Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;Symmetrical and unsymmetrical dizinc complexes as models for the active site of hydrolytic enzymes ; _publ_contact_author_name 'Ebbe Nordlander' _publ_contact_author_email EBBE.NORDLANDER@INORG.LU.SE loop_ _publ_author_name 'Ebbe Nordlander' 'Matti Haukka' 'Martin Jarenmark' 'Sascha Kappen' # Attachment 'Structures 1 and 3.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 659750' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H62 N8 Na3 O24 Zn4, F6 P' _chemical_formula_sum 'C58 H66 F6 N8 Na3 O24 P Zn4' _chemical_formula_weight 1734.61 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 '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' 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 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 19.5230(5) _cell_length_b 10.1399(2) _cell_length_c 18.1745(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.181(3) _cell_angle_gamma 90.00 _cell_volume 3597.83(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10701 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 1.454 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5519 _exptl_absorpt_correction_T_max 0.8007 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _publ_section_exptl_refinement ; THe Na2, O13 , and O14 atoms are disordered over two sites with equal occupancies. All hydrogens connectedted to the Na bound oxygens have been omitted. Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.36 \%A from atom O14 and the deepest hole is located 0.76 \%A from atom Na1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36287 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7067 _reflns_number_gt 6141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1e (Brandenburg, 2007)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0774P)^2^+15.7925P] 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 7067 _refine_ls_number_parameters 487 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1736 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.117 _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 0.19479(3) 0.34274(5) 0.01095(3) 0.03008(17) Uani 1 1 d . . . Zn2 Zn 0.20225(3) 0.68272(5) -0.02055(3) 0.02916(17) Uani 1 1 d . . . P1 P 0.5000 1.0962(2) 0.2500 0.0414(5) Uani 1 2 d S . . Na1 Na 0.08490(16) 0.0210(3) -0.04236(16) 0.0652(7) Uani 1 1 d . . . O1 O 0.14003(19) 0.1665(4) 0.0410(2) 0.0414(9) Uani 1 1 d . . . O2 O 0.1011(3) 0.0595(5) 0.1396(3) 0.0697(14) Uani 1 1 d . . . O3 O 0.16210(18) 0.3625(4) -0.0960(2) 0.0361(8) Uani 1 1 d . . . O4 O 0.1712(2) 0.5861(4) -0.1178(2) 0.0475(10) Uani 1 1 d . . . O5 O 0.24926(17) 0.5140(3) 0.01442(19) 0.0312(7) Uani 1 1 d . . . O6 O 0.10879(19) 0.4407(4) 0.0558(2) 0.0416(9) Uani 1 1 d . . . O7 O 0.10835(18) 0.6562(4) 0.0277(2) 0.0395(9) Uani 1 1 d . . . O8 O 0.1796(2) 0.8591(4) -0.0782(2) 0.0405(9) Uani 1 1 d . . . O9 O 0.2084(2) 0.9582(5) -0.1831(2) 0.0594(12) Uani 1 1 d . . . F10 F 0.4852(3) 1.0853(12) 0.3326(3) 0.168(4) Uani 1 1 d . . . F11 F 0.4205(2) 1.0967(6) 0.2339(3) 0.0926(17) Uani 1 1 d . . . N1 N 0.2872(2) 0.2336(4) -0.0188(2) 0.0296(9) Uani 1 1 d . . . N2 N 0.2362(2) 0.2940(4) 0.1206(2) 0.0302(9) Uani 1 1 d . . . N3 N 0.2409(2) 0.7891(4) 0.0743(2) 0.0323(9) Uani 1 1 d . . . N4 N 0.3032(2) 0.7471(4) -0.0624(2) 0.0300(9) Uani 1 1 d . . . C1 C 0.3149(3) 0.2273(5) -0.0859(3) 0.0344(11) Uani 1 1 d . . . H1 H 0.2878 0.2529 -0.1270 0.041 Uiso 1 1 calc R . . C2 C 0.3810(3) 0.1854(6) -0.0981(3) 0.0403(12) Uani 1 1 d . . . H2 H 0.3983 0.1774 -0.1467 0.048 Uiso 1 1 calc R . . C3 C 0.4217(3) 0.1551(6) -0.0379(3) 0.0406(13) Uani 1 1 d . . . H3 H 0.4679 0.1282 -0.0447 0.049 Uiso 1 1 calc R . . C4 C 0.3947(3) 0.1643(5) 0.0321(3) 0.0344(11) Uani 1 1 d . . . H4 H 0.4223 0.1469 0.0742 0.041 Uiso 1 1 calc R . . C5 C 0.3262(2) 0.1997(5) 0.0395(3) 0.0280(10) Uani 1 1 d . . . C6 C 0.2902(3) 0.1930(5) 0.1127(3) 0.0326(11) Uani 1 1 d . . . H6A H 0.2694 0.1046 0.1185 0.039 Uiso 1 1 calc R . . H6B H 0.3243 0.2047 0.1526 0.039 Uiso 1 1 calc R . . C7 C 0.1361(3) 0.1486(6) 0.1092(4) 0.0447(13) Uani 1 1 d . . . C8 C 0.1767(3) 0.2374(6) 0.1598(3) 0.0405(12) Uani 1 1 d . . . H8A H 0.1470 0.3095 0.1779 0.049 Uiso 1 1 calc R . . H8B H 0.1930 0.1863 0.2029 0.049 Uiso 1 1 calc R . . C9 C 0.0834(2) 0.5531(5) 0.0576(3) 0.0317(10) Uani 1 1 d . . . C10 C 0.0167(3) 0.5712(6) 0.0979(4) 0.0479(14) Uani 1 1 d . . . H10A H -0.0186 0.6012 0.0633 0.072 Uiso 1 1 calc R . . H10B H 0.0226 0.6372 0.1368 0.072 Uiso 1 1 calc R . . H10C H 0.0027 0.4872 0.1198 0.072 Uiso 1 1 calc R . . C11 C 0.1563(3) 0.4669(7) -0.1348(3) 0.0462(14) Uani 1 1 d . . . C12 C 0.1280(4) 0.4411(8) -0.2122(3) 0.0638(19) Uani 1 1 d . . . H12A H 0.1661 0.4307 -0.2467 0.096 Uiso 1 1 calc R . . H12B H 0.0994 0.5156 -0.2276 0.096 Uiso 1 1 calc R . . H12C H 0.1004 0.3603 -0.2119 0.096 Uiso 1 1 calc R . . C13 C 0.2145(3) 0.7828(6) 0.1420(3) 0.0406(13) Uani 1 1 d . . . H13 H 0.1690 0.7514 0.1476 0.049 Uiso 1 1 calc R . . C14 C 0.2505(4) 0.8198(6) 0.2036(3) 0.0501(16) Uani 1 1 d . . . H14 H 0.2297 0.8164 0.2507 0.060 Uiso 1 1 calc R . . C15 C 0.3171(4) 0.8619(6) 0.1961(3) 0.0505(16) Uani 1 1 d . . . H15 H 0.3431 0.8875 0.2380 0.061 Uiso 1 1 calc R . . C16 C 0.3459(3) 0.8662(5) 0.1263(3) 0.0410(13) Uani 1 1 d . . . H16 H 0.3922 0.8922 0.1197 0.049 Uiso 1 1 calc R . . C17 C 0.3052(3) 0.8316(5) 0.0659(3) 0.0333(11) Uani 1 1 d . . . C18 C 0.3295(3) 0.8497(5) -0.0122(3) 0.0340(11) Uani 1 1 d . . . H18A H 0.3144 0.9372 -0.0302 0.041 Uiso 1 1 calc R . . H18B H 0.3801 0.8481 -0.0128 0.041 Uiso 1 1 calc R . . C19 C 0.2865(3) 0.8022(6) -0.1348(3) 0.0376(12) Uani 1 1 d . . . H19A H 0.2818 0.7298 -0.1710 0.045 Uiso 1 1 calc R . . H19B H 0.3242 0.8605 -0.1512 0.045 Uiso 1 1 calc R . . C20 C 0.2196(3) 0.8808(5) -0.1316(3) 0.0383(12) Uani 1 1 d . . . C21 C 0.3529(3) 0.6366(5) -0.0674(3) 0.0326(11) Uani 1 1 d . . . H21A H 0.3963 0.6690 -0.0888 0.039 Uiso 1 1 calc R . . H21B H 0.3343 0.5675 -0.1004 0.039 Uiso 1 1 calc R . . C22 C 0.3666(3) 0.5783(5) 0.0072(3) 0.0307(10) Uani 1 1 d . . . C23 C 0.4309(3) 0.5853(5) 0.0405(3) 0.0353(11) Uani 1 1 d . . . H23 H 0.4678 0.6238 0.0142 0.042 Uiso 1 1 calc R . . C24 C 0.4428(3) 0.5373(5) 0.1113(3) 0.0357(11) Uani 1 1 d . . . C25 C 0.5122(3) 0.5495(7) 0.1480(3) 0.0456(14) Uani 1 1 d . . . H25A H 0.5474 0.5634 0.1104 0.068 Uiso 1 1 calc R . . H25B H 0.5224 0.4684 0.1753 0.068 Uiso 1 1 calc R . . H25C H 0.5119 0.6245 0.1820 0.068 Uiso 1 1 calc R . . C26 C 0.3878(3) 0.4802(5) 0.1485(3) 0.0346(11) Uani 1 1 d . . . H26 H 0.3949 0.4464 0.1967 0.042 Uiso 1 1 calc R . . C27 C 0.3226(3) 0.4714(5) 0.1168(3) 0.0306(10) Uani 1 1 d . . . C28 C 0.3117(2) 0.5212(5) 0.0455(3) 0.0296(10) Uani 1 1 d . . . C29 C 0.2630(3) 0.4141(5) 0.1576(3) 0.0341(11) Uani 1 1 d . . . H29A H 0.2774 0.3915 0.2083 0.041 Uiso 1 1 calc R . . H29B H 0.2260 0.4807 0.1608 0.041 Uiso 1 1 calc R . . F30 F 0.5000 0.9439(10) 0.2500 