# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gabor Speier' _publ_contact_author_address ; Department of Organic Chemistry University of Pnnonia Veszprem 8200 HUNGARY ; _publ_contact_author_email SPEIER@ALMOS.VEIN.HU _publ_section_title ; Manganese and iron flavonolates as flavonol 2,4-dioxygenase mimics ; loop_ _publ_author_name 'Gabor Speier' 'Gabor Barath' 'Michel Giorgi' 'Jozsef Kaizer' 'Jozsef Pap' 'Marius Reglier' data_1 _database_code_depnum_ccdc_archive 'CCDC 651207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H33 Fe O12' _chemical_formula_weight 857.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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 P31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, z+1/2' '-x, -x+y, z+1/2' 'x-y, -y, z+1/2' _cell_length_a 15.4880(5) _cell_length_b 15.4880(5) _cell_length_c 19.9970(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4154.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3727 _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 22.71 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max .3 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1772 _exptl_absorpt_coefficient_mu 0.429 _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 KappaCCD _diffrn_measurement_method 'Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3568 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 22.70 _reflns_number_total 2081 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Bruker-Nonius, 1998)' _computing_cell_refinement 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; Altamore, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. and Camalli, M. J. Appl. Cryst. (1994) 27, 435-436 Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box 811, 2600 Av, Delft, The Netherlands. Otwinowski, Z. and Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode , Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. Univ. of G\"ottingen, Germany. ; _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^)+(0.1136P)^2^+9.3277P] 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 0.48(5) _refine_ls_number_reflns 2081 _refine_ls_number_parameters 367 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.1992 _refine_ls_wR_factor_gt 0.1901 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 22.70 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.433 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.074 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 Fe1 Fe 1.3330 0.6670 0.15255(12) 0.0356(6) Uani 1 3 d S . . Fe2 Fe 1.0000 0.0000 0.31488(14) 0.0438(7) Uani 1 3 d S . . O1 O 1.2900(6) 0.5440(6) 0.0874(4) 0.049(2) Uani 1 1 d . . . O2 O 1.2229(6) 0.5610(5) 0.2037(3) 0.0390(18) Uani 1 1 d . . . O3 O 1.0778(6) 0.2933(6) 0.1801(4) 0.0435(18) Uani 1 1 d . . . O4 O 0.8867(10) 0.3481(8) 