# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Kehr, Gerald' _publ_contact_author_email kehrald@uni-muenster.de _publ_section_title ; Addition Reactions to the Intramolecular Mesityl2P-CH2-CH2-B(C6F5)2 Frustrated Lewis Pair ; loop_ _publ_author_name G.Kehr G.Erker C.Momming B.Wibbeling R.Frohlich # Attachment '- 10.cif' data_erk4925 _database_code_depnum_ccdc_archive 'CCDC 722646' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42.50 H39 B Cl2 F10 N O P' _chemical_formula_weight 882.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.5440(6) _cell_length_b 14.3430(4) _cell_length_c 22.6139(7) _cell_angle_alpha 90.00 _cell_angle_beta 122.078(1) _cell_angle_gamma 90.00 _cell_volume 8119.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7377 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3624 _exptl_absorpt_coefficient_mu 2.533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4710 _exptl_absorpt_correction_T_max 0.5701 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57011 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 67.94 _reflns_number_total 7244 _reflns_number_gt 6260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (NOnius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0996P)^2^+13.7209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7244 _refine_ls_number_parameters 556 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1821 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.049 _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 O1 O 0.15272(7) 0.74135(12) 0.02572(9) 0.0426(4) Uani 1 1 d . . . B1 B 0.11912(13) 0.6542(2) -0.00850(17) 0.0451(7) Uani 1 1 d . . . P1 P 0.21593(3) 0.65700(5) 0.15479(3) 0.0407(2) Uani 1 1 d . . . C1 C 0.16352(12) 0.5703(2) 0.11117(15) 0.0507(7) Uani 1 1 d . . . H1A H 0.1757 0.5100 0.1348 0.061 Uiso 1 1 calc R . . H1B H 0.1318 0.5894 0.1114 0.061 Uiso 1 1 calc R . . C2 C 0.15051(12) 0.5630(2) 0.03578(15) 0.0501(7) Uani 1 1 d . . . H2A H 0.1285 0.5076 0.0134 0.060 Uiso 1 1 calc R . . H2B H 0.1837 0.5560 0.0364 0.060 Uiso 1 1 calc R . . C3 C 0.19110(10) 0.75437(18) 0.09109(13) 0.0401(6) Uani 1 1 d . . . N1 N 0.21549(9) 0.83046(15) 0.11797(11) 0.0430(5) Uani 1 1 d . . . C4 C 0.20303(12) 0.91417(18) 0.07872(14) 0.0442(6) Uani 1 1 d . . . C5 C 0.24622(14) 0.9660(2) 0.08812(17) 0.0565(7) Uani 1 1 d . . . H5 H 0.2812 0.9434 0.1171 0.068 Uiso 1 1 calc R . . C6 C 0.23746(17) 1.0514(2) 0.0545(2) 0.0712(10) Uani 1 1 d . . . H6 H 0.2666 1.0858 0.0603 0.085 Uiso 1 1 calc R . . C7 C 0.18738(18) 1.0854(2) 0.0137(2) 0.0721(10) Uani 1 1 d . . . H7 H 0.1819 1.1432 -0.0087 0.087 Uiso 1 1 calc R . . C8 C 0.14460(16) 1.0355(2) 0.00503(19) 0.0661(9) Uani 1 1 d . . . H8 H 0.1100 1.0601 -0.0227 0.079 Uiso 1 1 calc R . . C9 C 0.15184(13) 0.9491(2) 0.03672(16) 0.0536(7) Uani 1 1 d . . . H9 H 0.1223 0.9148 0.0297 0.064 Uiso 1 1 calc R . . C11 C 0.27447(11) 0.59589(18) 0.16772(13) 0.0428(6) Uani 1 1 d . . . C12 C 0.29646(12) 0.5277(2) 0.22072(14) 0.0483(6) Uani 1 1 d . . . C13 C 0.33953(13) 0.4757(2) 0.23015(16) 0.0595(8) Uani 1 1 d . . . H13 H 0.3544 0.4304 0.2656 0.071 Uiso 1 1 calc R . . C14 C 0.36142(14) 0.4878(2) 0.18981(18) 0.0625(8) Uani 1 1 d . . . C15 C 0.33896(12) 0.5550(2) 0.13793(16) 0.0553(7) Uani 1 1 d . . . H15 H 0.3534 0.5638 0.1099 0.066 Uiso 1 1 calc R . . C16 C 0.29618(11) 0.6098(2) 0.12560(14) 0.0452(6) Uani 1 1 d . . . C17 C 0.27746(14) 0.5070(2) 0.26973(16) 0.0586(8) Uani 1 1 d . . . H17A H 0.2948 0.5492 0.3092 0.088 Uiso 1 1 calc R . . H17B H 0.2864 0.4432 0.2861 0.088 Uiso 1 1 calc R . . H17C H 0.2391 0.5154 0.2452 0.088 Uiso 1 1 calc R . . C18 C 0.40767(19) 0.4293(3) 0.2010(3) 0.0949(14) Uani 1 1 d . . . H18A H 0.4169 0.3842 0.2377 0.142 Uiso 1 1 calc R . . H18B H 0.4382 0.4692 0.2145 0.142 Uiso 1 1 calc R . . H18C H 0.3977 0.3969 0.1581 0.142 Uiso 1 1 calc R . . C19 C 0.27674(12) 0.6811(2) 0.06855(15) 0.0518(7) Uani 1 1 d . . . H19A H 0.2966 0.6750 0.0457 0.078 Uiso 1 1 calc R . . H19B H 0.2821 0.7431 0.0884 0.078 Uiso 1 1 calc R . . H19C H 0.2390 0.6713 0.0348 0.078 Uiso 1 1 calc R . . C21 C 0.23018(11) 0.70837(19) 0.23668(14) 0.0433(6) Uani 1 1 d . . . C22 C 0.19432(12) 0.7016(2) 0.25998(16) 0.0519(7) Uani 1 1 d . . . C23 C 0.20818(14) 0.7441(2) 0.32226(17) 0.0558(7) Uani 1 1 d . . . H23 H 0.1841 0.7405 0.3374 0.067 Uiso 1 1 calc R . . C24 C 0.25569(14) 0.7916(2) 0.36349(15) 0.0534(7) Uani 1 1 d . . . C25 C 0.29023(12) 0.7964(2) 0.34003(15) 0.0504(7) Uani 1 1 d . . . H25 H 0.3229 0.8277 0.3677 0.060 Uiso 1 1 calc R . . C26 C 0.27898(11) 0.75715(19) 0.27751(14) 0.0450(6) Uani 1 1 d . . . C27 C 0.14164(17) 0.6501(3) 0.2222(2) 0.0828(12) Uani 1 1 d . . . H27A H 0.1480 0.5845 0.2190 0.124 Uiso 1 1 calc R . . H27B H 0.1192 0.6757 0.1757 0.124 Uiso 1 1 calc R . . H27C H 0.1239 0.6570 0.2478 0.124 Uiso 1 1 calc R . . C28 C 0.26797(18) 0.8374(3) 0.43020(19) 0.0723(10) Uani 1 1 d . . . H28A H 0.3063 0.8461 0.4604 0.109 Uiso 1 1 calc R . . H28B H 0.2553 0.7983 0.4534 0.109 Uiso 1 1 calc R . . H28C H 0.2503 0.8975 0.4198 0.109 Uiso 1 1 calc R . . C29 C 0.32065(12) 0.7704(2) 0.25919(16) 0.0548(7) Uani 1 1 d . . . H29A H 0.3417 0.7140 0.2701 0.082 Uiso 1 1 calc R . . H29B H 0.3438 0.8220 0.2859 0.082 Uiso 1 1 calc R . . H29C H 0.3033 0.7839 0.2098 0.082 Uiso 1 1 calc R . . C31 C 0.06205(11) 0.6619(2) -0.01115(15) 0.0473(6) Uani 1 1 d . . . C32 C 0.05089(12) 0.7203(2) 0.02814(17) 0.0561(7) Uani 1 1 d . . . F32 F 0.08793(8) 0.78246(14) 0.07270(11) 0.0732(6) Uani 1 1 d . . . C33 C 0.00406(15) 0.7178(3) 0.0281(2) 0.0689(9) Uani 1 1 d . . . F33 F -0.00261(11) 0.7755(2) 0.06990(16) 0.1029(8) Uani 1 1 d . . . C34 C -0.03515(13) 0.6566(3) -0.0145(2) 0.0711(10) Uani 1 1 d . . . F34 F -0.08133(9) 0.6539(2) -0.01634(15) 0.1011(9) Uani 1 1 d . . . C35 C -0.02707(12) 0.5977(3) -0.05554(18) 0.0659(10) Uani 1 1 d . . . F35 F -0.06533(8) 0.53682(19) -0.09778(12) 0.0925(8) Uani 1 1 d . . . C36 C 0.02057(12) 0.6007(2) -0.05265(16) 0.0544(7) Uani 1 1 d . . . F36 F 0.02641(8) 0.53822(14) -0.09280(10) 0.0712(5) Uani 1 1 d . . . C41 C 0.10546(11) 0.6609(2) -0.08910(15) 0.0488(7) Uani 1 1 d . . . C42 C 0.11159(14) 0.5901(2) -0.12603(18) 0.0611(8) Uani 1 1 d . . . F42 F 0.13210(10) 0.50731(15) -0.09539(12) 0.0839(6) Uani 1 1 d . . . C43 C 0.09727(15) 0.5983(3) -0.1951(2) 0.0726(10) Uani 1 1 d . . . F43 F 0.10388(13) 0.5261(2) -0.22749(15) 0.1114(9) Uani 1 1 d . . . C44 C 0.07632(13) 0.6798(3) -0.22982(17) 0.0687(10) Uani 1 1 d . . . F44 F 0.06151(9) 0.6877(2) -0.29708(10) 0.0966(8) Uani 1 1 d . . . C45 C 0.07034(12) 0.7529(3) -0.19629(16) 0.0609(8) Uani 1 1 d . . . F45 F 0.05116(8) 0.83452(18) -0.22971(10) 0.0802(6) Uani 1 1 d . . . C46 C 0.08414(11) 0.7412(2) -0.12764(15) 0.0514(7) Uani 1 1 d . . . F46 F 0.07446(8) 0.81553(13) -0.09917(9) 0.0627(5) Uani 1 1 d . . . C10 C 0.0362(3) 1.0986(5) 0.1156(4) 0.147(3) Uani 1 1 d . . . H10A H 0.0519 1.1164 0.1646 0.177 Uiso 1 1 calc R . . H10B H 0.0064 1.1412 0.0872 0.177 Uiso 1 1 calc R . . Cl1 Cl 0.08342(6) 1.11527(13) 0.09464(7) 0.1209(5) Uani 1 1 d . . . Cl2 Cl 0.01139(10) 0.98937(18) 0.10477(14) 0.2009(11) Uani 1 1 d . . . C51 C 0.4355(5) 0.1761(11) 0.1634(8) 0.133(5) Uani 0.50 1 d PDU A -1 H51A H 0.4091 0.1327 0.1302 0.199 Uiso 0.50 1 calc PR A -1 H51B H 0.4419 0.2242 0.1385 0.199 Uiso 0.50 1 calc PR A -1 H51C H 0.4226 0.2046 0.1907 0.199 Uiso 0.50 1 calc PR A -1 C52 C 0.4873(6) 0.1244(10) 0.2118(7) 0.157(6) Uani 0.50 1 d PDU A -1 H52A H 0.4839 0.0794 0.2418 0.188 Uiso 0.50 1 calc PR A -1 H52B H 0.5019 0.0940 0.1867 0.188 Uiso 0.50 1 calc PR A -1 C53 C 0.5174(6) 0.2083(11) 0.2498(7) 0.200(9) Uani 0.50 1 d PDU A -1 H53A H 0.4954 0.2643 0.2297 0.240 Uiso 0.50 1 calc PR A -1 H53B H 0.5496 0.2149 0.2479 0.240 Uiso 0.50 1 calc PR A -1 C54 C 0.5317(5) 0.1946(16) 0.3229(7) 0.194(8) Uani 0.50 1 d PDU A -1 H54A H 0.5212 0.1317 0.3281 0.233 Uiso 0.50 1 calc PR A -1 H54B H 0.5121 0.2396 0.3337 0.233 Uiso 0.50 1 calc PR A -1 C55 C 0.5928(4) 0.2077(6) 0.3748(5) 0.084(2) Uani 0.50 1 d PDU A -1 H55A H 0.6020 0.1907 0.4214 0.126 Uiso 0.50 1 calc PR A -1 H55B H 0.6023 0.2723 0.3745 0.126 Uiso 0.50 1 calc PR A -1 H55C H 0.6122 0.1681 0.3609 0.126 Uiso 0.50 1 calc PR A -1 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 O1 0.0423(9) 0.0417(10) 0.0382(9) -0.0044(7) 0.0176(8) -0.0099(7) B1 0.0450(16) 0.0426(16) 0.0447(16) -0.0104(13) 0.0219(14) -0.0118(13) P1 0.0421(4) 0.0409(4) 0.0390(4) -0.0019(3) 0.0214(3) -0.0111(3) C1 0.0498(15) 0.0448(15) 0.0503(15) 0.0012(12) 0.0216(13) -0.0143(12) C2 0.0467(15) 0.0418(15) 0.0528(16) -0.0080(12) 0.0203(13) -0.0109(12) C3 0.0410(13) 0.0421(14) 0.0392(13) -0.0040(10) 0.0227(11) -0.0088(11) N1 0.0508(13) 0.0406(12) 0.0399(11) -0.0065(9) 0.0256(10) -0.0126(10) C4 0.0607(16) 0.0371(13) 0.0408(13) -0.0081(11) 0.0311(13) -0.0113(12) C5 0.0663(19) 0.0482(16) 0.0592(18) -0.0052(13) 0.0361(16) -0.0163(14) C6 0.091(3) 0.0546(19) 0.077(2) -0.0053(17) 0.051(2) -0.0266(19) C7 0.108(3) 0.0432(17) 0.072(2) 0.0030(16) 0.052(2) -0.0085(18) C8 0.083(2) 0.0506(18) 0.065(2) 0.0029(15) 0.0394(19) 0.0070(17) C9 0.0627(18) 0.0461(16) 0.0565(17) -0.0015(13) 0.0347(15) -0.0038(13) C11 0.0460(14) 0.0406(14) 0.0371(13) -0.0036(10) 0.0188(11) -0.0091(11) C12 0.0525(16) 0.0433(15) 0.0402(14) -0.0002(11) 0.0187(12) -0.0077(12) C13 0.0616(19) 0.0526(17) 0.0491(17) 0.0064(13) 0.0192(15) 0.0034(14) C14 0.0584(18) 0.0606(19) 0.0609(19) -0.0029(15) 0.0265(16) 0.0065(15) C15 0.0539(17) 0.0592(18) 0.0545(17) -0.0065(14) 0.0299(14) -0.0026(14) C16 0.0463(14) 0.0468(15) 0.0411(14) -0.0052(11) 0.0223(12) -0.0081(12) C17 0.072(2) 0.0524(17) 0.0468(16) 0.0088(13) 0.0283(15) -0.0065(15) C18 0.085(3) 0.095(3) 0.105(3) 0.012(3) 0.050(3) 0.033(2) C19 0.0575(17) 0.0585(17) 0.0494(16) 0.0026(13) 0.0351(14) -0.0020(14) C21 0.0468(14) 0.0449(14) 0.0410(13) 0.0019(11) 0.0251(12) -0.0065(11) C22 0.0577(17) 0.0541(17) 0.0531(16) 0.0029(13) 0.0358(14) -0.0067(13) C23 0.072(2) 0.0549(17) 0.0578(17) 0.0075(14) 0.0462(17) 0.0025(15) C24 0.074(2) 0.0423(15) 0.0462(15) 0.0032(12) 0.0336(15) 0.0042(14) C25 0.0575(17) 0.0447(15) 0.0426(14) -0.0030(12) 0.0223(13) -0.0045(12) C26 0.0487(15) 0.0432(14) 0.0403(14) 0.0002(11) 0.0218(12) -0.0054(11) C27 0.077(2) 0.112(3) 0.086(3) -0.021(2) 0.061(2) -0.037(2) C28 0.109(3) 0.061(2) 0.058(2) -0.0037(15) 0.051(2) 0.0067(19) C29 0.0466(15) 0.0644(19) 0.0509(16) -0.0108(14) 0.0243(13) -0.0174(14) C31 0.0446(15) 0.0479(15) 0.0447(15) 0.0015(12) 0.0205(13) -0.0086(12) C32 0.0503(16) 0.0598(18) 0.0623(18) -0.0024(15) 0.0327(15) -0.0107(14) F32 0.0741(12) 0.0754(13) 0.0881(14) -0.0319(11) 0.0554(11) -0.0253(10) C33 0.066(2) 0.074(2) 0.083(2) 0.0063(19) 0.050(2) 0.0032(18) F33 0.1008(18) 0.1118(19) 0.141(2) -0.0200(17) 0.0940(18) -0.0057(15) C34 0.0456(17) 0.087(3) 0.081(2) 0.022(2) 0.0345(18) -0.0016(17) F34 0.0554(12) 0.134(2) 0.125(2) 0.0230(17) 0.0555(14) -0.0051(13) C35 0.0421(16) 0.078(2) 0.0592(19) 0.0161(17) 0.0143(14) -0.0187(15) F35 0.0583(12) 