# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_as24a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N6 O2' _chemical_formula_weight 424.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 24.152(5) _cell_length_b 8.2300(16) _cell_length_c 23.368(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.92(3) _cell_angle_gamma 90.00 _cell_volume 4177.4(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5983 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19720 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4801 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1237P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4801 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1688 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.2280 _refine_ls_wR_factor_gt 0.1801 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 C1 C -0.20076(14) 0.4460(4) 0.04630(14) 0.0564(8) Uani 1 1 d . . . C2 C -0.25245(18) 0.5280(4) 0.00374(14) 0.0730(10) Uani 1 1 d . . . H2 H -0.2496 0.6028 -0.0247 0.088 Uiso 1 1 calc R . . C3 C -0.30812(17) 0.4963(5) 0.00439(19) 0.0844(12) Uani 1 1 d . . . H3 H -0.3431 0.5511 -0.0239 0.101 Uiso 1 1 calc R . . C4 C -0.31325(18) 0.3853(5) 0.0460(2) 0.0842(11) Uani 1 1 d . . . H4 H -0.3514 0.3658 0.0455 0.101 Uiso 1 1 calc R . . C5 C -0.26204(15) 0.3033(4) 0.08825(16) 0.0713(10) Uani 1 1 d . . . H5 H -0.2656 0.2285 0.1163 0.086 Uiso 1 1 calc R . . C6 C -0.20402(13) 0.3328(3) 0.08898(13) 0.0507(7) Uani 1 1 d . . . C7 C -0.15107(14) 0.2412(3) 0.13249(13) 0.0521(7) Uani 1 1 d . . . H7 H -0.1541 0.1797 0.1644 0.063 Uiso 1 1 calc R . . C8 C -0.00374(13) 0.1184(3) 0.15673(12) 0.0452(7) Uani 1 1 d . . . C9 C -0.00347(13) 0.1604(3) 0.09960(12) 0.0480(7) Uani 1 1 d . . . H9 H -0.0366 0.2126 0.0674 0.058 Uiso 1 1 calc R . . C10 C 0.04910(13) 0.1197(3) 0.09360(12) 0.0470(7) Uani 1 1 d . . . C11 C 0.09003(12) -0.0027(3) 0.19041(12) 0.0459(7) Uani 1 1 d . . . C12 C 0.14001(13) -0.1016(3) 0.23870(12) 0.0486(7) Uani 1 1 d . . . C13 C 0.13533(15) -0.1584(3) 0.29220(13) 0.0626(9) Uani 1 1 d . . . H13 H 0.1005 -0.1343 0.2979 0.075 Uiso 1 1 calc R . . C14 C 0.1818(2) -0.2502(4) 0.33703(15) 0.0794(11) Uani 1 1 d . . . H14 H 0.1783 -0.2863 0.3731 0.095 Uiso 1 1 calc R . . C15 C 0.23274(19) -0.2882(4) 0.32869(17) 0.0816(11) Uani 1 1 d . . . H15 H 0.2641 -0.3503 0.3589 0.098 Uiso 1 1 calc R . . C16 C 0.23753(16) -0.2339(4) 0.27498(18) 0.0757(10) Uani 1 1 d . . . H16 H 0.2720 -0.2610 0.2689 0.091 Uiso 1 1 calc R . . C17 C 0.19203(14) -0.1408(3) 0.23085(14) 0.0583(8) Uani 1 1 d . . . H17 H 0.1960 -0.1035 0.1953 0.070 Uiso 1 1 calc R . . C18 C 0.02349(14) 0.2869(4) -0.05496(13) 0.0562(8) Uani 1 1 d . . . H18 H 0.0603 0.2574 -0.0557 0.067 Uiso 1 1 calc R . . C19 C -0.02168(13) 0.3776(3) -0.10771(12) 0.0487(7) Uani 1 1 d . . . C20 C -0.01167(15) 0.4152(4) -0.16028(13) 0.0610(8) Uani 1 1 d . . . H20 H 0.0250 0.3829 -0.1608 0.073 Uiso 1 1 calc R . . C21 C -0.05408(16) 0.4985(4) -0.21138(14) 0.0659(9) Uani 1 1 d . . . H21 H -0.0463 0.5220 -0.2461 0.079 Uiso 1 1 calc R . . C22 C -0.10767(16) 0.5463(4) -0.21079(14) 0.0697(9) Uani 1 1 d . . . H22 H -0.1367 0.6021 -0.2456 0.084 Uiso 1 1 calc R . . C23 C -0.11987(15) 0.5138(4) -0.15976(14) 0.0702(9) Uani 1 1 d . . . H23 H -0.1565 0.5486 -0.1597 0.084 Uiso 1 1 calc R . . C24 C -0.07703(14) 0.4285(4) -0.10831(13) 0.0574(8) Uani 1 1 d . . . N1 N -0.10025(11) 0.2434(3) 0.12779(10) 0.0520(6) Uani 1 1 d . . . N2 N -0.05228(11) 0.1533(3) 0.17010(10) 0.0557(7) Uani 1 1 d . . . H2A H -0.0526 0.1190 0.2047 0.067 Uiso 1 1 calc R . . N3 N 0.04284(10) 0.0381(3) 0.20296(9) 0.0468(6) Uani 1 1 d . . . N4 N 0.09614(10) 0.0363(3) 0.13802(10) 0.0498(6) Uani 1 1 d . . . N5 N 0.05779(12) 0.1605(3) 0.04119(10) 0.0627(7) Uani 1 1 d . . . H5A H 0.0910 0.1320 0.0389 0.075 Uiso 1 1 calc R . . N6 N 0.01374(11) 0.2465(3) -0.00726(10) 0.0542(6) Uani 1 1 d . . . O1 O -0.14747(12) 0.4833(3) 0.04500(11) 0.0884(8) Uani 1 1 d . . . H1 H -0.1194 0.4323 0.0728 0.133 Uiso 1 1 calc R . . O2 O -0.09135(11) 0.4003(3) -0.05948(11) 0.0880(8) Uani 1 1 d . . . H2B H -0.0647 0.3429 -0.0329 0.132 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 C1 0.0512(19) 0.0590(19) 0.0589(18) -0.0141(16) 0.0241(16) -0.0028(16) C2 0.082(3) 0.064(2) 0.0578(19) -0.0064(16) 0.0167(19) 0.018(2) C3 0.054(2) 0.087(3) 0.086(3) -0.035(2) 0.006(2) 0.018(2) C4 0.063(3) 0.083(3) 0.107(3) -0.032(2) 0.037(2) -0.002(2) C5 0.049(2) 0.073(2) 0.088(2) -0.0300(19) 0.0270(19) 0.0028(17) C6 0.0505(19) 0.0499(17) 0.0520(16) -0.0112(14) 0.0226(15) 0.0040(14) C7 0.059(2) 0.0548(18) 0.0486(16) -0.0049(13) 0.0295(15) 0.0001(15) C8 0.0511(18) 0.0449(15) 0.0415(15) -0.0015(12) 0.0220(14) -0.0016(13) C9 0.0518(18) 0.0543(16) 0.0371(15) 0.0068(12) 0.0185(14) 0.0074(14) C10 0.0565(19) 0.0479(16) 0.0401(15) 0.0011(12) 0.0244(15) 0.0024(14) C11 0.0522(17) 0.0432(15) 0.0418(15) 0.0004(12) 0.0202(14) 0.0002(13) C12 0.0559(19) 0.0411(15) 0.0414(15) 0.0014(12) 0.0145(14) 0.0017(14) C13 0.078(2) 0.0547(18) 0.0499(17) 0.0087(14) 0.0230(17) 0.0088(16) C14 0.111(3) 0.059(2) 0.054(2) 0.0124(16) 0.023(2) 0.013(2) C15 0.084(3) 0.057(2) 0.068(2) 0.0136(17) 0.001(2) 0.009(2) C16 0.054(2) 0.063(2) 0.091(3) 0.0038(19) 0.0147(19) 0.0031(18) C17 0.053(2) 0.0523(18) 0.0612(18) 0.0059(14) 0.0172(16) 0.0045(15) C18 0.064(2) 0.0647(19) 0.0491(17) 0.0077(14) 0.0328(16) 0.0070(16) C19 0.0548(19) 0.0509(16) 0.0420(15) 0.0028(13) 0.0228(14) -0.0041(14) C20 0.072(2) 0.070(2) 0.0473(17) 0.0047(15) 0.0314(17) -0.0010(17) C21 0.082(2) 0.072(2) 0.0468(17) 0.0115(15) 0.0313(18) -0.0029(19) C22 0.077(3) 0.064(2) 0.0539(19) 0.0130(16) 0.0158(19) -0.0025(18) C23 0.064(2) 0.073(2) 0.070(2) 0.0154(17) 0.0267(19) 0.0098(18) C24 0.065(2) 0.0612(19) 0.0510(17) 0.0117(14) 0.0299(17) 0.0025(16) N1 0.0501(15) 0.0603(15) 0.0453(13) 0.0007(11) 0.0205(12) 0.0050(12) N2 0.0528(16) 0.0771(17) 0.0410(13) 0.0091(12) 0.0240(12) 0.0116(13) N3 0.0521(15) 0.0508(13) 0.0384(12) 0.0048(10) 0.0206(12) 0.0044(11) N4 0.0555(15) 0.0530(14) 0.0431(13) 0.0087(11) 0.0234(12) 0.0108(12) N5 0.0670(17) 0.0803(18) 0.0496(14) 0.0218(13) 0.0336(13) 0.0223(14) N6 0.0605(16) 0.0617(15) 0.0427(13) 0.0108(11) 0.0247(12) 0.0082(13) O1 0.0891(19) 0.0941(19) 0.0864(18) 0.0133(13) 0.0425(16) 0.0022(15) O2 0.0817(18) 0.123(2) 0.0811(16) 0.0361(15) 0.0555(15) 0.0266(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 C1 O1 1.337(4) . ? C1 C2 1.385(4) . ? C1 C6 1.392(4) . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C4 C5 1.376(5) . ? C4 H4 0.9300 . ? C5 C6 1.415(4) . ? C5 H5 0.9300 . ? C6 C7 1.450(4) . ? C7 N1 1.279(4) . ? C7 H7 0.9300 . ? C8 N3 1.344(3) . ? C8 N2 1.369(3) . ? C8 C9 1.382(3) . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 N4 1.345(3) . ? C10 N5 1.372(3) . ? C11 N4 1.335(3) . ? C11 N3 1.338(3) . ? C11 C12 1.484(4) . ? C12 C13 1.385(4) . ? C12 C17 1.385(4) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.365(5) . ? C14 H14 0.9300 . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.366(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N6 1.280(3) . ? C18 C19 1.446(4) . ? C18 H18 0.9300 . ? C19 C20 1.387(3) . ? C19 C24 1.395(4) . ? C20 C21 1.369(4) . ? C20 H20 0.9300 . ? C21 C22 1.359(4) . ? C21 H21 0.9300 . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 C24 1.386(4) . ? C23 H23 0.9300 . ? C24 O2 1.349(3) . ? N1 N2 1.367(3) . ? N2 H2A 0.8600 . ? N5 N6 1.364(3) . ? N5 H5A 0.8600 . ? O1 H1 0.8200 . ? O2 H2B 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 116.5(3) . . ? O1 C1 C6 121.8(3) . . ? C2 C1 C6 121.7(3) . . ? C3 C2 C1 118.6(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.5(4) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 120.1(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 118.2(3) . . ? C1 C6 C7 122.8(3) . . ? C5 C6 C7 119.0(3) . . ? N1 C7 C6 121.2(3) . . ? N1 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? N3 C8 N2 114.8(2) . . ? N3 C8 C9 122.9(2) . . ? N2 C8 C9 122.3(3) . . ? C10 C9 C8 115.5(3) . . ? C10 C9 H9 122.2 . . ? C8 C9 H9 122.2 . . ? N4 C10 N5 114.0(2) . . ? N4 C10 C9 123.4(2) . . ? N5 C10 C9 122.6(3) . . ? N4 C11 N3 125.9(2) . . ? N4 C11 C12 116.8(2) . . ? N3 C11 C12 117.3(2) . . ? C13 C12 C17 118.5(3) . . ? C13 C12 C11 120.7(3) . . ? C17 C12 C11 120.7(2) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.6(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 120.5(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 120.5(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? N6 C18 C19 121.3(3) . . ? N6 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C24 117.5(3) . . ? C20 C19 C18 120.8(3) . . ? C24 C19 C18 121.8(2) . . ? C21 C20 C19 122.1(3) . . ? C21 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 121.3(3) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 119.3(3) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? O2 C24 C23 116.8(3) . . ? O2 C24 C19 122.6(3) . . ? C23 C24 C19 120.6(3) . . ? C7 N1 N2 118.2(2) . . ? N1 N2 C8 119.3(2) . . ? N1 N2 H2A 120.4 . . ? C8 N2 H2A 120.4 . . ? C11 N3 C8 116.2(2) . . ? C11 N4 C10 115.8(2) . . ? N6 N5 C10 120.0(2) . . ? N6 N5 H5A 120.0 . . ? C10 N5 H5A 120.0 . . ? C18 N6 N5 118.9(2) . . ? C1 O1 H1 109.5 . . ? C24 O2 H2B 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 0.785 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 951969' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_as29 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H27 N7 O2' _chemical_formula_weight 493.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6423(4) _cell_length_b 29.0929(17) _cell_length_c 11.6687(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.778(3) _cell_angle_gamma 90.00 _cell_volume 2591.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8683 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10031 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.1157 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5887 _reflns_number_gt 2302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0791P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5887 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1971 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.1798 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1737(3) 0.55095(10) 0.0992(2) 0.0550(7) Uani 1 1 d . . . C1S C 1.1173(7) 0.24449(19) 0.3171(6) 0.1345(18) Uani 1 1 d . . . C2 C 0.1044(4) 0.59460(10) 0.1045(2) 0.0685(8) Uani 1 1 d . . . H2 H 0.0917 0.6086 0.1753 0.082 Uiso 1 1 calc R . . C2S C 1.0673(6) 0.26460(17) 0.2098(4) 0.1473(18) Uani 1 1 d . . . H2S1 H 0.9636 0.2827 0.2174 0.221 Uiso 1 1 calc R . . H2S2 H 1.0443 0.2408 0.1541 0.221 Uiso 1 1 calc R . . H2S3 H 1.1603 0.2839 0.1853 0.221 Uiso 1 1 calc R . . C3 C 0.0538(4) 0.61747(10) 0.0046(3) 0.0739(9) Uani 1 1 d . . . H3 H 0.0096 0.6472 0.0081 0.089 Uiso 1 1 calc R . . C4 C 0.0685(4) 0.59650(11) -0.0999(3) 0.0727(9) Uani 1 1 d . . . H4 H 0.0326 0.6118 -0.1670 0.087 Uiso 1 1 calc R . . C5 C 0.1361(3) 0.55303(10) -0.1050(2) 0.0582(7) Uani 1 1 d . . . H5 H 0.1439 0.5390 -0.1762 0.070 Uiso 1 1 calc R . . C6 C 0.1936(3) 0.52928(9) -0.00652(18) 0.0457(6) Uani 1 1 d . . . C7 C 0.2670(3) 0.48371(9) -0.01689(18) 0.0481(7) Uani 1 1 d . . . H7 H 0.2688 0.4698 -0.0885 0.058 Uiso 1 1 calc R . . C8 C 0.3954(4) 0.39461(9) -0.04463(17) 0.0600(8) Uani 1 1 d . . . H8A H 0.2787 0.3928 -0.0787 0.090 Uiso 1 1 calc R . . H8B H 0.4406 0.3641 -0.0322 0.090 Uiso 1 1 calc R . . H8C H 0.4690 0.4110 -0.0950 0.090 Uiso 1 1 calc R . . C9 C 0.4673(3) 0.40018(9) 0.16464(18) 0.0452(6) Uani 1 1 d . . . C10 C 0.5184(3) 0.42730(9) 0.25822(17) 0.0465(6) Uani 1 1 d . . . H10 H 0.5003 0.4589 0.2584 0.056 Uiso 1 1 calc R . . C11 C 0.5980(3) 0.40466(9) 0.35144(18) 0.0458(6) Uani 1 1 d . . . C12 C 0.5608(3) 0.33617(9) 0.26052(18) 0.0471(6) Uani 1 1 d . . . C13 C 0.5810(3) 0.28554(9) 0.2616(2) 0.0504(7) Uani 1 1 d . . . C14 C 0.5316(4) 0.25952(9) 0.1657(2) 0.0602(7) Uani 1 1 d . . . H14 H 0.4867 0.2742 0.0998 0.072 Uiso 1 1 calc R . . C15 C 0.5477(4) 0.21259(10) 0.1665(2) 0.0702(8) Uani 1 1 d . . . H15 H 0.5149 0.1957 0.1012 0.084 Uiso 1 1 calc R . . C16 C 0.6122(4) 0.19041(10) 0.2634(2) 0.0741(9) Uani 1 1 d . . . H16 H 0.6223 0.1586 0.2641 0.089 Uiso 1 1 calc R . . C17 C 0.6617(4) 0.21539(10) 0.3592(2) 0.0725(9) Uani 1 1 d . . . H17 H 0.7054 0.2004 0.4249 0.087 Uiso 1 1 calc R . . C18 C 0.6468(4) 0.26274(10) 0.3584(2) 0.0618(8) Uani 1 1 d . . . H18 H 0.6814 0.2794 0.4236 0.074 Uiso 1 1 calc R . . C19 C 0.7190(4) 0.40575(9) 0.55360(18) 0.0617(8) Uani 1 1 d . . . H19A H 0.8415 0.4111 0.5706 0.093 Uiso 1 1 calc R . . H19B H 0.6980 0.3733 0.5464 0.093 Uiso 1 1 calc R . . H19C H 0.6525 0.4179 0.6145 0.093 Uiso 1 1 calc R . . C20 C 0.7565(3) 0.49926(9) 0.51510(19) 0.0507(7) Uani 1 1 d . . . H20 H 0.7875 0.4857 0.5853 0.061 Uiso 1 1 calc R . . C21 C 0.7849(3) 0.54828(9) 0.49912(18) 0.0469(6) Uani 1 1 d . . . C22 C 0.8543(4) 0.57444(10) 0.5906(2) 0.0631(8) Uani 1 1 d . . . H22 H 0.8839 0.5601 0.6600 0.076 Uiso 1 1 calc R . . C23 C 0.8797(4) 0.62071(11) 0.5804(2) 0.0782(9) Uani 1 1 d . . . H23 H 0.9258 0.6376 0.6425 0.094 Uiso 1 1 calc R . . C24 C 0.8368(4) 0.64226(10) 0.4778(3) 0.0796(9) Uani 1 1 d . . . H24 H 0.8524 0.6738 0.4710 0.096 Uiso 1 1 calc R . . C25 C 0.7709(4) 0.61722(10) 0.3851(2) 0.0720(9) Uani 1 1 d . . . H25 H 0.7441 0.6319 0.3156 0.086 Uiso 1 1 calc R . . C26 C 0.7446(3) 0.57064(9) 0.3951(2) 0.0557(7) Uani 1 1 d . . . N1 N 0.3298(3) 0.46235(7) 0.07274(15) 0.0471(5) Uani 1 1 d . . . N1S N 1.1548(7) 0.2309(2) 0.4053(5) 0.193(2) Uani 1 1 d . . . N2 N 0.3922(3) 0.41869(7) 0.06467(14) 0.0506(6) Uani 1 1 d . . . N3 N 0.4898(3) 0.35467(7) 0.16421(15) 0.0502(6) Uani 1 1 d . . . N4 N 0.6167(3) 0.35901(7) 0.35508(15) 0.0487(5) Uani 1 1 d . . . N5 N 0.6660(3) 0.42843(7) 0.44668(14) 0.0506(6) Uani 1 1 d . . . N6 N 0.6887(3) 0.47451(7) 0.43261(14) 0.0492(6) Uani 1 1 d . . . O1 O 0.2227(3) 0.52948(7) 0.19976(13) 0.0793(7) Uani 1 1 d . . . H1 H 0.2659 0.5044 0.1859 0.119 Uiso 1 1 calc R . . O2 O 0.6772(3) 0.54751(6) 0.30210(13) 0.0807(7) Uani 1 1 d . . . H2A H 0.6672 0.5202 0.3182 0.121 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 C1 0.0572(18) 0.0555(19) 0.0513(16) -0.0016(13) -0.0070(12) 0.0026(15) C1S 0.097(4) 0.146(5) 0.162(5) 0.029(4) 0.025(3) -0.002(3) C2 0.073(2) 0.056(2) 0.0752(19) -0.0136(15) -0.0068(15) 0.0051(17) C2S 0.131(4) 0.185(5) 0.127(4) -0.005(4) 0.022(3) 0.017(4) C3 0.068(2) 0.049(2) 0.103(2) 0.0097(18) -0.0065(18) 0.0022(16) C4 0.081(2) 0.063(2) 0.073(2) 0.0183(17) -0.0040(16) 0.0014(18) C5 0.0641(19) 0.0573(19) 0.0529(16) 0.0109(13) 0.0005(13) -0.0041(16) C6 0.0416(16) 0.0480(17) 0.0471(14) 0.0013(12) -0.0008(11) -0.0070(13) C7 0.0482(17) 0.0569(19) 0.0389(13) -0.0009(12) -0.0001(11) -0.0035(14) C8 0.073(2) 0.063(2) 0.0438(14) -0.0099(13) -0.0035(12) 0.0057(16) C9 0.0441(16) 0.0491(17) 0.0419(14) 0.0015(12) -0.0014(11) 0.0031(13) C10 0.0508(16) 0.0431(16) 0.0452(14) -0.0025(11) -0.0018(11) 0.0032(13) C11 0.0457(16) 0.0506(18) 0.0411(14) -0.0009(12) 0.0032(11) 0.0001(14) C12 0.0466(16) 0.0461(17) 0.0489(15) -0.0008(13) 0.0047(12) 0.0019(13) C13 0.0542(17) 0.0476(17) 0.0501(15) -0.0010(13) 0.0087(12) -0.0008(14) C14 0.078(2) 0.0478(18) 0.0550(16) 0.0001(13) 0.0061(13) -0.0010(16) C15 0.100(2) 0.048(2) 0.0636(18) -0.0059(15) 0.0082(16) -0.0039(18) C16 0.103(3) 0.0452(19) 0.075(2) 0.0001(16) 0.0210(18) 0.0050(18) C17 0.100(3) 0.052(2) 0.0657(19) 0.0104(15) 0.0072(16) 0.0156(18) C18 0.079(2) 0.0515(19) 0.0553(16) 0.0001(13) 0.0016(14) 0.0049(16) C19 0.084(2) 0.0552(18) 0.0449(15) 0.0064(13) -0.0039(13) -0.0035(16) C20 0.0567(17) 0.057(2) 0.0379(14) -0.0019(12) -0.0032(11) 0.0028(14) C21 0.0508(17) 0.0473(17) 0.0424(14) -0.0035(12) 0.0001(11) 0.0002(13) C22 0.079(2) 0.061(2) 0.0478(15) -0.0037(14) -0.0073(13) -0.0049(17) C23 0.105(3) 0.062(2) 0.0665(19) -0.0152(16) -0.0090(16) -0.010(2) C24 0.107(3) 0.048(2) 0.083(2) -0.0035(17) -0.0078(18) -0.0005(18) C25 0.098(2) 0.051(2) 0.0655(18) 0.0100(15) -0.0066(16) 0.0064(18) C26 0.071(2) 0.0476(18) 0.0473(16) -0.0018(13) -0.0062(13) 0.0042(15) N1 0.0510(14) 0.0467(14) 0.0431(11) 0.0002(10) -0.0030(9) 0.0009(11) N1S 0.145(4) 0.223(6) 0.213(5) 0.070(5) 0.015(4) -0.014(4) N2 0.0623(15) 0.0481(14) 0.0407(12) -0.0052(10) -0.0060(9) 0.0081(12) N3 0.0559(14) 0.0481(15) 0.0459(12) 0.0008(10) -0.0033(10) 0.0023(11) N4 0.0577(14) 0.0413(14) 0.0468(12) -0.0005(10) -0.0017(9) -0.0001(11) N5 0.0665(15) 0.0432(14) 0.0411(12) 0.0021(9) -0.0071(10) -0.0030(11) N6 0.0613(15) 0.0425(14) 0.0433(12) -0.0018(10) -0.0011(9) 0.0023(11) O1 0.1129(18) 0.0760(16) 0.0472(10) -0.0090(9) -0.0146(10) 0.0275(13) O2 0.1284(18) 0.0622(14) 0.0489(11) 0.0013(9) -0.0243(11) -0.0041(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.365(3) . ? C1 C2 1.379(4) . ? C1 C6 1.400(3) . ? C1S N1S 1.127(5) . ? C1S C2S 1.418(6) . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.369(4) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 H5 0.9300 . ? C6 C7 1.447(3) . ? C7 N1 1.289(3) . ? C7 H7 0.9300 . ? C8 N2 1.456(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N3 1.335(3) . ? C9 N2 1.384(3) . ? C9 C10 1.388(3) . ? C10 C11 1.387(3) . ? C10 H10 0.9300 . ? C11 N4 1.336(3) . ? C11 N5 1.388(3) . ? C12 N3 1.337(3) . ? C12 N4 1.340(3) . ? C12 C13 1.481(3) . ? C13 C18 1.384(3) . ? C13 C14 1.388(3) . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 C16 1.373(4) . ? C15 H15 0.9300 . ? C16 C17 1.370(4) . ? C16 H16 0.9300 . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N5 1.452(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N6 1.290(3) . ? C20 C21 1.456(3) . ? C20 H20 0.9300 . ? C21 C22 1.394(3) . ? C21 C26 1.398(3) . ? C22 C23 1.366(4) . ? C22 H22 0.9300 . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 C25 1.380(4) . ? C24 H24 0.9300 . ? C25 C26 1.376(4) . ? C25 H25 0.9300 . ? C26 O2 1.357(3) . ? N1 N2 1.362(2) . ? N5 N6 1.363(3) . ? O1 H1 0.8200 . ? O2 H2A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 118.2(2) . . ? O1 C1 C6 121.0(2) . . ? C2 C1 C6 120.8(2) . . ? N1S C1S C2S 176.0(7) . . ? C1 C2 C3 119.9(3) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.8(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 117.4(2) . . ? C5 C6 C7 119.6(2) . . ? C1 C6 C7 123.0(2) . . ? N1 C7 C6 120.3(2) . . ? N1 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 N2 115.5(2) . . ? N3 C9 C10 122.4(2) . . ? N2 C9 C10 122.1(2) . . ? C11 C10 C9 116.3(2) . . ? C11 C10 H10 121.8 . . ? C9 C10 H10 121.8 . . ? N4 C11 C10 122.6(2) . . ? N4 C11 N5 115.7(2) . . ? C10 C11 N5 121.6(2) . . ? N3 C12 N4 126.3(2) . . ? N3 C12 C13 116.4(2) . . ? N4 C12 C13 117.2(2) . . ? C18 C13 C14 118.1(3) . . ? C18 C13 C12 121.2(2) . . ? C14 C13 C12 120.8(2) . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.6(3) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? N5 C19 H19A 109.5 . . ? N5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N6 C20 C21 120.5(2) . . ? N6 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C26 118.0(3) . . ? C22 C21 C20 119.4(2) . . ? C26 C21 C20 122.6(2) . . ? C23 C22 C21 121.5(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? O2 C26 C25 118.2(2) . . ? O2 C26 C21 121.5(2) . . ? C25 C26 C21 120.3(2) . . ? C7 N1 N2 120.75(19) . . ? N1 N2 C9 115.91(18) . . ? N1 N2 C8 122.02(18) . . ? C9 N2 C8 121.8(2) . . ? C9 N3 C12 116.3(2) . . ? C11 N4 C12 115.9(2) . . ? N6 N5 C11 116.01(18) . . ? N6 N5 C19 121.27(19) . . ? C11 N5 C19 122.7(2) . . ? C20 N6 N5 120.53(19) . . ? C1 O1 H1 109.5 . . ? C26 O2 H2A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.207 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 951970' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C100 H80 B4 F16 Fe4 N26 O9' _chemical_formula_weight 2360.48 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 Tetragonal _symmetry_space_group_name_H-M P-421c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 20.064(3) _cell_length_b 20.064(3) _cell_length_c 13.088(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5268.9(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4735 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 24.48 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2388 _exptl_absorpt_coefficient_mu 0.638 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8452 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 24.48 _reflns_number_total 4375 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. geometrical restraints were used for the refinement of the solvent molecule ; _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^)+(0.1295P)^2^+6.8448P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 4375 _refine_ls_number_parameters 348 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.2278 _refine_ls_wR_factor_gt 0.2141 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1887(4) 0.7047(4) 1.0312(6) 0.044(2) Uani 1 1 d . . . C2 C 0.1966(5) 0.6416(4) 0.9910(7) 0.062(2) Uani 1 1 d . . . H2 H 0.1936 0.6354 0.9191 0.075 Uiso 1 1 calc R . . C3 C 0.2087(6) 0.5881(5) 1.0518(7) 0.067(3) Uani 1 1 d . . . H3 H 0.2149 0.5455 1.0216 0.081 Uiso 1 1 calc R . . C4 C 0.2120(5) 0.5946(5) 1.1575(7) 0.062(3) Uani 1 1 d . . . H4 H 0.2190 0.5565 1.1994 0.075 Uiso 1 1 calc R . . C5 C 0.2052(4) 0.6550(4) 1.1995(6) 0.052(2) Uani 1 1 d . . . H5 H 0.2089 0.6592 1.2715 0.062 Uiso 1 1 calc R . . C6 C 0.1927(4) 0.7135(4) 1.1401(5) 0.047(2) Uani 1 1 d . . . C7 C 0.1852(4) 0.7755(4) 1.1898(6) 0.0416(19) Uani 1 1 d . . . H7 H 0.1876 0.7758 1.2623 0.050 Uiso 1 1 calc R . . C8 C 0.1615(4) 0.9455(4) 1.1651(5) 0.0420(19) Uani 1 1 d . . . C9 C 0.0031(5) 0.8451(4) 0.7768(6) 0.049(2) Uani 1 1 d . . . H9 H 0.0011 0.8441 0.7043 0.058 Uiso 1 1 calc R . . C10 C 0.0618(4) 0.8530(4) 0.8251(5) 0.0418(19) Uani 1 1 d . . . C11 C 0.1571(4) 1.0106(4) 1.0197(6) 0.0406(19) Uani 1 1 d . . . C12 C 0.1654(4) 1.0135(3) 0.9055(4) 0.067(3) Uani 1 1 d G . . C13 C 0.1107(4) 1.0129(4) 0.8402(6) 0.109(5) Uani 1 1 d G . . H13 H 0.0669 1.0100 0.8674 0.130 Uiso 1 1 calc R . . C14 C 0.1202(7) 1.0166(4) 0.7352(5) 0.190(13) Uani 1 1 d G . . H14 H 0.0828 1.0162 0.6906 0.229 Uiso 1 1 calc R . . C15 C 0.1843(8) 1.0208(4) 0.6954(4) 0.211(15) Uani 1 1 d G . . H15 H 0.1907 1.0234 0.6236 0.253 Uiso 1 1 calc R . . C16 C 0.2389(6) 1.0214(4) 0.7607(7) 0.209(14) Uani 1 1 d G . . H16 H 0.2827 1.0243 0.7335 0.251 Uiso 1 1 calc R . . C17 C 0.2295(4) 1.0177(4) 0.8657(6) 0.117(6) Uani 1 1 d G . . H17 H 0.2668 1.0181 0.9103 0.140 Uiso 1 1 calc R . . C18 C 0.2322(4) 0.8542(4) 0.7680(6) 0.045(2) Uani 1 1 d . . . H18 H 0.2259 0.8516 0.6962 0.055 Uiso 1 1 calc R . . C19 C 0.2981(4) 0.8525(4) 0.8044(6) 0.049(2) Uani 1 1 d . . . C20 C 0.3508(5) 0.8441(5) 0.7340(6) 0.063(2) Uani 1 1 d . . . H20 H 0.3404 0.8360 0.6643 0.076 Uiso 1 1 calc R . . C21 C 0.4134(6) 0.8470(6) 0.7616(8) 0.078(3) Uani 1 1 d . . . H21 H 0.4477 0.8397 0.7127 0.094 Uiso 1 1 calc R . . C22 C 0.4297(6) 0.8609(8) 0.8633(10) 0.096(4) Uani 1 1 d . . . H22 H 0.4750 0.8647 0.8833 0.115 Uiso 1 1 calc R . . C23 C 0.3786(5) 0.8691(6) 0.9355(7) 0.082(3) Uani 1 1 d . . . H23 H 0.3899 0.8787 1.0045 0.098 Uiso 1 1 calc R . . C24 C 0.3138(4) 0.8636(4) 0.9090(6) 0.046(2) Uani 1 1 d . . . N1 N 0.1754(3) 0.8316(3) 1.1445(4) 0.0430(16) Uani 1 1 d . . . N2 N 0.1714(4) 0.8869(3) 1.2049(5) 0.0464(18) Uani 1 1 d . . . H2A H 0.1756 0.8829 1.2716 0.056 Uiso 1 1 calc R . . N3 N 0.1609(3) 0.9497(3) 1.0589(4) 0.0390(16) Uani 1 1 d . . . N4 N 0.0676(3) 0.8503(3) 0.9311(4) 0.0393(15) Uani 1 1 d . . . N5 N 0.1191(3) 0.8588(4) 0.7743(5) 