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 ;Preparation and characterization of asymmetric ?-alkoxy dipyrrin ligands and their metal complexes ; _publ_contact_author_name 'Prof. Seth Cohen' _publ_contact_author_email SCOHEN@UCSD.EDU loop_ _publ_author_name 'Seth Cohen' 'Sara R. Halper' 'Jay Stork' # Attachment 'CompiledCIF.cif' data_1234661 _database_code_depnum_ccdc_archive 'CCDC 624663' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common alpha-OMe-4-cydpm _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 N3 O' _chemical_formula_sum 'C17 H13 N3 O' _chemical_formula_weight 275.30 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8386(9) _cell_length_b 9.3207(9) _cell_length_c 10.0246(10) _cell_angle_alpha 63.7840(10) _cell_angle_beta 68.1580(10) _cell_angle_gamma 78.077(2) _cell_volume 686.82(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3008 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97582 _exptl_absorpt_correction_T_max 0.98872 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5831 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2774 _reflns_number_gt 2503 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.054 (Bruker, 2003)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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. The position of Atom H1N was allowed to refine, but its thermal parameter was treated with a riding model. All other H atoms were located in a difference map, placed in calculated positions, and treated with a riding model. ; _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^)+(0.0697P)^2^+0.2328P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2774 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1179 _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 C1 C 0.71105(17) 0.81867(16) 0.03732(16) 0.0219(3) Uani 1 1 d . . . H1 H 0.7713 0.9127 -0.0192 0.026 Uiso 1 1 calc R . . C2 C 0.55748(18) 0.80371(17) 0.14619(16) 0.0234(3) Uani 1 1 d . . . H2 H 0.4929 0.8849 0.1784 0.028 Uiso 1 1 calc R . . C3 C 0.51404(17) 0.64603(17) 0.20071(16) 0.0219(3) Uani 1 1 d . . . H3 H 0.4147 0.6009 0.2772 0.026 Uiso 1 1 calc R . . C4 C 0.64263(16) 0.56786(16) 0.12267(15) 0.0186(3) Uani 1 1 d . . . C5 C 0.65522(16) 0.40876(16) 0.12675(15) 0.0182(3) Uani 1 1 d . . . C6 C 0.77021(16) 0.36135(16) 0.01590(16) 0.0192(3) Uani 1 1 d . . . C7 C 0.80007(16) 0.20308(16) 0.01273(17) 0.0221(3) Uani 1 1 d . . . H7 H 0.7442 0.1095 0.0903 0.026 Uiso 1 1 calc R . . C8 C 0.92165(17) 0.21445(17) -0.12068(17) 0.0248(3) Uani 1 1 d . . . H8 H 0.9692 0.1318 -0.1570 0.030 Uiso 1 1 calc R . . C9 C 0.96425(16) 0.38062(17) -0.19696(16) 0.0225(3) Uani 1 1 d . . . C10 C 1.10401(19) 0.60318(19) -0.40303(19) 0.0329(4) Uani 1 1 d . . . H10A H 1.0024 0.6634 -0.4178 0.049 Uiso 1 1 calc R . . H10B H 1.1909 0.6325 -0.5046 0.049 Uiso 1 1 calc R . . H10C H 1.1347 0.6286 -0.3318 0.049 Uiso 1 1 calc R . . C11 C 0.52784(16) 0.29768(15) 0.25484(16) 0.0186(3) Uani 1 1 d . . . C12 C 0.44307(16) 0.21596(16) 0.21871(15) 0.0197(3) Uani 1 1 d . . . H12 H 0.4709 0.2282 0.1133 0.024 Uiso 1 1 calc R . . C13 C 0.31939(16) 0.11764(16) 0.33412(16) 0.0210(3) Uani 1 1 d . . . H13 H 0.2629 0.0624 0.3082 0.025 Uiso 1 1 calc R . . C14 C 0.27797(16) 0.09992(16) 0.48889(16) 0.0198(3) Uani 1 1 d . . . C15 C 0.36130(17) 0.18014(16) 0.52744(16) 0.0209(3) Uani 1 1 d . . . H15 H 0.3331 0.1677 0.6330 0.025 Uiso 1 1 calc R . . C16 C 0.48509(16) 0.27785(16) 0.41116(16) 0.0206(3) Uani 1 1 d . . . H16 H 0.5419 0.3323 