0.1173(19) 0.0774(14) 0.0022(13) 0.0194(11) -0.0451(12) C36 0.0478(16) 0.0589(18) 0.0465(16) 0.0022(13) 0.0183(13) -0.0137(13) F36 0.0664(12) 0.0707(12) 0.0666(12) -0.0203(10) 0.0288(10) -0.0307(10) C41 0.0411(14) 0.0566(17) 0.0497(16) -0.0142(13) 0.0249(13) -0.0125(12) C42 0.0608(18) 0.0593(19) 0.064(2) -0.0162(16) 0.0341(16) -0.0089(15) F42 0.1062(17) 0.0638(13) 0.0846(15) -0.0202(11) 0.0526(13) 0.0004(12) C43 0.067(2) 0.097(3) 0.064(2) -0.035(2) 0.0417(19) -0.018(2) F43 0.136(2) 0.122(2) 0.0942(17) -0.0487(16) 0.0729(17) -0.0085(18) C44 0.0506(18) 0.111(3) 0.0456(17) -0.0140(19) 0.0266(15) -0.0170(19) F44 0.0775(14) 0.170(3) 0.0469(11) -0.0194(13) 0.0359(10) -0.0249(15) C45 0.0411(15) 0.090(2) 0.0470(16) -0.0018(17) 0.0206(13) -0.0105(15) F45 0.0624(12) 0.1106(17) 0.0553(11) 0.0219(11) 0.0229(10) 0.0014(11) C46 0.0416(14) 0.0646(19) 0.0456(15) -0.0081(13) 0.0215(12) -0.0071(13) F46 0.0665(11) 0.0640(11) 0.0542(10) 0.0026(8) 0.0297(9) 0.0067(9) C10 0.186(7) 0.123(5) 0.175(7) 0.010(5) 0.124(6) 0.054(5) Cl1 0.1013(9) 0.1615(14) 0.0924(8) 0.0030(8) 0.0463(7) 0.0278(9) Cl2 0.1566(18) 0.171(2) 0.189(2) -0.0157(17) 0.0337(16) -0.0573(15) C51 0.138(8) 0.140(9) 0.155(9) -0.028(7) 0.102(7) -0.040(7) C52 0.157(9) 0.157(9) 0.156(9) -0.025(7) 0.083(8) -0.009(8) C53 0.169(12) 0.194(11) 0.236(12) -0.015(9) 0.108(9) -0.004(8) C54 0.223(12) 0.211(13) 0.182(11) -0.008(8) 0.131(9) -0.001(9) C55 0.121(7) 0.057(4) 0.101(6) 0.015(4) 0.078(5) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.313(3) . ? O1 B1 1.527(3) . ? B1 C2 1.609(4) . ? B1 C41 1.647(4) . ? B1 C31 1.659(4) . ? P1 C1 1.815(3) . ? P1 C11 1.819(3) . ? P1 C21 1.823(3) . ? P1 C3 1.855(3) . ? C1 C2 1.539(4) . ? C3 N1 1.271(3) . ? N1 C4 1.421(3) . ? C4 C9 1.384(4) . ? C4 C5 1.392(4) . ? C5 C6 1.391(5) . ? C6 C7 1.352(6) . ? C7 C8 1.372(5) . ? C8 C9 1.390(5) . ? C11 C12 1.410(4) . ? C11 C16 1.417(4) . ? C12 C13 1.390(5) . ? C12 C17 1.514(4) . ? C13 C14 1.381(5) . ? C14 C15 1.385(5) . ? C14 C18 1.506(5) . ? C15 C16 1.385(4) . ? C16 C19 1.501(4) . ? C21 C22 1.415(4) . ? C21 C26 1.417(4) . ? C22 C23 1.382(4) . ? C22 C27 1.512(5) . ? C23 C24 1.383(5) . ? C24 C25 1.379(4) . ? C24 C28 1.503(4) . ? C25 C26 1.388(4) . ? C26 C29 1.505(4) . ? C31 C32 1.382(4) . ? C31 C36 1.390(4) . ? C32 F32 1.355(4) . ? C32 C33 1.384(5) . ? C33 F33 1.347(4) . ? C33 C34 1.362(6) . ? C34 F34 1.343(4) . ? C34 C35 1.366(6) . ? C35 F35 1.344(4) . ? C35 C36 1.374(5) . ? C36 F36 1.351(4) . ? C41 C46 1.379(4) . ? C41 C42 1.385(4) . ? C42 F42 1.346(4) . ? C42 C43 1.389(5) . ? C43 F43 1.342(4) . ? C43 C44 1.360(6) . ? C44 F44 1.346(4) . ? C44 C45 1.359(5) . ? C45 F45 1.344(4) . ? C45 C46 1.390(4) . ? C46 F46 1.352(4) . ? C10 Cl2 1.692(8) . ? C10 Cl1 1.711(7) . ? C51 C52 1.518(10) . ? C52 C53 1.472(9) . ? C53 C54 1.485(10) . ? C54 C55 1.556(10) . ? 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 C3 O1 B1 128.8(2) . . ? O1 B1 C2 110.2(2) . . ? O1 B1 C41 103.0(2) . . ? C2 B1 C41 117.2(2) . . ? O1 B1 C31 109.8(2) . . ? C2 B1 C31 108.4(2) . . ? C41 B1 C31 108.0(2) . . ? C1 P1 C11 102.78(14) . . ? C1 P1 C21 119.95(13) . . ? C11 P1 C21 110.16(12) . . ? C1 P1 C3 102.85(12) . . ? C11 P1 C3 115.96(12) . . ? C21 P1 C3 105.51(12) . . ? C2 C1 P1 106.73(19) . . ? C1 C2 B1 110.9(2) . . ? N1 C3 O1 126.3(2) . . ? N1 C3 P1 112.65(19) . . ? O1 C3 P1 121.05(18) . . ? C3 N1 C4 122.3(2) . . ? C9 C4 C5 119.4(3) . . ? C9 C4 N1 124.1(2) . . ? C5 C4 N1 116.3(3) . . ? C6 C5 C4 119.8(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 C8 120.0(3) . . ? C7 C8 C9 120.9(4) . . ? C4 C9 C8 119.3(3) . . ? C12 C11 C16 120.0(3) . . ? C12 C11 P1 116.1(2) . . ? C16 C11 P1 123.7(2) . . ? C13 C12 C11 118.2(3) . . ? C13 C12 C17 116.6(3) . . ? C11 C12 C17 125.1(3) . . ? C14 C13 C12 122.9(3) . . ? C13 C14 C15 117.7(3) . . ? C13 C14 C18 121.3(3) . . ? C15 C14 C18 120.9(4) . . ? C16 C15 C14 122.7(3) . . ? C15 C16 C11 118.4(3) . . ? C15 C16 C19 116.8(3) . . ? C11 C16 C19 124.8(3) . . ? C22 C21 C26 119.7(3) . . ? C22 C21 P1 122.4(2) . . ? C26 C21 P1 117.9(2) . . ? C23 C22 C21 118.3(3) . . ? C23 C22 C27 116.7(3) . . ? C21 C22 C27 125.0(3) . . ? C22 C23 C24 123.3(3) . . ? C25 C24 C23 117.3(3) . . ? C25 C24 C28 122.0(3) . . ? C23 C24 C28 120.6(3) . . ? C24 C25 C26 123.1(3) . . ? C25 C26 C21 118.3(3) . . ? C25 C26 C29 116.2(2) . . ? C21 C26 C29 125.5(2) . . ? C32 C31 C36 113.0(3) . . ? C32 C31 B1 127.0(2) . . ? C36 C31 B1 119.8(3) . . ? F32 C32 C31 120.2(3) . . ? F32 C32 C33 115.5(3) . . ? C31 C32 C33 124.3(3) . . ? F33 C33 C34 120.4(3) . . ? F33 C33 C32 120.2(3) . . ? C34 C33 C32 119.5(4) . . ? F34 C34 C33 120.5(4) . . ? F34 C34 C35 120.2(4) . . ? C33 C34 C35 119.3(3) . . ? F35 C35 C34 120.0(3) . . ? F35 C35 C36 120.5(4) . . ? C34 C35 C36 119.5(3) . . ? F36 C36 C35 116.1(3) . . ? F36 C36 C31 119.4(3) . . ? C35 C36 C31 124.4(3) . . ? C46 C41 C42 113.1(3) . . ? C46 C41 B1 120.6(3) . . ? C42 C41 B1 126.2(3) . . ? F42 C42 C41 120.2(3) . . ? F42 C42 C43 116.0(3) . . ? C41 C42 C43 123.8(3) . . ? F43 C43 C44 120.1(4) . . ? F43 C43 C42 120.2(4) . . ? C44 C43 C42 119.7(3) . . ? F44 C44 C45 120.4(4) . . ? F44 C44 C43 120.0(4) . . ? C45 C44 C43 119.6(3) . . ? F45 C45 C44 119.9(3) . . ? F45 C45 C46 121.2(3) . . ? C44 C45 C46 118.8(4) . . ? F46 C46 C41 119.9(3) . . ? F46 C46 C45 115.2(3) . . ? C41 C46 C45 124.8(3) . . ? Cl2 C10 Cl1 116.4(4) . . ? C53 C52 C51 95.0(9) . . ? C52 C53 C54 105.6(12) . . ? C53 C54 C55 110.8(11) . . ? 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 C3 O1 B1 C2 -23.7(4) . . . . ? C3 O1 B1 C41 -149.5(2) . . . . ? C3 O1 B1 C31 95.7(3) . . . . ? C11 P1 C1 C2 -73.7(2) . . . . ? C21 P1 C1 C2 163.69(19) . . . . ? C3 P1 C1 C2 47.1(2) . . . . ? P1 C1 C2 B1 -71.9(3) . . . . ? O1 B1 C2 C1 58.9(3) . . . . ? C41 B1 C2 C1 176.2(2) . . . . ? C31 B1 C2 C1 -61.3(3) . . . . ? B1 O1 C3 N1 -175.0(3) . . . . ? B1 O1 C3 P1 5.8(4) . . . . ? C1 P1 C3 N1 164.3(2) . . . . ? C11 P1 C3 N1 -84.4(2) . . . . ? C21 P1 C3 N1 37.8(2) . . . . ? C1 P1 C3 O1 -16.4(2) . . . . ? C11 P1 C3 O1 94.9(2) . . . . ? C21 P1 C3 O1 -142.9(2) . . . . ? O1 C3 N1 C4 0.7(4) . . . . ? P1 C3 N1 C4 180.0(2) . . . . ? C3 N1 C4 C9 49.7(4) . . . . ? C3 N1 C4 C5 -135.0(3) . . . . ? C9 C4 C5 C6 -0.9(4) . . . . ? N1 C4 C5 C6 -176.4(3) . . . . ? C4 C5 C6 C7 1.2(5) . . . . ? C5 C6 C7 C8 -0.1(6) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C5 C4 C9 C8 -0.3(4) . . . . ? N1 C4 C9 C8 174.8(3) . . . . ? C7 C8 C9 C4 1.4(5) . . . . ? C1 P1 C11 C12 -74.4(2) . . . . ? C21 P1 C11 C12 54.6(2) . . . . ? C3 P1 C11 C12 174.28(19) . . . . ? C1 P1 C11 C16 102.0(2) . . . . ? C21 P1 C11 C16 -129.1(2) . . . . ? C3 P1 C11 C16 -9.4(3) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? P1 C11 C12 C13 176.7(2) . . . . ? C16 C11 C12 C17 179.1(3) . . . . ? P1 C11 C12 C17 -4.4(4) . . . . ? C11 C12 C13 C14 -0.3(5) . . . . ? C17 C12 C13 C14 -179.3(3) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C12 C13 C14 C18 -179.2(4) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C18 C14 C15 C16 179.5(3) . . . . ? C14 C15 C16 C11 -0.3(4) . . . . ? C14 C15 C16 C19 178.8(3) . . . . ? C12 C11 C16 C15 0.1(4) . . . . ? P1 C11 C16 C15 -176.2(2) . . . . ? C12 C11 C16 C19 -179.0(3) . . . . ? P1 C11 C16 C19 4.8(4) . . . . ? C1 P1 C21 C22 -15.9(3) . . . . ? C11 P1 C21 C22 -134.8(2) . . . . ? C3 P1 C21 C22 99.3(3) . . . . ? C1 P1 C21 C26 164.6(2) . . . . ? C11 P1 C21 C26 45.7(2) . . . . ? C3 P1 C21 C26 -80.2(2) . . . . ? C26 C21 C22 C23 0.5(4) . . . . ? P1 C21 C22 C23 -179.0(2) . . . . ? C26 C21 C22 C27 -178.7(3) . . . . ? P1 C21 C22 C27 1.8(5) . . . . ? C21 C22 C23 C24 -1.1(5) . . . . ? C27 C22 C23 C24 178.2(3) . . . . ? C22 C23 C24 C25 0.4(5) . . . . ? C22 C23 C24 C28 179.1(3) . . . . ? C23 C24 C25 C26 0.8(4) . . . . ? C28 C24 C25 C26 -177.8(3) . . . . ? C24 C25 C26 C21 -1.3(4) . . . . ? C24 C25 C26 C29 178.9(3) . . . . ? C22 C21 C26 C25 0.6(4) . . . . ? P1 C21 C26 C25 -179.9(2) . . . . ? C22 C21 C26 C29 -179.6(3) . . . . ? P1 C21 C26 C29 -0.1(4) . . . . ? O1 B1 C31 C32 -18.4(4) . . . . ? C2 B1 C31 C32 102.0(3) . . . . ? C41 B1 C31 C32 -130.0(3) . . . . ? O1 B1 C31 C36 166.5(2) . . . . ? C2 B1 C31 C36 -73.0(3) . . . . ? C41 B1 C31 C36 54.9(3) . . . . ? C36 C31 C32 F32 178.3(3) . . . . ? B1 C31 C32 F32 3.0(5) . . . . ? C36 C31 C32 C33 1.4(5) . . . . ? B1 C31 C32 C33 -173.9(3) . . . . ? F32 C32 C33 F33 0.8(5) . . . . ? C31 C32 C33 F33 177.8(3) . . . . ? F32 C32 C33 C34 -179.3(3) . . . . ? C31 C32 C33 C34 -2.2(6) . . . . ? F33 C33 C34 F34 1.1(6) . . . . ? C32 C33 C34 F34 -178.8(3) . . . . ? F33 C33 C34 C35 -178.9(3) . . . . ? C32 C33 C34 C35 1.2(6) . . . . ? F34 C34 C35 F35 -0.1(5) . . . . ? C33 C34 C35 F35 179.9(3) . . . . ? F34 C34 C35 C36 -179.5(3) . . . . ? C33 C34 C35 C36 0.5(5) . . . . ? F35 C35 C36 F36 -1.6(4) . . . . ? C34 C35 C36 F36 177.7(3) . . . . ? F35 C35 C36 C31 179.3(3) . . . . ? C34 C35 C36 C31 -1.4(5) . . . . ? C32 C31 C36 F36 -178.6(3) . . . . ? B1 C31 C36 F36 -2.9(4) . . . . ? C32 C31 C36 C35 0.4(4) . . . . ? B1 C31 C36 C35 176.1(3) . . . . ? O1 B1 C41 C46 -51.4(3) . . . . ? C2 B1 C41 C46 -172.6(3) . . . . ? C31 B1 C41 C46 64.7(3) . . . . ? O1 B1 C41 C42 130.8(3) . . . . ? C2 B1 C41 C42 9.7(4) . . . . ? C31 B1 C41 C42 -113.1(3) . . . . ? C46 C41 C42 F42 179.8(3) . . . . ? B1 C41 C42 F42 -2.3(5) . . . . ? C46 C41 C42 C43 -0.7(5) . . . . ? B1 C41 C42 C43 177.1(3) . . . . ? F42 C42 C43 F43 0.3(5) . . . . ? C41 C42 C43 F43 -179.2(3) . . . . ? F42 C42 C43 C44 -179.9(3) . . . . ? C41 C42 C43 C44 0.6(5) . . . . ? F43 C43 C44 F44 0.9(5) . . . . ? C42 C43 C44 F44 -178.8(3) . . . . ? F43 C43 C44 C45 -179.3(3) . . . . ? C42 C43 C44 C45 1.0(5) . . . . ? F44 C44 C45 F45 -2.2(5) . . . . ? C43 C44 C45 F45 178.0(3) . . . . ? F44 C44 C45 C46 177.5(3) . . . . ? C43 C44 C45 C46 -2.3(5) . . . . ? C42 C41 C46 F46 178.2(3) . . . . ? B1 C41 C46 F46 0.2(4) . . . . ? C42 C41 C46 C45 -0.7(4) . . . . ? B1 C41 C46 C45 -178.7(3) . . . . ? F45 C45 C46 F46 3.0(4) . . . . ? C44 C45 C46 F46 -176.7(3) . . . . ? F45 C45 C46 C41 -178.1(3) . . . . ? C44 C45 C46 C41 2.2(5) . . . . ? C51 C52 C53 C54 116.3(14) . . . . ? C52 C53 C54 C55 127.1(14) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.94 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.717 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.060 # Attachment '- 9.cif' data_erk4849 _database_code_depnum_ccdc_archive 'CCDC 722647' #TrackingRef '- 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H32 B F10 O P' _chemical_formula_weight 748.43 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 11.4602(3) _cell_length_b 13.8298(4) _cell_length_c 21.8599(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3464.63(17) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4360 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 1.