0.194(7) Uani 1 2 d S . . F31 F 0.5000 1.2423(9) 0.2500 0.198(7) Uani 1 2 d S . . O12 O 0.0364(2) -0.1050(5) 0.0477(3) 0.0679(13) Uani 1 1 d . . . O13 O 0.1094(3) 0.1419(5) -0.1456(3) 0.0699(14) Uani 1 1 d . . . Na2 Na 0.0916(3) -0.0083(6) -0.2316(3) 0.0637(15) Uani 0.50 1 d P . . O14 O 0.0511(6) -0.1624(14) -0.1426(7) 0.089(4) Uani 0.50 1 d PU . . O15 O -0.0263(7) 0.0574(19) -0.2423(10) 0.126(5) Uani 0.50 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0282(3) 0.0288(3) 0.0333(3) 0.0080(2) 0.0002(2) 0.0019(2) Zn2 0.0300(3) 0.0293(3) 0.0282(3) 0.0040(2) 0.0020(2) 0.0017(2) P1 0.0304(10) 0.0527(12) 0.0412(11) 0.000 -0.0110(8) 0.000 Na1 0.0747(19) 0.0532(15) 0.0675(17) 0.0084(13) -0.0193(14) -0.0139(13) O1 0.036(2) 0.037(2) 0.051(2) 0.0067(17) -0.0037(17) -0.0057(16) O2 0.075(3) 0.062(3) 0.072(3) 0.003(3) 0.024(3) -0.026(3) O3 0.0359(19) 0.0361(19) 0.0362(19) 0.0092(16) -0.0039(15) -0.0003(15) O4 0.053(2) 0.047(2) 0.043(2) -0.0018(18) -0.0096(18) -0.0063(19) O5 0.0288(17) 0.0283(17) 0.0364(18) 0.0034(14) 0.0013(14) 0.0020(13) O6 0.0331(19) 0.040(2) 0.052(2) 0.0104(17) 0.0095(17) 0.0064(16) O7 0.0303(18) 0.039(2) 0.050(2) 0.0131(17) 0.0072(16) 0.0085(15) O8 0.047(2) 0.041(2) 0.0335(19) 0.0102(16) 0.0023(17) 0.0034(17) O9 0.065(3) 0.068(3) 0.045(2) 0.030(2) 0.005(2) 0.008(2) F10 0.075(4) 0.371(13) 0.058(3) 0.040(5) -0.013(3) -0.049(6) F11 0.034(2) 0.147(5) 0.096(3) -0.031(3) -0.021(2) 0.011(3) N1 0.034(2) 0.0238(19) 0.031(2) -0.0006(16) -0.0028(17) 0.0007(16) N2 0.032(2) 0.029(2) 0.030(2) 0.0057(17) 0.0060(17) 0.0032(17) N3 0.044(2) 0.026(2) 0.027(2) 0.0005(16) 0.0001(18) 0.0099(18) N4 0.036(2) 0.030(2) 0.0241(19) 0.0005(16) 0.0019(16) -0.0029(17) C1 0.041(3) 0.030(3) 0.032(3) -0.003(2) -0.001(2) -0.003(2) C2 0.040(3) 0.045(3) 0.036(3) -0.007(2) 0.007(2) -0.006(2) C3 0.028(3) 0.045(3) 0.050(3) -0.008(2) 0.005(2) -0.004(2) C4 0.031(3) 0.030(3) 0.042(3) -0.002(2) -0.002(2) 0.000(2) C5 0.031(2) 0.022(2) 0.031(2) -0.0001(18) -0.0025(19) 0.0016(18) C6 0.032(3) 0.031(2) 0.034(3) 0.006(2) -0.003(2) 0.006(2) C7 0.039(3) 0.041(3) 0.054(4) 0.008(3) 0.011(3) -0.002(2) C8 0.039(3) 0.044(3) 0.039(3) 0.013(2) 0.009(2) 0.002(2) C9 0.025(2) 0.037(3) 0.034(3) 0.004(2) -0.0010(19) 0.001(2) C10 0.037(3) 0.048(3) 0.059(4) 0.000(3) 0.016(3) 0.001(3) C11 0.038(3) 0.056(4) 0.044(3) 0.004(3) 0.004(2) -0.002(3) C12 0.074(5) 0.082(5) 0.036(3) 0.011(3) 0.010(3) 0.001(4) C13 0.053(3) 0.040(3) 0.029(3) -0.002(2) 0.006(2) 0.016(3) C14 0.076(5) 0.048(3) 0.027(3) -0.003(2) 0.006(3) 0.019(3) C15 0.082(5) 0.038(3) 0.031(3) -0.003(2) -0.015(3) 0.012(3) C16 0.055(3) 0.031(3) 0.037(3) 0.001(2) -0.012(2) 0.005(2) C17 0.047(3) 0.022(2) 0.031(3) -0.0022(19) -0.004(2) 0.004(2) C18 0.043(3) 0.027(2) 0.032(3) 0.002(2) -0.004(2) -0.005(2) C19 0.046(3) 0.044(3) 0.023(2) 0.008(2) 0.001(2) -0.006(2) C20 0.045(3) 0.036(3) 0.034(3) 0.005(2) -0.006(2) -0.006(2) C21 0.031(2) 0.037(3) 0.030(2) -0.002(2) 0.005(2) -0.003(2) C22 0.032(2) 0.027(2) 0.033(3) -0.0034(19) 0.004(2) 0.0011(19) C23 0.031(3) 0.037(3) 0.038(3) -0.006(2) 0.007(2) -0.002(2) C24 0.031(3) 0.037(3) 0.039(3) -0.007(2) -0.001(2) 0.002(2) C25 0.032(3) 0.055(4) 0.049(3) -0.003(3) -0.003(2) -0.003(3) C26 0.036(3) 0.035(3) 0.033(3) -0.003(2) 0.001(2) 0.004(2) C27 0.033(3) 0.029(2) 0.030(2) -0.0039(19) 0.006(2) 0.003(2) C28 0.028(2) 0.025(2) 0.035(3) -0.0008(19) 0.004(2) 0.0052(19) C29 0.033(3) 0.042(3) 0.028(2) 0.001(2) 0.005(2) 0.006(2) F30 0.117(8) 0.068(6) 0.40(2) 0.000 -0.021(11) 0.000 F31 0.130(9) 0.053(5) 0.41(2) 0.000 -0.037(11) 0.000 O12 0.050(3) 0.057(3) 0.096(4) 0.006(3) -0.003(3) 0.006(2) O13 0.086(4) 0.065(3) 0.058(3) 0.013(2) -0.011(3) 0.006(3) Na2 0.086(4) 0.063(3) 0.042(3) 0.001(2) 0.008(3) 0.008(3) O14 0.059(6) 0.121(8) 0.087(7) 0.028(6) -0.015(5) 0.009(5) O15 0.099(8) 0.168(9) 0.110(8) 0.052(8) -0.006(7) 0.029(7) _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 O5 2.037(3) . ? Zn1 O3 2.054(4) . ? Zn1 O6 2.116(4) . ? Zn1 O1 2.153(4) . ? Zn1 N1 2.186(4) . ? Zn1 N2 2.204(4) . ? Zn2 O5 2.042(3) . ? Zn2 O7 2.052(4) . ? Zn2 O4 2.108(4) . ? Zn2 O8 2.119(4) . ? Zn2 N3 2.168(4) . ? Zn2 N4 2.214(4) . ? P1 F31 1.481(9) . ? P1 F10 1.534(5) 2_655 ? P1 F10 1.534(5) . ? P1 F30 1.544(10) . ? P1 F11 1.579(4) 2_655 ? P1 F11 1.579(4) . ? Na1 O12 2.284(6) . ? Na1 O13 2.292(6) . ? Na1 O1 2.370(5) . ? Na1 O12 2.518(6) 3 ? Na1 O8 2.559(5) 1_545 ? Na1 O14 2.684(15) . ? Na1 Na2 3.456(6) . ? Na1 Na1 3.684(6) 3 ? O1 C7 1.257(7) . ? O2 C7 1.261(7) . ? O2 Na2 2.404(7) 4_556 ? O3 C11 1.276(7) . ? O4 C11 1.281(8) . ? O5 C28 1.344(6) . ? O6 C9 1.243(6) . ? O7 C9 1.276(6) . ? O8 C20 1.266(7) . ? O8 Na1 2.559(5) 1_565 ? O9 C20 1.241(7) . ? O9 Na2 2.466(8) 1_565 ? N1 C1 1.337(6) . ? N1 C5 1.346(6) . ? N2 C6 1.477(6) . ? N2 C8 1.479(6) . ? N2 C29 1.485(7) . ? N3 C17 1.336(7) . ? N3 C13 1.336(7) . ? N4 C19 1.465(6) . ? N4 C18 1.475(6) . ? N4 C21 1.484(6) . ? C1 C2 1.378(8) . ? C1 H1 0.9500 . ? C2 C3 1.384(8) . ? C2 H2 0.9500 . ? C3 C4 1.381(8) . ? C3 H3 0.9500 . ? C4 C5 1.393(7) . ? C4 H4 0.9500 . ? C5 C6 1.509(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.511(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(7) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.533(9) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.372(9) . ? C13 H13 0.9500 . ? C14 C15 1.377(10) . ? C14 H14 0.9500 . ? C15 C16 1.389(9) . ? C15 H15 0.9500 . ? C16 C17 1.397(7) . ? C16 H16 0.9500 . ? C17 C18 1.509(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.531(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C21 C22 1.504(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.392(7) . ? C22 C28 1.406(7) . ? C23 C24 1.394(8) . ? C23 H23 0.9500 . ? C24 C26 1.395(8) . ? C24 C25 1.514(7) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.399(7) . ? C26 H26 0.9500 . ? C27 C28 1.406(7) . ? C27 C29 1.499(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? O12 Na1 2.518(6) 3 ? O13 Na2 2.210(8) . ? Na2 O15 1.513(18) 2_554 ? Na2 O14 2.385(14) . ? Na2 O15 2.404(15) . ? Na2 O2 2.404(7) 4 ? Na2 O9 2.465(8) 1_545 ? Na2 Na2 3.636(13) 2_554 ? O15 O15 1.07(3) 2_554 ? O15 Na2 1.513(18) 2_554 ? 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 O5 Zn1 O3 96.13(14) . . ? O5 Zn1 O6 90.15(14) . . ? O3 Zn1 O6 94.25(15) . . ? O5 Zn1 O1 163.54(15) . . ? O3 Zn1 O1 99.65(15) . . ? O6 Zn1 O1 84.09(15) . . ? O5 Zn1 N1 90.45(14) . . ? O3 Zn1 N1 94.00(15) . . ? O6 Zn1 N1 171.62(15) . . ? O1 Zn1 N1 93.06(15) . . ? O5 Zn1 N2 88.46(15) . . ? O3 Zn1 N2 171.70(15) . . ? O6 Zn1 N2 92.64(15) . . ? O1 Zn1 N2 76.46(15) . . ? N1 Zn1 N2 79.02(15) . . ? O5 Zn2 O7 99.13(14) . . ? O5 Zn2 O4 89.97(15) . . ? O7 Zn2 O4 92.40(17) . . ? O5 Zn2 O8 162.55(14) . . ? O7 Zn2 O8 97.85(14) . . ? O4 Zn2 O8 85.33(16) . . ? O5 Zn2 N3 90.81(14) . . ? O7 Zn2 N3 92.00(17) . . ? O4 Zn2 N3 175.34(17) . . ? O8 Zn2 N3 92.57(15) . . ? O5 Zn2 N4 87.37(14) . . ? O7 Zn2 N4 169.45(15) . . ? O4 Zn2 N4 95.92(16) . . ? O8 Zn2 N4 76.45(15) . . ? N3 Zn2 N4 79.54(15) . . ? F31 P1 F10 94.1(5) . 