0.4391(6) 0.107(5) Uani 1 1 d . . . O5 O 1.0716(5) 0.1271(6) 0.3614(4) 0.047(2) Uani 1 1 d . . . O6 O 1.1190(6) 0.0774(6) 0.2495(4) 0.055(2) Uani 1 1 d . . . O7 O 1.2787(6) 0.3652(6) 0.3065(4) 0.057(2) Uani 1 1 d . . . O8 O 1.1647(10) 0.4913(9) 0.5711(6) 0.100(4) Uani 1 1 d . . . C1 C 1.2226(8) 0.4644(7) 0.1178(5) 0.032(2) Uani 1 1 d . . . C2 C 1.1809(9) 0.3675(8) 0.0819(6) 0.048(3) Uani 1 1 d . . . C3 C 1.2086(9) 0.3516(9) 0.0225(6) 0.053(3) Uani 1 1 d . . . H3 H 1.2568 0.4059 -0.0014 0.063 Uiso 1 1 calc R . . C4 C 1.1678(11) 0.2553(11) -0.0059(7) 0.063(4) Uani 1 1 d . . . H4 H 1.1830 0.2458 -0.0493 0.076 Uiso 1 1 calc R . . C5 C 1.1027(10) 0.1748(10) 0.0351(5) 0.051(3) Uani 1 1 d . . . H5 H 1.0804 0.1104 0.0195 0.061 Uiso 1 1 calc R . . C6 C 1.0712(9) 0.1856(9) 0.0950(8) 0.065(4) Uani 1 1 d . . . H6 H 1.0242 0.1302 0.1186 0.078 Uiso 1 1 calc R . . C7 C 1.1110(8) 0.2839(9) 0.1223(6) 0.046(3) Uani 1 1 d . . . C8 C 1.1116(8) 0.3851(9) 0.2090(5) 0.039(3) Uani 1 1 d . . . C9 C 1.1853(8) 0.4722(8) 0.1785(5) 0.037(3) Uani 1 1 d . . . C10 C 1.0557(9) 0.3765(9) 0.2726(5) 0.041(3) Uani 1 1 d . . . C11 C 0.9735(11) 0.2881(10) 0.2884(6) 0.061(4) Uani 1 1 d . . . H11 H 0.9531 0.2331 0.2606 0.073 Uiso 1 1 calc R . . C12 C 0.9191(13) 0.2804(12) 0.3474(8) 0.082(5) Uani 1 1 d . . . H12 H 0.8645 0.2195 0.3595 0.098 Uiso 1 1 calc R . . C13 C 0.9474(12) 0.3638(11) 0.3869(7) 0.067(4) Uani 1 1 d . . . C14 C 1.0295(11) 0.4512(11) 0.3704(7) 0.066(4) Uani 1 1 d . . . H14 H 1.0493 0.5072 0.3971 0.080 Uiso 1 1 calc R . . C15 C 1.0848(10) 0.4572(10) 0.3131(5) 0.051(3) Uani 1 1 d . . . H15 H 1.1420 0.5170 0.3026 0.062 Uiso 1 1 calc R . . C16 C 0.9095(17) 0.4322(14) 0.4805(9) 0.114(8) Uani 1 1 d . . . H16A H 0.8612 0.4121 0.5158 0.171 Uiso 1 1 calc R . . H16B H 0.9081 0.4832 0.4542 0.171 Uiso 1 1 calc R . . H16C H 0.9747 0.4575 0.4995 0.171 Uiso 1 1 calc R . . C17 C 1.1479(8) 0.1978(8) 0.3270(6) 0.041(3) Uani 1 1 d . . . C18 C 1.1717(8) 0.1675(9) 0.2665(5) 0.042(3) Uani 1 1 d . . . C19 C 1.2529(8) 0.2406(9) 0.2258(7) 0.050(3) Uani 1 1 d . . . C20 C 1.2817(9) 0.2202(10) 0.1644(6) 0.049(3) Uani 1 1 d . . . H20 H 1.2504 0.1554 0.1479 0.059 Uiso 1 1 calc R . . C21 C 1.3563(10) 0.2962(11) 0.1288(7) 0.062(4) Uani 1 1 d . . . H21 H 1.3762 0.2820 0.0884 0.074 Uiso 1 1 calc R . . C22 C 1.4034(11) 0.3944(11) 0.1515(6) 0.065(4) Uani 1 1 d . . . H22 H 1.4548 0.4451 0.1269 0.078 Uiso 1 1 calc R . . C23 C 1.3745(9) 0.4138(10) 0.2072(7) 0.059(4) Uani 1 1 d . . . H23 H 1.4024 0.4799 0.2207 0.071 Uiso 1 1 calc R . . C24 C 1.3022(8) 0.3387(9) 0.2483(5) 0.044(3) Uani 1 1 d . . . C25 C 1.2032(8) 0.2967(9) 0.3488(6) 0.042(3) Uani 1 1 d . . . C26 C 1.1919(10) 0.3451(9) 0.4056(6) 0.049(3) Uani 1 1 d . . . C27 C 1.2603(10) 0.4449(9) 0.4199(8) 0.064(4) Uani 1 1 d . . . H27 H 1.3139 0.4806 0.3913 0.077 Uiso 1 