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6668 _exptl_absorpt_correction_T_max 0.8096 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13725 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 67.50 _reflns_number_total 5824 _reflns_number_gt 5536 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 200)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+1.3397P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 5824 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 P1 P 0.69057(5) 0.29799(4) 0.86889(3) 0.03058(14) Uani 1 1 d . . . B1 B 0.8901(2) 0.4659(2) 0.88167(12) 0.0320(6) Uani 1 1 d . . . O1 O 0.84267(14) 0.43111(12) 0.82176(7) 0.0324(4) Uani 1 1 d . . . C1 C 0.7520(2) 0.34370(19) 0.94069(11) 0.0357(6) Uani 1 1 d . . . H1A H 0.7041 0.3973 0.9558 0.043 Uiso 1 1 calc R . . H1B H 0.7509 0.2923 0.9715 0.043 Uiso 1 1 calc R . . C2 C 0.8785(2) 0.37880(18) 0.93113(11) 0.0349(5) Uani 1 1 d . . . H2A H 0.9263 0.3241 0.9174 0.042 Uiso 1 1 calc R . . H2B H 0.9098 0.4009 0.9704 0.042 Uiso 1 1 calc R . . C3 C 0.7258(2) 0.40882(18) 0.81937(11) 0.0315(5) Uani 1 1 d . . . H3 H 0.6871 0.4633 0.8406 0.038 Uiso 1 1 calc R . . C4 C 0.6788(2) 0.41299(17) 0.75504(11) 0.0322(5) Uani 1 1 d . . . C5 C 0.7548(2) 0.4141(2) 0.70546(12) 0.0408(6) Uani 1 1 d . . . H5 H 0.8357 0.4101 0.7121 0.049 Uiso 1 1 calc R . . C6 C 0.7126(3) 0.4210(2) 0.64672(12) 0.0491(7) Uani 1 1 d . . . H6 H 0.7648 0.4208 0.6136 0.059 Uiso 1 1 calc R . . C7 C 0.5935(3) 0.4284(2) 0.63582(13) 0.0483(7) Uani 1 1 d . . . H7 H 0.5648 0.4318 0.5956 0.058 Uiso 1 1 calc R . . C8 C 0.5176(2) 0.4308(2) 0.68513(12) 0.0416(6) Uani 1 1 d . . . H8 H 0.4370 0.4371 0.6783 0.050 Uiso 1 1 calc R . . C9 C 0.5593(2) 0.42409(18) 0.74411(12) 0.0361(5) Uani 1 1 d . . . H9 H 0.5070 0.4270 0.7772 0.043 Uiso 1 1 calc R . . C11 C 0.5325(2) 0.28145(18) 0.86699(11) 0.0343(5) Uani 1 1 d . . . C12 C 0.4899(2) 0.21958(18) 0.82128(12) 0.0374(6) Uani 1 1 d . . . C13 C 0.3720(2) 0.1940(2) 0.82206(14) 0.0451(6) Uani 1 1 d . . . H13 H 0.3439 0.1511 0.7921 0.054 Uiso 1 1 calc R . . C14 C 0.2957(2) 0.2293(2) 0.86505(14) 0.0475(7) Uani 1 1 d . . . C15 C 0.3382(2) 0.2956(2) 0.90686(13) 0.0470(7) Uani 1 1 d . . . H15 H 0.2857 0.3235 0.9348 0.056 Uiso 1 1 calc R . . C16 C 0.4549(2) 0.3232(2) 0.90953(12) 0.0400(6) Uani 1 1 d . . . C17 C 0.5619(2) 0.1792(2) 0.76931(13) 0.0446(7) Uani 1 1 d . . . H17A H 0.5970 0.1186 0.7819 0.067 Uiso 1 1 calc R . . H17B H 0.6227 0.2250 0.7586 0.067 Uiso 1 1 calc R . . H17C H 0.5121 0.1682 0.7341 0.067 Uiso 1 1 calc R . . C18 C 0.1694(3) 0.1985(3) 0.8652(2) 0.0745(10) Uani 1 1 d . . . H18A H 0.1368 0.2070 0.8246 0.112 Uiso 1 1 calc R . . H18B H 0.1262 0.2377 0.8942 0.112 Uiso 1 1 calc R . . H18C H 0.1640 0.1310 0.8769 0.112 Uiso 1 1 calc R . . C19 C 0.4861(3) 0.3966(3) 0.95814(15) 0.0592(9) Uani 1 1 d . . . H19A H 0.4153 0.4223 0.9762 0.089 Uiso 1 1 calc R . . H19B H 0.5305 0.4488 0.9398 0.089 Uiso 1 1 calc R . . H19C H 0.5327 0.3657 0.9896 0.089 Uiso 1 1 calc R . . C21 C 0.7591(2) 0.17870(17) 0.86323(12) 0.0332(5) Uani 1 1 d . . . C22 C 0.8494(2) 0.15572(18) 0.82209(12) 0.0354(5) Uani 1 1 d . . . C23 C 0.9062(2) 0.06791(19) 0.82825(13) 0.0412(6) Uani 1 1 d . . . H23 H 0.9676 0.0535 0.8013 0.049 Uiso 1 1 calc R . . C24 C 0.8765(2) 0.00043(18) 0.87234(14) 0.0440(6) Uani 1 1 d . . . C25 C 0.7831(2) 0.0223(2) 0.91053(13) 0.0429(6) Uani 1 1 d . . . H25 H 0.7595 -0.0238 0.9396 0.051 Uiso 1 1 calc R . . C26 C 0.7234(2) 0.10976(18) 0.90742(12) 0.0363(6) Uani 1 1 d . . . C27 C 0.8838(2) 0.22050(19) 0.77005(13) 0.0437(6) Uani 1 1 d . . . H27A H 0.9549 0.1964 0.7515 0.066 Uiso 1 1 calc R . . H27B H 0.8967 0.2855 0.7853 0.066 Uiso 1 1 calc R . . H27C H 0.8219 0.2215 0.7398 0.066 Uiso 1 1 calc R . . C28 C 0.9422(3) -0.0931(3) 0.87850(18) 0.0662(9) Uani 1 1 d . . . H28A H 0.9393 -0.1280 0.8400 0.099 Uiso 1 1 calc R . . H28B H 0.9068 -0.1321 0.9104 0.099 Uiso 1 1 calc R . . H28C H 1.0228 -0.0797 0.8891 0.099 Uiso 1 1 calc R . . C29 C 0.6211(3) 0.1201(2) 0.95073(13) 0.0445(6) Uani 1 1 d . . . H29A H 0.5490 0.1087 0.9287 0.067 Uiso 1 1 calc R . . H29B H 0.6204 0.1850 0.9677 0.067 Uiso 1 1 calc R . . H29C H 0.6285 0.0734 0.9836 0.067 Uiso 1 1 calc R . . C31 C 1.0299(2) 0.49311(17) 0.87218(12) 0.0337(5) Uani 1 1 d . . . C32 C 1.0887(2) 0.54893(19) 0.91521(12) 0.0379(6) Uani 1 1 d . . . F32 F 1.03068(14) 0.58135(13) 0.96521(7) 0.0522(4) Uani 1 1 d . . . C33 C 1.2056(2) 0.5731(2) 0.91156(13) 0.0433(6) Uani 1 1 d . . . F33 F 1.25676(15) 0.62602(14) 0.95568(8) 0.0616(5) Uani 1 1 d . . . C34 C 1.2697(2) 0.5411(2) 0.86259(14) 0.0435(6) Uani 1 1 d . . . F34 F 1.38463(14) 0.56224(14) 0.85877(9) 0.0621(5) Uani 1 1 d . . . C35 C 1.2176(2) 0.4856(2) 0.81907(13) 0.0423(6) Uani 1 1 d . . . F35 F 1.28021(14) 0.45205(15) 0.77156(8) 0.0624(5) Uani 1 1 d . . . C36 C 1.1005(2) 0.46235(18) 0.82435(12) 0.0370(6) Uani 1 1 d . . . F36 F 1.05775(13) 0.40512(13) 0.77971(8) 0.0514(4) Uani 1 1 d . . . C41 C 0.8173(2) 0.56688(17) 0.89839(11) 0.0327(5) Uani 1 1 d . . . C42 C 0.7636(2) 0.58978(18) 0.95345(11) 0.0365(6) Uani 1 1 d . . . F42 F 0.77666(16) 0.53197(11) 1.00287(7) 0.0505(4) Uani 1 1 d . . . C43 C 0.6944(3) 0.6705(2) 0.96285(12) 0.0446(6) Uani 1 1 d . . . F43 F 0.64321(19) 0.68536(13) 1.01681(8) 0.0664(5) Uani 1 1 d . . . C44 C 0.6778(3) 0.7347(2) 0.91585(14) 0.0489(7) Uani 1 1 d . . . F44 F 0.6130(2) 0.81389(14) 0.92395(9) 0.0761(6) Uani 1 1 d . . . C45 C 0.7315(3) 0.71761(19) 0.86037(13) 0.0464(7) Uani 1 1 d . . . F45 F 0.7180(2) 0.78059(13) 0.81470(8) 0.0716(6) Uani 1 1 d . . . C46 C 0.7996(2) 0.63583(18) 0.85335(11) 0.0369(6) Uani 1 1 d . . . F46 F 0.84979(15) 0.62560(12) 0.79794(7) 0.0511(4) 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 P1 0.0280(3) 0.0357(3) 0.0281(3) -0.0001(3) 0.0023(2) -0.0022(2) B1 0.0306(13) 0.0370(13) 0.0284(14) -0.0019(11) -0.0012(11) -0.0003(12) O1 0.0255(8) 0.0418(9) 0.0299(8) -0.0028(7) 0.0007(7) -0.0031(7) C1 0.0364(13) 0.0411(13) 0.0295(12) 0.0009(10) -0.0027(11) -0.0032(11) C2 0.0322(12) 0.0393(13) 0.0332(13) -0.0024(11) -0.0042(11) -0.0003(11) C3 0.0283(11) 0.0345(12) 0.0318(12) 0.0006(10) -0.0004(10) -0.0027(10) C4 0.0310(12) 0.0339(11) 0.0318(12) -0.0010(10) -0.0004(11) -0.0004(10) C5 0.0294(12) 0.0577(16) 0.0354(13) 0.0027(12) 0.0002(11) 0.0014(12) C6 0.0422(15) 0.076(2) 0.0295(13) 0.0055(13) 0.0041(11) 0.0011(14) C7 0.0477(16) 0.0617(17) 0.0356(14) 0.0035(14) -0.0107(13) -0.0027(13) C8 0.0320(13) 0.0527(16) 0.0402(14) 0.0054(13) -0.0093(11) -0.0006(12) C9 0.0292(11) 0.0405(13) 0.0385(13) 0.0006(11) 0.0018(11) -0.0006(10) C11 0.0274(11) 0.0417(13) 0.0339(12) 0.0048(12) 0.0008(11) -0.0019(10) C12 0.0332(12) 0.0401(14) 0.0389(13) 0.0061(12) 0.0003(11) -0.0024(11) C13 0.0376(14) 0.0453(14) 0.0523(16) 0.0010(14) -0.0073(13) -0.0044(13) C14 0.0322(13) 0.0535(16) 0.0568(17) 0.0098(14) -0.0011(13) -0.0027(12) C15 0.0342(13) 0.0604(16) 0.0465(15) 0.0078(14) 0.0073(12) 0.0063(13) C16 0.0338(13) 0.0498(16) 0.0365(13) 0.0032(12) 0.0079(11) 0.0024(11) C17 0.0408(14) 0.0497(16) 0.0434(15) -0.0100(13) -0.0014(12) -0.0031(12) C18 0.0343(15) 0.092(2) 0.097(3) 0.002(2) 0.0046(17) -0.0088(17) C19 0.0395(15) 0.084(2) 0.0541(18) -0.0230(17) 0.0085(14) 0.0092(16) C21 0.0284(11) 0.0349(12) 0.0363(12) -0.0034(11) -0.0009(10) -0.0006(9) C22 0.0287(11) 0.0371(12) 0.0405(14) -0.0063(11) 0.0000(11) -0.0046(10) C23 0.0293(12) 0.0445(15) 0.0498(15) -0.0050(13) 0.0026(12) -0.0011(11) C24 0.0361(13) 0.0419(13) 0.0540(16) 0.0000(14) -0.0057(14) 0.0024(11) C25 0.0425(15) 0.0419(14) 0.0442(15) 0.0080(12) -0.0051(13) -0.0036(12) C26 0.0329(12) 0.0406(13) 0.0353(13) -0.0004(11) -0.0035(11) -0.0050(11) C27 0.0387(13) 0.0440(14) 0.0484(16) -0.0041(13) 0.0109(13) -0.0008(12) C28 0.0570(19) 0.0592(19) 0.082(3) 0.0150(19) 0.0039(19) 0.0126(16) C29 0.0440(15) 0.0457(14) 0.0440(15) 0.0056(13) 0.0061(13) -0.0066(13) C31 0.0318(12) 0.0351(12) 0.0341(12) 0.0054(11) -0.0016(11) -0.0010(10) C32 0.0355(13) 0.0438(14) 0.0345(13) 0.0006(12) 0.0000(12) -0.0005(11) F32 0.0431(9) 0.0699(11) 0.0435(9) -0.0167(8) -0.0018(7) -0.0056(8) C33 0.0387(14) 0.0491(15) 0.0421(14) 0.0023(12) -0.0114(12) -0.0080(12) F33 0.0490(9) 0.0760(12) 0.0598(11) -0.0125(9) -0.0123(9) -0.0185(9) C34 0.0302(12) 0.0498(14) 0.0503(16) 0.0123(14) -0.0007(13) -0.0068(11) F34 0.0304(7) 0.0856(12) 0.0704(11) 0.0080(10) -0.0032(8) -0.0163(8) C35 0.0342(14) 0.0513(15) 0.0414(14) 0.0021(13) 0.0044(12) 0.0002(12) F35 0.0367(9) 0.0905(13) 0.0600(11) -0.0139(10) 0.0156(8) -0.0041(9) C36 0.0333(12) 0.0384(13) 0.0391(13) -0.0010(12) -0.0022(12) -0.0010(11) F36 0.0386(8) 0.0659(10) 0.0496(9) -0.0203(8) 0.0083(7) -0.0091(8) C41 0.0305(12) 0.0339(12) 0.0339(12) -0.0018(10) -0.0030(11) -0.0045(10) C42 0.0422(13) 0.0369(13) 0.0305(12) -0.0007(11) -0.0030(11) -0.0019(11) F42 0.0772(12) 0.0455(8) 0.0289(7) 0.0006(7) 0.0044(8) 0.0057(8) C43 0.0483(15) 0.0477(15) 0.0378(14) -0.0117(12) 0.0032(13) 0.0035(13) F43 0.0870(14) 0.0637(11) 0.0484(10) -0.0076(8) 0.0224(9) 0.0157(10) C44 0.0529(17) 0.0418(14) 0.0520(16) -0.0063(13) -0.0036(15) 0.0140(13) F44 0.0964(15) 0.0643(11) 0.0675(12) -0.0087(10) -0.0024(12) 0.0419(12) C45 0.0587(17) 0.0401(14) 0.0405(14) 0.0004(12) -0.0077(14) 0.0053(13) F45 0.1111(17) 0.0539(10) 0.0498(10) 0.0134(8) -0.0048(11) 0.0240(11) C46 0.0398(13) 0.0388(13) 0.0321(13) -0.0020(11) 0.0017(11) -0.0056(11) F46 0.0659(11) 0.0512(9) 0.0360(8) 0.0088(7) 0.0137(8) 0.0046(8) _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 P1 C11 1.826(2) . ? P1 C21 1.832(2) . ? P1 C1 1.833(3) . ? P1 C3 1.919(2) . ? B1 O1 1.497(3) . ? B1 C2 1.624(4) . ? B1 C31 1.659(4) . ? B1 C41 1.667(4) . ? O1 C3 1.375(3) . ? C1 C2 1.543(3) . ? C3 C4 1.507(3) . ? C4 C5 1.391(3) . ? C4 C9 1.399(3) . ? C5 C6 1.376(4) . ? C6 C7 1.389(4) . ? C7 C8 1.385(4) . ? C8 C9 1.378(4) . ? C11 C12 1.403(4) . ? C11 C16 1.410(4) . ? C12 C13 1.397(4) . ? C12 C17 1.510(4) . ? C13 C14 1.373(4) . ? C14 C15 1.384(4) . ? C14 C18 1.509(4) . ? C15 C16 1.391(4) . ? C16 C19 1.513(4) . ? C21 C22 1.407(3) . ? C21 C26 1.418(4) . ? C22 C23 1.384(4) . ? C22 C27 1.501(4) . ? C23 C24 1.384(4) . ? C24 C25 1.390(4) . ? C24 C28 1.503(4) . ? C25 C26 1.392(4) . ? C26 C29 1.513(4) . ? C31 C36 1.388(4) . ? C31 C32 1.391(4) . ? C32 F32 1.356(3) . ? C32 C33 1.383(4) . ? C33 F33 1.345(3) . ? C33 C34 1.371(4) . ? C34 F34 1.352(3) . ? C34 C35 1.360(4) . ? C35 F35 1.345(3) . ? C35 C36 1.385(4) . ? C36 F36 1.349(3) . ? C41 C46 1.386(4) . ? C41 C42 1.388(4) . ? C42 F42 1.352(3) . ? C42 C43 1.385(4) . ? C43 F43 1.333(3) . ? C43 C44 1.371(4) . ? C44 F44 1.335(3) . ? C44 C45 1.381(4) . ? C45 F45 1.334(3) . ? C45 C46 1.382(4) . ? C46 F46 1.348(3) . ? 