# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mir Wais Hosseini' _publ_contact_author_email HOSSEINI@CHIMIE.U-STRASBG.FR _publ_section_title ; Molecular tectonics: control of pore size and polarity in 3-D hexagonal coordination networks based on porphyrins and Zinc cation ; loop_ _publ_author_name 'Mir Wais Hosseini' 'Veronique Bulach' 'Elisabeth Kuhn' # Attachment 'Revised_dehydrated_12-Zn.cif' data_e1310a _database_code_depnum_ccdc_archive 'CCDC 696294' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H24 N8 Zn' _chemical_formula_weight 730.08 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 32.9851(7) _cell_length_b 32.9851(7) _cell_length_c 9.0387(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8516.7(5) _cell_formula_units_Z 9 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2602 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 20.97 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3366 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8462 _exptl_absorpt_correction_T_max 0.9035 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26849 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4342 _reflns_number_gt 2864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0790P)^2^+7.8233P] 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 4342 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1079 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.0000 0.0000 0.02711(19) Uani 1 2 d S . . N1 N 0.53288(9) -0.00281(10) -0.1915(3) 0.0292(6) Uani 1 1 d . . . N2 N 0.55976(9) 0.05945(9) 0.0712(3) 0.0290(7) Uani 1 1 d . . . C1 C 0.51532(11) -0.03668(12) -0.2988(4) 0.0311(8) Uani 1 1 d . . . C2 C 0.55259(12) -0.03067(13) -0.3958(4) 0.0394(9) Uani 1 1 d . . . H2 H 0.5497 -0.0492 -0.4800 0.047 Uiso 1 1 calc R . . C3 C 0.59243(13) 0.00636(14) -0.3442(4) 0.0417(10) Uani 1 1 d . . . H3 H 0.6228 0.0187 -0.3857 0.050 Uiso 1 1 calc R . . C4 C 0.58050(11) 0.02369(12) -0.2151(4) 0.0318(8) Uani 1 1 d . . . C5 C 0.61201(11) 0.06045(12) -0.1244(4) 0.0323(8) Uani 1 1 d . . . C6 C 0.60250(11) 0.07704(12) 0.0066(4) 0.0297(8) Uani 1 1 d . . . C7 C 0.63740(12) 0.11434(13) 0.0958(4) 0.0384(9) Uani 1 1 d . . . H7 H 0.6698 0.1329 0.0741 0.046 Uiso 1 1 calc R . . C8 C 0.61515(12) 0.11784(13) 0.2161(4) 0.0397(9) Uani 1 1 d . . . H8 H 0.6291 0.1392 0.2958 0.048 Uiso 1 1 calc R . . C9 C 0.56604(11) 0.08316(12) 0.2016(4) 0.0305(8) Uani 1 1 d . . . C10 C 0.53143(12) 0.07373(12) 0.3068(4) 0.0308(8) Uani 1 1 d . . . C11 C 0.66223(11) 0.08467(12) -0.1702(4) 0.0323(8) Uani 1 1 d . . . C12 C 0.69349(12) 0.07380(13) -0.1031(4) 0.0377(9) Uani 1 1 d . . . H12 H 0.6828 0.0495 -0.0317 0.045 Uiso 1 1 calc R . . C13 C 0.43202(13) 0.02521(13) -0.1922(4) 0.0362(9) Uani 1 1 d . . . H13 H 0.4244 -0.0035 -0.2396 0.043 Uiso 1 1 calc R . . N3 N 0.46627(10) 0.04247(11) -0.0922(3) 0.0372(7) Uani 1 1 d . . . C14 C 0.47625(14) 0.08276(13) -0.0272(5) 0.0427(10) Uani 1 1 d . . . H14 H 0.5006 0.0956 0.0445 0.051 Uiso 1 1 calc R . . C15 C 0.67979(13) 0.11970(14) -0.2745(4) 0.0411(9) Uani 1 1 d . . . H15 H 0.6595 0.1278 -0.3244 0.049 Uiso 1 1 calc R . . C16 C 0.54505(12) 0.10481(12) 0.4402(4) 0.0333(8) Uani 1 1 d . . . C17 C 0.56029(14) 0.15242(14) 0.4276(5) 0.0470(10) Uani 1 1 d . . . H17 H 0.5624 0.1658 0.3328 0.056 Uiso 1 1 calc R . . C18 C 0.57242(17) 0.18054(15) 0.5541(5) 0.0604(13) Uani 1 1 d . . . H18 H 0.5824 0.2129 0.5454 0.072 Uiso 1 1 calc R . . C19 C 0.56988(16) 0.16105(16) 0.6921(5) 0.0553(12) Uani 1 1 d . . . C20 C 0.55537(14) 0.11390(15) 0.7035(5) 0.0470(10) Uani 1 1 d . . . H20 H 0.5540 0.1006 0.7978 0.056 Uiso 1 1 calc R . . C21 C 0.54284(13) 0.08607(14) 0.5785(4) 0.0401(9) Uani 1 1 d . . . H21 H 0.5326 0.0537 0.5879 0.048 Uiso 1 1 calc R . . C22 C 0.5807(3) 0.1879(2) 0.8260(8) 0.1166(16) Uani 1 1 d . . . N4 N 0.5873(2) 0.20660(19) 0.9354(6) 0.1166(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0205(3) 0.0321(3) 0.0304(4) -0.0038(2) -0.0016(2) 0.0144(2) N1 0.0246(14) 0.0334(15) 0.0296(17) -0.0035(13) -0.0008(12) 0.0145(12) N2 0.0213(13) 0.0308(15) 0.0342(17) -0.0055(13) -0.0019(12) 0.0125(12) C1 0.0280(17) 0.0367(19) 0.029(2) -0.0020(15) 0.0002(15) 0.0168(15) C2 0.0329(19) 0.046(2) 0.040(2) -0.0101(18) 0.0062(17) 0.0201(17) C3 0.0294(19) 0.053(2) 0.042(2) -0.0109(19) 0.0055(17) 0.0206(18) C4 0.0254(17) 0.0370(19) 0.033(2) -0.0013(16) 0.0035(15) 0.0156(15) C5 0.0222(16) 0.0369(19) 0.035(2) 0.0010(16) 0.0015(15) 0.0128(15) C6 0.0215(16) 0.0346(18) 0.032(2) -0.0010(15) -0.0023(14) 0.0131(14) C7 0.0259(18) 0.039(2) 0.044(2) -0.0083(18) -0.0031(16) 0.0109(16) C8 0.0277(18) 0.040(2) 0.044(2) -0.0094(18) -0.0041(17) 0.0108(16) C9 0.0249(17) 0.0317(18) 0.033(2) -0.0049(15) -0.0032(15) 0.0124(15) C10 0.0287(17) 0.0330(18) 0.031(2) -0.0059(15) -0.0017(15) 0.0157(15) C11 0.0254(17) 0.0360(19) 0.031(2) -0.0058(16) 0.0006(15) 0.0118(15) C12 0.0271(18) 0.041(2) 0.039(2) 0.0093(17) 0.0066(16) 0.0128(16) C13 0.044(2) 0.041(2) 0.033(2) -0.0068(17) -0.0081(17) 0.0291(18) N3 0.0385(17) 0.0407(17) 0.0413(19) -0.0022(15) -0.0037(15) 0.0264(15) C14 0.045(2) 0.042(2) 0.047(3) -0.0033(19) -0.0070(19) 0.0269(19) C15 0.0317(19) 0.049(2) 0.044(2) 0.0052(19) 0.0012(17) 0.0217(18) C16 0.0308(18) 0.0349(19) 0.034(2) -0.0074(16) -0.0017(16) 0.0164(16) C17 0.054(2) 0.038(2) 0.043(3) -0.0003(19) 0.005(2) 0.0190(19) C18 0.075(3) 0.037(2) 0.054(3) -0.012(2) 0.005(2) 0.016(2) C19 0.053(3) 0.051(3) 0.050(3) -0.019(2) -0.001(2) 0.016(2) C20 0.042(2) 0.058(3) 0.039(2) -0.008(2) -0.0054(19) 0.024(2) C21 0.039(2) 0.041(2) 0.039(2) -0.0039(18) -0.0053(18) 0.0193(18) C22 0.148(4) 0.093(3) 0.073(3) -0.044(2) -0.005(3) 0.034(3) N4 0.148(4) 0.093(3) 0.073(3) -0.044(2) -0.005(3) 0.034(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.069(3) 10_655 ? Zn1 N2 2.069(3) . ? Zn1 N1 2.069(3) 10_655 ? Zn1 N1 2.069(3) . ? Zn1 N3 2.335(3) . ? Zn1 N3 2.335(3) 10_655 ? N1 C1 1.370(4) . ? N1 C4 1.380(4) . ? N2 C9 1.372(4) . ? N2 C6 1.359(4) . ? C1 C10 1.412(5) 10_655 ? C1 C2 1.441(5) . ? C2 C3 1.353(5) . ? C2 H2 0.9500 . ? C3 C4 1.438(5) . ? C3 H3 0.9500 . ? C4 C5 1.401(5) . ? C5 C6 1.404(5) . ? C5 C11 1.493(4) . ? C6 C7 1.440(5) . ? C7 C8 1.349(5) . ? C7 H7 0.9500 . ? C8 C9 1.448(5) . ? C8 H8 0.9500 . ? C9 C10 1.396(5) . ? C10 C1 1.412(5) 10_655 ? C10 C16 1.499(5) . ? C11 C15 1.375(5) . ? C11 C12 1.389(5) . ? C12 C13 1.378(5) 18_544 ? C12 H12 0.9500 . ? C13 N3 1.332(5) . ? C13 C12 1.377(5) 17_554 ? C13 H13 0.9500 . ? N3 C14 1.335(5) . ? C14 C15 1.374(5) 17_554 ? C14 H14 0.9500 . ? C15 C14 1.374(5) 18_544 ? C15 H15 0.9500 . ? C16 C21 1.380(5) . ? C16 C17 1.394(5) . ? C17 C18 1.399(6) . ? C17 H17 0.9500 . ? C18 C19 1.387(6) . ? C18 H18 0.9500 . ? C19 C20 1.384(6) . ? C19 C22 1.435(7) . ? C20 C21 1.382(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N4 1.127(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N2 180.0(3) 10_655 . ? N2 Zn1 N1 91.75(11) 10_655 10_655 ? N2 Zn1 N1 88.25(11) . 10_655 ? N2 Zn1 N1 88.25(11) 10_655 . ? N2 Zn1 N1 91.75(11) . . ? N1 Zn1 N1 180.00(15) 10_655 . ? N2 Zn1 N3 86.76(11) 10_655 . ? N2 Zn1 N3 93.24(11) . . ? N1 Zn1 N3 81.61(11) 10_655 . ? N1 Zn1 N3 98.39(11) . . ? N2 Zn1 N3 93.24(11) 10_655 10_655 ? N2 Zn1 N3 86.76(11) . 10_655 ? N1 Zn1 N3 98.39(11) 10_655 10_655 ? N1 Zn1 N3 81.61(11) . 10_655 ? N3 Zn1 N3 180.00(9) . 10_655 ? C1 N1 C4 106.9(3) . . ? C1 N1 Zn1 127.7(2) . . ? C4 N1 Zn1 123.9(2) . . ? C9 N2 C6 107.3(3) . . ? C9 N2 Zn1 127.5(2) . . ? C6 N2 Zn1 124.3(2) . . ? N1 C1 C10 125.2(3) . 10_655 ? N1 C1 C2 109.6(3) . . ? C10 C1 C2 125.1(3) 10_655 . ? C3 C2 C1 106.9(3) . . ? C3 C2 H2 126.5 . . ? C1 C2 H2 126.5 . . ? C2 C3 C4 107.7(3) . . ? C2 C3 H3 126.2 . . ? C4 C3 H3 126.2 . . ? N1 C4 C5 125.1(3) . . ? N1 C4 C3 108.9(3) . . ? C5 C4 C3 125.9(3) . . ? C4 C5 C6 128.1(3) . . ? C4 C5 C11 116.4(3) . . ? C6 C5 C11 115.5(3) . . ? N2 C6 C5 125.6(3) . . ? N2 C6 C7 109.8(3) . . ? C5 C6 C7 124.5(3) . . ? C8 C7 C6 106.7(3) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 107.5(3) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? N2 C9 C10 125.8(3) . . ? N2 C9 C8 108.6(3) . . ? C10 C9 C8 125.6(3) . . ? C9 C10 C1 125.2(3) . 10_655 ? C9 C10 C16 117.6(3) . . ? C1 C10 C16 117.2(3) 10_655 . ? C15 C11 C12 117.5(3) . . ? C15 C11 C5 121.9(3) . . ? C12 C11 C5 120.6(3) . . ? C11 C12 C13 119.3(3) . 18_544 ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 18_544 . ? N3 C13 C12 123.1(3) . 17_554 ? N3 C13 H13 118.5 . . ? C12 C13 H13 118.5 17_554 . ? C13 N3 C14 117.3(3) . . ? C13 N3 Zn1 122.9(2) . . ? C14 N3 Zn1 119.0(2) . . ? N3 C14 C15 123.1(4) . 17_554 ? N3 C14 H14 118.4 . . ? C15 C14 H14 118.4 17_554 . ? C14 C15 C11 119.7(3) 18_544 . ? C14 C15 H15 120.2 18_544 . ? C11 C15 H15 120.2 . . ? C21 C16 C17 119.2(3) . . ? C21 C16 C10 119.5(3) . . ? C17 C16 C10 121.4(3) . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 C22 118.1(5) . . ? C18 C19 C22 122.3(5) . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 120.8(4) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? N4 C22 C19 175.9(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.055 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.080 # Attachment 'Revised_hydrated_12-Zn.cif' data_e1298a _database_code_depnum_ccdc_archive 'CCDC 696295' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H28 N8 O2 Zn' _chemical_formula_weight 766.11 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 32.9346(7) _cell_length_b 32.9346(7) _cell_length_c 9.1639(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8608.3(5) _cell_formula_units_Z 9 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5860 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 24.60 _exptl_crystal_description hexagonal _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3546 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8093 _exptl_absorpt_correction_T_max 0.9342 _exptl_absorpt_process_details sadabs _exptl_special_details ; No hydrogen atoms have been introduced on the water molecules, however, they have been introduced into the formula ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34324 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4393 _reflns_number_gt 3397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0765P)^2^+61.8233P] 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 4393 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.0000 0.0000 0.02206(18) Uani 1 2 d S . . N1 N 0.53316(10) -0.00207(10) -0.1896(3) 0.0258(6) Uani 1 1 d . . . N2 N 0.55969(9) 0.05933(10) 0.0710(3) 0.0244(6) Uani 1 1 d . . . N3 N 0.46682(11) 0.04277(11) -0.0920(3) 0.0303(7) Uani 1 1 d . . . C1 C 0.51555(12) -0.03594(13) -0.2953(4) 0.0278(7) Uani 1 1 d . . . C2 C 0.55311(13) -0.02965(14) -0.3915(4) 0.0357(9) Uani 1 1 d . . . H2 H 0.5502 -0.0480 -0.4750 0.043 Uiso 1 1 calc R . . C3 C 0.59316(14) 0.00732(15) -0.3403(4) 0.0377(9) Uani 1 1 d . . . H3 H 0.6237 0.0196 -0.3804 0.045 Uiso 1 1 calc R . . C4 C 0.58050(12) 0.02445(13) -0.2125(4) 0.0277(7) Uani 1 1 d . . . C5 C 0.61229(12) 0.06121(13) -0.1229(4) 0.0285(7) Uani 1 1 d . . . C6 C 0.60251(12) 0.07722(12) 0.0070(4) 0.0268(7) Uani 1 1 d . . . C7 C 0.63739(13) 0.11455(14) 0.0970(4) 0.0341(8) Uani 1 1 d . . . H7 H 0.6699 0.1333 0.0761 0.041 Uiso 1 1 calc R . . C8 C 0.61502(13) 0.11771(14) 0.2161(4) 0.0336(8) Uani 1 1 d . . . H8 H 0.6288 0.1389 0.2952 0.040 Uiso 1 1 calc R . . C9 C 0.56614(12) 0.08276(12) 0.2004(4) 0.0263(7) Uani 1 1 d . . . C10 C 0.53125(12) 0.07312(12) 0.3049(4) 0.0269(7) Uani 1 1 d . . . C11 C 0.66265(12) 0.08568(13) -0.1683(4) 0.0289(7) Uani 1 1 d . . . C12 C 0.69409(13) 0.07494(14) -0.1006(4) 0.0357(9) Uani 1 1 d . . . H12 H 0.6836 0.0511 -0.0284 0.043 Uiso 1 1 calc R . . C13 C 0.47627(14) 0.08293(14) -0.0267(4) 0.0357(9) Uani 1 1 d . . . H13 H 0.5000 0.0953 0.0461 0.043 Uiso 1 1 calc R . . C14 C 0.43290(14) 0.02558(14) -0.1930(4) 0.0332(8) Uani 1 1 d . . . H14 H 0.4255 -0.0031 -0.2395 0.040 Uiso 1 1 calc R . . C15 C 0.67964(13) 0.12013(15) -0.2738(4) 0.0358(8) Uani 1 1 d . . . H15 H 0.6591 0.1280 -0.3232 0.043 Uiso 1 1 calc R . . C16 C 0.54457(12) 0.10388(13) 0.4358(4) 0.0301(8) Uani 1 1 d . . . C17 C 0.54223(13) 0.08510(14) 0.5736(4) 0.0350(8) Uani 1 1 d . . . H17 H 0.5320 0.0527 0.5831 0.042 Uiso 1 1 calc R . . C18 C 0.55450(15) 0.11290(16) 0.6967(4) 