# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jian-Ping Lang' _publ_contact_author_email JPLANG@SUDA.EDU.CN _publ_section_title ; Unique Formation of Mono-, Tetra- and Nona-nuclear Zinc Complexes from Protonolysis Reactions of [Zn(dmpzm)Et2] ; loop_ _publ_author_name 'Jian-Ping Lang' 'Mei-Ling Cheng' 'Hong-Xi Li' 'Lei-Lei Liu' 'Hui-Hui Wang' 'Yong Zhang' # Attachment 'JPLangCIF_revised_.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 704329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H26 N4 Zn' _chemical_formula_sum 'C15 H26 N4 Zn' _chemical_formula_weight 327.77 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3359(17) _cell_length_b 14.195(3) _cell_length_c 14.467(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.53(3) _cell_angle_gamma 90.00 _cell_volume 1664.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6499 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.452 _exptl_absorpt_correction_T_max 0.643 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15690 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3023 _reflns_number_gt 2451 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Shelxl-97 (Sheldrick, 1997)' _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^)+(0.0639P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3023 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.003 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 0.22442(5) 0.04033(3) 0.26371(3) 0.02698(19) Uani 1 1 d . . . N1 N 0.1808(3) 0.05001(17) 0.1036(2) 0.0240(6) Uani 1 1 d . . . N2 N 0.2243(4) -0.02397(17) 0.05536(19) 0.0244(6) Uani 1 1 d . . . N3 N 0.4143(4) -0.06987(18) 0.24897(19) 0.0268(6) Uani 1 1 d . . . N4 N 0.3901(3) -0.12704(17) 0.17039(18) 0.0237(6) Uani 1 1 d . . . C1 C 0.1264(5) 0.2189(2) 0.0734(3) 0.0430(10) Uani 1 1 d . . . H1A H 0.0379 0.2138 0.1053 0.065 Uiso 1 1 calc R . . H1B H 0.0916 0.2572 0.0176 0.065 Uiso 1 1 calc R . . H1C H 0.2203 0.2474 0.1153 0.065 Uiso 1 1 calc R . . C2 C 0.1716(4) 0.1235(2) 0.0456(2) 0.0278(8) Uani 1 1 d . . . C3 C 0.2141(4) 0.0966(2) -0.0388(2) 0.0309(8) Uani 1 1 d . . . H3 H 0.2184 0.1353 -0.0901 0.037 Uiso 1 1 calc R . . C4 C 0.2478(4) 0.0025(3) -0.0311(2) 0.0270(7) Uani 1 1 d . . . C5 C 0.3008(6) -0.0641(3) -0.0982(3) 0.0473(11) Uani 1 1 d . . . H5A H 0.4006 -0.0953 -0.0662 0.071 Uiso 1 1 calc R . . H5B H 0.3200 -0.0297 -0.1517 0.071 Uiso 1 1 calc R . . H5C H 0.2158 -0.1101 -0.1197 0.071 Uiso 1 1 calc R . . C6 C 0.2371(4) -0.1161(2) 0.0990(2) 0.0249(7) Uani 1 1 d . . . H6A H 0.2310 -0.1638 0.0503 0.030 Uiso 1 1 calc R . . H6B H 0.1448 -0.1255 0.1282 0.030 Uiso 1 1 calc R . . C7 C 0.5122(5) -0.2653(2) 0.1035(3) 0.0348(9) Uani 1 1 d . . . H7A H 0.4183 -0.3058 0.0981 0.052 Uiso 1 1 calc R . . H7B H 0.6115 -0.3019 0.1215 0.052 Uiso 1 1 calc R . . H7C H 0.5078 -0.2354 0.0434 0.052 Uiso 1 1 calc R . . C8 C 0.5109(4) -0.1914(2) 0.1777(2) 0.0251(7) Uani 1 1 d . . . C9 C 0.6208(4) -0.1738(2) 0.2627(2) 0.0295(8) Uani 1 1 d . . . H9 H 0.7186 -0.2059 0.2875 0.035 Uiso 1 1 calc R . . C10 C 0.5571(4) -0.0982(2) 0.3044(2) 0.0252(7) Uani 1 1 d . . . C11 C 0.6235(5) -0.0520(2) 0.3983(3) 0.0369(9) Uani 1 1 d . . . H11A H 0.5527 -0.0008 0.4062 0.055 Uiso 1 1 calc R . . H11B H 0.7323 -0.0283 0.4007 0.055 Uiso 1 1 calc R . . H11C H 0.6284 -0.0970 0.4483 0.055 Uiso 1 1 calc R . . C12 C 0.0456(5) -0.0378(3) 0.2958(3) 0.0447(11) Uani 1 1 d . . . H12A H -0.0562 -0.0019 0.2817 0.054 Uiso 1 1 calc R . . H12B H 0.0287 -0.0933 0.2555 0.054 Uiso 1 1 calc R . . C13 C 0.0814(5) -0.0684(3) 0.3976(3) 0.0487(11) Uani 1 1 d . . . H13A H 0.1918 -0.0927 0.4159 0.073 Uiso 1 1 calc R . . H13B H 0.0047 -0.1167 0.4051 0.073 Uiso 1 1 calc R . . H13C H 0.0707 -0.0155 0.4371 0.073 Uiso 1 1 calc R . . C14 C 0.3551(4) 0.1563(2) 0.3107(2) 0.0307(8) Uani 1 1 d . . . H14A H 0.2820 0.2101 0.2959 0.037 Uiso 1 1 calc R . . H14B H 0.3903 0.1522 0.3794 0.037 Uiso 1 1 calc R . . C15 C 0.5075(4) 0.1759(2) 0.2719(3) 0.0375(9) Uani 1 1 d . . . H15A H 0.5829 0.1239 0.2869 0.056 Uiso 1 1 calc R . . H15B H 0.5606 0.2323 0.3004 0.056 Uiso 1 1 calc R . . H15C H 0.4748 0.1837 0.2042 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0267(3) 0.0285(3) 0.0271(3) -0.00492(15) 0.0090(2) -0.00749(15) N1 0.0245(15) 0.0237(15) 0.0248(15) 0.0009(11) 0.0079(13) -0.0024(11) N2 0.0309(16) 0.0218(14) 0.0192(15) -0.0008(11) 0.0032(13) 0.0001(12) N3 0.0327(17) 0.0228(14) 0.0223(15) -0.0028(11) 0.0009(13) -0.0044(12) N4 0.0273(15) 0.0204(14) 0.0220(15) -0.0024(10) 0.0030(12) -0.0020(11) C1 0.049(2) 0.029(2) 0.049(2) 0.0046(17) 0.006(2) 0.0047(17) C2 0.0229(18) 0.0283(18) 0.0303(19) 0.0050(14) 0.0025(15) -0.0037(14) C3 0.0250(18) 0.038(2) 0.0282(19) 0.0130(15) 0.0041(16) -0.0020(15) C4 0.0205(18) 0.041(2) 0.0201(17) 0.0013(15) 0.0056(14) 0.0005(15) C5 0.062(3) 0.056(2) 0.023(2) 0.0009(18) 0.008(2) 0.017(2) C6 0.0273(18) 0.0228(17) 0.0228(17) -0.0027(13) 0.0021(15) -0.0034(14) C7 0.038(2) 0.0265(18) 0.041(2) -0.0075(15) 0.0128(18) 0.0017(16) C8 0.0265(18) 0.0221(16) 0.0292(19) 0.0037(13) 0.0112(15) -0.0025(14) C9 0.0274(19) 0.0306(19) 0.0304(19) 0.0071(14) 0.0064(16) 0.0027(15) C10 0.0241(18) 0.0281(18) 0.0233(18) 0.0049(13) 0.0052(15) -0.0054(14) C11 0.035(2) 0.045(2) 0.027(2) 0.0004(15) -0.0015(17) -0.0016(16) C12 0.043(2) 0.062(3) 0.029(2) -0.0016(17) 0.0065(19) -0.0239(19) C13 0.040(2) 0.056(2) 0.052(3) 0.019(2) 0.015(2) 0.004(2) C14 0.0310(19) 0.0285(18) 0.033(2) -0.0116(15) 0.0092(16) -0.0027(15) C15 0.032(2) 0.031(2) 0.050(2) -0.0059(16) 0.0121(19) -0.0066(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 C12 1.998(4) . ? Zn1 C14 2.003(3) . ? Zn1 N1 2.263(3) . ? Zn1 N3 2.271(3) . ? N1 C2 1.329(4) . ? N1 N2 1.357(3) . ? N2 C4 1.363(4) . ? N2 C6 1.445(4) . ? N3 C10 1.332(4) . ? N3 N4 1.373(3) . ? N4 C8 1.345(4) . ? N4 C6 1.450(4) . ? C1 C2 1.487(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.403(5) . ? C3 C4 1.365(5) . ? C3 H3 0.9300 . ? C4 C5 1.494(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.503(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.373(5) . ? C9 