(11) 0.03243(11) 0.0169(3) Uani 1 1 d . . . C6 C 0.46310(17) 0.12570(12) -0.06757(11) 0.0192(3) Uani 1 1 d . . . H6 H 0.5363 0.1119 -0.1116 0.023 Uiso 1 1 calc R . . C7 C 0.26493(18) 0.40061(13) -0.06604(12) 0.0245(4) Uani 1 1 d . . . H7 H 0.3053 0.3603 -0.1160 0.029 Uiso 1 1 calc R . . C8 C 0.2778(2) 0.51508(14) -0.06758(14) 0.0346(4) Uani 1 1 d . . . H8 H 0.3262 0.5506 -0.1171 0.042 Uiso 1 1 calc R . . C9 C 0.2166(2) 0.57498(15) 0.00672(14) 0.0405(5) Uani 1 1 d . . . H9 H 0.2222 0.6517 0.0075 0.049 Uiso 1 1 calc R . . C10 C 0.1477(2) 0.51925(13) 0.07919(13) 0.0328(4) Uani 1 1 d . . . H10 H 0.1067 0.5580 0.1298 0.039 Uiso 1 1 calc R . . C11 C 0.13976(17) 0.40484(12) 0.07640(11) 0.0212(3) Uani 1 1 d . . . C12 C 0.07023(17) 0.34235(12) 0.15283(12) 0.0205(3) Uani 1 1 d . . . H12 H 0.0273 0.3787 0.2041 0.025 Uiso 1 1 calc R . . N1 N 0.38336(13) 0.17043(9) 0.09019(9) 0.0155(3) Uani 1 1 d . . . N2 N 0.32962(14) 0.12094(10) -0.09251(9) 0.0171(3) Uani 1 1 d . . . N3 N 0.19748(14) 0.34581(10) 0.00366(9) 0.0188(3) Uani 1 1 d . . . N4 N 0.06926(13) 0.23700(10) 0.14816(9) 0.0167(3) Uani 1 1 d . . . O1 O 0.30426(13) 0.09169(9) -0.18700(7) 0.0225(2) Uani 1 1 d . . . HO1 H 0.216(2) 0.0709(16) -0.1873(13) 0.034 Uiso 1 1 d . . . O2 O 0.01123(12) 0.18645(9) 0.22794(8) 0.0198(2) Uani 1 1 d D . . HO2 H 0.003(2) 0.1224(12) 0.2126(14) 0.030 Uiso 1 1 d D . . O3 O 0.15233(11) 0.00544(8) 0.05930(8) 0.0181(2) Uani 1 1 d . . . O4 O -0.00418(11) 0.17108(8) -0.06827(8) 0.0180(2) Uani 1 1 d . . . O5 O -0.03556(12) -0.01860(9) 0.18971(7) 0.0215(2) Uani 1 1 d . . . F F 0.19123(10) -0.12666(8) 0.18681(7) 0.0257(2) Uani 1 1 d . . . P P 0.06874(4) -0.07308(3) 0.12059(3) 0.01530(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.01395(10) 0.01568(9) 0.01259(10) -0.00105(7) 0.00235(6) -0.00117(7) C1 0.0171(8) 0.0214(7) 0.0180(8) -0.0034(6) 0.0020(6) 0.0017(6) C2 0.0212(8) 0.0231(8) 0.0187(8) -0.0039(6) -0.0032(6) 0.0020(6) C3 0.0149(8) 0.0273(8) 0.0295(9) -0.0019(7) -0.0029(6) 0.0013(6) C4 0.0155(8) 0.0241(8) 0.0277(9) -0.0034(7) 0.0059(6) 0.0009(6) C5 0.0187(8) 0.0138(7) 0.0182(8) -0.0008(6) 0.0041(6) -0.0020(6) C6 0.0169(8) 0.0235(7) 0.0174(8) -0.0012(6) 0.0079(6) -0.0005(6) C7 0.0292(9) 0.0255(8) 0.0187(8) 0.0003(7) -0.0014(7) -0.0040(7) C8 0.0475(12) 0.0262(9) 0.0301(10) 0.0077(8) -0.0014(8) -0.0109(8) C9 0.0633(14) 0.0186(9) 0.0395(12) 0.0015(8) -0.0053(10) -0.0073(9) C10 0.0473(12) 0.0197(8) 0.0314(10) -0.0039(7) -0.0010(8) 0.0020(8) C11 0.0237(8) 0.0201(7) 0.0199(8) -0.0043(6) -0.0038(6) 0.0020(6) C12 0.0206(8) 0.0229(8) 0.0179(8) -0.0057(6) -0.0002(6) 0.0044(6) N1 0.0157(6) 0.0151(6) 0.0157(6) -0.0025(5) 0.0026(5) -0.0006(5) N2 0.0217(7) 0.0167(6) 0.0131(6) -0.0016(5) 0.0040(5) -0.0036(5) N3 0.0202(7) 0.0187(6) 0.0174(7) -0.0006(5) -0.0019(5) -0.0019(5) N4 0.0137(6) 0.0222(6) 0.0141(6) -0.0006(5) 0.0007(5) -0.0003(5) O1 0.0216(6) 0.0331(6) 0.0128(5) -0.0046(5) 0.0041(4) -0.0081(5) O2 0.0198(6) 0.0232(5) 0.0166(6) -0.0016(4) 0.0060(4) -0.0022(5) O3 0.0179(6) 0.0170(5) 0.0195(5) 0.0016(4) 0.0053(4) -0.0007(4) O4 0.0190(6) 