0.0422(10) Uani 1 1 d . . . H18 H 0.5532 0.0997 0.7899 0.051 Uiso 1 1 calc R . . C19 C 0.5685(3) 0.1597(2) 0.6842(7) 0.0841(11) Uani 1 1 d . . . C20 C 0.57137(19) 0.17931(17) 0.5477(6) 0.0558(13) Uani 1 1 d . . . H20 H 0.5814 0.2117 0.5392 0.067 Uiso 1 1 calc R . . C21 C 0.55950(16) 0.15145(14) 0.4239(5) 0.0422(10) Uani 1 1 d . . . H21 H 0.5616 0.1649 0.3306 0.051 Uiso 1 1 calc R . . C22 C 0.5794(2) 0.1873(2) 0.8157(7) 0.0841(11) Uani 1 1 d . . . N4 N 0.5864(2) 0.20685(19) 0.9242(5) 0.0841(11) Uani 1 1 d . . . O1 O 0.6051(2) 0.3126(2) 0.4531(7) 0.1183(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0165(3) 0.0264(3) 0.0244(3) -0.0013(2) -0.00005(19) 0.0115(2) N1 0.0222(14) 0.0288(15) 0.0264(14) -0.0010(11) 0.0014(11) 0.0128(12) N2 0.0193(13) 0.0255(14) 0.0278(14) -0.0025(11) -0.0003(11) 0.0109(12) N3 0.0321(16) 0.0345(17) 0.0328(15) 0.0014(13) -0.0012(12) 0.0230(14) C1 0.0277(18) 0.0299(18) 0.0279(17) -0.0014(14) 0.0012(13) 0.0159(15) C2 0.0288(19) 0.041(2) 0.0354(19) -0.0094(16) 0.0042(15) 0.0161(17) C3 0.0264(19) 0.048(2) 0.037(2) -0.0073(17) 0.0052(15) 0.0166(18) C4 0.0227(17) 0.0317(18) 0.0288(17) -0.0007(14) 0.0033(13) 0.0137(15) C5 0.0201(16) 0.0328(19) 0.0312(17) 0.0014(14) 0.0020(13) 0.0122(15) C6 0.0222(16) 0.0288(18) 0.0287(17) -0.0001(13) -0.0025(13) 0.0121(14) C7 0.0211(17) 0.034(2) 0.039(2) -0.0051(16) 0.0005(14) 0.0071(15) C8 0.0259(18) 0.034(2) 0.0345(19) -0.0071(15) -0.0016(14) 0.0103(16) C9 0.0242(17) 0.0259(17) 0.0286(17) -0.0031(13) -0.0021(13) 0.0123(14) C10 0.0250(17) 0.0285(18) 0.0282(17) -0.0037(14) -0.0031(13) 0.0143(15) C11 0.0193(16) 0.0340(19) 0.0291(17) -0.0037(14) 0.0011(13) 0.0100(15) C12 0.0269(19) 0.041(2) 0.0352(19) 0.0081(16) 0.0045(15) 0.0139(17) C13 0.039(2) 0.038(2) 0.038(2) -0.0042(16) -0.0093(16) 0.0246(18) C14 0.043(2) 0.034(2) 0.0325(18) -0.0044(15) -0.0060(16) 0.0266(18) C15 0.0253(18) 0.047(2) 0.0366(19) 0.0037(17) 0.0004(15) 0.0193(17) C16 0.0236(17) 0.0296(18) 0.0344(18) -0.0055(14) 0.0012(14) 0.0112(15) C17 0.033(2) 0.036(2) 0.0332(19) -0.0046(15) -0.0034(15) 0.0152(17) C18 0.041(2) 0.050(3) 0.033(2) -0.0086(18) -0.0021(17) 0.021(2) C19 0.092(3) 0.071(2) 0.063(2) -0.0361(16) -0.0009(17) 0.0215(19) C20 0.063(3) 0.033(2) 0.058(3) -0.009(2) 0.006(2) 0.014(2) C21 0.048(2) 0.031(2) 0.042(2) -0.0025(17) 0.0052(18) 0.0150(19) C22 0.092(3) 0.071(2) 0.063(2) -0.0361(16) -0.0009(17) 0.0215(19) N4 0.092(3) 0.071(2) 0.063(2) -0.0361(16) -0.0009(17) 0.0215(19) O1 0.112(4) 0.092(4) 0.147(5) 0.002(4) 0.013(4) 0.048(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.065(3) . ? Zn1 N2 2.065(3) 10_655 ? Zn1 N1 2.072(3) . ? Zn1 N1 2.072(3) 10_655 ? Zn1 N3 2.330(3) 10_655 ? Zn1 N3 2.330(3) . ? N1 C1 1.368(4) . ? N1 C4 1.369(4) . ? N2 C6 1.360(4) . ? N2 C9 1.372(4) . ? N3 C14 1.339(5) . ? N3 C13 1.339(5) . ? C1 C10 1.413(5) 10_655 ? C1 C2 1.447(5) . ? C2 C3 1.355(5) . ? C2 H2 0.9500 . ? C3 C4 1.449(5) . ? C3 H3 0.9500 . ? C4 C5 1.403(5) . ? C5 C6 1.404(5) . ? C5 C11 1.495(5) . ? C6 C7 1.449(5) . ? C7 C8 1.350(5) . ? C7 H7 0.9500 . ? C8 C9 1.444(5) . ? C8 H8 0.9500 . ? C9 C10 1.404(5) . ? C10 C1 1.413(5) 10_655 ? C10 C16 1.488(5) . ? C11 C15 1.379(5) . ? C11 C12 1.396(5) . ? C12 C14 1.378(5) 18_544 ? C12 H12 0.9500 . ? C13 C15 1.375(5) 17_554 ? C13 H13 0.9500 . ? C14 C12 1.378(5) 17_554 ? C14 H14 0.9500 . ? C15 C13 1.375(5) 18_544 ? C15 H15 0.9500 . ? C16 C17 1.391(5) . ? C16 C21 1.392(5) . ? C17 C18 1.380(5) . ? C17 H17 0.9500 . ? C18 C19 1.374(8) . ? C18 H18 0.9500 . ? C19 C20 1.390(8) . ? C19 C22 1.443(7) . ? C20 C21 1.387(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N4 1.144(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N2 179.997(1) . 10_655 ? N2 Zn1 N1 91.57(11) . . ? N2 Zn1 N1 88.43(11) 10_655 . ? N2 Zn1 N1 88.43(11) . 10_655 ? N2 Zn1 N1 91.57(11) 10_655 10_655 ? N1 Zn1 N1 179.998(1) . 10_655 ? N2 Zn1 N3 86.89(11) . 10_655 ? N2 Zn1 N3 93.10(11) 10_655 10_655 ? N1 Zn1 N3 82.49(11) . 10_655 ? N1 Zn1 N3 97.51(11) 10_655 10_655 ? N2 Zn1 N3 93.11(11) . . ? N2 Zn1 N3 86.90(11) 10_655 . ? N1 Zn1 N3 97.51(11) . . ? N1 Zn1 N3 82.49(11) 10_655 . ? N3 Zn1 N3 180.00(10) 10_655 . ? C1 N1 C4 107.2(3) . . ? C1 N1 Zn1 127.2(2) . . ? C4 N1 Zn1 123.9(2) . . ? C6 N2 C9 107.1(3) . . ? C6 N2 Zn1 124.4(2) . . ? C9 N2 Zn1 127.7(2) . . ? C14 N3 C13 117.3(3) . . ? C14 N3 Zn1 122.6(2) . . ? C13 N3 Zn1 119.2(2) . . ? N1 C1 C10 125.8(3) . 10_655 ? N1 C1 C2 109.3(3) . . ? C10 C1 C2 124.8(3) 10_655 . ? C3 C2 C1 107.2(3) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 106.8(3) . . ? C2 C3 H3 126.6 . . ? C4 C3 H3 126.6 . . ? N1 C4 C5 125.6(3) . . ? N1 C4 C3 109.4(3) . . ? C5 C4 C3 124.9(3) . . ? C4 C5 C6 127.4(3) . . ? C4 C5 C11 116.8(3) . . ? C6 C5 C11 115.7(3) . . ? N2 C6 C5 125.9(3) . . ? N2 C6 C7 109.4(3) . . ? C5 C6 C7 124.6(3) . . ? C8 C7 C6 107.1(3) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 107.0(3) . . ? C7 C8 H8 126.5 . . ? C9 C8 H8 126.5 . . ? N2 C9 C10 125.6(3) . . ? N2 C9 C8 109.4(3) . . ? C10 C9 C8 124.9(3) . . ? C9 C10 C1 124.6(3) . 10_655 ? C9 C10 C16 117.8(3) . . ? C1 C10 C16 117.6(3) 10_655 . ? C15 C11 C12 118.2(3) . . ? C15 C11 C5 121.5(3) . . ? C12 C11 C5 120.2(3) . . ? C14 C12 C11 118.8(4) 18_544 . ? C14 C12 H12 120.6 18_544 . ? C11 C12 H12 120.6 . . ? N3 C13 C15 123.4(4) . 17_554 ? N3 C13 H13 118.3 . . ? C15 C13 H13 118.3 17_554 . ? N3 C14 C12 123.1(3) . 17_554 ? N3 C14 H14 118.4 . . ? C12 C14 H14 118.4 17_554 . ? C13 C15 C11 119.1(4) 18_544 . ? C13 C15 H15 120.5 18_544 . ? C11 C15 H15 120.5 . . ? C17 C16 C21 118.8(3) . . ? C17 C16 C10 119.8(3) . . ? C21 C16 C10 121.4(3) . . ? C18 C17 C16 120.9(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.9(4) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.2(5) . . ? C18 C19 C22 118.4(6) . . ? C20 C19 C22 121.4(6) . . ? C21 C20 C19 119.8(5) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C16 120.3(4) . . ? C20 C21 H21 119.8 . . ? C16 C21 H21 119.8 . . ? N4 C22 C19 176.1(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.025 _refine_diff_density_min -1.519 _refine_diff_density_rms 0.101 # Attachment 'Revised_13-Zn.cif' data_e1263a _database_code_depnum_ccdc_archive 'CCDC 696296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H32 N6 O3 Zn' _chemical_formula_weight 758.13 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 Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 32.8450(3) _cell_length_b 32.8450(3) _cell_length_c 9.2054(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8600.3(2) _cell_formula_units_Z 9 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4558 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 24.99 _exptl_crystal_description hexagonal _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3528 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8196 _exptl_absorpt_correction_T_max 0.9035 _exptl_absorpt_process_details sadabs _exptl_special_details ; No hydrogen atoms have been introduced on the water molecules, however, they have been introduced into the formula ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30620 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4384 _reflns_number_gt 3738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0883P)^2^+40.1007P] 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 4384 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1719 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 1.0000 0.5000 0.02271(17) Uani 1 2 d S . . N1 N 0.53294(12) 0.99903(13) 0.3089(4) 0.0275(7) Uani 1 1 d . . . N2 N 0.43974(13) 0.94086(13) 0.4282(4) 0.0282(8) Uani 1 1 d . . . C1 C 0.51539(16) 0.96534(16) 0.2023(5) 0.0299(9) Uani 1 1 d . . . C2 C 0.55285(17) 0.97161(18) 0.1071(5) 0.0387(11) Uani 1 1 d . . . H2 H 0.5500 0.9533 0.0238 0.046 Uiso 1 1 calc R . . C3 C 0.59272(17) 1.00826(19) 0.1583(5) 0.0389(11) Uani 1 1 d . . . H3 H 0.6233 1.0207 0.1177 0.047 Uiso 1 1 calc R . . C4 C 0.58043(16) 1.02510(17) 0.2862(5) 0.0295(9) Uani 1 1 d . . . C5 C 0.61218(15) 1.06170(16) 0.3766(5) 0.0289(9) Uani 1 1 d . . . C6 C 0.60321(15) 1.07730(16) 0.5076(5) 0.0273(9) Uani 1 1 d . . . C7 C 0.36196(17) 0.88575(18) 0.4011(6) 0.0353(10) Uani 1 1 d . . . H7 H 0.3293 0.8672 0.4210 0.042 Uiso 1 1 calc R . . C8 C 0.38437(17) 0.88238(17) 0.2824(6) 0.0360(10) Uani 1 1 d . . . H8 H 0.3707 0.8609 0.2039 0.043 Uiso 1 1 calc R . . C9 C 0.43366(16) 0.91816(16) 0.2989(5) 0.0293(9) Uani 1 1 d . . . C10 C 0.46865(16) 0.92771(15) 0.1946(4) 0.0283(8) Uani 1 1 d . . . C11 C 0.58031(15) 0.91007(16) 0.6651(6) 0.0313(8) Uani 1 1 d . . . C12 C 0.54882(19) 0.89428(19) 0.5500(6) 0.0385(11) Uani 1 1 d . . . H12 H 0.5432 0.8674 0.4956 0.046 Uiso 1 1 calc R . . C13 C 0.5260(2) 0.91861(19) 0.5168(6) 0.0407(12) Uani 1 1 d . . . H13 H 0.5043 0.9076 0.4385 0.049 Uiso 1 1 calc R . . N3 N 0.53262(14) 0.95689(14) 0.5885(4) 0.0333(9) Uani 1 1 d . . . C14 C 0.5629(2) 0.97181(19) 0.6973(6) 0.0376(12) Uani 1 1 d . . . H14 H 0.5681 0.9989 0.7497 0.045 Uiso 1 1 calc R . . C15 C 0.58747(19) 0.94955(18) 0.7377(5) 0.0360(10) Uani 1 1 d . . . H15 H 0.6093 0.9616 0.8157 0.043 Uiso 1 1 calc R . . C16 C 0.45522(15) 0.89495(16) 0.0686(5) 0.0313(10) Uani 1 1 d . . . C17 C 0.44075(19) 0.84778(18) 0.0902(6) 0.0422(12) Uani 1 1 d . . . H17 H 0.4407 0.8368 0.1857 0.051 Uiso 1 1 calc R . . C18 C 0.4264(2) 0.8164(2) -0.0250(7) 0.0508(14) Uani 1 1 d . . . H18 H 0.4167 0.7843 -0.0084 0.061 Uiso 1 1 calc R . . C19 C 0.4261(3) 0.8323(2) -0.1664(7) 0.0652(9) Uani 1 1 d . . . C20 C 0.4409(2) 0.87837(17) -0.1899(5) 0.0400(10) Uani 1 1 d . . . H20 H 0.4412 0.8894 -0.2856 0.048 Uiso 1 1 calc R . . C21 C 0.4558(2) 0.90978(15) -0.0721(4) 0.0349(9) Uani 1 1 d . . . H21 H 0.4665 0.9421 -0.0897 0.042 Uiso 1 1 calc R . . O1 O 0.40995(18) 0.79764(15) -0.2701(5) 0.0652(9) Uani 1 1 d . . . C22 C 0.4030(3) 0.8104(2) -0.4133(6) 0.0652(9) Uani 1 1 d . . . H22A H 0.3799 0.8210 -0.4092 0.098 Uiso 1 1 calc R . . H22B H 0.3914 0.7831 -0.4777 0.098 Uiso 1 1 calc R . . H22C H 0.4329 0.8359 -0.4507 0.098 Uiso 1 1 calc R . . O2 O 0.3905(3) 0.6864(3) 0.0981(13) 0.075(3) Uani 0.50 1 d P . . 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 0.0187(3) 0.0249(3) 0.0257(3) 0.0010(2) 0.0004(3) 0.0118(3) N1 0.0243(17) 0.0287(18) 0.0277(17) -0.0015(14) 0.0020(14) 0.0118(15) N2 0.0228(17) 0.0313(18) 0.0303(18) -0.0019(15) -0.0002(15) 0.0134(15) C1 0.030(2) 0.030(2) 0.031(2) -0.0019(17) 0.0016(18) 0.0157(19) C2 0.031(2) 0.046(3) 0.035(3) -0.006(2) 0.003(2) 0.017(2) C3 0.028(2) 0.045(3) 0.036(3) -0.007(2) 0.0077(19) 0.013(2) C4 0.025(2) 0.033(2) 0.028(2) -0.0005(18) 0.0044(18) 0.0131(19) C5 0.0207(19) 0.034(2) 0.031(2) 0.0008(18) 0.0033(16) 0.0130(18) C6 0.0173(19) 0.028(2) 0.033(2) -0.0002(18) 0.0009(17) 0.0083(17) C7 0.024(2) 0.036(2) 0.040(3) -0.004(2) 0.0018(19) 0.0108(19) C8 0.027(2) 0.035(2) 0.039(3) -0.008(2) -0.0029(19) 0.010(2) C9 0.026(2) 0.028(2) 0.033(2) -0.0021(18) -0.0023(17) 0.0124(18) C10 0.027(2) 0.0305(19) 0.0279(19) -0.0038(15) -0.0007(18) 0.0148(19) C11 0.030(2) 0.037(2) 0.035(2) 0.006(2) 0.002(2) 0.0225(18) C12 0.045(3) 0.038(3) 0.042(3) -0.005(2) -0.007(2) 0.028(2) C13 0.044(3) 0.040(3) 0.042(3) -0.005(2) -0.009(2) 0.024(2) N3 0.031(2) 0.039(2) 0.038(2) 0.0026(17) 0.0002(17) 0.0235(18) C14 0.050(3) 0.037(3) 0.038(3) -0.005(2) -0.008(2) 0.031(2) C15 0.043(3) 0.038(3) 0.034(2) 0.000(2) -0.005(2) 0.026(2) C16 0.029(2) 0.033(2) 0.031(2) -0.0040(17) 0.0005(17) 0.0156(18) C17 0.049(3) 0.035(3) 0.040(3) 0.000(2) 0.004(2) 0.018(2) C18 0.061(4) 0.030(3) 0.057(3) -0.009(2) -0.003(3) 0.020(2) C19 0.081(2) 0.0527(17) 0.0477(15) -0.0206(14) -0.0108(16) 0.0228(17) C20 0.040(3) 0.042(2) 0.032(2) -0.0021(18) 0.000(2) 0.016(3) C21 0.035(3) 0.0298(19) 0.035(2) 0.0002(16) -0.002(2) 0.013(2) O1 0.081(2) 0.0527(17) 0.0477(15) -0.0206(14) -0.0108(16) 0.0228(17) C22 0.081(2) 0.0527(17) 0.0477(15) -0.0206(14) -0.0108(16) 0.0228(17) O2 0.045(4) 0.060(6) 0.117(8) 0.019(6) -0.029(5) 0.024(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 N2 2.070(4) 10_676 ? Zn1 N2 2.070(4) . ? Zn1 N1 2.073(4) 10_676 ? Zn1 N1 2.073(4) . ? Zn1 N3 2.309(4) 10_676 ? Zn1 N3 2.309(4) . ? N1 C4 1.369(6) . ? N1 C1 1.372(6) . ? N2 C6 1.362(6) 10_676 ? N2 C9 1.365(6) . ? C1 C10 1.411(6) . ? C1 C2 1.439(6) . ? C2 C3 1.345(7) . ? C2 H2 0.9500 . ? C3 C4 1.442(7) . ? C3 H3 0.9500 . ? C4 C5 1.404(7) . ? C5 C6 1.398(6) . ? C5 C11 1.506(6) 9_564 ? C6 N2 1.362(6) 10_676 ? C6 C7 1.449(7) 10_676 ? C7 C8 1.353(7) . ? C7 C6 1.449(7) 10_676 ? C7 H7 0.9500 . ? C8 C9 1.457(6) . ? C8 H8 0.9500 . ? C9 C10 1.407(6) . ? C10 C16 1.491(6) . ? C11 C15 1.371(7) . ? C11 C12 1.387(7) . ? C11 C5 1.506(6) 5_665 ? C12 C13 1.376(7) . ? C12 H12 0.9500 . ? C13 N3 1.338(7) . ? C13 H13 0.9500 . ? N3 C14 1.322(7) . ? C14 C15 1.382(7) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.380(6) . ? C16 C17 1.389(7) . ? C17 C18 1.387(8) . ? C17 H17 0.9500 . ? C18 C19 1.403(9) . ? C18 H18 0.9500 . ? C19 C20 1.355(8) . ? C19 O1 1.374(7) . ? C20 C21 1.406(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O1 C22 1.436(8) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 N2 Zn1 N2 179.998(1) 10_676 . ? N2 Zn1 N1 88.63(14) 10_676 10_676 ? N2 Zn1 N1 91.37(14) . 