# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Perez-Balado, Carlos' _publ_contact_author_email qolera@uvigo.es _publ_section_title ; Concise Total Synthesis and Structural Revision of (+)-Pestalazine B ; loop_ _publ_author_name C.Perez-Balado 'A.R. de Lera' # Attachment '- ar1658s.cif' data_ar1658s _database_code_depnum_ccdc_archive 'CCDC 767367' #TrackingRef '- ar1658s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H38 N6 O7' _chemical_formula_weight 678.73 _chemical_absolute_configuration syn 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 12.0209(8) _cell_length_b 12.0209(8) _cell_length_c 25.881(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3739.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3206 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 19.68 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 1.000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19786 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6553 _reflns_number_gt 3742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1035P)^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 SHELXL _refine_ls_extinction_coef 0.0070(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(2) _refine_ls_number_reflns 6553 _refine_ls_number_parameters 501 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1936 _refine_ls_wR_factor_gt 0.1525 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N1 N 0.3173(3) 0.8323(3) 0.06817(15) 0.0591(10) Uani 1 1 d . . . H1 H 0.2554 0.8496 0.0828 0.10(2) Uiso 1 1 calc R . . C2 C 0.3995(3) 0.9122(3) 0.05126(17) 0.0484(10) Uani 1 1 d . . . H2 H 0.4277 0.9558 0.0804 0.037(10) Uiso 1 1 calc R . . C3 C 0.4949(3) 0.8395(3) 0.02656(16) 0.0457(10) Uani 1 1 d . . . C4 C 0.4560(4) 0.7226(3) 0.03660(17) 0.0490(10) Uani 1 1 d . . . C5 C 0.5076(5) 0.6235(4) 0.0253(2) 0.0670(13) Uani 1 1 d . . . H5 H 0.5781 0.6224 0.0105 0.084(18) Uiso 1 1 calc R . . C6 C 0.4520(5) 0.5251(4) 0.0366(2) 0.0803(16) Uani 1 1 d . . . H6 H 0.4864 0.4571 0.0305 0.066(14) Uiso 1 1 calc R . . C7 C 0.3467(6) 0.5285(4) 0.0566(2) 0.0796(16) Uani 1 1 d . . . H7 H 0.3095 0.4619 0.0626 0.11(2) Uiso 1 1 calc R . . C8 C 0.2942(5) 0.6262(4) 0.0680(2) 0.0654(13) Uani 1 1 d . . . H8 H 0.2230 0.6266 0.0821 0.048(12) Uiso 1 1 calc R . . C9 C 0.3505(4) 0.7256(3) 0.05796(17) 0.0516(11) Uani 1 1 d . . . N10 N 0.3624(3) 0.9841(3) 0.00977(14) 0.0506(9) Uani 1 1 d . . . C11 C 0.4397(4) 0.9847(4) -0.03356(18) 0.0521(11) Uani 1 1 d . . . H11 H 0.4997 1.0377 -0.0264 0.050(11) Uiso 1 1 