2_655 ? F31 P1 F10 94.1(5) . . ? F10 P1 F10 171.7(9) 2_655 . ? F31 P1 F30 180.000(4) . . ? F10 P1 F30 85.9(5) 2_655 . ? F10 P1 F30 85.9(5) . . ? F31 P1 F11 89.8(2) . 2_655 ? F10 P1 F11 89.6(3) 2_655 2_655 ? F10 P1 F11 90.4(3) . 2_655 ? F30 P1 F11 90.2(2) . 2_655 ? F31 P1 F11 89.8(2) . . ? F10 P1 F11 90.4(3) 2_655 . ? F10 P1 F11 89.6(3) . . ? F30 P1 F11 90.2(2) . . ? F11 P1 F11 179.6(5) 2_655 . ? O12 Na1 O13 166.7(2) . . ? O12 Na1 O1 94.5(2) . . ? O13 Na1 O1 95.4(2) . . ? O12 Na1 O12 79.9(2) . 3 ? O13 Na1 O12 89.2(2) . 3 ? O1 Na1 O12 103.8(2) . 3 ? O12 Na1 O8 97.19(18) . 1_545 ? O13 Na1 O8 89.0(2) . 1_545 ? O1 Na1 O8 103.59(17) . 1_545 ? O12 Na1 O8 152.6(2) 3 1_545 ? O12 Na1 O14 89.8(3) . . ? O13 Na1 O14 82.3(3) . . ? O1 Na1 O14 167.1(3) . . ? O12 Na1 O14 88.8(3) 3 . ? O8 Na1 O14 63.8(3) 1_545 . ? O12 Na1 Na2 133.0(2) . . ? O13 Na1 Na2 39.00(17) . . ? O1 Na1 Na2 132.15(18) . . ? O12 Na1 Na2 91.69(19) 3 . ? O8 Na1 Na2 70.22(15) 1_545 . ? O14 Na1 Na2 43.5(3) . . ? O12 Na1 Na1 42.28(13) . 3 ? O13 Na1 Na1 126.4(2) . 3 ? O1 Na1 Na1 102.26(17) . 3 ? O12 Na1 Na1 37.60(14) 3 3 ? O8 Na1 Na1 133.17(16) 1_545 3 ? O14 Na1 Na1 89.1(3) . 3 ? Na2 Na1 Na1 116.29(16) . 3 ? C7 O1 Zn1 113.7(4) . . ? C7 O1 Na1 120.8(4) . . ? Zn1 O1 Na1 125.4(2) . . ? C7 O2 Na2 128.6(5) . 4_556 ? C11 O3 Zn1 129.1(4) . . ? C11 O4 Zn2 134.8(4) . . ? C28 O5 Zn1 122.1(3) . . ? C28 O5 Zn2 119.4(3) . . ? Zn1 O5 Zn2 118.07(16) . . ? C9 O6 Zn1 139.3(3) . . ? C9 O7 Zn2 129.2(3) . . ? C20 O8 Zn2 113.4(3) . . ? C20 O8 Na1 122.1(3) . 1_565 ? Zn2 O8 Na1 124.43(17) . 1_565 ? C20 O9 Na2 121.2(4) . 1_565 ? C1 N1 C5 118.4(4) . . ? C1 N1 Zn1 125.9(3) . . ? C5 N1 Zn1 113.6(3) . . ? C6 N2 C8 109.8(4) . . ? C6 N2 C29 111.2(4) . . ? C8 N2 C29 112.1(4) . . ? C6 N2 Zn1 109.1(3) . . ? C8 N2 Zn1 103.7(3) . . ? C29 N2 Zn1 110.7(3) . . ? C17 N3 C13 119.1(5) . . ? C17 N3 Zn2 113.2(3) . . ? C13 N3 Zn2 125.0(4) . . ? C19 N4 C18 111.3(4) . . ? C19 N4 C21 112.1(4) . . ? C18 N4 C21 110.2(4) . . ? C19 N4 Zn2 103.0(3) . . ? C18 N4 Zn2 107.6(3) . . ? C21 N4 Zn2 112.4(3) . . ? N1 C1 C2 122.9(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.5(5) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 118.4(5) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 122.1(5) . . ? N1 C5 C6 116.2(4) . . ? C4 C5 C6 121.6(4) . . ? N2 C6 C5 112.9(4) . . ? N2 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? N2 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O1 C7 O2 124.8(6) . . ? O1 C7 C8 118.7(5) . . ? O2 C7 C8 116.4(6) . . ? N2 C8 C7 110.4(4) . . ? N2 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N2 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O6 C9 O7 126.0(5) . . ? O6 C9 C10 118.0(5) . . ? O7 C9 C10 116.0(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 129.1(6) . . ? O3 C11 C12 113.3(6) . . ? O4 C11 C12 117.6(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 122.7(6) . . ? N3 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C13 C14 C15 119.0(6) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C16 119.0(6) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C15 C16 C17 118.6(6) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? N3 C17 C16 121.5(5) . . ? N3 C17 C18 116.4(4) . . ? C16 C17 C18 121.9(5) . . ? N4 C18 C17 112.8(4) . . ? N4 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? N4 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? N4 C19 C20 110.6(4) . . ? N4 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? O9 C20 O8 125.4(5) . . ? O9 C20 C19 116.7(5) . . ? O8 C20 C19 117.8(5) . . ? N4 C21 C22 110.9(4) . . ? N4 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? N4 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? C23 C22 C28 119.6(5) . . ? C23 C22 C21 122.0(4) . . ? C28 C22 C21 118.3(4) . . ? C22 C23 C24 122.0(5) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C23 C24 C26 117.7(5) . . ? C23 C24 C25 121.6(5) . . ? C26 C24 C25 120.7(5) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 C27 121.9(5) . . ? C24 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C26 C27 C28 119.4(5) . . ? C26 C27 C29 121.9(4) . . ? C28 C27 C29 118.7(4) . . ? O5 C28 C27 120.2(4) . . ? O5 C28 C22 120.4(4) . . ? C27 C28 C22 119.4(5) . . ? N2 C29 C27 111.6(4) . . ? N2 C29 H29A 109.3 . . ? C27 C29 H29A 109.3 . . ? N2 C29 H29B 109.3 . . ? C27 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? Na1 O12 Na1 100.1(2) . 3 ? Na2 O13 Na1 100.2(3) . . ? O15 Na2 O13 92.7(6) 2_554 . ? O15 Na2 O14 102.7(8) 2_554 . ? O13 Na2 O14 91.3(4) . . ? O15 Na2 O15 17.6(9) 2_554 . ? O13 Na2 O15 90.8(5) . . ? O14 Na2 O15 85.3(5) . . ? O15 Na2 O2 81.8(6) 2_554 4 ? O13 Na2 O2 145.6(3) . 4 ? O14 Na2 O2 123.1(5) . 4 ? O15 Na2 O2 93.3(5) . 4 ? O15 Na2 O9 161.8(7) 2_554 1_545 ? O13 Na2 O9 72.5(3) . 1_545 ? O14 Na2 O9 88.6(3) . 1_545 ? O15 Na2 O9 162.1(5) . 1_545 ? O2 Na2 O9 104.1(3) 4 1_545 ? O15 Na2 Na1 103.8(7) 2_554 . ? O13 Na2 Na1 40.75(17) . . ? O14 Na2 Na1 50.8(4) . . ? O15 Na2 Na1 91.0(4) . . ? O2 Na2 Na1 172.1(3) 4 . ? O9 Na2 Na1 72.16(18) 1_545 . ? O15 Na2 Na2 27.8(7) 2_554 2_554 ? O13 Na2 Na2 106.4(3) . 2_554 ? O14 Na2 Na2 78.3(3) . 2_554 ? O15 Na2 Na2 17.1(5) . 2_554 ? O2 Na2 Na2 84.3(2) 4 2_554 ? O9 Na2 Na2 166.8(3) 1_545 2_554 ? Na1 Na2 Na2 98.2(2) . 2_554 ? Na2 O14 Na1 85.7(5) . . ? O15 O15 Na2 137(2) 2_554 2_554 ? O15 O15 Na2 25.5(13) 2_554 . ? Na2 O15 Na2 135.1(12) 2_554 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.700 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.118 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 659751' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H78 N8 O10 Zn4, C2 H6 O, 2(F6 P), H2 O' _chemical_formula_sum 'C64 H86 F12 N8 O12 P2 Zn4' _chemical_formula_weight 1710.83 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' F F 0.0171 0.0103 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.5080(5) _cell_length_b 14.4476(3) _cell_length_c 21.2277(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.3150(10) _cell_angle_gamma 90.00 _cell_volume 7503.