C10 1.395(5) . ? C9 H9 0.9300 . ? C10 C11 1.494(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.497(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.529(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 C12 Zn1 C14 138.89(15) . . ? C12 Zn1 N1 108.76(13) . . ? C14 Zn1 N1 104.00(12) . . ? C12 Zn1 N3 102.34(15) . . ? C14 Zn1 N3 105.19(12) . . ? N1 Zn1 N3 83.94(10) . . ? C2 N1 N2 105.4(3) . . ? C2 N1 Zn1 131.7(2) . . ? N2 N1 Zn1 118.78(19) . . ? N1 N2 C4 111.9(3) . . ? N1 N2 C6 118.5(3) . . ? C4 N2 C6 129.6(3) . . ? C10 N3 N4 104.9(3) . . ? C10 N3 Zn1 134.1(2) . . ? N4 N3 Zn1 121.0(2) . . ? C8 N4 N3 112.0(3) . . ? C8 N4 C6 130.3(3) . . ? N3 N4 C6 117.4(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.3(3) . . ? N1 C2 C1 121.7(3) . . ? C3 C2 C1 128.0(3) . . ? C4 C3 C2 106.5(3) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? N2 C4 C3 105.9(3) . . ? N2 C4 C5 123.4(3) . . ? C3 C4 C5 130.7(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 N4 111.8(2) . . ? N2 C6 H6A 109.3 . . ? N4 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? N4 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 C9 106.1(3) . . ? N4 C8 C7 123.2(3) . . ? C9 C8 C7 130.7(3) . . ? C8 C9 C10 106.6(3) . . ? C8 C9 H9 126.7 . . ? C10 C9 H9 126.7 . . ? N3 C10 C9 110.4(3) . . ? N3 C10 C11 120.2(3) . . ? C9 C10 C11 129.3(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 Zn1 113.7(3) . . ? C13 C12 H12A 108.8 . . ? Zn1 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? Zn1 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? 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 . . ? C15 C14 Zn1 117.2(2) . . ? C15 C14 H14A 108.0 . . ? Zn1 C14 H14A 108.0 . . ? C15 C14 H14B 108.0 . . ? Zn1 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.718 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.121 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 704330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N4 O4 Zn' _chemical_formula_sum 'C15 H22 N4 O4 Zn' _chemical_formula_weight 387.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 13.681(3) _cell_length_b 8.2077(16) _cell_length_c 15.815(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.97(3) _cell_angle_gamma 90.00 _cell_volume 1758.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6075 _cell_measurement_theta_min 3.0088 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.572 _exptl_absorpt_correction_T_max 0.6549 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16535 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3215 _reflns_number_gt 2832 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Shelxl-97 (Sheldrick, 1997)' _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^)+(0.0795P)^2^+4.4920P] 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 3215 _refine_ls_number_parameters 211 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 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 0.25247(4) 0.41542(7) 0.65745(3) 0.0386(2) Uani 1 1 d U . . O1 O 0.2650(4) 0.1902(6) 0.6978(3) 0.0721(9) Uani 1 1 d U . . O2 O 0.1737(4) 0.1407(6) 0.5766(3) 0.0721(9) Uani 1 1 d . . . O3 O 0.2380(4) 0.5272(6) 0.5479(3) 0.0732(9) Uani 1 1 d U . . O4 O 0.3562(4) 0.3582(6) 0.5324(3) 0.0732(9) Uani 1 1 d U . . N1 N 0.3505(3) 0.5186(5) 0.7552(2) 0.0377(9) Uani 1 1 d . . . N2 N 0.3255(3) 0.5124(5) 0.8365(2) 0.0395(9) Uani 1 1 d . . . N3 N 0.1345(3) 0.5026(5) 0.7178(2) 0.0362(9) Uani 1 1 d . . . N4 N 0.1498(3) 0.5102(5) 0.8053(2) 0.0368(9) Uani 1 1 d . . . C1 C 0.4860(4) 0.6380(8) 0.6872(4) 0.0596(15) Uani 1 1 d . . . H1A H 0.4677 0.5553 0.6431 0.089 Uiso 1 1 calc R . . H1B H 0.5576 0.6359 0.7045 0.089 Uiso 1 1 calc R . . H1C H 0.4662 0.7459 0.6643 0.089 Uiso 1 1 calc R . . C2 C 0.4350(4) 0.6030(6) 0.7627(3) 0.0427(12) Uani 1 1 d . . . C3 C 0.4632(4) 0.6478(7) 0.8476(3) 0.0478(12) Uani 1 1 d . . . H3 H 0.5207 0.7074 0.8696 0.057 Uiso 1 1 calc R . . C4 C 0.3928(4) 0.5899(6) 0.8933(3) 0.0442(12) Uani 1 1 d . . . C5 C 0.3837(5) 0.5986(9) 0.9860(4) 0.0642(17) Uani 1 1 d . . . H5A H 0.3237 0.6589 0.9937 0.096 Uiso 1 1 calc R . . H5B H 0.4414 0.6546 1.0163 0.096 Uiso 1 1 calc R . . H5C H 0.3800 0.4881 1.0088 0.096 Uiso 1 1 calc R . . C6 C 0.2355(4) 0.4302(6) 0.8496(3) 0.0400(11) Uani 1 1 d . . . H6A H 0.2377 0.3164 0.8292 0.048 Uiso 1 1 calc R . . H6B H 0.2306 0.4271 0.9115 0.048 Uiso 1 1 calc R . . C7 C 0.0767(4) 0.6281(8) 0.9281(3) 0.0548(14) Uani 1 1 d . . . H7A H 0.0959 0.5288 0.9607 0.082 Uiso 1 1 calc R . . H7B H 0.0101 0.6605 0.9374 0.082 Uiso 1 1 calc R . . H7C H 0.1233 0.7156 0.9471 0.082 Uiso 1 1 calc R . . C8 C 0.0781(4) 0.5964(6) 0.8350(3) 0.0400(11) Uani 1 1 d . . . C9 C 0.0142(4) 0.6442(7) 0.7654(3) 0.0446(12) Uani 1 1 d . . . H9 H -0.0444 0.7063 0.7657 0.053 Uiso 1 1 calc R . . C10 C 0.0510(4) 0.5851(6) 0.6943(3) 0.0401(11) Uani 1 1 d . . . C11 C 0.0105(4) 0.6037(9) 0.6017(4) 0.0612(16) Uani 1 1 d . . . H11A H 0.0640 0.5912 0.5669 0.092 Uiso 1 1 calc R . . H11B H -0.0192 0.7120 0.5921 0.092 Uiso 1 1 calc R . . H11C H -0.0399 0.5202 0.5857 0.092 Uiso 1 1 calc R . . C12 C 0.2194(4) 0.0927(6) 0.6442(4) 0.0457(12) Uani 1 1 d U . . C13 C 0.2232(7) -0.0847(7) 0.6673(5) 0.079(2) Uani 1 1 d . . . H13A H 0.1734 -0.1082 0.7045 0.118 Uiso 1 1 calc R . . H13B H 0.2889 -0.1113 0.6972 0.118 Uiso 1 1 calc R . . H13C H 0.2100 -0.1504 0.6152 0.118 Uiso 1 1 calc R . . C14 C 0.2962(4) 0.4572(7) 0.5034(4) 0.0497(13) Uani 1 1 d U . . C15 C 0.2860(6) 0.5085(9) 0.4114(4) 0.074(2) Uani 1 1 d . . . H15A H 0.3515 0.5137 0.3930 0.112 Uiso 1 1 calc R . . H15B H 0.2547 0.6160 0.4050 0.112 Uiso 1 1 calc R . . H15C H 0.2451 0.4291 0.3762 0.112 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0408(4) 0.0416(4) 0.0337(3) -0.0030(2) 0.0059(2) 0.0004(2) O1 0.082(2) 0.0608(19) 0.0685(19) 0.0046(16) -0.0081(17) -0.0136(17) O2 0.082(2) 0.0608(19) 0.0685(19) 0.0046(16) -0.0081(17) -0.0136(17) O3 0.077(2) 0.075(2) 0.071(2) 0.0154(17) 