0.4375 0.025 Uiso 1 1 calc R . . C17 C 0.14568(17) 0.00070(16) 0.60783(16) 0.0223(3) Uani 1 1 d . . . N1 N 0.76175(14) 0.67682(14) 0.02438(14) 0.0199(3) Uani 1 1 d . . . H1N H 0.850(2) 0.6572(19) -0.050(2) 0.024 Uiso 1 1 d . . . N2 N 0.88067(14) 0.46727(14) -0.11954(13) 0.0208(3) Uani 1 1 d . . . N3 N 0.03927(15) -0.07752(15) 0.70243(15) 0.0280(3) Uani 1 1 d . . . O1 O 1.08048(12) 0.43439(13) -0.33696(12) 0.0285(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0259(7) 0.0195(6) 0.0219(7) -0.0084(5) -0.0065(6) -0.0064(5) C2 0.0274(7) 0.0222(7) 0.0218(7) -0.0114(6) -0.0061(6) -0.0013(6) C3 0.0222(7) 0.0222(7) 0.0183(7) -0.0073(5) -0.0029(5) -0.0043(5) C4 0.0189(6) 0.0193(6) 0.0157(6) -0.0052(5) -0.0032(5) -0.0059(5) C5 0.0180(6) 0.0192(6) 0.0173(6) -0.0066(5) -0.0052(5) -0.0034(5) C6 0.0180(6) 0.0193(6) 0.0190(7) -0.0063(5) -0.0045(5) -0.0040(5) C7 0.0212(7) 0.0206(7) 0.0241(7) -0.0089(6) -0.0056(6) -0.0038(5) C8 0.0229(7) 0.0246(7) 0.0286(8) -0.0153(6) -0.0043(6) -0.0014(6) C9 0.0178(6) 0.0272(7) 0.0207(7) -0.0105(6) -0.0018(5) -0.0041(5) C10 0.0268(8) 0.0314(8) 0.0279(8) -0.0092(7) 0.0060(6) -0.0105(6) C11 0.0168(6) 0.0167(6) 0.0184(7) -0.0051(5) -0.0034(5) -0.0016(5) C12 0.0192(6) 0.0222(7) 0.0158(6) -0.0069(5) -0.0036(5) -0.0029(5) C13 0.0196(6) 0.0218(7) 0.0214(7) -0.0085(6) -0.0051(6) -0.0041(5) C14 0.0167(6) 0.0192(6) 0.0192(7) -0.0059(5) -0.0023(5) -0.0028(5) C15 0.0218(7) 0.0214(7) 0.0167(7) -0.0068(5) -0.0033(5) -0.0028(5) C16 0.0212(7) 0.0208(7) 0.0206(7) -0.0087(5) -0.0055(5) -0.0039(5) C17 0.0219(7) 0.0246(7) 0.0211(7) -0.0108(6) -0.0046(6) -0.0033(6) N1 0.0177(6) 0.0208(6) 0.0198(6) -0.0081(5) -0.0023(5) -0.0055(5) N2 0.0178(6) 0.0214(6) 0.0194(6) -0.0073(5) -0.0009(5) -0.0050(4) N3 0.0256(6) 0.0319(7) 0.0229(6) -0.0089(5) -0.0011(5) -0.0120(5) O1 0.0232(5) 0.0301(6) 0.0254(6) -0.0136(5) 0.0055(4) -0.0068(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 C1 N1 1.3524(18) . ? C1 C2 1.376(2) . ? C1 H1 0.9500 . ? C2 C3 1.4048(19) . ? C2 H2 0.9500 . ? C3 C4 1.3908(19) . ? C3 H3 0.9500 . ? C4 N1 1.3771(17) . ? C4 C5 1.4474(19) . ? C5 C6 1.3679(19) . ? C5 C11 1.4898(18) . ? C6 N2 1.4138(17) . ? C6 C7 1.4564(19) . ? C7 C8 1.344(2) . ? C7 H7 0.9500 . ? C8 C9 1.451(2) . ? C8 H8 0.9500 . ? C9 N2 1.2966(18) . ? C9 O1 1.3397(17) . ? C10 O1 1.4384(18) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3979(19) . ? C11 C16 1.4018(19) . ? C12 C13 1.3819(19) . ? C12 H12 0.9500 . ? C13 C14 1.3944(19) . ? C13 H13 0.9500 . ? C14 C15 1.3948(19) . ? C14 C17 1.4420(18) . ? C15 C16 1.3820(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N3 1.1507(18) . ? N1 H1N 0.907(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.46(12) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.19(13) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.71(12) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? N1 C4 C3 106.70(12) . . ? N1 C4 C5 123.13(12) . . ? C3 C4 C5 130.01(12) . . ? C6 C5 C4 123.44(12) . . ? C6 C5 C11 120.02(12) . . ? C4 C5 C11 116.43(11) . . ? C5 C6 N2 122.75(12) . . ? C5 C6 C7 128.16(13) . . ? N2 C6 C7 109.09(11) . . ? C8 C7 C6 107.05(12) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 104.84(12) . . ? C7 C8 H8 127.6 . . ? C9 C8 H8 127.6 . . ? N2 C9 O1 124.95(13) . . ? N2 C9 C8 114.58(12) . . ? O1 C9 C8 120.46(13) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.64(12) . . ? C12 C11 C5 119.70(12) . . ? C16 C11 C5 121.60(12) . . ? C13 C12 C11 