# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email aicpg@iacs.res.in _publ_contact_author_name 'Pradyut Ghosh' _publ_author_name 'Pradyut Ghosh' data_test3 _database_code_depnum_ccdc_archive 'CCDC 861094' #TrackingRef 'PF_HPO4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C86 H109 F30 N16 O10 P' _chemical_formula_weight 2127.86 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 19.210(4) _cell_length_b 20.782(4) _cell_length_c 25.120(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10029(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4408 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28347 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 21.05 _reflns_number_total 10636 _reflns_number_gt 8855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'MERCURY 2.2' _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^)+(0.0000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00000(11) _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 0.18(16) _refine_ls_number_reflns 10636 _refine_ls_number_parameters 1289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.482 _refine_ls_restrained_S_all 1.482 _refine_ls_shift/su_max 3.785 _refine_ls_shift/su_mean 0.004 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 0.3714(3) 0.4859(3) 0.8102(2) 0.0511(17) Uani 1 1 d . . . H1A H 0.3331 0.4885 0.7852 0.061 Uiso 1 1 calc R . . H1B H 0.4092 0.4631 0.7930 0.061 Uiso 1 1 calc R . . C2 C 0.3954(3) 0.5535(3) 0.8236(2) 0.0416(15) Uani 1 1 d . . . H2A H 0.4030 0.5771 0.7908 0.050 Uiso 1 1 calc R . . H2B H 0.3590 0.5753 0.8434 0.050 Uiso 1 1 calc R . . C3 C 0.5217(3) 0.5491(3) 0.8320(3) 0.0400(15) Uani 1 1 d . . . C4 C 0.6405(3) 0.5265(3) 0.8583(2) 0.0423(16) Uani 1 1 d . . . C5 C 0.6498(3) 0.4658(4) 0.8377(3) 0.0514(18) Uani 1 1 d . . . C6 C 0.7138(4) 0.4386(4) 0.8284(3) 0.0616(19) Uani 1 1 d . . . C7 C 0.7722(4) 0.4723(4) 0.8408(3) 0.0561(19) Uani 1 1 d . . . C8 C 0.7669(3) 0.5325(4) 0.8627(3) 0.068(2) Uani 1 1 d . . . C9 C 0.7016(3) 0.5585(3) 0.8708(3) 0.0603(19) Uani 1 1 d . . . C10 C 0.3568(3) 0.3797(3) 0.8481(3) 0.0575(19) Uani 1 1 d . . . H10A H 0.3460 0.3698 0.8113 0.069 Uiso 1 1 calc R . . H10B H 0.3244 0.3563 0.8705 0.069 Uiso 1 1 calc R . . C11 C 0.4310(3) 0.3582(3) 0.8606(2) 0.0495(17) Uani 1 1 d . . . H11A H 0.4362 0.3128 0.8525 0.059 Uiso 1 1 calc R . . H11B H 0.4636 0.3820 0.8386 0.059 Uiso 1 1 calc R . . C12 C 0.4402(3) 0.3189(3) 0.9512(3) 0.0415(16) Uani 1 1 d . . . C13 C 0.4249(3) 0.2980(3) 1.0471(3) 0.0390(15) Uani 1 1 d . . . C14 C 0.3676(3) 0.2608(3) 1.0500(3) 0.0531(17) Uani 1 1 d . . . C15 C 0.3535(3) 0.2224(3) 1.0947(3) 0.0605(19) Uani 1 1 d . . . C16 C 0.3974(5) 0.2270(4) 1.1369(3) 0.072(2) Uani 1 1 d . . . C17 C 0.4542(4) 0.2644(4) 1.1369(3) 0.070(2) Uani 1 1 d . . . C18 C 0.4683(4) 0.3004(3) 1.0905(3) 0.0552(18) Uani 1 1 d . . . C19 C 0.2789(3) 0.4663(3) 0.8765(3) 0.0507(17) Uani 1 1 d . . . H19A H 0.2455 0.4346 0.8642 0.061 Uiso 1 1 calc R . . H19B H 0.2657 0.5077 0.8619 0.061 Uiso 1 1 calc R . . C20 C 0.2765(3) 0.4697(3) 0.9366(3) 0.0489(17) Uani 1 1 d . . . H20A H 0.2293 0.4796 0.9477 0.059 Uiso 1 1 calc R . . H20B H 0.2884 0.4278 0.9511 0.059 Uiso 1 1 calc R . . C21 C 0.3108(3) 0.5805(3) 0.9515(2) 0.0439(16) Uani 1 1 d . . . C22 C 0.3643(3) 0.6857(3) 0.9671(3) 0.0375(15) Uani 1 1 d . . . C23 C 0.3454(3) 0.7220(3) 0.9237(2) 0.0374(15) Uani 1 1 d . . . C24 C 0.3471(3) 0.7870(3) 0.9248(3) 0.0459(17) Uani 1 1 d . . . C25 C 0.3698(3) 0.8192(3) 0.9692(3) 0.0519(17) Uani 1 1 d . . . C26 C 0.3884(3) 0.7836(4) 1.0129(3) 0.0527(17) Uani 1 1 d . . . C27 C 0.3859(3) 0.7195(3) 1.0115(3) 0.0451(16) Uani 1 1 d . . . C28 C 0.7287(3) 0.5358(3) 0.1505(2) 0.0451(16) Uani 1 1 d . . . H28A H 0.7365 0.4917 0.1617 0.054 Uiso 1 1 calc R . . H28B H 0.7598 0.5633 0.1706 0.054 Uiso 1 1 calc R . . C29 C 0.7448(3) 0.5419(3) 0.0919(2) 0.0461(16) Uani 1 1 d . . . H29A H 0.7357 0.5857 0.0805 0.055 Uiso 1 1 calc R . . H29B H 0.7938 0.5331 0.0861 0.055 Uiso 1 1 calc R . . C30 C 0.7185(3) 0.4353(3) 0.0575(2) 0.0395(15) Uani 1 1 d . . . C31 C 0.6699(3) 0.3328(3) 0.0254(3) 0.0448(16) Uani 1 1 d . . . C32 C 0.6798(3) 0.2920(3) 0.0676(3) 0.0502(17) Uani 1 1 d . . . C33 C 0.6784(3) 0.2266(4) 0.0602(3) 0.0598(19) Uani 1 1 d . . . C34 C 0.6652(3) 0.2001(3) 0.0120(4) 0.066(2) Uani 1 1 d . . . C35 C 0.6531(3) 0.2393(4) -0.0298(3) 0.063(2) Uani 1 1 d . . . C36 C 0.6560(3) 0.3038(3) -0.0240(3) 0.0504(17) Uani 1 1 d . . . C37 C 0.6269(3) 0.5142(3) 0.2038(2) 0.0470(17) Uani 1 1 d . . . H37A H 0.5897 0.5380 0.2210 0.056 Uiso 1 1 calc R . . H37B H 0.6622 0.5053 0.2304 0.056 Uiso 1 1 calc R . . C38 C 0.5989(3) 0.4525(3) 0.1832(2) 0.0421(16) Uani 1 1 d . . . H38A H 0.6354 0.4298 0.1643 0.051 Uiso 1 1 calc R . . H38B H 0.5843 0.4259 0.2129 0.051 Uiso 1 1 calc R . . C39 C 0.4735(3) 0.4635(3) 0.1642(3) 0.0372(15) Uani 1 1 d . . . C40 C 0.3550(3) 0.4850(3) 0.1379(2) 0.0321(14) Uani 1 1 d . . . C41 C 0.3357(3) 0.5333(3) 0.1730(2) 0.0399(15) Uani 1 1 d . . . C42 C 0.2686(3) 0.5423(3) 0.1879(2) 0.0401(15) Uani 1 1 d . . . C43 C 0.2174(3) 0.5061(3) 0.1659(2) 0.0377(15) Uani 1 1 d . . . C44 C 0.2344(3) 0.4592(3) 0.1301(2) 0.0410(15) Uani 1 1 d . . . C45 C 0.3027(3) 0.4494(3) 0.1158(2) 0.0368(15) Uani 1 1 d . . . C46 C 0.6472(3) 0.6223(3) 0.1698(2) 0.0464(16) Uani 1 1 d . . . H46A H 0.6829 0.6457 0.1506 0.056 Uiso 1 1 calc R . . H46B H 0.6522 0.6321 0.2074 0.056 Uiso 1 1 calc R . . C47 C 0.5758(3) 0.6448(3) 0.1509(2) 0.0450(16) Uani 1 1 d . . . H47A H 0.5399 0.6194 0.1682 0.054 Uiso 1 1 calc R . . H47B H 0.5690 0.6895 0.1608 0.054 Uiso 1 1 calc R . . C48 C 0.5822(3) 0.6885(3) 0.0611(3) 0.0416(16) Uani 1 1 d . . . C49 C 0.6041(3) 0.7136(3) -0.0331(2) 0.0335(14) Uani 1 1 d . . . C50 C 0.6675(3) 0.7440(3) -0.0302(3) 0.0444(16) Uani 1 1 d . . . C51 C 0.6911(3) 0.7824(3) -0.0713(3) 0.0592(19) Uani 1 1 d . . . C52 C 0.6533(3) 0.7919(3) -0.1146(3) 0.0540(18) Uani 1 1 d . . . C53 C 0.5910(3) 0.7606(3) -0.1202(3) 0.0508(17) Uani 1 1 d . . . C54 C 0.5665(3) 0.7229(3) -0.0784(3) 0.0433(16) Uani 1 1 d . . . C55 C 0.1092(3) 0.8901(3) 0.3254(3) 0.0462(17) Uani 1 1 d . . . H55A H 0.138(3) 0.929(3) 0.337(2) 0.055 Uiso 1 1 d . . . H55B H 0.095(3) 0.900(3) 0.289(2) 0.055 Uiso 1 1 d . . . C56 C 0.1427(3) 0.8260(3) 0.3245(3) 0.0568(18) Uani 1 1 d . . . H56A H 0.1080 0.7945 0.3140 0.068 Uiso 1 1 calc R . . H56B H 0.1574 0.8156 0.3604 0.068 Uiso 1 1 calc R . . C57 C 0.2078(5) 0.8187(7) 0.2862(3) 0.138(5) Uani 1 1 d . . . H57A H 0.2417 0.8519 0.2942 0.166 Uiso 1 1 calc R . . H57B H 0.2296 0.7772 0.2920 0.166 Uiso 1 1 calc R . . C58 C 0.1891(7) 0.8233(8) 0.2391(7) 0.238(8) Uani 1 1 d . . . H58A H 0.1480 0.7979 0.2336 0.356 Uiso 1 1 calc R . . H58C H 0.2257 0.8081 0.2163 0.356 Uiso 1 1 calc R . . H58B H 0.1793 0.8676 0.2310 0.356 Uiso 1 1 calc R . . C59 C -0.0066 0.8430 0.3504 0.042 Uani 1 1 d . . . H59A H 0.0137 0.8031 0.3630 0.050 Uiso 1 1 calc R . . H59B H -0.0472 0.8517 0.3722 0.050 Uiso 1 1 calc R . . C60 C -0.0301(3) 0.8334(3) 0.2946(2) 0.0509(17) Uani 1 1 d . . . H60A H 0.0104 0.8300 0.2717 0.061 Uiso 1 1 calc R . . H60B H -0.0567 0.8706 0.2834 0.061 Uiso 1 1 calc R . . C61 C -0.0749(3) 0.7729(3) 0.2881(3) 0.0602(19) Uani 1 1 d . . . H61A H -0.0470 0.7357 0.2977 0.072 Uiso 1 1 calc R . . H61B H -0.1133 0.7753 0.3131 0.072 Uiso 1 1 calc R . . C62 C -0.1034(3) 0.7628(4) 0.2342(3) 0.079(2) Uani 1 1 d . . . H62A H -0.1370 0.7956 0.2265 0.119 Uiso 1 1 calc R . . H62B H -0.1253 0.7213 0.2325 0.119 Uiso 1 1 calc R . . H62C H -0.0663 0.7648 0.2086 0.119 Uiso 1 1 calc R . . C63 C 0.0116(3) 0.9615(3) 0.3484(2) 0.0482(16) Uani 1 1 d . . . H63A H 0.0011 0.9638 0.3107 0.058 Uiso 1 1 calc R . . H63B H -0.0324 0.9627 0.3673 0.058 Uiso 1 1 calc R . . C64 C 0.0518(4) 1.0197(3) 0.3630(3) 0.067(2) Uani 1 1 d . . . H64A H 0.0974 1.0171 0.3466 