0.0214(17) 0.0130(18) O4 0.077(2) 0.075(2) 0.071(2) 0.0154(17) 0.0214(17) 0.0130(18) N1 0.038(2) 0.040(2) 0.034(2) -0.0040(17) 0.0036(17) -0.0011(18) N2 0.042(2) 0.042(2) 0.033(2) 0.0007(17) -0.0013(17) 0.0008(18) N3 0.040(2) 0.042(2) 0.0274(18) -0.0012(16) 0.0065(16) -0.0003(18) N4 0.041(2) 0.042(2) 0.0281(19) 0.0012(17) 0.0055(16) -0.0013(18) C1 0.049(3) 0.071(4) 0.060(4) -0.001(3) 0.010(3) -0.013(3) C2 0.034(2) 0.044(3) 0.049(3) 0.002(2) 0.002(2) 0.001(2) C3 0.043(3) 0.047(3) 0.050(3) -0.003(2) -0.005(2) -0.001(2) C4 0.041(3) 0.049(3) 0.039(3) -0.005(2) -0.008(2) 0.009(2) C5 0.061(4) 0.086(5) 0.041(3) -0.010(3) -0.007(3) 0.011(3) C6 0.045(3) 0.038(3) 0.037(3) 0.004(2) 0.006(2) 0.001(2) C7 0.058(3) 0.067(4) 0.041(3) -0.009(3) 0.012(3) 0.003(3) C8 0.039(3) 0.042(3) 0.041(3) -0.006(2) 0.013(2) -0.003(2) C9 0.040(3) 0.051(3) 0.044(3) 0.003(2) 0.009(2) 0.009(2) C10 0.037(2) 0.048(3) 0.035(2) 0.005(2) 0.003(2) -0.001(2) C11 0.050(3) 0.089(5) 0.043(3) 0.003(3) -0.001(3) 0.008(3) C12 0.050(3) 0.039(3) 0.048(3) 0.001(2) 0.007(2) -0.006(2) C13 0.133(7) 0.038(3) 0.068(4) -0.006(3) 0.022(4) -0.012(4) C14 0.045(3) 0.047(3) 0.058(3) 0.006(3) 0.011(2) 0.000(2) C15 0.118(6) 0.065(4) 0.050(3) -0.005(3) 0.043(4) -0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.946(5) . ? Zn1 O1 1.955(5) . ? Zn1 N1 2.081(4) . ? Zn1 N3 2.110(4) . ? O1 C12 1.266(7) . ? O2 C12 1.225(7) . ? O3 C14 1.270(7) . ? O4 C14 1.200(7) . ? N1 C2 1.338(6) . ? N1 N2 1.377(5) . ? N2 C4 1.352(6) . ? N2 C6 1.443(6) . ? N3 C10 1.336(6) . ? N3 N4 1.372(5) . ? N4 C8 1.347(6) . ? N4 C6 1.439(6) . ? C1 C2 1.493(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.394(7) . ? C3 C4 1.368(8) . ? C3 H3 0.9500 . ? C4 C5 1.489(8) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.498(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.365(7) . ? C9 C10 1.382(7) . ? C9 H9 0.9500 . ? C10 C11 1.500(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.500(8) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.502(8) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 O3 Zn1 O1 136.8(2) . . ? O3 Zn1 N1 116.4(2) . . ? O1 Zn1 N1 97.14(17) . . ? O3 Zn1 N3 104.67(18) . . ? O1 Zn1 N3 102.17(19) . . ? N1 Zn1 N3 88.88(15) . . ? C12 O1 Zn1 111.5(4) . . ? C14 O3 Zn1 106.6(4) . . ? C2 N1 N2 105.1(4) . . ? C2 N1 Zn1 137.4(3) . . ? N2 N1 Zn1 117.4(3) . . ? C4 N2 N1 111.6(4) . . ? C4 N2 C6 129.8(4) . . ? N1 N2 C6 118.6(4) . . ? C10 N3 N4 105.2(4) . . ? C10 N3 Zn1 136.4(3) . . ? N4 N3 Zn1 116.9(3) . . ? C8 N4 N3 111.1(4) . . ? C8 N4 C6 130.8(4) . . ? N3 N4 C6 118.1(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.0(5) . . ? N1 C2 C1 121.5(5) . . ? C3 C2 C1 128.5(5) . . ? C4 C3 C2 107.2(5) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? N2 C4 C3 106.1(4) . . ? N2 C4 C5 122.3(5) . . ? C3 C4 C5 131.6(5) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 N2 111.7(4) . . ? N4 C6 H6A 109.3 . . ? N2 C6 H6A 109.3 . . ? N4 C6 H6B 109.3 . . ? N2 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 C9 106.6(4) . . ? N4 C8 C7 122.9(5) . . ? C9 C8 C7 130.5(5) . . ? C8 C9 C10 106.9(4) . . ? C8 C9 H9 126.6 . . ? C10 C9 H9 126.6 . . ? N3 C10 C9 110.3(4) . . ? N3 C10 C11 120.6(5) . . ? C9 C10 C11 129.1(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O1 121.7(5) . . ? O2 C12 C13 121.4(5) . . ? O1 C12 C13 116.9(5) . . ? 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 . . ? O4 C14 O3 122.8(6) . . ? O4 C14 C15 121.8(6) . . ? O3 C14 C15 115.4(5) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3 O4 0.95 2.46 3.374(7) 161 2_656 C11 H11A O3 0.98 2.50 3.398(8) 152 . C6 H6A O1 0.99 2.40 3.174(7) 134 . C7 H7A O2 0.98 2.43 3.359(8) 158 4_566 C7 H7B O2 0.98 2.50 3.418(8) 156 2_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.291 _refine_diff_density_min -1.273 _refine_diff_density_rms 0.092 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 704331' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 N4 O2 Zn' _chemical_formula_sum 'C14 H22 N4 O2 Zn' _chemical_formula_weight 343.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8314(16) _cell_length_b 10.326(2) _cell_length_c 11.652(2) _cell_angle_alpha 106.46(3) _cell_angle_beta 106.65(3) _cell_angle_gamma 102.01(3) _cell_volume 821.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3047 _cell_measurement_theta_min 3.4124 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4157 _exptl_absorpt_correction_T_max 0.7959 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8100 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2983 _reflns_number_gt 2445 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Shelxl-97 (Sheldrick, 1997)' _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^)+(0.0462P)^2^+0.8720P] 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 2983 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.001 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 0.47505(7) 0.20809(5) 0.31411(5) 0.0439(2) Uani 1 1 d . . . O1 O 0.2757(4) 0.2316(3) 0.1773(3) 0.0486(8) Uani 1 1 d U . . O2 O 0.1376(5) 0.3684(4) 0.0968(4) 0.0758(11) Uani 1 1 d . . . N1 N 0.5253(5) 0.0405(4) 0.1913(3) 0.0414(8) Uani 1 1 d . . . N2 N 0.3878(5) -0.0887(4) 0.1260(3) 0.0409(8) Uani 1 1 d . . . N3 N 0.1989(5) -0.0766(3) 0.2546(3) 0.0388(8) Uani 1 1 d . . . N4 N 0.2982(5) 0.0538(3) 0.3504(3) 0.0389(8) Uani 1 1 d . . . C1 C 0.8614(7) 0.1377(6) 0.2330(6) 0.0664(15) Uani 1 1 d . . . H1A H 0.8397 0.2272 0.2717 0.100 Uiso 1 1 calc R . . H1B H 0.9121 0.1446 0.1664 0.100 Uiso 1 1 calc R . . H1C H 0.9513 0.1192 0.2995 0.100 Uiso 1 1 calc R . . C2 C 0.6794(6) 0.0183(5) 0.1737(4) 0.0435(10) Uani 1 1 d . . . C3 C 0.6384(7) -0.1233(5) 0.0974(4) 0.0540(12) Uani 1 1 d . . . H3 H 0.7237 -0.1657 0.0702 0.065 Uiso 1 1 calc R . . C4 C 0.4546(7) -0.1901(5) 0.0688(4) 0.0474(11) Uani 1 1 d . . . C5 C 0.3377(9) -0.3412(5) -0.0063(5) 0.0725(16) Uani 1 1 d . . . H5A H 0.4043 -0.3902 -0.0545 0.109 Uiso 1 1 calc R . . H5B H 0.2181 -0.3453 -0.0665 0.109 Uiso 1 1 calc