calc R . . C12 C 0.4858(4) 0.8684(4) -0.03197(18) 0.0514(11) Uani 1 1 d . . . H12A H 0.5583 0.8653 -0.0484 0.066(14) Uiso 1 1 calc R . . H12B H 0.4364 0.8169 -0.0494 0.076(15) Uiso 1 1 calc R . . C13 C 0.3830(4) 1.0166(4) -0.0835(2) 0.0599(12) Uani 1 1 d . . . O13 O 0.4207(3) 0.9847(3) -0.12511(13) 0.0739(10) Uani 1 1 d . . . N14 N 0.2924(3) 1.0800(3) -0.07855(17) 0.0640(11) Uani 1 1 d . . . H14 H 0.2560 1.0949 -0.1063 0.080(18) Uiso 1 1 calc R . . C15 C 0.2502(4) 1.1257(4) -0.0312(2) 0.0670(13) Uani 1 1 d . . . H15 H 0.1690 1.1296 -0.0344 0.12(2) Uiso 1 1 calc R . . C16 C 0.2756(4) 1.0523(4) 0.0144(2) 0.0589(12) Uani 1 1 d . . . O16 O 0.2193(3) 1.0579(3) 0.05419(16) 0.0746(10) Uani 1 1 d . . . C17 C 0.2930(6) 1.2466(4) -0.0204(3) 0.0854(18) Uani 1 1 d . . . H17A H 0.2798 1.2922 -0.0507 0.080(17) Uiso 1 1 calc R . . H17B H 0.2510 1.2781 0.0081 0.13(3) Uiso 1 1 calc R . . C18 C 0.4125(5) 1.2495(4) -0.0076(2) 0.0729(15) Uani 1 1 d . . . C19 C 0.4899(7) 1.2706(5) -0.0469(3) 0.098(2) Uani 1 1 d . . . H19 H 0.4660 1.2898 -0.0799 0.11(2) Uiso 1 1 calc R . . C20 C 0.6040(8) 1.2625(7) -0.0359(6) 0.129(3) Uani 1 1 d . . . H20 H 0.6556 1.2761 -0.0619 0.15(3) Uiso 1 1 calc R . . C21 C 0.6398(9) 1.2353(7) 0.0119(6) 0.137(4) Uani 1 1 d . . . H21 H 0.7155 1.2285 0.0187 0.15(3) Uiso 1 1 calc R . . C22 C 0.5626(9) 1.2177(5) 0.0508(4) 0.113(3) Uani 1 1 d . . . H22 H 0.5872 1.2006 0.0839 0.13(3) Uiso 1 1 calc R . . C23 C 0.4520(7) 1.2248(4) 0.0415(2) 0.0828(17) Uani 1 1 d . . . H23 H 0.4019 1.2130 0.0683 0.09(2) Uiso 1 1 calc R . . C24 C 0.5909(4) 0.7742(4) 0.13521(18) 0.0613(13) Uani 1 1 d . . . H24 H 0.5193 0.7462 0.1312 0.055(13) Uiso 1 1 calc R . . C25 C 0.6504(5) 0.7568(5) 0.18049(19) 0.0702(14) Uani 1 1 d . . . H25 H 0.6177 0.7168 0.2073 0.085(17) Uiso 1 1 calc R . . C26 C 0.7573(5) 0.7976(4) 0.1866(2) 0.0666(13) Uani 1 1 d . . . H26 H 0.7960 0.7837 0.2171 0.074(14) Uiso 1 1 calc R . . C27 C 0.8068(4) 0.8585(4) 0.14793(19) 0.0573(12) Uani 1 1 d . . . H27 H 0.8785 0.8859 0.1523 0.070(15) Uiso 1 1 calc R . . C28 C 0.7496(3) 0.8791(4) 0.10252(17) 0.0484(10) Uani 1 1 d . . . C29 C 0.6419(4) 0.8347(4) 0.09608(17) 0.0502(11) Uani 1 1 d . . . N30 N 0.6047(3) 0.8647(3) 0.04721(13) 0.0506(9) Uani 1 1 d . . . C31 C 0.6856(4) 0.9304(4) 0.02540(18) 0.0527(11) Uani 1 1 d . . . H31 H 0.6797 0.9632 -0.0070 0.043(11) Uiso 1 1 calc R . . C32 C 0.7750(4) 0.9414(4) 0.05680(18) 0.0537(11) Uani 1 1 d . . . C33 C 0.8816(4) 1.0021(4) 0.0449(2) 0.0624(13) Uani 1 1 d . . . H33A H 0.9162 1.0249 0.0771 