0.081 Uiso 1 1 calc R . . H64B H 0.0585 1.0200 0.4013 0.081 Uiso 1 1 calc R . . C65 C 0.0183(4) 1.0824(3) 0.3468(3) 0.0602(19) Uani 1 1 d . . . H65A H -0.0309 1.0808 0.3556 0.072 Uiso 1 1 calc R . . H65B H 0.0390 1.1171 0.3672 0.072 Uiso 1 1 calc R . . C66 C 0.0257(5) 1.0964(4) 0.2907(3) 0.116(3) Uani 1 1 d . . . H66A H 0.0020 1.1359 0.2825 0.174 Uiso 1 1 calc R . . H66B H 0.0059 1.0620 0.2702 0.174 Uiso 1 1 calc R . . H66C H 0.0742 1.1007 0.2821 0.174 Uiso 1 1 calc R . . C67 C 0.0683(3) 0.8930(3) 0.4183(2) 0.0466(16) Uani 1 1 d . . . H67A H 0.0869 0.8504 0.4247 0.056 Uiso 1 1 calc R . . H67B H 0.1059 0.9234 0.4236 0.056 Uiso 1 1 calc R . . C68 C 0.0135(3) 0.9060(3) 0.4592(2) 0.0591(18) Uani 1 1 d . . . H68A H -0.0253 0.8768 0.4539 0.071 Uiso 1 1 calc R . . H68B H -0.0036 0.9496 0.4551 0.071 Uiso 1 1 calc R . . C69 C 0.0422(4) 0.8975(3) 0.5145(2) 0.068(2) Uani 1 1 d . . . H69A H 0.0040 0.9016 0.5396 0.082 Uiso 1 1 calc R . . H69B H 0.0602 0.8540 0.5176 0.082 Uiso 1 1 calc R . . C70 C 0.0984(4) 0.9433(4) 0.5307(3) 0.091(3) Uani 1 1 d . . . H70A H 0.1413 0.9310 0.5140 0.137 Uiso 1 1 calc R . . H70B H 0.1039 0.9421 0.5687 0.137 Uiso 1 1 calc R . . H70C H 0.0860 0.9861 0.5198 0.137 Uiso 1 1 calc R . . C71 C 0.5444(3) 0.8953(3) 0.0894(2) 0.0391(15) Uani 1 1 d . . . H71A H 0.5441 0.8499 0.0803 0.047 Uiso 1 1 calc R . . H71B H 0.4977 0.9115 0.0834 0.047 Uiso 1 1 calc R . . C72 C 0.5918(3) 0.9286(3) 0.0519(2) 0.0450(16) Uani 1 1 d . . . H72A H 0.6396 0.9178 0.0608 0.054 Uiso 1 1 calc R . . H72B H 0.5864 0.9747 0.0560 0.054 Uiso 1 1 calc R . . C73 C 0.5776(3) 0.9101(3) -0.0063(2) 0.0509(17) Uani 1 1 d . . . H73A H 0.5823 0.8639 -0.0105 0.061 Uiso 1 1 calc R . . H73B H 0.5302 0.9218 -0.0156 0.061 Uiso 1 1 calc R . . C74 C 0.6277(3) 0.9440(3) -0.0431(2) 0.0590(18) Uani 1 1 d . . . H74A H 0.6208 0.9896 -0.0406 0.088 Uiso 1 1 calc R . . H74B H 0.6196 0.9302 -0.0790 0.088 Uiso 1 1 calc R . . H74C H 0.6746 0.9336 -0.0330 0.088 Uiso 1 1 calc R . . C75 C 0.5754(3) 0.9711(3) 0.1634(2) 0.0483(17) Uani 1 1 d . . . H75A H 0.5864 0.9723 0.2011 0.058 Uiso 1 1 calc R . . H75B H 0.6165 0.9851 0.1442 0.058 Uiso 1 1 calc R . . C76 C 0.5182(3) 1.0183(3) 0.1529(3) 0.0585(18) Uani 1 1 d . . . H76A H 0.4774 1.0043 0.1724 0.070 Uiso 1 1 calc R . . H76B H 0.5069 1.0163 0.1154 0.070 Uiso 1 1 calc R . . C77 C 0.5317(7) 1.0873(6) 0.1670(7) 0.218(8) Uani 1 1 d . . . H77A H 0.5049 1.1122 0.1415 0.261 Uiso 1 1 calc R . . H77B H 0.5092 1.0937 0.2011 0.261 Uiso 1 1 calc R . . C78 C 0.5801(6) 1.1113(6) 0.1700(7) 0.194(7) Uani 1 1 d . . . H78A H 0.6044 1.0964 0.2011 0.291 Uiso 1 1 calc R . . H78B H 0.5723 1.1568 0.1728 0.291 Uiso 1 1 calc R . . H78C H 0.6075 1.1025 0.1389 0.291 Uiso 1 1 calc R . . C79 C 0.6245(3) 0.8614(3) 0.1595(2) 0.0437(16) Uani 1 1 d . . . H79A H 0.6620 0.8765 0.1370 0.052 Uiso 1 1 calc R . . H79B H 0.6150 0.8171 0.1498 0.052 Uiso 1 1 calc R . . C80 C 0.6491(3) 0.8629(3) 0.2171(2) 0.0514(17) Uani 1 1 d . . . H80A H 0.6719 0.9036 0.2241 0.062 Uiso 1 1 calc R . . H80B H 0.6092 0.8596 0.2406 0.062 Uiso 1 1 calc R . . C81 C 0.6989(3) 0.8087(4) 0.2287(2) 0.063(2) Uani 1 1 d . . . H81A H 0.7365 0.8095 0.2029 0.075 Uiso 1 1 calc R . . H81B H 0.6747 0.7680 0.2250 0.075 Uiso 1 1 calc R . . C82 C 0.7296(3) 0.8138(4) 0.2854(2) 0.071(2) Uani 1 1 d . . . H82A H 0.7584 0.8514 0.2878 0.106 Uiso 1 1 calc R . . H82B H 0.7570 0.7763 0.2929 0.106 Uiso 1 1 calc R . . H82C H 0.6923 0.8169 0.3108 0.106 Uiso 1 1 calc R . . C83 C 0.4979(2) 0.8792(3) 0.1801(2) 0.0364(14) Uani 1 1 d . . . H83A H 0.5044 0.8929 0.2166 0.044 Uiso 1 1 calc R . . H83B H 0.4570 0.9011 0.1665 0.044 Uiso 1 1 calc R . . C84 C 0.4836(3) 0.8077(2) 0.1800(2) 0.0418(15) Uani 1 1 d . . . H84A H 0.5179 0.7860 0.2019 0.050 Uiso 1 1 calc R . . H84B H 0.4876 0.7913 0.1440 0.050 Uiso 1 1 calc R . . C85 C 0.4107(3) 0.7935(3) 0.2014(3) 0.0600(19) Uani 1 1 d . . . H85A H 0.4071 0.8099 0.2374 0.072 Uiso 1 1 calc R . . H85B H 0.3767 0.8160 0.1797 0.072 Uiso 1 1 calc R . . C86 C 0.3939(4) 0.72262(17) 0.20152(12) 0.102(3) Uani 1 1 d . . . H86A H 0.4112 0.7032 0.1695 0.153 Uiso 1 1 calc R . . H86B H 0.3443 0.7169 0.2034 0.153 Uiso 1 1 calc R . . H86C H 0.4153 0.7026 0.2318 0.153 Uiso 1 1 calc R . . N1 N 0.34865(16) 0.44885(14) 0.85720(12) 0.0452(13) Uani 1 1 d R . . N2 N 0.45822(16) 0.55399(14) 0.85426(12) 0.0387(12) Uani 1 1 d R . . H2 H 0.4553 0.5576 0.8883 0.046 Uiso 1 1 calc R . . N3 N 0.5761(2) 0.5532(2) 0.86838(19) 0.0479(14) Uani 1 1 d . . . H3 H 0.5694 0.5731 0.8980 0.057 Uiso 1 1 calc R . . N4 N 0.4463(2) 0.3692(2) 0.91581(19) 0.0422(12) Uani 1 1 d . . . H4 H 0.4590 0.4067 0.9266 0.051 Uiso 1 1 calc R . . N5 N 0.4371(2) 0.3388(2) 1.0037(2) 0.0479(13) Uani 1 1 d . . . H5 H 0.4432 0.3791 1.0101 0.057 Uiso 1 1 calc R . . N6 N 0.3224(2) 0.5164(2) 0.95817(19) 0.0431(13) Uani 1 1 d . . . H6 H 0.3583 0.5040 0.9758 0.052 Uiso 1 1 calc R . . N7 N 0.3654(2) 0.6185(2) 0.96669(18) 0.0407(13) Uani 1 1 d . . . H7 H 0.4031 0.5998 0.9767 0.049 Uiso 1 1 calc R . . N8 N 0.6570(2) 0.5537(2) 0.16167(17) 0.0374(12) Uani 1 1 d . . . N9 N 0.7033(2) 0.4978(2) 0.05986(17) 0.0402(12) Uani 1 1 d . . . H9 H 0.6684 0.5124 0.0422 0.048 Uiso 1 1 calc R . . N10 N 0.6687(2) 0.3998(2) 0.03013(19) 0.0458(13) Uani 1 1 d . . . H10 H 0.6351 0.4204 0.0152 0.055 Uiso 1 1 calc R . . N11 N 0.5394(2) 0.4625(2) 0.14714(17) 0.0380(12) Uani 1 1 d . . . H11 H 0.5474 0.4680 0.1138 0.046 Uiso 1 1 calc R . . N12 N 0.4245(2) 0.4748(2) 0.12472(18) 0.0404(13) Uani 1 1 d . . . H12 H 0.4372 0.4755 0.0919 0.049 Uiso 1 1 calc R . . N13 N 0.5696(2) 0.6380(2) 0.09310(18) 0.0444(13) Uani 1 1 d . . . H13 H 0.5580 0.6016 0.0796 0.053 Uiso 1 1 calc R . . N14 N 0.5799(2) 0.6717(2) 0.00654(18) 0.0399(12) Uani 1 1 d . . . H14 H 0.5634 0.6348 -0.0025 0.048 Uiso 1 1 calc R . . N15 N 0.0458(2) 0.8967(2) 0.35932(17) 0.0311(11) Uani 1 1 d . . . N16 N 0.5602(2) 0.9011(2) 0.14799(16) 0.0291(11) Uani 1 1 d . . . O2 O 0.44722(16) 0.47017(16) 1.01069(14) 0.0375(9) Uani 1 1 d . . . O3 O 0.56107(17) 0.51535(16) 1.04598(14) 0.0390(10) Uani 1 1 d . . . O4 O 0.50296(16) 0.56442(15) 0.96589(13) 0.0336(9) Uani 1 1 d . . . O5 O 0.5323(2) 0.54142(19) 0.78436(16) 0.0508(11) Uani 1 1 d . . . O6 O 0.4403(2) 0.2628(2) 0.93886(15) 0.0535(11) Uani 1 1 d . . . O7 O 0.25573(19) 0.60193(18) 0.93501(17) 0.0528(12) Uani 1 1 d . . . O8 O 0.7710(2) 0.41054(19) 0.07630(17) 0.0518(11) Uani 1 1 d . . . O9 O 0.45690(19) 0.45526(19) 0.21053(15) 0.0472(11) Uani 1 1 d . . . O10 O 0.5945(2) 0.7435(2) 0.07453(16) 0.0568(12) Uani 1 1 d . . . F1 F 0.59378(19) 0.42846(17) 0.82916(15) 0.0702(11) Uani 1 1 d . . . F2 F 0.7204(2) 0.3788(2) 0.80871(18) 0.1001(15) Uani 1 1 d . . . F3 F 0.83647(19) 0.4477(2) 0.83328(15) 0.0867(13) Uani 1 1 d . . . F4 F 0.82368(19) 0.5670(2) 0.8770(2) 0.1080(17) Uani 1 1 d . . . F5 F 0.69718(18) 0.6188(2) 0.8910(2) 0.1039(16) Uani 1 1 d . . . F6 F 0.32162(18) 0.25685(18) 1.00972(16) 0.0734(11) Uani 1 1 d . . . F7 F 0.2967(2) 0.1858(2) 1.09653(18) 0.0989(15) Uani 1 1 d . . . F8 F 0.3810(3) 0.1932(2) 1.18190(17) 0.1107(16) Uani 1 1 d . . . F9 F 0.4960(3) 0.2691(2) 1.17828(18) 0.1126(16) Uani 1 1 d . . . F10 F 0.5251(2) 0.33683(19) 1.08901(16) 0.0819(12) Uani 1 1 d . . . F11 F 0.32815(15) 0.69342(15) 0.87755(13) 0.0484(9) Uani 1 1 d . . . F12 F 0.32922(17) 0.82166(16) 0.88105(15) 0.0619(10) Uani 1 1 d . . . F13 F 0.37256(18) 0.88452(18) 0.97075(17) 0.0773(12) Uani 1 1 d . . . F14 F 0.40990(19) 0.81479(18) 1.05789(16) 0.0813(13) Uani 1 1 d . . . F15 F 0.40611(18) 0.68493(17) 1.05493(14) 0.0656(11) Uani 1 1 d . . . F16 F 0.68692(17) 0.31464(17) 0.11710(15) 0.0622(10) Uani 1 1 d . . . F17 F 0.6912(2) 0.18774(19) 0.10331(17) 0.0873(13) Uani 1 1 d . . . F18 F 0.6638(2) 0.13531(19) 0.0067(2) 0.0990(15) Uani 1 1 d . . . F19 F 0.6420(2) 0.21368(19) -0.07856(18) 