120.97(12) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.61(12) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.31(12) . . ? C13 C14 C17 119.24(12) . . ? C15 C14 C17 120.43(12) . . ? C16 C15 C14 119.61(12) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 120.86(12) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? N3 C17 C14 179.48(17) . . ? C1 N1 C4 109.92(12) . . ? C1 N1 H1N 127.2(10) . . ? C4 N1 H1N 121.8(10) . . ? C9 N2 C6 104.41(11) . . ? C9 O1 C10 114.64(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.12(16) . . . . ? C1 C2 C3 C4 -0.34(16) . . . . ? C2 C3 C4 N1 0.66(15) . . . . ? C2 C3 C4 C5 -174.83(13) . . . . ? N1 C4 C5 C6 -12.2(2) . . . . ? C3 C4 C5 C6 162.61(14) . . . . ? N1 C4 C5 C11 171.55(11) . . . . ? C3 C4 C5 C11 -13.6(2) . . . . ? C4 C5 C6 N2 -4.6(2) . . . . ? C11 C5 C6 N2 171.48(11) . . . . ? C4 C5 C6 C7 176.23(13) . . . . ? C11 C5 C6 C7 -7.7(2) . . . . ? C5 C6 C7 C8 178.23(14) . . . . ? N2 C6 C7 C8 -1.03(15) . . . . ? C6 C7 C8 C9 0.08(15) . . . . ? C7 C8 C9 N2 1.02(17) . . . . ? C7 C8 C9 O1 -178.34(13) . . . . ? C6 C5 C11 C12 -47.17(18) . . . . ? C4 C5 C11 C12 129.18(13) . . . . ? C6 C5 C11 C16 135.69(14) . . . . ? C4 C5 C11 C16 -47.95(17) . . . . ? C16 C11 C12 C13 0.09(19) . . . . ? C5 C11 C12 C13 -177.13(12) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C12 C13 C14 C17 178.25(12) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C17 C14 C15 C16 -178.40(12) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C5 C11 C16 C15 176.90(12) . . . . ? C13 C14 C17 N3 -84(17) . . . . ? C15 C14 C17 N3 95(17) . . . . ? C2 C1 N1 C4 0.55(15) . . . . ? C3 C4 N1 C1 -0.75(15) . . . . ? C5 C4 N1 C1 175.12(12) . . . . ? O1 C9 N2 C6 177.71(13) . . . . ? C8 C9 N2 C6 -1.62(16) . . . . ? C5 C6 N2 C9 -177.71(13) . . . . ? C7 C6 N2 C9 1.59(14) . . . . ? N2 C9 O1 C10 -2.6(2) . . . . ? C8 C9 O1 C10 176.69(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N2 0.907(17) 2.108(16) 2.7412(16) 126.0(14) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.293 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.059 #===END data_1234728 _database_code_depnum_ccdc_archive 'CCDC 624664' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Zn(alpha-OMe-4-mecdpm)!2$) _chemical_melting_point ? _chemical_formula_moiety 'C36 H30 N4 O6 Zn' _chemical_formula_sum 'C36 H30 N4 O6 Zn' _chemical_formula_weight 680.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9083(7) _cell_length_b 11.9234(7) _cell_length_c 12.0192(7) _cell_angle_alpha 69.4810(10) _cell_angle_beta 88.6430(10) _cell_angle_gamma 78.7560(10) _cell_volume 1565.77(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8979 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7302 _exptl_absorpt_correction_T_max 0.8845 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13652 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5708 _reflns_number_gt 5474 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.054 (Bruker, 2003)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All H atoms were located in a difference map, placed in calculated positions, and treated with a riding model. ; _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^)+(0.0379P)^2^+1.1121P] 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 5708 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.79302(14) 0.68571(15) 0.55614(15) 0.0194(3) Uani 1 1 d . . . H1 H 0.7962 0.7068 0.6233 0.023 Uiso 1 1 calc R . . C2 C 0.88893(14) 0.64435(16) 0.50166(16) 0.0222(4) Uani 1 1 d . . . H2 H 0.9654 0.6322 0.5258 0.027 Uiso 1 1 calc R . . C3 C 