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 30194 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.10 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3520 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6990 _exptl_absorpt_correction_T_max 0.8694 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _publ_section_exptl_refinement ; Three methyl groups (C29-31) were disordered over two sites with occupancies 0.54/0.46. The anisotropic displacement parameters of these methy carbons were constrained to be equal. The ethanol solvent molecule was disordered over two sites around center an inversion center with equal occupancies. The carbon C33 of the ethanol solvent was restrained so that its Uij components approximate to isotropic behavior. The idealized positions of the H~2~O hydrogens were estimated with HYDROGEN (Nardelli, 1999)program and constrained to ride on their parent atom with U~iso~ = 1.5 (parent atom). These hydrogen atoms were disordered over two sites with equal occupancies. The OH hydrogen atom was located from the difference Fourier map but constrained to ride on its parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and also constrained to ride on their parent atoms, with C---H = 0.95-1.00 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.28 \%A from atom H33A and the deepest hole is located 0.78 \%A from atom P1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61458 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.15 _reflns_number_total 8289 _reflns_number_gt 6083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1e (Brandenburg, 2007)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0679P)^2^+17.9702P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8289 _refine_ls_number_parameters 479 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.251 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.907510(19) 0.06443(3) 0.030824(19) 0.02586(14) Uani 1 1 d . . . Zn2 Zn 0.931098(18) 0.10139(3) -0.123180(18) 0.02391(13) Uani 1 1 d . . . P1 P 0.86106(7) 0.55627(10) -0.26094(7) 0.0634(5) Uani 1 1 d . . . F1 F 0.8796(2) 0.6607(2) -0.24948(17) 0.1072(17) Uani 1 1 d . . . F2 F 0.8718(2) 0.5648(2) -0.33374(18) 0.1062(17) Uani 1 1 d . . . F3 F 0.84320(15) 0.4511(2) -0.27135(19) 0.0764(10) Uani 1 1 d . . . F4 F 0.85056(16) 0.5490(3) -0.18821(15) 0.0813(11) Uani 1 1 d . . . F5 F 0.92214(16) 0.5230(3) -0.2484(2) 0.0924(13) Uani 1 1 d . . . F6 F 0.7999(2) 0.5875(4) -0.2742(2) 0.123(2) Uani 1 1 d . . . O1 O 0.97517(11) 0.00550(18) 0.07248(11) 0.0279(6) Uani 1 1 d . . . O2 O 0.91725(11) 0.15227(18) -0.03775(11) 0.0281(6) Uani 1 1 d . . . O3 O 0.88173(12) -0.04796(19) -0.01779(12) 0.0330(6) Uani 1 1 d . . . O4 O 0.86697(13) 0.0100(2) -0.11451(13) 0.0366(7) Uani 1 1 d . . . O5 O 0.97052(12) -0.00434(19) -0.15988(12) 0.0328(6) Uani 1 1 d . . . N1 N 0.84025(15) 0.0697(2) 0.08667(15) 0.0331(8) Uani 1 1 d . . . N2 N 0.93234(14) 0.1730(2) 0.10084(14) 0.0290(7) Uani 1 1 d . . . N3 N 0.99344(13) 0.2036(2) -0.13379(14) 0.0272(7) Uani 1 1 d . . . N4 N 0.88542(13) 0.1966(2) -0.17948(14) 0.0257(7) Uani 1 1 d . . . C1 C 0.80147(18) 0.0047(3) 0.08665(19) 0.0374(10) Uani 1 1 d . . . H1 H 0.8021 -0.0441 0.0567 0.045 Uiso 1 1 calc R . . C2 C 0.7605(2) 0.0063(4) 0.1287(2) 0.0448(11) Uani 1 1 d . . . H2 H 0.7329 -0.0401 0.1274 0.054 Uiso 1 1 calc R . . C3 C 0.7604(2) 0.0770(4) 0.1729(2) 0.0492(13) Uani 1 1 d . . . H3 H 0.7334 0.0785 0.2033 0.059 Uiso 1 1 calc R . . C4 C 0.7998(2) 0.1450(4) 0.1723(2) 0.0441(12) Uani 1 1 d . . . H4 H 0.7999 0.1945 0.2018 0.053 Uiso 1 1 calc R . . C5 C 0.83925(18) 0.1402(3) 0.12824(18) 0.0345(10) Uani 1 1 d . . . C6 C 0.88227(19) 0.2134(3) 0.12420(19) 0.0365(10) Uani 1 1 d . . . H6A H 0.8687 0.2632 0.0953 0.044 Uiso 1 1 calc R . . H6B H 0.8904 0.2409 0.1664 0.044 Uiso 1 1 calc R . . C7 C 0.96344(18) 0.1228(3) 0.15119(17) 0.0307(9) Uani 1 1 d . . . H7A H 0.9384 0.1034 0.1837 0.037 Uiso 1 1 calc R . . H7B H 0.9913 0.1646 0.1714 0.037 Uiso 1 1 calc R . . C8 C 0.99148(16) 0.0380(3) 0.12559(18) 0.0274(8) Uani 1 1 d . . . C9 C 0.96773(18) 0.2419(3) 0.07074(18) 0.0343(9) Uani 1 1 d . . . H9A H 0.9995 0.2096 0.0542 0.041 Uiso 1 1 calc R . . H9B H 0.9817 0.2867 0.1031 0.041 Uiso 1 1 calc R . . C10 C 0.93787(18) 0.2936(3) 0.01781(18) 0.0323(9) Uani 1 1 d . . . C11 C 0.9350(2) 0.3896(3) 0.0191(2) 0.0460(12) Uani 1 1 d . . . H11 H 0.9520 0.4220 0.0539 0.055 Uiso 1 1 calc R . . C12 C 0.9077(3) 0.4398(3) -0.0294(2) 0.0525(14) Uani 1 1 d . . . C13 C 0.9047(4) 0.5449(4) -0.0279(3) 0.084(2) Uani 1 1 d . . . H13A H 0.8970 0.5683 -0.0709 0.126 Uiso 1 1 calc R . . H13B H 0.9396 0.5699 -0.0108 0.126 Uiso 1 1 calc R . . H13C H 0.8754 0.5641 -0.0012 0.126 Uiso 1 1 calc R . . C14 C 0.8814(2) 0.3904(3) -0.07818(19) 0.0422(11) Uani 1 1 d . . . H14 H 0.8616 0.4232 -0.1108 0.051 Uiso 1 1 calc R . . C15 C 0.88310(18) 0.2942(3) -0.08082(17) 0.0312(9) Uani 1 1 d . . . C16 C 0.91279(17) 0.2454(3) -0.03313(17) 0.0290(9) Uani 1 1 d . . . C17 C 0.85100(17) 0.2438(3) -0.13265(17) 0.0316(9) Uani 1 1 d . . . H17A H 0.8265 0.2885 -0.1555 0.038 Uiso 1 1 calc R . . H17B H 0.8278 0.1967 -0.1134 0.038 Uiso 1 1 calc R . . C18 C 1.04157(17) 0.2102(3) -0.10019(18) 0.0320(9) Uani 1 1 d . . . H18 H 1.0543 0.1584 -0.0760 0.038 Uiso 1 1 calc R . . C19 C 1.07308(19) 0.2895(3) -0.09973(19) 0.0370(10) Uani 1 1 d . . . H19 H 1.1074 0.2917 -0.0766 0.044 Uiso 1 1 calc R . . C20 C 1.0538(2) 0.3657(3) -0.13349(19) 0.0380(10) Uani 1 1 d . . . H20 H 1.0745 0.4213 -0.1334 0.046 Uiso 1 1 calc R . . C21 C 1.00423(19) 0.3603(3) -0.16730(18) 0.0347(9) Uani 1 1 d . . . H21 H 0.9901 0.4121 -0.1904 0.042 Uiso 1 1 calc R . . C22 C 0.97519(17) 0.2775(3) -0.16705(16) 0.0272(8) Uani 1 1 d . . . C23 C 0.92286(17) 0.2646(3) -0.20700(18) 0.0306(9) Uani 1 1 d . . . H23A H 0.9040 0.3249 -0.2118 0.037 Uiso 1 1 calc R . . H23B H 0.9318 0.2433 -0.2495 0.037 Uiso 1 1 calc R . . C24 C 0.84901(16) 0.1487(3) -0.22903(17) 0.0286(8) Uani 1 1 d . . . H24 H 0.8219 0.1118 -0.2062 0.034 Uiso 1 1 calc R . . C25 C 0.81647(18) 0.2144(3) -0.27312(19) 0.0366(10) Uani 1 1 d . . . H25A H 0.7961 0.2581 -0.2481 0.055 Uiso 1 1 calc R . . H25B H 0.7908 0.1787 -0.3007 0.055 Uiso 1 1 calc R . . H25C H 0.8416 0.2486 -0.2989 0.055 Uiso 1 1 calc R . . C26 C 0.88174(18) 0.0801(3) -0.26665(18) 0.0332(9) Uani 1 1 d . . . H26A H 0.9093 0.1136 -0.2894 0.050 Uiso 1 1 calc R . . H26B H 0.8570 0.0473 -0.2969 0.050 Uiso 1 1 calc R . . H26C H 0.8999 0.0354 -0.2377 0.050 Uiso 1 1 calc R . . C27 C 0.86221(16) -0.0521(3) -0.07418(18) 0.0299(9) Uani 1 1 d . A . C28 C 0.8317(2) -0.1397(3) -0.0952(2) 0.0478(12) Uani 1 1 d D . . C29A C 0.8014(6) -0.1846(9) -0.0450(5) 0.080(2) Uani 0.544(6) 1 d PD A 1 H29A H 0.7690 -0.1477 -0.0369 0.119 Uiso 0.544(6) 1 calc PR A 1 H29B H 0.8250 -0.1889 -0.0063 0.119 Uiso 0.544(6) 1 calc PR A 1 H29C H 0.7901 -0.2468 -0.0587 0.119 Uiso 0.544(6) 1 calc PR A 1 C30A C 0.8820(5) -0.2107(7) -0.1047(5) 0.080(2) Uani 0.544(6) 1 d PD A 1 H30A H 0.8675 -0.2721 -0.1159 0.119 Uiso 0.544(6) 1 calc PR A 1 H30B H 0.9049 -0.2148 -0.0654 0.119 Uiso 0.544(6) 1 calc PR A 1 H30C H 0.9040 -0.1880 -0.1386 0.119 Uiso 0.544(6) 1 calc PR A 1 C31A C 0.8035(5) -0.1335(8) -0.1580(5) 0.080(2) Uani 0.544(6) 1 d PD A 1 H31A H 0.8286 -0.1088 -0.1881 0.119 Uiso 0.544(6) 1 calc PR A 1 H31B H 0.7718 -0.0923 -0.1562 0.119 Uiso 0.544(6) 1 calc PR A 1 H31C H 0.7911 -0.1952 -0.1716 0.119 Uiso 0.544(6) 1 calc PR A 1 C29B C 0.8310(7) -0.2123(9) -0.0446(6) 0.080(2) Uani 0.456(6) 1 d PD A 2 H29D H 0.8091 -0.2652 -0.0601 0.119 Uiso 0.456(6) 1 calc PR A 2 H29E H 0.8151 -0.1864 -0.0072 0.119 Uiso 0.456(6) 1 calc PR A 2 H29F H 0.8685 -0.2328 -0.0336 0.119 Uiso 0.456(6) 1 calc PR A 2 C30B C 0.8518(6) -0.1762(9) -0.1547(5) 0.080(2) Uani 0.456(6) 1 d PD A 2 H30D H 0.8354 -0.2369 -0.1637 0.119 Uiso 0.456(6) 1 calc PR A 2 H30E H 0.8917 -0.1822 -0.1504 0.119 Uiso 0.456(6) 1 calc PR A 2 H30F H 0.8417 -0.1335 -0.1893 0.119 Uiso 0.456(6) 1 calc PR A 2 C31B C 0.7711(5) -0.1073(9) -0.1079(6) 0.080(2) Uani 0.456(6) 1 d PD A 2 H31D H 0.7700 -0.0548 -0.1373 0.119 Uiso 0.456(6) 1 calc PR A 2 H31E H 0.7561 -0.0883 -0.0681 0.119 Uiso 0.456(6) 1 calc PR A 2 H31F H 0.7493 -0.1584 -0.1264 0.119 Uiso 0.456(6) 1 calc PR A 2 O6 O 1.0000 0.6998(5) -0.2500 0.125(3) Uani 1 2 d S B 3 H6O H 0.9681 0.7197 -0.2586 0.188 Uiso 0.50 1 d PR B 3 H6P H 0.9971 0.6407 -0.2438 0.188 Uiso 0.50 1 d PR B 3 O8 O 0.7680(4) 0.6665(8) -0.3956(5) 0.091(3) Uani 0.50 1 d PD C 3 H8O H 0.7811 0.6094 -0.3746 0.137 Uiso 0.50 1 d PRD C 3 C33 C 0.7633(6) 0.6509(7) -0.4632(6) 0.097(5) Uani 0.50 1 d PDU C 3 H33A H 0.7336 0.6061 -0.4737 0.116 Uiso 0.50 1 calc PR C 3 H33B H 0.7979 0.6247 -0.4773 0.116 Uiso 0.50 1 calc PR C 3 C34 C 0.7500 0.7500 -0.5000 0.143(6) Uani 1 2 d SD C 3 H34A H 0.7269 0.7884 -0.4744 0.215 Uiso 0.50 1 calc PR C 3 H34B H 0.7309 0.7377 -0.5410 0.215 Uiso 0.50 1 calc PR C 3 H34C H 0.7843 0.7826 -0.5064 0.215 Uiso 0.50 1 calc PR C 3 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 0.0359(3) 0.0237(2) 0.0176(2) -0.00143(16) -0.00165(17) 0.00507(19) Zn2 0.0324(3) 0.0208(2) 0.0183(2) -0.00047(16) -0.00105(17) 0.00280(18) P1 0.0926(12) 0.0486(8) 0.0521(8) 0.0240(6) 0.0295(8) 0.0318(8) F1 0.221(5) 0.0435(19) 0.064(2) 0.0200(17) 0.065(3) 0.032(3) F2 0.207(5) 0.057(2) 0.061(2) 0.0138(17) 0.065(3) 0.034(3) F3 0.073(2) 0.062(2) 0.096(3) 0.0168(19) 0.025(2) 0.0074(18) F4 0.097(3) 0.099(3) 0.0500(19) 0.0328(18) 0.0175(18) -0.001(2) F5 0.069(2) 0.069(2) 0.140(4) 0.011(2) 0.018(2) 0.011(2) F6 0.140(4) 0.150(4) 0.077(3) -0.009(3) -0.009(3) 0.106(4) O1 0.0380(15) 0.0238(14) 0.0213(13) -0.0031(10) -0.0023(11) 0.0065(11) O2 0.0426(16) 0.0214(14) 0.0201(13) -0.0014(10) 0.0002(11) 0.0061(12) O3 0.0459(17) 0.0302(16) 0.0219(13) -0.0008(11) -0.0059(12) -0.0015(13) O4 0.0496(18) 0.0352(17) 0.0243(14) 0.0011(12) -0.0025(12) -0.0093(14) O5 0.0400(16) 0.0271(15) 0.0300(14) -0.0044(12) -0.0093(12) 0.0088(12) N1 0.038(2) 0.038(2) 0.0233(16) 0.0020(14) -0.0005(14) 0.0104(16) N2 0.041(2) 0.0255(17) 0.0199(15) -0.0019(13) -0.0022(13) 0.0106(15) N3 0.0337(18) 0.0253(17) 0.0222(15) -0.0015(13) -0.0024(13) 0.0002(14) N4 0.0334(18) 0.0247(17) 0.0187(15) -0.0020(12) -0.0005(13) 0.0048(14) C1 0.036(2) 0.044(3) 0.031(2) 0.0044(19) -0.0011(18) 0.008(2) C2 0.040(3) 0.053(3) 0.042(3) 0.014(2) 0.004(2) 0.011(2) C3 0.048(3) 0.063(3) 0.038(3) 0.012(2) 0.011(2) 0.028(3) C4 0.053(3) 0.050(3) 0.030(2) 0.006(2) 0.005(2) 0.026(2) C5 0.044(2) 0.038(2) 0.0217(19) 0.0035(17) 0.0004(17) 0.023(2) C6 0.051(3) 0.033(2) 0.025(2) -0.0036(17) -0.0001(18) 0.019(2) C7 0.044(2) 0.029(2) 0.0190(18) -0.0024(15) -0.0039(16) 0.0115(18) C8 0.033(2) 0.023(2) 0.0262(19) 0.0018(15) 0.0020(16) 0.0018(16) C9 0.049(3) 0.026(2) 0.027(2) -0.0050(16) -0.0059(18) 0.0033(19) C10 0.051(3) 0.023(2) 0.0226(19) 0.0006(15) -0.0028(17) 0.0066(18) C11 0.081(4) 0.028(2) 0.028(2) -0.0073(17) -0.012(2) 0.007(2) C12 0.097(4) 0.025(2) 0.034(2) -0.0042(19) -0.007(3) 0.015(3) C13 0.170(7) 0.027(3) 0.050(3) -0.005(2) -0.036(4) 0.018(4) C14 0.069(3) 0.032(2) 0.025(2) -0.0026(17) -0.008(2) 0.018(2) C15 0.045(2) 0.028(2) 0.0204(18) -0.0029(15) 0.0001(16) 0.0112(18) C16 0.041(2) 0.024(2) 0.0226(18) -0.0022(15) 0.0023(16) 0.0080(17) C17 0.038(2) 0.034(2) 0.0225(19) -0.0036(16) -0.0018(16) 0.0126(18) C18 0.037(2) 0.030(2) 0.029(2) -0.0028(16) -0.0039(17) -0.0001(18) C19 0.042(2) 0.038(2) 0.031(2) -0.0078(18) -0.0010(18) -0.0084(19) C20 0.055(3) 0.028(2) 0.031(2) -0.0058(18) 0.0029(19) -0.015(2) C21 0.057(3) 0.026(2) 0.0211(19) 0.0008(16) 0.0024(18) -0.001(2) C22 0.039(2) 0.0233(19) 0.0192(17) -0.0008(14) -0.0002(15) 0.0003(17) C23 0.044(2) 0.024(2) 0.0237(19) 0.0026(15) -0.0032(16) 0.0015(18) C24 0.033(2) 0.031(2) 0.0209(18) -0.0014(15) -0.0060(15) 0.0030(17) C25 0.038(2) 0.041(3) 0.029(2) -0.0032(18) -0.0112(17) 0.011(2) C26 0.040(2) 0.035(2) 0.0239(19) -0.0065(16) -0.0053(17) 0.0033(18) C27 0.033(2) 0.031(2) 0.026(2) -0.0019(16) 0.0007(16) -0.0006(17) C28 0.067(3) 0.043(3) 0.032(2) 0.000(2) -0.009(2) -0.023(2) C29A 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) C30A 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) C31A 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) C29B 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) C30B 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) C31B 0.118(6) 0.059(4) 0.060(3) 0.000(3) -0.011(3) -0.047(4) O6 0.164(8) 0.048(4) 0.156(8) 0.000 -0.055(6) 0.000 O8 0.074(6) 0.104(8) 0.093(7) 0.003(6) -0.020(5) -0.006(6) C33 0.065(7) 0.139(10) 0.088(8) -0.073(8) 0.017(6) -0.030(7) C34 0.126(11) 0.25(2) 0.051(6) 0.005(9) 0.019(7) 0.005(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 Zn1 O2 1.956(3) . yes Zn1 O3 2.006(3) . yes Zn1 O1 2.022(3) . yes Zn1 N1 2.087(3) . yes Zn1 N2 2.221(3) . yes Zn2 O5 1.990(3) . yes Zn2 O2 2.004(2) . yes Zn2 O4 2.069(3) . yes Zn2 N4 2.102(3) . yes Zn2 N3 2.147(3) . yes P1 F6 1.574(5) . ? P1 F5 1.580(4) . ? P1 F4 1.583(3) . ? P1 F2 1.587(4) . ? P1 F1 1.590(4) . ? P1 F3 1.593(4) . ? O1 C8 1.265(5) . ? O2 C16 1.355(5) . ? O3 C27 1.265(5) . ? O4 C27 1.250(5) . ? O5 C8 1.247(5) 5_755 ? N1 C1 1.336(6) . ? N1 C5 1.349(5) . ? N2 C7 1.468(5) . ? N2 C6 1.471(5) . ? N2 C9 1.489(5) . ? N3 C22 1.342(5) . ? N3 C18 1.346(5) . ? N4 C23 1.486(5) . ? N4 C17 1.504(5) . ? N4 C24 1.508(5) . ? C1 C2 1.383(6) . ? C1 H1 0.9500 . ? C2 C3 1.387(7) . ? C2 H2 0.9500 . ? C3 C4 1.378(8) . ? C3 H3 0.9500 . ? C4 C5 1.386(6) . ? C4 H4 0.9500 . ? C5 C6 1.499(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O5 1.247(5) 5_755 ? C9 C10 1.503(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.390(6) . ? C10 C16 1.398(5) . ? C11 C12 1.397(6) . ? C11 H11 0.9500 . ? C12 C14 1.386(6) . ? C12 C13 1.521(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.391(6) . ? C14 H14 0.9500 . ? C15 C16 1.402(5) . ? C15 C17 1.503(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.382(6) . ? C18 H18 0.9500 . ? C19 C20 1.381(6) . ? C19 H19 0.9500 . ? C20 C21 1.377(6) . ? C20 H20 0.9500 . ? C21 C22 1.391(6) . ? C21 H21 0.9500 . ? C22 C23 1.508(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.525(5) . ? C24 C26 1.529(5) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.524(6) . ? C28 C31A 1.469(10) . ? C28 C30B 1.479(12) . ? C28 C29A 1.482(11) . ? C28 C29B 1.501(12) . ? C28 C31B 1.565(12) . ? C28 C30A 1.626(12) . ? C29A H29A 0.9800 . ? C29A H29B 0.9800 . ? C29A H29C 0.9800 . ? C30A H30A 0.9800 . ? C30A H30B 0.9800 . ? C30A H30C 0.9800 . ? C31A H31A 0.9800 . ? C31A H31B 0.9800 . ? C31A H31C 0.9800 . ? C29B H29D 0.9800 . ? C29B H29E 0.9800 . ? C29B H29F 0.9800 . ? C30B H30D 0.9800 . ? C30B H30E 0.9800 . ? C30B H30F 0.9800 . ? C31B H31D 0.9800 . ? C31B H31E 0.9800 . ? C31B H31F 0.9800 . ? O6 H6O 0.8438 . ? O6 H6P 0.8676 . ? O8 C33 1.452(15) . ? O8 H8O 0.9813 . ? C33 C34 1.654(11) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O3 100.99(11) . . yes O2 Zn1 O1 117.80(11) . . yes O3 Zn1 O1 96.32(11) . . ? O2 Zn1 N1 122.24(12) . . ? O3 Zn1 N1 94.94(13) . . ? O1 Zn1 N1 114.95(12) . . ? O2 Zn1 N2 89.96(11) . . ? O3 Zn1 N2 168.96(11) . . ? O1 Zn1 N2 79.55(11) . . ? N1 Zn1 N2 77.81(13) . . yes O5 Zn2 O2 138.36(11) . . yes O5 Zn2 O4 86.17(12) . . ? O2 Zn2 O4 89.11(11) . . yes O5 Zn2 N4 122.30(11) . . ? O2 Zn2 N4 99.32(11) . . ? O4 Zn2 N4 94.95(12) . . ? O5 Zn2 N3 97.04(12) . . ? O2 Zn2 N3 90.08(11) . . ? O4 Zn2 N3 175.98(12) . . ? N4 Zn2 N3 81.30(12) . . yes F6 P1 F5 178.9(3) . . ? F6 P1 F4 89.2(2) . . ? F5 P1 F4 91.2(2) . . ? F6 P1 F2 90.8(3) . . ? F5 P1 F2 88.8(3) . . ? F4 P1 F2 179.3(3) . . ? F6 P1 F1 90.9(3) . . ? F5 P1 F1 90.2(3) . . ? F4 P1 F1 88.5(2) . . ? F2 P1 F1 90.8(2) . . ? F6 P1 F3 89.9(3) . . ? F5 P1 F3 89.0(2) . . ? F4 P1 F3 90.8(2) . . ? F2 P1 F3 89.9(2) . . ? F1 P1 F3 179.0(3) . . ? C8 O1 Zn1 116.3(2) . . ? C16 O2 Zn1 125.3(2) . . ? C16 O2 Zn2 116.6(2) . . ? Zn1 O2 Zn2 118.02(13) . . yes C27 O3 Zn1 128.0(3) . . ? C27 O4 Zn2 128.3(3) . . ? C8 O5 Zn2 115.7(2) 5_755 . ? C1 N1 C5 119.4(4) . . ? C1 N1 Zn1 124.0(3) . . ? C5 N1 Zn1 116.4(3) . . ? C7 N2 C6 111.0(3) . . ? C7 N2 C9 110.6(3) . . ? C6 N2 C9 113.4(3) . . ? C7 N2 Zn1 104.4(2) . . ? C6 N2 Zn1 107.7(3) . . ? C9 N2 Zn1 109.2(2) . . ? C22 N3 C18 118.6(3) . . ? C22 N3 Zn2 112.6(3) . . ? C18 N3 Zn2 126.9(3) . . ? C23 N4 C17 110.1(3) . . ? C23 N4 C24 112.5(3) . . ? C17 N4 C24 109.7(3) . . ? C23 N4 Zn2 109.6(2) . . ? C17 N4 Zn2 102.8(2) . . ? C24 N4 Zn2 111.7(2) . . ? N1 C1 C2 122.2(4) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 118.6(5) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.1(5) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.3(5) . . ? N1 C5 C6 117.1(4) . . ? C4 C5 C6 121.6(4) . . ? N2 C6 C5 110.0(3) . . ? N2 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N2 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N2 C7 C8 111.3(3) . . ? N2 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N2 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O5 C8 O1 124.2(4) 5_755 . ? O5 C8 C7 116.3(3) 5_755 . ? O1 C8 C7 119.4(3) . . ? N2 C9 C10 112.5(3) . . ? N2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C16 119.4(4) . . ? C11 C10 C9 120.3(4) . . ? C16 C10 C9 120.3(3) . . ? C10 C11 C12 121.7(4) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C14 C12 C11 117.8(4) . . ? C14 C12 C13 120.5(4) . . ? C11 C12 C13 121.7(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15 122.0(4) . . ? C12 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 C17 119.8(4) . . ? C16 C15 C17 120.8(4) . . ? O2 C16 C10 121.1(3) . . ? O2 C16 C15 119.2(3) . . ? C10 C16 C15 119.7(4) . . ? C15 C17 N4 114.4(3) . . ? C15 C17 H17A 108.7 . . ? N4 C17 H17A 108.7 . . ? C15 C17 H17B 108.7 . . ? N4 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? N3 C18 C19 122.3(4) . . ? N3 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C20 C19 C18 118.9(4) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? C21 C20 C19 119.3(4) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 118.9(4) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? N3 C22 C21 122.0(4) . . ? N3 C22 C23 116.3(3) . . ? C21 C22 C23 121.6(4) . . ? N4 C23 C22 112.7(3) . . ? N4 C23 H23A 109.1 . . ? C22 C23 H23A 109.1 . . ? N4 C23 H23B 109.1 . . ? C22 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? N4 C24 C25 114.2(3) . . ? N4 C24 C26 110.8(3) . . ? C25 C24 C26 110.8(3) . . ? N4 C24 H24 106.9 . . ? C25 C24 H24 106.9 . . ? C26 C24 H24 106.9 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O4 C27 O3 124.7(4) . . ? O4 C27 C28 117.3(3) . . ? O3 C27 C28 118.0(4) . . ? C31A C28 C30B 53.8(7) . . ? C31A C28 C29A 116.7(7) . . ? C30B C28 C29A 131.6(8) . . ? C31A C28 C29B 131.9(8) . . ? C30B C28 C29B 112.3(8) . . ? C31A C28 C27 114.4(5) . . ? C30B C28 C27 111.3(6) . . ? C29A C28 C27 114.3(6) . . ? C29B C28 C27 113.3(6) . . ? C31A C28 C31B 55.4(7) . . ? C30B C28 C31B 108.6(7) . . ? C29A C28 C31B 75.3(7) . . ? C29B C28 C31B 106.5(8) . . ? C27 C28 C31B 104.3(6) . . ? C31A C28 C30A 104.3(7) . . ? C30B C28 C30A 51.4(7) . . ? C29A C28 C30A 103.2(7) . . ? C29B C28 C30A 71.8(8) . . ? C27 C28 C30A 101.4(5) . . ? C31B C28 C30A 152.4(7) . . ? C28 C29A H29A 109.5 . . ? C28 C29A H29B 109.5 . . ? C28 C29A H29C 109.5 . . ? C28 C30A H30A 109.5 . . ? C28 C30A H30B 109.5 . . ? C28 C30A H30C 109.5 . . ? C28 C31A H31A 109.5 . . ? C28 C31A H31B 109.5 . . ? C28 C31A H31C 109.5 . . ? C28 C29B H29D 109.5 . . ? C28 C29B H29E 109.5 . . ? H29D C29B H29E 109.5 . . ? C28 C29B H29F 109.5 . . ? H29D C29B H29F 109.5 . . ? H29E C29B H29F 109.5 . . ? C28 C30B H30D 109.5 . . ? C28 C30B H30E 109.5 . . ? H30D C30B H30E 109.5 . . ? C28 C30B H30F 109.5 . . ? H30D C30B H30F 109.5 . . ? H30E C30B H30F 109.5 . . ? C28 C31B H31D 109.5 . . ? C28 C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C28 C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? H6O O6 H6P 106.7 . . ? C33 O8 H8O 108.9 . . ? O8 C33 C34 109.6(8) . . ? O8 C33 H33A 109.8 . . ? C34 C33 H33A 109.8 . . ? O8 C33 H33B 109.8 . . ? C34 C33 H33B 109.8 . . ? H33A C33 H33B 108.2 . . ? 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 _geom_hbond_publ_flag O6 H6O F1 0.84 2.35 3.006(6) 135.0 . yes O6 H6P F5 0.87 2.50 3.190(7) 136.8 . yes O6 H6P F5 0.87 2.62 3.190(7) 124.1 2_754 yes O8 H8O F6 0.98 2.18 2.884(11) 127.6 . yes O8 H8O F2 0.98 2.43 3.157(11) 130.7 . yes _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.056 _refine_diff_density_min -0.761 _refine_diff_density_rms 0.087 # Attachment 'Structure 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 667079' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H66 N8 O10 Zn4, 2(F6 P)' _chemical_formula_sum 'C56 H66 F12 N8 O10 P2 Zn4' _chemical_formula_weight 1562.59 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' F F 0.0171 0.0103 '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' 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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.5983(2) _cell_length_b 19.4790(3) _cell_length_c 12.5532(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.187(2) _cell_angle_gamma 90.00 _cell_volume 3056.38(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 53314 _cell_measurement_theta_min 3.47 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 1.