10_676 ? N2 Zn1 N1 91.37(14) 10_676 . ? N2 Zn1 N1 88.63(14) . . ? N1 Zn1 N1 180.0(2) 10_676 . ? N2 Zn1 N3 93.23(15) 10_676 10_676 ? N2 Zn1 N3 86.77(15) . 10_676 ? N1 Zn1 N3 83.36(14) 10_676 10_676 ? N1 Zn1 N3 96.65(14) . 10_676 ? N2 Zn1 N3 86.77(15) 10_676 . ? N2 Zn1 N3 93.23(15) . . ? N1 Zn1 N3 96.65(14) 10_676 . ? N1 Zn1 N3 83.35(14) . . ? N3 Zn1 N3 180.000(1) 10_676 . ? C4 N1 C1 106.4(4) . . ? C4 N1 Zn1 124.1(3) . . ? C1 N1 Zn1 127.4(3) . . ? C6 N2 C9 107.6(4) 10_676 . ? C6 N2 Zn1 124.6(3) 10_676 . ? C9 N2 Zn1 127.0(3) . . ? N1 C1 C10 125.2(4) . . ? N1 C1 C2 109.6(4) . . ? C10 C1 C2 124.9(4) . . ? C3 C2 C1 107.2(4) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 107.2(4) . . ? C2 C3 H3 126.4 . . ? C4 C3 H3 126.4 . . ? N1 C4 C5 124.8(4) . . ? N1 C4 C3 109.6(4) . . ? C5 C4 C3 125.6(4) . . ? C6 C5 C4 128.5(4) . . ? C6 C5 C11 114.8(4) . 9_564 ? C4 C5 C11 116.6(4) . 9_564 ? N2 C6 C5 125.2(4) 10_676 . ? N2 C6 C7 109.0(4) 10_676 10_676 ? C5 C6 C7 125.8(4) . 10_676 ? C8 C7 C6 107.7(4) . 10_676 ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 10_676 . ? C7 C8 C9 106.3(4) . . ? C7 C8 H8 126.9 . . ? C9 C8 H8 126.9 . . ? N2 C9 C10 126.4(4) . . ? N2 C9 C8 109.4(4) . . ? C10 C9 C8 124.3(4) . . ? C9 C10 C1 124.8(4) . . ? C9 C10 C16 117.1(4) . . ? C1 C10 C16 118.1(4) . . ? C15 C11 C12 118.0(5) . . ? C15 C11 C5 121.4(4) . 5_665 ? C12 C11 C5 120.6(4) . 5_665 ? C13 C12 C11 118.2(5) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? N3 C13 C12 123.8(5) . . ? N3 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C14 N3 C13 117.4(4) . . ? C14 N3 Zn1 122.3(3) . . ? C13 N3 Zn1 119.7(3) . . ? N3 C14 C15 122.6(5) . . ? N3 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C11 C15 C14 120.0(5) . . ? C11 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C21 C16 C17 117.7(4) . . ? C21 C16 C10 121.9(4) . . ? C17 C16 C10 120.4(4) . . ? C18 C17 C16 121.2(5) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 119.8(5) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 O1 126.0(6) . . ? C20 C19 C18 119.9(5) . . ? O1 C19 C18 114.1(6) . . ? C19 C20 C21 119.7(5) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C16 C21 C20 121.8(4) . . ? C16 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C19 O1 C22 116.6(5) . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.858 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.104 # Attachment 'Revised_15-Zn.cif' data_e1299a _database_code_depnum_ccdc_archive 'CCDC 696297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H26 N6 O2 Zn' _chemical_formula_weight 712.06 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 32.941(2) _cell_length_b 32.941(2) _cell_length_c 9.4384(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8869.5(13) _cell_formula_units_Z 9 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 566 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 21.11 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3294 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9804 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4521 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2185 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4521 _reflns_number_gt 1993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Crystals diffracted poorly and revealed disordered solvent molecules (probably water) which could not be a positionned precisely. Correspondingly, the contribution of the disordered solvents was substracted from the diffraction data by SQUEEZE procedure with the aid of the platon software. ; _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^)+(0.1065P)^2^+10.5383P] 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 4521 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2053 _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.2888 _refine_ls_wR_factor_gt 0.2487 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.0000 0.0000 0.0258(3) Uani 1 2 d S . . N1 N 0.5332(2) -0.0009(2) -0.1836(6) 0.0284(14) Uani 1 1 d . . . N2 N 0.5596(2) 0.0583(2) 0.0705(6) 0.0268(13) Uani 1 1 d . . . C1 C 0.5164(3) -0.0340(3) -0.2878(7) 0.0294(17) Uani 1 1 d . . . C2 C 0.5547(3) -0.0270(3) -0.3845(9) 0.046(2) Uani 1 1 d . . . H2 H 0.5520 -0.0444 -0.4677 0.055 Uiso 1 1 calc R . . C3 C 0.5944(3) 0.0092(3) -0.3309(8) 0.042(2) Uani 1 1 d . . . H3 H 0.6252 0.0213 -0.3673 0.051 Uiso 1 1 calc R . . C4 C 0.5811(3) 0.0260(3) -0.2072(8) 0.0335(18) Uani 1 1 d . . . C5 C 0.6130(3) 0.0623(3) -0.1186(8) 0.0308(17) Uani 1 1 d . . . C6 C 0.6027(3) 0.0773(3) 0.0099(7) 0.0318(18) Uani 1 1 d . . . C7 C 0.6375(3) 0.1137(3) 0.0989(8) 0.0378(19) Uani 1 1 d . . . H7 H 0.6700 0.1324 0.0799 0.045 Uiso 1 1 calc R . . C8 C 0.6145(3) 0.1157(3) 0.2143(9) 0.040(2) Uani 1 1 d . . . H8 H 0.6281 0.1365 0.2921 0.048 Uiso 1 1 calc R . . C9 C 0.5656(3) 0.0808(3) 0.1991(8) 0.0290(16) Uani 1 1 d . . . C10 C 0.5302(3) 0.0706(3) 0.3014(7) 0.0278(16) Uani 1 1 d . . . C11 C 0.6634(3) 0.0876(3) -0.1618(8) 0.0342(18) Uani 1 1 d . . . C12 C 0.6788(3) 0.1199(3) -0.2722(9) 0.044(2) Uani 1 1 d . . . H12 H 0.6576 0.1264 -0.3221 0.053 Uiso 1 1 calc R . . C13 C 0.5243(3) -0.0831(3) 0.0267(8) 0.042(2) Uani 1 1 d . . . H13 H 0.5023 -0.0945 -0.0487 0.050 Uiso 1 1 calc R . . N3 N 0.5319(2) -0.0440(2) 0.0931(6) 0.0343(15) Uani 1 1 d . . . C14 C 0.7417(3) 0.1026(3) -0.1355(8) 0.042(2) Uani 1 1 d . . . H14 H 0.7634 0.0962 -0.0879 0.051 Uiso 1 1 calc R . . C15 C 0.6953(3) 0.0785(3) -0.0954(8) 0.041(2) Uani 1 1 d . . . H15 H 0.6853 0.0557 -0.0221 0.050 Uiso 1 1 calc R . . C16 C 0.5436(3) 0.1023(3) 0.4242(9) 0.041(2) Uani 1 1 d . . . C17 C 0.5567(4) 0.1491(4) 0.4070(11) 0.064(3) Uani 1 1 d . . . H17 H 0.5576 0.1611 0.3149 0.076 Uiso 1 1 calc R . . C18 C 0.5685(4) 0.1785(4) 0.5251(16) 0.092(5) Uani 1 1 d . . . H18 H 0.5770 0.2104 0.5134 0.110 Uiso 1 1 calc R . . C19 C 0.5680(4) 0.1612(6) 0.6582(15) 0.100(6) Uani 1 1 d . . . C20 C 0.5542(4) 0.1153(6) 0.6765(11) 0.079(4) Uani 1 1 d . . . H20 H 0.5525 0.1035 0.7694 0.095 Uiso 1 1 calc R . . C21 C 0.5422(3) 0.0849(4) 0.5596(8) 0.048(2) Uani 1 1 d . . . H21 H 0.5333 0.0529 0.5730 0.058 Uiso 1 1 calc R . . O1 O 0.5773(3) 0.1891(4) 0.7857(8) 0.100 Uani 1 1 d . . . H1 H 0.5967 0.1862 0.8364 0.150 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 0.0199(6) 0.0290(7) 0.0283(6) 0.0005(5) 0.0015(5) 0.0120(6) N1 0.025(3) 0.034(4) 0.026(3) 0.000(3) -0.003(3) 0.015(3) N2 0.023(3) 0.030(3) 0.030(3) 0.003(3) 0.004(3) 0.015(3) C1 0.027(4) 0.034(4) 0.024(3) -0.003(3) -0.003(3) 0.013(3) C2 0.032(5) 0.047(6) 0.044(5) 0.000(4) 0.011(4) 0.009(4) C3 0.028(4) 0.053(6) 0.039(5) -0.015(4) 0.006(4) 0.016(4) C4 0.035(4) 0.036(4) 0.030(4) -0.003(3) 0.003(3) 0.018(4) C5 0.029(4) 0.029(4) 0.034(4) 0.003(3) 0.010(3) 0.014(4) C6 0.026(4) 0.037(4) 0.027(4) 0.003(3) -0.006(3) 0.011(4) C7 0.017(4) 0.046(5) 0.044(5) -0.006(4) 0.001(3) 0.011(4) C8 0.030(4) 0.033(5) 0.057(5) -0.005(4) -0.006(4) 0.016(4) C9 0.023(4) 0.021(4) 0.040(4) 0.001(3) 0.003(3) 0.009(3) C10 0.034(4) 0.023(4) 0.031(4) -0.005(3) -0.004(3) 0.018(3) C11 0.025(4) 0.037(5) 0.035(4) -0.003(3) 0.003(3) 0.010(3) C12 0.036(5) 0.050(6) 0.047(5) 0.012(4) 0.007(4) 0.022(4) C13 0.048(5) 0.050(6) 0.042(5) 0.000(4) -0.014(4) 0.035(5) N3 0.035(4) 0.044(4) 0.035(3) 0.005(3) 0.001(3) 0.028(3) C14 0.029(5) 0.056(6) 0.045(5) 0.009(4) 0.000(4) 0.023(4) C15 0.024(4) 0.051(5) 0.038(4) 0.016(4) 0.004(4) 0.010(4) C16 0.033(5) 0.042(5) 0.044(5) -0.008(4) -0.002(4) 0.015(4) C17 0.055(6) 0.048(6) 0.079(7) -0.027(5) 0.005(5) 0.018(5) C18 0.068(8) 0.057(8) 0.136(12) -0.056(8) 0.009(8) 0.021(7) C19 0.061(8) 0.137(14) 0.080(9) -0.082(10) -0.009(7) 0.033(9) C20 0.051(7) 0.132(13) 0.048(6) -0.032(7) -0.008(5) 0.041(8) C21 0.042(5) 0.064(6) 0.033(4) -0.007(4) -0.009(4) 0.022(5) O1 0.061 0.137 0.080 0.000 0.000 0.034 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.053(6) 10_655 ? Zn1 N2 2.053(6) . ? Zn1 N1 2.058(6) 10_655 ? Zn1 N1 2.058(6) . ? Zn1 N3 2.345(6) 10_655 ? Zn1 N3 2.345(6) . ? N1 C1 1.364(9) . ? N1 C4 1.387(9) . ? N2 C6 1.360(9) . ? N2 C9 1.383(9) . ? C1 C10 1.406(10) 10_655 ? C1 C2 1.479(10) . ? C2 C3 1.351(11) . ? C2 H2 0.9500 . ? C3 C4 1.450(10) . ? C3 H3 0.9500 . ? C4 C5 1.406(10) . ? C5 C6 1.414(10) . ? C5 C11 1.494(10) . ? C6 C7 1.441(10) . ? C7 C8 1.346(11) . ? C7 H7 0.9500 . ? C8 C9 1.444(10) . ? C8 H8 0.9500 . ? C9 C10 1.420(10) . ? C10 C1 1.406(10) 10_655 ? C10 C16 1.472(10) . ? C11 C15 1.379(11) . ? C11 C12 1.391(11) . ? C12 C13 1.385(11) 9_654 ? C12 H12 0.9500 . ? C13 N3 1.338(10) . ? C13 C12 1.385(11) 5_545 ? C13 H13 0.9500 . ? N3 C14 1.349(10) 5_545 ? C14 N3 1.349(10) 9_654 ? C14 C15 1.378(11) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.384(13) . ? C16 C21 1.394(11) . ? C17 C18 1.399(14) . ? C17 H17 0.9500 . ? C18 C19 1.38(2) . ? C18 H18 0.9500 . ? C19 C20 1.35(2) . ? C19 O1 1.451(12) . ? C20 C21 1.408(14) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O1 H1 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N2 180.0(6) 10_655 . ? N2 Zn1 N1 91.1(2) 10_655 10_655 ? N2 Zn1 N1 88.9(2) . 10_655 ? N2 Zn1 N1 88.9(2) 10_655 . ? N2 Zn1 N1 91.1(2) . . ? N1 Zn1 N1 180.0(4) 10_655 . ? N2 Zn1 N3 86.7(2) 10_655 10_655 ? N2 Zn1 N3 93.3(2) . 10_655 ? N1 Zn1 N3 84.3(2) 10_655 10_655 ? N1 Zn1 N3 95.7(2) . 10_655 ? N2 Zn1 N3 93.3(2) 10_655 . ? N2 Zn1 N3 86.7(2) . . ? N1 Zn1 N3 95.7(2) 10_655 . ? N1 Zn1 N3 84.3(2) . . ? N3 Zn1 N3 180.0(3) 10_655 . ? C1 N1 C4 105.8(6) . . ? C1 N1 Zn1 127.7(5) . . ? C4 N1 Zn1 124.7(5) . . ? C6 N2 C9 106.5(6) . . ? C6 N2 Zn1 125.8(5) . . ? C9 N2 Zn1 126.8(5) . . ? N1 C1 C10 125.9(7) . 10_655 ? N1 C1 C2 110.2(7) . . ? C10 C1 C2 123.9(7) 10_655 . ? C3 C2 C1 106.2(7) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? C2 C3 C4 107.2(7) . . ? C2 C3 H3 126.4 . . ? C4 C3 H3 126.4 . . ? N1 C4 C5 125.2(7) . . ? N1 C4 C3 110.4(7) . . ? C5 C4 C3 124.2(7) . . ? C4 C5 C6 126.8(7) . . ? C4 C5 C11 117.6(6) . . ? C6 C5 C11 115.6(7) . . ? N2 C6 C5 125.3(7) . . ? N2 C6 C7 110.5(6) . . ? C5 C6 C7 124.1(7) . . ? C8 C7 C6 106.3(7) . . ? C8 C7 H7 126.9 . . ? C6 C7 H7 126.9 . . ? C7 C8 C9 108.1(7) . . ? C7 C8 H8 126.0 . . ? C9 C8 H8 126.0 . . ? N2 C9 C10 126.1(7) . . ? N2 C9 C8 108.6(7) . . ? C10 C9 C8 125.3(7) . . ? C1 C10 C9 123.8(6) 10_655 . ? C1 C10 C16 119.4(7) 10_655 . ? C9 C10 C16 116.7(7) . . ? C15 C11 C12 118.8(7) . . ? C15 C11 C5 120.6(7) . . ? C12 C11 C5 120.6(7) . . ? C13 C12 C11 117.7(8) 9_654 . ? C13 C12 H12 121.2 9_654 . ? C11 C12 H12 121.2 . . ? N3 C13 C12 124.0(7) . 5_545 ? N3 C13 H13 118.0 . . ? C12 C13 H13 118.0 5_545 . ? C13 N3 C14 117.5(7) . 