0.84762(14) 0.62507(15) 0.40459(15) 0.0200(3) Uani 1 1 d . . . H3 H 0.8914 0.5987 0.3500 0.024 Uiso 1 1 calc R . . C4 C 0.72700(14) 0.65275(14) 0.40374(14) 0.0168(3) Uani 1 1 d . . . C5 C 0.64914(14) 0.63318(14) 0.32758(14) 0.0167(3) Uani 1 1 d . . . C6 C 0.53476(14) 0.63069(14) 0.34542(14) 0.0173(3) Uani 1 1 d . . . C7 C 0.45392(15) 0.60999(15) 0.27197(15) 0.0212(3) Uani 1 1 d . . . H7 H 0.4693 0.5931 0.2026 0.025 Uiso 1 1 calc R . . C8 C 0.35050(15) 0.61943(16) 0.32206(15) 0.0225(4) Uani 1 1 d . . . H8 H 0.2819 0.6094 0.2951 0.027 Uiso 1 1 calc R . . C9 C 0.36988(14) 0.64798(14) 0.42506(15) 0.0178(3) Uani 1 1 d . . . C10 C 0.17613(15) 0.69403(19) 0.46828(18) 0.0306(4) Uani 1 1 d . . . H10A H 0.1600 0.7603 0.3934 0.046 Uiso 1 1 calc R . . H10B H 0.1302 0.7148 0.5276 0.046 Uiso 1 1 calc R . . H10C H 0.1584 0.6218 0.4607 0.046 Uiso 1 1 calc R . . C11 C 0.69913(13) 0.61454(15) 0.21852(14) 0.0171(3) Uani 1 1 d . . . C12 C 0.71033(14) 0.50351(15) 0.20076(15) 0.0194(3) Uani 1 1 d . . . H12 H 0.6827 0.4393 0.2559 0.023 Uiso 1 1 calc R . . C13 C 0.76264(14) 0.48855(15) 0.10093(15) 0.0191(3) Uani 1 1 d . . . H13 H 0.7716 0.4137 0.0904 0.023 Uiso 1 1 calc R . . C14 C 0.80177(14) 0.58517(15) 0.01651(14) 0.0174(3) Uani 1 1 d . . . C15 C 0.78698(14) 0.69772(15) 0.03183(15) 0.0190(3) Uani 1 1 d . . . H15 H 0.8106 0.7633 -0.0255 0.023 Uiso 1 1 calc R . . C16 C 0.73712(14) 0.71143(15) 0.13255(15) 0.0192(3) Uani 1 1 d . . . H16 H 0.7288 0.7862 0.1432 0.023 Uiso 1 1 calc R . . C17 C 0.86201(14) 0.57288(15) -0.08957(14) 0.0182(3) Uani 1 1 d . . . C18 C 0.94567(15) 0.43794(16) -0.18587(15) 0.0232(4) Uani 1 1 d . . . H18A H 0.8980 0.4764 -0.2576 0.035 Uiso 1 1 calc R . . H18B H 0.9676 0.3519 -0.1708 0.035 Uiso 1 1 calc R . . H18C H 1.0130 0.4727 -0.1945 0.035 Uiso 1 1 calc R . . C19 C 0.55956(14) 0.64293(15) 0.80438(15) 0.0199(3) Uani 1 1 d . . . H19 H 0.6287 0.5892 0.8085 0.024 Uiso 1 1 calc R . . C20 C 0.50221(15) 0.65499(16) 0.90300(15) 0.0219(4) Uani 1 1 d . . . H20 H 0.5253 0.6126 0.9826 0.026 Uiso 1 1 calc R . . C21 C 0.40360(15) 0.74319(15) 0.85852(15) 0.0205(3) Uani 1 1 d . . . H21 H 0.3472 0.7706 0.9031 0.025 Uiso 1 1 calc R . . C22 C 0.40457(14) 0.78354(15) 0.73373(15) 0.0171(3) Uani 1 1 d . . . C23 C 0.32411(14) 0.87947(14) 0.65108(15) 0.0172(3) Uani 1 1 d . . . C24 C 0.33583(14) 0.93332(15) 0.53092(15) 0.0181(3) Uani 1 1 d . . . C25 C 0.25378(15) 1.02656(15) 0.44539(16) 0.0220(4) Uani 1 1 d . . . H25 H 0.1826 1.0642 0.4618 0.026 Uiso 1 1 calc R . . C26 C 0.29857(15) 1.04983(16) 0.33665(16) 0.0238(4) Uani 1 1 d . . . H26 H 0.2653 1.1062 0.2645 0.029 Uiso 1 1 calc R . . C27 C 0.40831(14) 0.96889(15) 0.35699(15) 0.0195(3) Uani 1 1 d . . . C28 C 0.45290(17) 1.02137(19) 0.15545(16) 0.0300(4) Uani 1 1 d . . . H28A H 0.3850 0.9997 0.1343 0.045 Uiso 1 1 calc R . . H28B H 0.5140 1.0032 0.1070 0.045 Uiso 1 1 calc R . . H28C H 0.4380 1.1071 0.1428 0.045 Uiso 1 1 calc R . . C29 C 0.21581(14) 0.92426(15) 0.70178(14) 0.0176(3) Uani 1 1 d . . . C30 C 0.19371(14) 1.03873(15) 0.71373(15) 0.0196(3) Uani 1 1 d . . . H30 H 0.2458 1.0902 0.6875 0.023 Uiso 1 1 calc R . . C31 C 0.09422(14) 1.07605(15) 0.76468(15) 0.0196(3) Uani 1 1 d . . . H31 H 0.0805 1.1520 0.7734 0.023 Uiso 1 1 calc R . . C32 C 0.01478(14) 1.00050(15) 0.80280(14) 0.0181(3) Uani 1 1 d . . . C33 C 0.03495(14) 0.88707(15) 0.78819(15) 0.0202(3) Uani 1 1 d . . . H33 H -0.0187 0.8370 0.8114 0.024 Uiso 1 1 calc R . . C34 C 0.13494(15) 0.84970(15) 0.73905(15) 0.0201(3) Uani 1 1 d . . . H34 H 