0.0169(5) 0.0180(5) 0.0004(4) -0.0019(4) -0.0009(4) O5 0.0220(6) 0.0253(6) 0.0172(6) -0.0032(4) 0.0052(4) -0.0062(5) F 0.0243(5) 0.0279(5) 0.0246(5) 0.0073(4) -0.0083(4) -0.0034(4) P 0.01496(19) 0.01730(18) 0.01364(19) 0.00143(14) 0.00027(14) -0.00231(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 Zn O3 1.9981(10) . ? Zn O4 2.0152(11) . ? Zn N1 2.1751(13) . ? Zn N4 2.2030(12) . ? Zn N2 2.2195(12) . ? Zn N3 2.2306(12) . ? C1 N1 1.333(2) . ? C1 C2 1.383(2) . ? C1 H1 0.9300 . ? C2 C3 1.380(2) . ? C2 H2 0.9300 . ? C3 C4 1.385(2) . ? C3 H3 0.9300 . ? C4 C5 1.385(2) . ? C4 H4 0.9300 . ? C5 N1 1.3494(18) . ? C5 C6 1.464(2) . ? C6 N2 1.2720(19) . ? C6 H6 0.9300 . ? C7 N3 1.334(2) . ? C7 C8 1.391(2) . ? C7 H7 0.9300 . ? C8 C9 1.387(3) . ? C8 H8 0.9300 . ? C9 C10 1.374(3) . ? C9 H9 0.9300 . ? C10 C11 1.387(2) . ? C10 H10 0.9300 . ? C11 N3 1.3524(19) . ? C11 C12 1.458(2) . ? C12 N4 1.2768(19) . ? C12 H12 0.9300 . ? N2 O1 1.3791(16) . ? N4 O2 1.3801(16) . ? O1 HO1 0.849(19) . ? O2 HO2 0.807(14) . ? O3 P 1.4952(11) . ? O4 P 1.5096(10) 3 ? O5 P 1.5165(11) . ? F P 1.5851(9) . ? P O4 1.5097(10) 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 O3 Zn O4 98.04(4) . . ? O3 Zn N1 89.57(4) . . ? O4 Zn N1 167.82(4) . . ? O3 Zn N4 97.46(4) . . ? O4 Zn N4 97.78(4) . . ? N1 Zn N4 90.59(4) . . ? O3 Zn N2 91.50(4) . . ? O4 Zn N2 95.94(5) . . ? N1 Zn N2 74.26(5) . . ? N4 Zn N2 162.37(5) . . ? O3 Zn N3 170.18(5) . . ? O4 Zn N3 88.91(4) . . ? N1 Zn N3 84.79(4) . . ? N4 Zn N3 74.61(5) . . ? N2 Zn N3 94.69(5) . . ? N1 C1 C2 123.24(14) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.29(15) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 119.32(15) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 118.87(14) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 121.98(14) . . ? N1 C5 C6 115.85(13) . . ? C4 C5 C6 122.14(14) . . ? N2 C6 C5 118.08(13) . . ? N2 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? N3 C7 C8 123.16(16) . . ? N3 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C9 C8 C7 118.29(17) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 118.99(16) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 119.62(17) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N3 C11 C10 121.81(15) . . ? N3 C11 C12 116.80(13) . . ? C10 C11 C12 121.38(15) . . ? N4 C12 C11 118.92(14) . . ? N4 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C1 N1 C5 118.24(13) . . ? C1 N1 Zn 126.06(10) . . ? C5 N1 Zn 115.68(10) . . ? C6 N2 O1 115.06(12) . . ? C6 N2 Zn 115.93(10) . . ? O1 N2 Zn 129.00(9) . . ? C7 N3 C11 118.11(13) . . ? C7 N3 Zn 128.35(11) . . ? C11 N3 Zn 113.51(10) . . ? C12 N4 O2 113.85(12) . . ? C12 N4 Zn 116.14(10) . . ? O2 N4 Zn 129.90(9) . . ? N2 O1 HO1 103.3(13) . . ? N4 O2 HO2 104.5(14) . . ? P O3 Zn 144.00(7) . . ? P O4 Zn 124.49(6) 3 . ? O3 P O4 115.21(6) . 3 ? O3 P O5 114.71(6) . . ? O4 P O5 113.57(6) 3 . ? O3 P F 103.04(6) . . ? O4 P F 103.37(6) 3 . ? O5 P F 105.00(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.310 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.059