0.052(12) Uiso 1 1 calc R . . H33B H 0.8644 1.0688 0.0254 0.048(11) Uiso 1 1 calc R . . C34 C 0.9649(4) 0.9302(4) 0.0138(2) 0.0681(14) Uani 1 1 d . . . H34 H 1.0313 0.9757 0.0075 0.075(14) Uiso 1 1 calc R . . N35 N 0.9197(3) 0.8990(4) -0.03602(18) 0.0741(12) Uani 1 1 d . . . H35 H 0.9255 0.9464 -0.0608 0.086(19) Uiso 1 1 calc R . . C36 C 0.8704(5) 0.8037(6) -0.0464(2) 0.0804(16) Uani 1 1 d . . . O36 O 0.8148(5) 0.7915(4) -0.08612(19) 0.1191(16) Uani 1 1 d . . . C37 C 0.8809(5) 0.7097(4) -0.0084(2) 0.0711(14) Uani 1 1 d . . . H37 H 0.8074 0.6945 0.0064 0.077(16) Uiso 1 1 calc R . . N38 N 0.9581(3) 0.7332(4) 0.03361(17) 0.0643(10) Uani 1 1 d . . . H38 H 0.9784 0.6781 0.0526 0.079(18) Uiso 1 1 calc R . . C39 C 0.9999(4) 0.8322(4) 0.0451(2) 0.0597(12) Uani 1 1 d . . . O39 O 1.0662(3) 0.8454(3) 0.08221(14) 0.0690(9) Uani 1 1 d . . . C40 C 0.9202(6) 0.6060(5) -0.0377(3) 0.0964(19) Uani 1 1 d . . . H40A H 0.8684 0.5918 -0.0657 0.10(2) Uiso 1 1 calc R . . H40B H 0.9920 0.6221 -0.0531 0.10(2) Uiso 1 1 calc R . . C41 C 0.9309(7) 0.5016(6) -0.0059(3) 0.104(2) Uani 1 1 d . . . H41 H 0.9906 0.5123 0.0194 0.11(2) Uiso 1 1 calc R . . C42 C 0.8220(9) 0.4725(10) 0.0236(5) 0.155(4) Uani 1 1 d . . . H42A H 0.8012 0.5340 0.0452 0.22(6) Uiso 1 1 calc R . . H42B H 0.8341 0.4078 0.0446 0.28(7) Uiso 1 1 calc R . . H42C H 0.7637 0.4579 -0.0008 0.30(9) Uiso 1 1 calc R . . C43 C 0.9630(18) 0.4058(9) -0.0415(6) 0.193(5) Uani 1 1 d . . . H43A H 1.0321 0.4227 -0.0583 0.11(3) Uiso 1 1 calc R . . H43B H 0.9060 0.3955 -0.0671 0.24(8) Uiso 1 1 calc R . . H43C H 0.9710 0.3389 -0.0216 0.24(6) Uiso 1 1 calc R . . O1W O 0.1026(5) 0.0209(7) 0.1585(2) 0.156(2) Uani 1 1 d . . . O2WA O -0.0186(10) 0.3176(9) 0.1312(5) 0.174(5) Uani 0.60 1 d P . . O2WB O 0.1794(12) 0.2264(12) 0.1218(6) 0.142(5) Uani 0.40 1 d P . . O3W O 0.6240(18) 0.387(2) 0.1590(11) 0.55(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.051(2) 0.049(2) 0.077(3) 0.0039(19) 0.019(2) 0.0002(18) C2 0.049(2) 0.047(2) 0.050(2) 0.000(2) 0.001(2) 0.002(2) C3 0.037(2) 0.048(2) 0.052(2) -0.0045(19) -0.0018(18) 0.0003(17) C4 0.052(3) 0.044(2) 0.051(2) 0.001(2) -0.004(2) -0.0013(19) C5 0.076(3) 0.052(3) 0.074(3) -0.008(2) 0.005(3) 0.005(3) C6 0.106(5) 0.043(3) 0.092(4) -0.008(3) 0.001(4) 0.011(3) C7 0.099(5) 0.053(3) 0.087(4) 0.000(3) 0.001(3) -0.016(3) C8 0.067(3) 0.059(3) 0.071(3) 0.005(2) 0.002(3) -0.015(3) C9 0.055(3) 0.044(3) 0.056(3) 0.001(2) 0.001(2) -0.007(2) N10 0.049(2) 0.043(2) 0.060(2) -0.0002(17) 0.0033(18) 0.0059(16) C11 0.047(3) 