1 calc R . . C28 C 1.2500(10) 0.4917(10) 0.4755(7) 0.063(4) Uani 1 1 d . . . H28 H 1.2960 0.5586 0.4831 0.076 Uiso 1 1 calc R . . C29 C 1.1711(11) 0.4399(10) 0.5209(8) 0.066(4) Uani 1 1 d . . . C30 C 1.1019(12) 0.3411(11) 0.5081(9) 0.080(5) Uani 1 1 d . . . H30 H 1.0491 0.3059 0.5374 0.096 Uiso 1 1 calc R . . C31 C 1.1116(9) 0.2937(9) 0.4506(6) 0.050(3) Uani 1 1 d . . . H31 H 1.0643 0.2275 0.4421 0.060 Uiso 1 1 calc R . . C32 C 1.104(2) 0.4455(19) 0.6293(10) 0.133(9) Uani 1 1 d . . . H32A H 1.1106 0.4963 0.6596 0.199 Uiso 1 1 calc R . . H32B H 1.1266 0.4047 0.6510 0.199 Uiso 1 1 calc R . . H32C H 1.0360 0.4049 0.6162 0.199 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 Fe1 0.0323(14) 0.042 0.0361(12) 0.000 0.000 0.021 Fe2 0.0322(14) 0.039 0.0625(17) 0.000 0.000 0.019 O1 0.042(5) 0.037(5) 0.067(5) -0.003(4) 0.004(4) 0.019(4) O2 0.043(5) 0.029(4) 0.043(4) -0.008(3) 0.002(3) 0.017(4) O3 0.044(5) 0.038(4) 0.045(4) -0.005(4) 0.008(4) 0.018(4) O4 0.135(11) 0.076(8) 0.112(9) 0.030(7) 0.091(8) 0.055(8) O5 0.031(4) 0.030(4) 0.071(5) 0.005(4) 0.007(4) 0.008(4) O6 0.049(5) 0.033(5) 0.087(6) -0.007(4) 0.003(4) 0.023(4) O7 0.048(5) 0.038(5) 0.070(6) -0.005(4) 0.003(4) 0.011(4) O8 0.121(10) 0.093(8) 0.096(8) -0.036(7) 0.003(8) 0.062(8) C1 0.033(6) 0.030(6) 0.034(5) 0.002(5) 0.000(5) 0.016(5) C2 0.034(6) 0.039(7) 0.076(8) -0.004(6) 0.006(6) 0.023(6) C3 0.054(8) 0.043(7) 0.059(7) -0.008(6) 0.011(6) 0.023(6) C4 0.064(9) 0.062(9) 0.064(8) -0.009(7) 0.004(7) 0.032(8) C5 0.065(9) 0.051(8) 0.044(7) -0.018(6) 0.002(6) 0.035(7) C6 0.034(7) 0.027(7) 0.126(12) -0.024(7) -0.019(7) 0.010(6) C7 0.036(6) 0.046(7) 0.051(7) -0.006(6) 0.001(5) 0.018(6) C8 0.034(6) 0.054(7) 0.037(6) 0.001(5) -0.004(5) 0.028(6) C9 0.024(6) 0.044(7) 0.036(6) 0.004(5) 0.009(5) 0.013(5) C10 0.048(7) 0.046(7) 0.037(6) 0.007(5) 0.012(5) 0.029(6) C11 0.075(10) 0.062(9) 0.044(7) 0.009(6) 0.033(7) 0.033(8) C12 0.086(11) 0.067(10) 0.073(9) 0.012(9) 0.040(9) 0.023(9) C13 0.079(10) 0.068(10) 0.067(9) 0.026(8) 0.033(8) 0.047(9) C14 0.066(9) 0.050(8) 0.089(10) 0.009(7) 0.025(8) 0.033(8) C15 0.059(8) 0.063(8) 0.041(6) 0.018(6) 0.028(6) 0.036(7) C16 0.18(2) 0.097(14) 0.081(10) 0.019(10) 0.064(13) 0.082(15) C17 0.038(6) 0.033(7) 0.062(7) -0.005(5) -0.006(6) 0.025(6) C18 0.033(6) 0.050(8) 0.043(6) -0.001(5) -0.003(5) 0.021(6) C19 0.030(6) 0.038(7) 0.085(9) 0.013(6) 0.008(6) 0.019(6) C20 0.042(7) 0.052(8) 0.059(8) -0.006(6) 0.005(6) 0.027(6) C21 0.058(9) 0.070(10) 0.059(8) 0.008(7) 0.012(7) 0.033(8) C22 0.068(9) 0.065(10) 0.054(8) 0.017(7) 0.027(7) 0.027(8) C23 0.047(8) 0.034(7) 0.082(10) 0.012(7) 0.012(7) 0.011(6) C24 0.040(7) 0.044(7) 0.048(6) 0.002(5) 0.003(5) 0.021(6) C25 0.039(7) 0.039(7) 0.051(6) 0.004(5) 0.000(5) 0.021(6) C26 0.051(8) 0.042(7) 0.064(8) -0.006(6) -0.007(6) 0.031(7) C27 0.051(8) 0.026(7) 0.098(10) -0.006(7) 