5_545 ? C13 N3 Zn1 119.6(5) . . ? C14 N3 Zn1 122.0(5) 5_545 . ? N3 C14 C15 122.2(8) 9_654 . ? N3 C14 H14 118.9 9_654 . ? C15 C14 H14 118.9 . . ? C14 C15 C11 119.8(7) . . ? C14 C15 H15 120.1 . . ? C11 C15 H15 120.1 . . ? C17 C16 C21 119.6(9) . . ? C17 C16 C10 120.8(8) . . ? C21 C16 C10 119.5(8) . . ? C16 C17 C18 120.1(11) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.0(12) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.4(10) . . ? C20 C19 O1 116.6(15) . . ? C18 C19 O1 122.7(16) . . ? C19 C20 C21 120.9(12) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C16 C21 C20 119.0(11) . . ? C16 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C19 O1 H1 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.870 _refine_diff_density_min -1.893 _refine_diff_density_rms 0.129 # Attachment 'Revised_16-Zn.cif' data_e1037a _database_code_depnum_ccdc_archive 'CCDC 696298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H28 F6 N6 O2 Zn' _chemical_formula_weight 852.09 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 33.1347(4) _cell_length_b 33.1347(4) _cell_length_c 9.1686(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8717.7(3) _cell_formula_units_Z 9 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3045 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 21.53 _exptl_crystal_description hexagonal _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3906 _exptl_absorpt_coefficient_mu 0.710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8595 _exptl_absorpt_correction_T_max 0.8949 _exptl_absorpt_process_details sadabs _exptl_special_details ; No hydrogen atoms have been introduced on the water molecules, however, they have been introduced into the formula ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26919 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.70 _reflns_number_total 4513 _reflns_number_gt 2701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.5000P] 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 4513 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.1780 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.0000 0.5000 0.0327(2) Uani 1 2 d S . . N1 N 0.49873(10) 0.05816(11) 0.5717(4) 0.0344(7) Uani 1 1 d . . . N2 N 0.53466(11) 0.00161(11) 0.6889(4) 0.0353(7) Uani 1 1 d . . . N3 N 0.57655(11) 0.04280(12) 0.4081(4) 0.0412(8) Uani 1 1 d . . . C1 C 0.51591(13) 0.08162(13) 0.7019(4) 0.0347(9) Uani 1 1 d . . . C2 C 0.50231(14) 0.11655(15) 0.7171(5) 0.0428(10) Uani 1 1 d . . . H2 H 0.5100 0.1379 0.7957 0.051 Uiso 1 1 calc R . . C3 C 0.47662(15) 0.11328(14) 0.5991(5) 0.0410(10) Uani 1 1 d . . . H3 H 0.4629 0.1319 0.5790 0.049 Uiso 1 1 calc R . . C4 C 0.47386(13) 0.07618(13) 0.5084(4) 0.0356(9) Uani 1 1 d . . . C5 C 0.44838(14) 0.06043(14) 0.3785(4) 0.0372(9) Uani 1 1 d . . . C6 C 0.55599(14) -0.02447(14) 0.7125(4) 0.0378(9) Uani 1 1 d . . . C7 C 0.58537(15) -0.00742(15) 0.8394(5) 0.0471(11) Uani 1 1 d . . . H7 H 0.6036 -0.0196 0.8792 0.056 Uiso 1 1 calc R . . C8 C 0.58220(15) 0.02946(15) 0.8923(5) 0.0441(10) Uani 1 1 d . . . H8 H 0.5975 0.0477 0.9758 0.053 Uiso 1 1 calc R . . C9 C 0.55060(13) 0.03522(14) 0.7947(4) 0.0363(9) Uani 1 1 d . . . C10 C 0.54067(13) 0.07172(13) 0.8052(4) 0.0350(9) Uani 1 1 d . . . C11 C 0.42233(14) 0.08487(13) 0.3329(4) 0.0371(9) Uani 1 1 d . . . C12 C 0.43817(16) 0.11677(16) 0.2196(5) 0.0480(11) Uani 1 1 d . . . H12 H 0.4650 0.1227 0.1651 0.058 Uiso 1 1 calc R . . C13 C 0.59231(14) 0.02674(15) 0.3022(5) 0.0454(10) Uani 1 1 d . . . H13 H 0.5708 -0.0009 0.2524 0.054 Uiso 1 1 calc R . . C14 C 0.60774(15) 0.08092(15) 0.4792(5) 0.0486(11) Uani 1 1 d . . . H14 H 0.5970 0.0922 0.5563 0.058 Uiso 1 1 calc R . . C15 C 0.38216(15) 0.07639(15) 0.4049(5) 0.0453(10) Uani 1 1 d . . . H15 H 0.3698 0.0540 0.4811 0.054 Uiso 1 1 calc R . . C16 C 0.55873(14) 0.10310(14) 0.9364(4) 0.0384(9) Uani 1 1 d . . . C17 C 0.59158(15) 0.15019(15) 0.9202(5) 0.0494(11) Uani 1 1 d . . . H17 H 0.6027 0.1626 0.8258 0.059 Uiso 1 1 calc R . . C18 C 0.60809(17) 0.17889(16) 1.0413(6) 0.0571(13) Uani 1 1 d . . . H18 H 0.6305 0.2110 1.0300 0.069 Uiso 1 1 calc R . . C19 C 0.59180(17) 0.16076(17) 1.1800(5) 0.0544(12) Uani 1 1 d . . . C22 C 0.6116(2) 0.1907(2) 1.3113(8) 0.0755(17) Uani 1 1 d . . . C20 C 0.55908(15) 0.11450(16) 1.1949(5) 0.0477(11) Uani 1 1 d . . . H20 H 0.5475 0.1022 1.2890 0.057 Uiso 1 1 calc R . . C26 C 0.54277(14) 0.08568(15) 1.0744(5) 0.0418(10) Uani 1 1 d . . . H21 H 0.5204 0.0536 1.0866 0.050 Uiso 1 1 calc R . . F1 F 0.62604(14) 0.23588(14) 1.2828(5) 0.1049(13) Uani 1 1 d . . . F2 F 0.6495(2) 0.19128(17) 1.3614(6) 0.150(2) Uani 1 1 d . . . F3 F 0.5832(2) 0.17636(19) 1.4220(5) 0.169(3) Uani 1 1 d . . . O1 O 0.7049(2) 0.31306(19) 0.9726(10) 0.168(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0316(4) 0.0357(4) 0.0358(4) 0.0024(3) 0.0005(3) 0.0207(3) N1 0.0297(16) 0.0381(17) 0.0387(19) 0.0040(15) 0.0012(14) 0.0195(14) N2 0.0360(17) 0.0384(18) 0.0369(19) 0.0006(14) 0.0015(14) 0.0227(15) N3 0.0310(17) 0.0435(19) 0.043(2) 0.0041(16) 0.0050(15) 0.0141(15) C1 0.0326(19) 0.035(2) 0.038(2) -0.0006(17) 0.0015(17) 0.0184(17) C2 0.044(2) 0.043(2) 0.047(3) -0.0085(19) -0.0035(19) 0.0259(19) C3 0.048(2) 0.042(2) 0.044(2) -0.0030(19) -0.0048(19) 0.031(2) C4 0.0336(19) 0.037(2) 0.041(2) 0.0042(17) 0.0025(17) 0.0212(17) C5 0.038(2) 0.039(2) 0.041(2) 0.0030(18) 0.0002(17) 0.0236(18) C6 0.038(2) 0.040(2) 0.038(2) 0.0015(18) -0.0041(18) 0.0221(18) C7 0.046(2) 0.053(3) 0.051(3) -0.007(2) -0.015(2) 0.031(2) C8 0.044(2) 0.052(3) 0.045(3) -0.004(2) -0.010(2) 0.031(2) C9 0.035(2) 0.039(2) 0.037(2) 0.0032(17) 0.0011(17) 0.0199(17) C10 0.033(2) 0.039(2) 0.033(2) -0.0013(17) 0.0004(16) 0.0182(17) C11 0.042(2) 0.040(2) 0.036(2) -0.0042(17) -0.0044(18) 0.0260(19) C12 0.048(2) 0.053(3) 0.054(3) 0.012(2) 0.008(2) 0.033(2) C13 0.036(2) 0.046(2) 0.045(3) -0.003(2) 0.0024(19) 0.0141(19) C14 0.043(2) 0.050(3) 0.050(3) -0.003(2) 0.005(2) 0.021(2) C15 0.047(2) 0.052(3) 0.047(3) 0.008(2) 0.001(2) 0.032(2) C16 0.037(2) 0.039(2) 0.041(2) -0.0026(18) -0.0023(18) 0.0206(18) C17 0.047(2) 0.043(2) 0.054(3) 0.000(2) -0.002(2) 0.020(2) C18 0.056(3) 0.038(2) 0.067(4) -0.008(2) -0.005(3) 0.016(2) C19 0.059(3) 0.057(3) 0.053(3) -0.014(2) -0.013(2) 0.033(2) C22 0.081(4) 0.058(3) 0.084(5) -0.020(3) -0.013(4) 0.032(3) C20 0.043(2) 0.052(3) 0.049(3) -0.003(2) 0.003(2) 0.024(2) C26 0.044(2) 0.041(2) 0.040(2) -0.0031(18) 0.0002(19) 0.0210(19) F1 0.115(3) 0.089(3) 0.111(3) -0.041(2) -0.023(3) 0.051(2) F2 0.181(5) 0.122(4) 0.151(4) -0.047(3) -0.092(4) 0.078(4) F3 0.213(6) 0.128(4) 0.093(4) -0.037(3) 0.030(4) 0.031(4) O1 0.118(5) 0.086(4) 0.278(10) 0.009(5) -0.013(5) 0.035(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 N1 2.056(3) . ? Zn1 N1 2.056(3) 10_656 ? Zn1 N2 2.064(3) . ? Zn1 N2 2.064(3) 10_656 ? Zn1 N3 2.357(3) 10_656 ? Zn1 N3 2.358(3) . ? N1 C4 1.365(5) . ? N1 C1 1.383(5) . ? N2 C9 1.368(5) . ? N2 C6 1.380(5) . ? N3 C13 1.332(5) . ? N3 C14 1.335(5) . ? C1 C10 1.395(5) . ? C1 C2 1.444(5) . ? C2 C3 1.347(6) . ? C2 H2 0.9500 . ? C3 C4 1.448(5) . ? C3 H3 0.9500 . ? C4 C5 1.401(6) . ? C5 C6 1.402(5) 10_656 ? C5 C11 1.508(5) . ? C6 C5 1.402(5) 10_656 ? C6 C7 1.439(6) . ? C7 C8 1.366(6) . ? C7 H7 0.9500 . ? C8 C9 1.460(5) . ? C8 H8 0.9500 . ? C9 C10 1.407(5) . ? C10 C16 1.504(5) . ? C11 C15 1.383(5) . ? C11 C12 1.384(6) . ? C12 C14 1.380(6) 17 ? C12 H12 0.9500 . ? C13 C15 1.394(6) 18_545 ? C13 H13 0.9500 . ? C14 C12 1.380(6) 18_545 ? C14 H14 0.9500 . ? C15 C13 1.394(6) 17 ? C15 H15 0.9500 . ? C16 C26 1.382(6) . ? C16 C17 1.394(6) . ? C17 C18 1.385(6) . ? C17 H17 0.9500 . ? C18 C19 1.394(7) . ? C18 H18 0.9500 . ? C19 C20 1.372(6) . ? C19 C22 1.488(7) . ? C22 F3 1.301(8) . ? C22 F2 1.329(8) . ? C22 F1 1.348(7) . ? C20 C26 1.381(6) . ? C20 H20 0.9500 . ? C26 H21 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 N1 Zn1 N1 180.0 . 10_656 ? N1 Zn1 N2 88.82(12) . . ? N1 Zn1 N2 91.18(12) 10_656 . ? N1 Zn1 N2 91.18(12) . 10_656 ? N1 Zn1 N2 88.83(12) 10_656 10_656 ? N2 Zn1 N2 180.0 . 10_656 ? N1 Zn1 N3 85.96(12) . 10_656 ? N1 Zn1 N3 94.04(12) 10_656 10_656 ? N2 Zn1 N3 97.64(12) . 10_656 ? N2 Zn1 N3 82.36(12) 10_656 10_656 ? N1 Zn1 N3 94.04(12) . . ? N1 Zn1 N3 85.96(12) 10_656 . ? N2 Zn1 N3 82.36(12) . . ? N2 Zn1 N3 97.64(12) 10_656 . ? N3 Zn1 N3 180.0 10_656 . ? C4 N1 C1 106.8(3) . . ? C4 N1 Zn1 125.0(3) . . ? C1 N1 Zn1 127.4(2) . . ? C9 N2 C6 106.8(3) . . ? C9 N2 Zn1 126.8(2) . . ? C6 N2 Zn1 124.6(3) . . ? C13 N3 C14 117.4(4) . . ? C13 N3 Zn1 122.6(3) . . ? C14 N3 Zn1 119.1(3) . . ? N1 C1 C10 125.4(3) . . ? N1 C1 C2 109.2(3) . . ? C10 C1 C2 125.4(4) . . ? C3 C2 C1 107.2(4) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 107.4(3) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C5 125.5(4) . . ? N1 C4 C3 109.4(3) . . ? C5 C4 C3 125.1(3) . . ? C4 C5 C6 127.6(4) . 10_656 ? C4 C5 C11 115.8(3) . . ? C6 C5 C11 116.6(3) 10_656 . ? N2 C6 C5 124.8(4) . 10_656 ? N2 C6 C7 109.8(3) . . ? C5 C6 C7 125.3(4) 10_656 . ? C8 C7 C6 107.3(4) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C7 C8 C9 106.3(4) . . ? C7 C8 H8 126.8 . . ? C9 C8 H8 126.8 . . ? N2 C9 C10 126.0(3) . . ? N2 C9 C8 109.8(3) . . ? C10 C9 C8 124.2(4) . . ? C1 C10 C9 125.0(4) . . ? C1 C10 C16 117.2(3) . . ? C9 C10 C16 117.8(3) . . ? C15 C11 C12 118.2(4) . . ? C15 C11 C5 120.6(4) . . ? C12 C11 C5 121.2(4) . . ? C14 C12 C11 118.7(4) 17 . ? C14 C12 H12 120.7 17 . ? C11 C12 H12 120.7 . . ? N3 C13 C15 122.7(4) . 18_545 ? N3 C13 H13 118.7 . . ? C15 C13 H13 118.7 18_545 . ? N3 C14 C12 123.8(4) . 18_545 ? N3 C14 H14 118.1 . . ? C12 C14 H14 118.1 18_545 . ? C11 C15 C13 119.2(4) . 17 ? C11 C15 H15 120.4 . . ? C13 C15 H15 120.4 17 . ? C26 C16 C17 119.1(4) . . ? C26 C16 C10 120.4(4) . . ? C17 C16 C10 120.4(4) . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.0(4) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 119.4(4) . . ? C20 C19 C22 120.2(5) . . ? C18 C19 C22 120.2(5) . . ? F3 C22 F2 103.9(7) . . ? F3 C22 F1 110.4(6) . . ? F2 C22 F1 104.1(5) . . ? F3 C22 C19 113.0(6) . . ? F2 C22 C19 112.7(5) . . ? F1 C22 C19 112.2(6) . . ? C19 C20 C26 120.7(4) . . ? C19 C20 H20 119.7 . . ? C26 C20 H20 119.7 . . ? C20 C26 C16 120.5(4) . . ? C20 C26 H21 119.7 . . ? C16 C26 H21 119.7 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.70 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.369 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.090 # Attachment '16-Zn 1D.cif' data_e878a _database_code_depnum_ccdc_archive 'CCDC 696299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H25 Cl3 F6 N6 Zn' _chemical_formula_weight 935.43 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 17.0482(11) _cell_length_b 14.1382(10) _cell_length_c 17.2892(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.433(3) _cell_angle_gamma 90.00 _cell_volume 4084.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1463 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 18.95 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8526 _exptl_absorpt_correction_T_max 0.9418 _exptl_absorpt_process_details sadabs _exptl_special_details ; The large R2 value is due to a small crystal size and a poor diffracting power. ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22805 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_sigmaI/netI 0.1814 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.56 _reflns_number_total 9223 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.5885P] 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 9223 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2317 _refine_ls_R_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.2781 _refine_ls_wR_factor_gt 0.2227 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.55123(5) 0.24509(7) 0.16754(5) 0.0280(3) Uani 1 1 d . . . N1 N 0.5885(4) 0.1796(4) 0.2763(3) 0.0298(15) Uani 1 1 d . . . N2 N 0.6025(4) 0.1361(5) 0.1169(3) 0.0295(15) Uani 1 1 d . . . N3 N 0.4878(4) 0.2807(4) 0.0561(4) 0.0279(15) Uani 1 1 d . . . N4 N 0.4670(3) 0.3178(5) 0.2152(4) 0.0299(15) Uani 1 1 d . . . C1 C 0.5696(5) 0.2075(6) 0.3475(5) 0.0340(19) Uani 1 1 d . . . C2 C 0.6179(5) 0.1531(6) 0.4100(5) 0.038(2) Uani 1 1 d . . . H2 H 0.6173 0.1580 0.4647 0.046 Uiso 1 1 calc R . . C3 C 0.6643(5) 0.0939(6) 0.3770(5) 0.037(2) Uani 1 1 d . . . H3 H 0.7020 0.0499 0.4042 0.045 Uiso 1 1 calc R . . C4 C 0.6459(5) 0.1100(5) 0.2931(5) 0.0314(19) Uani 1 1 d . . . C5 C 0.6778(5) 0.0618(6) 0.2366(5) 0.0317(19) Uani 1 1 d . . . C6 C 0.6578(4) 0.0710(5) 0.1545(4) 0.0292(18) Uani 1 1 d . . . C7 C 0.6885(5) 0.0169(6) 0.0976(5) 0.040(2) Uani 1 1 d . . . H7 H 0.7282 -0.0311 0.1089 0.048 Uiso 1 1 calc R . . C8 C 0.6523(5) 0.0451(6) 0.0259(5) 0.041(2) Uani 1 1 d . . . H8 H 0.6600 0.0200 -0.0230 0.049 Uiso 1 1 calc R . . C9 C 0.5988(5) 0.1212(6) 0.0369(5) 0.0325(19) Uani 1 1 d . . . C10 C 0.5483(5) 0.1712(6) -0.0241(4) 0.0328(19) Uani 1 1 d . . . C11 C 0.4965(4) 0.2435(6) -0.0139(4) 0.0298(17) Uani 1 1 d . . . C12 C 0.4416(5) 0.2889(6) -0.0777(5) 0.038(2) Uani 1 1 d . . . H12 H 0.4347 0.2751 -0.1324 0.045 Uiso 1 1 calc R . . C13 C 0.4017(5) 0.3554(6) -0.0433(5) 0.041(2) Uani 1 1 d . . . H13 H 0.3624 0.3980 -0.0699 0.049 Uiso 1 1 calc R . . C14 C 0.4298(4) 0.3495(6) 0.0399(5) 0.0332(19) Uani 1 1 d . . . C15 C 0.3995(4) 0.4034(5) 0.0965(5) 0.0289(18) Uani 1 1 d . . . C16 C 0.4161(4) 0.3874(5) 0.1773(4) 0.0285(18) Uani 1 1 d . . . C17 C 0.3824(5) 0.4393(6) 0.2338(5) 0.036(2) Uani 1 1 d . . . H17 H 0.3453 0.4900 0.2230 0.044 Uiso 1 1 calc R . . C18 C 0.4132(5) 0.4028(6) 0.3051(5) 0.039(2) Uani 1 1 d . . . H18 H 0.4016 0.4232 0.3540 0.047 Uiso 1 1 calc R . . C19 C 0.4662(5) 0.3284(6) 0.2946(5) 0.0337(19) Uani 1 1 d . . . C20 C 0.5136(4) 0.2745(6) 0.3563(5) 0.0321(19) Uani 1 1 d . . . C21 C 0.7384(5) -0.0135(6) 0.2660(4) 0.0313(19) Uani 1 1 d . . . C22 C 0.7191(5) -0.1084(6) 0.2707(5) 0.046(2) Uani 1 1 d . . . H22 H 0.6649 -0.1285 0.2576 0.055 Uiso 1 1 calc R . . C23 C 0.6257(5) 0.4395(6) 0.1895(5) 0.0339(19) Uani 1 1 d . . . H23 H 0.5710 0.4572 0.1749 0.041 Uiso 1 1 calc R . . N5 N 0.6438(4) 0.3491(5) 0.1865(4) 0.0304(15) Uani 1 1 d . . . C24 C 0.7207(5) 0.3270(6) 0.2053(5) 0.043(2) Uani 1 1 d . . . H24 H 0.7352 0.2625 0.2021 0.052 Uiso 1 1 calc R . . C25 C 0.8185(5) 0.0098(6) 0.2872(5) 0.038(2) Uani 1 1 d . . . H25 H 0.8351 0.0738 0.2858 0.045 Uiso 1 1 calc R . . C26 C 0.5504(4) 0.1412(6) -0.1071(4) 0.0298(18) Uani 1 1 d . . . C27 C 0.5807(6) 0.2013(6) -0.1574(5) 0.047(2) Uani 1 1 d . . . H27 H 0.6023 0.2608 -0.1386 0.057 Uiso 1 1 calc R . . C28 C 0.5799(6) 0.1749(7) -0.2361(5) 0.052(3) Uani 1 1 d . . . H28 H 0.6011 0.2162 -0.2701 0.062 Uiso 1 1 calc R . . C29 C 0.5490(5) 0.0911(7) -0.2628(5) 0.040(2) Uani 1 1 d . . . C30 C 0.5453(6) 0.0630(8) -0.3473(6) 0.055(3) Uani 1 1 d . . . F1 F 0.5635(4) -0.0283(5) -0.3538(3) 0.085(2) Uani 1 1 d . . . F2 F 0.4735(4) 0.0762(5) -0.3920(3) 0.088(2) Uani 1 1 d . . . F3 F 0.5953(4) 0.1106(5) -0.3815(3) 0.081(2) Uani 1 1 d . . . C31 C 0.5198(5) 0.0288(6) -0.2135(5) 0.037(2) Uani 1 1 d . . . H31 H 0.4998 -0.0314 -0.2322 0.045 Uiso 1 1 calc R . . C32 C 0.5203(5) 0.0555(6) -0.1379(5) 0.037(2) Uani 1 1 d . . . H32 H 0.4990 0.0133 -0.1047 0.044 Uiso 1 1 calc R . . C33 C 0.3445(4) 0.4820(6) 0.0646(4) 0.0286(18) Uani 1 1 d . . . C34 C 0.3686(5) 0.5593(6) 0.0274(5) 0.039(2) Uani 1 1 d . . . H34 H 0.4225 0.5634 0.0209 0.047 Uiso 1 1 calc R . . C35 C 0.3163(5) 0.6307(6) -0.0005(5) 0.043(2) Uani 1 1 d . . . H35 H 0.3356 0.6824 -0.0265 0.052 Uiso 1 1 calc R . . N6 N 0.2409(5) 0.6317(5) 0.0065(4) 0.0442(19) Uani 1 1 d . . . C36 C 0.2153(5) 0.5572(7) 0.0435(5) 0.044(2) Uani 1 1 d . . . H36 H 0.1609 0.5561 0.0490 0.053 Uiso 1 1 calc R . . C37 C 0.2642(5) 0.4823(6) 0.0739(5) 0.040(2) Uani 1 1 d . . . H37 H 0.2439 0.4319 0.1006 0.048 Uiso 1 1 calc R . . C38 C 0.4989(5) 0.2942(6) 0.4373(4) 0.0312(19) Uani 1 1 d . . . C39 C 0.5518(5) 0.3443(7) 0.4918(5) 0.045(2) Uani 1 1 d . . . H39 H 0.6014 0.3638 0.4799 0.054 Uiso 1 1 calc R . . C40 C 0.5334(6) 0.3676(7) 0.5658(5) 0.054(3) Uani 1 1 d . . . H40 H 0.5695 0.4040 0.6030 0.065 Uiso 1 1 calc R . . C41 C 0.4630(5) 0.3368(6) 0.5827(5) 0.043(2) Uani 1 1 d . . . C42 C 0.4399(8) 0.3697(8) 0.6570(7) 0.063(3) Uani 1 1 d . . . F4 F 0.4033(5) 0.4536(6) 0.6491(4) 0.102(3) Uani 1 1 d . . . F5 F 0.3925(5) 0.3095(5) 0.6839(4) 0.106(3) Uani 1 1 d . . . F6 F 0.5010(4) 0.3807(5) 0.7170(3) 0.086(2) Uani 1 1 d . . . C43 C 0.4089(6) 0.2850(7) 0.5300(5) 0.050(3) Uani 1 1 d . . . H43 H 0.3598 0.2643 0.5424 0.060 Uiso 1 1 calc R . . C44 C 0.4290(6) 0.2640(7) 0.4573(5) 0.049(2) Uani 1 1 d . . . H44 H 0.3928 0.2273 0.4202 0.059 Uiso 1 1 calc R . . C45 C 0.8041(10) 0.3562(12) 0.6692(10) 0.1284(9) Uani 1 1 d . . . H45 H 0.8636 0.3596 0.6860 0.154 Uiso 1 1 calc R . . Cl1 Cl 0.7659(3) 0.4715(3) 0.6630(3) 0.1284(9) Uani 1 1 d . . . Cl2 Cl 0.7805(2) 0.3081(3) 0.5708(3) 0.1284(9) Uani 1 1 d . . . Cl3 Cl 0.7679(3) 0.2901(3) 0.7350(3) 0.1284(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0317(5) 0.0246(5) 0.0277(4) -0.0004(5) 0.0060(3) 0.0000(5) N1 0.042(4) 0.022(3) 0.027(4) -0.004(3) 0.009(3) 0.004(3) N2 0.034(4) 0.033(4) 0.021(3) -0.001(3) 0.006(3) 0.001(3) N3 0.028(3) 0.026(3) 0.032(4) -0.006(3) 0.011(3) 0.006(3) N4 0.030(4) 0.034(4) 0.026(4) 0.002(3) 0.007(3) 0.002(3) C1 0.033(5) 0.038(5) 0.030(5) 0.003(4) 0.003(4) 0.002(4) C2 0.039(5) 0.045(5) 0.032(5) 0.002(4) 0.008(4) 0.002(4) C3 0.041(5) 0.040(5) 0.029(5) 0.005(4) 0.001(4) 0.010(4) C4 0.037(5) 0.026(4) 0.031(4) 0.004(4) 0.005(4) 0.007(4) C5 0.037(5) 0.025(4) 0.031(4) 0.000(4) -0.001(4) 0.005(4) C6 0.030(4) 0.028(4) 0.030(4) 0.008(4) 0.008(3) 0.001(4) C7 0.042(5) 0.036(5) 0.044(6) 0.002(4) 0.014(4) 0.009(4) C8 0.065(6) 0.032(5) 0.028(5) -0.008(4) 0.016(4) 0.011(5) C9 0.039(5) 0.025(4) 0.032(5) -0.006(4) 0.003(4) -0.006(4) C10 0.037(5) 0.037(5) 0.025(4) 0.000(4) 0.009(4) -0.003(4) C11 0.038(4) 0.023(4) 0.028(4) -0.002(4) 0.004(3) 0.008(4) C12 0.043(5) 0.046(5) 0.023(4) 0.003(4) 0.003(4) 0.007(4) C13 0.045(5) 0.042(5) 0.035(5) 0.019(4) 0.007(4) 0.019(4) C14 0.032(4) 0.033(5) 0.034(5) 0.000(4) 0.006(4) 0.007(4) C15 0.029(4) 0.024(4) 0.033(5) -0.002(4) 0.004(3) 0.001(4) C16 0.028(4) 0.024(4) 0.033(5) -0.003(4) 0.007(3) 0.004(3) C17 0.043(5) 0.033(5) 0.035(5) -0.004(4) 0.011(4) 0.007(4) C18 0.050(5) 0.035(5) 0.034(5) -0.006(4) 0.013(4) 0.013(4) C19 0.039(5) 0.033(5) 0.032(5) -0.003(4) 0.014(4) -0.001(4) C20 0.029(4) 0.033(5) 0.034(5) 0.003(4) 0.007(3) -0.001(4) C21 0.038(5) 0.028(5) 0.028(5) 0.005(4) 0.008(4) 0.010(4) C22 0.033(5) 0.031(5) 0.072(7) 0.000(5) 0.002(5) 0.001(4) C23 0.033(5) 0.028(4) 0.040(5) 0.000(4) 0.004(4) 0.000(4) N5 0.027(4) 0.031(4) 0.031(4) -0.002(3) 0.001(3) 0.003(3) C24 0.037(5) 0.026(5) 0.063(6) 0.002(4) 0.000(4) 0.001(4) C25 0.041(5) 0.032(5) 0.038(5) 0.002(4) 0.002(4) -0.006(4) C26 0.027(4) 0.032(5) 0.030(4) -0.001(4) 0.007(3) 0.004(4) C27 0.073(7) 0.033(5) 0.043(5) -0.009(4) 0.027(5) -0.014(5) C28 0.076(7) 0.049(6) 0.036(5) 0.000(5) 0.022(5) -0.013(5) C29 0.046(5) 0.044(6) 0.031(5) -0.011(4) 0.008(4) -0.003(5) C30 0.062(7) 0.053(6) 0.050(7) -0.008(6) 0.015(6) -0.003(6) F1 0.144(6) 0.067(4) 0.055(4) -0.021(3) 0.044(4) 0.004(4) F2 0.085(5) 0.133(7) 0.040(4) -0.020(4) -0.001(3) 0.000(4) F3 0.103(5) 0.103(5) 0.049(4) -0.017(4) 0.046(3) -0.026(4) C31 0.037(5) 0.045(6) 0.031(5) -0.014(4) 0.010(4) -0.006(4) C32 0.038(5) 0.040(5) 0.034(5) 0.005(4) 0.011(4) -0.003(4) C33 0.031(4) 0.030(4) 0.025(4) -0.005(4) 0.007(3) 0.005(4) C34 0.041(5) 0.035(5) 0.042(5) 0.001(4) 0.009(4) 0.002(4) C35 0.052(6) 0.036(5) 0.041(5) 0.005(4) 0.006(4) 0.018(5) N6 0.053(5) 0.032(4) 0.045(5) 0.007(4) 0.006(4) 0.013(4) C36 0.038(5) 0.046(6) 0.050(6) 0.006(5) 0.011(4) 0.013(5) C37 0.036(5) 0.035(5) 0.048(6) 0.001(4) 0.008(4) 0.005(4) C38 0.040(5) 0.028(4) 0.027(4) -0.001(4) 0.010(4) -0.001(4) C39 0.040(5) 0.059(6) 0.041(5) -0.016(5) 0.019(4) -0.007(5) C40 0.055(6) 0.065(7) 0.040(6) -0.016(5) 0.005(5) -0.015(5) C41 0.051(6) 0.046(6) 0.038(5) -0.011(5) 0.023(4) -0.011(5) C42 0.085(8) 0.055(7) 0.056(7) -0.012(6) 0.030(6) -0.007(7) F4 0.138(7) 0.112(6) 0.072(5) -0.011(4) 0.058(4) 0.044(5) F5 0.150(7) 0.115(6) 0.079(5) -0.040(4) 0.082(5) -0.072(5) F6 0.125(6) 0.095(5) 0.042(4) -0.020(4) 0.024(4) -0.013(5) C43 0.049(6) 0.058(6) 0.048(6) -0.011(5) 0.021(5) -0.020(5) C44 0.066(6) 0.044(6) 0.040(5) -0.010(5) 0.014(4) -0.021(5) C45 0.1223(19) 0.1074(19) 0.162(2) 0.0236(17) 0.0431(17) 0.0190(15) Cl1 0.1223(19) 0.1074(19) 0.162(2) 0.0236(17) 0.0431(17) 0.0190(15) Cl2 0.1223(19) 0.1074(19) 0.162(2) 0.0236(17) 0.0431(17) 0.0190(15) Cl3 0.1223(19) 0.1074(19) 0.162(2) 0.0236(17) 0.0431(17) 0.0190(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.052(6) . ? Zn1 N4 2.065(6) . ? Zn1 N3 2.075(6) . ? Zn1 N1 2.079(6) . ? Zn1 N5 2.134(6) . ? N1 C4 1.377(9) . ? N1 C1 1.389(10) . ? N2 C6 1.384(9) . ? N2 C9 1.388(9) . ? N3 C11 1.353(9) . ? N3 C14 1.377(9) . ? N4 C19 1.382(9) . ? N4 C16 1.389(9) . ? C1 C20 1.375(11) . ? C1 C2 1.445(11) . ? C2 C3 1.352(11) . ? C2 H2 0.9500 . ? C3 C4 1.441(10) . ? C3 H3 0.9500 . ? C4 C5 1.388(11) . ? C5 C6 1.398(10) . ? C5 C21 1.500(10) . ? C6 C7 1.426(11) . ? C7 C8 1.331(11) . ? C7 H7 0.9500 . ? C8 C9 1.447(11) . ? C8 H8 0.9500 . ? C9 C10 1.413(11) . ? C10 C11 1.385(10) . ? C10 C26 1.505(10) . ? C11 C12 1.447(10) . ? C12 C13 1.364(11) . ? C12 H12 0.9500 . ? C13 C14 1.426(10) . ? C13 H13 0.9500 . ? C14 C15 1.415(10) . ? C15 C16 1.387(10) . ? C15 C33 1.489(10) . ? C16 C17 1.431(10) . ? C17 C18 1.343(11) . ? C17 H17 0.9500 . ? C18 C19 1.422(11) . ? C18 H18 0.9500 . ? C19 C20 1.425(11) . ? C20 C38 1.498(10) . ? C21 C25 1.381(11) . ? C21 C22 1.388(11) . ? C22 C24 1.374(11) 2_645 ? C22 H22 0.9500 . ? C23 N5 1.318(9) . ? C23 C25 1.379(11) 2_655 ? C23 H23 0.9500 . ? N5 C24 1.325(9) . ? C24 C22 1.374(11) 2_655 ? C24 H24 0.9500 . ? C25 C23 1.379(11) 2_645 ? C25 H25 0.9500 . ? C26 C32 1.381(11) . ? C26 C27 1.386(11) . ? C27 C28 1.407(11) . ? C27 H27 0.9500 . ? C28 C29 1.340(12) . ? C28 H28 0.9500 . ? C29 C31 1.384(12) . ? C29 C30 1.504(12) . ? C30 F3 1.315(11) . ? C30 F2 1.324(11) . ? C30 F1 1.337(11) . ? C31 C32 1.360(10) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.371(11) . ? C33 C37 1.409(10) . ? C34 C35 1.369(11) . ? C34 H34 0.9500 . ? C35 N6 1.315(10) . ? C35 H35 0.9500 . ? N6 C36 1.348(11) . ? C36 C37 1.385(11) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C39 1.366(11) . ? C38 C44 1.373(11) . ? C39 C40 1.414(11) . ? C39 H39 0.9500 . ? C40 C41 1.361(12) . ? C40 H40 0.9500 . ? C41 C43 1.373(12) . ? C41 C42 1.491(12) . ? C42 F5 1.321(12) . ? C42 F6 1.326(12) . ? C42 F4 1.335(12) . ? C43 C44 1.399(12) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 Cl3 1.682(16) . ? C45 Cl1 1.751(16) . ? C45 Cl2 1.802(17) . ? C45 H45 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N4 158.9(2) . . ? N2 Zn1 N3 88.5(2) . . ? N4 Zn1 N3 88.6(2) . . ? N2 Zn1 N1 88.4(2) . . ? N4 Zn1 N1 88.4(2) . . ? N3 Zn1 N1 163.1(2) . . ? N2 Zn1 N5 102.6(2) . . ? N4 Zn1 N5 98.5(2) . . ? N3 Zn1 N5 102.0(2) . . ? N1 Zn1 N5 94.8(2) . . ? C4 N1 C1 107.2(6) . . ? C4 N1 Zn1 125.9(5) . . ? C1 N1 Zn1 126.3(5) . . ? C6 N2 C9 105.0(6) . . ? C6 N2 Zn1 127.4(5) . . ? C9 N2 Zn1 126.9(5) . . ? C11 N3 C14 107.1(6) . . ? C11 N3 Zn1 127.4(5) . . ? C14 N3 Zn1 125.5(5) . . ? C19 N4 C16 105.3(6) . . ? C19 N4 Zn1 126.5(5) . . ? C16 N4 Zn1 125.6(5) . . ? C20 C1 N1 125.6(7) . . ? C20 C1 C2 126.1(8) . . ? N1 C1 C2 108.4(7) . . ? C3 C2 C1 107.9(7) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? C2 C3 C4 107.4(7) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C5 124.3(7) . . ? N1 C4 C3 109.2(7) . . ? C5 C4 C3 126.5(7) . . ? C4 C5 C6 128.2(7) . . ? C4 C5 C21 116.7(7) . . ? C6 C5 C21 115.1(7) . . ? N2 C6 C5 123.1(7) . . ? N2 C6 C7 110.0(7) . . ? C5 C6 C7 127.0(7) . . ? C8 C7 C6 108.4(7) . . ? C8 C7 H7 125.8 . . ? C6 C7 H7 125.8 . . ? C7 C8 C9 106.7(7) . . ? C7 C8 H8 126.6 . . ? C9 C8 H8 126.6 . . ? N2 C9 C10 124.6(7) . . ? N2 C9 C8 109.8(7) . . ? C10 C9 C8 125.5(7) . . ? C11 C10 C9 125.8(7) . . ? C11 C10 C26 117.8(7) . . ? C9 C10 C26 116.4(7) . . ? N3 C11 C10 125.8(7) . . ? N3 C11 C12 110.0(7) . . ? C10 C11 C12 124.2(7) . . ? C13 C12 C11 106.0(7) . . ? C13 C12 H12 127.0 . . ? C11 C12 H12 127.0 . . ? C12 C13 C14 107.7(7) . . ? C12 C13 H13 126.2 . . ? C14 C13 H13 126.2 . . ? N3 C14 C15 125.9(7) . . ? N3 C14 C13 109.3(7) . . ? C15 C14 C13 124.8(7) . . ? C16 C15 C14 125.4(7) . . ? C16 C15 C33 118.8(7) . . ? C14 C15 C33 115.8(7) . . ? C15 C16 N4 125.1(7) . . ? C15 C16 C17 125.1(7) . . ? N4 C16 C17 109.8(7) . . ? C18 C17 C16 107.0(7) . . ? C18 C17 H17 126.5 . . ? C16 C17 H17 126.5 . . ? C17 C18 C19 108.0(7) . . ? C17 C18 H18 126.0 . . ? C19 C18 H18 126.0 . . ? N4 C19 C18 109.8(7) . . ? N4 C19 C20 124.7(7) . . ? C18 C19 C20 125.5(7) . . ? C1 C20 C19 126.0(7) . . ? C1 C20 C38 118.8(7) . . ? C19 C20 C38 115.2(7) . . ? C25 C21 C22 116.6(7) . . ? C25 C21 C5 120.0(7) . . ? C22 C21 C5 123.4(7) . . ? C24 C22 C21 119.3(8) 2_645 . ? C24 C22 H22 120.4 2_645 . ? C21 C22 H22 120.4 . . ? N5 C23 C25 123.9(8) . 2_655 ? N5 C23 H23 118.1 . . ? C25 C23 H23 118.1 2_655 . ? C23 N5 C24 116.5(7) . . ? C23 N5 Zn1 120.2(5) . . ? C24 N5 Zn1 122.8(6) . . ? N5 C24 C22 124.1(8) . 