0.053(3) 0.056(3) 0.002(2) -0.006(2) -0.002(2) C12 0.046(3) 0.052(3) 0.056(3) -0.004(2) -0.002(2) 0.001(2) C13 0.065(3) 0.055(3) 0.059(3) 0.003(2) -0.014(3) -0.009(2) O13 0.078(2) 0.088(3) 0.055(2) 0.0099(19) -0.0015(18) -0.0007(19) N14 0.063(3) 0.054(2) 0.075(3) 0.002(2) -0.024(2) 0.002(2) C15 0.058(3) 0.049(3) 0.094(4) -0.002(3) -0.011(3) 0.003(2) C16 0.051(3) 0.041(3) 0.085(4) 0.000(2) 0.000(3) 0.000(2) O16 0.066(2) 0.060(2) 0.099(3) 0.0036(19) 0.015(2) 0.0098(16) C17 0.109(5) 0.049(3) 0.098(5) 0.002(3) -0.021(4) 0.008(3) C18 0.101(5) 0.038(3) 0.079(4) -0.011(2) -0.011(3) -0.012(3) C19 0.129(7) 0.070(4) 0.094(5) -0.011(3) -0.007(5) -0.033(4) C20 0.102(7) 0.094(6) 0.192(10) -0.025(6) 0.012(8) -0.041(5) C21 0.115(8) 0.075(5) 0.222(12) -0.008(6) -0.070(9) -0.023(4) C22 0.140(8) 0.065(4) 0.135(7) 0.004(4) -0.055(7) -0.028(4) C23 0.116(5) 0.059(3) 0.073(4) 0.000(3) -0.024(4) -0.014(3) C24 0.057(3) 0.074(3) 0.052(3) 0.007(2) -0.003(2) -0.004(3) C25 0.079(4) 0.080(4) 0.052(3) 0.017(3) -0.002(3) -0.004(3) C26 0.078(4) 0.067(3) 0.054(3) 0.004(2) -0.011(3) 0.004(3) C27 0.056(3) 0.052(3) 0.063(3) -0.007(2) -0.010(2) 0.002(2) C28 0.043(3) 0.044(2) 0.058(3) -0.001(2) -0.002(2) 0.004(2) C29 0.048(3) 0.054(3) 0.049(3) 0.001(2) 0.000(2) 0.000(2) N30 0.043(2) 0.058(2) 0.051(2) 0.0076(18) -0.0022(16) -0.0036(17) C31 0.046(3) 0.059(3) 0.053(3) 0.008(2) -0.005(2) -0.005(2) C32 0.045(3) 0.052(2) 0.065(3) 0.010(2) -0.003(2) 0.0006(19) C33 0.047(3) 0.057(3) 0.082(3) 0.011(3) -0.011(3) -0.012(2) C34 0.042(3) 0.073(3) 0.089(4) 0.022(3) 0.004(3) -0.010(2) N35 0.060(3) 0.095(4) 0.067(3) 0.022(3) 0.005(2) 0.005(2) C36 0.064(4) 0.106(5) 0.072(4) 0.010(3) -0.011(3) 0.004(3) O36 0.132(4) 0.130(4) 0.094(3) 0.013(3) -0.036(3) 0.005(3) C37 0.068(4) 0.072(4) 0.073(3) 0.008(3) -0.006(3) -0.011(3) N38 0.057(2) 0.066(3) 0.069(2) 0.014(2) -0.003(2) 0.000(2) C39 0.038(2) 0.071(3) 0.070(3) 0.019(3) 0.004(2) 0.000(2) O39 0.0489(19) 0.075(2) 0.083(2) 0.0145(18) -0.0043(19) -0.0050(16) C40 0.111(5) 0.083(4) 0.095(4) -0.001(4) -0.011(5) -0.013(4) C41 0.124(6) 0.079(4) 0.111(5) 0.003(4) -0.026(5) -0.016(4) C42 0.167(9) 0.118(8) 0.180(9) 0.042(8) -0.018(8) -0.053(7) C43 0.286(18) 0.087(7) 0.206(11) -0.035(8) 0.007(17) -0.003(8) O1W 0.122(4) 0.224(7) 0.122(4) -0.022(4) 0.031(4) -0.007(4) O2WA 0.202(11) 0.117(7) 0.202(11) -0.016(7) 0.063(9) -0.016(7) O2WB 0.134(11) 0.124(10) 0.169(13) -0.069(10) 0.029(10) -0.004(9) O3W 0.45(3) 0.66(4) 0.54(3) -0.41(3) 0.17(3) -0.16(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.369(6) . ? N1 