0.010(7) 0.006(6) C28 0.049(8) 0.043(7) 0.080(8) -0.012(7) 0.009(7) 0.010(7) C29 0.061(9) 0.047(8) 0.094(11) -0.016(7) -0.022(8) 0.030(8) C30 0.063(10) 0.049(9) 0.130(14) 0.009(9) 0.020(9) 0.030(8) C31 0.053(8) 0.037(7) 0.049(6) -0.001(6) 0.005(6) 0.014(6) C32 0.21(3) 0.15(2) 0.091(14) 0.011(14) 0.002(16) 0.13(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O2 1.956(7) 3_775 ? Fe1 O2 1.962(7) . ? Fe1 O2 1.969(7) 2_755 ? Fe1 O1 2.111(8) 3_775 ? Fe1 O1 2.120(8) 2_755 ? Fe1 O1 2.122(8) . ? Fe2 O5 1.947(8) 2_645 ? Fe2 O5 1.947(8) 3_765 ? Fe2 O5 1.947(8) . ? Fe2 O6 2.081(9) 3_765 ? Fe2 O6 2.081(9) . ? Fe2 O6 2.081(9) 2_645 ? O1 C1 1.301(12) . ? O2 C9 1.298(13) . ? O3 C7 1.303(13) . ? O3 C8 1.373(13) . ? O4 C13 1.343(15) . ? O4 C16 1.430(19) . ? O5 C17 1.332(13) . ? O6 C18 1.260(14) . ? O7 C24 1.343(13) . ? O7 C25 1.403(14) . ? O8 C29 1.314(17) . ? O8 C32 1.44(2) . ? C1 C9 1.375(14) . ? C1 C2 1.490(14) . ? C2 C3 1.327(15) . ? C2 C7 1.448(16) . ? C3 C4 1.415(18) . ? C3 H3 0.9300 . ? C4 C5 1.410(19) . ? C4 H4 0.9300 . ? C5 C6 1.334(17) . ? C5 H5 0.9300 . ? C6 C7 1.435(17) . ? C6 H6 0.9300 . ? C8 C9 1.398(15) . ? C8 C10 1.507(14) . ? C10 C11 1.360(17) . ? C10 C15 1.362(17) . ? C11 C12 1.421(18) . ? C11 H11 0.9300 . ? C12 C13 1.38(2) . ? C12 H12 0.9300 . ? C13 C14 1.355(19) . ? C14 C15 1.407(17) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C25 1.399(16) . ? C17 C18 1.412(16) . ? C18 C19 1.450(16) . ? C19 C24 1.391(17) . ? C19 C20 1.395(17) . ? C20 C21 1.367(18) . ? C20 H20 0.9300 . ? C21 C22 1.39(2) . ? C21 H21 0.9300 . ? C22 C23 1.292(18) . ? C22 H22 0.9300 . ? C23 C24 1.407(17) . ? C23 H23 0.9300 . ? C25 C26 1.418(16) . ? C26 C27 1.399(17) . ? C26 C31 1.414(17) . ? C27 C28 1.378(19) . ? C27 H27 0.9300 . ? C28 C29 1.41(2) . ? C28 H28 0.9300 . ? C29 C30 1.38(2) . ? C30 C31 1.413(19) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Fe1 O2 95.5(3) 3_775 . ? O2 Fe1 O2 95.3(3) 3_775 2_755 ? O2 Fe1 O2 95.1(3) . 2_755 ? O2 Fe1 O1 79.9(3) 3_775 3_775 ? O2 Fe1 O1 100.8(3) . 3_775 ? O2 Fe1 O1 163.7(3) 2_755 3_775 ? O2 Fe1 O1 100.7(3) 3_775 2_755 ? O2 Fe1 O1 163.3(3) . 2_755 ? O2 Fe1 O1 79.4(3) 2_755 2_755 ? O1 Fe1 O1 86.2(3) 3_775 2_755 ? O2 Fe1 O1 164.1(3) 3_775 . ? O2 Fe1 O1 79.5(3) . . ? O2 Fe1 O1 100.2(3) 2_755 . ? O1 Fe1 O1 86.1(3) 3_775 . ? O1 Fe1 O1 85.9(3) 2_755 . ? O5 Fe2 O5 99.0(3) 2_645 3_765 ? O5 Fe2 O5 99.0(3) 2_645 . ? O5 Fe2 O5 99.0(3) 3_765 . ? O5 Fe2 O6 96.5(3) 2_645 3_765 ? O5 Fe2 O6 79.9(3) 3_765 3_765 ? O5 Fe2 O6 164.4(3) . 3_765 ? O5 Fe2 O6 164.4(3) 2_645 . ? O5 Fe2 O6 96.5(3) 3_765 . ? O5 Fe2 O6 79.9(3) . . ? O6 Fe2 O6 84.8(4) 3_765 . ? O5 Fe2 O6 79.9(3) 2_645 2_645 ? O5 Fe2 O6 164.4(3) 3_765 2_645 ? O5 Fe2 O6 96.5(3) . 2_645 ? O6 Fe2 O6 84.8(4) 3_765 2_645 ? O6 Fe2 O6 84.8(4) . 