0.0902(14) Uani 1 1 d . . . F20 F 0.64618(18) 0.34203(17) -0.06648(15) 0.0668(11) Uani 1 1 d . . . F21 F 0.38462(16) 0.57172(16) 0.19418(14) 0.0588(10) Uani 1 1 d . . . F22 F 0.25226(17) 0.58831(17) 0.22330(14) 0.0625(10) Uani 1 1 d . . . F23 F 0.14959(15) 0.51503(18) 0.17918(13) 0.0616(10) Uani 1 1 d . . . F24 F 0.18332(16) 0.42222(17) 0.10868(14) 0.0637(11) Uani 1 1 d . . . F25 F 0.31725(16) 0.40254(17) 0.08160(14) 0.0628(10) Uani 1 1 d . . . F26 F 0.71066(17) 0.73181(18) 0.01058(15) 0.0680(11) Uani 1 1 d . . . F27 F 0.75373(19) 0.8119(2) -0.06690(17) 0.0903(13) Uani 1 1 d . . . F28 F 0.6756(2) 0.8298(2) -0.15469(16) 0.0839(12) Uani 1 1 d . . . F29 F 0.55148(18) 0.76789(18) -0.16363(16) 0.0742(11) Uani 1 1 d . . . F30 F 0.50390(15) 0.69445(16) -0.08457(13) 0.0546(9) Uani 1 1 d . . . P1 P 0.51435(7) 0.50382(7) 0.99853(6) 0.0313(4) Uani 1 1 d . . . O1 O 0.56142(16) 0.45513(18) 0.96247(15) 0.0423(10) Uani 1 1 d . . . H1 H 0.5359 0.4332 0.9436 0.063 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 0.053(4) 0.058(5) 0.042(4) -0.001(4) -0.019(3) 0.002(3) C2 0.051(4) 0.040(4) 0.034(4) 0.012(3) -0.002(3) -0.005(3) C3 0.056(4) 0.036(4) 0.028(4) 0.005(3) 0.002(4) 0.004(3) C4 0.054(4) 0.043(5) 0.029(4) 0.000(3) 0.012(3) 0.001(4) C5 0.044(4) 0.064(5) 0.047(4) 0.015(4) -0.012(4) 0.000(4) C6 0.085(6) 0.049(5) 0.050(5) 0.002(4) -0.021(4) 0.016(5) C7 0.066(5) 0.062(6) 0.040(4) 0.015(4) 0.023(4) 0.031(5) C8 0.033(4) 0.076(6) 0.095(6) 0.021(5) 0.012(4) -0.010(4) C9 0.059(5) 0.040(5) 0.082(5) -0.007(4) 0.017(4) -0.021(4) C10 0.061(4) 0.065(5) 0.047(4) -0.001(4) -0.008(4) -0.003(4) C11 0.065(4) 0.043(4) 0.040(4) -0.010(3) 0.003(4) 0.000(3) C12 0.043(4) 0.037(5) 0.045(5) -0.019(4) 0.008(3) 0.004(3) C13 0.044(4) 0.025(4) 0.048(4) -0.003(3) 0.017(4) -0.005(3) C14 0.060(5) 0.048(5) 0.051(5) 0.003(4) 0.000(4) 0.002(4) C15 0.051(4) 0.058(5) 0.073(6) 0.012(5) 0.018(4) -0.011(4) C16 0.102(7) 0.058(6) 0.056(6) 0.014(4) 0.023(5) 0.004(5) C17 0.089(6) 0.068(6) 0.053(5) -0.013(5) -0.008(5) -0.010(5) C18 0.062(5) 0.048(5) 0.055(5) -0.004(4) 0.003(4) -0.007(4) C19 0.032(3) 0.051(4) 0.069(5) 0.006(4) -0.014(3) -0.006(3) C20 0.038(4) 0.041(4) 0.067(5) 0.012(4) 0.014(3) 0.013(3) C21 0.038(4) 0.044(5) 0.050(4) 0.009(3) 0.014(4) 0.017(4) C22 0.031(3) 0.031(4) 0.051(4) -0.004(4) -0.001(3) 0.019(3) C23 0.028(3) 0.045(5) 0.039(4) 0.001(4) -0.001(3) 0.005(3) C24 0.036(3) 0.040(5) 0.063(5) 0.011(4) -0.003(4) 0.015(3) C25 0.057(4) 0.025(4) 0.074(5) -0.002(4) -0.010(4) 0.004(3) C26 0.048(4) 0.047(5) 0.063(5) -0.010(5) -0.008(4) 0.015(3) C27 0.041(4) 0.045(5) 0.049(5) 0.001(4) -0.009(3) 0.017(3) C28 0.042(4) 0.045(4) 0.048(4) 0.001(3) -0.016(3) -0.007(3) C29 0.035(3) 0.049(4) 0.055(5) 0.001(4) 0.002(3) -0.009(3) C30 0.045(4) 0.037(5) 0.037(4) 0.002(3) -0.001(3) -0.001(3) C31 0.041(4) 0.040(5) 0.054(5) -0.002(4) -0.020(3) 0.016(3) C32 0.053(4) 0.031(5) 0.067(5) -0.004(4) -0.023(4) 0.003(3) C33 0.057(4) 0.050(6) 0.072(6) 0.018(5) -0.025(4) 0.010(4) C34 0.070(5) 0.034(5) 0.095(7) -0.010(5) -0.034(5) 0.012(4) C35 0.065(5) 0.051(6) 0.073(6) -0.017(5) -0.032(4) 0.016(4) C36 0.061(4) 0.038(5) 0.053(5) -0.002(4) -0.020(4) 0.022(3) C37 0.046(4) 0.065(5) 0.030(4) 0.008(3) -0.005(3) -0.006(3) C38 0.046(4) 0.043(4) 0.038(4) 0.014(3) -0.001(3) 0.005(3) C39 0.045(4) 0.031(4) 0.035(4) 0.002(3) 0.014(4) -0.015(3) C40 0.028(3) 0.038(4) 0.031(3) 0.004(3) 0.000(3) -0.004(3) C41 0.046(4) 0.041(4) 0.032(4) -0.003(3) -0.008(3) -0.015(3) C42 0.051(4) 0.037(4) 0.033(4) -0.007(3) 0.000(3) 0.009(3) C43 0.033(4) 0.052(4) 0.029(4) 0.004(3) 0.006(3) 0.004(3) C44 0.039(4) 0.044(4) 0.040(4) 0.001(4) -0.008(3) -0.002(3) C45 0.046(4) 0.035(4) 0.029(4) -0.006(3) 0.002(3) 0.007(3) C46 0.056(4) 0.049(5) 0.034(4) -0.004(3) -0.011(3) -0.007(3) C47 0.068(4) 0.027(4) 0.040(4) -0.006(3) -0.001(3) 0.007(3) C48 0.041(3) 0.037(5) 0.048(5) -0.006(4) 0.002(3) 0.010(3) C49 0.032(3) 0.028(4) 0.040(4) 0.007(3) 0.004(3) 0.005(3) C50 0.037(4) 0.035(4) 0.061(5) 0.011(4) 0.005(4) -0.003(3) C51 0.032(4) 0.075(5) 0.072(5) -0.005(5) -0.005(4) -0.007(4) C52 0.047(4) 0.048(5) 0.067(5) 0.013(4) 0.007(4) -0.007(3) C53 0.053(4) 0.056(5) 0.043(4) 0.011(4) -0.015(4) 0.014(4) C54 0.023(3) 0.043(4) 0.064(5) -0.001(4) 0.007(4) -0.003(3) C55 0.048(4) 0.049(5) 0.041(4) -0.004(4) -0.001(4) -0.011(3) C56 0.054(4) 0.057(5) 0.059(5) -0.009(4) 0.004(4) -0.009(4) C57 0.087(7) 0.287(16) 0.041(5) 0.021(7) -0.017(5) -0.062(8) C58 0.141(12) 0.227(17) 0.34(2) 0.068(18) 0.031(15) 0.084(11) C59 0.033 0.040 0.052 -0.002 -0.001 -0.008 C60 0.053(4) 0.055(5) 0.045(4) -0.004(3) -0.011(3) -0.006(3) C61 0.050(4) 0.079(5) 0.052(5) -0.005(4) -0.018(4) -0.009(4) C62 0.053(4) 0.090(6) 0.096(6) -0.033(5) -0.012(4) 0.000(4) C63 0.060(4) 0.041(4) 0.044(4) 0.011(3) -0.008(3) -0.006(3) C64 0.090(5) 0.036(4) 0.076(5) 0.017(4) -0.022(4) -0.011(4) C65 0.085(5) 0.046(5) 0.050(5) 0.008(3) -0.004(4) -0.006(4) C66 0.225(10) 0.048(5) 0.074(6) 0.005(4) 0.033(7) -0.003(6) C67 0.059(4) 0.041(4) 0.041(4) 0.008(3) 0.002(4) 0.011(3) C68 0.070(4) 0.063(5) 0.044(4) -0.008(4) 0.006(4) -0.001(4) C69 0.110(6) 0.064(5) 0.030(4) -0.009(4) -0.005(4) 0.028(5) C70 0.081(5) 0.135(8) 0.057(5) -0.035(5) 0.002(5) -0.010(5) C71 0.047(3) 0.037(4) 0.033(4) -0.004(3) -0.003(3) -0.004(3) C72 0.037(3) 0.048(4) 0.049(4) 0.002(3) 0.001(3) 0.001(3) C73 0.056(4) 0.065(5) 0.031(4) 0.003(3) 0.000(3) 0.009(3) C74 0.068(4) 0.074(5) 0.035(4) 0.006(4) 0.001(4) 0.006(4) C75 0.060(4) 0.042(4) 0.044(4) -0.004(3) 0.004(3) -0.013(3) C76 0.077(4) 0.034(4) 0.064(5) 0.002(3) -0.008(4) 0.001(4) C77 0.149(12) 0.153(13) 0.35(2) -0.056(13) -0.112(14) -0.061(10) C78 0.093(8) 0.118(11) 0.37(2) -0.022(12) -0.027(12) -0.004(7) C79 0.030(3) 0.064(4) 0.038(4) 0.004(3) 0.002(3) 0.006(3) C80 0.048(4) 0.060(5) 0.046(4) -0.006(3) 0.001(3) 0.012(3) C81 0.055(4) 0.088(6) 0.045(4) -0.010(4) -0.002(4) 0.019(4) C82 0.066(4) 0.101(6) 0.045(4) 0.004(4) -0.010(4) 0.018(4) C83 0.030(3) 0.047(4) 0.032(3) -0.004(3) -0.001(3) 0.001(3) C84 0.056(4) 0.029(4) 0.040(4) -0.005(3) 0.001(3) -0.002(3) C85 0.058(4) 0.051(5) 0.071(5) 0.006(4) 0.010(4) -0.021(3) C86 0.135(7) 0.076(6) 0.094(6) -0.008(5) 0.033(6) -0.063(5) N1 0.063(3) 0.025(3) 0.047(3) 0.007(3) -0.002(3) -0.007(3) N2 0.041(3) 0.049(3) 0.026(3) 0.006(2) 0.009(3) -0.007(2) N3 0.043(3) 0.069(4) 0.032(3) -0.013(3) 0.011(3) 0.000(3) N4 0.056(3) 0.032(3) 0.038(3) 0.002(3) 0.000(3) -0.012(2) N5 0.068(3) 0.025(3) 0.050(4) 0.000(3) 0.016(3) -0.006(2) N6 0.027(3) 0.046(4) 0.056(3) 0.006(3) -0.003(2) 0.001(2) N7 0.029(3) 0.048(4) 0.045(3) 0.003(3) -0.004(2) 0.011(3) N8 0.040(3) 0.038(3) 0.034(3) -0.006(3) -0.001(2) 0.001(2) N9 0.044(3) 0.036(3) 0.041(3) 0.004(3) -0.012(2) 0.011(3) N10 0.045(3) 0.036(3) 0.056(3) -0.006(3) -0.018(3) 0.015(3) N11 0.041(3) 0.049(3) 0.025(3) 0.010(2) 0.003(3) -0.004(2) N12 0.038(3) 0.065(4) 0.018(3) 0.005(2) 0.002(3) 0.000(2) N13 0.060(3) 0.040(3) 0.034(3) 0.001(3) -0.005(3) 0.002(3) N14 0.048(3) 0.029(3) 0.042(3) -0.003(3) -0.002(3) -0.002(2) N15 0.029(2) 0.035(3) 0.029(3) 0.009(2) -0.008(2) -0.004(2) N16 0.028(2) 0.034(3) 0.025(3) -0.003(2) 0.004(2) 0.001(2) O2 0.038(2) 0.037(2) 0.038(2) 0.0014(18) -0.0035(19) -0.0040(17) O3 0.046(2) 0.038(2) 0.033(2) 0.0021(18) -0.006(2) 0.0047(18) O4 0.038(2) 0.032(2) 0.030(2) 0.0047(18) 0.0024(18) 0.0098(17) O5 0.074(3) 0.053(3) 0.026(3) 0.006(2) 0.009(2) 0.008(2) O6 0.081(3) 0.031(3) 0.048(3) -0.012(2) 0.019(2) 0.005(2) O7 0.032(2) 0.048(3) 0.078(3) 0.017(2) 0.001(2) 0.007(2) O8 0.040(2) 0.045(3) 0.069(3) 0.001(2) -0.013(2) 0.009(2) O9 0.051(2) 0.065(3) 0.026(2) 0.013(2) 0.010(2) 0.002(2) O10 0.080(3) 0.033(3) 0.057(3) -0.009(2) 0.005(2) 0.006(2) F1 0.082(3) 0.051(3) 0.078(3) -0.001(2) -0.032(2) -0.001(2) F2 0.128(4) 0.074(3) 0.098(3) -0.028(3) -0.044(3) 0.049(3) F3 0.071(3) 0.123(4) 0.065(3) 0.019(3) 