C2 1.446(6) . ? C2 N10 1.449(5) . ? C2 C3 1.577(6) . ? C3 N30 1.456(5) . ? C3 C4 1.504(6) . ? C3 C12 1.558(6) . ? C4 C5 1.374(6) . ? C4 C9 1.384(6) . ? C5 C6 1.389(8) . ? C6 C7 1.369(8) . ? C7 C8 1.366(8) . ? C8 C9 1.398(6) . ? N10 C16 1.332(6) . ? N10 C11 1.456(6) . ? C11 C12 1.505(6) . ? C11 C13 1.512(7) . ? C13 O13 1.229(6) . ? C13 N14 1.335(7) . ? N14 C15 1.436(7) . ? C15 C16 1.504(8) . ? C15 C17 1.567(7) . ? C16 O16 1.235(6) . ? C17 C18 1.474(9) . ? C18 C23 1.388(8) . ? C18 C19 1.402(9) . ? C19 C20 1.403(12) . ? C20 C21 1.350(13) . ? C21 C22 1.385(14) . ? C22 C23 1.353(10) . ? C24 C25 1.388(7) . ? C24 C29 1.389(7) . ? C25 C26 1.385(7) . ? C26 C27 1.376(7) . ? C27 C28 1.384(7) . ? C28 C29 1.410(6) . ? C28 C32 1.433(6) . ? C29 N30 1.390(6) . ? N30 C31 1.374(5) . ? C31 C32 1.354(6) . ? C32 C33 1.506(6) . ? C33 C34 1.550(7) . ? C34 N35 1.449(7) . ? C34 C39 1.490(7) . ? N35 C36 1.318(8) . ? C36 O36 1.234(7) . ? C36 C37 1.503(8) . ? C37 N38 1.457(7) . ? C37 C40 1.534(9) . ? N38 C39 1.326(6) . ? C39 O39 1.257(6) . ? C40 C41 1.506(9) . ? C41 C43 1.524(13) . ? C41 C42 1.554(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 C9 N1 C2 111.4(3) . . ? N1 C2 N10 114.2(3) . . ? N1 C2 C3 104.6(3) . . ? N10 C2 C3 104.7(3) . . ? N30 C3 C4 114.4(3) . . ? N30 C3 C12 111.9(3) . . ? C4 C3 C12 110.8(3) . . ? N30 C3 C2 113.2(3) . . ? C4 C3 C2 102.8(3) . . ? C12 C3 C2 102.7(3) . . ? C5 C4 C9 121.4(4) . . ? C5 C4 C3 129.3(4) . . ? C9 C4 C3 109.2(4) . . ? C4 C5 C6 118.4(5) . . ? C7 C6 C5 120.0(5) . . ? C8 C7 C6 122.3(5) . . ? C7 C8 C9 118.1(5) . . ? N1 C9 C4 111.6(4) . . ? N1 C9 C8 128.6(4) . . ? C4 C9 C8 119.8(4) . . ? C16 N10 C2 122.8(4) . . ? C16 N10 C11 124.5(4) . . ? C2 N10 C11 112.1(3) . . ? N10 C11 C12 102.1(3) . . ? N10 C11 C13 111.9(4) . . ? C12 C11 C13 115.2(4) . . ? C11 C12 C3 105.0(4) . . ? O13 C13 N14 124.3(5) . . ? O13 C13 C11 120.2(5) . . ? N14 C13 C11 115.5(5) . . ? C13 N14 C15 126.1(4) . . ? N14 C15 C16 111.9(4) . . ? N14 C15 C17 113.0(5) . . ? C16 C15 C17 109.7(4) . . ? O16 C16 N10 122.6(5) . . ? O16 C16 C15 120.7(4) . . ? N10 C16 C15 116.7(5) . . ? C18 C17 C15 112.5(4) . . ? C23 C18 C19 118.3(7) . . ? C23 C18 C17 122.3(6) . . ? C19 C18 C17 119.2(6) . . ? C18 C19 C20 119.3(8) . . ? C21 C20 C19 120.9(10) . . ? C20 C21 C22 119.3(9) . . ? C23 C22 C21 121.2(8) . . ? C22 C23 C18 120.9(8) . . ? C25 C24 C29 117.8(5) . . ? C26 C25 C24 121.4(5) . . ? C27 C26 C25 120.4(5) . . ? C26 C27 C28 119.9(5) . . ? C27 C28 C29 119.3(4) . . ? C27 C28 C32 