0.0476(18) Uani 1 1 d . . . H5A H 0.1185 0.8627 0.7073 0.057 Uiso 1 1 calc R . . N6 N 0.1790(3) 0.8590(3) 0.8249(4) 0.0405(15) Uani 1 1 d . . . O1 O 0.1774(3) 0.7559(3) 0.9709(4) 0.0550(15) Uani 1 1 d . . . O2 O 0.2676(3) 0.8714(3) 0.9802(4) 0.0577(16) Uani 1 1 d . . . C33 C 0.5000 1.0000 1.142(3) 0.58(4) Uani 1 2 d SDU . . Fe1 Fe 0.17542(6) 0.85098(5) 0.98487(8) 0.0424(4) Uani 1 1 d . . . B1 B 0.1689(7) 0.8934(6) 1.4912(7) 0.073(4) Uani 1 1 d . . . F1 F 0.1689(4) 0.8529(3) 1.4103(4) 0.111(3) Uani 1 1 d . . . F2 F 0.1553(7) 0.9547(4) 1.4535(5) 0.167(5) Uani 1 1 d . . . F3 F 0.2280(4) 0.8980(7) 1.5374(5) 0.166(5) Uani 1 1 d . . . F4 F 0.1205(3) 0.8762(4) 1.5624(4) 0.097(2) Uani 1 1 d . . . N12 N 0.5000 1.0000 1.229(3) 0.57(4) Uani 1 2 d SDU . . C34 C 0.5000 1.0000 1.027(3) 0.56(4) Uani 1 2 d SDU . . O1W O 0.0000 1.0000 0.5000 0.161(9) Uani 1 4 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(5) 0.050(5) 0.044(4) 0.011(4) -0.003(4) -0.001(4) C2 0.094(7) 0.051(6) 0.041(5) -0.001(5) 0.003(5) 0.004(5) C3 0.105(8) 0.048(6) 0.050(5) 0.004(5) 0.006(5) 0.001(5) C4 0.084(7) 0.061(6) 0.042(5) 0.014(5) -0.001(5) 0.014(5) C5 0.056(5) 0.069(6) 0.032(4) 0.008(4) -0.003(4) 0.000(5) C6 0.057(5) 0.061(6) 0.023(4) 0.011(4) -0.007(4) -0.006(4) C7 0.042(5) 0.050(5) 0.033(4) 0.010(4) 0.003(4) 0.004(4) C8 0.052(5) 0.050(5) 0.024(3) 0.000(4) 0.001(4) -0.001(4) C9 0.070(6) 0.054(6) 0.022(4) 0.000(4) 0.001(4) 0.001(5) C10 0.051(5) 0.051(5) 0.023(4) 0.008(4) 0.002(4) 0.002(4) C11 0.037(4) 0.062(5) 0.023(3) -0.009(4) 0.004(3) -0.010(4) C12 0.147(11) 0.028(4) 0.026(4) -0.001(3) 0.006(6) -0.004(5) C13 0.230(17) 0.057(7) 0.039(5) 0.004(5) -0.050(8) -0.014(8) C14 0.49(4) 0.050(8) 0.031(7) 0.001(6) -0.038(13) 0.043(15) C15 0.54(5) 0.050(8) 0.040(8) 0.005(6) 0.056(16) 0.025(16) C16 0.47(4) 0.057(9) 0.097(12) 0.024(8) 0.169(18) 0.051(15) C17 0.231(18) 0.049(7) 0.071(7) 0.001(5) 0.094(9) -0.003(8) C18 0.062(6) 0.045(5) 0.029(4) -0.006(4) 0.003(4) -0.004(4) C19 0.058(5) 0.056(5) 0.034(4) 0.006(4) 0.006(4) -0.007(4) C20 0.063(6) 0.087(7) 0.041(4) -0.001(5) 0.011(5) 0.000(5) C21 0.061(7) 0.112(10) 0.061(6) 0.001(6) 0.016(5) 0.010(7) C22 0.063(7) 0.136(12) 0.088(9) 0.006(8) -0.016(6) -0.003(7) C23 0.068(7) 0.136(11) 0.040(5) 0.011(6) 0.018(5) 0.016(7) C24 0.035(5) 0.069(6) 0.034(4) 0.002(4) 0.004(4) 0.008(4) N1 0.056(4) 0.053(4) 0.020(3) -0.003(3) 0.001(3) -0.003(4) N2 0.072(5) 0.049(4) 0.018(3) 0.001(3) -0.011(3) 0.000(4) N3 0.049(4) 0.045(4) 0.022(3) -0.002(3) 0.000(3) -0.001(3) N4 0.051(4) 0.051(4) 0.016(3) 0.001(3) -0.003(3) 0.003(3) N5 0.051(4) 0.072(5) 0.020(3) 0.005(3) -0.001(3) 0.002(4) N6 0.047(4) 0.049(4) 0.025(3) 0.004(3) 0.001(3) -0.005(4) O1 0.085(4) 0.055(3) 0.025(3) 0.003(2) 0.003(3) 0.000(3) O2 0.077(4) 0.077(4) 0.019(2) 0.003(3) 0.000(3) 0.000(3) C33 0.74(6) 0.80(7) 0.20(3) 0.000 0.000 -0.65(6) Fe1 0.0550(7) 0.0554(7) 0.0166(5) 0.0021(5) -0.0016(5) 0.0024(5) B1 0.102(9) 0.100(9) 0.016(4) 0.001(5) -0.001(6) 0.028(7) F1 0.209(8) 0.100(5) 0.023(2) -0.001(3) 0.008(4) -0.013(5) F2 0.345(15) 0.109(6) 0.048(4) 0.023(4) 0.024(6) 0.028(7) F3 0.110(6) 0.346(15) 0.042(4) 0.014(6) -0.015(4) -0.012(7) F4 0.114(5) 0.152(6) 0.024(3) 0.014(3) -0.005(3) -0.021(4) N12 0.73(6) 0.82(7) 0.18(3) 0.000 0.000 -0.63(6) C34 0.75(6) 0.77(7) 0.18(3) 0.000 0.000 -0.67(6) O1W 0.187(13) 0.187(13) 0.110(19) 0.000 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.315(9) . ? C1 C2 1.381(11) . ? C1 C6 1.439(11) . ? C2 C3 1.357(13) . ? C2 H2 0.9500 . ? C3 C4 1.391(13) . ? C3 H3 0.9500 . ? C4 C5 1.338(12) . ? C4 H4 0.9500 . ? C5 C6 1.429(11) . ? C5 H5 0.9500 . ? C6 C7 1.411(11) . ? C7 N1 1.288(9) . ? C7 H7 0.9500 . ? C8 N2 1.302(10) . ? C8 C9 1.389(11) 4_667 ? C8 N3 1.393(9) . ? C9 C10 1.347(12) . ? C9 C8 1.389(12) 3_467 ? C9 H9 0.9500 . ? C10 N5 1.333(10) . ? C10 N4 1.394(9) . ? C11 N4 1.322(10) 4_667 ? C11 N3 1.327(10) . ? C11 C12 1.504(8) . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N6 1.305(10) . ? C18 C19 1.406(12) . ? C18 H18 0.9500 . ? C19 C20 1.413(13) . ? C19 C24 1.423(11) . ? C20 C21 1.309(14) . ? C20 H20 0.9500 . ? C21 C22 1.398(16) . ? C21 H21 0.9500 . ? C22 C23 1.403(15) . ? C22 H22 0.9500 . ? C23 C24 1.351(13) . ? C23 H23 0.9500 . ? C24 O2 1.323(9) . ? N1 N2 1.366(9) . ? N1 Fe1 2.125(6) . ? N2 H2A 0.8800 . ? N3 Fe1 2.224(6) . ? N4 C11 1.322(10) 3_467 ? N4 Fe1 2.274(6) . ? N5 N6 1.372(9) . ? N5 H5A 0.8800 . ? N6 Fe1 2.101(6) . ? O1 Fe1 1.917(6) . ? O2 Fe1 1.896(6) . ? C33 N12 1.140(8) . ? C33 C34 1.513(8) . ? B1 F3 1.334(14) . ? B1 F1 1.335(12) . ? B1 F2 1.354(14) . ? B1 F4 1.390(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.5(8) . . ? O1 C1 C6 120.6(8) . . ? C2 C1 C6 118.9(8) . . ? C3 C2 C1 121.4(9) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.3(9) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.1(9) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 122.6(8) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C7 C6 C5 119.5(7) . . ? C7 C6 C1 123.9(7) . . ? C5 C6 C1 116.6(8) . . ? N1 C7 C6 125.1(7) . . ? N1 C7 H7 117.5 . . ? C6 C7 H7 117.5 . . ? N2 C8 C9 123.2(7) . 4_667 ? N2 C8 N3 117.0(7) . . ? C9 C8 N3 119.7(7) 4_667 . ? C10 C9 C8 118.8(7) . 3_467 ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 3_467 . ? N5 C10 C9 122.1(7) . . ? N5 C10 N4 115.3(7) . . ? C9 C10 N4 122.4(7) . . ? N4 C11 N3 127.9(6) 4_667 . ? N4 C11 C12 117.6(7) 4_667 . ? N3 C11 C12 114.4(6) . . ? C13 C12 C17 120.0 . . ? C13 C12 C11 121.6(5) . . ? C17 C12 C11 118.4(5) . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.0 . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? N6 C18 C19 125.3(7) . . ? N6 C18 H18 117.4 . . ? C19 C18 H18 117.4 . . ? C18 C19 C20 119.1(8) . . ? C18 C19 C24 122.1(7) . . ? C20 C19 C24 118.7(8) . . ? C21 C20 C19 122.3(9) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 119.7(10) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C23 119.7(10) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 121.3(9) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? O2 C24 C23 119.0(8) . . ? O2 C24 C19 122.7(7) . . ? C23 C24 C19 118.3(8) . . ? C7 N1 N2 116.9(6) . . ? C7 N1 Fe1 127.8(5) . . ? N2 N1 Fe1 114.9(5) . . ? C8 N2 N1 120.8(6) . . ? C8 N2 H2A 119.6 . . ? N1 N2 H2A 119.6 . . ? C11 N3 C8 116.2(6) . . ? C11 N3 Fe1 131.2(5) . . ? C8 N3 Fe1 112.4(5) . . ? C11 N4 C10 114.7(6) 3_467 . ? C11 N4 Fe1 132.4(5) 3_467 . ? C10 N4 Fe1 112.8(5) . . ? C10 N5 N6 121.0(6) . . ? C10 N5 H5A 119.5 . . ? N6 N5 H5A 119.5 . . ? C18 N6 N5 116.2(6) . . ? C18 N6 Fe1 126.2(5) . . ? N5 N6 Fe1 116.8(4) . . ? C1 O1 Fe1 136.4(5) . . ? C24 O2 Fe1 132.9(5) . . ? N12 C33 C34 180.00(4) . . ? O2 Fe1 O1 101.1(3) . . ? O2 Fe1 N6 85.3(2) . . ? O1 Fe1 N6 88.9(2) . . ? O2 Fe1 N1 94.1(3) . . ? O1 Fe1 N1 84.9(2) . . ? N6 Fe1 N1 173.5(3) . . ? O2 Fe1 N3 87.1(2) . . ? O1 Fe1 N3 158.5(2) . . ? N6 Fe1 N3 111.7(2) . . ? N1 Fe1 N3 74.6(2) . . ? O2 Fe1 N4 156.8(2) . . ? O1 Fe1 N4 89.1(3) . . ? N6 Fe1 N4 74.0(2) . . ? N1 Fe1 N4 107.6(2) . . ? N3 Fe1 N4 90.9(2) . . ? F3 B1 F1 113.8(11) . . ? F3 B1 F2 106.3(12) . . ? F1 B1 F2 105.3(8) . . ? F3 B1 F4 109.6(8) . . ? F1 B1 F4 112.3(11) . . ? F2 B1 F4 109.2(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.089 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 951971' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_as12a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C118 H103 F24 N31 O33 S8 Zn4' _chemical_formula_weight 3457.