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5744 _exptl_absorpt_correction_T_max 0.7464 _exptl_absorpt_process_details 'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.99 \%A from atom F3 and the deepest hole is located 0.53 \%A from atom P1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53314 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6951 _reflns_number_gt 6188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1e (Brandenburg, 2007)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0451P)^2^+4.4968P] 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 6951 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0897 _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 0.52792(2) -0.020950(13) 0.19526(2) 0.02108(8) Uani 1 1 d . . . Zn2 Zn 0.34452(2) -0.121962(13) -0.12111(2) 0.02138(8) Uani 1 1 d . . . O1 O 0.46610(13) -0.07293(9) 0.06062(13) 0.0252(3) Uani 1 1 d . . . O2 O 0.66244(12) 0.03091(8) 0.19945(13) 0.0223(3) Uani 1 1 d . . . O3 O 0.42185(14) 0.05467(9) 0.17157(15) 0.0299(4) Uani 1 1 d . . . O4 O 0.52252(14) 0.14924(9) 0.19376(14) 0.0291(4) Uani 1 1 d . . . O5 O 0.41709(14) -0.17759(9) 0.00678(13) 0.0286(4) Uani 1 1 d . . . N1 N 0.47565(16) -0.05506(11) 0.33971(16) 0.0246(4) Uani 1 1 d . . . N2 N 0.61222(16) -0.11793(10) 0.22285(15) 0.0217(4) Uani 1 1 d . . . N3 N 0.77901(16) 0.17339(10) 0.21934(16) 0.0234(4) Uani 1 1 d . . . N4 N 0.78556(16) 0.09343(11) 0.03970(15) 0.0248(4) Uani 1 1 d . . . C1 C 0.3939(2) -0.02791(14) 0.3856(2) 0.0294(5) Uani 1 1 d . . . H1 H 0.3507 0.0065 0.3481 0.035 Uiso 1 1 calc R . . C2 C 0.3710(2) -0.04860(15) 0.4856(2) 0.0336(6) Uani 1 1 d . . . H2 H 0.3124 -0.0293 0.5161 0.040 Uiso 1 1 calc R . . C3 C 0.4351(2) -0.09799(17) 0.5402(2) 0.0370(6) Uani 1 1 d . . . H3 H 0.4225 -0.1118 0.6101 0.044 Uiso 1 1 calc R . . C4 C 0.5175(2) -0.12733(14) 0.4931(2) 0.0311(5) Uani 1 1 d . . . H4 H 0.5607 -0.1624 0.5289 0.037 Uiso 1 1 calc R . . C5 C 0.53584(19) -0.10435(13) 0.39200(18) 0.0250(5) Uani 1 1 d . . . C6 C 0.62835(19) -0.13176(12) 0.33897(18) 0.0239(5) Uani 1 1 d . . . H6A H 0.6956 -0.1098 0.3714 0.029 Uiso 1 1 calc R . . H6B H 0.6349 -0.1819 0.3513 0.029 Uiso 1 1 calc R . . C7 C 0.54041(19) -0.16913(12) 0.16486(19) 0.0243(5) Uani 1 1 d . . . H7A H 0.4947 -0.1897 0.2150 0.029 Uiso 1 1 calc R . . H7B H 0.5838 -0.2063 0.1383 0.029 Uiso 1 1 calc R . . C8 C 0.46981(19) -0.13737(13) 0.07057(18) 0.0241(5) Uani 1 1 d . . . C9 C 0.71406(19) -0.11305(12) 0.17498(19) 0.0244(5) Uani 1 1 d . . . H9A H 0.6979 -0.1001 0.0984 0.029 Uiso 1 1 calc R . . H9B H 0.7489 -0.1587 0.1783 0.029 Uiso 1 1 calc R . . C10 C 0.79021(18) -0.06151(12) 0.23106(18) 0.0223(4) Uani 1 1 d . . . C11 C 0.89186(19) -0.08290(13) 0.27626(18) 0.0244(5) Uani 1 1 d . . . H11 H 0.9102 -0.1301 0.2723 0.029 Uiso 1 1 calc R . . C12 C 0.96706(18) -0.03733(14) 0.32686(18) 0.0255(5) Uani 1 1 d . . . C13 C 1.0765(2) -0.06155(14) 0.3749(2) 0.0309(5) Uani 1 1 d . . . H13A H 1.1129 -0.0246 0.4182 0.046 Uiso 1 1 calc R . . H13B H 1.1185 -0.0741 0.3173 0.046 Uiso 1 1 calc R . . H13C H 1.0690 -0.1016 0.4206 0.046 Uiso 1 1 calc R . . C14 C 0.93736(19) 0.03099(13) 0.33362(18) 0.0250(5) Uani 1 1 d . . . H14 H 0.9879 0.0629 0.3672 0.030 Uiso 1 1 calc R . . C15 C 0.83535(18) 0.05435(12) 0.29253(17) 0.0224(4) Uani 1 1 d . . . C16 C 0.76122(18) 0.00800(12) 0.23989(17) 0.0218(4) Uani 1 1 d . . . C17 C 0.8040(2) 0.12718(12) 0.31505(19) 0.0248(5) Uani 1 1 d . . . H17A H 0.7404 0.1257 0.3540 0.030 Uiso 1 1 calc R . . H17B H 0.8629 0.1482 0.3638 0.030 Uiso 1 1 calc R . . C18 C 0.7434(2) 0.24255(13) 0.2579(2) 0.0302(5) Uani 1 1 d . . . H18 H 0.6841 0.2334 0.3021 0.036 Uiso 1 1 calc R . . C19 C 0.8300(3) 0.28094(15) 0.3293(3) 0.0430(7) Uani 1 1 d . . . H19A H 0.8548 0.2528 0.3922 0.064 Uiso 1 1 calc R . . H19B H 0.8009 0.3243 0.3528 0.064 Uiso 1 1 calc R . . H19C H 0.8901 0.2905 0.2890 0.064 Uiso 1 1 calc R . . C20 C 0.6973(2) 0.28716(14) 0.1645(2) 0.0376(6) Uani 1 1 d . . . H20A H 0.7524 0.2960 0.1176 0.056 Uiso 1 1 calc R . . H20B H 0.6731 0.3308 0.1918 0.056 Uiso 1 1 calc R . . H20C H 0.6366 0.2635 0.1237 0.056 Uiso 1 1 calc R . . C21 C 0.8746(2) 0.17908(13) 0.1617(2) 0.0293(5) Uani 1 1 d . . . H21A H 0.9397 0.1737 0.2139 0.035 Uiso 1 1 calc R . . H21B H 0.8763 0.2255 0.1300 0.035 Uiso 1 1 calc R . . C22 C 0.8763(2) 0.12656(13) 0.0741(2) 0.0279(5) Uani 1 1 d . . . C23 C 0.9696(2) 0.11632(16) 0.0270(2) 0.0374(6) Uani 1 1 d . . . H23 H 1.0335 0.1403 0.0522 0.045 Uiso 1 1 calc R . . C24 C 0.9670(2) 0.07055(18) -0.0568(2) 0.0443(7) Uani 1 1 d . . . H24 H 1.0290 0.0633 -0.0912 0.053 Uiso 1 1 calc R . . C25 C 0.8733(3) 0.03492(17) -0.0910(2) 0.0405(7) Uani 1 1 d . . . H25 H 0.8708 0.0028 -0.1481 0.049 Uiso 1 1 calc R . . C26 C 0.7842(2) 0.04712(14) -0.0404(2) 0.0309(5) Uani 1 1 d . . . H26 H 0.7203 0.0223 -0.0625 0.037 Uiso 1 1 calc R . . C27 C 0.4339(2) 0.11858(13) 0.1817(2) 0.0275(5) Uani 1 1 d . . . C28 C 0.3331(2) 0.16035(16) 0.1781(3) 0.0516(9) Uani 1 1 d . . . H28A H 0.3389 0.1916 0.2397 0.077 Uiso 1 1 calc R . . H28B H 0.2719 0.1296 0.1809 0.077 Uiso 1 1 calc R . . H28C H 0.3228 0.1870 0.1114 0.077 Uiso 1 1 calc R . . P1 P 0.14639(6) 0.20256(4) 0.44130(7) 0.04103(19) Uani 1 1 d . . . F1 F 0.18255(17) 0.12460(9) 0.46504(17) 0.0550(5) Uani 1 1 d . . . F2 F 0.26676(14) 0.22069(10) 0.42447(19) 0.0564(5) Uani 1 1 d . . . F3 F 0.11865(18) 0.18395(16) 0.31755(18) 0.0772(7) Uani 1 1 d . . . F4 F 0.02697(15) 0.18412(11) 0.46027(18) 0.0590(6) Uani 1 1 d . . . F5 F 0.17300(16) 0.22052(11) 0.56596(18) 0.0571(5) Uani 1 1 d . . . F6 F 0.11177(17) 0.28017(11) 0.4157(2) 0.0731(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01886(14) 0.02272(14) 0.02113(14) 0.00106(9) 0.00042(10) 0.00210(9) Zn2 0.01996(14) 0.02373(14) 0.01959(13) 0.00090(10) -0.00091(10) 0.00124(9) O1 0.0259(8) 0.0268(8) 0.0214(8) 0.0030(6) -0.0026(6) 0.0027(6) O2 0.0179(7) 0.0250(8) 0.0232(8) 0.0033(6) -0.0008(6) 0.0022(6) O3 0.0240(8) 0.0278(9) 0.0369(10) 0.0004(7) -0.0004(7) 0.0056(7) O4 0.0252(9) 0.0273(9) 0.0352(9) -0.0005(7) 0.0056(7) 0.0027(7) O5 0.0305(9) 0.0286(9) 0.0238(8) -0.0027(7) -0.0078(7) 0.0040(7) N1 0.0220(9) 0.0288(10) 0.0230(9) -0.0019(8) 0.0022(7) -0.0014(8) N2 0.0216(9) 0.0250(10) 0.0178(9) 0.0006(7) -0.0009(7) 0.0015(7) N3 0.0232(9) 0.0240(10) 0.0222(9) -0.0007(7) -0.0008(7) 0.0013(7) N4 0.0246(10) 0.0296(10) 0.0199(9) 0.0046(8) 0.0015(7) 0.0036(8) C1 0.0241(12) 0.0339(13) 0.0302(12) -0.0045(10) 0.0041(10) -0.0003(10) C2 0.0245(12) 0.0485(16) 0.0287(13) -0.0100(11) 0.0067(10) -0.0075(11) C3 0.0313(14) 0.0569(18) 0.0231(12) -0.0013(12) 0.0047(10) -0.0129(12) C4 0.0273(12) 0.0420(14) 0.0228(11) 0.0033(10) -0.0019(9) -0.0050(10) C5 0.0226(11) 0.0307(12) 0.0207(11) -0.0012(9) -0.0012(9) -0.0051(9) C6 0.0236(11) 0.0275(11) 0.0195(10) 0.0032(9) -0.0010(9) 0.0020(9) C7 0.0257(11) 0.0231(11) 0.0228(11) 0.0009(9) -0.0024(9) 0.0025(9) C8 0.0220(11) 0.0301(12) 0.0200(10) 0.0001(9) 0.0019(9) 0.0032(9) C9 0.0225(11) 0.0281(12) 0.0226(11) -0.0021(9) 0.0034(9) 0.0057(9) C10 0.0205(11) 0.0288(12) 0.0178(10) 0.0020(9) 0.0027(8) 0.0027(9) C11 0.0236(11) 0.0292(12) 0.0209(10) 0.0021(9) 0.0046(9) 0.0060(9) C12 0.0204(11) 0.0371(13) 0.0191(10) 0.0036(9) 0.0026(8) 0.0045(9) C13 0.0219(11) 0.0405(14) 0.0292(12) 0.0034(11) -0.0006(10) 0.0068(10) C14 0.0224(11) 0.0341(12) 0.0180(10) 0.0008(9) 0.0009(8) 0.0008(9) C15 0.0224(11) 0.0276(11) 0.0172(10) 