R . . H5C H 0.3136 -0.3876 0.0526 0.109 Uiso 1 1 calc R . . C6 C 0.2025(6) -0.0964(4) 0.1278(4) 0.0418(10) Uani 1 1 d . . . H6A H 0.1618 -0.0223 0.0995 0.050 Uiso 1 1 calc R . . H6B H 0.1129 -0.1903 0.0664 0.050 Uiso 1 1 calc R . . C7 C 0.0039(8) -0.3203(5) 0.2191(5) 0.0642(14) Uani 1 1 d . . . H7A H -0.0849 -0.3247 0.1383 0.096 Uiso 1 1 calc R . . H7B H -0.0654 -0.3613 0.2651 0.096 Uiso 1 1 calc R . . H7C H 0.0882 -0.3743 0.2005 0.096 Uiso 1 1 calc R . . C8 C 0.1168(6) -0.1685(4) 0.3009(4) 0.0443(10) Uani 1 1 d . . . C9 C 0.1630(7) -0.0953(5) 0.4287(5) 0.0515(12) Uani 1 1 d . . . H9 H 0.1254 -0.1309 0.4874 0.062 Uiso 1 1 calc R . . C10 C 0.2761(6) 0.0420(5) 0.4568(4) 0.0435(10) Uani 1 1 d . . . C11 C 0.3676(8) 0.1639(5) 0.5823(4) 0.0592(13) Uani 1 1 d . . . H11A H 0.4896 0.2191 0.5877 0.089 Uiso 1 1 calc R . . H11B H 0.3858 0.1280 0.6528 0.089 Uiso 1 1 calc R . . H11C H 0.2875 0.2249 0.5890 0.089 Uiso 1 1 calc R . . C12 C 0.6733(8) 0.3774(5) 0.4523(5) 0.0650(14) Uani 1 1 d . . . H12A H 0.6201 0.4184 0.5162 0.078 Uiso 1 1 calc R . . H12B H 0.7753 0.3455 0.4963 0.078 Uiso 1 1 calc R . . C13 C 0.7588(9) 0.4936(6) 0.4132(7) 0.100(2) Uani 1 1 d . . . H13A H 0.8221 0.4574 0.3557 0.150 Uiso 1 1 calc R . . H13B H 0.8502 0.5733 0.4900 0.150 Uiso 1 1 calc R . . H13C H 0.6600 0.5261 0.3684 0.150 Uiso 1 1 calc R . . C14 C 0.2482(7) 0.3457(5) 0.1800(5) 0.0551(12) Uani 1 1 d U . . H14 H 0.3228 0.4257 0.2566 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0410(3) 0.0376(3) 0.0489(3) 0.0149(2) 0.0135(2) 0.0097(2) O1 0.0530(19) 0.0389(17) 0.0523(19) 0.0160(14) 0.0144(15) 0.0191(15) O2 0.075(3) 0.055(2) 0.071(2) 0.0221(19) -0.011(2) 0.0240(19) N1 0.042(2) 0.0398(19) 0.045(2) 0.0176(17) 0.0178(17) 0.0137(17) N2 0.040(2) 0.043(2) 0.039(2) 0.0137(16) 0.0145(16) 0.0133(17) N3 0.037(2) 0.0371(19) 0.040(2) 0.0137(16) 0.0137(16) 0.0086(16) N4 0.041(2) 0.0352(18) 0.0384(19) 0.0113(16) 0.0136(16) 0.0116(16) C1 0.044(3) 0.086(4) 0.089(4) 0.050(3) 0.034(3) 0.023(3) C2 0.040(2) 0.060(3) 0.045(3) 0.027(2) 0.022(2) 0.024(2) C3 0.059(3) 0.071(3) 0.049(3) 0.024(3) 0.029(3) 0.039(3) C4 0.059(3) 0.050(3) 0.038(2) 0.014(2) 0.020(2) 0.027(2) C5 0.092(4) 0.052(3) 0.063(3) 0.002(3) 0.027(3) 0.030(3) C6 0.041(3) 0.039(2) 0.037(2) 0.0117(19) 0.008(2) 0.0094(19) C7 0.073(4) 0.046(3) 0.067(3) 0.023(3) 0.024(3) 0.003(3) C8 0.042(3) 0.040(2) 0.053(3) 0.023(2) 0.017(2) 0.009(2) C9 0.059(3) 0.054(3) 0.056(3) 0.033(2) 0.031(2) 0.017(2) C10 0.047(3) 0.048(3) 0.042(3) 0.020(2) 0.020(2) 0.022(2) C11 0.075(4) 0.057(3) 0.043(3) 0.014(2) 0.021(3) 0.023(3) C12 0.064(3) 0.049(3) 0.059(3) 0.012(2) 0.009(3) 0.004(3) C13 0.072(4) 0.050(3) 0.145(7) 0.039(4) 0.004(4) -0.001(3) C14 0.049(3) 0.048(3) 0.049(3) 0.008(2) 0.001(2) 0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 C12 1.975(5) . ? Zn1 O1 1.997(3) . ? Zn1 N1 2.098(4) . ? Zn1 N4 2.106(3) . ? O1 C14 1.234(5) . ? O2 C14 1.216(5) . ? N1 C2 1.335(5) . ? N1 N2 1.369(5) . ? N2 C4 1.359(5) . ? N2 C6 1.443(5) . ? N3 C8 1.357(5) . ? N3 N4 1.371(4) . ? N3 C6 1.442(5) . ? N4 C10 1.335(5) . ? C1 C2 1.500(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.391(6) . ? C3 C4 1.356(7) . ? C3 H3 0.9500 . ? C4 C5 1.487(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.497(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.364(6) . ? C9 C10 1.396(6) . ? C9 H9 0.9500 . ? C10 C11 1.489(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.499(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14 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 C12 Zn1 O1 119.94(18) . . ? C12 Zn1 N1 124.5(2) . . ? O1 Zn1 N1 96.58(13) . . ? C12 Zn1 N4 123.04(19) . . ? O1 Zn1 N4 97.37(13) . . ? N1 Zn1 N4 87.60(13) . . ? C14 O1 Zn1 124.9(3) . . ? C2 N1 N2 105.3(3) . . ? C2 N1 Zn1 134.0(3) . . ? N2 N1 Zn1 119.7(3) . . ? C4 N2 N1 111.5(4) . . ? C4 N2 C6 131.0(4) . . ? N1 N2 C6 117.6(3) . . ? C8 N3 N4 110.8(3) . . ? C8 N3 C6 131.1(4) . . ? N4 N3 C6 118.1(3) . . ? C10 N4 N3 105.8(3) . . ? C10 N4 Zn1 134.0(3) . . ? N3 N4 Zn1 119.3(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.7(4) . . ? N1 C2 C1 120.5(4) . . ? C3 C2 C1 129.8(4) . . ? C4 C3 C2 107.7(4) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? C3 C4 N2 105.8(4) . . ? C3 C4 C5 130.9(4) . . ? N2 C4 C5 123.3(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 N2 111.5(3) . . ? N3 C6 H6A 109.3 . . ? N2 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? N2 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 106.7(4) . . ? N3 C8 C7 122.8(4) . . ? C9 C8 C7 130.5(4) . . ? C8 C9 C10 106.9(4) . . ? C8 C9 H9 126.6 . . ? C10 C9 H9 126.6 . . ? N4 C10 C9 109.8(4) . . ? N4 C10 C11 121.0(4) . . ? C9 C10 C11 129.1(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 Zn1 117.0(4) . . ? C13 C12 H12A 108.0 . . ? Zn1 C12 H12A 108.0 . . ? C13 C12 H12B 108.0 . . ? Zn1 C12 H12B 108.0 . . ? H12A C12 H12B 107.3 . . ? 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 . . ? O2 C14 O1 128.0(5) . . ? O2 C14 H14 116.0 . . ? O1 C14 H14 116.0 . . ? 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 C6 H6A O1 0.99 2.39 3.167(5) 135.0 . C6 H6B O2 0.99 2.29 3.249(6) 164.0 2 C7 H7A O2 0.98 2.54 3.380(7) 143.0 2 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.447 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.071 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 704332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H90 N8 O14 Zn9, 2(C7 H8)' _chemical_formula_sum 'C64 H106 N8 O14 Zn9' _chemical_formula_weight 1800.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 23.993(5) _cell_length_b 13.776(3) _cell_length_c 15.394(3) _cell_angle_alpha 90.00 _cell_angle_beta 128.64(3) _cell_angle_gamma 90.00 _cell_volume 3974(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5915 _cell_measurement_theta_min 3.2029 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 2.