2_645 ? C1 O1 Fe1 107.8(6) . . ? C9 O2 Fe1 115.2(6) . . ? C7 O3 C8 121.5(9) . . ? C13 O4 C16 117.0(13) . . ? C17 O5 Fe2 114.0(7) . . ? C18 O6 Fe2 111.5(7) . . ? C24 O7 C25 122.8(9) . . ? C29 O8 C32 123.1(16) . . ? O1 C1 C9 120.2(9) . . ? O1 C1 C2 117.8(9) . . ? C9 C1 C2 121.7(10) . . ? C3 C2 C7 120.0(11) . . ? C3 C2 C1 127.0(11) . . ? C7 C2 C1 112.7(9) . . ? C2 C3 C4 122.6(12) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C5 C4 C3 116.3(11) . . ? C5 C4 H4 121.8 . . ? C3 C4 H4 121.8 . . ? C6 C5 C4 123.7(13) . . ? C6 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C5 C6 C7 119.0(14) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? O3 C7 C6 118.2(12) . . ? O3 C7 C2 123.7(10) . . ? C6 C7 C2 118.0(11) . . ? O3 C8 C9 121.3(9) . . ? O3 C8 C10 111.0(9) . . ? C9 C8 C10 127.6(10) . . ? O2 C9 C1 116.8(9) . . ? O2 C9 C8 124.8(9) . . ? C1 C9 C8 118.5(10) . . ? C11 C10 C15 120.0(10) . . ? C11 C10 C8 119.5(11) . . ? C15 C10 C8 120.5(10) . . ? C10 C11 C12 119.6(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 119.8(14) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? O4 C13 C14 126.3(15) . . ? O4 C13 C12 114.0(13) . . ? C14 C13 C12 119.6(13) . . ? C13 C14 C15 120.0(14) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.8(13) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 C25 123.0(10) . . ? O5 C17 C18 116.2(10) . . ? C25 C17 C18 120.8(11) . . ? O6 C18 C17 117.8(10) . . ? O6 C18 C19 122.9(11) . . ? C17 C18 C19 119.4(11) . . ? C24 C19 C20 118.0(11) . . ? C24 C19 C18 117.3(11) . . ? C20 C19 C18 124.6(12) . . ? C21 C20 C19 119.4(12) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 121.8(12) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C23 C22 C21 118.8(13) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 122.5(13) . . ? C22 C23 H23 118.8 . . ? C24 C23 H23 118.8 . . ? O7 C24 C19 122.0(11) . . ? O7 C24 C23 118.6(11) . . ? C19 C24 C23 119.3(11) . . ? C17 C25 O7 117.5(10) . . ? C17 C25 C26 131.1(11) . . ? O7 C25 C26 111.1(10) . . ? C27 C26 C31 117.2(11) . . ? C27 C26 C25 121.5(12) . . ? C31 C26 C25 121.2(11) . . ? C28 C27 C26 121.6(13) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C27 C28 C29 121.1(12) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? O8 C29 C30 124.0(16) . . ? O8 C29 C28 117.0(13) . . ? C30 C29 C28 118.8(14) . . ? C29 C30 C31 120.0(14) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C26 121.2(11) . . ? C30 C31 H31 119.4 . . ? C26 C31 H31 119.4 . . ? O8 C32 H32A 109.5 . . ? O8 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O8 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? # Attachment 'pzs108-7_1_.