0.1486 0.7737 0.7306 0.024 Uiso 1 1 calc R . . C35 C -0.09041(14) 1.03307(15) 0.86338(14) 0.0191(3) Uani 1 1 d . . . C36 C -0.19744(15) 1.17352(16) 0.94083(16) 0.0246(4) Uani 1 1 d . . . H36A H -0.2662 1.1840 0.8951 0.037 Uiso 1 1 calc R . . H36B H -0.1944 1.2484 0.9528 0.037 Uiso 1 1 calc R . . H36C H -0.1972 1.1096 1.0165 0.037 Uiso 1 1 calc R . . N1 N 0.69551(11) 0.69102(12) 0.49888(12) 0.0161(3) Uani 1 1 d . . . N2 N 0.47739(11) 0.65235(12) 0.44121(12) 0.0158(3) Uani 1 1 d . . . N3 N 0.50223(11) 0.71886(12) 0.70209(12) 0.0165(3) Uani 1 1 d . . . N4 N 0.43161(12) 0.90128(12) 0.47008(12) 0.0169(3) Uani 1 1 d . . . O1 O 0.29511(10) 0.67198(11) 0.50275(11) 0.0221(3) Uani 1 1 d . . . O2 O 0.89025(11) 0.65600(11) -0.16890(10) 0.0249(3) Uani 1 1 d . . . O3 O 0.88300(11) 0.45727(11) -0.08750(11) 0.0238(3) Uani 1 1 d . . . O4 O 0.48546(11) 0.95261(11) 0.27870(10) 0.0242(3) Uani 1 1 d . . . O5 O -0.16100(10) 0.97025(11) 0.89767(12) 0.0270(3) Uani 1 1 d . . . O6 O -0.09879(10) 1.14121(11) 0.87765(11) 0.0236(3) Uani 1 1 d . . . Zn1 Zn 0.537013(15) 0.738518(16) 0.537171(16) 0.01547(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 C1 0.0189(8) 0.0201(8) 0.0193(8) -0.0069(7) 0.0006(7) -0.0042(7) C2 0.0134(8) 0.0257(9) 0.0259(9) -0.0073(7) 0.0018(7) -0.0038(7) C3 0.0176(8) 0.0201(8) 0.0217(8) -0.0075(7) 0.0071(7) -0.0026(7) C4 0.0174(8) 0.0148(8) 0.0175(8) -0.0054(6) 0.0050(6) -0.0027(6) C5 0.0191(8) 0.0121(7) 0.0170(8) -0.0040(6) 0.0030(6) -0.0011(6) C6 0.0198(8) 0.0145(8) 0.0171(8) -0.0057(6) 0.0021(6) -0.0018(6) C7 0.0242(9) 0.0220(9) 0.0187(8) -0.0084(7) 0.0010(7) -0.0055(7) C8 0.0190(8) 0.0267(9) 0.0232(9) -0.0090(7) -0.0015(7) -0.0073(7) C9 0.0164(8) 0.0155(8) 0.0200(8) -0.0044(6) 0.0028(6) -0.0034(6) C10 0.0154(8) 0.0399(11) 0.0371(11) -0.0153(9) 0.0045(8) -0.0043(8) C11 0.0147(7) 0.0201(8) 0.0167(8) -0.0073(6) 0.0021(6) -0.0022(6) C12 0.0215(8) 0.0173(8) 0.0181(8) -0.0044(6) 0.0036(7) -0.0048(7) C13 0.0212(8) 0.0167(8) 0.0202(8) -0.0082(7) 0.0024(7) -0.0027(7) C14 0.0164(8) 0.0192(8) 0.0164(8) -0.0066(6) 0.0005(6) -0.0022(6) C15 0.0205(8) 0.0171(8) 0.0177(8) -0.0038(6) 0.0026(6) -0.0042(6) C16 0.0211(8) 0.0162(8) 0.0213(8) -0.0085(7) 0.0030(7) -0.0029(6) C17 0.0163(8) 0.0210(8) 0.0181(8) -0.0078(7) -0.0008(6) -0.0034(6) C18 0.0255(9) 0.0251(9) 0.0212(9) -0.0119(7) 0.0079(7) -0.0039(7) C19 0.0179(8) 0.0189(8) 0.0224(8) -0.0078(7) 0.0003(7) -0.0016(7) C20 0.0243(9) 0.0228(9) 0.0166(8) -0.0055(7) 0.0007(7) -0.0030(7) C21 0.0211(8) 0.0221(8) 0.0198(8) -0.0096(7) 0.0063(7) -0.0043(7) C22 0.0167(8) 0.0172(8) 0.0202(8) -0.0094(7) 0.0048(6) -0.0048(6) C23 0.0170(8) 0.0156(8) 0.0219(8) -0.0097(7) 0.0040(6) -0.0042(6) C24 0.0185(8) 0.0157(8) 0.0219(8) -0.0096(7) 0.0035(7) -0.0022(6) C25 0.0211(8) 0.0187(8) 0.0250(9) -0.0087(7) 0.0018(7) 0.0003(7) C26 0.0276(9) 0.0200(8) 0.0201(8) -0.0050(7) -0.0003(7) -0.0001(7) C27 0.0225(8) 0.0177(8) 0.0197(8) -0.0077(7) 0.0047(7) -0.0056(7) C28 0.0328(10) 0.0397(11) 0.0172(9) -0.0075(8) 0.0054(8) -0.0116(9) C29 0.0175(8) 0.0180(8) 0.0157(8) -0.0058(6) 0.0015(6) -0.0005(6) C30 0.0199(8) 0.0179(8) 0.0218(8) -0.0074(7) 0.0052(7) -0.0054(7) C31 0.0225(8) 0.0143(8) 0.0220(8) -0.0078(7) 0.0041(7) -0.0018(6) C32 0.0173(8) 0.0182(8) 0.0176(8) -0.0064(6) 0.0025(6) -0.0011(6) C33 0.0193(8) 0.0192(8) 0.0227(8) -0.0072(7) 0.0039(7) -0.0057(7) C34 0.0222(8) 0.0158(8) 0.0234(8) -0.0088(7) 0.0036(7) -0.0029(7) C35 0.0189(8) 0.0181(8) 0.0176(8) -0.0051(6) -0.0005(6) 0.0003(7) C36 0.0230(9) 0.0228(9) 0.0270(9) -0.0105(7) 