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.410 _exptl_absorpt_correction_T_max 0.612 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19491 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3781 _reflns_number_gt 3082 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Shelxl-97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+15.2789P] 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 3781 _refine_ls_number_parameters 232 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.002 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 0.85170(4) 0.5000 0.43031(8) 0.0468(3) Uani 1 2 d S . . Zn2 Zn 0.5000 0.5000 0.0000 0.0340(3) Uani 1 4 d S . . Zn3 Zn 0.41002(4) 0.5000 0.09062(7) 0.0357(2) Uani 1 2 d S . . Zn4 Zn 0.55280(16) 0.6306(3) 0.1963(2) 0.0368(7) Uani 0.480(7) 1 d P . 1 Zn4A Zn 0.57779(17) 0.5901(3) 0.2266(2) 0.0405(7) Uani 0.520(7) 1 d P . 2 O1 O 0.7456(3) 0.5000 0.3555(5) 0.0529(14) Uani 1 2 d SD . . O2 O 0.6427(3) 0.5332(4) 0.3129(5) 0.043(2) Uani 0.50 1 d PD . . O3 O 0.5046(2) 0.5000 0.1315(4) 0.0379(11) Uani 1 2 d S . . O4 O 0.4177(2) 0.3890(3) -0.0917(4) 0.0632(12) Uani 1 1 d . . . O5 O 0.36017(17) 0.3853(3) -0.0226(3) 0.0397(8) Uani 1 1 d . . . N1 N 0.8459(2) 0.6086(3) 0.3306(4) 0.0491(12) Uani 1 1 d . . . N2 N 0.8222(2) 0.5866(3) 0.2251(4) 0.0465(11) Uani 1 1 d . . . C1 C 0.9083(4) 0.7435(5) 0.4625(6) 0.075(2) Uani 1 1 d . . . H1A H 0.8720 0.7525 0.4702 0.112 Uiso 1 1 calc R . . H1B H 0.9277 0.8054 0.4651 0.112 Uiso 1 1 calc R . . H1C H 0.9456 0.7034 0.5220 0.112 Uiso 1 1 calc R . . C2 C 0.8770(3) 0.6958(4) 0.3543(6) 0.0540(16) Uani 1 1 d . . . C3 C 0.8727(3) 0.7281(4) 0.2645(6) 0.0636(19) Uani 1 1 d . . . H3 H 0.8904 0.7865 0.2604 0.076 Uiso 1 1 calc R . . C4 C 0.8377(3) 0.6585(4) 0.1836(6) 0.0571(17) Uani 1 1 d . . . C5 C 0.8169(4) 0.6528(5) 0.0701(6) 0.074(2) Uani 1 1 d . . . H5A H 0.8407 0.5990 0.0665 0.111 Uiso 1 1 calc R . . H5B H 0.8302 0.7118 0.0542 0.111 Uiso 1 1 calc R . . H5C H 0.7662 0.6440 0.0164 0.111 Uiso 1 1 calc R . . C6 C 0.7803(4) 0.5000 0.1740(7) 0.0445(19) Uani 1 2 d S . . H6A H 0.7588 0.5000 0.0957 0.053 Uiso 1 2 calc SR . . H6B H 0.7421 0.5000 0.1794 0.053 Uiso 1 2 calc SR . . C7 C 1.0014(4) 0.5000 0.6393(8) 0.061(2) Uani 1 2 d S . . H7A H 1.0316 0.5000 0.7191 0.091 Uiso 1 2 calc SR . . H7B H 1.0109 0.5569 0.6144 0.091 Uiso 0.50 1 calc PR . . H7C H 1.0109 0.4431 0.6144 0.091 Uiso 0.50 1 calc PR . . C8 C 0.9242(4) 0.5000 0.5923(7) 0.055(2) Uani 1 2 d S . . H8A H 0.9164 0.5567 0.6209 0.066 Uiso 0.50 1 calc PR . . H8B H 0.9164 0.4433 0.6209 0.066 Uiso 0.50 1 calc PR . . C9 C 0.7406(6) 0.6379(8) 0.4358(10) 0.056(3) Uiso 0.50 1 d PD . . H9A H 0.7052 0.6707 0.4356 0.084 Uiso 0.50 1 calc PR . . H9B H 0.7574 0.6806 0.4073 0.084 Uiso 0.50 1 calc PR . . H9C H 0.7798 0.6194 0.5105 0.084 Uiso 0.50 1 calc PR . . C10 C 0.7087(5) 0.5497(7) 0.3648(9) 0.042(3) Uani 0.50 1 d PD . . C11 C 0.5467(8) 0.7551(11) 0.2425(13) 0.064(2) Uani 0.520(7) 1 d P . 1 H11A H 0.5260 0.7494 0.2799 0.076 Uiso 0.520(7) 1 calc PR . 1 H11B H 0.5941 0.7825 0.2946 0.076 Uiso 0.520(7) 1 calc PR . 1 C11A C 0.5769(8) 0.7098(11) 0.2914(13) 0.064(2) Uani 0.480(7) 1 d P . 2 H11C H 0.5694 0.6954 0.3451 0.076 Uiso 0.480(7) 1 calc PR . 2 H11D H 0.6228 0.7419 0.3303 0.076 Uiso 0.480(7) 1 calc PR . 2 C12 C 0.4988(7) 0.8244(9) 0.1378(11) 0.064(2) Uani 0.520(7) 1 d P . 1 H12A H 0.5219 0.8352 0.1054 0.095 Uiso 0.520(7) 1 calc PR . 1 H12B H 0.4923 0.8854 0.1607 0.095 Uiso 0.520(7) 1 calc PR . 1 H12C H 0.4531 0.7946 0.0838 0.095 Uiso 0.520(7) 1 calc PR . 1 C12A C 0.5189(8) 0.7761(12) 0.2033(14) 0.064(2) Uani 0.480(7) 1 d P . 2 H12D H 0.5272 0.7920 0.1514 0.095 Uiso 0.480(7) 1 calc PR . 2 H12E H 0.5189 0.8346 0.2373 0.095 Uiso 0.480(7) 1 calc PR . 2 H12F H 0.4736 0.7443 0.1647 0.095 Uiso 0.480(7) 1 calc PR . 2 C13 C 0.4598(5) 0.5000 0.3198(7) 0.075(3) Uani 1 2 d S . . H13A H 0.4476 0.5000 0.3685 0.112 Uiso 1 2 calc SR . . H13B H 0.4873 0.5569 0.3334 0.112 Uiso 0.50 1 calc PR . . H13C H 0.4873 0.4431 0.3334 0.112 Uiso 0.50 1 calc PR . . C14 C 0.3915(4) 0.5000 0.1989(6) 0.0417(18) Uani 1 2 d S . . H14A H 0.3635 0.5569 0.1863 0.050 Uiso 0.50 1 calc PR . . H14B H 0.3635 0.4431 0.1863 0.050 Uiso 0.50 1 calc PR . . C15 C 0.3260(3) 0.2727(4) -0.1626(5) 0.0559(16) Uani 1 1 d . . . H15A H 0.2985 0.2468 -0.1422 0.084 Uiso 1 1 calc R . . H15B H 0.3564 0.2229 -0.1562 0.084 Uiso 1 1 calc R . . H15C H 0.2945 0.2955 -0.2380 0.084 Uiso 1 1 calc R . . C16 C 0.3705(3) 0.3547(4) -0.0873(4) 0.0380(12) Uani 1 1 d . . . C17 C 0.8923(10) 0.5000 0.9182(15) 0.160(7) Uiso 1 2 d S . . H17A H 0.8838 0.5350 0.9627 0.241 Uiso 0.50 1 calc PR . . H17B H 0.9303 0.5306 0.9235 0.241 Uiso 0.50 1 calc PR . . H17C H 0.9055 0.4343 0.9444 0.241 Uiso 0.50 1 calc PR . . C18 C 0.8268(4) 0.5000 0.8008(7) 0.111(2) Uiso 1 2 d SG . . C19 C 0.7606(6) 0.5167(9) 0.7743(8) 0.111(2) Uiso 0.50 1 d PG . . H19 H 0.7580 0.5403 0.8284 0.133 Uiso 0.50 1 calc PR . . C20 C 0.6985(4) 0.4986(12) 0.6681(9) 0.111(2) Uiso 1 2 d SG . . H20 H 0.6543 0.5128 0.6497 0.133 Uiso 0.50 1 calc PR . . C21 C 0.7026(5) 0.4586(10) 0.5884(6) 0.111(2) Uiso 0.50 1 d PG . . H21 H 0.6611 0.4432 0.5179 0.133 Uiso 0.50 1 calc PR . . C22 C 0.7688(6) 0.4419(8) 0.6149(8) 0.111(2) Uiso 0.50 1 d PG . . H22 H 0.7715 0.4169 0.5616 0.133 Uiso 0.50 1 calc PR . . C23 C 0.8309(5) 0.4626(7) 0.7211(10) 0.111(2) Uiso 0.50 1 d PG . . H23 H 0.8751 0.4515 0.7388 0.133 Uiso 0.50 1 calc PR . . 