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 C11 P1 C21 108.12(11) . . ? C11 P1 C1 116.34(12) . . ? C21 P1 C1 101.76(12) . . ? C11 P1 C3 107.21(11) . . ? C21 P1 C3 126.23(11) . . ? C1 P1 C3 97.28(11) . . ? O1 B1 C2 108.3(2) . . ? O1 B1 C31 108.3(2) . . ? C2 B1 C31 109.3(2) . . ? O1 B1 C41 106.2(2) . . ? C2 B1 C41 115.8(2) . . ? C31 B1 C41 108.7(2) . . ? C3 O1 B1 117.31(19) . . ? C2 C1 P1 110.70(17) . . ? C1 C2 B1 113.6(2) . . ? O1 C3 C4 112.0(2) . . ? O1 C3 P1 111.25(17) . . ? C4 C3 P1 118.79(17) . . ? C5 C4 C9 118.6(2) . . ? C5 C4 C3 120.2(2) . . ? C9 C4 C3 120.9(2) . . ? C6 C5 C4 120.5(2) . . ? C5 C6 C7 120.7(3) . . ? C8 C7 C6 119.0(3) . . ? C9 C8 C7 120.6(2) . . ? C8 C9 C4 120.4(2) . . ? C12 C11 C16 119.9(2) . . ? C12 C11 P1 115.97(18) . . ? C16 C11 P1 124.0(2) . . ? C13 C12 C11 118.8(2) . . ? C13 C12 C17 116.3(2) . . ? C11 C12 C17 124.8(2) . . ? C14 C13 C12 122.3(3) . . ? C13 C14 C15 117.6(2) . . ? C13 C14 C18 120.8(3) . . ? C15 C14 C18 121.5(3) . . ? C14 C15 C16 123.2(3) . . ? C15 C16 C11 117.8(3) . . ? C15 C16 C19 116.1(3) . . ? C11 C16 C19 126.0(2) . . ? C22 C21 C26 119.7(2) . . ? C22 C21 P1 124.20(19) . . ? C26 C21 P1 115.84(18) . . ? C23 C22 C21 118.8(2) . . ? C23 C22 C27 118.3(2) . . ? C21 C22 C27 122.9(2) . . ? C24 C23 C22 122.9(3) . . ? C23 C24 C25 117.4(2) . . ? C23 C24 C28 121.3(3) . . ? C25 C24 C28 121.2(3) . . ? C24 C25 C26 122.6(3) . . ? C25 C26 C21 118.4(2) . . ? C25 C26 C29 115.6(2) . . ? C21 C26 C29 125.9(2) . . ? C36 C31 C32 113.4(2) . . ? C36 C31 B1 126.0(2) . . ? C32 C31 B1 120.6(2) . . ? F32 C32 C33 116.2(2) . . ? F32 C32 C31 119.4(2) . . ? C33 C32 C31 124.3(3) . . ? F33 C33 C34 120.2(2) . . ? F33 C33 C32 120.8(3) . . ? C34 C33 C32 119.0(3) . . ? F34 C34 C35 120.4(3) . . ? F34 C34 C33 120.0(3) . . ? C35 C34 C33 119.6(2) . . ? F35 C35 C34 120.1(2) . . ? F35 C35 C36 120.1(3) . . ? C34 C35 C36 119.8(3) . . ? F36 C36 C35 115.3(2) . . ? F36 C36 C31 120.9(2) . . ? C35 C36 C31 123.8(3) . . ? C46 C41 C42 113.2(2) . . ? C46 C41 B1 119.6(2) . . ? C42 C41 B1 127.1(2) . . ? F42 C42 C43 114.9(2) . . ? F42 C42 C41 120.6(2) . . ? C43 C42 C41 124.5(2) . . ? F43 C43 C44 120.1(2) . . ? F43 C43 C42 120.5(3) . . ? C44 C43 C42 119.4(2) . . ? F44 C44 C43 120.6(3) . . ? F44 C44 C45 120.4(3) . . ? C43 C44 C45 119.0(2) . . ? F45 C45 C44 119.6(2) . . ? F45 C45 C46 121.1(3) . . ? C44 C45 C46 119.3(3) . . ? F46 C46 C45 115.2(2) . . ? F46 C46 C41 120.3(2) . . ? C45 C46 C41 124.5(2) . . ? 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 C2 B1 O1 C3 64.4(3) . . . . ? C31 B1 O1 C3 -177.18(19) . . . . ? C41 B1 O1 C3 -60.6(2) . . . . ? C11 P1 C1 C2 -165.44(17) . . . . ? C21 P1 C1 C2 77.32(19) . . . . ? C3 P1 C1 C2 -52.11(19) . . . . ? P1 C1 C2 B1 60.3(2) . . . . ? O1 B1 C2 C1 -58.9(3) . . . . ? C31 B1 C2 C1 -176.7(2) . . . . ? C41 B1 C2 C1 60.2(3) . . . . ? B1 O1 C3 C4 157.6(2) . . . . ? B1 O1 C3 P1 -66.8(2) . . . . ? C11 P1 C3 O1 175.55(17) . . . . ? C21 P1 C3 O1 -55.4(2) . . . . ? C1 P1 C3 O1 55.03(18) . . . . ? C11 P1 C3 C4 -52.2(2) . . . . ? C21 P1 C3 C4 76.9(2) . . . . ? C1 P1 C3 C4 -172.7(2) . . . . ? O1 C3 C4 C5 15.5(3) . . . . ? P1 C3 C4 C5 -116.5(2) . . . . ? O1 C3 C4 C9 -159.0(2) . . . . ? P1 C3 C4 C9 69.0(3) . . . . ? C9 C4 C5 C6 -3.3(4) . . . . ? C3 C4 C5 C6 -177.9(3) . . . . ? C4 C5 C6 C7 0.9(5) . . . . ? C5 C6 C7 C8 1.4(5) . . . . ? C6 C7 C8 C9 -1.2(4) . . . . ? C7 C8 C9 C4 -1.2(4) . . . . ? C5 C4 C9 C8 3.4(4) . . . . ? C3 C4 C9 C8 178.0(2) . . . . ? C21 P1 C11 C12 -46.9(2) . . . . ? C1 P1 C11 C12 -160.52(18) . . . . ? C3 P1 C11 C12 91.9(2) . . . . ? C21 P1 C11 C16 130.3(2) . . . . ? C1 P1 C11 C16 16.6(3) . . . . ? C3 P1 C11 C16 -90.9(2) . . . . ? C16 C11 C12 C13 -5.4(4) . . . . ? P1 C11 C12 C13 171.9(2) . . . . ? C16 C11 C12 C17 173.1(2) . . . . ? P1 C11 C12 C17 -9.6(3) . . . . ? C11 C12 C13 C14 1.7(4) . . . . ? C17 C12 C13 C14 -176.9(3) . . . . ? C12 C13 C14 C15 2.9(4) . . . . ? C12 C13 C14 C18 -178.8(3) . . . . ? C13 C14 C15 C16 -4.1(4) . . . . ? C18 C14 C15 C16 177.7(3) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? C14 C15 C16 C19 -180.0(3) . . . . ? C12 C11 C16 C15 4.3(4) . . . . ? P1 C11 C16 C15 -172.8(2) . . . . ? C12 C11 C16 C19 -175.2(3) . . . . ? P1 C11 C16 C19 7.8(4) . . . . ? C11 P1 C21 C22 130.6(2) . . . . ? C1 P1 C21 C22 -106.4(2) . . . . ? C3 P1 C21 C22 1.8(3) . . . . ? C11 P1 C21 C26 -55.0(2) . . . . ? C1 P1 C21 C26 68.1(2) . . . . ? C3 P1 C21 C26 176.29(17) . . . . ? C26 C21 C22 C23 -3.9(4) . . . . ? P1 C21 C22 C23 170.34(19) . . . . ? C26 C21 C22 C27 173.5(2) . . . . ? P1 C21 C22 C27 -12.2(3) . . . . ? C21 C22 C23 C24 1.5(4) . . . . ? C27 C22 C23 C24 -176.1(3) . . . . ? C22 C23 C24 C25 1.8(4) . . . . ? C22 C23 C24 C28 -178.6(3) . . . . ? C23 C24 C25 C26 -2.8(4) . . . . ? C28 C24 C25 C26 177.6(3) . . . . ? C24 C25 C26 C21 0.4(4) . . . . ? C24 C25 C26 C29 177.8(2) . . . . ? C22 C21 C26 C25 3.0(4) . . . . ? P1 C21 C26 C25 -171.72(19) . . . . ? C22 C21 C26 C29 -174.1(2) . . . . ? P1 C21 C26 C29 11.2(3) . . . . ? O1 B1 C31 C36 -18.2(3) . . . . ? C2 B1 C31 C36 99.6(3) . . . . ? C41 B1 C31 C36 -133.2(2) . . . . ? O1 B1 C31 C32 164.1(2) . . . . ? C2 B1 C31 C32 -78.1(3) . . . . ? C41 B1 C31 C32 49.1(3) . . . . ? C36 C31 C32 F32 -178.1(2) . . . . ? B1 C31 C32 F32 -0.1(4) . . . . ? C36 C31 C32 C33 0.5(4) . . . . ? B1 C31 C32 C33 178.5(2) . . . . ? F32 C32 C33 F33 -0.1(4) . . . . ? C31 C32 C33 F33 -178.8(2) . . . . ? F32 C32 C33 C34 178.9(2) . . . . ? C31 C32 C33 C34 0.3(4) . . . . ? F33 C33 C34 F34 0.4(4) . . . . ? C32 C33 C34 F34 -178.7(2) . . . . ? F33 C33 C34 C35 178.3(3) . . . . ? C32 C33 C34 C35 -0.7(4) . . . . ? F34 C34 C35 F35 -0.6(4) . . . . ? C33 C34 C35 F35 -178.6(3) . . . . ? F34 C34 C35 C36 178.3(3) . . . . ? C33 C34 C35 C36 0.4(4) . . . . ? F35 C35 C36 F36 0.5(4) . . . . ? C34 C35 C36 F36 -178.5(2) . . . . ? F35 C35 C36 C31 179.4(2) . . . . ? C34 C35 C36 C31 0.4(4) . . . . ? C32 C31 C36 F36 178.0(2) . . . . ? B1 C31 C36 F36 0.1(4) . . . . ? C32 C31 C36 C35 -0.8(4) . . . . ? B1 C31 C36 C35 -178.7(2) . . . . ? O1 B1 C41 C46 -44.9(3) . . . . ? C2 B1 C41 C46 -165.2(2) . . . . ? C31 B1 C41 C46 71.4(3) . . . . ? O1 B1 C41 C42 131.0(2) . . . . ? C2 B1 C41 C42 10.8(4) . . . . ? C31 B1 C41 C42 -112.6(3) . . . . ? C46 C41 C42 F42 -177.1(2) . . . . ? B1 C41 C42 F42 6.7(4) . . . . ? C46 C41 C42 C43 2.9(4) . . . . ? B1 C41 C42 C43 -173.2(3) . . . . ? F42 C42 C43 F43 -2.1(4) . . . . ? C41 C42 C43 F43 177.9(3) . . . . ? F42 C42 C43 C44 178.7(3) . . . . ? C41 C42 C43 C44 -1.3(4) . . . . ? F43 C43 C44 F44 1.8(5) . . . . ? C42 C43 C44 F44 -179.0(3) . . . . ? F43 C43 C44 C45 -179.8(3) . . . . ? C42 C43 C44 C45 -0.6(4) . . . . ? F44 C44 C45 F45 -0.2(5) . . . . ? C43 C44 C45 F45 -178.6(3) . . . . ? F44 C44 C45 C46 179.1(3) . . . . ? C43 C44 C45 C46 0.7(4) . . . . ? F45 C45 C46 F46 0.1(4) . . . . ? C44 C45 C46 F46 -179.2(3) . . . . ? F45 C45 C46 C41 -179.6(3) . . . . ? C44 C45 C46 C41 1.1(4) . . . . ? C42 C41 C46 F46 177.6(2) . . . . ? B1 C41 C46 F46 -6.0(4) . . . . ? C42 C41 C46 C45 -2.8(4) . . . . ? B1 C41 C46 C45 173.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.326 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041 # Attachment '- 5.cif' data_erk5132 _database_code_depnum_ccdc_archive 'CCDC 767246' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 B F10 N P' _chemical_formula_weight 721.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.1539(6) _cell_length_b 12.4332(4) _cell_length_c 17.1214(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.333(2) _cell_angle_gamma 90.00 _cell_volume 3423.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5891 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8117 _exptl_absorpt_correction_T_max 0.8685 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26661 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 67.59 _reflns_number_total 6016 _reflns_number_gt 4855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'COllect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^2^+0.8805P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6016 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1390 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.88413(4) 0.62858(5) 0.05588(3) 0.04862(18) Uani 1 1 d . . . B1 B 0.97497(16) 0.8044(2) 0.26114(15) 0.0461(6) Uani 1 1 d . . . C1 C 0.96157(15) 0.70000(18) 0.12466(13) 0.0504(5) Uani 1 1 d . . . H1A H 1.0134 0.6586 0.1311 0.060 Uiso 1 1 calc R . . H1B H 0.9739 0.7706 0.1031 0.060 Uiso 1 1 calc R . . C2 C 0.92708(15) 0.71417(17) 0.20485(13) 0.0493(5) Uani 1 1 d . . . H2A H 0.9304 0.6449 0.2323 0.059 Uiso 1 1 calc R . . H2B H 0.8682 0.7339 0.1961 0.059 Uiso 1 1 calc R . . N3 N 0.95068(12) 0.92648(14) 0.22981(11) 0.0473(4) Uani 1 1 d . . . C4 C 0.99877(16) 1.01070(19) 0.25350(16) 0.0598(6) Uani 1 1 d . . . H4 H 1.0480 0.9983 0.2861 0.072 Uiso 1 1 calc R . . C5 C 0.97831(19) 1.1140(2) 0.23168(19) 0.0713(8) Uani 1 1 d . . . H5 H 1.0136 1.1713 0.2481 0.086 Uiso 1 1 calc R . . C6 C 0.9057(2) 1.1328(2) 0.1855(2) 0.0778(8) Uani 1 1 d . . . H6 H 0.8905 1.2031 0.1699 0.093 Uiso 1 1 calc R . . C7 C 0.8557(2) 1.0475(2) 0.16259(18) 0.0763(8) Uani 1 1 d . . . H7 H 0.8052 1.0587 0.1317 0.092 Uiso 1 1 calc R . . C8 C 0.87983(16) 0.9454(2) 0.18509(15) 0.0578(6) Uani 1 1 d . . . H8 H 0.8455 0.8871 0.1686 0.069 Uiso 1 1 calc R . . C11 C 0.91917(15) 0.62088(17) -0.04362(14) 0.0503(5) Uani 1 1 d . . . C12 C 1.00141(16) 0.62951(18) -0.06420(15) 0.0554(6) Uani 1 1 d . . . C13 C 1.01765(19) 0.61375(18) -0.14197(17) 0.0632(7) Uani 1 1 d . . . H13 H 1.0730 0.6174 -0.1546 0.076 Uiso 1 1 calc R . . C14 C 0.9555(2) 0.59294(19) -0.20149(16) 0.0662(7) Uani 1 1 d . . . C15 C 0.87614(19) 0.5804(2) -0.18049(15) 0.0642(7) Uani 1 1 d . . . H15 H 0.8332 0.5642 -0.2196 0.077 Uiso 1 1 calc R . . C16 C 0.85695(17) 0.59085(19) -0.10344(14) 0.0575(6) Uani 1 1 d . . . C17 C 1.07558(16) 0.6568(2) -0.00721(18) 0.0667(7) Uani 1 1 d . . . H17A H 1.0700 0.7297 0.0117 0.100 Uiso 1 1 calc R . . H17B H 1.1260 0.6509 -0.0335 0.100 Uiso 1 1 calc R . . H17C H 1.0782 0.6073 0.0367 0.100 Uiso 1 1 calc R . . C18 C 0.9759(3) 0.5851(3) -0.28581(18) 0.0913(11) Uani 1 1 d . . . H18A H 0.9257 0.5689 -0.3193 0.137 Uiso 1 1 calc R . . H18B H 1.0164 0.5284 -0.2905 0.137 Uiso 1 1 calc R . . H18C H 0.9987 0.6530 -0.3017 0.137 Uiso 1 1 calc R . . C19 C 0.76823(17) 0.5681(3) -0.08755(17) 0.0757(8) Uani 1 1 d . . . H19A H 0.7395 0.6354 -0.0805 0.114 Uiso 1 1 calc R . . H19B H 0.7678 0.5250 -0.0404 0.114 Uiso 1 1 calc R . . H19C H 0.7403 0.5292 -0.1316 0.114 Uiso 1 1 calc R . . C21 C 0.80375(14) 0.73522(18) 0.04663(13) 0.0497(5) Uani 1 1 d . . . C22 C 0.73102(15) 0.7151(2) 0.08394(14) 0.0558(6) Uani 1 1 d . . . C23 C 0.66943(17) 0.7941(2) 0.08213(16) 0.0666(7) Uani 1 1 d . . . H23 H 0.6214 0.7808 0.1077 0.080 Uiso 1 1 calc R . . C24 C 0.67657(18) 0.8911(2) 0.04425(16) 0.0688(7) Uani 1 1 d . . . C25 C 0.74842(18) 0.9100(2) 0.00809(15) 0.0635(7) Uani 1 1 d . . . H25 H 0.7542 0.9759 -0.0177 0.076 Uiso 1 1 calc R . . C26 C 0.81221(15) 0.83500(19) 0.00857(13) 0.0530(6) Uani 1 1 d . . . C27 C 0.71573(18) 0.6110(2) 0.12527(18) 0.0710(7) Uani 1 1 d . . . H27A H 0.7143 0.5522 0.0880 0.106 Uiso 1 1 calc R . . H27B H 0.6630 0.6150 0.1480 0.106 Uiso 1 1 calc R . . H27C H 0.7601 0.5989 0.1665 0.106 Uiso 1 1 calc R . . C28 C 0.6081(2) 0.9737(3) 0.0411(2) 0.1036(12) Uani 1 1 d . . . H28A H 0.6129 1.0154 0.0892 0.155 Uiso 1 1 calc R . . H28B H 0.5546 0.9378 0.0353 0.155 