0.0096(7) -0.0002(7) N1 0.0156(6) 0.0163(7) 0.0172(7) -0.0069(5) 0.0026(5) -0.0030(5) N2 0.0153(6) 0.0150(7) 0.0173(7) -0.0062(5) 0.0031(5) -0.0028(5) N3 0.0154(6) 0.0178(7) 0.0170(7) -0.0075(5) 0.0023(5) -0.0024(5) N4 0.0182(7) 0.0146(7) 0.0180(7) -0.0063(5) 0.0040(5) -0.0027(5) O1 0.0150(6) 0.0277(6) 0.0251(6) -0.0115(5) 0.0049(5) -0.0046(5) O2 0.0342(7) 0.0246(6) 0.0190(6) -0.0090(5) 0.0088(5) -0.0117(5) O3 0.0309(7) 0.0195(6) 0.0222(6) -0.0097(5) 0.0114(5) -0.0044(5) O4 0.0267(6) 0.0256(6) 0.0181(6) -0.0066(5) 0.0060(5) -0.0030(5) O5 0.0222(6) 0.0245(6) 0.0380(7) -0.0141(6) 0.0125(6) -0.0085(5) O6 0.0227(6) 0.0205(6) 0.0302(7) -0.0132(5) 0.0120(5) -0.0039(5) Zn1 0.01374(11) 0.01708(11) 0.01650(11) -0.00798(8) 0.00311(7) -0.00158(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 C1 N1 1.343(2) . ? C1 C2 1.396(2) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.409(2) . ? C3 H3 0.9300 . ? C4 N1 1.391(2) . ? C4 C5 1.423(2) . ? C5 C6 1.378(2) . ? C5 C11 1.496(2) . ? C6 N2 1.401(2) . ? C6 C7 1.433(2) . ? C7 C8 1.360(2) . ? C7 H7 0.9300 . ? C8 C9 1.429(2) . ? C8 H8 0.9300 . ? C9 N2 1.313(2) . ? C9 O1 1.340(2) . ? C10 O1 1.433(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.394(2) . ? C11 C16 1.397(2) . ? C12 C13 1.390(2) . ? C12 H12 0.9300 . ? C13 C14 1.393(2) . ? C13 H13 0.9300 . ? C14 C15 1.395(2) . ? C14 C17 1.486(2) . ? C15 C16 1.383(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O2 1.207(2) . ? C17 O3 1.344(2) . ? C18 O3 1.4458(19) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N3 1.347(2) . ? C19 C20 1.391(2) . ? C19 H19 0.9300 . ? C20 C21 1.387(2) . ? C20 H20 0.9300 . ? C21 C22 1.406(2) . ? C21 H21 0.9300 . ? C22 N3 1.388(2) . ? C22 C23 1.426(2) . ? C23 C24 1.376(2) . ? C23 C29 1.497(2) . ? C24 N4 1.403(2) . ? C24 C25 1.439(2) . ? C25 C26 1.357(3) . ? C25 H25 0.9300 . ? C26 C27 1.434(2) . ? C26 H26 0.9300 . ? C27 N4 1.318(2) . ? C27 O4 1.336(2) . ? C28 O4 1.438(2) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.396(2) . ? C29 C34 1.397(2) . ? C30 C31 1.388(2) . ? C30 H30 0.9300 . ? C31 C32 1.392(2) . ? C31 H31 0.9300 . ? C32 C33 1.398(2) . ? C32 C35 1.488(2) . ? C33 C34 1.382(2) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 O5 1.204(2) . ? C35 O6 1.344(2) . ? C36 O6 1.4462(19) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? N1 Zn1 1.9543(13) . ? N2 Zn1 2.0110(13) . ? N3 Zn1 1.9567(13) . ? N4 Zn1 1.9982(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 111.18(15) . . ? N1 C1 H1 124.4 . . ? C2 C1 H1 124.4 . . ? C3 C2 C1 106.30(15) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? C2 C3 C4 107.34(14) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C3 108.36(14) . . ? N1 C4 C5 124.72(14) . . ? C3 C4 C5 126.60(15) . . ? C6 C5 C4 126.16(15) . . ? C6 C5 C11 118.62(14) . . ? C4 C5 C11 115.22(14) . . ? C5 C6 N2 123.74(15) . . ? C5 C6 C7 127.96(15) . . ? N2 C6 C7 108.28(14) . . ? C8 C7 C6 107.61(15) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 105.24(15) . . ? C7 C8 H8 127.4 . . ? C9 C8 H8 127.4 . . ? N2 C9 O1 117.80(15) . . ? N2 C9 C8 112.74(15) . . ? O1 C9 C8 129.45(15) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.12(15) . . ? C12 C11 C5 122.21(14) . . ? C16 C11 C5 118.67(14) . . ? C13 C12 C11 120.15(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.29(15) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 119.70(15) . . ? C13 C14 C17 122.51(15) . . ? C15 C14 C17 117.77(15) . . ? C16 C15 C14 119.80(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 