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 Orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 29.541(6) _cell_length_b 18.148(4) _cell_length_c 27.020(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 14486(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8540 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6932 _exptl_absorpt_coefficient_mu 0.884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8795 _exptl_absorpt_correction_T_max 0.9572 _exptl_absorpt_process_details ? _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 'kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32162 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0700 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 27.47 _reflns_number_total 16927 _reflns_number_gt 9798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. geometrical restraints were used for the refinement of the disordered anions and solvent molecules ; _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^)+(0.1590P)^2^+2.5705P] 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 16927 _refine_ls_number_parameters 1079 _refine_ls_number_restraints 97 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2606 _refine_ls_wR_factor_gt 0.2242 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.14253(16) 0.8245(3) 0.20686(19) 0.0304(11) Uani 1 1 d . . . C2 C 0.15122(18) 0.8987(3) 0.2183(2) 0.0388(13) Uani 1 1 d . . . H2 H 0.1514 0.9149 0.2517 0.047 Uiso 1 1 calc R . . C3 C 0.15951(18) 0.9482(3) 0.1799(2) 0.0428(14) Uani 1 1 d . . . H3 H 0.1643 0.9987 0.1874 0.051 Uiso 1 1 calc R . . C4 C 0.16088(19) 0.9256(3) 0.1313(2) 0.0435(14) Uani 1 1 d . . . H4 H 0.1668 0.9599 0.1055 0.052 Uiso 1 1 calc R . . C5 C 0.15349(18) 0.8521(3) 0.1208(2) 0.0394(13) Uani 1 1 d . . . H5 H 0.1546 0.8361 0.0873 0.047 Uiso 1 1 calc R . . C6 C 0.14449(16) 0.8006(3) 0.1578(2) 0.0323(11) Uani 1 1 d . . . C7 C 0.13755(16) 0.7251(3) 0.14188(19) 0.0322(11) Uani 1 1 d . . . H7 H 0.1390 0.7161 0.1073 0.039 Uiso 1 1 calc R . . C8 C 0.11484(15) 0.5410(3) 0.16880(17) 0.0254(10) Uani 1 1 d . . . C9 C 0.10652(15) 0.4765(3) 0.14308(17) 0.0279(10) Uani 1 1 d . . . H9 H 0.1052 0.4757 0.1080 0.033 Uiso 1 1 calc R . . C10 C 0.10014(15) 0.4131(3) 0.17093(17) 0.0253(10) Uani 1 1 d . . . C11 C 0.10783(14) 0.4803(3) 0.24309(16) 0.0234(10) Uani 1 1 d . . . C12 C 0.10877(17) 0.4829(3) 0.29796(18) 0.0316(11) Uani 1 1 d . . . C13 C 0.1505(2) 0.4793(3) 0.3222(2) 0.0412(13) Uani 1 1 d . . . H13 H 0.1778 0.4755 0.3038 0.049 Uiso 1 1 calc R . . C14 C 0.1517(3) 0.4814(3) 0.3733(2) 0.0552(18) Uani 1 1 d . . . H14 H 0.1800 0.4789 0.3898 0.066 Uiso 1 1 calc R . . C15 C 0.1134(3) 0.4870(3) 0.4004(2) 0.072(2) Uani 1 1 d . . . H15 H 0.1150 0.4881 0.4355 0.086 Uiso 1 1 calc R . . C16 C 0.0706(3) 0.4912(3) 0.3761(3) 0.071(2) Uani 1 1 d . . . H16 H 0.0436 0.4960 0.3948 0.085 Uiso 1 1 calc R . . C17 C 0.0688(2) 0.4882(3) 0.3251(2) 0.0434(14) Uani 1 1 d . . . H17 H 0.0404 0.4898 0.3086 0.052 Uiso 1 1 calc R . . C18 C 0.08151(16) 0.2255(3) 0.15259(19) 0.0316(11) Uani 1 1 d . . . H18 H 0.0832 0.2288 0.1176 0.038 Uiso 1 1 calc R . . C19 C 0.07308(16) 0.1532(3) 0.1737(2) 0.0333(12) Uani 1 1 d . . . C20 C 0.06474(19) 0.0955(3) 0.1390(2) 0.0447(14) Uani 1 1 d . . . H20 H 0.0653 0.1063 0.1046 0.054 Uiso 1 1 calc R . . C21 C 0.0560(2) 0.0254(3) 0.1541(3) 0.0530(16) Uani 1 1 d . . . H21 H 0.0502 -0.0124 0.1306 0.064 Uiso 1 1 calc R . . C22 C 0.05558(19) 0.0100(3) 0.2047(3) 0.0531(17) Uani 1 1 d . . . H22 H 0.0498 -0.0389 0.2156 0.064 Uiso 1 1 calc R . . C23 C 0.06344(19) 0.0647(3) 0.2394(2) 0.0453(14) Uani 1 1 d . . . H23 H 0.0629 0.0534 0.2737 0.054 Uiso 1 1 calc R . . C24 C 0.07217(16) 0.1364(3) 0.2237(2) 0.0331(11) Uani 1 1 d . . . C25 C 0.23280(16) 0.6245(3) 0.27641(18) 0.0305(11) Uani 1 1 d . . . C26 C 0.27533(17) 0.6005(3) 0.2618(2) 0.0393(13) Uani 1 1 d . . . H26 H 0.2824 0.5982 0.2275 0.047 Uiso 1 1 calc R . . C27 C 0.30768(19) 0.5799(3) 0.2963(2) 0.0465(14) Uani 1 1 d . . . H27 H 0.3367 0.5641 0.2856 0.056 Uiso 1 1 calc R . . C28 C 0.29760(18) 0.5824(4) 0.3466(2) 0.0491(15) Uani 1 1 d . . . H28 H 0.3196 0.5678 0.3703 0.059 Uiso 1 1 calc R . . C29 C 0.25579(18) 0.6061(3) 0.3615(2) 0.0458(14) Uani 1 1 d . . . H29 H 0.2493 0.6084 0.3959 0.055 Uiso 1 1 calc R . . C30 C 0.22178(16) 0.6275(3) 0.32704(18) 0.0307(11) Uani 1 1 d . . . C31 C 0.17839(16) 0.6475(3) 0.34724(18) 0.0300(11) Uani 1 1 d . . . H31 H 0.1769 0.6546 0.3820 0.036 Uiso 1 1 calc R . . C32 C 0.06232(15) 0.6729(3) 0.32936(17) 0.0246(10) Uani 1 1 d . . . C33 C -0.02365(16) 0.3198(3) 0.35749(18) 0.0299(11) Uani 1 1 d . . . H33 H -0.0247 0.3172 0.3926 0.036 Uiso 1 1 calc R . . C34 C 0.01697(15) 0.3163(2) 0.33154(17) 0.0244(10) Uani 1 1 d . . . C35 C -0.02089(15) 0.3235(2) 0.25721(17) 0.0242(10) Uani 1 1 d . . . C36 C -0.02078(16) 0.3174(3) 0.20241(19) 0.0385(13) Uani 1 1 d . . . C37 C -0.02830(17) 0.2470(4) 0.1822(2) 0.0481(15) Uani 1 1 d . . . H37 H -0.0328 0.2060 0.2035 0.058 Uiso 1 1 calc R . . C38 C -0.0291(2) 0.2373(5) 0.1305(3) 0.066(2) Uani 1 1 d . . . H38 H -0.0335 0.1900 0.1163 0.079 Uiso 1 1 calc R . . C39 C -0.0235(2) 0.2962(6) 0.1025(3) 0.071(2) Uani 1 1 d . . . H39 H -0.0249 0.2896 0.0677 0.085 Uiso 1 1 calc R . . C40 C -0.0158(2) 0.3672(6) 0.1199(3) 0.076(3) Uani 1 1 d . . . H40 H -0.0115 0.4076 0.0981 0.091 Uiso 1 1 calc R . . C41 C -0.01478(19) 0.3760(4) 0.1723(2) 0.0536(16) Uani 1 1 d . . . H41 H -0.0099 0.4235 0.1862 0.064 Uiso 1 1 calc R . . C42 C 0.13260(16) 0.3038(3) 0.35781(19) 0.0301(11) Uani 1 1 d . . . H42 H 0.1281 0.2992 0.3925 0.036 Uiso 1 1 calc R . . C43 C 0.17873(16) 0.3062(3) 0.3407(2) 0.0322(11) Uani 1 1 d . . . C44 C 0.21208(18) 0.3179(3) 0.3773(2) 0.0418(13) Uani 1 1 d . . . H44 H 0.2033 0.3201 0.4111 0.050 Uiso 1 1 calc R . . C45 C 0.25648(19) 0.3261(4) 0.3651(2) 0.0487(15) Uani 1 1 d . . . H45 H 0.2786 0.3333 0.3902 0.058 Uiso 1 1 calc R . . C46 C 0.26901(18) 0.3238(3) 0.3160(3) 0.0491(15) Uani 1 1 d . . . H46 H 0.2999 0.3312 0.3074 0.059 Uiso 1 1 calc R . . C47 C 0.23761(17) 0.3111(3) 0.2789(2) 0.0373(12) Uani 1 1 d . . . H47 H 0.2469 0.3084 0.2453 0.045 Uiso 1 1 calc R . . C48 C 0.19285(16) 0.3024(3) 0.29132(19) 0.0303(11) Uani 1 1 d . . . N1 N 0.12967(12) 0.6692(2) 0.16977(14) 0.0246(8) Uani 1 1 d . . . N2 N 0.12435(13) 0.6034(2) 0.14392(14) 0.0266(9) Uani 1 1 d . . . H2A H 0.1272 0.6026 0.1115 0.032 Uiso 1 1 calc R . . N3 N 0.11516(12) 0.5441(2) 0.21936(14) 0.0240(8) Uani 1 1 d . . . N4 N 0.09909(12) 0.4154(2) 0.22144(14) 0.0248(8) Uani 1 1 d . . . N5 N 0.09495(14) 0.3472(2) 0.14908(14) 0.0294(9) Uani 1 1 d . . . H5A H 0.0966 0.3433 0.1167 0.035 Uiso 1 1 calc R . . N6 N 0.08700(12) 0.2859(2) 0.17760(14) 0.0256(8) Uani 1 1 d . . . N7 N 0.14151(13) 0.6567(2) 0.32276(14) 0.0251(8) Uani 1 1 d . . . N8 N 0.10353(13) 0.6675(2) 0.35127(14) 0.0279(9) Uani 1 1 d . . . H8 H 0.1059 0.6710 0.3836 0.034 Uiso 1 1 calc R . . N9 N 0.06096(12) 0.6704(2) 0.27895(14) 0.0238(8) Uani 1 1 d . . . N10 N 0.01905(12) 0.3195(2) 0.28094(14) 0.0251(8) Uani 1 1 d . . . N11 N 0.05643(12) 0.3086(2) 0.35577(15) 0.0279(9) Uani 1 1 d . . . H11 H 0.0565 0.3044 0.3882 0.033 Uiso 1 1 calc R . . N12 N 0.09652(13) 0.3073(2) 0.33049(15) 0.0264(9) Uani 1 1 d . . . O1 O 0.13230(12) 0.77527(19) 0.24379(12) 0.0317(8) Uani 1 1 d . . . H1 H 0.1265 0.7982 0.2747 0.038 Uiso 1 1 calc R . . O2 O 0.08029(13) 0.19040(19) 0.25726(14) 0.0394(9) Uani 1 1 d . . . H2B H 0.0839 0.1719 0.2899 0.047 Uiso 1 1 calc R . . O3 O 0.20127(11) 0.64561(19) 0.24292(12) 0.0314(8) Uani 1 1 d . . . H3A H 0.2136 0.6597 0.2119 0.038 Uiso 1 1 calc R . . O4 O 0.16092(11) 0.2900(2) 0.25519(12) 0.0351(8) Uani 1 1 d . . . H4A H 0.1727 0.2690 0.2257 0.042 Uiso 1 1 calc R . . Zn1 Zn 0.126485(17) 0.65378(3) 0.246492(19) 0.02468(17) Uani 1 1 d . . . Zn2 Zn 0.087011(18) 0.31020(3) 0.253357(19) 0.02627(17) Uani 1 1 d . . . C51 C 0.1798(4) 0.7290(6) 0.5000 0.062(3) Uani 1 2 d S . . O11 O 0.11582(16) 0.6640(3) 0.45532(15) 0.0694(14) Uani 1 1 d . . . O12 O 0.1688(3) 0.5888(4) 0.5000 0.105(3) Uani 1 2 d S . . F11 F 0.20741(16) 0.7257(3) 0.46010(16) 0.0986(17) Uani 1 1 d . . . F12 F 0.1606(3) 0.7919(4) 0.5000 0.118(3) Uani 1 2 d S . . S1 S 0.14090(8) 0.65225(12) 0.5000 0.0446(5) Uani 1 2 d S . . C52 