Uiso 1 1 calc R . . H28C H 0.6127 1.0213 -0.0032 0.155 Uiso 1 1 calc R . . C29 C 0.88661(18) 0.8654(2) -0.03344(17) 0.0675(7) Uani 1 1 d . . . H29A H 0.8838 0.8289 -0.0837 0.101 Uiso 1 1 calc R . . H29B H 0.9370 0.8443 -0.0020 0.101 Uiso 1 1 calc R . . H29C H 0.8869 0.9426 -0.0417 0.101 Uiso 1 1 calc R . . C31 C 0.94565(14) 0.80726(18) 0.35125(13) 0.0481(5) Uani 1 1 d . . . C32 C 0.86827(16) 0.7748(2) 0.37074(15) 0.0612(6) Uani 1 1 d . . . F32 F 0.81085(10) 0.73508(17) 0.31560(10) 0.0921(6) Uani 1 1 d . . . C33 C 0.84220(18) 0.7790(2) 0.44521(17) 0.0697(7) Uani 1 1 d . . . F33 F 0.76642(12) 0.7432(2) 0.45870(12) 0.1097(7) Uani 1 1 d . . . C34 C 0.89439(19) 0.8201(2) 0.50526(16) 0.0680(7) Uani 1 1 d . . . F34 F 0.87042(13) 0.82673(17) 0.57818(10) 0.0959(6) Uani 1 1 d . . . C35 C 0.97131(17) 0.8552(2) 0.48993(14) 0.0586(6) Uani 1 1 d . . . F35 F 1.02264(11) 0.89769(14) 0.54840(9) 0.0776(5) Uani 1 1 d . . . C36 C 0.99504(15) 0.84828(19) 0.41489(14) 0.0513(5) Uani 1 1 d . . . F36 F 1.07160(9) 0.88637(13) 0.40557(9) 0.0681(4) Uani 1 1 d . . . C41 C 1.07507(14) 0.78352(17) 0.25653(12) 0.0458(5) Uani 1 1 d . . . C42 C 1.12282(15) 0.82582(18) 0.20062(14) 0.0507(5) Uani 1 1 d . . . F42 F 1.09156(10) 0.90316(11) 0.15052(9) 0.0654(4) Uani 1 1 d . . . C43 C 1.20245(16) 0.7930(2) 0.18993(15) 0.0583(6) Uani 1 1 d . . . F43 F 1.24441(10) 0.83928(14) 0.13432(10) 0.0801(5) Uani 1 1 d . . . C44 C 1.23801(16) 0.7116(2) 0.23475(15) 0.0619(7) Uani 1 1 d . . . F44 F 1.31517(10) 0.67665(16) 0.22512(10) 0.0875(5) Uani 1 1 d . . . C45 C 1.19366(17) 0.6651(2) 0.29034(14) 0.0593(6) Uani 1 1 d . . . F45 F 1.22649(11) 0.58172(14) 0.33226(9) 0.0786(5) Uani 1 1 d . . . C46 C 1.11499(15) 0.70197(18) 0.30024(13) 0.0497(5) Uani 1 1 d . . . F46 F 1.07504(10) 0.65191(11) 0.35621(8) 0.0635(4) 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 P1 0.0475(3) 0.0483(3) 0.0480(3) -0.0013(2) -0.0068(2) -0.0002(2) B1 0.0443(14) 0.0487(13) 0.0441(13) 0.0027(10) -0.0023(10) -0.0032(10) C1 0.0499(13) 0.0497(12) 0.0494(13) -0.0023(10) -0.0067(10) 0.0010(10) C2 0.0495(13) 0.0480(11) 0.0481(12) 0.0036(9) -0.0086(10) -0.0014(10) N3 0.0461(10) 0.0476(10) 0.0478(10) -0.0015(8) 0.0028(8) -0.0013(8) C4 0.0551(14) 0.0516(13) 0.0721(16) -0.0035(11) 0.0031(12) -0.0056(11) C5 0.0723(19) 0.0510(14) 0.091(2) -0.0036(13) 0.0099(16) -0.0073(12) C6 0.091(2) 0.0497(14) 0.091(2) 0.0062(14) 0.0016(18) 0.0107(14) C7 0.083(2) 0.0589(15) 0.083(2) 0.0009(14) -0.0165(16) 0.0150(14) C8 0.0558(14) 0.0553(13) 0.0596(14) -0.0002(11) -0.0088(11) 0.0029(11) C11 0.0514(13) 0.0449(11) 0.0533(13) -0.0020(10) -0.0019(10) 0.0025(9) C12 0.0589(15) 0.0449(12) 0.0620(15) -0.0022(10) 0.0032(12) 0.0021(10) C13 0.0739(18) 0.0462(13) 0.0715(17) -0.0033(11) 0.0170(14) 0.0018(11) C14 0.098(2) 0.0449(12) 0.0564(15) -0.0038(11) 0.0115(15) 0.0062(13) C15 0.081(2) 0.0580(14) 0.0507(14) -0.0071(11) -0.0073(13) 0.0092(13) C16 0.0629(15) 0.0545(13) 0.0526(14) -0.0039(10) -0.0078(11) 0.0054(11) C17 0.0492(14) 0.0693(16) 0.0822(19) -0.0142(13) 0.0093(13) -0.0024(12) C18 0.143(3) 0.0702(18) 0.0636(18) -0.0084(14) 0.026(2) 0.0016(19) C19 0.0564(16) 0.100(2) 0.0664(17) -0.0211(15) -0.0146(13) -0.0047(15) C21 0.0468(13) 0.0576(13) 0.0423(12) -0.0020(10) -0.0079(10) 0.0009(10) C22 0.0469(13) 0.0728(15) 0.0458(13) -0.0030(11) -0.0063(10) -0.0024(11) C23 0.0482(15) 0.0893(19) 0.0610(16) -0.0043(14) -0.0025(12) 0.0073(13) C24 0.0578(16) 0.091(2) 0.0553(15) -0.0038(14) -0.0058(12) 0.0245(14) C25 0.0716(18) 0.0676(15) 0.0484(13) 0.0035(11) -0.0099(12) 0.0172(13) C26 0.0555(14) 0.0587(13) 0.0430(12) 0.0016(10) -0.0045(10) 0.0066(11) C27 0.0571(16) 0.0848(19) 0.0709(18) 0.0062(14) 0.0057(13) -0.0098(14) C28 0.085(2) 0.123(3) 0.103(3) 0.012(2) 0.005(2) 0.050(2) C29 0.0705(18) 0.0607(15) 0.0716(17) 0.0149(13) 0.0088(14) 0.0087(13) C31 0.0441(12) 0.0518(12) 0.0474(12) 0.0033(9) -0.0006(10) -0.0025(9) C32 0.0506(14) 0.0768(16) 0.0553(14) -0.0003(12) 0.0004(11) -0.0119(12) F32 0.0581(10) 0.1482(16) 0.0698(10) -0.0135(10) 0.0043(8) -0.0400(10) C33 0.0574(16) 0.0899(19) 0.0639(17) 0.0023(14) 0.0178(13) -0.0104(14) F33 0.0724(12) 0.168(2) 0.0932(14) -0.0041(13) 0.0343(11) -0.0372(12) C34 0.0754(19) 0.0766(17) 0.0541(15) 0.0032(12) 0.0173(14) 0.0052(14) F34 0.1048(15) 0.1294(15) 0.0577(10) -0.0021(10) 0.0298(10) -0.0026(12) C35 0.0598(15) 0.0676(15) 0.0473(13) -0.0068(11) -0.0012(11) 0.0067(12) F35 0.0769(11) 0.0997(11) 0.0539(9) -0.0203(8) -0.0070(8) 0.0062(9) C36 0.0439(13) 0.0580(13) 0.0514(13) -0.0025(10) 0.0013(10) 0.0012(10) F36 0.0478(8) 0.0944(10) 0.0615(9) -0.0216(7) 0.0024(7) -0.0152(7) C41 0.0478(12) 0.0473(11) 0.0410(11) -0.0060(9) -0.0032(9) -0.0031(9) C42 0.0487(13) 0.0531(12) 0.0496(13) -0.0027(10) 0.0003(10) -0.0009(10) F42 0.0663(9) 0.0657(8) 0.0657(9) 0.0158(7) 0.0139(7) 0.0032(7) C43 0.0530(14) 0.0693(15) 0.0533(14) -0.0101(12) 0.0083(11) -0.0050(12) F43 0.0690(10) 0.0963(11) 0.0793(11) -0.0015(9) 0.0301(9) -0.0032(8) C44 0.0472(14) 0.0829(17) 0.0547(15) -0.0183(13) -0.0006(11) 0.0110(12) F44 0.0574(10) 0.1257(14) 0.0794(11) -0.0178(10) 0.0061(8) 0.0284(9) C45 0.0598(15) 0.0685(15) 0.0463(13) -0.0075(11) -0.0123(11) 0.0139(12) F45 0.0834(11) 0.0904(11) 0.0588(9) 0.0000(8) -0.0113(8) 0.0350(9) C46 0.0499(13) 0.0560(12) 0.0416(11) -0.0049(10) -0.0047(10) 0.0005(10) F46 0.0706(10) 0.0657(8) 0.0538(8) 0.0119(6) 0.0033(7) 0.0079(7) _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 P1 C11 1.847(2) . ? P1 C21 1.852(2) . ? P1 C1 1.862(2) . ? B1 C2 1.627(3) . ? B1 N3 1.645(3) . ? B1 C41 1.647(3) . ? B1 C31 1.656(3) . ? C1 C2 1.539(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? N3 C8 1.338(3) . ? N3 C4 1.344(3) . ? C4 C5 1.369(4) . ? C4 H4 0.9400 . ? C5 C6 1.373(5) . ? C5 H5 0.9400 . ? C6 C7 1.368(4) . ? C6 H6 0.9400 . ? C7 C8 1.372(4) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C11 C12 1.410(4) . ? C11 C16 1.417(3) . ? C12 C13 1.395(4) . ? C12 C17 1.512(4) . ? C13 C14 1.387(4) . ? C13 H13 0.9400 . ? C14 C15 1.372(4) . ? C14 C18 1.514(4) . ? C15 C16 1.389(4) . ? C15 H15 0.9400 . ? C16 C19 1.510(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.411(3) . ? C21 C26 1.414(3) . ? C22 C23 1.397(4) . ? C22 C27 1.506(4) . ? C23 C24 1.379(4) . ? C23 H23 0.9400 . ? C24 C25 1.385(4) . ? C24 C28 1.507(4) . ? C25 C26 1.389(4) . ? C25 H25 0.9400 . ? C26 C29 1.505(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 C32 1.384(3) . ? C31 C36 1.386(3) . ? C32 F32 1.354(3) . ? C32 C33 1.380(4) . ? C33 F33 1.343(3) . ? C33 C34 1.366(4) . ? C34 F34 1.343(3) . ? C34 C35 1.365(4) . ? C35 F35 1.347(3) . ? C35 C36 1.377(3) . ? C36 F36 1.348(3) . ? C41 C46 1.384(3) . ? C41 C42 1.388(3) . ? C42 F42 1.355(3) . ? C42 C43 1.378(3) . ? C43 F43 1.348(3) . ? C43 C44 1.364(4) . ? C44 F44 1.345(3) . ? C44 C45 1.371(4) . ? C45 F45 1.342(3) . ? C45 C46 1.376(3) . ? C46 F46 1.355(3) . ? 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 C11 P1 C21 103.34(10) . . ? C11 P1 C1 111.26(11) . . ? C21 P1 C1 97.89(10) . . ? C2 B1 N3 110.92(17) . . ? C2 B1 C41 106.15(18) . . ? N3 B1 C41 109.58(17) . . ? C2 B1 C31 113.92(19) . . ? N3 B1 C31 101.74(17) . . ? C41 B1 C31 114.53(18) . . ? C2 C1 P1 109.94(16) . . ? C2 C1 H1A 109.7 . . ? P1 C1 H1A 109.7 . . ? C2 C1 H1B 109.7 . . ? P1 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C1 C2 B1 114.56(19) . . ? C1 C2 H2A 108.6 . . ? B1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? B1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C8 N3 C4 118.4(2) . . ? C8 N3 B1 120.96(19) . . ? C4 N3 B1 120.47(19) . . ? N3 C4 C5 122.0(3) . . ? N3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? N3 C8 C7 122.0(2) . . ? N3 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C12 C11 C16 117.5(2) . . ? C12 C11 P1 127.11(18) . . ? C16 C11 P1 115.01(19) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 C17 116.1(2) . . ? C11 C12 C17 124.4(2) . . ? C14 C13 C12 122.7(3) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C15 C14 C13 117.3(2) . . ? C15 C14 C18 122.3(3) . . ? C13 C14 C18 120.4(3) . . ? C14 C15 C16 122.3(3) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 C19 116.9(2) . . ? C11 C16 C19 122.7(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 119.0(2) . . ? C22 C21 P1 116.16(17) . . ? C26 C21 P1 124.79(18) . . ? C23 C22 C21 119.1(2) . . ? C23 C22 C27 117.9(2) . . ? C21 C22 C27 123.0(2) . . ? C24 C23 C22 122.4(3) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C25 118.0(2) . . ? C23 C24 C28 121.3(3) . . ? C25 C24 C28 120.7(3) . . ? C24 C25 C26 122.4(3) . . ? C24 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C25 C26 C21 119.2(2) . . ? C25 C26 C29 117.0(2) . . ? C21 C26 C29 123.8(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 112.6(2) . . ? C32 C31 B1 124.2(2) . . ? C36 C31 B1 123.1(2) . . ? F32 C32 C33 114.2(2) . . ? F32 C32 C31 120.9(2) . . ? C33 C32 C31 124.9(2) . . ? F33 C33 C34 120.2(2) . . ? F33 C33 C32 120.5(3) . . ? C34 C33 C32 119.3(3) . . ? F34 C34 C35 120.3(3) . . ? F34 C34 C33 120.7(3) . . ? C35 C34 C33 118.9(2) . . ? F35 C35 C34 119.4(2) . . ? F35 C35 C36 120.8(2) . . ? C34 C35 C36 119.8(2) . . ? F36 C36 C35 115.2(2) . . ? F36 C36 C31 120.2(2) . . ? C35 C36 C31 124.5(2) . . ? C46 C41 C42 112.9(2) . . ? C46 C41 B1 120.0(2) . . ? C42 C41 B1 125.8(2) . . ? F42 C42 C43 115.1(2) . . ? F42 C42 C41 120.5(2) . . ? C43 C42 C41 124.4(2) . . ? F43 C43 C44 120.0(2) . . ? F43 C43 C42 120.3(2) . . ? C44 C43 C42 119.6(2) . . ? F44 C44 C43 121.2(3) . . ? F44 C44 C45 119.9(2) . . ? C43 C44 C45 118.9(2) . . ? F45 C45 C44 119.4(2) . . ? F45 C45 C46 121.0(2) . . ? C44 C45 C46 119.6(2) . . ? F46 C46 C45 116.1(2) . . ? F46 C46 C41 119.4(2) . . ? C45 C46 C41 124.5(2) . . ? 