133.5(4) . . ? C29 C28 C32 107.2(4) . . ? C24 C29 N30 131.1(4) . . ? C24 C29 C28 121.1(4) . . ? N30 C29 C28 107.7(4) . . ? C31 N30 C29 107.2(3) . . ? C31 N30 C3 127.7(4) . . ? C29 N30 C3 124.9(3) . . ? C32 C31 N30 111.8(4) . . ? C31 C32 C28 106.0(4) . . ? C31 C32 C33 126.9(4) . . ? C28 C32 C33 127.1(4) . . ? C32 C33 C34 112.7(4) . . ? N35 C34 C39 112.7(5) . . ? N35 C34 C33 111.4(4) . . ? C39 C34 C33 109.9(4) . . ? C36 N35 C34 125.2(5) . . ? O36 C36 N35 121.1(6) . . ? O36 C36 C37 120.1(6) . . ? N35 C36 C37 118.8(5) . . ? N38 C37 C36 113.3(5) . . ? N38 C37 C40 109.3(5) . . ? C36 C37 C40 108.2(5) . . ? C39 N38 C37 125.7(4) . . ? O39 C39 N38 121.6(4) . . ? O39 C39 C34 119.7(5) . . ? N38 C39 C34 118.7(5) . . ? C41 C40 C37 115.7(6) . . ? C40 C41 C43 108.7(8) . . ? C40 C41 C42 112.6(7) . . ? C43 C41 C42 109.9(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 N10 114.8(4) . . . . ? C9 N1 C2 C3 0.9(5) . . . . ? N1 C2 C3 N30 -128.0(4) . . . . ? N10 C2 C3 N30 111.6(4) . . . . ? N1 C2 C3 C4 -4.0(4) . . . . ? N10 C2 C3 C4 -124.5(3) . . . . ? N1 C2 C3 C12 111.1(4) . . . . ? N10 C2 C3 C12 -9.4(4) . . . . ? N30 C3 C4 C5 -54.2(6) . . . . ? C12 C3 C4 C5 73.4(6) . . . . ? C2 C3 C4 C5 -177.4(5) . . . . ? N30 C3 C4 C9 129.1(4) . . . . ? C12 C3 C4 C9 -103.2(4) . . . . ? C2 C3 C4 C9 5.9(4) . . . . ? C9 C4 C5 C6 -0.9(7) . . . . ? C3 C4 C5 C6 -177.2(4) . . . . ? C4 C5 C6 C7 2.4(8) . . . . ? C5 C6 C7 C8 -2.5(9) . . . . ? C6 C7 C8 C9 1.0(8) . . . . ? C2 N1 C9 C4 3.0(5) . . . . ? C2 N1 C9 C8 -179.5(4) . . . . ? C5 C4 C9 N1 177.2(4) . . . . ? C3 C4 C9 N1 -5.8(5) . . . . ? C5 C4 C9 C8 -0.5(7) . . . . ? C3 C4 C9 C8 176.4(4) . . . . ? C7 C8 C9 N1 -176.9(5) . . . . ? C7 C8 C9 C4 0.5(7) . . . . ? N1 C2 N10 C16 60.6(5) . . . . ? C3 C2 N10 C16 174.4(4) . . . . ? N1 C2 N10 C11 -127.8(4) . . . . ? C3 C2 N10 C11 -14.0(4) . . . . ? C16 N10 C11 C12 -156.5(4) . . . . ? C2 N10 C11 C12 32.1(4) . . . . ? C16 N10 C11 C13 -32.8(6) . . . . ? C2 N10 C11 C13 155.8(4) . . . . ? N10 C11 C12 C3 -36.4(4) . . . . ? C13 C11 C12 C3 -157.9(4) . . . . ? N30 C3 C12 C11 -93.4(4) . . . . ? C4 C3 C12 C11 137.6(4) . . . . ? C2 C3 C12 C11 28.4(4) . . . . ? N10 C11 C13 O13 -154.0(4) . . . . ? C12 C11 C13 O13 -38.0(6) . . . . ? N10 C11 C13 N14 26.2(6) . . . . ? C12 C11 C13 N14 142.2(4) . . . . ? O13 C13 N14 C15 -175.2(5) . . . . ? C11 C13 N14 C15 4.6(7) . . . . ? C13 N14 C15 C16 -30.6(6) . . . . ? C13 N14 C15 C17 93.8(6) . . . . ? C2 N10 C16 O16 -1.2(7) . . . . ? C11 N10 C16 O16 -171.7(4) . . . . ? C2 N10 C16 C15 177.3(4) . . . . ? C11 