C 0.1946(2) 0.1624(4) 0.0944(2) 0.0519(16) Uani 1 1 d . . . O21 O 0.24649(19) 0.2754(3) 0.1093(2) 0.0900(18) Uani 1 1 d . . . O22 O 0.19471(16) 0.2339(4) 0.17446(19) 0.0885(19) Uani 1 1 d . . . O23 O 0.26150(14) 0.1649(3) 0.15437(15) 0.0596(12) Uani 1 1 d . . . F21 F 0.16202(13) 0.2047(3) 0.07550(18) 0.0879(14) Uani 1 1 d . . . F22 F 0.21935(14) 0.1393(3) 0.05736(17) 0.0906(15) Uani 1 1 d . . . F23 F 0.17518(16) 0.1079(3) 0.1169(2) 0.0992(16) Uani 1 1 d . . . S2 S 0.22798(5) 0.21619(9) 0.13771(6) 0.0471(4) Uani 1 1 d . . . C53 C 0.1777(4) 0.6405(8) 0.0000 0.083(4) Uani 1 2 d S . . O31 O 0.1035(3) 0.7077(5) 0.0000 0.096(3) Uani 1 2 d S . . O32 O 0.10725(16) 0.5953(3) 0.04435(14) 0.0697(14) Uani 1 1 d . . . F31 F 0.19254(16) 0.6759(4) 0.0402(2) 0.137(3) Uani 1 1 d . . . F32 F 0.1974(3) 0.5758(5) 0.0000 0.128(3) Uani 1 2 d S . . S3 S 0.11787(7) 0.63286(14) 0.0000 0.0503(6) Uani 1 2 d S . . C54 C 0.0164(4) 0.3752(6) 0.5000 0.064(3) Uani 1 2 d S . . O41 O 0.0584(2) 0.2716(3) 0.45618(15) 0.0789(16) Uani 1 1 d . . . O42 O 0.1029(3) 0.3568(5) 0.5000 0.132(4) Uani 1 2 d S . . F41 F -0.0214(3) 0.3330(6) 0.5000 0.146(4) Uani 1 2 d S . . F42 F 0.0114(2) 0.4114(3) 0.45941(18) 0.1130(19) Uani 1 1 d . . . S4 S 0.06362(9) 0.31206(13) 0.5000 0.0535(6) Uani 1 2 d S . . C55 C 0.0459(3) 0.4171(8) 0.0000 0.080(4) Uani 1 2 d S . . O51 O 0.0922(2) 0.3297(3) 0.04475(17) 0.095(2) Uani 1 1 d . . . O52 O 0.1341(3) 0.4177(6) 0.0000 0.133(4) Uani 1 2 d S . . F51 F 0.0083(3) 0.3863(4) 0.0000 0.092(2) Uani 1 2 d S . . F52 F 0.04503(16) 0.4697(3) 0.04026(17) 0.0914(14) Uani 1 1 d . . . S5 S 0.09211(11) 0.3601(2) 0.0000 0.0830(10) Uani 1 2 d S . . C56 C 0.03983(15) 0.8874(3) 0.3487(3) 0.071(4) Uiso 0.50 1 d PD A 1 O63 O 0.1087(3) 0.9030(5) 0.40543(19) 0.091(4) Uani 0.50 1 d PD A 1 F61 F 0.0195(2) 0.9515(4) 0.3567(4) 0.143(5) Uani 0.50 1 d PDU A 1 F62 F 0.0283(2) 0.8648(5) 0.3040(3) 0.100(3) Uani 0.50 1 d PD A 1 F63 F 0.0240(2) 0.8396(4) 0.3809(3) 0.095(3) Uani 0.50 1 d PD A 1 O61 O 0.1089(3) 0.9637(3) 0.3249(4) 0.111(7) Uani 0.50 1 d PD A 1 O62 O 0.11679(18) 0.8299(3) 0.3301(2) 0.0249(14) Uani 0.50 1 d PD A 1 S6 S 0.10133(11) 0.89657(18) 0.35294(13) 0.0475(9) Uani 0.50 1 d PD A 1 F61A F 0.1026(4) 0.9049(4) 0.4337(2) 0.102(4) Uani 0.50 1 d PD B 2 F62A F 0.0657(3) 0.8072(4) 0.4163(3) 0.079(2) Uiso 0.50 1 d PDU B 2 F63A F 0.1349(3) 0.8175(6) 0.3951(4) 0.179(6) Uiso 0.50 1 d PDU B 2 C56A C 0.0962(2) 0.8544(4) 0.3995(2) 0.132(8) Uiso 0.50 1 d PDU B 2 O61A O 0.1137(3) 0.9490(5) 0.3317(4) 0.103(5) Uani 0.50 1 d PDU B 2 O62A O 0.0806(4) 0.8313(4) 0.3078(3) 0.129(5) Uani 0.50 1 d PDU B 2 O63A O 0.0349(3) 0.9232(7) 0.3509(4) 0.173(6) Uani 0.50 1 d PDU B 2 S6A S 0.07905(15) 0.8936(3) 0.34034(15) 0.0689(14) Uani 0.50 1 d PDU B 2 C1S C 0.2163(2) 0.4598(4) 0.1643(3) 0.0566(17) Uani 1 1 d . . . C2S C 0.2224(2) 0.4619(5) 0.1107(3) 0.084(3) Uani 1 1 d . . . N1S N 0.2113(2) 0.4589(4) 0.2062(3) 0.0727(17) Uani 1 1 d . . . C3S C 0.0792(3) 0.1138(4) 0.3872(3) 0.070(2) Uani 1 1 d . . . C4S C 0.0731(4) 0.0785(5) 0.4361(4) 0.119(4) Uani 1 1 d . . . N2S N 0.0824(2) 0.1400(3) 0.3495(2) 0.0720(19) Uani 1 1 d . . . C5S C 0.0365(11) 0.9004(12) 0.5000 0.55(3) Uani 1 2 d SDU . . C6S C 0.0535(13) 0.8212(12) 0.5000 0.55(3) Uani 1 2 d SDU . . N3S N 0.0183(10) 0.9558(11) 0.5000 0.54(3) Uani 1 2 d SDU . . C7S C 0.2768(8) 0.3875(10) 0.0000 0.117(7) Uani 1 2 d SD . . C8S C 0.2338(9) 0.3413(12) 0.0000 0.205(13) Uani 1 2 d SD . . N4S N 0.3053(7) 0.4299(15) 0.0000 0.200(11) Uani 1 2 d SD . . N5S N 0.3095(5) 0.6345(10) 0.5000 0.224(8) Uani 1 2 d SDU . . C10S C 0.3031(8) 0.4892(10) 0.5000 0.200(8) Uani 1 2 d SDU . . C9S C 0.3163(5) 0.5711(10) 0.5000 0.176(7) Uani 1 2 d SDU . . O1W O 0.0373(14) 0.207(3) 0.0000 0.53(5) Uani 0.60 2 d SP . . O2W O 0.0946(11) 0.190(3) 0.0000 0.23(2) Uani 0.40 2 d SP . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(3) 0.035(3) 0.026(3) 0.002(2) 0.001(2) 0.002(2) C2 0.044(3) 0.041(3) 0.032(3) -0.001(2) -0.002(2) 0.003(2) C3 0.047(3) 0.035(3) 0.047(4) 0.000(3) 0.005(3) -0.011(2) C4 0.046(3) 0.040(3) 0.044(4) 0.011(3) 0.011(3) -0.005(3) C5 0.047(3) 0.045(3) 0.026(3) 0.004(2) 0.010(2) -0.001(2) C6 0.031(3) 0.034(3) 0.032(3) 0.004(2) 0.002(2) 0.002(2) C7 0.036(3) 0.043(3) 0.018(3) 0.001(2) 0.004(2) 0.001(2) C8 0.025(2) 0.035(3) 0.016(2) 0.000(2) -0.0003(19) 0.0015(19) C9 0.030(3) 0.042(3) 0.012(2) 0.001(2) 0.0011(19) -0.004(2) C10 0.022(2) 0.039(3) 0.015(2) -0.002(2) -0.0014(18) -0.0003(19) C11 0.021(2) 0.035(3) 0.014(2) 0.0032(19) 0.0001(18) -0.0008(19) C12 0.046(3) 0.034(3) 0.015(2) 0.000(2) 0.004(2) -0.003(2) C13 0.057(3) 0.041(3) 0.026(3) 0.000(2) -0.014(3) -0.007(3) C14 0.098(5) 0.041(3) 0.027(3) 0.002(3) -0.025(4) -0.012(3) C15 0.153(8) 0.043(4) 0.019(3) 0.001(3) -0.010(4) -0.008(4) C16 0.127(7) 0.049(4) 0.036(4) 0.005(3) 0.046(4) 0.005(4) C17 0.058(3) 0.042(3) 0.030(3) -0.002(2) 0.018(3) -0.001(3) C18 0.028(3) 0.039(3) 0.027(3) -0.003(2) 0.002(2) 0.000(2) C19 0.026(2) 0.037(3) 0.037(3) -0.007(2) -0.001(2) -0.001(2) C20 0.044(3) 0.046(3) 0.045(4) -0.009(3) -0.004(3) -0.006(3) C21 0.053(4) 0.040(3) 0.066(5) -0.013(3) 0.000(3) -0.014(3) C22 0.047(3) 0.035(3) 0.077(5) -0.001(3) -0.003(3) -0.008(3) C23 0.045(3) 0.044(3) 0.047(4) 0.002(3) -0.002(3) 0.001(3) C24 0.025(2) 0.040(3) 0.034(3) -0.004(2) 0.002(2) -0.001(2) C25 0.028(2) 0.041(3) 0.023(3) -0.003(2) -0.002(2) 0.002(2) C26 0.034(3) 0.051(3) 0.032(3) -0.002(2) 0.011(2) 0.005(2) C27 0.032(3) 0.062(4) 0.046(4) 0.001(3) -0.001(3) 0.009(3) C28 0.030(3) 0.080(4) 0.038(3) 0.002(3) -0.007(3) 0.007(3) C29 0.035(3) 0.073(4) 0.030(3) 0.000(3) -0.005(2) 0.011(3) C30 0.027(2) 0.043(3) 0.022(3) 0.001(2) -0.004(2) -0.003(2) C31 0.034(3) 0.039(3) 0.017(2) 0.004(2) -0.006(2) -0.003(2) C32 0.027(2) 0.034(2) 0.013(2) 0.0015(18) -0.0025(18) -0.0033(19) C33 0.033(3) 0.041(3) 0.016(2) 0.000(2) -0.001(2) -0.001(2) C34 0.026(2) 0.030(2) 0.017(2) 0.0035(19) -0.0016(19) 0.0000(19) C35 0.025(2) 0.031(2) 0.016(2) 0.0022(18) -0.0025(19) 0.000(2) C36 0.022(2) 0.077(4) 0.016(3) 0.003(3) 0.003(2) 0.008(3) C37 0.030(3) 0.082(4) 0.032(3) -0.022(3) -0.001(2) 0.004(3) C38 0.040(3) 0.121(6) 0.038(4) -0.032(4) -0.001(3) 0.010(4) C39 0.045(4) 0.132(7) 0.037(4) -0.007(5) -0.007(3) 0.022(4) C40 0.040(4) 0.141(8) 0.046(4) 0.036(5) 0.008(3) 0.031(4) C41 0.046(3) 0.084(4) 0.030(3) 0.023(3) 0.008(3) 0.018(3) C42 0.026(2) 0.044(3) 0.020(3) 0.006(2) -0.003(2) -0.002(2) C43 0.025(2) 0.038(3) 0.033(3) 0.001(2) -0.005(2) 0.002(2) C44 0.039(3) 0.057(3) 0.029(3) 0.007(3) -0.008(2) -0.002(3) C45 0.027(3) 0.076(4) 0.044(4) -0.002(3) -0.009(3) -0.008(3) C46 0.026(3) 0.064(4) 0.058(4) 0.004(3) 0.000(3) -0.003(3) C47 0.026(3) 0.054(3) 0.032(3) 0.000(3) 0.004(2) 0.001(2) C48 0.026(2) 0.037(3) 0.027(3) -0.001(2) -0.001(2) 0.002(2) N1 0.024(2) 0.035(2) 0.0148(19) 0.0010(16) 0.0007(16) -0.0020(16) N2 0.037(2) 0.035(2) 0.0083(18) -0.0003(16) 0.0011(16) -0.0026(17) N3 0.027(2) 0.031(2) 0.0135(19) 0.0011(16) 0.0000(16) 0.0014(16) N4 0.026(2) 0.037(2) 0.0115(19) -0.0040(16) 0.0013(15) -0.0005(17) N5 0.037(2) 0.039(2) 0.013(2) -0.0011(17) 0.0024(17) -0.0052(18) N6 0.026(2) 0.034(2) 0.017(2) -0.0026(17) 0.0003(16) -0.0003(16) N7 0.024(2) 0.036(2) 0.016(2) -0.0003(16) 0.0014(16) -0.0003(16) N8 0.026(2) 0.046(2) 0.0113(19) -0.0011(17) 0.0001(16) 0.0021(18) N9 0.0214(19) 0.033(2) 0.017(2) -0.0021(16) -0.0013(16) -0.0010(16) N10 0.026(2) 0.035(2) 0.014(2) 0.0015(16) -0.0001(16) -0.0015(17) N11 0.020(2) 0.047(2) 0.016(2) 0.0058(17) -0.0020(16) -0.0020(17) N12 0.027(2) 0.035(2) 0.017(2) 0.0023(17) 0.0018(16) 0.0016(17) O1 0.040(2) 0.0341(19) 0.0209(19) -0.0005(14) 0.0007(15) -0.0028(15) O2 0.054(2) 0.038(2) 0.027(2) 0.0036(16) 0.0018(17) 0.0000(17) O3 0.0240(17) 0.051(2) 0.0190(18) 0.0048(15) 0.0006(14) 0.0004(15) O4 0.0250(18) 0.058(2) 0.0223(19) -0.0053(16) 0.0020(14) 0.0049(16) Zn1 