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 C11 P1 C1 C2 174.85(14) . . . . ? C21 P1 C1 C2 67.16(17) . . . . ? P1 C1 C2 B1 -162.70(16) . . . . ? N3 B1 C2 C1 73.7(2) . . . . ? C41 B1 C2 C1 -45.3(2) . . . . ? C31 B1 C2 C1 -172.23(18) . . . . ? C2 B1 N3 C8 23.2(3) . . . . ? C41 B1 N3 C8 140.1(2) . . . . ? C31 B1 N3 C8 -98.3(2) . . . . ? C2 B1 N3 C4 -161.8(2) . . . . ? C41 B1 N3 C4 -44.9(3) . . . . ? C31 B1 N3 C4 76.7(2) . . . . ? C8 N3 C4 C5 -1.6(4) . . . . ? B1 N3 C4 C5 -176.8(2) . . . . ? N3 C4 C5 C6 1.4(4) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C5 C6 C7 C8 -1.0(5) . . . . ? C4 N3 C8 C7 0.5(4) . . . . ? B1 N3 C8 C7 175.6(2) . . . . ? C6 C7 C8 N3 0.8(5) . . . . ? C21 P1 C11 C12 125.8(2) . . . . ? C1 P1 C11 C12 21.7(2) . . . . ? C21 P1 C11 C16 -61.90(19) . . . . ? C1 P1 C11 C16 -166.00(17) . . . . ? C16 C11 C12 C13 3.1(3) . . . . ? P1 C11 C12 C13 175.22(17) . . . . ? C16 C11 C12 C17 -177.8(2) . . . . ? P1 C11 C12 C17 -5.7(3) . . . . ? C11 C12 C13 C14 2.1(4) . . . . ? C17 C12 C13 C14 -177.1(2) . . . . ? C12 C13 C14 C15 -4.6(4) . . . . ? C12 C13 C14 C18 175.2(2) . . . . ? C13 C14 C15 C16 1.8(4) . . . . ? C18 C14 C15 C16 -178.0(2) . . . . ? C14 C15 C16 C11 3.4(4) . . . . ? C14 C15 C16 C19 -176.2(2) . . . . ? C12 C11 C16 C15 -5.8(3) . . . . ? P1 C11 C16 C15 -178.82(18) . . . . ? C12 C11 C16 C19 173.8(2) . . . . ? P1 C11 C16 C19 0.7(3) . . . . ? C11 P1 C21 C22 137.73(17) . . . . ? C1 P1 C21 C22 -108.13(18) . . . . ? C11 P1 C21 C26 -45.3(2) . . . . ? C1 P1 C21 C26 68.9(2) . . . . ? C26 C21 C22 C23 0.1(3) . . . . ? P1 C21 C22 C23 177.27(18) . . . . ? C26 C21 C22 C27 179.3(2) . . . . ? P1 C21 C22 C27 -3.5(3) . . . . ? C21 C22 C23 C24 0.8(4) . . . . ? C27 C22 C23 C24 -178.5(3) . . . . ? C22 C23 C24 C25 -1.1(4) . . . . ? C22 C23 C24 C28 178.2(3) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C28 C24 C25 C26 -178.9(3) . . . . ? C24 C25 C26 C21 0.5(4) . . . . ? C24 C25 C26 C29 179.6(3) . . . . ? C22 C21 C26 C25 -0.8(3) . . . . ? P1 C21 C26 C25 -177.67(18) . . . . ? C22 C21 C26 C29 -179.7(2) . . . . ? P1 C21 C26 C29 3.4(3) . . . . ? C2 B1 C31 C32 -26.6(3) . . . . ? N3 B1 C31 C32 92.8(3) . . . . ? C41 B1 C31 C32 -149.1(2) . . . . ? C2 B1 C31 C36 157.0(2) . . . . ? N3 B1 C31 C36 -83.5(2) . . . . ? C41 B1 C31 C36 34.6(3) . . . . ? C36 C31 C32 F32 178.3(2) . . . . ? B1 C31 C32 F32 1.6(4) . . . . ? C36 C31 C32 C33 -1.7(4) . . . . ? B1 C31 C32 C33 -178.4(3) . . . . ? F32 C32 C33 F33 1.5(4) . . . . ? C31 C32 C33 F33 -178.4(3) . . . . ? F32 C32 C33 C34 -178.5(3) . . . . ? C31 C32 C33 C34 1.6(5) . . . . ? F33 C33 C34 F34 -1.0(4) . . . . ? C32 C33 C34 F34 179.1(3) . . . . ? F33 C33 C34 C35 179.5(3) . . . . ? C32 C33 C34 C35 -0.4(4) . . . . ? F34 C34 C35 F35 -0.7(4) . . . . ? C33 C34 C35 F35 178.8(2) . . . . ? F34 C34 C35 C36 -179.8(2) . . . . ? C33 C34 C35 C36 -0.3(4) . . . . ? F35 C35 C36 F36 0.1(3) . . . . ? C34 C35 C36 F36 179.1(2) . . . . ? F35 C35 C36 C31 -179.0(2) . . . . ? C34 C35 C36 C31 0.1(4) . . . . ? C32 C31 C36 F36 -178.1(2) . . . . ? B1 C31 C36 F36 -1.4(3) . . . . ? C32 C31 C36 C35 0.9(3) . . . . ? B1 C31 C36 C35 177.6(2) . . . . ? C2 B1 C41 C46 -79.5(2) . . . . ? N3 B1 C41 C46 160.67(19) . . . . ? C31 B1 C41 C46 47.1(3) . . . . ? C2 B1 C41 C42 86.6(2) . . . . ? N3 B1 C41 C42 -33.2(3) . . . . ? C31 B1 C41 C42 -146.8(2) . . . . ? C46 C41 C42 F42 177.11(19) . . . . ? B1 C41 C42 F42 10.1(3) . . . . ? C46 C41 C42 C43 -1.4(3) . . . . ? B1 C41 C42 C43 -168.4(2) . . . . ? F42 C42 C43 F43 1.8(3) . . . . ? C41 C42 C43 F43 -179.6(2) . . . . ? F42 C42 C43 C44 -176.7(2) . . . . ? C41 C42 C43 C44 1.9(4) . . . . ? F43 C43 C44 F44 0.6(4) . . . . ? C42 C43 C44 F44 179.1(2) . . . . ? F43 C43 C44 C45 -179.3(2) . . . . ? C42 C43 C44 C45 -0.8(4) . . . . ? F44 C44 C45 F45 -3.0(4) . . . . ? C43 C44 C45 F45 176.9(2) . . . . ? F44 C44 C45 C46 179.5(2) . . . . ? C43 C44 C45 C46 -0.6(4) . . . . ? F45 C45 C46 F46 2.4(3) . . . . ? C44 C45 C46 F46 179.9(2) . . . . ? F45 C45 C46 C41 -176.4(2) . . . . ? C44 C45 C46 C41 1.1(4) . . . . ? C42 C41 C46 F46 -178.87(19) . . . . ? B1 C41 C46 F46 -11.1(3) . . . . ? C42 C41 C46 C45 -0.1(3) . . . . ? B1 C41 C46 C45 167.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 67.59 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.199 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.039 # Attachment '- 6.cif' data_erk4768 _database_code_depnum_ccdc_archive 'CCDC 767247' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H35 B F10 N P' _chemical_formula_weight 725.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 10.4592(4) _cell_length_b 13.2592(5) _cell_length_c 14.5233(7) _cell_angle_alpha 99.281(2) _cell_angle_beta 99.394(2) _cell_angle_gamma 110.205(3) _cell_volume 1812.55(13) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3232 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7256 _exptl_absorpt_correction_T_max 0.8208 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21458 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.68 _diffrn_reflns_theta_max 68.10 _reflns_number_total 6332 _reflns_number_gt 5367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+1.2493P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6332 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 P1 P 0.78919(7) 0.47178(5) 0.16294(5) 0.04445(19) Uani 1 1 d . . . B1 B 0.9125(3) 0.8174(2) 0.1929(2) 0.0409(6) Uani 1 1 d . . . C1 C 0.7661(3) 0.6058(2) 0.1728(2) 0.0491(6) Uani 1 1 d . . . H1A H 0.6755 0.5941 0.1318 0.059 Uiso 1 1 calc R . . H1B H 0.7660 0.6348 0.2393 0.059 Uiso 1 1 calc R . . C2 C 0.8848(3) 0.6904(2) 0.14239(19) 0.0455(6) Uani 1 1 d . . . H2A H 0.8606 0.6797 0.0725 0.055 Uiso 1 1 calc R . . H2B H 0.9712 0.6772 0.1598 0.055 Uiso 1 1 calc R . . C3 C 0.7591(3) 0.82471(19) 0.17287(18) 0.0436(6) Uani 1 1 d . . . N4 N 0.6488(2) 0.82374(17) 0.15259(16) 0.0477(5) Uani 1 1 d . . . C5 C 0.5068(3) 0.8242(2) 0.1348(2) 0.0587(7) Uani 1 1 d . . . C6 C 0.4527(4) 0.8028(5) 0.0233(3) 0.1115(16) Uani 1 1 d . . . H6A H 0.5134 0.8617 0.0000 0.167 Uiso 1 1 calc R . . H6B H 0.3578 0.8008 0.0089 0.167 Uiso 1 1 calc R . . H6C H 0.4534 0.7326 -0.0078 0.167 Uiso 1 1 calc R . . C7 C 0.4210(5) 0.7402(6) 0.1749(7) 0.189(4) Uani 1 1 d . . . H7A H 0.4186 0.6686 0.1445 0.283 Uiso 1 1 calc R . . H7B H 0.3266 0.7393 0.1639 0.283 Uiso 1 1 calc R . . H7C H 0.4602 0.7561 0.2434 0.283 Uiso 1 1 calc R . . C8 C 0.5197(4) 0.9392(4) 0.1744(4) 0.1090(16) Uani 1 1 d . . . H8A H 0.5646 0.9613 0.2424 0.163 Uiso 1 1 calc R . . H8B H 0.4272 0.9420 0.1655 0.163 Uiso 1 1 calc R . . H8C H 0.5758 0.9890 0.1412 0.163 Uiso 1 1 calc R . . C11 C 0.6609(3) 0.3768(2) 0.2159(2) 0.0485(6) Uani 1 1 d . . . C12 C 0.5277(3) 0.3764(2) 0.2201(2) 0.0598(7) Uani 1 1 d . . . C13 C 0.4422(3) 0.3009(2) 0.2624(2) 0.0647(8) Uani 1 1 d . . . H13 H 0.3550 0.3039 0.2674 0.078 Uiso 1 1 calc R . . C14 C 0.4795(3) 0.2221(2) 0.2973(2) 0.0620(8) Uani 1 1 d . . . C15 C 0.6055(3) 0.2180(2) 0.2866(2) 0.0600(7) Uani 1 1 d . . . H15 H 0.6321 0.1634 0.3081 0.072 Uiso 1 1 calc R . . C16 C 0.6959(3) 0.2913(2) 0.2451(2) 0.0508(6) Uani 1 1 d . . . C17 C 0.4678(4) 0.4513(3) 0.1766(4) 0.1013(15) Uani 1 1 d . . . H17A H 0.3673 0.4234 0.1705 0.152 Uiso 1 1 calc R . . H17B H 0.4872 0.4531 0.1137 0.152 Uiso 1 1 calc R . . H17C H 0.5106 0.5253 0.2177 0.152 Uiso 1 1 calc R . . C18 C 0.3842(4) 0.1412(3) 0.3438(3) 0.0881(12) Uani 1 1 d . . . H18A H 0.3354 0.1779 0.3794 0.132 Uiso 1 1 calc R . . H18B H 0.4401 0.1156 0.3872 0.132 Uiso 1 1 calc R . . H18C H 0.3164 0.0787 0.2944 0.132 Uiso 1 1 calc R . . C19 C 0.8262(3) 0.2720(3) 0.2311(3) 0.0704(9) Uani 1 1 d . . . H19A H 0.9056 0.3217 0.2825 0.106 Uiso 1 1 calc R . . H19B H 0.8438 0.2857 0.1699 0.106 Uiso 1 1 calc R . . H19C H 0.8130 0.1961 0.2321 0.106 Uiso 1 1 calc R . . C21 C 0.9550(3) 0.52034(19) 0.25580(17) 0.0422(5) Uani 1 1 d . . . C22 C 0.9697(3) 0.5599(2) 0.35469(19) 0.0485(6) Uani 1 1 d . . . C23 C 1.1010(3) 0.5956(2) 0.4168(2) 0.0585(7) Uani 1 1 d . . . H23 H 1.1103 0.6220 0.4826 0.070 Uiso 1 1 calc R . . C24 C 1.2181(3) 0.5940(3) 0.3858(2) 0.0639(8) Uani 1 1 d . . . C25 C 1.2021(3) 0.5554(3) 0.2891(2) 0.0605(7) Uani 1 1 d . . . H25 H 1.2809 0.5536 0.2667 0.073 Uiso 1 1 calc R . . C26 C 1.0738(3) 0.5189(2) 0.22332(19) 0.0474(6) Uani 1 1 d . . . C27 C 0.8494(3) 0.5625(2) 0.3992(2) 0.0602(7) Uani 1 1 d . . . H27A H 0.7845 0.4875 0.3926 0.090 Uiso 1 1 calc R . . H27B H 0.8011 0.6023 0.3669 0.090 Uiso 1 1 calc R . . H27C H 0.8855 0.5994 0.4668 0.090 Uiso 1 1 calc R . . C28 C 1.3601(4) 0.6332(4) 0.4543(3) 0.1023(14) Uani 1 1 d . . . H28A H 1.3905 0.5719 0.4544 0.153 Uiso 1 1 calc R . . H28B H 1.3537 0.6617 0.5185 0.153 Uiso 1 1 calc R . . H28C H 1.4273 0.6913 0.4339 0.153 Uiso 1 1 calc R . . C29 C 1.0698(3) 0.4782(3) 0.1194(2) 0.0621(7) Uani 1 1 d . . . H29A H 1.1586 0.4727 0.1143 0.093 Uiso 1 1 calc R . . H29B H 1.0534 0.5297 0.0831 0.093 Uiso 1 1 calc R . . H29C H 0.9947 0.4060 0.0939 0.093 Uiso 1 1 calc R . . C31 C 0.9781(3) 0.84357(19) 0.30859(17) 0.0426(5) Uani 1 1 d . . . C32 C 0.9083(3) 0.8486(2) 0.3815(2) 0.0531(6) Uani 1 1 d . . . F32 F 0.77156(18) 0.83372(17) 0.36050(13) 0.0739(5) Uani 1 1 d . . . C33 C 0.9703(4) 0.8675(3) 0.4776(2) 0.0650(8) Uani 1 1 d . . . F33 F 0.8950(3) 0.8703(2) 0.54414(14) 0.0953(7) Uani 1 1 d . . . C34 C 1.1086(4) 0.8836(3) 0.5051(2) 0.0670(8) Uani 1 1 d . . . F34 F 1.1707(3) 0.9026(2) 0.59803(13) 0.0981(7) Uani 1 1 d . . . C35 C 1.1829(3) 0.8785(3) 0.4362(2) 0.0604(7) Uani 1 1 d . . . F35 F 1.3183(2) 0.89302(19) 0.46189(14) 0.0864(6) Uani 1 1 d . . . C36 C 1.1165(3) 0.8578(2) 0.34083(18) 0.0479(6) Uani 1 1 d . . . F36 F 1.19483(16) 0.85155(14) 0.27640(11) 0.0596(4) Uani 1 1 d . . . C41 C 1.0090(2) 0.91609(19) 0.14878(16) 0.0389(5) Uani 1 1 d . . . C42 C 1.0950(3) 0.9049(2) 0.08813(18) 0.0438(5) Uani 1 1 d . . . F42 F 1.10522(17) 0.80698(13) 0.05891(12) 0.0597(4) Uani 1 1 d . . . C43 C 1.1753(3) 0.9913(2) 0.05408(18) 0.0488(6) Uani 1 1 d . . . F43 F 1.25364(18) 0.97407(15) -0.00672(12) 0.0673(5) Uani 1 1 d . . . C44 C 1.1719(3) 1.0941(2) 0.08028(18) 0.0481(6) Uani 1 1 d . . . F44 F 1.24676(17) 1.17765(14) 0.04559(12) 0.0654(5) Uani 1 1 d . . . C45 C 1.0890(3) 1.1102(2) 0.14073(19) 0.0476(6) Uani 1 1 d . . . F45 F 1.08393(18) 1.21033(13) 0.16641(14) 0.0666(5) Uani 1 1 d . . . C46 C 1.0110(2) 1.0221(2) 0.17349(17) 0.0417(5) Uani 1 1 d . . . F46 F 0.93213(16) 1.04314(12) 0.23316(11) 0.0533(4) 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 P1 0.0423(3) 0.0367(3) 0.0503(4) 0.0104(3) 0.0081(3) 0.0113(3) B1 0.0402(14) 0.0407(14) 0.0450(15) 0.0166(12) 0.0144(12) 0.0147(11) C1 0.0442(13) 0.0397(13) 0.0630(16) 0.0183(12) 0.0126(12) 0.0125(11) C2 0.0481(14) 0.0422(13) 0.0477(14) 0.0158(11) 0.0135(11) 0.0157(11) C3 0.0445(14) 0.0374(12) 0.0490(14) 0.0157(10) 0.0166(11) 0.0108(10) N4 0.0397(12) 0.0424(11) 0.0605(13) 0.0159(10) 0.0158(10) 0.0114(9) C5 0.0369(13) 0.0534(16) 0.085(2) 0.0137(14) 0.0189(13) 0.0153(12) C6 0.072(2) 0.155(4) 0.090(3) -0.005(3) -0.001(2) 0.045(3) C7 0.082(3) 0.199(6) 0.392(12) 0.216(8) 0.127(5) 0.083(4) C8 0.075(2) 0.086(3) 0.160(4) 0.000(3) 0.011(3) 0.045(2) C11 0.0424(13) 0.0348(12) 0.0607(16) 0.0069(11) 0.0102(12) 0.0085(10) C12 0.0462(15) 0.0397(14) 0.086(2) 0.0103(13) 0.0151(14) 0.0095(11) C13 0.0442(15) 0.0520(17) 0.082(2) 0.0038(15) 0.0169(14) 0.0037(12) C14 0.0540(17) 0.0508(16) 0.0599(17) 0.0090(13) 0.0108(13) -0.0025(13) C15 0.0583(17) 0.0451(15) 0.0643(18) 0.0173(13) 0.0057(14) 0.0070(12) C16 0.0495(14) 0.0362(13) 0.0595(16) 0.0110(11) 0.0083(12) 0.0099(11) C17 0.0482(18) 0.068(2) 0.201(5) 0.055(3) 0.035(2) 0.0247(16) C18 0.071(2) 0.087(3) 0.079(2) 0.030(2) 0.0184(19) -0.0067(19) C19 0.070(2) 0.0489(16) 0.105(3) 0.0314(17) 0.0255(18) 0.0306(15) C21 0.0466(13) 0.0337(11) 0.0440(13) 0.0146(10) 0.0103(10) 0.0104(10) C22 0.0598(16) 0.0381(13) 0.0465(14) 0.0167(11) 0.0144(12) 0.0136(11) C23 0.0705(19) 0.0514(16) 0.0420(14) 0.0131(12) 0.0063(13) 0.0116(13) C24 0.0534(16) 0.0688(19) 0.0541(17) 0.0218(14) -0.0007(13) 0.0076(14) C25 0.0446(15) 0.0693(19) 0.0657(18) 0.0275(15) 0.0127(13) 0.0143(13) C26 0.0451(13) 0.0480(14) 0.0480(14) 0.0178(11) 0.0098(11) 0.0138(11) C27 0.080(2) 0.0569(17) 0.0537(16) 0.0191(13) 0.0268(15) 0.0297(15) C28 