0.0017(8) 0.0025(8) 0.0014(9) C16 0.0185(10) 0.0299(12) 0.0168(10) 0.0039(9) 0.0019(8) 0.0037(9) C17 0.0253(11) 0.0284(12) 0.0197(10) -0.0012(9) -0.0012(9) 0.0016(9) C18 0.0299(12) 0.0260(12) 0.0329(13) -0.0054(10) -0.0037(10) 0.0038(10) C19 0.0434(16) 0.0332(14) 0.0470(17) -0.0123(12) -0.0156(13) 0.0058(12) C20 0.0402(15) 0.0260(13) 0.0430(15) -0.0019(11) -0.0092(12) 0.0039(11) C21 0.0245(12) 0.0321(13) 0.0303(12) 0.0047(10) -0.0004(10) -0.0023(9) C22 0.0250(12) 0.0345(13) 0.0246(11) 0.0096(10) 0.0038(9) 0.0029(10) C23 0.0276(13) 0.0523(17) 0.0329(14) 0.0098(12) 0.0065(11) 0.0054(12) C24 0.0377(16) 0.062(2) 0.0364(15) 0.0113(14) 0.0175(12) 0.0169(14) C25 0.0464(17) 0.0505(17) 0.0256(13) 0.0023(12) 0.0079(12) 0.0178(14) C26 0.0366(14) 0.0329(13) 0.0227(11) 0.0035(10) 0.0018(10) 0.0071(11) C27 0.0246(12) 0.0320(13) 0.0257(11) 0.0008(10) 0.0022(9) 0.0050(9) C28 0.0285(14) 0.0335(15) 0.092(3) -0.0119(16) 0.0049(16) 0.0055(12) P1 0.0274(3) 0.0399(4) 0.0530(5) 0.0148(3) -0.0059(3) -0.0038(3) F1 0.0652(13) 0.0363(10) 0.0569(12) 0.0059(8) -0.0186(10) -0.0062(8) F2 0.0298(9) 0.0495(11) 0.0896(16) 0.0121(10) 0.0060(9) 0.0018(8) F3 0.0525(13) 0.130(2) 0.0452(11) 0.0241(13) -0.0106(10) 0.0083(13) F4 0.0355(10) 0.0713(13) 0.0662(13) 0.0241(11) -0.0095(9) -0.0191(9) F5 0.0432(10) 0.0576(12) 0.0676(13) -0.0132(10) -0.0051(9) -0.0021(9) F6 0.0459(11) 0.0525(12) 0.126(2) 0.0427(13) 0.0308(13) 0.0147(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.9680(16) . yes Zn1 O3 1.9860(17) . yes Zn1 O1 2.0394(17) . yes Zn1 N1 2.112(2) . yes Zn1 N2 2.1736(19) . yes Zn2 O2 2.0246(16) 3_655 yes Zn2 O5 2.0543(17) . yes Zn2 O4 2.0741(17) 3_655 yes Zn2 N4 2.111(2) 3_655 yes Zn2 N3 2.1132(19) 3_655 yes O1 C8 1.262(3) . yes O2 C16 1.359(3) . ? O2 Zn2 2.0246(16) 3_655 ? O3 C27 1.259(3) . ? O4 C27 1.259(3) . ? O4 Zn2 2.0741(17) 3_655 ? O5 C8 1.250(3) . yes N1 C5 1.343(3) . ? N1 C1 1.350(3) . ? N2 C6 1.471(3) . ? N2 C7 1.476(3) . ? N2 C9 1.486(3) . ? N3 C21 1.484(3) . ? N3 C17 1.503(3) . ? N3 C18 1.518(3) . ? N3 Zn2 2.1132(19) 3_655 ? N4 C22 1.336(3) . ? N4 C26 1.350(3) . ? N4 Zn2 2.112(2) 3_655 ? C1 C2 1.383(4) . ? C1 H1 0.9500 . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(3) . ? C4 H4 0.9500 . ? C5 C6 1.510(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.520(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 C10 1.502(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.398(3) . ? C10 C16 1.410(3) . ? C11 C12 1.392(3) . ? C11 H11 0.9500 . ? C12 C14 1.388(4) . ? C12 C13 1.509(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.400(3) . ? C14 H14 0.9500 . ? C15 C16 1.403(3) . ? C15 C17 1.509(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C20 1.515(4) . ? C18 C19 1.520(4) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.504(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.395(4) . ? C23 C24 1.376(5) . ? C23 H23 0.9500 . ? C24 C25 1.389(5) . ? C24 H24 0.9500 . ? C25 C26 1.378(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.503(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? P1 F3 1.591(2) . ? P1 F4 1.593(2) . ? P1 F6 1.595(2) . ? P1 F2 1.5966(19) . ? P1 F5 1.598(2) . ? P1 F1 1.603(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 O2 Zn1 O3 100.63(7) . . yes O2 Zn1 O1 121.01(7) . . ? O3 Zn1 O1 93.67(7) . . yes O2 Zn1 N1 119.90(7) . . ? O3 Zn1 N1 94.92(8) . . ? O1 Zn1 N1 115.31(7) . . ? O2 Zn1 N2 92.28(7) . . ? O3 Zn1 N2 167.07(8) . . ? O1 Zn1 N2 80.15(7) . . ? N1 Zn1 N2 77.78(8) . . yes O2 Zn2 O5 146.06(7) 3_655 . ? O2 Zn2 O4 89.96(7) 3_655 3_655 yes O5 Zn2 O4 84.47(7) . 3_655 ? O2 Zn2 N4 90.88(7) 3_655 3_655 ? O5 Zn2 N4 93.27(7) . 3_655 ? O4 Zn2 N4 177.04(7) 3_655 3_655 ? O2 Zn2 N3 98.50(7) 3_655 3_655 ? O5 Zn2 N3 115.42(7) . 3_655 ? O4 Zn2 N3 101.44(7) 3_655 3_655 ? N4 Zn2 N3 81.24(8) 3_655 3_655 yes C8 O1 Zn1 113.97(14) . . ? C16 O2 Zn1 125.92(14) . . ? C16 O2 Zn2 116.81(14) . 3_655 ? Zn1 O2 Zn2 116.86(8) . 3_655 yes C27 O3 Zn1 130.41(16) . . ? C27 O4 Zn2 125.39(16) . 3_655 ? C8 O5 Zn2 108.60(15) . . ? C5 N1 C1 119.1(2) . . ? C5 N1 Zn1 115.27(16) . . ? C1 N1 Zn1 125.45(17) . . ? C6 N2 C7 111.41(18) . . ? C6 N2 C9 113.14(18) . . ? C7 N2 C9 110.53(18) . . ? C6 N2 Zn1 108.74(14) . . ? C7 N2 Zn1 104.57(13) . . ? C9 N2 Zn1 108.02(14) . . ? C21 N3 C17 109.48(18) . . ? C21 N3 C18 112.29(19) . . ? C17 N3 C18 108.50(18) . . ? C21 N3 Zn2 109.50(14) . 3_655 ? C17 N3 Zn2 104.34(14) . 3_655 ? C18 N3 Zn2 112.39(14) . 3_655 ? C22 N4 C26 119.6(2) . . ? C22 N4 Zn2 113.61(17) . 3_655 ? C26 N4 Zn2 126.76(18) . 3_655 ? N1 C1 C2 122.0(3) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 121.8(2) . . ? N1 C5 C6 117.2(2) . . ? C4 C5 C6 120.9(2) . . ? N2 C6 C5 110.69(19) . . ? N2 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 111.83(19) . . ? N2 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N2 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? O5 C8 O1 123.4(2) . . ? O5 C8 C7 117.1(2) . . ? O1 C8 C7 119.5(2) . . ? N2 C9 C10 112.73(18) . . ? N2 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C16 119.2(2) . . ? C11 C10 C9 119.4(2) . . ? C16 C10 C9 121.5(2) . . ? C12 C11 C10 122.1(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C14 C12 C11 117.8(2) . . ? C14 C12 C13 121.0(2) . . ? C11 C12 C13 121.2(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15 122.1(2) . . ? C12 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 119.4(2) . . ? C14 C15 C17 119.1(2) . . ? C16 C15 C17 121.2(2) . . ? O2 C16 C15 119.3(2) . . ? O2 C16 C10 121.3(2) . . ? C15 C16 C10 119.4(2) . . ? N3 C17 C15 116.54(19) . . ? N3 C17 H17A 108.2 . . ? C15 C17 H17A 108.2 . . ? N3 C17 H17B 108.2 . . ? C15 C17 H17B 108.2 . . ? H17A C17 H17B 107.3 . . ? C20 C18 N3 111.2(2) . . ? C20 C18 C19 110.6(2) . . ? N3 C18 C19 113.9(2) . . ? C20 C18 H18 106.9 . . ? N3 C18 H18 106.9 . . ? C19 C18 H18 106.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 C22 113.1(2) . . ? N3 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N3 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? N4 C22 C23 121.7(3) . . ? N4 C22 C21 118.4(2) . . ? C23 C22 C21 119.8(2) . . ? C24 C23 C22 118.4(3) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 118.7(3) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? N4 C26 C25 121.6(3) . . ? N4 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? O3 C27 O4 125.1(2) . . ? O3 C27 C28 116.2(2) . . ? O4 C27 C28 118.7(2) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? F3 P1 F4 89.91(13) . . ? F3 P1 F6 89.89(16) . . ? F4 P1 F6 90.25(12) . . ? F3 P1 F2 91.00(13) . . ? F4 P1 F2 178.98(12) . . ? F6 P1 F2 90.23(11) . . ? F3 P1 F5 179.21(14) . . ? F4 P1 F5 89.39(12) . . ? F6 P1 F5 90.48(14) . . ? F2 P1 F5 89.70(12) . . ? F3 P1 F1 89.32(14) . . ? F4 P1 F1 90.59(12) . . ? F6 P1 F1 178.85(14) . . ? F2 P1 F1 88.94(11) . . ? F5 P1 F1 90.31(11) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.292 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.077