0.013(2) 0.052(3) F4 0.045(2) 0.097(4) 0.181(5) 0.021(3) 0.004(3) -0.007(2) F5 0.057(2) 0.075(3) 0.180(5) -0.042(3) -0.005(3) -0.002(2) F6 0.056(2) 0.080(3) 0.084(3) 0.009(2) -0.004(2) -0.018(2) F7 0.082(3) 0.097(4) 0.118(4) 0.024(3) 0.030(3) -0.030(3) F8 0.162(4) 0.092(4) 0.079(3) 0.039(3) 0.030(3) -0.011(3) F9 0.159(4) 0.109(4) 0.070(3) 0.007(3) -0.035(3) -0.003(3) F10 0.077(3) 0.086(3) 0.082(3) -0.006(2) -0.007(2) -0.026(2) F11 0.055(2) 0.046(2) 0.044(2) 0.0015(18) -0.0034(18) 0.0052(16) F12 0.065(2) 0.051(2) 0.070(3) 0.014(2) -0.004(2) 0.0124(18) F13 0.074(3) 0.048(3) 0.109(3) 0.002(2) -0.025(2) 0.0071(19) F14 0.098(3) 0.063(3) 0.083(3) -0.023(2) -0.040(3) 0.009(2) F15 0.075(2) 0.066(3) 0.056(2) 0.007(2) -0.018(2) 0.017(2) F16 0.071(2) 0.060(3) 0.056(3) 0.003(2) -0.023(2) 0.0012(19) F17 0.102(3) 0.055(3) 0.105(3) 0.021(3) -0.035(3) 0.001(2) F18 0.116(3) 0.038(3) 0.143(4) -0.015(3) -0.048(3) 0.013(2) F19 0.109(3) 0.064(3) 0.098(3) -0.036(3) -0.041(3) 0.021(2) F20 0.087(3) 0.054(2) 0.060(3) -0.008(2) -0.024(2) 0.019(2) F21 0.054(2) 0.056(2) 0.067(2) -0.019(2) -0.003(2) -0.0137(18) F22 0.063(2) 0.068(3) 0.056(2) -0.021(2) 0.000(2) 0.0113(19) F23 0.0379(19) 0.097(3) 0.050(2) -0.011(2) 0.0007(17) 0.0117(18) F24 0.049(2) 0.064(3) 0.078(3) -0.010(2) -0.015(2) -0.0128(19) F25 0.058(2) 0.060(2) 0.071(3) -0.035(2) -0.009(2) 0.0075(18) F26 0.050(2) 0.087(3) 0.066(3) 0.010(2) -0.013(2) -0.0121(19) F27 0.064(2) 0.113(3) 0.093(3) 0.017(3) 0.000(2) -0.043(2) F28 0.086(3) 0.088(3) 0.078(3) 0.031(3) 0.015(2) -0.020(2) F29 0.071(2) 0.082(3) 0.069(3) 0.032(2) -0.008(2) 0.007(2) F30 0.042(2) 0.068(2) 0.054(2) 0.0120(19) -0.0059(18) -0.0061(18) P1 0.0380(8) 0.0303(9) 0.0257(8) 0.0011(7) -0.0034(8) 0.0080(7) O1 0.042(2) 0.046(3) 0.039(3) -0.005(2) 0.001(2) 0.014(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 C1 N1 1.475(7) . ? C1 C2 1.515(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.432(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O5 1.224(6) . ? C3 N2 1.345(6) . ? C3 N3 1.391(7) . ? C4 C5 1.374(8) . ? C4 N3 1.381(7) . ? C4 C9 1.385(8) . ? C5 F1 1.345(7) . ? C5 C6 1.372(9) . ? C6 F2 1.345(7) . ? C6 C7 1.358(9) . ? C7 F3 1.349(7) . ? C7 C8 1.371(9) . ? C8 F4 1.353(8) . ? C8 C9 1.380(9) . ? C9 F5 1.356(7) . ? C10 N1 1.464(7) . ? C10 C11 1.526(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N4 1.437(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O6 1.207(6) . ? C12 N4 1.377(7) . ? C12 N5 1.383(7) . ? C13 C14 1.346(8) . ? C13 C18 1.373(8) . ? C13 N5 1.402(7) . ? C14 F6 1.346(7) . ? C14 C15 1.404(9) . ? C15 F7 1.331(7) . ? C15 C16 1.357(10) . ? C16 C17 1.338(10) . ? C16 F8 1.369(8) . ? C17 F9 1.317(8) . ? C17 C18 1.411(9) . ? C18 F10 1.329(7) . ? C19 N1 1.471(6) . ? C19 C20 1.511(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N6 1.420(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 O7 1.220(6) . ? C21 N6 1.360(7) . ? C21 N7 1.370(7) . ? C22 C23 1.374(8) . ? C22 C27 1.381(8) . ? C22 N7 1.396(7) . ? C23 F11 1.344(6) . ? C23 C24 1.353(8) . ? C24 F12 1.357(7) . ? C24 C25 1.370(9) . ? C25 F13 1.360(7) . ? C25 C26 1.371(9) . ? C26 C27 1.335(8) . ? C26 F14 1.366(7) . ? C27 F15 1.363(6) . ? C28 N8 1.454(6) . ? C28 C29 1.509(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N9 1.456(7) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O8 1.227(6) . ? C30 N9 1.334(7) . ? C30 N10 1.389(7) . ? C31 C32 1.372(8) . ? C31 N10 1.399(7) . ? C31 C36 1.405(8) . ? C32 F16 1.336(7) . ? C32 C33 1.374(9) . ? C33 C34 1.353(9) . ? C33 F17 1.374(7) . ? C34 C35 1.348(9) . ? C34 F18 1.354(7) . ? C35 C36 1.351(8) . ? C35 F19 1.352(7) . ? C36 F20 1.342(7) . ? C37 N8 1.459(7) . ? C37 C38 1.484(7) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 N11 1.473(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 O9 1.218(6) . ? C39 N11 1.337(6) . ? C39 N12 1.387(7) . ? C40 C45 1.366(7) . ? C40 C41 1.385(7) . ? C40 N12 1.392(6) . ? C41 F21 1.343(6) . ? C41 C42 1.356(7) . ? C42 F22 1.343(6) . ? C42 C43 1.356(7) . ? C43 F23 1.357(6) . ? C43 C44 1.366(8) . ? C44 F24 1.357(6) . ? C44 C45 1.377(7) . ? C45 F25 1.328(6) . ? C46 N8 1.452(7) . ? C46 C47 1.525(8) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 N13 1.465(7) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O10 1.215(7) . ? C48 N13 1.344(7) . ? C48 N14 1.414(7) . ? C49 C54 1.361(8) . ? C49 C50 1.374(8) . ? C49 N14 1.403(7) . ? C50 F26 1.343(6) . ? C50 C51 1.380(9) . ? C51 C52 1.323(8) . ? C51 F27 1.355(7) . ? C52 F28 1.348(7) . ? C52 C53 1.369(8) . ? C53 F29 1.338(6) . ? C53 C54 1.393(8) . ? C54 F30 1.348(6) . ? C55 C56 1.478(8) . ? C55 N15 1.494(7) . ? C55 H55A 1.02(6) . ? C55 H55B 0.97(6) . ? C56 C57 1.584(11) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 C58 1.241(16) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 H58A 0.9600 . ? C58 H58C 0.9600 . ? C58 H58B 0.9600 . ? C59 C60 1.486(6) . ? C59 N15 1.519(4) . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C60 C61 1.532(8) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C61 C62 1.476(8) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 C64 1.483(8) . ? C63 N15 1.522(7) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C64 C65 1.509(8) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C65 C66 1.448(9) . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C67 C68 1.496(7) . ? C67 N15 1.544(7) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 C69 1.505(8) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C69 C70 1.496(9) . ? C69 H69A 0.9700 . ? C69 H69B 0.9700 . ? C70 H70A 0.9600 . ? C70 H70B 0.9600 . ? C70 H70C 0.9600 . ? C71 C72 1.481(7) . ? C71 N16 1.509(6) . ? C71 H71A 0.9700 . ? C71 H71B 0.9700 . ? C72 C73 1.537(8) . ? C72 H72A 0.9700 . ? C72 H72B 0.9700 . ? C73 C74 1.508(8) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C74 H74A 0.9600 . ? C74 H74B 0.9600 . ? C74 H74C 0.9600 . ? C75 C76 1.496(8) . ? C75 N16 1.532(7) . ? C75 H75A 0.9700 . ? C75 H75B 0.9700 . ? C76 C77 1.500(12) . ? C76 H76A 0.9700 . ? C76 H76B 0.9700 . ? C77 C78 1.059(11) . ? C77 H77A 0.9700 . ? C77 H77B 0.9700 . ? C78 H78A 0.9600 . ? C78 H78B 0.9600 . ? C78 H78C 0.9600 . ? C79 N16 1.513(6) . ? C79 C80 1.522(8) . ? C79 H79A 0.9700 . ? C79 H79B 0.9700 . ? C80 C81 1.505(8) . ? C80 H80A 0.9700 . ? C80 H80B 0.9700 . ? C81 C82 1.546(8) . ? C81 H81A 0.9700 . ? C81 H81B 0.9700 . ? C82 H82A 0.9600 . ? C82 H82B 0.9600 . ? C82 H82C 0.9600 . ? C83 C84 1.510(7) . ? C83 N16 1.514(6) . ? C83 H83A 0.9700 . ? C83 H83B 0.9700 . ? C84 C85 1.527(7) . ? C84 H84A 0.9700 . ? C84 H84B 0.9700 . ? C85 C86 1.509(6) . ? C85 H85A 0.9700 . ? C85 H85B 0.9700 . ? C86 H86A 0.9600 . ? C86 H86B 0.9600 . ? C86 H86C 0.9600 . ? N2 H2 0.8600 . ? N3 H3 0.8600 . ? N4 H4 0.8600 . ? N5 H5 0.8600 . ? N6 H6 0.8600 . ? N7 H7 0.8600 . ? N9 H9 0.8600 . ? N10 H10 0.8600 . ? N11 H11 0.8600 . ? N12 H12 0.8600 . ? N13 H13 0.8600 . ? N14 H14 0.8600 . ? O2 P1 1.498(4) . ? O3 P1 1.511(4) . ? O4 P1 1.519(3) . ? P1 O1 1.632(4) . ? O1 H1 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 N1 C1 C2 113.4(5) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? N2 C2 C1 112.5(4) . . ? N2 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N2 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? O5 C3 N2 124.6(6) . . ? O5 C3 N3 121.7(5) . . ? N2 C3 N3 113.7(5) . . ? C5 C4 N3 123.8(6) . . ? C5 C4 C9 114.5(6) . . ? N3 C4 C9 121.7(6) . . ? F1 C5 C6 116.9(7) . . ? F1 C5 C4 119.0(6) . . ? C6 C5 C4 124.0(7) . . ? F2 C6 C7 118.9(7) . . ? F2 C6 C5 121.8(7) . . ? C7 C6 C5 119.3(7) . . ? F3 C7 C6 122.0(7) . . ? F3 C7 C8 118.0(7) . . ? C6 C7 C8 120.0(6) . . ? F4 C8 C7 122.0(7) . . ? F4 C8 C9 119.1(8) . . ? C7 C8 C9 118.9(7) . . ? F5 C9 C8 118.3(6) . . ? F5 C9 C4 118.4(6) . . ? C8 C9 C4 123.3(7) . . ? N1 C10 C11 110.8(5) . . ? N1 