0.063(2) 0.135(4) 0.077(3) 0.030(2) -0.0103(19) 0.010(2) C29 0.0573(17) 0.080(2) 0.0512(16) 0.0156(14) 0.0184(13) 0.0269(15) C31 0.0502(14) 0.0340(12) 0.0448(13) 0.0155(10) 0.0140(11) 0.0132(10) C32 0.0610(17) 0.0530(15) 0.0509(15) 0.0207(12) 0.0203(13) 0.0216(13) F32 0.0639(11) 0.1065(15) 0.0624(10) 0.0289(10) 0.0320(9) 0.0343(10) C33 0.087(2) 0.0672(19) 0.0499(16) 0.0235(14) 0.0294(16) 0.0301(17) F33 0.1181(17) 0.1287(19) 0.0526(11) 0.0316(11) 0.0432(11) 0.0486(15) C34 0.093(2) 0.0665(19) 0.0387(15) 0.0158(13) 0.0069(15) 0.0290(17) F34 0.1277(19) 0.1224(18) 0.0435(10) 0.0206(10) 0.0035(11) 0.0540(15) C35 0.0623(18) 0.0586(17) 0.0567(17) 0.0168(13) 0.0008(14) 0.0233(14) F35 0.0711(12) 0.1117(16) 0.0701(12) 0.0204(11) -0.0079(10) 0.0390(11) C36 0.0543(15) 0.0462(14) 0.0444(14) 0.0157(11) 0.0133(12) 0.0175(12) F36 0.0504(9) 0.0770(11) 0.0570(9) 0.0217(8) 0.0140(7) 0.0277(8) C41 0.0363(12) 0.0429(13) 0.0375(12) 0.0153(10) 0.0076(9) 0.0132(10) C42 0.0419(13) 0.0470(14) 0.0436(13) 0.0151(11) 0.0097(10) 0.0163(11) F42 0.0644(10) 0.0543(9) 0.0711(10) 0.0179(8) 0.0351(8) 0.0253(8) C43 0.0392(13) 0.0631(17) 0.0446(14) 0.0214(12) 0.0151(11) 0.0137(12) F43 0.0625(10) 0.0820(12) 0.0652(10) 0.0278(9) 0.0371(8) 0.0225(9) C44 0.0410(13) 0.0528(15) 0.0474(14) 0.0269(12) 0.0089(11) 0.0083(11) F44 0.0559(9) 0.0649(10) 0.0700(10) 0.0384(8) 0.0189(8) 0.0048(8) C45 0.0433(13) 0.0427(14) 0.0550(15) 0.0202(11) 0.0056(11) 0.0132(11) F45 0.0667(10) 0.0414(8) 0.0966(13) 0.0282(8) 0.0254(9) 0.0187(7) C46 0.0392(12) 0.0439(13) 0.0432(13) 0.0162(10) 0.0111(10) 0.0140(10) F46 0.0587(9) 0.0461(8) 0.0623(9) 0.0163(7) 0.0273(7) 0.0214(7) _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 P1 C21 1.851(3) . ? P1 C11 1.860(3) . ? P1 C1 1.861(3) . ? B1 C3 1.622(4) . ? B1 C2 1.630(4) . ? B1 C31 1.638(4) . ? B1 C41 1.646(3) . ? C1 C2 1.541(3) . ? C3 N4 1.138(3) . ? N4 C5 1.468(3) . ? C5 C7 1.440(5) . ? C5 C8 1.491(5) . ? C5 C6 1.570(5) . ? C11 C12 1.403(4) . ? C11 C16 1.411(4) . ? C12 C13 1.393(4) . ? C12 C17 1.510(5) . ? C13 C14 1.373(5) . ? C14 C15 1.371(4) . ? C14 C18 1.521(4) . ? C15 C16 1.393(4) . ? C16 C19 1.509(4) . ? C21 C26 1.404(4) . ? C21 C22 1.411(4) . ? C22 C23 1.391(4) . ? C22 C27 1.514(4) . ? C23 C24 1.377(5) . ? C24 C25 1.377(4) . ? C24 C28 1.511(4) . ? C25 C26 1.390(4) . ? C26 C29 1.508(4) . ? C31 C36 1.383(4) . ? C31 C32 1.386(4) . ? C32 F32 1.349(3) . ? C32 C33 1.383(4) . ? C33 F33 1.346(3) . ? C33 C34 1.366(5) . ? C34 F34 1.341(3) . ? C34 C35 1.370(5) . ? C35 F35 1.341(4) . ? C35 C36 1.382(4) . ? C36 F36 1.351(3) . ? C41 C42 1.384(3) . ? C41 C46 1.385(3) . ? C42 F42 1.345(3) . ? C42 C43 1.384(4) . ? C43 F43 1.342(3) . ? C43 C44 1.371(4) . ? C44 F44 1.343(3) . ? C44 C45 1.372(4) . ? C45 F45 1.342(3) . ? C45 C46 1.380(3) . ? C46 F46 1.351(3) . ? 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 C21 P1 C11 103.04(11) . . ? C21 P1 C1 98.03(11) . . ? C11 P1 C1 110.54(12) . . ? C3 B1 C2 104.9(2) . . ? C3 B1 C31 110.4(2) . . ? C2 B1 C31 110.2(2) . . ? C3 B1 C41 104.37(19) . . ? C2 B1 C41 117.4(2) . . ? C31 B1 C41 109.18(19) . . ? C2 C1 P1 110.72(18) . . ? C1 C2 B1 112.2(2) . . ? N4 C3 B1 174.8(3) . . ? C3 N4 C5 175.3(3) . . ? C7 C5 N4 108.2(3) . . ? C7 C5 C8 115.6(4) . . ? N4 C5 C8 107.3(2) . . ? C7 C5 C6 112.7(5) . . ? N4 C5 C6 107.3(3) . . ? C8 C5 C6 105.3(4) . . ? C12 C11 C16 117.6(2) . . ? C12 C11 P1 125.5(2) . . ? C16 C11 P1 116.49(19) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 C17 117.2(3) . . ? C11 C12 C17 123.1(3) . . ? C14 C13 C12 122.9(3) . . ? C15 C14 C13 117.0(3) . . ? C15 C14 C18 121.2(3) . . ? C13 C14 C18 121.7(3) . . ? C14 C15 C16 122.8(3) . . ? C15 C16 C11 119.6(3) . . ? C15 C16 C19 117.2(2) . . ? C11 C16 C19 123.2(2) . . ? C26 C21 C22 118.9(2) . . ? C26 C21 P1 116.38(18) . . ? C22 C21 P1 124.7(2) . . ? C23 C22 C21 118.9(3) . . ? C23 C22 C27 116.9(2) . . ? C21 C22 C27 124.1(2) . . ? C24 C23 C22 122.7(3) . . ? C25 C24 C23 117.7(3) . . ? C25 C24 C28 120.3(3) . . ? C23 C24 C28 122.0(3) . . ? C24 C25 C26 122.4(3) . . ? C25 C26 C21 119.4(3) . . ? C25 C26 C29 117.4(2) . . ? C21 C26 C29 123.2(2) . . ? C36 C31 C32 113.5(2) . . ? C36 C31 B1 119.1(2) . . ? C32 C31 B1 127.3(2) . . ? F32 C32 C33 116.1(2) . . ? F32 C32 C31 120.1(2) . . ? C33 C32 C31 123.8(3) . . ? F33 C33 C34 120.0(3) . . ? F33 C33 C32 120.2(3) . . ? C34 C33 C32 119.8(3) . . ? F34 C34 C33 120.6(3) . . ? F34 C34 C35 120.2(3) . . ? C33 C34 C35 119.1(3) . . ? F35 C35 C34 119.9(3) . . ? F35 C35 C36 120.9(3) . . ? C34 C35 C36 119.2(3) . . ? F36 C36 C35 116.3(2) . . ? F36 C36 C31 119.3(2) . . ? C35 C36 C31 124.4(3) . . ? C42 C41 C46 114.1(2) . . ? C42 C41 B1 125.8(2) . . ? C46 C41 B1 120.1(2) . . ? F42 C42 C41 120.9(2) . . ? F42 C42 C43 115.8(2) . . ? C41 C42 C43 123.3(2) . . ? F43 C43 C44 119.8(2) . . ? F43 C43 C42 120.3(2) . . ? C44 C43 C42 119.9(2) . . ? F44 C44 C43 120.2(2) . . ? F44 C44 C45 120.5(2) . . ? C43 C44 C45 119.3(2) . . ? F45 C45 C44 119.9(2) . . ? F45 C45 C46 121.1(2) . . ? C44 C45 C46 119.1(2) . . ? F46 C46 C45 116.3(2) . . ? F46 C46 C41 119.3(2) . . ? C45 C46 C41 124.3(2) . . ? 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 C21 P1 C1 C2 64.8(2) . . . . ? C11 P1 C1 C2 171.98(18) . . . . ? P1 C1 C2 B1 -153.96(18) . . . . ? C3 B1 C2 C1 -50.7(3) . . . . ? C31 B1 C2 C1 68.1(3) . . . . ? C41 B1 C2 C1 -166.0(2) . . . . ? C2 B1 C3 N4 -29(3) . . . . ? C31 B1 C3 N4 -148(3) . . . . ? C41 B1 C3 N4 95(3) . . . . ? B1 C3 N4 C5 145(3) . . . . ? C3 N4 C5 C7 -58(3) . . . . ? C3 N4 C5 C8 67(3) . . . . ? C3 N4 C5 C6 -180(100) . . . . ? C21 P1 C11 C12 132.8(3) . . . . ? C1 P1 C11 C12 28.9(3) . . . . ? C21 P1 C11 C16 -53.9(2) . . . . ? C1 P1 C11 C16 -157.8(2) . . . . ? C16 C11 C12 C13 7.2(4) . . . . ? P1 C11 C12 C13 -179.6(2) . . . . ? C16 C11 C12 C17 -169.9(3) . . . . ? P1 C11 C12 C17 3.2(5) . . . . ? C11 C12 C13 C14 -2.9(5) . . . . ? C17 C12 C13 C14 174.4(3) . . . . ? C12 C13 C14 C15 -1.8(5) . . . . ? C12 C13 C14 C18 179.6(3) . . . . ? C13 C14 C15 C16 1.9(5) . . . . ? C18 C14 C15 C16 -179.4(3) . . . . ? C14 C15 C16 C11 2.6(4) . . . . ? C14 C15 C16 C19 -175.6(3) . . . . ? C12 C11 C16 C15 -7.1(4) . . . . ? P1 C11 C16 C15 179.1(2) . . . . ? C12 C11 C16 C19 171.0(3) . . . . ? P1 C11 C16 C19 -2.8(4) . . . . ? C11 P1 C21 C26 133.34(19) . . . . ? C1 P1 C21 C26 -113.3(2) . . . . ? C11 P1 C21 C22 -48.0(2) . . . . ? C1 P1 C21 C22 65.4(2) . . . . ? C26 C21 C22 C23 -0.3(3) . . . . ? P1 C21 C22 C23 -178.96(19) . . . . ? C26 C21 C22 C27 -178.0(2) . . . . ? P1 C21 C22 C27 3.3(4) . . . . ? C21 C22 C23 C24 -0.1(4) . . . . ? C27 C22 C23 C24 177.8(3) . . . . ? C22 C23 C24 C25 0.2(5) . . . . ? C22 C23 C24 C28 180.0(3) . . . . ? C23 C24 C25 C26 0.1(5) . . . . ? C28 C24 C25 C26 -179.7(3) . . . . ? C24 C25 C26 C21 -0.4(4) . . . . ? C24 C25 C26 C29 -179.8(3) . . . . ? C22 C21 C26 C25 0.5(4) . . . . ? P1 C21 C26 C25 179.3(2) . . . . ? C22 C21 C26 C29 179.9(2) . . . . ? P1 C21 C26 C29 -1.3(3) . . . . ? C3 B1 C31 C36 -170.4(2) . . . . ? C2 B1 C31 C36 74.2(3) . . . . ? C41 B1 C31 C36 -56.2(3) . . . . ? C3 B1 C31 C32 12.9(3) . . . . ? C2 B1 C31 C32 -102.5(3) . . . . ? C41 B1 C31 C32 127.1(3) . . . . ? C36 C31 C32 F32 -178.5(2) . . . . ? B1 C31 C32 F32 -1.7(4) . . . . ? C36 C31 C32 C33 0.8(4) . . . . ? B1 C31 C32 C33 177.7(3) . . . . ? F32 C32 C33 F33 -0.1(4) . . . . ? C31 C32 C33 F33 -179.4(3) . . . . ? F32 C32 C33 C34 -179.9(3) . . . . ? C31 C32 C33 C34 0.7(5) . . . . ? F33 C33 C34 F34 -0.2(5) . . . . ? C32 C33 C34 F34 179.7(3) . . . . ? F33 C33 C34 C35 178.8(3) . . . . ? C32 C33 C34 C35 -1.3(5) . . . . ? F34 C34 C35 F35 -0.3(5) . . . . ? C33 C34 C35 F35 -179.3(3) . . . . ? F34 C34 C35 C36 179.4(3) . . . . ? C33 C34 C35 C36 0.3(5) . . . . ? F35 C35 C36 F36 1.0(4) . . . . ? C34 C35 C36 F36 -178.7(3) . . . . ? F35 C35 C36 C31 -179.0(2) . . . . ? C34 C35 C36 C31 1.4(4) . . . . ? C32 C31 C36 F36 178.2(2) . . . . ? B1 C31 C36 F36 1.1(3) . . . . ? C32 C31 C36 C35 -1.9(4) . . . . ? B1 C31 C36 C35 -179.0(2) . . . . ? C3 B1 C41 C42 -131.5(2) . . . . ? C2 B1 C41 C42 -15.8(3) . . . . ? C31 B1 C41 C42 110.5(3) . . . . ? C3 B1 C41 C46 50.0(3) . . . . ? C2 B1 C41 C46 165.7(2) . . . . ? C31 B1 C41 C46 -68.0(3) . . . . ? C46 C41 C42 F42 179.2(2) . . . . ? B1 C41 C42 F42 0.6(4) . . . . ? C46 C41 C42 C43 -0.6(3) . . . . ? B1 C41 C42 C43 -179.1(2) . . . . ? F42 C42 C43 F43 2.1(3) . . . . ? C41 C42 C43 F43 -178.2(2) . . . . ? F42 C42 C43 C44 -179.8(2) . . . . ? C41 C42 C43 C44 -0.1(4) . . . . ? F43 C43 C44 F44 -0.2(4) . . . . ? C42 C43 C44 F44 -178.3(2) . . . . ? F43 C43 C44 C45 178.5(2) . . . . ? C42 C43 C44 C45 0.4(4) . . . . ? F44 C44 C45 F45 -0.8(4) . . . . ? C43 C44 C45 F45 -179.5(2) . . . . ? F44 C44 C45 C46 178.6(2) . . . . ? C43 C44 C45 C46 -0.1(4) . . . . ? F45 C45 C46 F46 -0.9(3) . . . . ? C44 C45 C46 F46 179.7(2) . . . . ? F45 C45 C46 C41 178.8(2) . . . . ? C44 C45 C46 C41 -0.6(4) . . . . ? C42 C41 C46 F46 -179.4(2) . . . . ? B1 C41 C46 F46 -0.7(3) . . . . ? C42 C41 C46 C45 0.9(4) . . . . ? B1 C41 C46 C45 179.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 68.10 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.742 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.048 # Attachment '- 7.cif' data_erk5221 _database_code_depnum_ccdc_archive 'CCDC 767248' #TrackingRef '- 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H35 B F10 N P' _chemical_formula_weight 725.44 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5576(1) _cell_length_b 22.3280(3) _cell_length_c 16.9958(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.650(1) _cell_angle_gamma 90.00 _cell_volume 3509.02(10) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6891 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9463 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20451 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 26.30 _reflns_number_total 6989 _reflns_number_gt 5030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS,2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+5.6367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6989 _refine_ls_number_parameters 491 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.097 _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 P1 P 0.13072(10) 0.22564(4) 0.28123(6) 0.0409(2) Uani 1 1 d . . . B1 B 0.3170(4) 0.05492(16) 0.2534(2) 0.0361(8) Uani 1 1 d . . . C1 C 0.2388(4) 0.15665(15) 0.3143(2) 0.0442(9) Uani 1 1 d . . . H1A H 0.3418 0.1667 0.3322 0.053 Uiso 1 1 calc R . . H1B H 0.2097 0.1382 0.3600 0.053 Uiso 1 1 calc R . . C2 C 0.2128(4) 0.11312(14) 0.2428(2) 0.0391(8) Uani 1 1 d . . . H2A H 0.2229 0.1353 0.1948 0.047 Uiso 1 1 calc R . . H2B H 0.1125 0.0992 0.2317 0.047 Uiso 1 1 calc R . . N1 N 0.4702(3) 0.08384(12) 0.25694(18) 0.0402(7) Uani 1 1 d . . . C3 C 0.5746(4) 0.10939(16) 0.2608(2) 0.0436(8) Uani 1 1 d . A . C4 C 0.7108(4) 0.14133(16) 0.2651(2) 0.0510(10) Uani 1 1 d D . . C5A C 0.6981(19) 0.1759(9) 0.1877(8) 0.094(5) Uani 0.301(9) 1 d PDU A 1 H5AA H 0.6837 