N10 C16 C15 6.8(6) . . . . ? N14 C15 C16 O16 -157.4(4) . . . . ? C17 C15 C16 O16 76.3(6) . . . . ? N14 C15 C16 N10 24.0(6) . . . . ? C17 C15 C16 N10 -102.2(5) . . . . ? N14 C15 C17 C18 -69.8(6) . . . . ? C16 C15 C17 C18 55.8(7) . . . . ? C15 C17 C18 C23 -80.6(7) . . . . ? C15 C17 C18 C19 94.9(6) . . . . ? C23 C18 C19 C20 2.1(8) . . . . ? C17 C18 C19 C20 -173.7(6) . . . . ? C18 C19 C20 C21 -0.3(11) . . . . ? C19 C20 C21 C22 -1.5(12) . . . . ? C20 C21 C22 C23 1.5(11) . . . . ? C21 C22 C23 C18 0.4(9) . . . . ? C19 C18 C23 C22 -2.1(8) . . . . ? C17 C18 C23 C22 173.5(5) . . . . ? C29 C24 C25 C26 -0.4(8) . . . . ? C24 C25 C26 C27 1.1(8) . . . . ? C25 C26 C27 C28 -0.1(7) . . . . ? C26 C27 C28 C29 -1.5(7) . . . . ? C26 C27 C28 C32 177.3(5) . . . . ? C25 C24 C29 N30 179.6(5) . . . . ? C25 C24 C29 C28 -1.3(7) . . . . ? C27 C28 C29 C24 2.3(7) . . . . ? C32 C28 C29 C24 -176.8(4) . . . . ? C27 C28 C29 N30 -178.4(4) . . . . ? C32 C28 C29 N30 2.4(5) . . . . ? C24 C29 N30 C31 176.4(5) . . . . ? C28 C29 N30 C31 -2.8(5) . . . . ? C24 C29 N30 C3 2.2(7) . . . . ? C28 C29 N30 C3 -176.9(4) . . . . ? C4 C3 N30 C31 142.9(4) . . . . ? C12 C3 N30 C31 15.9(6) . . . . ? C2 C3 N30 C31 -99.7(5) . . . . ? C4 C3 N30 C29 -44.1(5) . . . . ? C12 C3 N30 C29 -171.2(4) . . . . ? C2 C3 N30 C29 73.3(5) . . . . ? C29 N30 C31 C32 2.1(5) . . . . ? C3 N30 C31 C32 176.1(4) . . . . ? N30 C31 C32 C28 -0.6(5) . . . . ? N30 C31 C32 C33 176.8(4) . . . . ? C27 C28 C32 C31 179.9(5) . . . . ? C29 C28 C32 C31 -1.2(5) . . . . ? C27 C28 C32 C33 2.5(8) . . . . ? C29 C28 C32 C33 -178.5(4) . . . . ? C31 C32 C33 C34 -83.4(6) . . . . ? C28 C32 C33 C34 93.4(6) . . . . ? C32 C33 C34 N35 61.9(5) . . . . ? C32 C33 C34 C39 -63.6(5) . . . . ? C39 C34 N35 C36 27.2(7) . . . . ? C33 C34 N35 C36 -96.8(6) . . . . ? C34 N35 C36 O36 165.4(5) . . . . ? C34 N35 C36 C37 -13.5(8) . . . . ? O36 C36 C37 N38 174.0(5) . . . . ? N35 C36 C37 N38 -7.1(8) . . . . ? O36 C36 C37 C40 52.6(7) . . . . ? N35 C36 C37 C40 -128.5(6) . . . . ? C36 C37 N38 C39 13.1(7) . . . . ? C40 C37 N38 C39 133.9(5) . . . . ? C37 N38 C39 O39 179.9(5) . . . . ? C37 N38 C39 C34 1.2(7) . . . . ? N35 C34 C39 O39 161.2(4) . . . . ? C33 C34 C39 O39 -74.0(5) . . . . ? N35 C34 C39 N38 -20.1(6) . . . . ? C33 C34 C39 N38 104.7(5) . . . . ? N38 C37 C40 C41 58.6(7) . . . . ? C36 C37 C40 C41 -177.5(6) . . . . ? C37 C40 C41 C43 176.3(10) . . . . ? C37 C40 C41 C42 54.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.572 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.053