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N4 C11 C10 110.0(5) . . ? N4 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N4 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O6 C12 N4 124.6(6) . . ? O6 C12 N5 122.2(6) . . ? N4 C12 N5 113.0(6) . . ? C14 C13 C18 118.3(6) . . ? C14 C13 N5 121.8(6) . . ? C18 C13 N5 119.6(5) . . ? F6 C14 C13 122.0(6) . . ? F6 C14 C15 116.1(6) . . ? C13 C14 C15 121.8(7) . . ? F7 C15 C16 121.6(7) . . ? F7 C15 C14 120.7(7) . . ? C16 C15 C14 117.6(6) . . ? C17 C16 C15 123.2(7) . . ? C17 C16 F8 119.0(9) . . ? C15 C16 F8 117.7(8) . . ? F9 C17 C16 122.7(8) . . ? F9 C17 C18 119.7(7) . . ? C16 C17 C18 117.6(7) . . ? F10 C18 C13 119.8(6) . . ? F10 C18 C17 118.9(7) . . ? C13 C18 C17 121.3(6) . . ? N1 C19 C20 111.6(4) . . ? N1 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? N1 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? N6 C20 C19 113.2(5) . . ? N6 C20 H20A 108.9 . . ? C19 C20 H20A 108.9 . . ? N6 C20 H20B 108.9 . . ? C19 C20 H20B 108.9 . . ? H20A C20 H20B 107.8 . . ? O7 C21 N6 122.9(6) . . ? O7 C21 N7 123.2(6) . . ? N6 C21 N7 113.9(5) . . ? C23 C22 C27 116.2(6) . . ? C23 C22 N7 123.2(6) . . ? C27 C22 N7 120.6(6) . . ? F11 C23 C24 117.6(6) . . ? F11 C23 C22 120.5(6) . . ? C24 C23 C22 121.7(6) . . ? C23 C24 F12 120.5(6) . . ? C23 C24 C25 120.7(6) . . ? F12 C24 C25 118.7(6) . . ? F13 C25 C24 121.5(6) . . ? F13 C25 C26 120.3(7) . . ? C24 C25 C26 118.2(6) . . ? C27 C26 F14 120.4(7) . . ? C27 C26 C25 120.5(7) . . ? F14 C26 C25 119.1(6) . . ? C26 C27 F15 119.6(6) . . ? C26 C27 C22 122.7(6) . . ? F15 C27 C22 117.7(6) . . ? N8 C28 C29 111.2(5) . . ? N8 C28 H28A 109.4 . . ? C29 C28 H28A 109.4 . . ? N8 C28 H28B 109.4 . . ? C29 C28 H28B 109.4 . . ? H28A C28 H28B 108.0 . . ? N9 C29 C28 111.9(4) . . ? N9 C29 H29A 109.2 . . ? C28 C29 H29A 109.2 . . ? N9 C29 H29B 109.2 . . ? C28 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? O8 C30 N9 124.8(6) . . ? O8 C30 N10 122.4(6) . . ? N9 C30 N10 112.8(5) . . ? C32 C31 N10 123.5(6) . . ? C32 C31 C36 116.5(6) . . ? N10 C31 C36 119.9(6) . . ? F16 C32 C31 121.1(6) . . ? F16 C32 C33 118.5(6) . . ? C31 C32 C33 120.2(7) . . ? C34 C33 F17 120.1(7) . . ? C34 C33 C32 121.9(7) . . ? F17 C33 C32 118.1(7) . . ? C35 C34 C33 118.9(7) . . ? C35 C34 F18 121.4(7) . . ? C33 C34 F18 119.7(7) . . ? C34 C35 C36 120.6(7) . . ? C34 C35 F19 119.7(7) . . ? C36 C35 F19 119.6(7) . . ? F20 C36 C35 119.8(6) . . ? F20 C36 C31 118.4(6) . . ? C35 C36 C31 121.9(7) . . ? N8 C37 C38 112.2(5) . . ? N8 C37 H37A 109.2 . . ? C38 C37 H37A 109.2 . . ? N8 C37 H37B 109.2 . . ? C38 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? N11 C38 C37 111.9(4) . . ? N11 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? N11 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? O9 C39 N11 123.5(6) . . ? O9 C39 N12 122.0(5) . . ? N11 C39 N12 114.5(5) . . ? C45 C40 C41 117.0(5) . . ? C45 C40 N12 121.7(5) . . ? C41 C40 N12 121.2(5) . . ? F21 C41 C42 118.2(6) . . ? F21 C41 C40 119.7(5) . . ? C42 C41 C40 122.0(5) . . ? F22 C42 C41 120.3(6) . . ? F22 C42 C43 119.7(5) . . ? C41 C42 C43 120.1(5) . . ? C42 C43 F23 121.4(5) . . ? C42 C43 C44 119.4(5) . . ? F23 C43 C44 119.3(5) . . ? F24 C44 C43 119.5(5) . . ? F24 C44 C45 120.1(5) . . ? C43 C44 C45 120.4(5) . . ? F25 C45 C40 120.4(5) . . ? F25 C45 C44 118.5(5) . . ? C40 C45 C44 121.0(5) . . ? N8 C46 C47 111.9(4) . . ? N8 C46 H46A 109.2 . . ? C47 C46 H46A 109.2 . . ? N8 C46 H46B 109.2 . . ? C47 C46 H46B 109.2 . . ? H46A C46 H46B 107.9 . . ? N13 C47 C46 110.6(5) . . ? N13 C47 H47A 109.5 . . ? C46 C47 H47A 109.5 . . ? N13 C47 H47B 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 108.1 . . ? O10 C48 N13 127.0(6) . . ? O10 C48 N14 120.6(6) . . ? N13 C48 N14 112.4(6) . . ? C54 C49 C50 116.7(6) . . ? C54 C49 N14 120.5(5) . . ? C50 C49 N14 122.7(6) . . ? F26 C50 C49 120.1(6) . . ? F26 C50 C51 118.4(5) . . ? C49 C50 C51 121.2(6) . . ? C52 C51 F27 119.0(7) . . ? C52 C51 C50 121.4(6) . . ? F27 C51 C50 119.6(7) . . ? C51 C52 F28 121.9(6) . . ? C51 C52 C53 119.5(6) . . ? F28 C52 C53 118.5(7) . . ? F29 C53 C52 121.8(6) . . ? F29 C53 C54 119.0(6) . . ? C52 C53 C54 119.1(6) . . ? F30 C54 C49 120.4(6) . . ? F30 C54 C53 117.5(6) . . ? C49 C54 C53 122.0(5) . . ? C56 C55 N15 116.5(5) . . ? C56 C55 H55A 118(3) . . ? N15 C55 H55A 102(3) . . ? C56 C55 H55B 107(3) . . ? N15 C55 H55B 106(3) . . ? H55A C55 H55B 105(5) . . ? C55 C56 C57 116.1(7) . . ? C55 C56 H56A 108.3 . . ? C57 C56 H56A 108.3 . . ? C55 C56 H56B 108.3 . . ? C57 C56 H56B 108.3 . . ? H56A C56 H56B 107.4 . . ? C58 C57 C56 110.0(10) . . ? C58 C57 H57A 109.7 . . ? C56 C57 H57A 109.7 . . ? C58 C57 H57B 109.6 . . ? C56 C57 H57B 109.6 . . ? H57A C57 H57B 108.2 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? H58C C58 H58B 109.5 . . ? C60 C59 N15 116.0(3) . . ? C60 C59 H59A 108.3 . . ? N15 C59 H59A 108.3 . . ? C60 C59 H59B 108.3 . . ? N15 C59 H59B 108.3 . . ? H59A C59 H59B 107.4 . . ? C59 C60 C61 112.4(4) . . ? C59 C60 H60A 109.1 . . ? C61 C60 H60A 109.1 . . ? C59 C60 H60B 109.1 . . ? C61 C60 H60B 109.1 . . ? H60A C60 H60B 107.9 . . ? C62 C61 C60 115.0(6) . . ? C62 C61 H61A 108.5 . . ? C60 C61 H61A 108.5 . . ? C62 C61 H61B 108.5 . . ? C60 C61 H61B 108.5 . . ? H61A C61 H61B 107.5 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 N15 116.9(5) . . ? C64 C63 H63A 108.1 . . ? N15 C63 H63A 108.1 . . ? C64 C63 H63B 108.1 . . ? N15 C63 H63B 108.1 . . ? H63A C63 H63B 107.3 . . ? C63 C64 C65 114.6(5) . . ? C63 C64 H64A 108.6 . . ? C65 C64 H64A 108.6 . . ? C63 C64 H64B 108.6 . . ? C65 C64 H64B 108.6 . . ? H64A C64 H64B 107.6 . . ? C66 C65 C64 113.2(6) . . ? C66 C65 H65A 108.9 . . ? C64 C65 H65A 108.9 . . ? C66 C65 H65B 108.9 . . ? C64 C65 H65B 108.9 . . ? H65A C65 H65B 107.8 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C68 C67 N15 117.0(4) . . ? C68 C67 H67A 108.1 . . ? N15 C67 H67A 108.1 . . ? C68 C67 H67B 108.1 . . ? N15 C67 H67B 108.1 . . ? H67A C67 H67B 107.3 . . ? C67 C68 C69 110.9(5) . . ? C67 C68 H68A 109.5 . . ? C69 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? C69 C68 H68B 109.5 . . ? H68A C68 H68B 108.0 . . ? C70 C69 C68 116.1(6) . . ? C70 C69 H69A 108.3 . . ? C68 C69 H69A 108.3 . . ? C70 C69 H69B 108.3 . . ? C68 C69 H69B 108.3 . . ? H69A C69 H69B 107.4 . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C72 C71 N16 117.3(4) . . ? C72 C71 H71A 108.0 . . ? N16 C71 H71A 108.0 . . ? C72 C71 H71B 108.0 . . ? N16 C71 H71B 108.0 . . ? H71A C71 H71B 107.2 . . ? C71 C72 C73 112.2(5) . . ? C71 C72 H72A 109.2 . . ? C73 C72 H72A 109.2 . . ? C71 C72 H72B 109.2 . . ? C73 C72 H72B 109.2 . . ? H72A C72 H72B 107.9 . . ? C74 C73 C72 110.6(5) . . ? C74 C73 H73A 109.5 . . ? C72 C73 H73A 109.5 . . ? C74 C73 H73B 109.5 . . ? C72 C73 H73B 109.5 . . ? H73A C73 H73B 108.1 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C76 C75 N16 116.0(5) . . ? C76 C75 H75A 108.3 . . ? N16 C75 H75A 108.3 . . ? C76 C75 H75B 108.3 . . ? N16 C75 H75B 108.3 . . ? H75A C75 H75B 107.4 . . ? C75 C76 C77 117.4(7) . . ? C75 C76 H76A 108.0 . . ? C77 C76 H76A 108.0 . . ? C75 C76 H76B 108.0 . . ? C77 C76 H76B 108.0 . . ? H76A C76 H76B 107.2 . . ? C78 C77 C76 128.3(16) . . ? C78 C77 H77A 105.2 . . ? C76 C77 H77A 105.2 . . ? C78 C77 H77B 105.2 . . ? C76 C77 H77B 105.2 . . ? H77A C77 H77B 105.9 . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? N16 C79 C80 115.1(4) . . ? N16 C79 H79A 108.5 . . ? C80 C79 H79A 108.5 . . ? N16 C79 H79B 108.5 . . ? C80 C79 H79B 108.5 . . ? H79A C79 H79B 107.5 . . ? C81 C80 C79 111.5(5) . . ? C81 C80 H80A 109.3 . . ? C79 C80 H80A 109.3 . . ? C81 C80 H80B 109.3 . . ? C79 C80 H80B 109.3 . . ? H80A C80 H80B 108.0 . . ? C80 C81 C82 111.7(5) . . ? C80 C81 H81A 109.3 . . ? C82 C81 H81A 109.3 . . ? C80 C81 H81B 109.3 . . ? C82 C81 H81B 109.3 . . ? H81A C81 H81B 107.9 . . ? C81 C82 H82A 109.5 . . ? C81 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C81 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C84 C83 N16 116.1(4) . . ? C84 C83 H83A 108.3 . . ? N16 C83 H83A 108.3 . . ? C84 C83 H83B 108.3 . . ? N16 C83 H83B 108.3 . . ? H83A C83 H83B 107.4 . . ? C83 C84 C85 110.9(5) . . ? C83 C84 H84A 109.5 . . ? C85 C84 H84A 109.5 . . ? C83 C84 H84B 109.5 . . ? C85 C84 H84B 109.5 . . ? H84A C84 H84B 108.0 . . ? C86 C85 C84 112.7(5) . . ? C86 C85 H85A 109.0 . . ? C84 C85 H85A 109.0 . . ? C86 C85 H85B 109.0 . . ? C84 C85 H85B 109.0 . . ? H85A C85 H85B 107.8 . . ? C85 C86 H86A 109.5 . . ? C85 C86 H86B 109.5 . . ? H86A C86 H86B 109.5 . . ? C85 C86 H86C 109.5 . . ? H86A C86 H86C 109.5 . . ? H86B C86 H86C 109.5 . . ? C10 N1 C19 113.0(4) . . ? C10 N1 C1 110.9(4) . . ? C19 N1 C1 113.9(4) . . ? C3 N2 C2 122.6(4) . . ? C3 N2 H2 118.7 . . ? C2 N2 H2 118.7 . . ? C4 N3 C3 121.9(5) . . ? C4 N3 H3 119.1 . . ? C3 N3 H3 119.1 . . ? C12 N4 C11 119.0(5) . . ? C12 N4 H4 120.5 . . ? C11 N4 H4 120.5 . . ? C12 N5 C13 124.6(5) . . ? C12 N5 H5 117.7 . . ? C13 N5 H5 117.7 . . ? C21 N6 C20 121.3(5) . . ? C21 N6 H6 119.3 . . ? C20 N6 H6 119.3 . . ? C21 N7 C22 124.6(5) . . ? C21 N7 H7 117.7 . . ? C22 N7 H7 117.7 . . ? C46 N8 C28 113.7(4) . . ? C46 N8 C37 113.5(4) . . ? C28 N8 C37 111.8(5) . . ? C30 N9 C29 121.2(5) . . ? C30 N9 H9 119.4 . . ? C29 N9 H9 119.4 . . ? C30 N10 C31 124.0(5) . . ? C30 N10 H10 118.0 . . ? C31 N10 H10 118.0 . . ? C39 N11 C38 122.6(5) . . ? C39 N11 H11 118.7 . . ? C38 N11 H11 118.7 . . ? C39 N12 C40 120.4(5) . . ? C39 N12 H12 119.8 . . ? C40 N12 H12 119.8 . . ? C48 N13 C47 120.4(5) . . ? C48 N13 H13 119.8 . . ? C47 N13 H13 119.8 . . ? C49 N14 C48 121.6(5) . . ? C49 N14 H14 119.2 . . ? C48 N14 H14 119.2 . . ? C55 N15 C59 112.9(4) . . ? C55 N15 C63 109.3(4) . . ? C59 N15 C63 109.7(3) . . ? C55 N15 C67 108.3(4) . . ? C59 N15 C67 106.8(3) . . ? C63 N15 C67 109.7(4) . . ? C71 N16 C79 107.9(4) . . ? C71 N16 C83 109.6(4) . . ? C79 N16 C83 112.2(4) . . ? C71 N16 C75 111.2(4) . . ? C79 N16 C75 108.3(4) . . ? C83 N16 C75 107.6(4) . . ? O2 P1 O3 115.1(2) . . ? O2 P1 O4 111.90(19) . . ? O3 P1 O4 112.3(2) . . ? O2 P1 O1 107.5(2) . . ? O3 P1 O1 101.96(19) . . ? O4 P1 O1 107.1(2) . . ? P1 O1 H1 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 21.05 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.441 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.049 # Attachment 'PF_OH.cif' data_pf_oh _database_code_depnum_ccdc_archive 'CCDC 861095' #TrackingRef 'PF_OH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H54 F15 N8 O4' _chemical_formula_weight 1031.94 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' _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 13.939(2) _cell_length_b 14.194(5) _cell_length_c 14.511(3) _cell_angle_alpha 93.624(3) _cell_angle_beta 118.198(2) _cell_angle_gamma 96.509(3) _cell_volume 2491.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description COLORLESS _exptl_crystal_colour PLATE _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1070 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9676 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16668 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 24.16 _reflns_number_total 7919 _reflns_number_gt 4624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 2.3' _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^)+(0.1040P)^2^+0.7042P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7919 _refine_ls_number_parameters 659 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1072 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.2107 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.1142(4) 0.7252(4) 0.5900(3) 0.0915(13) Uani 1 1 d . . . H1A H 0.1318 0.7938 0.5926 0.110 Uiso 1 1 calc R . . H1B H 0.1293 0.7130 0.6602 0.110 Uiso 1 1 calc R . . C2 C -0.0034(3) 0.6956(3) 0.5184(3) 0.0852(12) Uani 1 1 d . . . H2A H -0.0264 0.6330 0.5313 0.102 Uiso 1 1 calc R . . H2B H -0.0436 0.7401 0.5335 0.102 Uiso 1 1 calc R . . C3 C -0.1352(3) 0.6846(2) 0.3294(3) 0.0637(9) Uani 1 1 d . . . C4 C -0.2447(3) 0.6439(3) 0.1411(3) 0.0716(10) Uani 1 1 d . . . C5 C -0.3137(4) 0.7104(4) 0.1046(4) 0.0861(12) Uani 1 1 d . . . C6 C -0.4130(4) 0.6889(5) 0.0138(4) 0.1062(16) Uani 1 1 d . . . C7 C -0.4426(4) 0.6018(6) -0.0451(4) 0.1142(19) Uani 1 1 d . . . C8 C -0.3757(5) 0.5345(5) -0.0113(4) 0.1110(16) Uani 1 1 d . . . C9 C -0.2791(4) 0.5546(4) 0.0809(4) 0.0859(12) Uani 1 1 d . . . C11 C 0.2057(4) 0.5881(3) 0.6067(3) 0.0825(11) Uani 1 1 d . . . H11A H 0.2645 0.6011 0.6793 0.099 Uiso 1 1 calc R . . H11B H 0.1394 0.5593 0.6071 0.099 Uiso 1 1 calc R . . C12 C 0.2348(4) 0.5193(3) 0.5488(3) 0.0832(12) Uani 1 1 d . . . H12A H 0.3089 0.5411 0.5609 0.100 Uiso 1 1 calc R . . H12B H 0.2341 0.4579 0.5746 0.100 Uiso 1 1 calc R . . C13 C 0.1513(3) 0.4346(3) 0.3699(3) 0.0628(9) Uani 1 1 d . . . C14 C 0.0687(3) 0.3753(3) 0.1855(3) 0.0648(9) Uani 1 1 d . . . C15 C 0.0459(3) 0.2778(3) 0.1845(3) 0.0783(11) Uani 1 1 d . . . C16 C 0.0429(4) 0.2137(4) 0.1083(4) 0.1082(16) Uani 1 1 d . . . C17 C 0.0572(5) 0.2460(6) 0.0285(5) 0.126(2) Uani 1 1 d . . . C18 C 0.0734(4) 0.3406(6) 0.0245(4) 0.1116(19) Uani 1 1 d . . . C19 C 0.0814(3) 0.4042(4) 0.1037(3) 0.0834(12) Uani 1 1 d . . . C20 C 0.2931(4) 0.7399(3) 0.5977(3) 0.0885(12) Uani 1 1 d . . . H20A H 0.3459 0.6993 0.6012 0.106 Uiso 1 1 calc R . . H20B H 0.3193 0.7720 0.6683 0.106 Uiso 1 1 calc R . . C21 C 0.2901(4) 0.8123(3) 0.5291(3) 0.0848(12) Uani 1 1 d . . . H21A H 0.2496 0.8605 0.5370 0.102 Uiso 1 1 calc R . . H21B H 0.3651 0.8435 0.5528 0.102 Uiso 1 1 calc R . . C22 C 0.2643(3) 0.8199(3) 0.3521(3) 0.0633(9) Uani 1 1 d . . . C23 C 0.2136(3) 0.8119(3) 0.1673(3) 0.0692(10) Uani 1 1 d . . . C24 C 0.2051(4) 0.9044(3) 0.1449(3) 0.0839(11) Uani 1 1 d . . . C25 C 0.2166(4) 0.9362(3) 0.0638(4) 0.1015(14) Uani 1 1 d . . . C26 C 0.2350(5) 0.8755(4) -0.0003(4) 0.1075(16) Uani 1 1 d . . . C27 C 0.2418(4) 0.7832(4) 0.0175(4) 0.1000(14) Uani 1 1 d . . . C28 C 0.2318(4) 0.7526(3) 0.1002(4) 0.0829(11) Uani 1 1 d . . . C29 C 0.7737(3) 0.8543(2) 0.5198(3) 0.0630(9) Uani 1 1 d . . . H29A H 0.8042 0.8096 0.5700 0.076 Uiso 1 1 calc R . . H29B H 0.7897 0.8394 0.4629 0.076 Uiso 1 1 calc R . . C30 C 0.8326(3) 0.9532(3) 0.5737(4) 0.0900(13) Uani 1 1 d . . . H30A H 0.8045 0.9983 0.5234 0.108 Uiso 1 1 calc R . . H30B H 0.8163 0.9693 0.6303 0.108 Uiso 1 1 calc R . . C31 C 0.9531(4) 0.9640(3) 0.6177(4) 0.1015(14) Uani 1 1 d . . . H31A H 0.9686 0.9484 0.5605 0.122 Uiso 1 1 calc R . . H31B H 0.9802 0.9176 0.6664 0.122 Uiso 1 1 calc R . . C32 C 1.0166(5) 1.0607(4) 0.6738(5) 0.148(2) Uani 1 1 d . . . H32A H 0.9968 1.1065 0.6247 0.222 Uiso 1 1 calc R . . H32B H 1.0942 1.0589 0.7043 0.222 Uiso 1 1 calc R . . H32C H 0.9996 1.0787 0.7287 0.222 Uiso 1 1 calc R . . C33 C 0.5938(3) 0.9040(3) 0.3946(3) 0.0740(10) Uani 1 1 d . . . H33A H 0.5148 0.8897 0.3682 0.089 Uiso 1 1 calc R . . H33B H 0.6186 0.9689 0.4310 0.089 Uiso 1 1 calc R . . C34 C 0.6139(5) 0.9008(4) 0.3028(4) 0.1123(16) Uani 1 1 d . . . H34A H 0.5902 0.8365 0.2650 0.135 Uiso 1 1 calc R . . H34B H 0.6920 0.9190 0.3266 0.135 Uiso 1 1 calc R . . C35 C 0.5480(6) 0.9709(5) 0.2300(5) 0.157(3) Uani 1 1 d . . . H35A H 0.4701 0.9475 0.2028 0.188 Uiso 1 1 calc R . . H35B H 0.5651 1.0321 0.2727 0.188 Uiso 1 1 calc R . . C36 C 0.5645(10) 0.9860(7) 0.1475(8) 0.260(6) Uani 1 1 d . . . H36A H 0.6364 1.0227 0.1726 0.390 Uiso 1 1 calc R . . H36B H 0.5095 1.0205 0.1009 0.390 Uiso 1 1 calc R . . H36C H 0.5593 0.9257 0.1103 0.390 Uiso 1 1 calc R . . C37 C 0.6111(3) 0.7332(2) 0.4254(3) 0.0638(9) Uani 1 1 d . . . H37A H 0.6522 0.6941 0.4786 0.077 Uiso 1 1 calc R . . H37B H 0.6302 0.7247 0.3696 0.077 Uiso 1 1 calc R . . C38 C 0.4890(3) 0.6959(3) 0.3798(4) 0.0894(12) Uani 1 1 d . . . H38A