2_655 ? N5 C24 H24 117.9 . . ? C22 C24 H24 117.9 2_655 . ? C23 C25 C21 119.6(8) 2_645 . ? C23 C25 H25 120.2 2_645 . ? C21 C25 H25 120.2 . . ? C32 C26 C27 116.9(7) . . ? C32 C26 C10 122.5(7) . . ? C27 C26 C10 120.6(7) . . ? C26 C27 C28 120.6(8) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C29 C28 C27 119.7(9) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C31 120.9(8) . . ? C28 C29 C30 120.5(9) . . ? C31 C29 C30 118.6(8) . . ? F3 C30 F2 105.8(9) . . ? F3 C30 F1 105.9(9) . . ? F2 C30 F1 106.8(9) . . ? F3 C30 C29 113.3(8) . . ? F2 C30 C29 112.7(8) . . ? F1 C30 C29 111.8(8) . . ? C32 C31 C29 118.7(8) . . ? C32 C31 H31 120.6 . . ? C29 C31 H31 120.6 . . ? C31 C32 C26 123.1(8) . . ? C31 C32 H32 118.5 . . ? C26 C32 H32 118.5 . . ? C34 C33 C37 116.0(8) . . ? C34 C33 C15 122.9(7) . . ? C37 C33 C15 121.0(7) . . ? C35 C34 C33 121.2(8) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? N6 C35 C34 123.7(9) . . ? N6 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? C35 N6 C36 116.7(8) . . ? N6 C36 C37 123.3(8) . . ? N6 C36 H36 118.3 . . ? C37 C36 H36 118.3 . . ? C36 C37 C33 119.0(8) . . ? C36 C37 H37 120.5 . . ? C33 C37 H37 120.5 . . ? C39 C38 C44 118.4(8) . . ? C39 C38 C20 122.1(7) . . ? C44 C38 C20 119.4(7) . . ? C38 C39 C40 120.6(8) . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C41 C40 C39 118.8(8) . . ? C41 C40 H40 120.6 . . ? C39 C40 H40 120.6 . . ? C40 C41 C43 122.2(8) . . ? C40 C41 C42 118.7(9) . . ? C43 C41 C42 118.7(9) . . ? F5 C42 F6 103.9(9) . . ? F5 C42 F4 107.7(10) . . ? F6 C42 F4 104.8(9) . . ? F5 C42 C41 112.7(9) . . ? F6 C42 C41 114.2(10) . . ? F4 C42 C41 112.8(9) . . ? C41 C43 C44 117.2(8) . . ? C41 C43 H43 121.4 . . ? C44 C43 H43 121.4 . . ? C38 C44 C43 122.6(8) . . ? C38 C44 H44 118.7 . . ? C43 C44 H44 118.7 . . ? Cl3 C45 Cl1 112.1(9) . . ? Cl3 C45 Cl2 112.7(10) . . ? Cl1 C45 Cl2 106.4(9) . . ? Cl3 C45 H45 108.5 . . ? Cl1 C45 H45 108.5 . . ? Cl2 C45 H45 108.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.663 _refine_diff_density_min -1.610 _refine_diff_density_rms 0.134 # Attachment 'ESI_14.cif' data_e1318a _database_code_depnum_ccdc_archive 'CCDC 701452' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 N6 O4, 3 (C H Cl3)' _chemical_formula_sum 'C49 H35 Cl9 N6 O4' _chemical_formula_weight 1090.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 9.7555(2) _cell_length_b 13.5546(3) _cell_length_c 20.0154(4) _cell_angle_alpha 78.3190(10) _cell_angle_beta 76.7100(10) _cell_angle_gamma 77.1790(10) _cell_volume 2479.38(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7544 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8283 _exptl_absorpt_correction_T_max 0.9060 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40250 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.56 _reflns_number_total 11316 _reflns_number_gt 7811 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1016P)^2^+6.5219P] 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 11316 _refine_ls_number_parameters 615 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2310 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.9360(3) 0.4249(2) 0.91121(15) 0.0203(6) Uani 1 1 d . . . H1 H 0.9760 0.3682 0.9349 0.024 Uiso 1 1 calc R . . N2 N 0.9036(3) 0.3336(2) 1.05665(16) 0.0210(6) Uani 1 1 d . . . N3 N 1.0885(3) 0.1456(2) 1.01799(15) 0.0204(6) Uani 1 1 d . . . H3 H 1.0518 0.2040 0.9946 0.025 Uiso 1 1 calc R . . N4 N 1.1367(3) 0.2414(2) 0.87288(15) 0.0200(6) Uani 1 1 d . . . C1 C 0.9667(4) 0.4544(3) 0.84081(19) 0.0224(7) Uani 1 1 d . . . C2 C 0.8783(4) 0.5528(3) 0.82236(19) 0.0241(8) Uani 1 1 d . . . H2 H 0.8794 0.5910 0.7769 0.029 Uiso 1 1 calc R . . C3 C 0.7938(4) 0.5800(3) 0.8819(2) 0.0242(8) Uani 1 1 d . . . H3A H 0.7231 0.6403 0.8862 0.029 Uiso 1 1 calc R . . C4 C 0.8316(4) 0.5000(3) 0.93799(18) 0.0192(7) Uani 1 1 d . . . C5 C 0.7719(4) 0.5006(3) 1.00848(19) 0.0206(7) Uani 1 1 d . . . C6 C 0.8107(4) 0.4250(3) 1.06304(19) 0.0210(7) Uani 1 1 d . . . C7 C 0.7585(4) 0.4296(3) 1.13598(19) 0.0244(8) Uani 1 1 d . . . H7 H 0.6938 0.4847 1.1553 0.029 Uiso 1 1 calc R . . C8 C 0.8183(4) 0.3411(3) 1.17187(19) 0.0248(8) Uani 1 1 d . . . H8 H 0.8034 0.3229 1.2210 0.030 Uiso 1 1 calc R . . C9 C 0.9081(4) 0.2797(3) 1.12241(18) 0.0199(7) Uani 1 1 d . . . C10 C 0.9811(4) 0.1790(3) 1.13818(18) 0.0200(7) Uani 1 1 d . . . C11 C 1.0647(4) 0.1183(3) 1.08885(18) 0.0203(7) Uani 1 1 d . . . C12 C 1.1419(4) 0.0160(3) 1.10622(19) 0.0252(8) Uani 1 1 d . . . H12 H 1.1429 -0.0215 1.1517 0.030 Uiso 1 1 calc R . . C13 C 1.2130(4) -0.0170(3) 1.04607(19) 0.0252(8) Uani 1 1 d . . . H13 H 1.2730 -0.0817 1.0412 0.030 Uiso 1 1 calc R . . C14 C 1.1798(4) 0.0655(3) 0.99053(18) 0.0196(7) Uani 1 1 d . . . C15 C 1.2420(4) 0.0650(3) 0.91976(18) 0.0201(7) Uani 1 1 d . . . C16 C 1.2221(4) 0.1471(3) 0.86554(19) 0.0211(7) Uani 1 1 d . . . C17 C 1.2848(4) 0.1477(3) 0.79294(19) 0.0240(8) Uani 1 1 d . . . H17 H 1.3479 0.0923 0.7731 0.029 Uiso 1 1 calc R . . C18 C 1.2380(4) 0.2410(3) 0.75813(19) 0.0245(8) Uani 1 1 d . . . H18 H 1.2627 0.2632 0.7095 0.029 Uiso 1 1 calc R . . C19 C 1.1436(4) 0.3007(3) 0.80812(18) 0.0209(7) Uani 1 1 d . . . C20 C 1.0665(4) 0.3996(3) 0.79262(18) 0.0209(7) Uani 1 1 d . . . C21 C 0.6554(4) 0.5878(3) 1.02831(18) 0.0211(7) Uani 1 1 d . . . C22 C 0.5190(4) 0.5716(3) 1.0625(2) 0.0259(8) Uani 1 1 d . . . H22 H 0.4974 0.5045 1.0720 0.031 Uiso 1 1 calc R . . C23 C 0.4150(4) 0.6531(3) 1.0826(2) 0.0295(8) Uani 1 1 d . . . H23 H 0.3229 0.6400 1.1060 0.035 Uiso 1 1 calc R . . N6 N 0.4373(4) 0.7500(3) 1.07088(18) 0.0306(7) Uani 1 1 d . . . C24 C 0.5677(4) 0.7650(3) 1.0366(2) 0.0276(8) Uani 1 1 d . . . H24 H 0.5855 0.8331 1.0267 0.033 Uiso 1 1 calc R . . C25 C 0.6785(4) 0.6885(3) 1.0146(2) 0.0247(8) Uani 1 1 d . . . H25 H 0.7689 0.7042 0.9905 0.030 Uiso 1 1 calc R . . C26 C 0.9616(4) 0.1307(3) 1.21288(18) 0.0222(7) Uani 1 1 d . . . C27 C 0.8938(4) 0.0466(3) 1.23573(19) 0.0257(8) Uani 1 1 d . . . H27 H 0.8649 0.0175 1.2030 0.031 Uiso 1 1 calc R . . C28 C 0.8674(4) 0.0042(3) 1.3057(2) 0.0298(8) Uani 1 1 d . . . H28 H 0.8213 -0.0534 1.3210 0.036 Uiso 1 1 calc R . . C29 C 0.9096(4) 0.0475(3) 1.35258(19) 0.0286(8) Uani 1 1 d . . . O1 O 0.8879(3) 0.0016(2) 1.42313(14) 0.0370(7) Uani 1 1 d . . . C32 C 0.7807(6) 0.0496(4) 1.4677(2) 0.0485(13) Uani 1 1 d . . . O2 O 0.7079(6) 0.1276(4) 1.4489(2) 0.110(2) Uani 1 1 d . . . C33 C 0.7706(7) -0.0062(5) 1.5403(2) 0.0574(15) Uani 1 1 d . . . H33A H 0.8125 0.0283 1.5671 0.086 Uiso 1 1 calc R . . H33B H 0.8230 -0.0768 1.5398 0.086 Uiso 1 1 calc R . . H33C H 0.6698 -0.0069 1.5617 0.086 Uiso 1 1 calc R . . C30 C 0.9783(5) 0.1295(3) 1.3320(2) 0.0308(9) Uani 1 1 d . . . H30 H 1.0070 0.1577 1.3652 0.037 Uiso 1 1 calc R . . C31 C 1.0059(4) 0.1710(3) 1.2616(2) 0.0275(8) Uani 1 1 d . . . H31 H 1.0551 0.2271 1.2467 0.033 Uiso 1 1 calc R . . C34 C 1.3443(4) -0.0305(3) 0.90149(18) 0.0211(7) Uani 1 1 d . . . C35 C 1.3015(4) -0.1247(3) 0.9148(2) 0.0236(7) Uani 1 1 d . . . H35 H 1.2061 -0.1308 0.9373 0.028 Uiso 1 1 calc R . . C36 C 1.3989(4) -0.2094(3) 0.8950(2) 0.0282(8) Uani 1 1 d . . . H36 H 1.3677 -0.2734 0.9051 0.034 Uiso 1 1 calc R . . N7 N 1.5343(4) -0.2070(3) 0.86253(18) 0.0316(8) Uani 1 1 d . . . C37 C 1.5752(4) -0.1166(3) 0.8516(2) 0.0332(9) Uani 1 1 d . . . H37 H 1.6718 -0.1130 0.8297 0.040 Uiso 1 1 calc R . . C38 C 1.4863(4) -0.0278(3) 0.8701(2) 0.0287(8) Uani 1 1 d . . . H38 H 1.5218 0.0344 0.8614 0.034 Uiso 1 1 calc R . . C39 C 1.0871(4) 0.4513(3) 0.71809(18) 0.0236(8) Uani 1 1 d . . . C40 C 0.9847(5) 0.4586(3) 0.6787(2) 0.0320(9) Uani 1 1 d . . . H40 H 0.9027 0.4281 0.6985 0.038 Uiso 1 1 calc R . . C41 C 1.0003(5) 0.5102(3) 0.6105(2) 0.0377(10) Uani 1 1 d . . . H41 H 0.9302 0.5142 0.5835 0.045 Uiso 1 1 calc R . . C42 C 1.1175(5) 0.5549(3) 0.5828(2) 0.0321(9) Uani 1 1 d . . . O3 O 1.1354(4) 0.6035(2) 0.51302(15) 0.0440(8) Uani 1 1 d . . . C45 C 1.0697(5) 0.7028(3) 0.4998(2) 0.0310(9) Uani 1 1 d . . . O4 O 1.0019(4) 0.7487(2) 0.54493(16) 0.0468(8) Uani 1 1 d . . . C46 C 1.0916(6) 0.7407(4) 0.4238(2) 0.0470(12) Uani 1 1 d . . . H46A H 1.0366 0.7078 0.4024 0.070 Uiso 1 1 calc R . . H46B H 1.1937 0.7242 0.4032 0.070 Uiso 1 1 calc R . . H46C H 1.0591 0.8152 0.4157 0.070 Uiso 1 1 calc R . . C43 C 1.2210(5) 0.5486(4) 0.6205(2) 0.0440(11) Uani 1 1 d . . . H43 H 1.3025 0.5796 0.6004 0.053 Uiso 1 1 calc R . . C44 C 1.2057(5) 0.4966(4) 0.6882(2) 0.0366(10) Uani 1 1 d . . . H44 H 1.2773 0.4920 0.7144 0.044 Uiso 1 1 calc R . . C47 C 0.3036(5) 0.7940(3) 0.2278(2) 0.0353(9) Uani 1 1 d . . . H47 H 0.3540 0.8134 0.1789 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.40553(16) 0.68107(10) 0.26545(8) 0.0575(4) Uani 1 1 d . . . Cl2 Cl 0.28867(14) 0.89460(9) 0.27365(6) 0.0422(3) Uani 1 1 d . . . Cl3 Cl 0.13426(13) 0.77304(9) 0.22555(7) 0.0476(3) Uani 1 1 d . . . C48 C 0.4384(6) 0.2721(5) 0.5146(3) 0.0622(16) Uani 1 1 d . . . H48 H 0.5132 0.2342 0.4809 0.075 Uiso 1 1 calc R . . Cl4 Cl 0.5141(3) 0.2896(3) 0.57961(13) 0.1262(10) Uani 1 1 d . . . Cl5 Cl 0.3002(4) 0.2101(3) 0.54312(17) 0.1649(15) Uani 1 1 d . . . Cl6 Cl 0.43239(16) 0.77564(14) 0.67884(10) 0.0811(6) Uani 1 1 d . . . C49 C 0.5745(5) 0.7043(4) 0.7172(2) 0.0412(11) Uani 1 1 d . . . H49 H 0.5649 0.7244 0.7637 0.049 Uiso 1 1 calc R . . Cl7 Cl 0.57186(15) 0.57201(10) 0.72864(8) 0.0576(4) Uani 1 1 d . . . Cl8 Cl 0.73867(14) 0.72846(11) 0.66525(7) 0.0554(4) Uani 1 1 d . . . Cl9 Cl 0.3723(3) 0.3986(2) 0.47120(13) 0.1223(10) 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 N1 0.0229(15) 0.0156(14) 0.0192(15) -0.0002(11) -0.0051(12) 0.0020(11) N2 0.0221(15) 0.0165(14) 0.0218(16) 0.0000(12) -0.0047(12) -0.0003(11) N3 0.0204(14) 0.0174(14) 0.0198(15) -0.0002(12) -0.0017(12) -0.0004(11) N4 0.0210(14) 0.0173(14) 0.0191(15) -0.0014(12) -0.0044(12) 0.0011(11) C1 0.0257(18) 0.0181(17) 0.0219(18) -0.0003(14) -0.0044(15) -0.0038(14) C2 0.0318(19) 0.0185(17) 0.0175(18) 0.0030(14) -0.0045(15) -0.0009(15) C3 0.0265(18) 0.0165(17) 0.0262(19) -0.0012(14) -0.0063(15) 0.0022(14) C4 0.0223(17) 0.0148(16) 0.0193(17) -0.0008(13) -0.0056(14) -0.0013(13) C5 0.0218(17) 0.0166(16) 0.0218(18) -0.0025(14) -0.0028(14) -0.0021(13) C6 0.0222(17) 0.0166(17) 0.0236(18) -0.0045(14) -0.0018(14) -0.0036(13) C7 0.0285(19) 0.0196(18) 0.0221(19) -0.0051(14) -0.0008(15) -0.0008(15) C8 0.0290(19) 0.0268(19) 0.0164(17) -0.0035(15) -0.0029(15) -0.0024(15) C9 0.0204(17) 0.0171(17) 0.0206(18) -0.0011(14) -0.0048(14) -0.0014(13) C10 0.0244(17) 0.0191(17) 0.0167(17) -0.0002(13) -0.0048(14) -0.0063(14) C11 0.0227(17) 0.0186(17) 0.0179(17) 0.0001(13) -0.0043(14) -0.0024(14) C12 0.0306(19) 0.0213(18) 0.0189(18) 0.0023(14) -0.0072(15) 0.0023(15) C13 0.0290(19) 0.0183(17) 0.0241(19) 0.0012(14) -0.0069(16) 0.0020(14) C14 0.0182(16) 0.0155(16) 0.0225(18) -0.0011(14) -0.0035(14) 0.0004(13) C15 0.0200(17) 0.0162(16) 0.0224(18) -0.0015(14) -0.0037(14) -0.0019(13) C16 0.0223(17) 0.0181(17) 0.0219(18) -0.0043(14) -0.0040(14) -0.0007(13) C17 0.0270(18) 0.0212(18) 0.0199(18) -0.0033(14) -0.0014(15) -0.0002(15) C18 0.0300(19) 0.0241(18) 0.0151(17) -0.0009(14) -0.0010(15) -0.0020(15) C19 0.0221(17) 0.0224(18) 0.0172(17) -0.0022(14) -0.0034(14) -0.0036(14) C20 0.0250(18) 0.0203(17) 0.0167(17) -0.0018(14) -0.0036(14) -0.0041(14) C21 0.0252(18) 0.0186(17) 0.0189(17) -0.0048(14) -0.0057(14) -0.0001(14) C22 0.0243(18) 0.0207(18) 0.031(2) -0.0051(16) -0.0029(16) -0.0022(15) C23 0.0237(19) 0.031(2) 0.032(2) -0.0113(17) 0.0010(16) -0.0010(16) N6 0.0348(19) 0.0246(17) 0.0310(18) -0.0099(14) -0.0071(15) 0.0032(14) C24 0.036(2) 0.0160(17) 0.031(2) -0.0036(15) -0.0113(17) -0.0007(15) C25 0.0281(19) 0.0221(18) 0.0245(19) -0.0036(15) -0.0058(15) -0.0048(15) C26 0.0249(18) 0.0209(18) 0.0164(17) -0.0017(14) -0.0023(14) 0.0018(14) C27 0.034(2) 0.0227(18) 0.0207(19) -0.0007(15) -0.0076(16) -0.0067(16) C28 0.037(2) 0.0236(19) 0.026(2) 0.0028(16) -0.0049(17) -0.0075(16) C29 0.037(2) 0.0246(19) 0.0171(18) 0.0012(15) -0.0048(16) 0.0040(16) O1 0.0521(19) 0.0323(16) 0.0172(14) 0.0030(12) -0.0051(13) 0.0037(14) C32 0.046(3) 0.062(3) 0.024(2) 0.000(2) -0.004(2) 0.011(2) O2 0.095(4) 0.123(4) 0.040(2) 0.016(3) 0.014(2) 0.073(3) C33 0.069(4) 0.067(4) 0.022(2) 0.004(2) -0.004(2) 0.003(3) C30 0.041(2) 0.028(2) 0.024(2) -0.0071(16) -0.0101(17) -0.0019(17) C31 0.037(2) 0.0216(19) 0.024(2) -0.0016(15) -0.0093(16) -0.0039(16) C34 0.0232(17) 0.0205(17) 0.0185(17) -0.0046(14) -0.0055(14) 0.0010(14) C35 0.0256(18) 0.0186(17) 0.0265(19) -0.0024(15) -0.0066(15) -0.0033(14) C36 0.037(2) 0.0196(18) 0.030(2) -0.0053(16) -0.0110(17) -0.0033(16) N7 