120.88(15) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? O2 C17 O3 123.04(15) . . ? O2 C17 C14 124.67(15) . . ? O3 C17 C14 112.29(14) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C20 111.46(15) . . ? N3 C19 H19 124.3 . . ? C20 C19 H19 124.3 . . ? C21 C20 C19 106.01(15) . . ? C21 C20 H20 127.0 . . ? C19 C20 H20 127.0 . . ? C20 C21 C22 107.45(15) . . ? C20 C21 H21 126.3 . . ? C22 C21 H21 126.3 . . ? N3 C22 C21 108.53(14) . . ? N3 C22 C23 124.37(14) . . ? C21 C22 C23 127.00(15) . . ? C24 C23 C22 126.73(15) . . ? C24 C23 C29 117.50(14) . . ? C22 C23 C29 115.78(14) . . ? C23 C24 N4 124.38(15) . . ? C23 C24 C25 127.53(15) . . ? N4 C24 C25 108.05(14) . . ? C26 C25 C24 107.95(15) . . ? C26 C25 H25 126.0 . . ? C24 C25 H25 126.0 . . ? C25 C26 C27 105.16(15) . . ? C25 C26 H26 127.4 . . ? C27 C26 H26 127.4 . . ? N4 C27 O4 117.97(15) . . ? N4 C27 C26 112.72(15) . . ? O4 C27 C26 129.30(15) . . ? O4 C28 H28A 109.5 . . ? O4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C34 118.91(15) . . ? C30 C29 C23 121.61(15) . . ? C34 C29 C23 119.48(14) . . ? C31 C30 C29 120.25(15) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.39(15) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C31 C32 C33 119.63(15) . . ? C31 C32 C35 122.70(15) . . ? C33 C32 C35 117.63(15) . . ? C34 C33 C32 119.68(15) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C29 121.11(15) . . ? C33 C34 H34 119.4 . . ? C29 C34 H34 119.4 . . ? O5 C35 O6 122.57(15) . . ? O5 C35 C32 124.66(15) . . ? O6 C35 C32 112.76(14) . . ? O6 C36 H36A 109.5 . . ? O6 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O6 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C1 N1 C4 106.81(13) . . ? C1 N1 Zn1 128.97(11) . . ? C4 N1 Zn1 124.21(11) . . ? C9 N2 C6 106.10(13) . . ? C9 N2 Zn1 126.73(11) . . ? C6 N2 Zn1 122.83(11) . . ? C19 N3 C22 106.55(13) . . ? C19 N3 Zn1 130.10(11) . . ? C22 N3 Zn1 123.32(11) . . ? C27 N4 C24 106.11(14) . . ? C27 N4 Zn1 127.41(11) . . ? C24 N4 Zn1 121.10(11) . . ? C9 O1 C10 116.17(14) . . ? C17 O3 C18 115.15(13) . . ? C27 O4 C28 116.15(14) . . ? C35 O6 C36 114.34(13) . . ? N1 Zn1 N3 119.18(6) . . ? N1 Zn1 N4 128.28(6) . . ? N3 Zn1 N4 93.95(6) . . ? N1 Zn1 N2 92.57(5) . . ? N3 Zn1 N2 125.36(6) . . ? N4 Zn1 N2 99.11(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.9(2) . . . . ? C1 C2 C3 C4 -1.24(19) . . . . ? C2 C3 C4 N1 1.15(18) . . . . ? C2 C3 C4 C5 -172.61(16) . . . . ? N1 C4 C5 C6 -10.4(3) . . . . ? C3 C4 C5 C6 162.38(16) . . . . ? N1 C4 C5 C11 169.26(14) . . . . ? C3 C4 C5 C11 -17.9(2) . . . . ? C4 C5 C6 N2 2.6(3) . . . . ? C11 C5 C6 N2 -177.05(14) . . . . ? C4 C5 C6 C7 -179.23(16) . . . . ? C11 C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 C8 -178.15(17) . . . . ? N2 C6 C7 C8 0.23(19) . . . . ? C6 C7 C8 C9 0.94(19) . . . . ? C7 C8 C9 N2 -1.9(2) . . . . ? C7 C8 C9 O1 176.78(16) . . . . ? C6 C5 C11 C12 -66.7(2) . . . . ? C4 C5 C11 C12 113.56(17) . . . . ? C6 C5 C11 C16 114.11(18) . . . . ? C4 C5 C11 C16 -65.6(2) . . . . ? C16 C11 C12 C13 2.4(2) . . . . ? C5 C11 C12 C13 -176.70(15) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? C12 C13 C14 C15 -0.8(2) . . . . ? C12 C13 C14 C17 177.75(15) . . . . ? C13 C14 C15 C16 2.2(2) . . . . ? C17 C14 C15 C16 -176.43(15) . . . . ? C14 C15 C16 C11 -1.3(3) . . . . ? C12 C11 C16 C15 -1.0(2) . . . . ? C5 C11 C16 C15 178.13(15) . . . . ? C13 C14 C17 O2 174.64(16) . . . . ? C15 C14 C17 O2 -6.8(2) . . . . ? C13 C14 C17 O3 -5.9(2) . . . . ? C15 C14 C17 O3 172.67(14) . . . . ? N3 