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 651208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H28 Mn N2 O6' _chemical_formula_weight 687.58 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' Mn Mn 0.3368 0.7283 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3100(6) _cell_length_b 10.0950(6) _cell_length_c 11.1670(5) _cell_angle_alpha 113.361(4) _cell_angle_beta 97.542(4) _cell_angle_gamma 106.255(4) _cell_volume 793.82(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2882 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 26.37 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 355 _exptl_absorpt_coefficient_mu 0.470 _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 KappaCCD _diffrn_measurement_method 'Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2882 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2882 _reflns_number_gt 2667 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Brucker-Nonius, 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+0.3239P] 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 2882 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.391 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.123 _publ_section_references ; Brucker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box 811, 2600 Av, Delft, The Netherlands. Otwinowski, Z. and Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode , Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. Univ. of G\"ottingen, Germany. ; 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 Mn1 Mn 0.5000 0.5000 0.5000 0.0359(2) Uani 1 2 d S . . O1 O 0.2656(2) 0.00749(19) 0.02466(17) 0.0409(4) Uani 1 1 d . . . O2 O 0.4608(2) 0.26252(19) 0.38322(17) 0.0393(4) Uani 1 1 d . . . O3 O 0.3375(2) 0.44067(18) 0.30236(18) 0.0401(4) Uani 1 1 d . . . N1 N 0.2453(3) 0.4315(3) 0.5666(2) 0.0444(5) Uani 1 1 d . . . C1 C 0.3796(3) 0.2065(3) 0.2559(2) 0.0333(5) Uani 1 1 d . . . C2 C 0.3550(3) 0.0603(3) 0.1570(2) 0.0351(5) Uani 1 1 d . . . C3 C 0.4117(3) -0.0573(3) 0.1744(3) 0.0367(5) Uani 1 1 d . . . C4 C 0.4870(4) -0.0400(3) 0.3017(3) 0.0490(6) Uani 1 1 d . . . H4 H 0.4975 0.0461 0.3713 0.059 Uiso 1 1 d R . . C5 C 0.5346(4) -0.1553(4) 0.3151(3) 0.0583(7) Uani 1 1 d . . . H5 H 0.5901 -0.1377 0.4052 0.070 Uiso 1 1 d R . . C6 C 0.5110(4) -0.2898(3) 0.2019(4) 0.0575(8) Uani 1 1 d . . . H6 H 0.5546 -0.3669 0.2199 0.069 Uiso 1 1 d R . . C7 C 0.4386(4) -0.3075(3) 0.0756(3) 0.0573(8) Uani 1 1 d . . . H7 H 0.4139 -0.3963 0.0012 0.069 Uiso 1 1 d R . . C8 C 0.3884(4) -0.1952(3) 0.0598(3) 0.0474(6) Uani 1 1 d . . . H8 H 0.3385 -0.1964 -0.0256 0.057 Uiso 1 1 d R . . C9 C 0.3119(3) 0.3057(3) 0.2152(2) 0.0344(5) Uani 1 1 d . . . C10 C 0.2167(3) 0.2446(3) 0.0761(3) 0.0364(5) Uani 1 1 d . . . C11 C 0.1430(3) 0.3296(3) 0.0271(3) 0.0450(6) Uani 1 1 d . . . H11 H 0.1650 0.4421 0.0939 0.054 Uiso 1 1 d R . . C12 C 0.0546(4) 0.2659(4) -0.1064(3) 0.0549(7) Uani 1 1 d . . . H12 H -0.0010 0.3247 -0.1468 0.066 Uiso 1 1 d R . . C13 C 0.0370(4) 0.1142(4) -0.1962(3) 0.0582(8) Uani 1 1 d . . . H13 H -0.0310 0.0836 -0.2868 0.070 Uiso 