0.0250(3) 0.0356(3) 0.0134(3) -0.0002(2) 0.0001(2) 0.0001(2) Zn2 0.0262(3) 0.0368(3) 0.0158(3) 0.0015(2) 0.0007(2) 0.0004(2) C51 0.093(8) 0.055(6) 0.040(6) 0.000 0.000 -0.004(5) O11 0.070(3) 0.121(4) 0.018(2) -0.001(2) 0.000(2) -0.009(3) O12 0.121(7) 0.064(5) 0.128(8) 0.000 0.000 0.040(5) F11 0.097(3) 0.155(5) 0.044(3) 0.001(3) 0.012(2) -0.056(3) F12 0.169(8) 0.065(4) 0.120(7) 0.000 0.000 -0.011(5) S1 0.0526(12) 0.0571(13) 0.0241(10) 0.000 0.000 -0.0006(10) C52 0.038(3) 0.079(4) 0.038(4) -0.005(3) 0.000(3) 0.005(3) O21 0.094(4) 0.079(4) 0.097(5) 0.016(3) -0.020(4) -0.030(3) O22 0.063(3) 0.149(5) 0.053(3) -0.048(3) -0.002(3) 0.035(3) O23 0.040(2) 0.108(4) 0.031(2) 0.003(2) -0.0088(19) 0.013(2) F21 0.056(2) 0.123(4) 0.084(4) -0.005(3) -0.035(2) 0.017(2) F22 0.066(3) 0.147(4) 0.059(3) -0.047(3) -0.004(2) 0.014(3) F23 0.093(3) 0.085(3) 0.120(4) 0.011(3) -0.003(3) -0.034(3) S2 0.0404(8) 0.0704(10) 0.0305(8) -0.0068(7) -0.0052(6) 0.0039(7) C53 0.091(9) 0.114(10) 0.045(7) 0.000 0.000 0.020(8) O31 0.109(7) 0.080(5) 0.100(7) 0.000 0.000 0.010(5) O32 0.077(3) 0.115(4) 0.017(2) -0.002(2) 0.002(2) -0.020(3) F31 0.067(3) 0.257(8) 0.088(4) -0.054(5) -0.020(3) -0.016(4) F32 0.090(5) 0.138(7) 0.156(9) 0.000 0.000 0.043(5) S3 0.0478(12) 0.0821(16) 0.0212(10) 0.000 0.000 -0.0047(11) C54 0.075(7) 0.101(8) 0.016(4) 0.000 0.000 0.003(6) O41 0.123(4) 0.093(4) 0.020(2) -0.001(2) -0.003(3) 0.029(3) O42 0.072(6) 0.113(8) 0.212(13) 0.000 0.000 -0.025(5) F41 0.068(5) 0.229(11) 0.140(9) 0.000 0.000 0.008(6) F42 0.168(5) 0.108(4) 0.062(3) 0.020(3) 0.011(3) 0.053(4) S4 0.0700(16) 0.0621(14) 0.0284(12) 0.000 0.000 -0.0028(12) C55 0.049(6) 0.165(12) 0.025(5) 0.000 0.000 -0.008(7) O51 0.140(5) 0.122(5) 0.021(3) -0.001(3) -0.004(3) 0.051(4) O52 0.055(5) 0.134(8) 0.211(13) 0.000 0.000 -0.006(5) F51 0.108(5) 0.112(5) 0.057(4) 0.000 0.000 -0.029(4) F52 0.099(3) 0.105(3) 0.070(3) -0.023(3) 0.002(3) 0.007(3) S5 0.098(2) 0.124(3) 0.0272(13) 0.000 0.000 0.058(2) O63 0.127(10) 0.093(9) 0.053(8) -0.035(7) -0.012(8) 0.032(8) F61 0.107(8) 0.086(7) 0.235(14) -0.035(8) 0.025(8) 0.021(6) F62 0.071(6) 0.141(9) 0.087(8) -0.028(7) -0.019(5) 0.005(6) F63 0.084(6) 0.079(6) 0.123(9) -0.028(6) 0.047(6) -0.034(5) O61 0.215(19) 0.034(6) 0.084(11) 0.025(7) -0.018(12) 0.029(8) O62 0.029(3) 0.031(3) 0.015(3) -0.005(3) 0.003(3) 0.015(3) S6 0.060(3) 0.0419(18) 0.041(2) 0.0007(15) 0.0106(19) 0.0009(19) F61A 0.154(10) 0.092(7) 0.060(7) -0.006(6) -0.028(7) -0.024(7) O61A 0.153(12) 0.064(7) 0.091(10) -0.004(7) 0.044(9) -0.062(8) O62A 0.204(13) 0.091(8) 0.091(10) 0.015(8) 0.059(10) -0.017(9) O63A 0.152(12) 0.181(13) 0.187(13) 0.011(12) -0.009(11) 0.017(11) S6A 0.077(3) 0.083(3) 0.047(3) 0.018(2) 0.006(2) 0.032(3) C1S 0.034(3) 0.064(4) 0.072(5) -0.002(4) 0.005(3) 0.010(3) C2S 0.055(4) 0.135(7) 0.063(5) -0.013(5) 0.019(4) 0.015(4) N1S 0.049(3) 0.097(5) 0.072(5) -0.004(4) -0.002(3) 0.011(3) C3S 0.107(6) 0.051(4) 0.054(5) -0.007(4) 0.013(4) -0.005(4) C4S 0.210(12) 0.092(6) 0.054(6) 0.020(5) 0.001(7) -0.028(7) N2S 0.123(6) 0.051(3) 0.042(4) 0.013(3) 0.011(4) 0.006(3) C5S 0.32(3) 0.126(15) 1.20(8) 0.000 0.000 0.051(18) C6S 0.33(3) 0.102(15) 1.21(8) 0.000 0.000 0.063(19) N3S 0.33(3) 0.115(15) 1.18(8) 0.000 0.000 0.026(19) C7S 0.19(2) 0.121(15) 0.040(8) 0.000 0.000 0.056(14) C8S 0.38(4) 0.16(2) 0.070(12) 0.000 0.000 0.06(2) N4S 0.19(2) 0.31(3) 0.098(13) 0.000 0.000 0.066(19) N5S 0.137(11) 0.30(2) 0.238(17) 0.000 0.000 0.115(13) C10S 0.208(16) 0.179(16) 0.211(19) 0.000 0.000 0.034(15) C9S 0.127(11) 0.155(15) 0.246(16) 0.000 0.000 -0.020(13) O1W 0.27(4) 0.36(6) 0.95(14) 0.000 0.000 0.25(4) O2W 0.13(2) 0.52(7) 0.028(13) 0.000 0.000 0.09(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 C1 O1 1.373(6) . ? C1 C6 1.395(7) . ? C1 C2 1.406(7) . ? C2 C3 1.394(8) . ? C2 H2 0.9500 . ? C3 C4 1.376(8) . ? C3 H3 0.9500 . ? C4 C5 1.381(8) . ? C4 H4 0.9500 . ? C5 C6 1.395(7) . ? C5 H5 0.9500 . ? C6 C7 1.450(7) . ? C7 N1 1.285(6) . ? C7 H7 0.9500 . ? C8 N2 1.348(6) . ? C8 N3 1.368(6) . ? C8 C9 1.383(7) . ? C9 C10 1.388(7) . ? C9 H9 0.9500 . ? C10 N5 1.342(6) . ? C10 N4 1.366(6) . ? C11 N4 1.341(6) . ? C11 N3 1.341(6) . ? C11 C12 1.484(6) . ? C12 C17 1.395(7) . ? C12 C13 1.397(7) . ? C13 C14 1.381(8) . ? C13 H13 0.9500 . ? C14 C15 1.351(10) . ? C14 H14 0.9500 . ? C15 C16 1.426(11) . ? C15 H15 0.9500 . ? C16 C17 1.379(9) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N6 1.298(6) . ? C18 C19 1.452(7) . ? C18 H18 0.9500 . ? C19 C24 1.386(8) . ? C19 C20 1.426(7) . ? C20 C21 1.362(8) . ? C20 H20 0.9500 . ? C21 C22 1.397(9) . ? C21 H21 0.9500 . ? C22 C23 1.385(9) . ? C22 H22 0.9500 . ? C23 C24 1.392(8) . ? C23 H23 0.9500 . ? C24 O2 1.358(6) . ? C25 O3 1.354(6) . ? C25 C26 1.387(7) . ? C25 C30 1.407(7) . ? C26 C27 1.386(8) . ? C26 H26 0.9500 . ? C27 C28 1.392(8) . ? C27 H27 0.9500 . ? C28 C29 1.369(8) . ? C28 H28 0.9500 . ? C29 C30 1.424(7) . ? C29 H29 0.9500 . ? C30 C31 1.440(7) . ? C31 N7 1.286(6) . ? C31 H31 0.9500 . ? C32 N8 1.357(6) . ? C32 N9 1.363(6) . ? C32 C33 1.379(6) 2_565 ? C33 C32 1.379(6) 2_565 ? C33 C34 1.391(6) . ? C33 H33 0.9500 . ? C34 N11 1.344(6) . ? C34 N10 1.370(6) . ? C35 N9 1.326(6) 2_565 ? C35 N10 1.345(6) . ? C35 C36 1.485(6) . ? C36 C41 1.352(8) . ? C36 C37 1.406(8) . ? C37 C38 1.408(9) . ? C37 H37 0.9500 . ? C38 C39 1.321(11) . ? C38 H38 0.9500 . ? C39 C40 1.390(12) . ? C39 H39 0.9500 . ? C40 C41 1.425(10) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 N12 1.298(6) . ? C42 C43 1.439(7) . ? C42 H42 0.9500 . ? C43 C48 1.401(7) . ? C43 C44 1.412(7) . ? C44 C45 1.361(8) . ? C44 H44 0.9500 . ? C45 C46 1.380(9) . ? C45 H45 0.9500 . ? C46 C47 1.385(8) . ? C46 H46 0.9500 . ? C47 C48 1.373(7) . ? C47 H47 0.9500 . ? C48 O4 1.376(6) . ? N1 N2 1.392(5) . ? N1 Zn1 2.094(4) . ? N2 H2A 0.8800 . ? N3 Zn1 2.147(4) . ? N4 Zn2 2.125(4) . ? N5 N6 1.373(5) . ? N5 H5A 0.8800 . ? N6 Zn2 2.094(4) . ? N7 N8 1.375(5) . ? N7 Zn1 2.109(4) . ? N8 H8 0.8800 . ? N9 C35 1.326(6) 2_565 ? N9 Zn1 2.147(4) . ? N10 Zn2 2.148(4) . ? N11 N12 1.367(5) . ? N11 H11 0.8800 . ? N12 Zn2 2.104(4) . ? O1 Zn1 2.213(3) . ? O1 H1 0.9500 . ? O2 Zn2 2.186(4) . ? O2 H2B 0.9500 . ? O3 Zn1 2.216(3) . ? O3 H3A 0.9500 . ? O4 Zn2 2.214(3) . ? O4 H4A 0.9500 . ? C51 F12 1.273(12) . ? C51 F11 1.354(8) 6_556 ? C51 F11 1.354(8) . ? C51 S1 1.805(10) . ? O11 S1 1.432(4) . ? O12 S1 1.415(7) . ? S1 O11 1.432(4) 6_556 ? C52 F23 1.296(8) . ? C52 F22 1.308(7) . ? C52 F21 1.333(7) . ? C52 S2 1.815(7) . ? O21 S2 1.430(6) . ? O22 S2 1.433(5) . ? O23 S2 1.432(4) . ? C53 F32 1.312(14) . ? C53 F31 1.337(9) . ? C53 F31 1.337(9) 6 ? C53 S3 1.773(13) . ? O31 S3 1.423(8) . ? O32 S3 1.414(4) . ? S3 O32 1.414(4) 6 ? C54 F42 1.287(7) . ? C54 F42 1.287(7) 6_556 ? C54 F41 1.355(13) . ? C54 S4 1.805(11) . ? O41 S4 1.402(5) . ? O42 S4 1.416(9) . ? S4 O41 1.402(5) 6_556 ? C55 F51 1.244(12) . ? C55 F52 1.447(10) 6 ? C55 F52 1.447(10) . ? C55 S5 1.714(12) . ? O51 S5 1.329(5) . ? O52 S5 1.623(10) . ? S5 O51 1.329(5) 6 ? C56 F63 1.315(4) . ? C56 F62 1.320(4) . ? C56 F61 1.327(4) . ? C56 S6 1.828(4) . ? O63 S6 1.440(4) . ? O61 S6 1.453(4) . ? O62 S6 1.433(4) . ? F61A C56A 1.316(5) . ? F62A C56A 1.325(5) . ? F63A C56A 1.331(5) . ? C56A S6A 1.822(4) . ? O61A S6A 1.454(4) . ? O62A S6A 1.433(4) . ? O63A S6A 1.439(4) . ? C1S N1S 1.141(9) . ? C1S C2S 1.460(11) . ? C3S N2S 1.127(9) . ? C3S C4S 1.479(12) . ? C5S N3S 1.141(15) . ? C5S C6S 1.522(15) . ? C7S N4S 1.14(3) . ? C7S C8S 1.52(3) . ? N5S C9S 1.168(15) . ? C10S C9S 1.535(15) . ? O1W O2W 1.72(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 119.8(4) . . ? O1 C1 C2 120.3(5) . . ? C6 C1 C2 119.9(5) . . ? C3 C2 C1 119.1(5) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.6(5) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 118.6(5) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 122.1(5) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C1 