H 0.4468 0.7262 0.3182 0.107 Uiso 1 1 calc R . . H38B H 0.4658 0.7111 0.4316 0.107 Uiso 1 1 calc R . . C39 C 0.4681(4) 0.5884(3) 0.3496(5) 0.1168(17) Uani 1 1 d . . . H39A H 0.4777 0.5754 0.2883 0.140 Uiso 1 1 calc R . . H39B H 0.5237 0.5612 0.4069 0.140 Uiso 1 1 calc R . . C40 C 0.3614(6) 0.5400(4) 0.3262(7) 0.183(3) Uani 1 1 d . . . H40A H 0.3507 0.5517 0.3863 0.275 Uiso 1 1 calc R . . H40B H 0.3568 0.4725 0.3098 0.275 Uiso 1 1 calc R . . H40C H 0.3054 0.5634 0.2668 0.275 Uiso 1 1 calc R . . C41 C 0.6179(3) 0.8572(3) 0.5604(3) 0.0692(10) Uani 1 1 d . . . H41A H 0.6482 0.9231 0.5925 0.083 Uiso 1 1 calc R . . H41B H 0.5382 0.8507 0.5278 0.083 Uiso 1 1 calc R . . C42 C 0.6565(4) 0.7943(3) 0.6455(3) 0.0937(13) Uani 1 1 d . . . H42A H 0.6302 0.7279 0.6141 0.112 Uiso 1 1 calc R . . H42B H 0.7365 0.8041 0.6826 0.112 Uiso 1 1 calc R . . C43 C 0.6164(5) 0.8147(4) 0.7220(4) 0.1190(17) Uani 1 1 d . . . H43A H 0.6485 0.8797 0.7570 0.143 Uiso 1 1 calc R . . H43B H 0.5371 0.8123 0.6826 0.143 Uiso 1 1 calc R . . C44 C 0.6397(6) 0.7510(5) 0.8040(5) 0.156(3) Uani 1 1 d . . . H44A H 0.6370 0.6872 0.7754 0.235 Uiso 1 1 calc R . . H44B H 0.5856 0.7508 0.8272 0.235 Uiso 1 1 calc R . . H44C H 0.7118 0.7735 0.8627 0.235 Uiso 1 1 calc R . . H2 H 0.017(3) 0.673(3) 0.388(3) 0.085(12) Uiso 1 1 d . . . H3 H -0.090(3) 0.648(2) 0.229(3) 0.061(10) Uiso 1 1 d . . . H4 H 0.132(3) 0.557(3) 0.415(3) 0.089(14) Uiso 1 1 d . . . H5 H 0.072(4) 0.489(3) 0.256(3) 0.084(16) Uiso 1 1 d . . . H6 H 0.192(3) 0.730(3) 0.395(3) 0.065(12) Uiso 1 1 d . . . H7 H 0.161(3) 0.723(3) 0.241(3) 0.076(12) Uiso 1 1 d . . . N1 N 0.1868(2) 0.67948(18) 0.5636(2) 0.0571(7) Uani 1 1 d . . . N2 N -0.0319(3) 0.6914(2) 0.4085(2) 0.0727(9) Uani 1 1 d . . . N3 N -0.1431(3) 0.6642(2) 0.2328(2) 0.0727(9) Uani 1 1 d . . . N4 N 0.1580(3) 0.5078(2) 0.4366(2) 0.0760(10) Uani 1 1 d . . . N5 N 0.0784(3) 0.4408(3) 0.2660(2) 0.0683(9) Uani 1 1 d . . . N6 N 0.2414(3) 0.7764(2) 0.4203(3) 0.0729(9) Uani 1 1 d . . . N7 N 0.2006(3) 0.7781(3) 0.2500(3) 0.0734(9) Uani 1 1 d . . . N8 N 0.6486(2) 0.83694(18) 0.4744(2) 0.0596(7) Uani 1 1 d . . . O1 O -0.2141(2) 0.6962(2) 0.3416(2) 0.0861(8) Uani 1 1 d . . . O2 O 0.2017(2) 0.36800(17) 0.39678(19) 0.0788(7) Uani 1 1 d . . . O3 O 0.3372(2) 0.88919(17) 0.3787(2) 0.0756(7) Uani 1 1 d . . . O4 O 0.06750(14) 0.63398(12) 0.28412(14) 0.0405(5) Uani 1 1 d . . . F1 F -0.2838(2) 0.7985(2) 0.1564(2) 0.1208(9) Uani 1 1 d . . . F2 F -0.4787(3) 0.7549(3) -0.0202(3) 0.1634(14) Uani 1 1 d . . . F3 F -0.5391(3) 0.5817(3) -0.1360(2) 0.1761(16) Uani 1 1 d . . . F4 F -0.4065(3) 0.4475(3) -0.0688(3) 0.1646(14) Uani 1 1 d . . . F5 F -0.2155(3) 0.4882(2) 0.1137(2) 0.1236(9) Uani 1 1 d . . . F6 F 0.0222(2) 0.24314(16) 0.2555(2) 0.1066(8) Uani 1 1 d . . . F7 F 0.0244(3) 0.1202(2) 0.1120(3) 0.1675(16) Uani 1 1 d . . . F8 F 0.0536(3) 0.1829(4) -0.0470(3) 0.203(2) Uani 1 1 d . . . F9 F 0.0866(3) 0.3745(4) -0.0537(2) 0.1872(19) Uani 1 1 d . . . F10 F 0.1014(2) 0.4987(2) 0.1009(2) 0.1240(10) Uani 1 1 d . . . F11 F 0.1806(3) 0.96516(17) 0.2020(2) 0.1126(9) Uani 1 1 d . . . F12 F 0.2069(4) 1.0262(2) 0.0444(3) 0.1593(14) Uani 1 1 d . . . F13 F 0.2448(4) 0.9060(3) -0.0819(3) 0.1660(14) Uani 1 1 d . . . F14 F 0.2587(3) 0.7229(2) -0.0468(3) 0.1547(13) Uani 1 1 d . . . F15 F 0.2394(3) 0.66131(18) 0.1162(2) 0.1209(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.087(3) 0.127(4) 0.070(3) 0.005(2) 0.042(2) 0.038(3) C2 0.075(3) 0.122(3) 0.068(3) 0.001(2) 0.044(2) 0.017(2) C3 0.059(2) 0.074(2) 0.067(2) 0.0081(18) 0.037(2) 0.0159(18) C4 0.065(3) 0.097(3) 0.065(2) 0.014(2) 0.040(2) 0.020(2) C5 0.074(3) 0.110(4) 0.082(3) 0.017(3) 0.040(3) 0.029(3) C6 0.074(3) 0.158(5) 0.091(4) 0.040(4) 0.036(3) 0.041(4) C7 0.063(3) 0.194(7) 0.068(3) 0.024(4) 0.020(3) 0.004(4) C8 0.101(4) 0.136(5) 0.082(4) -0.008(3) 0.043(3) -0.016(4) C9 0.080(3) 0.100(3) 0.079(3) 0.009(3) 0.041(3) 0.010(3) C11 0.101(3) 0.081(3) 0.058(2) 0.014(2) 0.030(2) 0.023(2) C12 0.108(3) 0.065(2) 0.064(2) 0.0138(19) 0.029(2) 0.027(2) C13 0.075(2) 0.061(2) 0.059(2) 0.0146(18) 0.035(2) 0.0183(19) C14 0.063(2) 0.081(3) 0.055(2) 0.0111(18) 0.0300(18) 0.0226(19) C15 0.084(3) 0.077(3) 0.074(3) 0.003(2) 0.037(2) 0.023(2) C16 0.102(4) 0.104(4) 0.091(4) -0.013(3) 0.021(3) 0.044(3) C17 0.088(4) 0.194(7) 0.074(4) -0.039(4) 0.022(3) 0.053(4) C18 0.070(3) 0.214(7) 0.054(3) 0.005(4) 0.032(2) 0.032(4) C19 0.065(3) 0.119(4) 0.066(3) 0.023(3) 0.031(2) 0.013(2) C20 0.089(3) 0.083(3) 0.075(3) 0.000(2) 0.031(2) -0.012(2) C21 0.084(3) 0.078(3) 0.085(3) 0.006(2) 0.040(2) -0.007(2) C22 0.059(2) 0.056(2) 0.084(3) 0.012(2) 0.040(2) 0.0139(18) C23 0.072(2) 0.062(2) 0.084(3) 0.013(2) 0.046(2) 0.0064(18) C24 0.102(3) 0.069(3) 0.092(3) 0.018(2) 0.054(3) 0.020(2) C25 0.140(4) 0.068(3) 0.107(4) 0.031(3) 0.067(3) 0.013(3) C26 0.137(4) 0.108(4) 0.100(4) 0.028(3) 0.077(3) 0.004(3) C27 0.121(4) 0.101(4) 0.105(4) 0.008(3) 0.077(3) 0.018(3) C28 0.092(3) 0.067(3) 0.101(3) 0.017(2) 0.055(3) 0.012(2) C29 0.056(2) 0.063(2) 0.080(2) 0.0122(18) 0.0394(19) 0.0153(17) C30 0.067(3) 0.069(3) 0.128(4) 0.000(2) 0.044(3) 0.010(2) C31 0.079(3) 0.089(3) 0.131(4) 0.015(3) 0.050(3) -0.001(2) C32 0.104(4) 0.108(4) 0.191(6) -0.007(4) 0.050(4) -0.027(3) C33 0.069(2) 0.064(2) 0.094(3) 0.029(2) 0.039(2) 0.0231(19) C34 0.128(4) 0.125(4) 0.111(4) 0.060(3) 0.068(3) 0.047(3) C35 0.184(7) 0.165(6) 0.126(5) 0.071(5) 0.068(5) 0.049(5) C36 0.386(17) 0.262(11) 0.220(10) 0.154(9) 0.181(11) 0.151(11) C37 0.061(2) 0.054(2) 0.079(2) 0.0047(17) 0.0362(19) 0.0135(16) C38 0.071(3) 0.070(3) 0.124(4) -0.002(2) 0.048(3) 0.003(2) C39 0.084(3) 0.089(3) 0.154(5) -0.017(3) 0.048(3) -0.010(3) C40 0.160(7) 0.112(5) 0.265(9) 0.017(5) 0.100(7) -0.008(4) C41 0.069(2) 0.067(2) 0.089(3) 0.0045(19) 0.052(2) 0.0164(18) C42 0.112(4) 0.107(3) 0.092(3) 0.029(3) 0.067(3) 0.043(3) C43 0.113(4) 0.152(5) 0.117(4) 0.024(4) 0.074(4) 0.022(3) C44 0.165(6) 0.207(7) 0.143(5) 0.076(5) 0.102(5) 0.043(5) N1 0.0579(17) 0.0579(16) 0.0566(16) 0.0057(13) 0.0284(14) 0.0113(13) N2 0.062(2) 0.102(2) 0.066(2) 0.0119(16) 0.0385(18) 0.0238(17) N3 0.058(2) 0.102(2) 0.067(2) 0.0075(16) 0.0358(18) 0.0244(18) N4 0.107(3) 0.0573(19) 0.0603(19) 0.0128(16) 0.0330(18) 0.0321(19) N5 0.087(2) 0.061(2) 0.062(2) 0.0173(17) 0.0373(18) 0.0214(18) N6 0.072(2) 0.067(2) 0.077(2) 0.0040(18) 0.0388(19) -0.0075(18) N7 0.071(2) 0.069(2) 0.080(2) 0.0111(18) 0.0395(19) -0.0020(17) N8 0.0555(17) 0.0559(16) 0.0761(18) 0.0121(14) 0.0367(15) 0.0171(13) O1 0.0658(17) 0.129(2) 0.0805(18) 0.0096(15) 0.0463(15) 0.0294(15) O2 0.101(2) 0.0659(16) 0.0728(16) 0.0191(13) 0.0381(15) 0.0393(15) O3 0.0627(16) 0.0655(16) 0.1009(19) 0.0128(14) 0.0433(15) 0.0005(13) O4 0.0420(11) 0.0404(10) 0.0442(11) 0.0076(8) 0.0241(9) 0.0104(8) F1 0.126(2) 0.113(2) 0.121(2) 0.0156(17) 0.0499(19) 0.0553(18) F2 0.117(2) 0.238(4) 0.144(3) 0.074(3) 0.051(2) 0.093(3) F3 0.090(2) 0.294(5) 0.093(2) 0.028(3) 0.0119(19) -0.011(3) F4 0.161(3) 0.162(3) 0.124(3) -0.043(2) 0.052(2) -0.037(2) F5 0.141(3) 0.0978(19) 0.126(2) 0.0039(16) 0.059(2) 0.0308(18) F6 0.141(2) 0.0751(15) 0.1045(18) 0.0194(13) 0.0613(18) 0.0069(14) F7 0.185(3) 0.095(2) 0.147(3) -0.0318(19) 0.019(2) 0.053(2) F8 0.156(3) 0.315(5) 0.102(2) -0.074(3) 0.030(2) 0.109(3) F9 0.127(3) 0.380(6) 0.0743(18) 0.031(3) 0.0652(19) 0.038(3) F10 0.112(2) 0.155(3) 0.0857(18) 0.0461(17) 0.0375(16) -0.0172(18) F11 0.164(3) 0.0804(16) 0.117(2) 0.0226(14) 0.080(2) 0.0478(16) F12 0.258(4) 0.091(2) 0.147(3) 0.0521(19) 0.108(3) 0.029(2) F13 0.237(4) 0.164(3) 0.141(3) 0.044(2) 0.131(3) 0.005(3) F14 0.222(4) 0.148(3) 0.157(3) 0.009(2) 0.141(3) 0.044(2) F15 0.175(3) 0.0743(17) 0.136(2) 0.0162(15) 0.091(2) 0.0327(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.441(4) . ? C1 C2 1.456(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.446(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.220(4) . ? C3 