1 1 d R . . C14 C 0.1079(4) 0.0296(3) -0.1516(3) 0.0505(7) Uani 1 1 d . . . H14 H 0.1078 -0.0764 -0.2090 0.061 Uiso 1 1 d R . . C15 C 0.1977(3) 0.0953(3) -0.0150(3) 0.0396(5) Uani 1 1 d . . . C16 C 0.1343(4) 0.2847(3) 0.5088(3) 0.0524(7) Uani 1 1 d . . . H16 H 0.1753 0.2109 0.4509 0.063 Uiso 1 1 d R . . C17 C -0.0308(4) 0.2412(4) 0.5252(4) 0.0636(8) Uani 1 1 d . . . H17 H -0.1084 0.1415 0.4835 0.076 Uiso 1 1 d R . . C18 C -0.0847(4) 0.3546(4) 0.6077(3) 0.0621(8) Uani 1 1 d . . . H18 H -0.1997 0.3244 0.6214 0.075 Uiso 1 1 d R . . C19 C 0.0296(4) 0.5059(4) 0.6709(3) 0.0587(8) Uani 1 1 d . . . H19 H -0.0185 0.5798 0.7173 0.070 Uiso 1 1 d R . . C20 C 0.1915(4) 0.5389(4) 0.6472(3) 0.0519(7) Uani 1 1 d . . . H20 H 0.2791 0.6534 0.6928 0.062 Uiso 1 1 d 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 Mn1 0.0381(3) 0.0293(3) 0.0303(3) 0.0039(2) 0.0064(2) 0.0138(2) O1 0.0493(10) 0.0306(8) 0.0302(10) 0.0055(8) 0.0072(8) 0.0109(7) O2 0.0483(9) 0.0297(8) 0.0305(10) 0.0044(8) 0.0055(7) 0.0174(7) O3 0.0469(9) 0.0297(8) 0.0366(10) 0.0068(8) 0.0084(7) 0.0175(7) N1 0.0391(10) 0.0490(12) 0.0404(13) 0.0147(11) 0.0105(9) 0.0180(9) C1 0.0337(10) 0.0276(10) 0.0322(13) 0.0079(10) 0.0102(9) 0.0103(8) C2 0.0358(11) 0.0285(10) 0.0343(13) 0.0087(10) 0.0123(10) 0.0094(9) C3 0.0367(11) 0.0264(10) 0.0427(14) 0.0106(11) 0.0168(10) 0.0104(9) C4 0.0616(16) 0.0389(13) 0.0450(16) 0.0131(13) 0.0162(13) 0.0244(12) C5 0.0701(19) 0.0532(16) 0.062(2) 0.0288(16) 0.0213(16) 0.0323(15) C6 0.0667(18) 0.0408(14) 0.078(2) 0.0307(16) 0.0319(17) 0.0272(13) C7 0.0713(19) 0.0296(12) 0.067(2) 0.0128(14) 0.0313(16) 0.0209(12) C8 0.0575(15) 0.0306(12) 0.0452(17) 0.0085(12) 0.0195(13) 0.0141(11) C9 0.0309(10) 0.0314(11) 0.0388(14) 0.0131(11) 0.0136(9) 0.0110(9) C10 0.0316(10) 0.0359(12) 0.0378(14) 0.0152(11) 0.0109(10) 0.0083(9) C11 0.0430(13) 0.0448(14) 0.0474(16) 0.0219(13) 0.0129(11) 0.0148(11) C12 0.0542(16) 0.0632(18) 0.0503(18) 0.0325(16) 0.0085(13) 0.0185(14) C13 0.0601(17) 0.0610(18) 0.0395(18) 0.0221(16) 0.0016(13) 0.0091(14) C14 0.0548(15) 0.0438(14) 0.0350(16) 0.0114(13) 0.0055(12) 0.0054(12) C15 0.0383(12) 0.0361(12) 0.0364(14) 0.0139(12) 0.0101(10) 0.0063(10) C16 0.0489(15) 0.0515(15) 0.0517(18) 0.0187(15) 0.0154(13) 0.0178(12) C17 0.0535(17) 0.0635(19) 0.062(2) 0.0289(18) 0.0105(15) 0.0073(14) C18 0.0471(15) 0.088(2) 0.064(2) 0.0418(19) 0.0240(15) 0.0276(16) C19 0.0540(16) 0.078(2) 0.060(2) 0.0338(18) 0.0294(15) 0.0371(16) C20 0.0461(14) 0.0575(16) 0.0450(17) 0.0136(14) 0.0150(12) 0.0221(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.1274(16) 2_666 ? Mn1 O2 2.1274(16) . ? Mn1 O3 2.1839(18) . ? Mn1 O3 2.1840(18) 2_666 ? Mn1 N1 2.348(2) . ? Mn1 N1 2.348(2) 2_666 ? O1 C15 1.351(3) . ? O1 C2 1.374(3) . ? O2 C1 1.302(3) . ? O3 C9 1.257(3) . ? N1 C16 1.335(4) . ? N1 C20 1.337(3) . ? C1 C2 