C6 C5 118.7(5) . . ? C1 C6 C7 124.7(5) . . ? C5 C6 C7 116.5(5) . . ? N1 C7 C6 126.7(5) . . ? N1 C7 H7 116.7 . . ? C6 C7 H7 116.7 . . ? N2 C8 N3 117.5(4) . . ? N2 C8 C9 119.9(4) . . ? N3 C8 C9 122.6(4) . . ? C8 C9 C10 117.0(4) . . ? C8 C9 H9 121.5 . . ? C10 C9 H9 121.5 . . ? N5 C10 N4 117.7(4) . . ? N5 C10 C9 121.1(4) . . ? N4 C10 C9 121.2(4) . . ? N4 C11 N3 125.5(4) . . ? N4 C11 C12 117.8(4) . . ? N3 C11 C12 116.6(4) . . ? C17 C12 C13 120.2(5) . . ? C17 C12 C11 120.8(5) . . ? C13 C12 C11 119.0(4) . . ? C14 C13 C12 119.3(6) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 121.5(6) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 119.7(6) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 119.6(6) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C12 119.6(6) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? N6 C18 C19 125.5(5) . . ? N6 C18 H18 117.2 . . ? C19 C18 H18 117.2 . . ? C24 C19 C20 118.5(5) . . ? C24 C19 C18 125.8(5) . . ? C20 C19 C18 115.8(5) . . ? C21 C20 C19 121.4(6) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 118.8(6) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C23 C22 C21 121.2(6) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 119.7(6) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? O2 C24 C19 119.3(5) . . ? O2 C24 C23 120.2(5) . . ? C19 C24 C23 120.4(5) . . ? O3 C25 C26 121.4(5) . . ? O3 C25 C30 118.7(4) . . ? C26 C25 C30 119.9(5) . . ? C27 C26 C25 121.2(5) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 120.0(5) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 119.4(5) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C28 C29 C30 121.9(5) . . ? C28 C29 H29 119.0 . . ? C30 C29 H29 119.0 . . ? C25 C30 C29 117.6(5) . . ? C25 C30 C31 125.7(4) . . ? C29 C30 C31 116.6(5) . . ? N7 C31 C30 126.3(5) . . ? N7 C31 H31 116.8 . . ? C30 C31 H31 116.8 . . ? N8 C32 N9 117.4(4) . . ? N8 C32 C33 120.6(4) . 2_565 ? N9 C32 C33 122.0(4) . 2_565 ? C32 C33 C34 116.2(4) 2_565 . ? C32 C33 H33 121.9 2_565 . ? C34 C33 H33 121.9 . . ? N11 C34 N10 116.8(4) . . ? N11 C34 C33 120.5(4) . . ? N10 C34 C33 122.7(4) . . ? N9 C35 N10 125.2(4) 2_565 . ? N9 C35 C36 116.7(4) 2_565 . ? N10 C35 C36 118.0(4) . . ? C41 C36 C37 120.2(6) . . ? C41 C36 C35 122.8(6) . . ? C37 C36 C35 117.1(5) . . ? C36 C37 C38 120.1(7) . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C39 C38 C37 117.7(7) . . ? C39 C38 H38 121.1 . . ? C37 C38 H38 121.1 . . ? C38 C39 C40 125.2(7) . . ? C38 C39 H39 117.4 . . ? C40 C39 H39 117.4 . . ? C39 C40 C41 116.4(7) . . ? C39 C40 H40 121.8 . . ? C41 C40 H40 121.8 . . ? C36 C41 C40 120.4(7) . . ? C36 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? N12 C42 C43 126.4(5) . . ? N12 C42 H42 116.8 . . ? C43 C42 H42 116.8 . . ? C48 C43 C44 117.8(5) . . ? C48 C43 C42 125.9(5) . . ? C44 C43 C42 116.2(5) . . ? C45 C44 C43 121.3(5) . . ? C45 C44 H44 119.3 . . ? C43 C44 H44 119.3 . . ? C44 C45 C46 119.2(5) . . ? C44 C45 H45 120.4 . . ? C46 C45 H45 120.4 . . ? C45 C46 C47 121.5(5) . . ? C45 C46 H46 119.3 . . ? C47 C46 H46 119.3 . . ? C48 C47 C46 119.1(5) . . ? C48 C47 H47 120.4 . . ? C46 C47 H47 120.4 . . ? C47 C48 O4 120.3(5) . . ? C47 C48 C43 121.0(5) . . ? O4 C48 C43 118.7(4) . . ? C7 N1 N2 113.8(4) . . ? C7 N1 Zn1 134.0(3) . . ? N2 N1 Zn1 112.2(3) . . ? C8 N2 N1 119.6(4) . . ? C8 N2 H2A 120.2 . . ? N1 N2 H2A 120.2 . . ? C11 N3 C8 116.1(4) . . ? C11 N3 Zn1 131.5(3) . . ? C8 N3 Zn1 112.4(3) . . ? C11 N4 C10 117.3(4) . . ? C11 N4 Zn2 130.2(3) . . ? C10 N4 Zn2 112.4(3) . . ? C10 N5 N6 119.6(4) . . ? C10 N5 H5A 120.2 . . ? N6 N5 H5A 120.2 . . ? C18 N6 N5 114.4(4) . . ? C18 N6 Zn2 133.4(3) . . ? N5 N6 Zn2 112.2(3) . . ? C31 N7 N8 115.0(4) . . ? C31 N7 Zn1 132.7(3) . . ? N8 N7 Zn1 112.3(3) . . ? C32 N8 N7 119.8(4) . . ? C32 N8 H8 120.1 . . ? N7 N8 H8 120.1 . . ? C35 N9 C32 117.8(4) 2_565 . ? C35 N9 Zn1 129.5(3) 2_565 . ? C32 N9 Zn1 112.7(3) . . ? C35 N10 C34 116.0(4) . . ? C35 N10 Zn2 131.2(3) . . ? C34 N10 Zn2 112.6(3) . . ? C34 N11 N12 120.6(4) . . ? C34 N11 H11 119.7 . . ? N12 N11 H11 119.7 . . ? C42 N12 N11 115.3(4) . . ? C42 N12 Zn2 132.4(3) . . ? N11 N12 Zn2 112.3(3) . . ? C1 O1 Zn1 133.6(3) . . ? C1 O1 H1 113.2 . . ? Zn1 O1 H1 113.2 . . ? C24 O2 Zn2 134.6(3) . . ? C24 O2 H2B 112.7 . . ? Zn2 O2 H2B 112.7 . . ? C25 O3 Zn1 132.5(3) . . ? C25 O3 H3A 113.8 . . ? Zn1 O3 H3A 113.8 . . ? C48 O4 Zn2 131.7(3) . . ? C48 O4 H4A 114.2 . . ? Zn2 O4 H4A 114.2 . . ? N1 Zn1 N7 162.69(15) . . ? N1 Zn1 N9 115.23(14) . . ? N7 Zn1 N9 77.70(14) . . ? N1 Zn1 N3 78.04(14) . . ? N7 Zn1 N3 112.95(14) . . ? N9 Zn1 N3 97.44(14) . . ? N1 Zn1 O1 80.25(14) . . ? N7 Zn1 O1 89.47(13) . . ? N9 Zn1 O1 86.74(13) . . ? N3 Zn1 O1 157.58(13) . . ? N1 Zn1 O3 85.47(13) . . ? N7 Zn1 O3 80.47(13) . . ? N9 Zn1 O3 157.84(13) . . ? N3 Zn1 O3 94.50(13) . . ? O1 Zn1 O3 89.31(13) . . ? N6 Zn2 N12 164.43(16) . . ? N6 Zn2 N4 78.03(15) . . ? N12 Zn2 N4 113.70(15) . . ? N6 Zn2 N10 110.82(15) . . ? N12 Zn2 N10 77.47(15) . . ? N4 Zn2 N10 103.14(14) . . ? N6 Zn2 O2 80.65(15) . . ? N12 Zn2 O2 86.54(14) . . ? N4 Zn2 O2 158.20(14) . . ? N10 Zn2 O2 88.63(14) . . ? N6 Zn2 O4 89.27(13) . . ? N12 Zn2 O4 80.92(14) . . ? N4 Zn2 O4 89.54(14) . . ? N10 Zn2 O4 157.93(14) . . ? O2 Zn2 O4 85.65(15) . . ? F12 C51 F11 107.9(6) . 6_556 ? F12 C51 F11 107.9(6) . . ? F11 C51 F11 105.6(9) 6_556 . ? F12 C51 S1 114.2(8) . . ? F11 C51 S1 110.5(5) 6_556 . ? F11 C51 S1 110.5(5) . . ? O12 S1 O11 115.0(3) . . ? O12 S1 O11 115.0(3) . 6_556 ? O11 S1 O11 114.9(4) . 6_556 ? O12 S1 C51 104.9(5) . . ? O11 S1 C51 102.3(3) . . ? O11 S1 C51 102.3(3) 6_556 . ? F23 C52 F22 111.3(6) . . ? F23 C52 F21 107.5(5) . . ? F22 C52 F21 107.2(6) . . ? F23 C52 S2 110.3(5) . . ? F22 C52 S2 111.2(4) . . ? F21 C52 S2 109.2(5) . . ? O21 S2 O23 113.1(3) . . ? O21 S2 O22 117.8(4) . . ? O23 S2 O22 113.7(3) . . ? O21 S2 C52 105.4(3) . . ? O23 S2 C52 103.2(3) . . ? O22 S2 C52 101.2(3) . . ? F32 C53 F31 106.5(8) . . ? F32 C53 F31 106.5(8) . 6 ? F31 C53 F31 108.8(12) . 6 ? F32 C53 S3 111.9(10) . . ? F31 C53 S3 111.4(7) . . ? F31 C53 S3 111.4(7) 6 . ? O32 S3 O32 115.9(4) 6 . ? O32 S3 O31 113.2(3) 6 . ? O32 S3 O31 113.2(3) . . ? O32 S3 C53 105.0(3) 6 . ? O32 S3 C53 105.0(3) . . ? O31 S3 C53 102.9(6) . . ? F42 C54 F42 116.9(10) . 6_556 ? F42 C54 F41 101.1(7) . . ? F42 C54 F41 101.1(7) 6_556 . ? F42 C54 S4 114.4(5) . . ? F42 C54 S4 114.4(5) 6_556 . ? F41 C54 S4 106.1(8) . . ? O41 S4 O41 115.3(5) 6_556 . ? O41 S4 O42 113.1(3) 6_556 . ? O41 S4 O42 113.1(3) . . ? O41 S4 C54 104.3(3) 6_556 . ? O41 S4 C54 104.3(3) . . ? O42 S4 C54 105.5(6) . . ? F51 C55 F52 106.4(6) . 6 ? F51 C55 F52 106.4(6) . . ? F52 C55 F52 97.5(10) 6 . ? F51 C55 S5 116.1(11) . . ? F52 C55 S5 114.3(5) 6 . ? F52 C55 S5 114.3(5) . . ? O51 S5 O51 130.9(6) 6 . ? O51 S5 O52 105.4(4) 6 . ? O51 S5 O52 105.4(4) . . ? O51 S5 C55 104.6(3) 6 . ? O51 S5 C55 104.6(3) . . ? O52 S5 C55 102.8(6) . . ? F63 C56 F62 108.0(4) . . ? F63 C56 F61 108.0(4) . . ? F62 C56 F61 107.7(4) . . ? F63 C56 S6 111.8(4) . . ? F62 C56 S6 110.0(4) . . ? F61 C56 S6 111.0(4) . . ? O62 S6 O63 116.4(4) . . ? O62 S6 O61 115.8(4) . . ? O63 S6 O61 115.0(4) . . ? O62 S6 C56 102.3(3) . . ? O63 S6 C56 102.7(3) . . ? O61 S6 C56 101.3(3) . . ? F61A C56A F62A 107.9(4) . . ? F61A C56A F63A 106.9(4) . . ? F62A C56A F63A 106.9(4) . . ? F61A C56A S6A 112.5(4) . . ? F62A C56A S6A 111.4(4) . . ? F63A C56A S6A 110.9(4) . . ? O62A S6A O63A 116.4(4) . . ? O62A S6A O61A 115.1(4) . . ? O63A S6A O61A 114.4(4) . . ? O62A S6A C56A 102.7(3) . . ? O63A S6A C56A 103.0(4) . . ? O61A S6A C56A 102.4(3) . . ? N1S C1S C2S 179.4(9) . . ? N2S C3S C4S 177.8(10) . . ? N3S C5S C6S 171(4) . . ? N4S C7S C8S 171(2) . . ? N5S C9S C10S 155.3(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.569 _refine_diff_density_min -1.381 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 951972'