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 0.0308(5) 0.0395(5) 0.0624(6) 0.000 0.0253(5) 0.000 Zn2 0.0308(6) 0.0400(7) 0.0359(6) 0.000 0.0231(5) 0.000 Zn3 0.0307(4) 0.0413(5) 0.0413(5) 0.000 0.0256(4) 0.000 Zn4 0.0357(11) 0.0349(13) 0.0442(11) -0.0046(9) 0.0271(10) 0.0006(9) Zn4A 0.0405(12) 0.0425(14) 0.0410(10) -0.0075(9) 0.0266(10) -0.0075(11) O1 0.032(3) 0.064(4) 0.059(4) 0.000 0.026(3) 0.000 O2 0.024(3) 0.053(5) 0.041(4) 0.001(3) 0.014(3) 0.004(3) O3 0.028(2) 0.052(3) 0.037(3) 0.000 0.021(2) 0.000 O4 0.065(3) 0.087(3) 0.066(3) -0.037(2) 0.055(2) -0.040(2) O5 0.0367(19) 0.043(2) 0.049(2) -0.0066(17) 0.0311(18) -0.0042(16) N1 0.036(2) 0.032(2) 0.070(3) 0.001(2) 0.029(2) -0.001(2) N2 0.033(2) 0.040(3) 0.068(3) 0.004(2) 0.032(2) 0.001(2) C1 0.064(4) 0.049(4) 0.087(5) -0.010(4) 0.035(4) -0.007(3) C2 0.037(3) 0.036(3) 0.081(5) 0.003(3) 0.033(3) 0.000(2) C3 0.049(4) 0.038(3) 0.103(6) 0.005(4) 0.047(4) -0.001(3) C4 0.044(3) 0.048(4) 0.084(5) 0.014(4) 0.043(4) 0.007(3) C5 0.083(5) 0.063(4) 0.104(6) 0.020(4) 0.072(5) 0.011(4) C6 0.028(4) 0.039(4) 0.063(5) 0.000 0.027(4) 0.000 C7 0.033(4) 0.065(6) 0.067(6) 0.000 0.023(4) 0.000 C8 0.035(4) 0.054(5) 0.072(6) 0.000 0.031(4) 0.000 C10 0.024(5) 0.041(6) 0.043(6) 0.003(5) 0.012(5) -0.003(5) C11 0.057(6) 0.056(6) 0.068(7) -0.011(4) 0.034(6) 0.005(4) C11A 0.057(6) 0.056(6) 0.068(7) -0.011(4) 0.034(6) 0.005(4) C12 0.057(6) 0.056(6) 0.068(7) -0.011(4) 0.034(6) 0.005(4) C12A 0.057(6) 0.056(6) 0.068(7) -0.011(4) 0.034(6) 0.005(4) C13 0.069(6) 0.118(9) 0.044(5) 0.000 0.039(5) 0.000 C14 0.053(5) 0.034(4) 0.056(5) 0.000 0.043(4) 0.000 C15 0.048(3) 0.059(4) 0.070(4) -0.022(3) 0.041(3) -0.017(3) C16 0.038(3) 0.037(3) 0.044(3) -0.007(2) 0.028(3) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 C8 1.956(9) . ? Zn1 O1 2.037(5) . ? Zn1 N1 2.085(5) 6_565 ? Zn1 N1 2.085(5) . ? Zn2 O3 1.957(5) 5_665 ? Zn2 O3 1.957(5) . ? Zn2 O4 2.178(4) 5_665 ? Zn2 O4 2.178(4) . ? Zn2 O4 2.178(4) 2_655 ? Zn2 O4 2.178(4) 6_565 ? Zn2 Zn4A 3.0101(18) . ? Zn2 Zn4A 3.0101(18) 5_665 ? Zn2 Zn4A 3.0101(18) 6_565 ? Zn2 Zn4A 3.0101(18) 2_655 ? Zn2 Zn4 3.0315(18) . ? Zn2 Zn4 3.0315(18) 5_665 ? Zn3 O3 1.940(4) . ? Zn3 C14 1.974(7) . ? Zn3 O5 2.089(3) . ? Zn3 O5 2.089(3) 6_565 ? Zn4 C11 1.898(15) . ? Zn4 O3 2.031(3) . ? Zn4 O4 2.142(4) 5_665 ? Zn4 O2 2.199(8) . ? Zn4A O2 1.489(8) . ? Zn4A O3 1.885(4) . ? Zn4A C11A 1.934(14) . ? Zn4A O2 2.118(8) 6_565 ? Zn4A O4 2.165(4) 5_665 ? Zn4A Zn4A 2.481(7) 6_565 ? Zn4A C10 2.520(10) . ? O1 C10 1.196(10) 6_565 ? O1 C10 1.196(10) . ? O2 O2 0.915(12) 6_565 ? O2 C10 1.272(10) . ? O2 C10 1.694(10) 6_565 ? O2 Zn4A 2.118(8) 6_565 ? O3 Zn4A 1.885(4) 6_565 ? O3 Zn4 2.031(3) 6_565 ? O4 C16 1.267(6) . ? O4 Zn4 2.142(4) 5_665 ? O4 Zn4A 2.165(4) 5_665 ? O5 C16 1.241(6) . ? N1 C2 1.338(7) . ? N1 N2 1.378(7) . ? N2 C4 1.352(7) . ? N2 C6 1.437(6) . ? C1 C2 1.485(9) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.393(9) . ? C3 C4 1.367(9) . ? C3 H3 0.9300 . ? C4 C5 1.489(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N2 1.437(6) 6_565 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.510(11) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.488(12) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C10 1.370(19) 6_565 ? C10 O2 1.694(10) 6_565 ? C11 C12 1.588(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11A C12A 1.502(19) . ? C11A H11C 0.9700 . ? C11A H11D 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12A H12D 0.9600 . ? C12A H12E 0.9600 . ? C12A H12F 0.9600 . ? C13 C14 1.530(12) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.488(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 C18 1.479(18) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.3901 . ? C18 C23 1.3898 . ? C19 C20 1.3832 . ? C19 H19 0.9300 . ? C20 C21 1.4040 . ? C20 H20 0.9300 . ? C21 C22 1.3900 . ? C21 H21 0.9300 . ? C22 C23 1.3900 . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 Zn1 O1 121.5(3) . . ? C8 Zn1 N1 122.40(18) . 6_565 ? O1 Zn1 N1 95.67(17) . 6_565 ? C8 Zn1 N1 122.40(18) . . ? O1 Zn1 N1 95.67(17) . . ? N1 Zn1 N1 91.7(3) 6_565 . ? O3 Zn2 O3 180.0(3) 5_665 . ? O3 Zn2 O4 96.51(14) 5_665 5_665 ? O3 Zn2 O4 83.49(14) . 5_665 ? O3 Zn2 O4 83.49(14) 5_665 . ? O3 Zn2 O4 96.51(14) . . ? O4 Zn2 O4 180.0(2) 5_665 . ? O3 Zn2 O4 96.51(14) 5_665 2_655 ? O3 Zn2 O4 83.49(14) . 2_655 ? O4 Zn2 O4 89.1(3) 5_665 2_655 ? O4 Zn2 O4 90.9(3) . 2_655 ? O3 Zn2 O4 83.49(14) 5_665 6_565 ? O3 Zn2 O4 96.51(14) . 6_565 ? O4 Zn2 O4 90.9(3) 5_665 6_565 ? O4 Zn2 O4 89.1(3) . 6_565 ? O4 Zn2 O4 180.0(2) 2_655 6_565 ? O3 Zn2 Zn4A 142.42(10) 5_665 . ? O3 Zn2 Zn4A 37.58(10) . . ? O4 Zn2 Zn4A 45.95(11) 5_665 . ? O4 Zn2 Zn4A 134.05(11) . . ? O4 Zn2 Zn4A 83.29(16) 2_655 . ? O4 Zn2 Zn4A 96.71(16) 6_565 . ? O3 Zn2 Zn4A 37.58(10) 5_665 5_665 ? O3 Zn2 Zn4A 142.42(10) . 5_665 ? O4 Zn2 Zn4A 134.05(11) 5_665 5_665 ? O4 Zn2 Zn4A 45.95(11) . 5_665 ? O4 Zn2 Zn4A 96.71(16) 2_655 5_665 ? O4 Zn2 Zn4A 83.29(16) 6_565 5_665 ? Zn4A Zn2 Zn4A 180.0 . 5_665 ? O3 Zn2 Zn4A 142.42(10) 5_665 6_565 ? O3 Zn2 Zn4A 37.58(10) . 6_565 ? O4 Zn2 Zn4A 83.29(16) 5_665 6_565 ? O4 Zn2 Zn4A 96.71(16) . 6_565 ? O4 Zn2 Zn4A 45.95(11) 2_655 6_565 ? O4 Zn2 Zn4A 134.05(11) 6_565 6_565 ? Zn4A Zn2 Zn4A 48.68(16) . 6_565 ? Zn4A Zn2 Zn4A 131.32(16) 5_665 6_565 ? O3 Zn2 Zn4A 37.58(10) 5_665 2_655 ? O3 Zn2 Zn4A 142.42(10) . 2_655 ? O4 Zn2 Zn4A 96.71(16) 5_665 2_655 ? O4 Zn2 Zn4A 83.29(16) . 2_655 ? O4 Zn2 Zn4A 134.05(11) 2_655 2_655 ? O4 Zn2 Zn4A 45.95(11) 6_565 2_655 ? Zn4A Zn2 Zn4A 131.32(16) . 2_655 ? Zn4A Zn2 Zn4A 48.68(16) 5_665 2_655 ? Zn4A Zn2 Zn4A 180.00(13) 6_565 2_655 ? O3 Zn2 Zn4 138.55(8) 5_665 . ? O3 Zn2 Zn4 41.45(7) . . ? O4 Zn2 Zn4 44.95(10) 5_665 . ? O4 Zn2 Zn4 135.05(10) . . ? O4 Zn2 Zn4 97.18(15) 2_655 . ? O4 Zn2 Zn4 82.82(15) 6_565 . ? Zn4A Zn2 Zn4 13.96(3) . . ? Zn4A Zn2 Zn4 166.04(3) 5_665 . ? Zn4A Zn2 Zn4 61.22(15) 6_565 . ? Zn4A Zn2 Zn4 118.78(15) 2_655 . ? O3 Zn2 Zn4 41.45(8) 5_665 5_665 ? O3 Zn2 Zn4 138.55(8) . 5_665 ? O4 Zn2 Zn4 135.05(10) 5_665 5_665 ? O4 Zn2 Zn4 44.95(10) . 5_665 ? O4 Zn2 Zn4 82.82(15) 2_655 5_665 ? O4 Zn2 Zn4 97.18(15) 6_565 5_665 ? Zn4A Zn2 Zn4 166.04(3) . 5_665 ? Zn4A Zn2 Zn4 13.96(3) 5_665 5_665 ? Zn4A Zn2 Zn4 118.78(15) 6_565 5_665 ? Zn4A Zn2 Zn4 61.22(15) 2_655 5_665 ? Zn4 Zn2 Zn4 180.0 . 5_665 ? O3 Zn3 C14 124.1(3) . . ? O3 Zn3 O5 102.42(13) . . ? C14 Zn3 O5 113.03(16) . . ? O3 Zn3 O5 102.42(13) . 6_565 ? C14 Zn3 O5 113.03(16) . 6_565 ? O5 Zn3 O5 98.3(2) . 6_565 ? C11 Zn4 O3 146.2(5) . . ? C11 Zn4 O4 122.4(5) . 5_665 ? O3 Zn4 O4 82.71(18) . 