1.385(3) . ? C1 C9 1.460(3) . ? C2 C3 1.463(3) . ? C3 C4 1.397(4) . ? C3 C8 1.409(3) . ? C4 C5 1.383(4) . ? C4 H4 0.8779 . ? C5 C6 1.380(4) . ? C5 H5 0.9732 . ? C6 C7 1.378(5) . ? C6 H6 1.0208 . ? C7 C8 1.377(4) . ? C7 H7 0.8936 . ? C8 H8 0.9818 . ? C9 C10 1.437(4) . ? C10 C15 1.393(3) . ? C10 C11 1.410(3) . ? C11 C12 1.365(4) . ? C11 H11 1.0278 . ? C12 C13 1.410(5) . ? C12 H12 1.0406 . ? C13 C14 1.367(4) . ? C13 H13 0.9700 . ? C14 C15 1.395(4) . ? C14 H14 1.0052 . ? C16 C17 1.379(4) . ? C16 H16 0.9526 . ? C17 C18 1.385(5) . ? C17 H17 0.9127 . ? C18 C19 1.375(5) . ? C18 H18 0.9705 . ? C19 C20 1.380(4) . ? C19 H19 0.9494 . ? C20 H20 1.0437 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O2 180.0 2_666 . ? O2 Mn1 O3 103.19(6) 2_666 . ? O2 Mn1 O3 76.81(6) . . ? O2 Mn1 O3 76.81(6) 2_666 2_666 ? O2 Mn1 O3 103.19(6) . 2_666 ? O3 Mn1 O3 180.0 . 2_666 ? O2 Mn1 N1 89.01(7) 2_666 . ? O2 Mn1 N1 90.99(7) . . ? O3 Mn1 N1 88.83(7) . . ? O3 Mn1 N1 91.17(7) 2_666 . ? O2 Mn1 N1 90.99(7) 2_666 2_666 ? O2 Mn1 N1 89.01(7) . 2_666 ? O3 Mn1 N1 91.17(7) . 2_666 ? O3 Mn1 N1 88.83(7) 2_666 2_666 ? N1 Mn1 N1 180.0 . 2_666 ? C15 O1 C2 121.70(18) . . ? C1 O2 Mn1 113.52(14) . . ? C9 O3 Mn1 112.31(14) . . ? C16 N1 C20 116.7(2) . . ? C16 N1 Mn1 120.95(18) . . ? C20 N1 Mn1 121.49(19) . . ? O2 C1 C2 124.3(2) . . ? O2 C1 C9 117.46(19) . . ? C2 C1 C9 118.3(2) . . ? O1 C2 C1 121.2(2) . . ? O1 C2 C3 111.17(19) . . ? C1 C2 C3 127.6(2) . . ? C4 C3 C8 117.7(2) . . ? C4 C3 C2 122.6(2) . . ? C8 C3 C2 119.7(2) . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 123.1 . . ? C3 C4 H4 115.6 . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 118.8 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 125.4 . . ? C5 C6 H6 115.6 . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H7 117.2 . . ? C6 C7 H7 120.8 . . ? C7 C8 C3 120.0(3) . . ? C7 C8 H8 127.5 . . ? C3 C8 H8 112.5 . . ? O3 C9 C10 122.1(2) . . ? O3 C9 C1 119.4(2) . . ? C10 C9 C1 118.5(2) . . ? C15 C10 C11 118.4(2) . . ? C15 C10 C9 118.6(2) . . ? C11 C10 C9 123.0(2) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 121.9 . . ? C10 C11 H11 117.6 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 122.9 . . ? C13 C12 H12 117.1 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 128.4 . . ? C12 C13 H13 110.8 . . ? C13 C14 C15 118.9(3) . . ? C13 C14 H14 126.3 . . ? C15 C14 H14 114.7 . . ? O1 C15 C10 121.6(2) . . ? O1 C15 C14 116.9(2) . . ? C10 C15 C14 121.5(2) . . ? N1 C16 C17 123.5(3) . . ? N1 C16 H16 114.9 . . ? C17 C16 H16 121.5 . . ? C16 C17 C18 118.8(3) . . ? C16 C17 H17 123.7 . . ? C18 C17 H17 117.5 . . ? C19 C18 C17 118.5(3) . . ? C19 C18 H18 122.4 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 118.8(3) . . ? C18 C19 H19 114.8 . . ? C20 C19 H19 125.8 . . ? N1 C20 C19 123.7(3) . . ? N1 C20 H20 116.5 . . ? C19 C20 H20 119.8 . . ?