N2 1.338(5) . ? C3 N3 1.364(4) . ? C4 C5 1.373(6) . ? C4 C9 1.388(6) . ? C4 N3 1.392(5) . ? C5 F1 1.330(5) . ? C5 C6 1.369(7) . ? C6 F2 1.335(6) . ? C6 C7 1.360(8) . ? C7 F3 1.349(5) . ? C7 C8 1.361(8) . ? C8 F4 1.348(6) . ? C8 C9 1.358(7) . ? C9 F5 1.322(5) . ? C11 C12 1.461(5) . ? C11 N1 1.472(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.451(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O2 1.216(4) . ? C13 N4 1.338(4) . ? C13 N5 1.379(5) . ? C14 C19 1.362(5) . ? C14 C15 1.382(5) . ? C14 N5 1.390(5) . ? C15 F6 1.328(5) . ? C15 C16 1.369(6) . ? C16 F7 1.332(6) . ? C16 C17 1.362(9) . ? C17 C18 1.346(8) . ? C17 F8 1.349(6) . ? C18 F9 1.341(6) . ? C18 C19 1.369(7) . ? C19 F10 1.345(5) . ? C20 N1 1.464(5) . ? C20 C21 1.466(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N6 1.422(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 O3 1.226(4) . ? C22 N6 1.339(5) . ? C22 N7 1.365(5) . ? C23 C24 1.377(5) . ? C23 C28 1.379(5) . ? C23 N7 1.400(5) . ? C24 F11 1.339(4) . ? C24 C25 1.358(6) . ? C25 F12 1.332(5) . ? C25 C26 1.360(7) . ? C26 F13 1.346(5) . ? C26 C27 1.356(6) . ? C27 F14 1.346(5) . ? C27 C28 1.363(6) . ? C28 F15 1.338(4) . ? C29 C30 1.500(5) . ? C29 N8 1.527(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.473(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.494(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.483(6) . ? C33 N8 1.517(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.540(7) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.347(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N8 1.513(4) . ? C37 C38 1.516(5) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.517(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.435(8) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 C42 1.494(5) . ? C41 N8 1.519(4) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.488(6) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.474(7) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? N2 H2 0.91(4) . ? N3 H3 0.83(3) . ? N4 H4 0.83(4) . ? N5 H5 0.71(4) . ? N6 H6 0.82(4) . ? N7 H7 0.87(4) . ? O4 O4 0.000(5) 1 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 115.8(3) . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? N2 C2 C1 113.1(3) . . ? N2 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N2 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O1 C3 N2 124.2(3) . . ? O1 C3 N3 123.2(4) . . ? N2 C3 N3 112.7(3) . . ? C5 C4 C9 117.1(4) . . ? C5 C4 N3 122.5(4) . . ? C9 C4 N3 120.5(4) . . ? F1 C5 C6 118.5(5) . . ? F1 C5 C4 120.1(4) . . ? C6 C5 C4 121.4(5) . . ? F2 C6 C7 119.6(6) . . ? F2 C6 C5 120.3(6) . . ? C7 C6 C5 120.0(5) . . ? F3 C7 C6 119.9(7) . . ? F3 C7 C8 120.2(7) . . ? C6 C7 C8 119.9(5) . . ? F4 C8 C9 120.2(6) . . ? F4 C8 C7 119.7(6) . . ? C9 C8 C7 120.1(5) . . ? F5 C9 C8 119.6(5) . . ? F5 C9 C4 118.9(4) . . ? C8 C9 C4 121.5(5) . . ? C12 C11 N1 114.6(3) . . ? C12 C11 H11A 108.6 . . ? N1 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? N1 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? N4 C12 C11 111.0(3) . . ? N4 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? N4 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O2 C13 N4 124.3(3) . . ? O2 C13 N5 122.7(3) . . ? N4 C13 N5 112.9(3) . . ? C19 C14 C15 116.7(4) . . ? C19 C14 N5 121.5(4) . . ? C15 C14 N5 121.8(3) . . ? F6 C15 C16 117.6(5) . . ? F6 C15 C14 120.9(3) . . ? C16 C15 C14 121.4(5) . . ? F7 C16 C17 120.6(6) . . ? F7 C16 C15 119.7(6) . . ? C17 C16 C15 119.7(5) . . ? C18 C17 F8 120.3(8) . . ? C18 C17 C16 120.0(5) . . ? F8 C17 C16 119.8(8) . . ? F9 C18 C17 121.3(6) . . ? F9 C18 C19 118.8(7) . . ? C17 C18 C19 119.9(5) . . ? F10 C19 C14 118.3(4) . . ? F10 C19 C18 119.5(5) . . ? C14 C19 C18 122.2(5) . . ? N1 C20 C21 114.5(3) . . ? N1 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? N1 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? N6 C21 C20 114.7(3) . . ? N6 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? N6 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? O3 C22 N6 123.5(4) . . ? O3 C22 N7 123.0(4) . . ? N6 C22 N7 113.5(3) . . ? C24 C23 C28 115.5(4) . . ? C24 C23 N7 122.9(4) . . ? C28 C23 N7 121.5(3) . . ? F11 C24 C25 117.9(4) . . ? F11 C24 C23 119.5(4) . . ? C25 C24 C23 122.6(4) . . ? F12 C25 C24 120.6(5) . . ? F12 C25 C26 119.4(4) . . ? C24 C25 C26 120.0(4) . . ? F13 C26 C27 120.0(5) . . ? F13 C26 C25 120.4(5) . . ? C27 C26 C25 119.5(4) . . ? F14 C27 C26 119.4(5) . . ? F14 C27 C28 120.7(5) . . ? C26 C27 C28 119.8(4) . . ? F15 C28 C27 118.6(4) . . ? F15 C28 C23 118.9(4) . . ? C27 C28 C23 122.5(4) . . ? C30 C29 N8 116.5(3) . . ? C30 C29 H29A 108.2 . . ? N8 C29 H29A 108.2 . . ? C30 C29 H29B 108.2 . . ? N8 C29 H29B 108.2 . . ? H29A C29 H29B 107.3 . . ? C31 C30 C29 113.4(3) . . ? C31 C30 H30A 108.9 . . ? C29 C30 H30A 108.9 . . ? C31 C30 H30B 108.9 . . ? C29 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C30 C31 C32 116.0(4) . . ? C30 C31 H31A 108.3 . . ? C32 C31 H31A 108.3 . . ? C30 C31 H31B 108.3 . . ? C32 C31 H31B 108.3 . . ? H31A C31 H31B 107.4 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N8 116.4(3) . . ? C34 C33 H33A 108.2 . . ? N8 C33 H33A 108.2 . . ? C34 C33 H33B 108.2 . . ? N8 C33 H33B 108.2 . . ? H33A C33 H33B 107.3 . . ? C33 C34 C35 108.1(4) . . ? C33 C34 H34A 110.1 . . ? C35 C34 H34A 110.1 . . ? C33 C34 H34B 110.1 . . ? C35 C34 H34B 110.1 . . ? H34A C34 H34B 108.4 . . ? C36 C35 C34 117.2(7) . . ? C36 C35 H35A 108.0 . . ? C34 C35 H35A 108.0 . . ? C36 C35 H35B 108.0 . . ? C34 C35 H35B 108.0 . . ? H35A C35 H35B 107.2 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N8 C37 C38 115.9(3) . . ? N8 C37 H37A 108.3 . . ? C38 C37 H37A 108.3 . . ? N8 C37 H37B 108.3 . . ? C38 C37 H37B 108.3 . . ? H37A C37 H37B 107.4 . . ? C37 C38 C39 109.3(3) . . ? C37 C38 H38A 109.8 . . ? C39 C38 H38A 109.8 . . ? C37 C38 H38B 109.8 . . ? C39 C38 H38B 109.8 . . ? H38A C38 H38B 108.3 . . ? C40 C39 C38 115.7(5) . . ? C40 C39 H39A 108.4 . . ? C38 C39 H39A 108.4 . . ? C40 C39 H39B 108.4 . . ? C38 C39 H39B 108.4 . . ? H39A C39 H39B 107.4 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 N8 115.4(3) . . ? C42 C41 H41A 108.4 . . ? N8 C41 H41A 108.4 . . ? C42 C41 H41B 108.4 . . ? N8 C41 H41B 108.4 . . ? H41A C41 H41B 107.5 . . ? C43 C42 C41 111.7(4) . . ? C43 C42 H42A 109.3 . . ? C41 C42 H42A 109.3 . . ? C43 C42 H42B 109.3 . . ? C41 C42 H42B 109.3 . . ? H42A C42 H42B 107.9 . . ? C44 C43 C42 116.9(5) . . ? C44 C43 H43A 108.1 . . ? C42 C43 H43A 108.1 . . ? C44 C43 H43B 108.1 . . ? C42 C43 H43B 108.1 . . ? H43A C43 H43B 107.3 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C1 N1 C20 113.4(3) . . ? C1 N1 C11 111.6(3) . . ? C20 N1 C11 109.3(3) . . ? C3 N2 C2 123.9(3) . . ? C3 N2 H2 114(2) . . ? C2 N2 H2 119(2) . . ? C3 N3 C4 121.7(3) . . ? C3 N3 H3 119(2) . . ? C4 N3 H3 117(2) . . ? C13 N4 C12 122.3(3) . . ? C13 N4 H4 122(3) . . ? C12 N4 H4 114(3) . . ? C13 N5 C14 120.4(3) . . ? C13 N5 H5 113(4) . . ? C14 N5 H5 118(4) . . ? C22 N6 C21 123.3(4) . . ? C22 N6 H6 117(3) . . ? C21 N6 H6 120(3) . . ? C22 N7 C23 122.1(3) . . ? C22 N7 H7 115(2) . . ? C23 N7 H7 122(2) . . ? C37 N8 C33 111.9(3) . . ? C37 N8 C41 111.7(3) . . ? C33 N8 C41 105.4(2) . . ? C37 N8 C29 105.5(2) . . ? C33 N8 C29 111.7(3) . . ? C41 N8 C29 110.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O4 0.91(4) 2.03(4) 2.877(3) 156(3) 1 N3 H3 O4 0.83(3) 1.99(4) 2.759(4) 156(3) 1 N4 H4 O4 0.83(4) 2.12(4) 2.840(4) 145(4) 1 N5 H5 O4 0.71(4) 2.09(4) 2.766(4) 159(5) 1 N6 H6 O4 0.82(4) 2.01(4) 2.779(4) 158(3) 1 N7 H7 O4 0.87(4) 2.04(4) 2.830(4) 150(3) 1 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.16 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.464 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.044