0.0323(18) 0.0250(17) 0.0347(19) -0.0097(15) -0.0071(15) 0.0055(14) C37 0.026(2) 0.028(2) 0.039(2) -0.0049(18) -0.0014(17) 0.0027(16) C38 0.0258(19) 0.0207(19) 0.035(2) -0.0023(16) 0.0003(16) -0.0031(15) C39 0.0288(19) 0.0203(18) 0.0173(18) -0.0015(14) -0.0016(15) 0.0002(15) C40 0.038(2) 0.032(2) 0.026(2) 0.0032(17) -0.0089(17) -0.0113(18) C41 0.050(3) 0.037(2) 0.024(2) 0.0018(18) -0.0127(19) -0.004(2) C42 0.046(2) 0.027(2) 0.0146(18) 0.0013(15) 0.0002(17) 0.0013(18) O3 0.065(2) 0.0321(16) 0.0175(14) 0.0041(12) 0.0041(14) 0.0076(15) C45 0.040(2) 0.026(2) 0.024(2) 0.0024(16) -0.0039(17) -0.0074(17) O4 0.072(2) 0.0333(17) 0.0308(17) -0.0066(14) -0.0102(16) 0.0017(16) C46 0.062(3) 0.039(3) 0.028(2) 0.0098(19) -0.006(2) -0.001(2) C43 0.043(3) 0.053(3) 0.030(2) 0.008(2) 0.002(2) -0.019(2) C44 0.038(2) 0.044(3) 0.026(2) 0.0038(18) -0.0062(18) -0.012(2) C47 0.042(2) 0.027(2) 0.035(2) -0.0021(18) -0.0045(19) -0.0080(18) Cl1 0.0618(8) 0.0418(7) 0.0692(9) -0.0100(6) -0.0277(7) 0.0066(6) Cl2 0.0595(7) 0.0370(6) 0.0314(6) -0.0074(4) -0.0006(5) -0.0186(5) Cl3 0.0501(7) 0.0396(6) 0.0568(8) 0.0064(5) -0.0205(6) -0.0183(5) C48 0.043(3) 0.095(5) 0.048(3) -0.027(3) -0.003(2) -0.002(3) Cl4 0.0901(15) 0.205(3) 0.1074(17) -0.0484(18) -0.0509(13) -0.0217(17) Cl5 0.145(3) 0.251(4) 0.133(2) -0.039(2) 0.0051(19) -0.133(3) Cl6 0.0446(8) 0.0802(11) 0.0836(12) 0.0247(9) 0.0009(8) 0.0127(7) C49 0.047(3) 0.042(3) 0.029(2) -0.0052(19) 0.001(2) -0.005(2) Cl7 0.0512(7) 0.0447(7) 0.0739(10) -0.0072(6) -0.0030(7) -0.0141(6) Cl8 0.0483(7) 0.0598(8) 0.0567(8) 0.0125(6) -0.0153(6) -0.0215(6) Cl9 0.145(2) 0.1059(17) 0.1018(16) -0.0398(14) -0.0430(16) 0.0466(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 N1 C1 1.366(5) . ? N1 C4 1.367(4) . ? N1 H1 0.8800 . ? N2 C6 1.373(4) . ? N2 C9 1.375(5) . ? N3 C14 1.365(4) . ? N3 C11 1.370(5) . ? N3 H3 0.8800 . ? N4 C19 1.376(5) . ? N4 C16 1.378(4) . ? C1 C20 1.403(5) . ? C1 C2 1.447(5) . ? C2 C3 1.352(5) . ? C2 H2 0.9500 . ? C3 C4 1.446(5) . ? C3 H3A 0.9500 . ? C4 C5 1.398(5) . ? C5 C6 1.396(5) . ? C5 C21 1.494(5) . ? C6 C7 1.441(5) . ? C7 C8 1.353(5) . ? C7 H7 0.9500 . ? C8 C9 1.432(5) . ? C8 H8 0.9500 . ? C9 C10 1.402(5) . ? C10 C11 1.406(5) . ? C10 C26 1.493(5) . ? C11 C12 1.439(5) . ? C12 C13 1.351(5) . ? C12 H12 0.9500 . ? C13 C14 1.446(5) . ? C13 H13 0.9500 . ? C14 C15 1.408(5) . ? C15 C16 1.402(5) . ? C15 C34 1.503(5) . ? C16 C17 1.440(5) . ? C17 C18 1.352(5) . ? C17 H17 0.9500 . ? C18 C19 1.441(5) . ? C18 H18 0.9500 . ? C19 C20 1.396(5) . ? C20 C39 1.503(5) . ? C21 C22 1.393(5) . ? C21 C25 1.394(5) . ? C22 C23 1.381(5) . ? C22 H22 0.9500 . ? C23 N6 1.344(5) . ? C23 H23 0.9500 . ? N6 C24 1.337(5) . ? C24 C25 1.380(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.390(5) . ? C26 C31 1.397(5) . ? C27 C28 1.390(5) . ? C27 H27 0.9500 . ? C28 C29 1.379(6) . ? C28 H28 0.9500 . ? C29 C30 1.368(6) . ? C29 O1 1.411(5) . ? O1 C32 1.348(6) . ? C32 O2 1.181(6) . ? C32 C33 1.487(7) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C30 C31 1.395(6) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C34 C35 1.386(5) . ? C34 C38 1.389(5) . ? C35 C36 1.380(5) . ? C35 H35 0.9500 . ? C36 N7 1.335(5) . ? C36 H36 0.9500 . ? N7 C37 1.334(5) . ? C37 C38 1.381(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C40 1.384(5) . ? C39 C44 1.387(6) . ? C40 C41 1.394(6) . ? C40 H40 0.9500 . ? C41 C42 1.365(6) . ? C41 H41 0.9500 . ? C42 C43 1.372(7) . ? C42 O3 1.408(5) . ? O3 C45 1.357(5) . ? C45 O4 1.188(5) . ? C45 C46 1.485(6) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C43 C44 1.386(6) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C47 Cl3 1.749(5) . ? C47 Cl2 1.755(4) . ? C47 Cl1 1.761(5) . ? C47 H47 1.0000 . ? C48 Cl5 1.675(7) . ? C48 Cl4 1.714(6) . ? C48 Cl9 1.810(7) . ? C48 H48 1.0000 . ? Cl6 C49 1.744(5) . ? C49 Cl8 1.756(5) . ? C49 Cl7 1.767(5) . ? C49 H49 1.0000 . ? 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 C1 N1 C4 107.4(3) . . ? C1 N1 H1 126.3 . . ? C4 N1 H1 126.3 . . ? C6 N2 C9 107.9(3) . . ? C14 N3 C11 107.2(3) . . ? C14 N3 H3 126.4 . . ? C11 N3 H3 126.4 . . ? C19 N4 C16 108.1(3) . . ? N1 C1 C20 126.6(3) . . ? N1 C1 C2 109.2(3) . . ? C20 C1 C2 124.2(3) . . ? C3 C2 C1 107.1(3) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 107.0(3) . . ? C2 C3 H3A 126.5 . . ? C4 C3 H3A 126.5 . . ? N1 C4 C5 125.6(3) . . ? N1 C4 C3 109.3(3) . . ? C5 C4 C3 125.1(3) . . ? C6 C5 C4 125.4(3) . . ? C6 C5 C21 116.2(3) . . ? C4 C5 C21 118.4(3) . . ? N2 C6 C5 126.2(3) . . ? N2 C6 C7 108.3(3) . . ? C5 C6 C7 125.5(3) . . ? C8 C7 C6 107.5(3) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 107.7(3) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? N2 C9 C10 125.6(3) . . ? N2 C9 C8 108.5(3) . . ? C10 C9 C8 125.7(3) . . ? C9 C10 C11 125.1(3) . . ? C9 C10 C26 117.3(3) . . ? C11 C10 C26 117.5(3) . . ? N3 C11 C10 126.8(3) . . ? N3 C11 C12 109.1(3) . . ? C10 C11 C12 124.2(3) . . ? C13 C12 C11 107.6(3) . . ? C13 C12 H12 126.2 . . ? C11 C12 H12 126.2 . . ? C12 C13 C14 106.6(3) . . ? C12 C13 H13 126.7 . . ? C14 C13 H13 126.7 . . ? N3 C14 C15 125.8(3) . . ? N3 C14 C13 109.5(3) . . ? C15 C14 C13 124.5(3) . . ? C16 C15 C14 125.9(3) . . ? C16 C15 C34 117.3(3) . . ? C14 C15 C34 116.8(3) . . ? N4 C16 C15 125.4(3) . . ? N4 C16 C17 108.1(3) . . ? C15 C16 C17 126.5(3) . . ? C18 C17 C16 107.8(3) . . ? C18 C17 H17 126.1 . . ? C16 C17 H17 126.1 . . ? C17 C18 C19 107.7(3) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? N4 C19 C20 126.1(3) . . ? N4 C19 C18 108.3(3) . . ? C20 C19 C18 125.6(3) . . ? C19 C20 C1 125.4(3) . . ? C19 C20 C39 118.1(3) . . ? C1 C20 C39 116.5(3) . . ? C22 C21 C25 117.0(3) . . ? C22 C21 C5 121.1(3) . . ? C25 C21 C5 121.9(3) . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? N6 C23 C22 123.5(4) . . ? N6 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C24 N6 C23 116.1(3) . . ? N6 C24 C25 124.6(4) . . ? N6 C24 H24 117.7 . . ? C25 C24 H24 117.7 . . ? C24 C25 C21 118.9(4) . . ? C24 C25 H25 120.5 . . ? C21 C25 H25 120.5 . . ? C27 C26 C31 118.6(3) . . ? C27 C26 C10 120.3(3) . . ? C31 C26 C10 121.0(3) . . ? C26 C27 C28 121.1(3) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 118.7(4) . . ? C29 C28 H28 120.7 . . ? C27 C28 H28 120.7 . . ? C30 C29 C28 121.9(4) . . ? C30 C29 O1 119.6(4) . . ? C28 C29 O1 118.4(4) . . ? C32 O1 C29 117.6(3) . . ? O2 C32 O1 121.5(4) . . ? O2 C32 C33 126.4(5) . . ? O1 C32 C33 112.1(4) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 C30 C31 119.2(4) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C30 C31 C26 120.4(4) . . ? C30 C31 H31 119.8 . . ? C26 C31 H31 119.8 . . ? C35 C34 C38 117.2(3) . . ? C35 C34 C15 121.8(3) . . ? C38 C34 C15 121.1(3) . . ? C36 C35 C34 119.4(4) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? N7 C36 C35 124.0(4) . . ? N7 C36 H36 118.0 . . ? C35 C36 H36 118.0 . . ? C37 N7 C36 116.1(3) . . ? N7 C37 C38 124.2(4) . . ? N7 C37 H37 117.9 . . ? C38 C37 H37 117.9 . . ? C37 C38 C34 119.2(4) . . ? C37 C38 H38 120.4 . . ? C34 C38 H38 120.4 . . ? C40 C39 C44 118.5(4) . . ? C40 C39 C20 120.6(3) . . ? C44 C39 C20 120.8(3) . . ? C39 C40 C41 120.9(4) . . ? C39 C40 H40 119.6 . . ? C41 C40 H40 119.6 . . ? C42 C41 C40 119.2(4) . . ? C42 C41 H41 120.4 . . ? C40 C41 H41 120.4 . . ? C41 C42 C43 121.3(4) . . ? C41 C42 O3 118.9(4) . . ? C43 C42 O3 119.8(4) . . ? C45 O3 C42 117.5(3) . . ? O4 C45 O3 122.1(4) . . ? O4 C45 C46 127.0(4) . . ? O3 C45 C46 110.8(4) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C42 C43 C44 119.4(4) . . ? C42 C43 H43 120.3 . . ? C44 C43 H43 120.3 . . ? C43 C44 C39 120.8(4) . . ? C43 C44 H44 119.6 . . ? C39 C44 H44 119.6 . . ? Cl3 C47 Cl2 110.8(3) . . ? Cl3 C47 Cl1 110.3(2) . . ? Cl2 C47 Cl1 110.4(2) . . ? Cl3 C47 H47 108.4 . . ? Cl2 C47 H47 108.4 . . ? Cl1 C47 H47 108.4 . . ? Cl5 C48 Cl4 113.9(4) . . ? Cl5 C48 Cl9 107.9(4) . . ? Cl4 C48 Cl9 106.5(4) . . ? Cl5 C48 H48 109.5 . . ? Cl4 C48 H48 109.5 . . ? Cl9 C48 H48 109.5 . . ? Cl6 C49 Cl8 110.4(3) . . ? Cl6 C49 Cl7 110.4(3) . . ? Cl8 C49 Cl7 109.2(3) . . ? Cl6 C49 H49 108.9 . . ? Cl8 C49 H49 108.9 . . ? Cl7 C49 H49 108.9 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.609 _refine_diff_density_min -1.333 _refine_diff_density_rms 0.093 # Attachment 'ESI_16.cif' data_e883a _database_code_depnum_ccdc_archive 'CCDC 701453' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H26 F6 N6' _chemical_formula_weight 752.71 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.844(16) _cell_length_b 18.240(9) _cell_length_c 11.775(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.463(6) _cell_angle_gamma 90.00 _cell_volume 6958(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 877 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 26.50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3088 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details sadabs _exptl_special_details ; The large R2 value is due to a small crystal size and a poor diffracting power. ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13895 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.1689 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7657 _reflns_number_gt 2751 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.1744P] 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 7657 _refine_ls_number_parameters 503 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.2267 _refine_ls_R_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.2726 _refine_ls_wR_factor_gt 0.2070 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.052 _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 N1 N 0.17361(12) 0.3186(2) 1.0377(3) 0.0408(10) Uani 1 1 d . A 1 H1A H 0.1806 0.3398 0.9765 0.049 Uiso 1 1 calc R A 1 N2 N 0.24802(11) 0.3669(2) 0.9684(3) 0.0376(10) Uani 1 1 d . A 1 N3 N 0.20244(12) 0.4218(2) 0.7459(3) 0.0402(10) Uani 1 1 d . A 1 H3A H 0.1959 0.3966 0.8040 0.048 Uiso 1 1 calc R A 1 N4 N 0.12865(12) 0.3632(2) 0.8105(3) 0.0416(10) Uani 1 1 d . A 1 C1 C 0.13432(15) 0.2964(3) 1.0494(4) 0.0399(12) Uani 1 1 d . A 1 C2 C 0.13670(16) 0.2653(3) 1.1604(4) 0.0468(14) Uani 1 1 d . A 1 H2 H 0.1142 0.2451 1.1915 0.056 Uiso 1 1 calc R A 1 C3 C 0.17609(16) 0.2691(3) 1.2148(4) 0.0446(13) Uani 1 1 d . A 1 H3 H 0.1861 0.2527 1.2908 0.053 Uiso 1 1 calc R A 1 C4 C 0.20005(15) 0.3021(3) 1.1376(4) 0.0398(12) Uani 1 1 d . A 1 C5 C 0.24260(15) 0.3154(3) 1.1579(4) 0.0386(12) Uani 1 1 d . A 1 C6 C 0.26522(15) 0.3413(3) 1.0766(4) 0.0395(12) Uani 1 1 d . A 1 C7 C 0.30923(14) 0.3545(3) 1.0955(4) 0.0427(13) Uani 1 1 d . A 1 H7 H 0.3281 0.3425 1.1630 0.051 Uiso 1 1 calc R A 1 C8 C 0.31863(15) 0.3869(3) 1.0006(4) 0.0425(13) Uani 1 1 d . A 1 H8 H 0.3453 0.4006 0.9874 0.051 Uiso 1 1 calc R A 1 C9 C 0.28018(15) 0.3967(3) 0.9225(4) 0.0407(12) Uani 1 1 d . A 1 C10 C 0.27727(15) 0.4350(3) 0.8190(3) 0.0387(12) Uani 1 1 d . A 1 C11 C 0.24109(15) 0.4479(3) 0.7383(4) 0.0391(12) Uani 1 1 d . A 1 C12 C 0.23821(16) 0.4876(3) 0.6337(4) 0.0442(13) Uani 1 1 d . A 1 H12 H 0.2602 0.5126 0.6068 0.053 Uiso 1 1 calc R A 1 C13 C 0.19823(16) 0.4835(3) 0.5783(4) 0.0438(13) Uani 1 1 d . A 1 H13 H 0.1875 0.5050 0.5061 0.053 Uiso 1 1 calc R A 1 C14 C 0.17561(15) 0.4412(3) 0.6490(4) 0.0410(12) Uani 1 1 d . A 1 C15 C 0.13381(15) 0.4202(3) 0.6231(4) 0.0410(12) Uani 1 1 d . A 1 C16 C 0.11249(15) 0.3829(3) 0.6987(4) 0.0404(12) Uani 1 1 d . A 1 C17 C 0.07042(16) 0.3577(3) 0.6715(4) 0.0502(14) Uani 1 1 d . A 1 H17 H 0.0528 0.3628 0.5994 0.060 Uiso 1 1 calc R A 1 C18 C 0.06044(16) 0.3256(3) 0.7666(4) 0.0475(14) Uani 1 1 d . A 1 H18 H 0.0346 0.3048 0.7748 0.057 Uiso 1 1 calc R A 1 C19 C 0.09725(15) 0.3292(3) 0.8539(4) 0.0438(13) Uani 1 1 d . A 1 C20 C 0.09886(15) 0.3030(3) 0.9659(4) 0.0422(13) Uani 1 1 d . A 1 C21 C 0.26403(15) 0.3042(3) 1.2782(4) 0.0399(12) Uani 1 1 d . A 1 C22 C 0.29862(16) 0.2599(3) 1.3083(4) 0.0469(13) Uani 1 1 d . A 1 H22 H 0.3089 0.2322 1.2510 0.056 Uiso 1 1 calc R A 1 C23 C 0.31785(17) 0.2565(3) 1.4210(4) 0.0501(14) Uani 1 1 d . A 1 H23 H 0.3417 0.2265 1.4387 0.060 Uiso 1 1 calc R A 1 N5 N 0.30514(14) 0.2925(3) 1.5067(3) 0.0534(12) Uani 1 1 d . A 1 C24 C 0.27109(17) 0.3337(3) 1.4785(4) 0.0496(14) Uani 1 1 d . A 1 H24 H 0.2609 0.3587 1.5388 0.060 Uiso 1 1 calc R A 1 C25 C 0.24991(14) 0.3421(3) 1.3683(4) 0.0421(13) Uani 1 1 d . A 1 H25 H 0.2263 0.3729 1.3534 0.050 Uiso 1 1 calc R A 1 C26 C 0.31664(15) 0.4675(3) 0.7921(4) 0.0399(12) Uani 1 1 d . A 1 C27 C 0.33739(15) 0.4355(3) 0.7113(4) 0.0463(13) Uani 1 1 d . A 1 H27 H 0.3258 0.3946 0.6677 0.056 Uiso 1 1 calc R A 1 C28 C 0.37507(16) 0.4636(3) 0.6944(4) 0.0508(14) Uani 1 1 d . A 1 H28 H 0.3891 0.4422 0.6382 0.061 Uiso 1 1 calc R A 1 C29 C 0.39245(16) 0.5224(3) 0.7585(4) 0.0507(14) Uani 1 1 d . A 1 C30 C 0.4341(2) 0.5480(5) 0.7460(6) 0.083(2) Uani 1 1 d . A 1 F1 F 0.46340(12) 0.5157(4) 0.8207(4) 0.159(2) Uani 1 1 d . A 1 F2 F 0.43962(14) 0.6190(3) 0.7652(4) 0.128(2) Uani 1 1 d . A 1 F3 F 0.44350(11) 0.5370(2) 0.6419(3) 0.1012(14) Uani 1 1 d . A 1 C31 C 0.37211(16) 0.5552(3) 0.8379(4) 0.0532(14) Uani 1 1 d . A 1 H31 H 0.3840 0.5961 0.8813 0.064 Uiso 1 1 calc R A 1 C32 C 0.33374(15) 0.5278(3) 0.8542(4) 0.0467(13) Uani 1 1 d . A 1 H32 H 0.3193 0.5507 0.9082 0.056 Uiso 1 1 calc R A 1 C33 C 0.11111(15) 0.4387(3) 0.5060(3) 0.0390(12) Uani 1 1 d . A 1 C34 C 0.12527(17) 0.4145(3) 0.4064(4) 0.0493(14) Uani 1 1 d . A 1 H34 H 0.1503 0.3877 0.4123 0.059 Uiso 1 1 calc R A 1 C35 C 0.10277(18) 0.4298(3) 0.3004(4) 0.0524(15) Uani 1 1 d . A 1 H35 H 0.1130 0.4126 0.2342 0.063 Uiso 1 1 calc R A 1 N6 N 0.06731(15) 0.4674(3) 0.2846(3) 0.0577(13) Uani 1 1 d . A 1 C36 C 0.05392(17) 0.4914(3) 0.3797(4) 0.0531(15) Uani 1 1 d . A 1 H36 H 0.0289 0.5185 0.3708 0.064 Uiso 1 1 calc R A 1 C37 C 0.07484(16) 0.4788(3) 0.4909(4) 0.0479(14) Uani 1 1 d . A 1 H37 H 0.0643 0.4975 0.5556 0.058 Uiso 1 1 calc R A 1 C38 C 0.05979(15) 0.2769(3) 1.0002(4) 0.0409(12) Uani 1 1 d . A 1 C39 C 0.04639(18) 0.2053(4) 0.9820(5) 0.0670(18) Uani 1 1 d . A 1 H39 H 0.0628 0.1715 0.9480 0.080 Uiso 1 1 calc R A 1 C40 C 0.00927(19) 0.1819(4) 1.0127(5) 0.0735(19) Uani 1 1 d . A 1 H40 H -0.0003 0.1332 0.9962 0.088 Uiso 1 1 calc R A 1 C41 C -0.01314(16) 0.2297(4) 1.0665(4) 0.0523(15) Uani 1 1 d . A 1 F4 F -0.0849(3) 0.2230(8) 1.0227(10) 0.092(2) Uani 0.329(6) 1 d PD A 1 F5 F -0.0582(4) 0.2171(8) 1.2008(10) 0.092(2) Uani 0.329(6) 1 d PD A 1 F6 F -0.0564(3) 0.1254(6) 1.0761(10) 0.092(2) Uani 0.329(6) 1 d PD A 1 C42 C -0.0517(2) 0.2036(5) 1.1001(6) 0.092(2) Uani 1 1 d D . . C43 C -0.00037(16) 0.3002(3) 1.0897(4) 0.0517(15) Uani 1 1 d . . . H43 H -0.0162 0.3328 1.1279 0.062 Uiso 1 1 calc R A 1 C44 C 0.03636(15) 0.3235(3) 1.0561(4) 0.0488(14) Uani 1 1 d . A . H44 H 0.0455 0.3725 1.0719 0.059 Uiso 1 1 calc R B 1 F4A F -0.07694(19) 0.1653(4) 1.0239(5) 0.104(2) Uani 0.671(6) 1 d PD A 2 F5A F -0.07826(18) 0.2602(4) 1.1210(6) 0.104(2) Uani 0.671(6) 1 d PD A 2 F6A F -0.04783(18) 0.1673(4) 1.1981(5) 0.104(2) Uani 0.671(6) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.041(2) 0.052(3) 0.0305(19) 0.0059(19) 0.0069(18) -0.006(2) N2 0.042(2) 0.038(3) 0.0341(19) -0.0002(18) 0.0100(18) -0.0011(19) N3 0.042(3) 0.039(3) 0.038(2) 0.0023(19) 0.0047(19) -0.006(2) N4 0.041(2) 0.047(3) 0.037(2) 0.007(2) 0.0086(18) -0.002(2) C1 0.043(3) 0.045(3) 0.032(2) 0.004(2) 0.008(2) -0.003(2) C2 0.048(3) 0.056(4) 0.037(3) 0.004(2) 0.010(2) -0.007(3) C3 0.048(3) 0.048(4) 0.037(2) 0.003(2) 0.006(2) -0.003(3) C4 0.042(3) 0.043(3) 0.035(2) 0.000(2) 0.008(2) -0.006(2) C5 0.041(3) 0.040(3) 0.035(2) 0.003(2) 0.007(2) -0.001(2) C6 0.043(3) 0.043(3) 0.033(2) -0.002(2) 0.007(2) 0.000(2) C7 0.038(3) 0.048(4) 0.041(3) -0.001(2) 0.003(2) 0.002(3) C8 0.036(3) 0.052(4) 0.040(2) -0.003(2) 0.009(2) -0.003(2) C9 0.047(3) 0.041(3) 0.037(2) 0.000(2) 0.013(2) 0.002(2) C10 0.046(3) 0.041(3) 0.030(2) -0.004(2) 0.009(2) -0.002(2) C11 0.043(3) 0.037(3) 0.038(2) -0.002(2) 0.010(2) -0.002(2) C12 0.052(3) 0.044(3) 0.037(2) 0.003(2) 0.008(2) -0.002(3) C13 0.049(3) 0.046(4) 0.037(2) 0.008(2) 0.007(2) -0.002(3) C14 0.041(3) 0.045(3) 0.036(2) 0.000(2) 0.003(2) -0.004(3) C15 0.042(3) 0.041(3) 0.040(3) 0.000(2) 0.007(2) -0.002(2) C16 0.038(3) 0.049(4) 0.033(2) -0.005(2) 0.003(2) -0.003(2) C17 0.048(3) 0.063(4) 0.037(3) 0.003(3) 0.001(2) -0.005(3) C18 0.041(3) 0.058(4) 0.042(3) 0.005(3) 0.003(2) -0.007(3) C19 0.042(3) 0.046(4) 0.044(3) 0.004(2) 0.010(2) -0.003(3) C20 0.039(3) 0.052(4) 0.036(3) -0.002(2) 0.007(2) -0.001(3) C21 0.040(3) 0.041(3) 0.038(2) 0.003(2) 0.005(2) -0.002(2) C22 0.051(3) 0.042(4) 0.049(3) 0.001(3) 0.009(3) 0.008(3) C23 0.060(4) 0.046(4) 0.043(3) -0.001(3) 0.005(3) 0.000(3) N5 0.053(3) 0.060(3) 0.045(2) 0.009(2) 0.001(2) -0.002(3) C24 0.056(4) 0.054(4) 0.041(3) -0.006(3) 0.012(3) -0.004(3) C25 0.035(3) 0.051(4) 0.039(3) 0.001(2) 0.003(2) -0.002(2) C26 0.037(3) 0.047(4) 0.036(2) 0.000(2) 0.007(2) -0.002(2) C27 0.045(3) 0.051(4) 0.045(3) -0.004(3) 0.012(2) 0.001(3) C28 0.044(3) 0.062(4) 0.048(3) 0.003(3) 0.013(3) 0.005(3) C29 0.039(3) 0.058(4) 0.054(3) 0.013(3) 0.004(3) -0.006(3) C30 0.064(5) 0.099(7) 0.088(5) 0.030(5) 0.018(4) -0.015(5) F1 0.041(3) 0.243(7) 0.185(4) 0.104(5) -0.002(3) -0.015(3) F2 0.120(4) 0.146(5) 0.128(3) -0.019(3) 0.051(3) -0.087(4) F3 0.079(3) 0.121(4) 0.118(3) -0.003(3) 0.057(2) -0.029(2) C31 0.051(4) 0.050(4) 0.057(3) -0.001(3) 0.006(3) -0.005(3) C32 0.042(3) 0.046(4) 0.054(3) -0.001(3) 0.013(3) 0.000(3) C33 0.046(3) 0.040(3) 0.031(2) 0.007(2) 0.004(2) 0.000(3) C34 0.052(3) 0.053(4) 0.045(3) 0.006(3) 0.012(3) 0.004(3) C35 0.064(4) 0.055(4) 0.038(3) 0.002(3) 0.009(3) 0.005(3) N6 0.066(3) 0.061(4) 0.043(2) 0.005(2) -0.001(2) -0.001(3) C36 0.068(4) 0.052(4) 0.037(3) 0.002(3) 0.003(3) 0.008(3) C37 0.050(3) 0.050(4) 0.045(3) 0.001(3) 0.011(3) 0.004(3) C38 0.039(3) 0.042(4) 0.042(3) 0.004(2) 0.008(2) -0.003(3) C39 0.063(4) 0.056(4) 0.089(4) -0.029(3) 0.036(3) -0.018(3) C40 0.067(4) 0.067(5) 0.094(4) -0.024(4) 0.035(4) -0.023(4) C41 0.048(3) 0.067(5) 0.043(3) 0.003(3) 0.009(3) -0.019(3) F4 0.057(3) 0.133(6) 0.089(4) -0.016(4) 0.023(3) -0.035(4) F5 0.057(3) 0.133(6) 0.089(4) -0.016(4) 0.023(3) -0.035(4) F6 0.057(3) 0.133(6) 0.089(4) -0.016(4) 0.023(3) -0.035(4) C42 0.057(3) 0.133(6) 0.089(4) -0.016(4) 0.023(3) -0.035(4) C43 0.048(3) 0.062(4) 0.046(3) 0.010(3) 0.008(3) 0.001(3) C44 0.047(3) 0.048(4) 0.051(3) 0.011(3) 0.007(3) 0.001(3) F4A 0.065(3) 0.144(5) 0.110(3) 0.007(3) 0.035(2) -0.031(3) F5A 0.065(3) 0.144(5) 0.110(3) 0.007(3) 0.035(2) -0.031(3) F6A 0.065(3) 0.144(5) 0.110(3) 0.007(3) 0.035(2) -0.031(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.376(6) . ? N1 C1 1.380(6) . ? N1 H1A 0.8800 . ? N2 C9 1.374(5) . ? N2 C6 1.387(5) . ? N3 C14 1.368(5) . ? N3 C11 1.372(6) . ? N3 H3A 0.8800 . ? N4 C19 1.372(5) . ? N4 C16 1.383(5) . ? C1 C20 1.400(6) . ? C1 C2 1.416(6) . ? C2 C3 1.347(7) . ? C2 H2 0.9500 . ? C3 C4 1.429(6) . ? C3 H3 0.9500 . ? C4 C5 1.400(6) . ? C5 C6 1.388(6) . ? C5 C21 1.488(6) . ? C6 C7 1.446(6) . ? C7 C8 1.344(6) . ? C7 H7 0.9500 . ? C8 C9 1.446(6) . ? C8 H8 0.9500 . ? C9 C10 1.396(6) . ? C10 C11 1.413(6) . ? C10 C26 1.502(6) . ? C11 C12 1.419(6) . ? C12 C13 1.369(6) . ? C12 H12 0.9500 . ? C13 C14 1.430(6) . ? C13 H13 0.9500 . ? C14 C15 1.410(6) . ? C15 C16 1.396(6) . ? C15 C33 1.495(6) . ? C16 C17 1.442(6) . ? C17 C18 1.351(6) . ? C17 H17 0.9500 . ? C18 C19 1.454(6) . ? C18 H18 0.9500 . ? C19 C20 1.395(6) . ? C20 C38 1.486(6) . ? C21 C22 1.391(6) . ? C21 C25 1.408(6) . ? C22 C23 1.375(6) . ? C22 H22 0.9500 . ? C23 N5 1.327(6) . ? C23 H23 0.9500 . ? N5 C24 1.343(6) . ? C24 C25 1.376(6) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.387(6) . ? C26 C32 1.389(7) . ? C27 C28 1.384(7) . ? C27 H27 0.9500 . ? C28 C29 1.380(7) . ? C28 H28 0.9500 . ? C29 C31 1.373(7) . ? C29 C30 1.474(8) . ? C30 F2 1.322(8) . ? C30 F3 1.328(7) . ? C30 F1 1.331(8) . ? C31 C32 1.398(7) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C37 1.384(6) . ? C33 C34 1.402(6) . ? C34 C35 1.370(7) . ? C34 H34 0.9500 . ? C35 N6 1.338(6) . ? C35 H35 0.9500 . ? N6 C36 1.342(6) . ? C36 C37 1.394(6) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C39 1.383(7) . ? C38 C44 1.384(7) . ? C39 C40 1.394(7) . ? C39 H39 0.9500 . ? C40 C41 1.363(7) . ? C40 H40 0.9500 . ? C41 C43 1.367(7) . ? C41 C42 1.466(8) . ? F4 C42 1.350(11) . ? F5 C42 1.264(11) . ? F6 C42 1.456(11) . ? C42 F4A 1.317(8) . ? C42 F6A 1.318(8) . ? C42 F5A 1.400(9) . ? C43 C44 1.396(6) . ? C43 H43 0.9500 . ? C44 H44 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 C4 N1 C1 108.6(4) . . ? C4 N1 H1A 125.7 . . ? C1 N1 H1A 125.7 . . ? C9 N2 C6 105.7(4) . . ? C14 N3 C11 109.4(4) . . ? C14 N3 H3A 125.3 . . ? C11 N3 H3A 125.3 . . ? C19 N4 C16 106.1(4) . . ? N1 C1 C20 126.0(4) . . ? N1 C1 C2 107.4(4) . . ? C20 C1 C2 126.6(4) . . ? C3 C2 C1 108.7(4) . . ? C3 C2 H2 125.6 . . ? C1 C2 H2 125.6 . . ? C2 C3 C4 107.8(4) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N1 C4 C5 125.4(4) . . ? N1 C4 C3 107.4(4) . . ? C5 C4 C3 127.1(4) . . ? C6 C5 C4 125.0(4) . . ? C6 C5 C21 118.7(4) . . ? C4 C5 C21 116.2(4) . . ? N2 C6 C5 124.4(4) . . ? N2 C6 C7 109.3(4) . . ? C5 C6 C7 125.8(4) . . ? C8 C7 C6 107.8(4) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? C7 C8 C9 106.7(4) . . ? C7 C8 H8 126.7 . . ? C9 C8 H8 126.7 . . ? N2 C9 C10 126.5(4) . . ? N2 C9 C8 110.4(4) . . ? C10 C9 C8 123.0(4) . . ? C9 C10 C11 126.8(4) . . ? C9 C10 C26 116.4(4) . . ? C11 C10 C26 116.8(4) . . ? N3 C11 C10 125.7(4) . . ? N3 C11 C12 107.6(4) . . ? C10 C11 C12 126.7(4) . . ? C13 C12 C11 107.9(4) . . ? C13 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? C12 C13 C14 107.6(4) . . ? C12 C13 H13 126.2 . . ? C14 C13 H13 126.2 . . ? N3 C14 C15 125.5(4) . . ? N3 C14 C13 107.4(4) . . ? C15 C14 C13 127.0(4) . . ? C16 C15 C14 124.5(4) . . ? C16 C15 C33 118.2(4) . . ? C14 C15 C33 117.3(4) . . ? N4 C16 C15 125.4(4) . . ? N4 C16 C17 109.4(4) . . ? C15 C16 C17 125.2(4) . . ? C18 C17 C16 108.0(4) . . ? C18 C17 H17 126.0 . . ? C16 C17 H17 126.0 . . ? C17 C18 C19 106.2(4) . . ? C17 C18 H18 126.9 . . ? C19 C18 H18 126.9 . . ? N4 C19 C20 126.4(5) . . ? N4 C19 C18 110.2(4) . . ? C20 C19 C18 123.4(4) . . ? C19 C20 C1 126.2(4) . . ? C19 C20 C38 117.8(4) . . ? C1 C20 C38 115.9(4) . . ? C22 C21 C25 116.7(4) . . ? C22 C21 C5 124.1(4) . . ? C25 C21 C5 119.2(4) . . ? C23 C22 C21 120.0(5) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? N5 C23 C22 124.0(5) . . ? N5 C23 H23 118.0 . . ? C22 C23 H23 118.0 . . ? C23 N5 C24 116.3(4) . . ? N5 C24 C25 124.5(5) . . ? N5 C24 H24 117.7 . . ? C25 C24 H24 117.7 . . ? C24 C25 C21 118.5(5) . . ? C24 C25 H25 120.7 . . ? C21 C25 H25 120.7 . . ? C27 C26 C32 119.5(5) . . ? C27 C26 C10 121.1(5) . . ? C32 C26 C10 119.3(4) . . ? C28 C27 C26 119.7(5) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.6(5) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C31 C29 C28 120.5(5) . . ? C31 C29 C30 119.5(6) . . ? C28 C29 C30 119.9(6) . . ? F2 C30 F3 105.0(5) . . ? F2 C30 F1 104.8(7) . . ? F3 C30 F1 106.8(7) . . ? F2 C30 C29 113.4(7) . . ? F3 C30 C29 113.9(6) . . ? F1 C30 C29 112.1(6) . . ? C29 C31 C32 119.2(5) . . ? C29 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C26 C32 C31 120.4(5) . . ? C26 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C37 C33 C34 117.2(4) . . ? C37 C33 C15 121.7(4) . . ? C34 C33 C15 121.1(4) . . ? C35 C34 C33 119.6(5) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? N6 C35 C34 123.9(5) . . ? N6 C35 H35 118.1 . . ? C34 C35 H35 118.1 . . ? C35 N6 C36 116.6(4) . . ? N6 C36 C37 123.5(5) . . ? N6 C36 H36 118.3 . . ? C37 C36 H36 118.3 . . ? C33 C37 C36 119.2(4) . . ? C33 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? C39 C38 C44 117.8(5) . . ? C39 C38 C20 121.8(5) . . ? C44 C38 C20 120.3(5) . . ? C38 C39 C40 121.3(5) . . ? C38 C39 H39 119.4 . . ? C40 C39 H39 119.4 . . ? C41 C40 C39 119.1(6) . . ? C41 C40 H40 120.5 . . ? C39 C40 H40 120.5 . . ? C40 C41 C43 121.6(5) . . ? C40 C41 C42 118.3(6) . . ? C43 C41 C42 120.2(6) . . ? F5 C42 F4A 123.8(8) . . ? F4A C42 F6A 106.8(7) . . ? F5 C42 F4 109.8(9) . . ? F4A C42 F5A 99.8(6) . . ? F6A C42 F5A 100.9(6) . . ? F4 C42 F5A 57.7(6) . . ? F5 C42 F6 110.1(9) . . ? F4 C42 F6 94.5(8) . . ? F5 C42 C41 118.5(8) . . ? F4A C42 C41 117.7(6) . . ? F6A C42 C41 115.9(6) . . ? F4 C42 C41 111.8(7) . . ? F5A C42 C41 113.5(7) . . ? F6 C42 C41 109.6(7) . . ? C41 C43 C44 118.8(5) . . ? C41 C43 H43 120.6 . . ? C44 C43 H43 120.6 . . ? C38 C44 C43 121.4(5) . . ? C38 C44 H44 119.3 . . ? C43 C44 H44 119.3 . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.642 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.072