C19 C20 C21 0.3(2) . . . . ? C19 C20 C21 C22 -0.77(19) . . . . ? C20 C21 C22 N3 1.01(19) . . . . ? C20 C21 C22 C23 -175.44(16) . . . . ? N3 C22 C23 C24 -8.5(3) . . . . ? C21 C22 C23 C24 167.46(17) . . . . ? N3 C22 C23 C29 170.97(15) . . . . ? C21 C22 C23 C29 -13.1(2) . . . . ? C22 C23 C24 N4 -0.3(3) . . . . ? C29 C23 C24 N4 -179.67(14) . . . . ? C22 C23 C24 C25 177.21(16) . . . . ? C29 C23 C24 C25 -2.2(3) . . . . ? C23 C24 C25 C26 -177.75(17) . . . . ? N4 C24 C25 C26 0.05(19) . . . . ? C24 C25 C26 C27 0.51(19) . . . . ? C25 C26 C27 N4 -1.0(2) . . . . ? C25 C26 C27 O4 177.67(17) . . . . ? C24 C23 C29 C30 -71.9(2) . . . . ? C22 C23 C29 C30 108.66(18) . . . . ? C24 C23 C29 C34 108.65(18) . . . . ? C22 C23 C29 C34 -70.8(2) . . . . ? C34 C29 C30 C31 1.6(2) . . . . ? C23 C29 C30 C31 -177.88(16) . . . . ? C29 C30 C31 C32 -0.9(3) . . . . ? C30 C31 C32 C33 -0.8(3) . . . . ? C30 C31 C32 C35 176.90(16) . . . . ? C31 C32 C33 C34 1.7(3) . . . . ? C35 C32 C33 C34 -176.06(15) . . . . ? C32 C33 C34 C29 -1.0(3) . . . . ? C30 C29 C34 C33 -0.7(3) . . . . ? C23 C29 C34 C33 178.85(16) . . . . ? C31 C32 C35 O5 -179.95(17) . . . . ? C33 C32 C35 O5 -2.2(3) . . . . ? C31 C32 C35 O6 -0.6(2) . . . . ? C33 C32 C35 O6 177.12(14) . . . . ? C2 C1 N1 C4 -0.21(19) . . . . ? C2 C1 N1 Zn1 178.55(11) . . . . ? C3 C4 N1 C1 -0.58(18) . . . . ? C5 C4 N1 C1 173.33(15) . . . . ? C3 C4 N1 Zn1 -179.41(11) . . . . ? C5 C4 N1 Zn1 -5.5(2) . . . . ? O1 C9 N2 C6 -176.82(13) . . . . ? C8 C9 N2 C6 2.06(18) . . . . ? O1 C9 N2 Zn1 -20.0(2) . . . . ? C8 C9 N2 Zn1 158.89(11) . . . . ? C5 C6 N2 C9 177.07(15) . . . . ? C7 C6 N2 C9 -1.39(17) . . . . ? C5 C6 N2 Zn1 19.1(2) . . . . ? C7 C6 N2 Zn1 -159.35(11) . . . . ? C20 C19 N3 C22 0.36(19) . . . . ? C20 C19 N3 Zn1 -177.45(12) . . . . ? C21 C22 N3 C19 -0.84(18) . . . . ? C23 C22 N3 C19 175.73(15) . . . . ? C21 C22 N3 Zn1 177.15(11) . . . . ? C23 C22 N3 Zn1 -6.3(2) . . . . ? O4 C27 N4 C24 -177.82(14) . . . . ? C26 C27 N4 C24 0.99(19) . . . . ? O4 C27 N4 Zn1 -24.0(2) . . . . ? C26 C27 N4 Zn1 154.84(12) . . . . ? C23 C24 N4 C27 177.25(16) . . . . ? C25 C24 N4 C27 -0.64(18) . . . . ? C23 C24 N4 Zn1 21.4(2) . . . . ? C25 C24 N4 Zn1 -156.50(11) . . . . ? N2 C9 O1 C10 166.19(15) . . . . ? C8 C9 O1 C10 -12.5(2) . . . . ? O2 C17 O3 C18 1.9(2) . . . . ? C14 C17 O3 C18 -177.59(14) . . . . ? N4 C27 O4 C28 175.39(15) . . . . ? C26 C27 O4 C28 -3.2(3) . . . . ? O5 C35 O6 C36 1.9(2) . . . . ? C32 C35 O6 C36 -177.45(14) . . . . ? C1 N1 Zn1 N3 -26.05(16) . . . . ? C4 N1 Zn1 N3 152.50(12) . . . . ? C1 N1 Zn1 N4 96.71(15) . . . . ? C4 N1 Zn1 N4 -84.73(14) . . . . ? C1 N1 Zn1 N2 -159.56(14) . . . . ? C4 N1 Zn1 N2 18.99(13) . . . . ? C19 N3 Zn1 N1 -24.27(16) . . . . ? C22 N3 Zn1 N1 158.24(12) . . . . ? C19 N3 Zn1 N4 -162.85(14) . . . . ? C22 N3 Zn1 N4 19.67(13) . . . . ? C19 N3 Zn1 N2 93.06(15) . . . . ? C22 N3 Zn1 N2 -84.42(13) . . . . ? C27 N4 Zn1 N1 50.38(16) . . . . ? C24 N4 Zn1 N1 -159.26(11) . . . . ? C27 N4 Zn1 N3 -177.01(14) . . . . ? C24 N4 Zn1 N3 -26.65(13) . . . . ? C27 N4 Zn1 N2 -50.25(14) . . . . ? C24 N4 Zn1 N2 100.11(12) . . . . ? C9 N2 Zn1 N1 -178.81(14) . . . . ? C6 N2 Zn1 N1 -25.55(13) . . . . ? C9 N2 Zn1 N3 52.12(15) . . . . ? C6 N2 Zn1 N3 -154.62(11) . . . . ? C9 N2 Zn1 N4 -49.37(14) . . . . ? C6 N2 Zn1 N4 103.89(12) . . . . ? 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 C1 H1 O2 0.93 2.58 3.404(2) 147.7 1_556 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.342 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.052