5_665 ? C11 Zn4 O2 120.7(5) . . ? O3 Zn4 O2 80.1(2) . . ? O4 Zn4 O2 85.5(3) 5_665 . ? C11 Zn4 Zn2 145.9(5) . . ? O3 Zn4 Zn2 39.63(13) . . ? O4 Zn4 Zn2 45.93(10) 5_665 . ? O2 Zn4 Zn2 92.2(2) . . ? O2 Zn4A O3 107.1(3) . . ? O2 Zn4A C11A 109.3(5) . . ? O3 Zn4A C11A 131.1(5) . . ? O2 Zn4A O2 21.5(3) . 6_565 ? O3 Zn4A O2 85.6(2) . 6_565 ? C11A Zn4A O2 126.9(5) . 6_565 ? O2 Zn4A O4 106.0(3) . 5_665 ? O3 Zn4A O4 85.56(18) . 5_665 ? C11A Zn4A O4 113.9(5) . 5_665 ? O2 Zn4A O4 104.5(3) 6_565 5_665 ? O2 Zn4A Zn4A 58.3(2) . 6_565 ? O3 Zn4A Zn4A 48.84(17) . 6_565 ? C11A Zn4A Zn4A 148.5(5) . 6_565 ? O2 Zn4A Zn4A 36.73(17) 6_565 6_565 ? O4 Zn4A Zn4A 97.64(15) 5_665 6_565 ? O2 Zn4A C10 22.2(3) . . ? O3 Zn4A C10 125.1(3) . . ? C11A Zn4A C10 99.3(5) . . ? O2 Zn4A C10 41.7(3) 6_565 . ? O4 Zn4A C10 93.3(3) 5_665 . ? Zn4A Zn4A C10 77.3(2) 6_565 . ? O2 Zn4A Zn2 111.3(3) . . ? O3 Zn4A Zn2 39.29(14) . . ? C11A Zn4A Zn2 138.6(5) . . ? O2 Zn4A Zn2 94.4(2) 6_565 . ? O4 Zn4A Zn2 46.31(10) 5_665 . ? Zn4A Zn4A Zn2 65.66(8) 6_565 . ? C10 Zn4A Zn2 115.5(3) . . ? C10 O1 C10 69.9(10) 6_565 . ? C10 O1 Zn1 133.6(5) 6_565 . ? C10 O1 Zn1 133.6(5) . . ? O2 O2 C10 100.3(5) 6_565 . ? O2 O2 Zn4A 121.7(2) 6_565 . ? C10 O2 Zn4A 131.6(7) . . ? O2 O2 C10 47.6(4) 6_565 6_565 ? C10 O2 C10 52.7(8) . 6_565 ? Zn4A O2 C10 157.5(6) . 6_565 ? C10 O2 Zn4A 132.6(6) . 6_565 ? Zn4A O2 Zn4A 85.0(3) . 6_565 ? C10 O2 Zn4A 81.9(4) 6_565 6_565 ? O2 O2 Zn4 127.59(16) 6_565 . ? C10 O2 Zn4 127.2(6) . . ? C10 O2 Zn4 161.3(6) 6_565 . ? Zn4A O2 Zn4 90.9(2) 6_565 . ? Zn4A O3 Zn4A 82.3(3) . 6_565 ? Zn4A O3 Zn3 125.8(2) . . ? Zn4A O3 Zn3 125.8(2) 6_565 . ? Zn4A O3 Zn2 103.13(18) . . ? Zn4A O3 Zn2 103.13(18) 6_565 . ? Zn3 O3 Zn2 111.4(2) . . ? Zn4A O3 Zn4 103.5(3) 6_565 . ? Zn3 O3 Zn4 110.56(16) . . ? Zn2 O3 Zn4 98.92(15) . . ? Zn4A O3 Zn4 103.5(3) . 6_565 ? Zn3 O3 Zn4 110.56(16) . 6_565 ? Zn2 O3 Zn4 98.92(15) . 6_565 ? Zn4 O3 Zn4 124.6(3) . 6_565 ? C16 O4 Zn4 135.9(3) . 5_665 ? C16 O4 Zn4A 133.0(4) . 5_665 ? C16 O4 Zn2 134.9(3) . . ? Zn4 O4 Zn2 89.13(14) 5_665 . ? Zn4A O4 Zn2 87.74(14) 5_665 . ? C16 O5 Zn3 129.0(3) . . ? C2 N1 N2 105.6(5) . . ? C2 N1 Zn1 132.3(5) . . ? N2 N1 Zn1 119.9(3) . . ? C4 N2 N1 111.3(5) . . ? C4 N2 C6 130.9(6) . . ? N1 N2 C6 117.5(5) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.4(6) . . ? N1 C2 C1 120.6(6) . . ? C3 C2 C1 130.0(6) . . ? C4 C3 C2 107.7(6) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? N2 C4 C3 106.0(6) . . ? N2 C4 C5 121.7(6) . . ? C3 C4 C5 132.2(6) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 N2 112.2(6) . 6_565 ? N2 C6 H6A 109.2 . . ? N2 C6 H6A 109.2 6_565 . ? N2 C6 H6B 109.2 . . ? N2 C6 H6B 109.2 6_565 . ? H6A C6 H6B 107.9 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C7 C8 Zn1 117.3(6) . . ? C7 C8 H8A 108.0 . . ? Zn1 C8 H8A 108.0 . . ? C7 C8 H8B 108.0 . . ? Zn1 C8 H8B 108.0 . . ? H8A C8 H8B 107.2 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 O2 123.1(9) . . ? O1 C10 C10 55.1(5) . 6_565 ? O2 C10 C10 79.7(5) . 6_565 ? O1 C10 C9 118.4(8) . . ? O2 C10 C9 118.4(8) . . ? C10 C10 C9 144.7(6) 6_565 . ? O1 C10 O2 95.8(7) . 6_565 ? C10 C10 O2 47.6(4) 6_565 6_565 ? C9 C10 O2 142.9(9) . 6_565 ? O1 C10 Zn4A 130.6(7) . . ? C10 C10 Zn4A 102.7(2) 6_565 . ? C9 C10 Zn4A 103.8(6) . . ? O2 C10 Zn4A 56.3(3) 6_565 . ? C12 C11 Zn4 109.8(9) . . ? C12 C11 H11A 109.7 . . ? Zn4 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? Zn4 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C12A C11A Zn4A 110.8(10) . . ? C12A C11A H11C 109.5 . . ? Zn4A C11A H11C 109.5 . . ? C12A C11A H11D 109.5 . . ? Zn4A C11A H11D 109.5 . . ? H11C C11A H11D 108.1 . . ? C11A C12A H12D 109.5 . . ? C11A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C11A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C13 C14 Zn3 113.1(5) . . ? C13 C14 H14A 109.0 . . ? Zn3 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? Zn3 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O4 123.3(5) . . ? O5 C16 C15 118.5(4) . . ? O4 C16 C15 118.2(5) . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 120.0 . . ? C19 C18 C17 120.5(10) . . ? C23 C18 C17 118.1(10) . . ? C18 C19 C20 120.5 . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 119.5 . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C18 120.0 . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.749 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.087 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 704333' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H60 N12 O Zn4' _chemical_formula_sum 'C39 H60 N12 O Zn4' _chemical_formula_weight 974.47 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 cubic _symmetry_space_group_name_H-M 'P 21 3' _symmetry_space_group_name_Hall 'P 2ac 2ab 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' _cell_length_a 16.5114(19) _cell_length_b 16.5114(19) _cell_length_c 16.5114(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4501.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 17071 _cell_measurement_theta_min 3.0222 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 2.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.466 _exptl_absorpt_correction_T_max 0.6309 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 44810 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2757 _reflns_number_gt 2654 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Shelxl-97 (Sheldrick, 1997)' _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^)+(0.0435P)^2^+7.3025P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(4) _refine_ls_number_reflns 2757 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.62604(5) 0.24794(5) 0.72225(5) 0.03014(19) Uani 1 1 d . . . Zn2 Zn 0.80731(5) 0.19269(5) 0.69269(5) 0.0246(3) Uani 1 3 d S . . O1 O 0.7379(3) 0.2621(3) 0.7621(3) 0.0274(18) Uani 1 3 d S . . N1 N 0.6202(4) 0.1283(4) 0.6730(3) 0.0316(14) Uani 1 1 d . . . N2 N 0.6710(3) 0.1088(3) 0.6101(3) 0.0273(14) Uani 1 1 d . . . N3 N 0.6995(3) 0.2382(4) 0.5539(3) 0.0293(14) Uani 1 1 d . . . N4 N 0.6481(4) 0.2846(4) 0.5997(4) 0.0306(14) Uani 1 1 d . . . C1 C 0.5001(5) 0.0676(6) 0.7354(6) 0.053(2) Uani 1 1 d . . . H5A H 0.5012 0.0183 0.7662 0.080 Uiso 1 1 calc R . . H5B H 0.4490 0.0722 0.7081 0.080 Uiso 1 1 calc R . . H5C H 0.5072 0.1129 0.7711 0.080 Uiso 1 1 calc R . . C2 C 0.5658(5) 0.0665(5) 0.6754(5) 0.0377(18) Uani 1 1 d . . . C3 C 0.5829(5) 0.0104(5) 0.6162(5) 0.0404(19) Uani 1 1 d . . . H3 H 0.5557 -0.0380 0.6065 0.048 Uiso 1 1 calc R . . C4 C 0.6483(5) 0.0401(4) 0.5743(4) 0.0332(18) Uani 1 1 d . . . C5 C 0.6931(7) 0.0043(6) 0.5033(6) 0.067(3) Uani 1 1 d . . . H1A H 0.6911 0.0413 0.4585 0.101 Uiso 1 1 calc R . . H1B H 0.6682 -0.0460 0.4881 0.101 Uiso 1 1 calc R . . H1C H 0.7485 -0.0052 0.5182 0.101 Uiso 1 1 calc R . . C6 C 0.7373(4) 0.1648(4) 0.5922(4) 0.0288(16) Uani 1 1 d . . . H6 H 0.7726 0.1392 0.5519 0.035 Uiso 1 1 calc R . . C7 C 0.7656(5) 0.2339(5) 0.4182(5) 0.047(2) Uani 1 1 d . . . H7A H 0.8207 0.2457 0.4325 0.071 Uiso 1 1 calc R . . H7B H 0.7539 0.2561 0.3658 0.071 Uiso 1 1 calc R . . H7C H 0.7578 0.1763 0.4170 0.071 Uiso 1 1 calc R . . C8 C 0.7101(4) 0.2704(4) 0.4794(4) 0.0318(16) Uani 1 1 d . . . C9 C 0.6612(4) 0.3381(5) 0.4774(5) 0.0356(18) Uani 1 1 d . . . H9 H 0.6546 0.3734 0.4340 0.043 Uiso 1 1 calc R . . C10 C 0.6234(5) 0.3438(5) 0.5533(5) 0.0379(18) Uani 1 1 d . . . C11 C 0.5656(5) 0.4061(6) 0.5828(5) 0.050(2) Uani 1 1 d . . . H11A H 0.5527 0.3958 0.6385 0.075 Uiso 1 1 calc R . . H11B H 0.5170 0.4040 0.5509 0.075 Uiso 1 1 calc R . . H11C H 0.5898 0.4587 0.5779 0.075 Uiso 1 1 calc R . . C12 C 0.5320(5) 0.2905(7) 0.7819(6) 0.057(2) Uani 1 1 d . . . H12A H 0.5309 0.2642 0.8344 0.068 Uiso 1 1 calc R . . H12B H 0.5415 0.3477 0.7915 0.068 Uiso 1 1 calc R . . C13 C 0.4468(5) 0.2819(7) 0.7441(9) 0.082(4) Uani 1 1 d . . . H13A H 0.4475 0.3025 0.6897 0.123 Uiso 1 1 calc R . . H13B H 0.4085 0.3121 0.7758 0.123 Uiso 1 1 calc R . . H13C H 0.4314 0.2258 0.7435 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0245(4) 0.0352(5) 0.0308(4) -0.0023(4) 0.0017(3) 0.0002(4) Zn2 0.0246(3) 0.0246(3) 0.0246(3) -0.0008(3) 0.0008(3) 0.0008(3) O1 0.0274(18) 0.0274(18) 0.0274(18) 0.0012(19) -0.0012(19) -0.0012(19) N1 0.022(3) 0.042(4) 0.030(3) 0.004(3) -0.001(3) -0.003(3) N2 0.023(3) 0.030(3) 0.029(3) -0.008(2) 0.001(2) -0.007(2) N3 0.024(3) 0.046(3) 0.019(3) -0.006(3) -0.002(2) 0.000(3) N4 0.033(3) 0.029(3) 0.030(3) 0.005(2) -0.008(3) -0.006(3) C1 0.036(5) 0.055(5) 0.069(7) 0.001(5) 0.012(5) -0.008(4) C2 0.043(5) 0.032(4) 0.038(5) 0.003(3) -0.009(4) -0.012(3) C3 0.045(5) 0.034(4) 0.042(5) -0.005(3) -0.013(4) -0.015(4) C4 0.047(5) 0.021(4) 0.032(4) -0.005(3) -0.009(4) -0.004(3) C5 0.097(8) 0.054(6) 0.051(6) -0.027(4) 0.003(6) -0.012(6) C6 0.030(4) 0.032(4) 0.024(3) 0.000(3) 0.004(3) 0.007(3) C7 0.056(5) 0.044(5) 0.041(4) 0.004(4) 0.015(4) 0.004(4) C8 0.037(4) 0.036(4) 0.023(3) -0.004(3) -0.005(3) -0.004(3) C9 0.032(4) 0.040(4) 0.035(4) 0.014(4) 0.002(3) 0.002(3) C10 0.038(4) 0.036(4) 0.040(4) 0.007(4) -0.010(4) -0.001(3) C11 0.049(5) 0.056(6) 0.046(5) -0.002(4) 0.006(4) 0.012(4) C12 0.029(4) 0.070(6) 0.070(7) 0.013(5) 0.006(4) 0.012(4) C13 0.043(5) 0.080(8) 0.123(11) 0.030(7) 0.003(6) 0.021(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 C12 1.968(8) . ? Zn1 O1 1.975(5) . ? Zn1 N1 2.138(7) . ? Zn1 N4 2.143(6) . ? Zn2 O1 1.986(8) . ? Zn2 C6 2.074(7) 7_665 ? Zn2 C6 2.074(7) . ? Zn2 C6 2.074(7) 10_646 ? O1 Zn1 1.975(5) 7_665 ? O1 Zn1 1.975(5) 10_646 ? N1 C2 1.360(10) . ? N1 N2 1.374(8) . ? N2 C4 1.332(9) . ? N2 C6 1.464(9) . ? N3 C8 1.351(9) . ? N3 N4 1.370(8) . ? N3 C6 1.503(9) . ? N4 C10 1.308(9) . ? C1 C2 1.470(12) . ? C1 H5A 0.9600 . ? C1 H5B 0.9600 . ? C1 H5C 0.9600 . ? C2 C3 1.376(12) . ? C3 C4 1.373(11) . ? C3 H3 0.9300 . ? C4 C5 1.507(12) . ? C5 H1A 0.9600 . ? C5 H1B 0.9600 . ? C5 H1C 0.9600 . ? C6 H6 0.9800 . ? C7 C8 1.491(10) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.380(10) . ? C9 C10 1.404(10) . ? C9 H9 0.9300 . ? C10 C11 1.484(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.546(13) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 C12 Zn1 O1 121.9(4) . . ? C12 Zn1 N1 119.0(3) . . ? O1 Zn1 N1 106.2(2) . . ? C12 Zn1 N4 120.4(4) . . ? O1 Zn1 N4 97.0(2) . . ? N1 Zn1 N4 84.8(2) . . ? O1 Zn2 C6 105.57(19) . 7_665 ? O1 Zn2 C6 105.57(19) . . ? C6 Zn2 C6 113.07(16) 7_665 . ? O1 Zn2 C6 105.57(19) . 10_646 ? C6 Zn2 C6 113.07(16) 7_665 10_646 ? C6 Zn2 C6 113.07(16) . 10_646 ? Zn1 O1 Zn1 112.54(19) 7_665 . ? Zn1 O1 Zn1 112.54(19) 7_665 10_646 ? Zn1 O1 Zn1 112.54(19) . 10_646 ? Zn1 O1 Zn2 106.2(2) 7_665 . ? Zn1 O1 Zn2 106.2(2) . . ? Zn1 O1 Zn2 106.2(2) 10_646 . ? C2 N1 N2 104.4(6) . . ? C2 N1 Zn1 135.4(5) . . ? N2 N1 Zn1 118.5(4) . . ? C4 N2 N1 111.3(6) . . ? C4 N2 C6 131.2(6) . . ? N1 N2 C6 117.4(5) . . ? C8 N3 N4 111.3(6) . . ? C8 N3 C6 130.2(6) . . ? N4 N3 C6 118.4(5) . . ? C10 N4 N3 106.7(6) . . ? C10 N4 Zn1 135.3(6) . . ? N3 N4 Zn1 117.9(4) . . ? C2 C1 H5A 109.5 . . ? C2 C1 H5B 109.5 . . ? H5A C1 H5B 109.5 . . ? C2 C1 H5C 109.5 . . ? H5A C1 H5C 109.5 . . ? H5B C1 H5C 109.5 . . ? N1 C2 C3 110.5(7) . . ? N1 C2 C1 119.9(8) . . ? C3 C2 C1 129.6(8) . . ? C4 C3 C2 106.1(6) . . ? C4 C3 H3 126.9 . . ? C2 C3 H3 126.9 . . ? N2 C4 C3 107.6(6) . . ? N2 C4 C5 122.7(7) . . ? C3 C4 C5 129.6(7) . . ? C4 C5 H1A 109.5 . . ? C4 C5 H1B 109.5 . . ? H1A C5 H1B 109.5 . . ? C4 C5 H1C 109.5 . . ? H1A C5 H1C 109.5 . . ? H1B C5 H1C 109.5 . . ? N2 C6 N3 106.4(5) . . ? N2 C6 Zn2 113.3(4) . . ? N3 C6 Zn2 112.9(5) . . ? N2 C6 H6 108.0 . . ? N3 C6 H6 108.0 . . ? Zn2 C6 H6 108.0 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 105.4(6) . . ? N3 C8 C7 122.5(6) . . ? C9 C8 C7 132.1(7) . . ? C8 C9 C10 107.0(7) . . ? C8 C9 H9 126.5 . . ? C10 C9 H9 126.5 . . ? N4 C10 C9 109.5(7) . . ? N4 C10 C11 121.8(7) . . ? C9 C10 C11 128.6(7) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 Zn1 118.9(8) . . ? C13 C12 H12A 107.6 . . ? Zn1 C12 H12A 107.6 . . ? C13 C12 H12B 107.6 . . ? Zn1 C12 H12B 107.6 . . ? H12A C12 H12B 107.0 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.373 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.063 #===END