0.1482 0.1423 0.141 Uiso 0.301(9) 1 calc PR A 1 H5AB H 0.7859 0.1987 0.1915 0.141 Uiso 0.301(9) 1 calc PR A 1 H5AC H 0.6163 0.2030 0.1793 0.141 Uiso 0.301(9) 1 calc PR A 1 C6A C 0.827(2) 0.0947(8) 0.2857(14) 0.106(7) Uani 0.301(9) 1 d PDU A 1 H6AA H 0.8406 0.0822 0.3418 0.160 Uiso 0.301(9) 1 calc PR A 1 H6AB H 0.9172 0.1114 0.2787 0.160 Uiso 0.301(9) 1 calc PR A 1 H6AC H 0.8000 0.0605 0.2501 0.160 Uiso 0.301(9) 1 calc PR A 1 C7A C 0.7230(18) 0.1854(8) 0.3364(10) 0.097(6) Uani 0.301(9) 1 d PDU A 1 H7AA H 0.6311 0.2055 0.3309 0.145 Uiso 0.301(9) 1 calc PR A 1 H7AB H 0.7973 0.2149 0.3357 0.145 Uiso 0.301(9) 1 calc PR A 1 H7AC H 0.7484 0.1636 0.3873 0.145 Uiso 0.301(9) 1 calc PR A 1 C5B C 0.7552(8) 0.1274(4) 0.1849(4) 0.083(3) Uani 0.699(9) 1 d PDU A 2 H5BA H 0.7803 0.0854 0.1838 0.125 Uiso 0.699(9) 1 calc PR A 2 H5BB H 0.8379 0.1518 0.1823 0.125 Uiso 0.699(9) 1 calc PR A 2 H5BC H 0.6750 0.1364 0.1387 0.125 Uiso 0.699(9) 1 calc PR A 2 C6B C 0.8276(8) 0.1176(4) 0.3354(5) 0.082(3) Uani 0.699(9) 1 d PDU A 2 H6BA H 0.8076 0.1298 0.3862 0.123 Uiso 0.699(9) 1 calc PR A 2 H6BB H 0.9206 0.1335 0.3324 0.123 Uiso 0.699(9) 1 calc PR A 2 H6BC H 0.8298 0.0742 0.3326 0.123 Uiso 0.699(9) 1 calc PR A 2 C7B C 0.6843(9) 0.2078(3) 0.2686(7) 0.099(3) Uani 0.699(9) 1 d PDU A 2 H7BA H 0.6047 0.2192 0.2232 0.149 Uiso 0.699(9) 1 calc PR A 2 H7BB H 0.7707 0.2294 0.2656 0.149 Uiso 0.699(9) 1 calc PR A 2 H7BC H 0.6602 0.2174 0.3193 0.149 Uiso 0.699(9) 1 calc PR A 2 C11 C 0.2651(4) 0.27403(15) 0.2497(2) 0.0423(8) Uani 1 1 d . . . C12 C 0.3855(4) 0.30028(15) 0.3041(2) 0.0444(8) Uani 1 1 d . . . C13 C 0.4774(4) 0.33696(17) 0.2745(3) 0.0519(10) Uani 1 1 d . . . H13 H 0.5564 0.3547 0.3117 0.062 Uiso 1 1 calc R . . C14 C 0.4573(5) 0.34852(18) 0.1927(3) 0.0566(10) Uani 1 1 d . . . C15 C 0.3410(5) 0.32160(18) 0.1391(3) 0.0563(11) Uani 1 1 d . . . H15 H 0.3271 0.3282 0.0830 0.068 Uiso 1 1 calc R . . C16 C 0.2436(4) 0.28503(17) 0.1656(2) 0.0507(10) Uani 1 1 d . . . C17 C 0.4207(5) 0.29030(18) 0.3944(2) 0.0541(10) Uani 1 1 d . . . H17A H 0.5129 0.3089 0.4197 0.081 Uiso 1 1 calc R . . H17B H 0.4263 0.2477 0.4056 0.081 Uiso 1 1 calc R . . H17C H 0.3457 0.3079 0.4161 0.081 Uiso 1 1 calc R . . C18 C 0.5610(5) 0.3891(2) 0.1630(3) 0.0809(15) Uani 1 1 d . . . H18A H 0.5339 0.3902 0.1040 0.121 Uiso 1 1 calc R . . H18B H 0.6587 0.3737 0.1819 0.121 Uiso 1 1 calc R . . H18C H 0.5565 0.4292 0.1842 0.121 Uiso 1 1 calc R . . C19 C 0.1164(5) 0.2601(2) 0.1019(2) 0.0671(13) Uani 1 1 d . . . H19A H 0.0280 0.2791 0.1073 0.101 Uiso 1 1 calc R . . H19B H 0.1101 0.2173 0.1095 0.101 Uiso 1 1 calc R . . H19C H 0.1297 0.2681 0.0482 0.101 Uiso 1 1 calc R . . C21 C 0.0822(4) 0.26502(14) 0.3665(2) 0.0407(8) Uani 1 1 d . . . C22 C 0.0954(4) 0.24425(16) 0.4462(2) 0.0453(9) Uani 1 1 d . . . C23 C 0.0208(4) 0.27316(18) 0.4957(3) 0.0530(10) Uani 1 1 d . . . H23 H 0.0282 0.2577 0.5481 0.064 Uiso 1 1 calc R . . C24 C -0.0637(4) 0.32335(18) 0.4717(3) 0.0545(10) Uani 1 1 d . . . C25 C -0.0720(4) 0.34501(17) 0.3948(3) 0.0525(10) Uani 1 1 d . . . H25 H -0.1259 0.3799 0.3776 0.063 Uiso 1 1 calc R . . C26 C -0.0037(4) 0.31717(15) 0.3417(2) 0.0465(9) Uani 1 1 d . . . C27 C 0.1901(5) 0.19224(18) 0.4849(2) 0.0596(11) Uani 1 1 d . . . H27A H 0.2087 0.1949 0.5436 0.089 Uiso 1 1 calc R . . H27B H 0.2810 0.1938 0.4694 0.089 Uiso 1 1 calc R . . H27C H 0.1412 0.1548 0.4664 0.089 Uiso 1 1 calc R . . C28 C -0.1424(5) 0.3538(2) 0.5280(3) 0.0733(13) Uani 1 1 d . . . H28A H -0.1089 0.3948 0.5376 0.110 Uiso 1 1 calc R . . H28B H -0.1230 0.3324 0.5793 0.110 Uiso 1 1 calc R . . H28C H -0.2456 0.3536 0.5030 0.110 Uiso 1 1 calc R . . C29 C -0.0225(5) 0.34365(18) 0.2582(3) 0.0621(12) Uani 1 1 d . . . H29A H -0.0920 0.3761 0.2506 0.093 Uiso 1 1 calc R . . H29B H -0.0572 0.3130 0.2174 0.093 Uiso 1 1 calc R . . H29C H 0.0697 0.3589 0.2527 0.093 Uiso 1 1 calc R . . C31 C 0.2696(4) 0.01101(14) 0.1734(2) 0.0373(8) Uani 1 1 d . . . C32 C 0.3500(4) -0.00441(15) 0.1195(2) 0.0444(9) Uani 1 1 d . . . F32 F 0.4896(2) 0.01317(11) 0.13243(14) 0.0590(6) Uani 1 1 d . . . C33 C 0.2972(5) -0.03814(17) 0.0500(2) 0.0518(10) Uani 1 1 d . . . F33 F 0.3807(3) -0.04981(12) -0.00117(15) 0.0750(8) Uani 1 1 d . . . C34 C 0.1587(5) -0.05908(16) 0.0328(2) 0.0550(11) Uani 1 1 d . . . F34 F 0.1040(3) -0.09088(12) -0.03540(15) 0.0806(8) Uani 1 1 d . . . C35 C 0.0741(5) -0.04617(16) 0.0844(3) 0.0521(10) Uani 1 1 d . . . F35 F -0.0632(3) -0.06596(11) 0.06801(16) 0.0693(7) Uani 1 1 d . . . C36 C 0.1305(4) -0.01245(15) 0.1531(2) 0.0430(8) Uani 1 1 d . . . F36 F 0.0419(2) -0.00266(10) 0.20256(14) 0.0548(6) Uani 1 1 d . . . C41 C 0.3410(4) 0.01323(14) 0.3353(2) 0.0384(8) Uani 1 1 d . . . C42 C 0.4607(4) -0.02327(15) 0.3591(2) 0.0450(9) Uani 1 1 d . . . F42 F 0.5638(2) -0.02240(10) 0.31689(15) 0.0595(6) Uani 1 1 d . . . C43 C 0.4847(5) -0.06230(16) 0.4241(3) 0.0562(11) Uani 1 1 d . . . F43 F 0.6055(3) -0.09591(11) 0.44305(18) 0.0826(9) Uani 1 1 d . . . C44 C 0.3864(5) -0.06534(18) 0.4697(2) 0.0581(11) Uani 1 1 d . . . F44 F 0.4090(3) -0.10305(12) 0.53384(16) 0.0876(9) Uani 1 1 d . . . C45 C 0.2653(5) -0.02999(18) 0.4497(2) 0.0544(10) Uani 1 1 d . . . F45 F 0.1687(3) -0.03265(13) 0.49489(16) 0.0821(8) Uani 1 1 d . . . C46 C 0.2450(4) 0.00768(15) 0.3836(2) 0.0442(8) Uani 1 1 d . . . F46 F 0.1207(2) 0.03948(10) 0.36747(15) 0.0587(6) 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 P1 0.0388(5) 0.0344(4) 0.0434(5) -0.0019(4) -0.0008(4) 0.0042(4) B1 0.031(2) 0.0346(19) 0.042(2) 0.0004(16) 0.0065(17) -0.0002(15) C1 0.044(2) 0.0352(18) 0.049(2) -0.0012(15) 0.0044(17) 0.0058(15) C2 0.038(2) 0.0348(17) 0.044(2) 0.0011(14) 0.0080(16) 0.0018(14) N1 0.0338(16) 0.0401(15) 0.0460(18) 0.0002(13) 0.0086(13) -0.0016(13) C3 0.036(2) 0.0448(19) 0.049(2) 0.0033(16) 0.0079(16) 0.0017(16) C4 0.029(2) 0.054(2) 0.065(3) 0.0042(19) 0.0027(17) -0.0062(16) C5A 0.061(9) 0.100(11) 0.123(12) 0.021(10) 0.028(9) -0.024(9) C6A 0.055(10) 0.112(15) 0.149(18) 0.033(14) 0.020(13) 0.000(10) C7A 0.046(9) 0.088(12) 0.158(16) 0.001(11) 0.029(11) -0.035(9) C5B 0.059(5) 0.125(7) 0.070(5) -0.011(5) 0.025(4) -0.022(5) C6B 0.037(4) 0.117(7) 0.084(6) 0.039(5) -0.002(4) -0.011(4) C7B 0.059(5) 0.050(4) 0.191(11) 0.003(5) 0.034(6) -0.013(3) C11 0.048(2) 0.0356(17) 0.0407(19) 0.0017(14) 0.0054(16) 0.0063(15) C12 0.043(2) 0.0407(18) 0.045(2) -0.0008(16) 0.0040(17) 0.0047(16) C13 0.046(2) 0.050(2) 0.058(3) -0.0002(18) 0.0110(19) 0.0031(17) C14 0.058(3) 0.048(2) 0.067(3) 0.0087(19) 0.022(2) 0.0152(19) C15 0.068(3) 0.059(2) 0.043(2) 0.0097(18) 0.016(2) 0.022(2) C16 0.055(2) 0.049(2) 0.043(2) 0.0027(17) 0.0044(18) 0.0170(18) C17 0.058(3) 0.055(2) 0.042(2) 0.0015(17) -0.0010(19) -0.0105(19) C18 0.071(3) 0.089(3) 0.096(4) 0.020(3) 0.046(3) 0.007(3) C19 0.079(3) 0.077(3) 0.034(2) -0.002(2) -0.008(2) 0.013(2) C21 0.0375(19) 0.0348(17) 0.047(2) -0.0029(14) 0.0046(16) 0.0013(14) C22 0.045(2) 0.0438(19) 0.045(2) -0.0021(16) 0.0070(17) 0.0019(16) C23 0.053(2) 0.054(2) 0.051(2) -0.0029(18) 0.0103(19) -0.0028(19) C24 0.045(2) 0.053(2) 0.065(3) -0.012(2) 0.013(2) -0.0018(18) C25 0.042(2) 0.0400(19) 0.071(3) -0.0075(18) 0.007(2) 0.0084(16) C26 0.040(2) 0.0363(18) 0.059(2) 0.0015(16) 0.0060(18) 0.0047(15) C27 0.075(3) 0.055(2) 0.046(2) 0.0068(18) 0.009(2) 0.017(2) C28 0.064(3) 0.078(3) 0.083(3) -0.016(3) 0.028(3) 0.009(2) C29 0.063(3) 0.048(2) 0.074(3) 0.018(2) 0.015(2) 0.023(2) C31 0.0379(19) 0.0325(16) 0.0407(19) 0.0009(14) 0.0083(15) 0.0028(14) C32 0.049(2) 0.0380(18) 0.046(2) 0.0028(15) 0.0113(17) 0.0025(16) F32 0.0519(14) 0.0712(15) 0.0597(15) -0.0073(12) 0.0251(12) -0.0034(11) C33 0.071(3) 0.047(2) 0.042(2) 0.0015(17) 0.022(2) 0.006(2) F33 0.097(2) 0.0805(17) 0.0546(15) -0.0094(13) 0.0334(15) 0.0041(15) C34 0.080(3) 0.0390(19) 0.040(2) -0.0025(16) 0.005(2) -0.0020(19) F34 0.112(2) 0.0714(16) 0.0491(15) -0.0170(12) 0.0030(15) -0.0106(15) C35 0.053(2) 0.042(2) 0.054(2) 0.0018(17) 0.002(2) -0.0027(17) F35 0.0572(16) 0.0648(15) 0.0748(17) -0.0048(13) -0.0035(13) -0.0177(12) C36 0.047(2) 0.0371(18) 0.044(2) 0.0025(15) 0.0099(17) 0.0015(15) F36 0.0428(13) 0.0571(13) 0.0676(15) -0.0099(11) 0.0199(11) -0.0112(10) C41 0.0388(19) 0.0301(16) 0.042(2) -0.0030(14) 0.0032(15) -0.0004(14) C42 0.051(2) 0.0353(18) 0.045(2) -0.0023(15) 0.0046(17) 0.0030(16) F42 0.0498(14) 0.0508(13) 0.0781(17) 0.0008(11) 0.0167(12) 0.0153(10) C43 0.064(3) 0.0377(19) 0.054(2) -0.0021(17) -0.010(2) 0.0045(18) F43 0.083(2) 0.0582(15) 0.090(2) 0.0136(13) -0.0099(15) 0.0256(14) C44 0.080(3) 0.047(2) 0.039(2) 0.0074(17) -0.001(2) -0.011(2) F44 0.125(3) 0.0675(16) 0.0555(16) 0.0258(13) -0.0037(16) -0.0112(16) C45 0.065(3) 0.054(2) 0.044(2) 0.0004(18) 0.013(2) -0.013(2) F45 0.102(2) 0.0899(19) 0.0625(17) 0.0124(14) 0.0348(16) -0.0180(16) C46 0.046(2) 0.0388(18) 0.046(2) -0.0006(15) 0.0080(17) -0.0020(16) F46 0.0524(14) 0.0603(13) 0.0694(16) 0.0086(11) 0.0265(12) 0.0052(11) _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 P1 C21 1.852(4) . ? P1 C11 1.858(4) . ? P1 C1 1.861(3) . ? B1 N1 1.588(5) . ? B1 C2 1.619(5) . ? B1 C41 1.642(5) . ? B1 C31 1.645(5) . ? C1 C2 1.526(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? N1 C3 1.136(4) . ? C3 C4 1.471(5) . ? C4 C6A 1.500(8) . ? C4 C5A 1.503(8) . ? C4 C7B 1.509(6) . ? C4 C6B 1.510(6) . ? C4 C7A 1.542(8) . ? C4 C5B 1.557(6) . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C5A H5AC 0.9700 . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C6A H6AC 0.9700 . ? C7A H7AA 0.9700 . ? C7A H7AB 0.9700 . ? C7A H7AC 0.9700 . ? C5B H5BA 0.9700 . ? C5B H5BB 0.9700 . ? C5B H5BC 0.9700 . ? C6B H6BA 0.9700 . ? C6B H6BB 0.9700 . ? C6B H6BC 0.9700 . ? C7B H7BA 0.9700 . ? C7B H7BB 0.9700 . ? C7B H7BC 0.9700 . ? C11 C12 1.408(5) . ? C11 C16 1.413(5) . ? C12 C13 1.385(5) . ? C12 C17 1.502(5) . ? C13 C14 1.380(6) . ? C13 H13 0.9400 . ? C14 C15 1.384(6) . ? C14 C18 1.519(6) . ? C15 C16 1.396(6) . ? C15 H15 0.9400 . ? C16 C19 1.514(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.407(5) . ? C21 C26 1.425(5) . ? C22 C23 1.392(5) . ? C22 C27 1.516(5) . ? C23 C24 1.381(6) . ? C23 H23 0.9400 . ? C24 C25 1.378(6) . ? C24 C28 1.518(6) . ? C25 C26 1.388(5) . ? C25 H25 0.9400 . ? C26 C29 1.506(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 C32 1.379(5) . ? C31 C36 1.389(5) . ? C32 F32 1.355(4) . ? C32 C33 1.385(5) . ? C33 F33 1.346(4) . ? C33 C34 1.364(6) . ? C34 F34 1.347(4) . ? C34 C35 1.366(6) . ? C35 F35 1.345(4) . ? C35 C36 1.380(5) . ? C36 F36 1.353(4) . ? C41 C42 1.380(5) . ? C41 C46 1.382(5) . ? C42 F42 1.358(4) . ? C42 C43 1.380(5) . ? C43 F43 1.346(5) . ? C43 C44 1.363(6) . ? C44 F44 1.350(4) . ? C44 C45 1.371(6) . ? C45 F45 1.343(5) . ? C45 C46 1.378(5) . ? C46 F46 1.351(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C11 106.15(16) . . ? C21 P1 C1 112.74(16) . . ? C11 P1 C1 101.37(17) . . ? N1 B1 C2 102.3(3) . . ? N1 B1 C41 105.6(3) . . ? C2 B1 C41 120.0(3) . . ? N1 B1 C31 109.4(3) . . ? C2 B1 C31 110.7(3) . . ? C41 B1 C31 108.3(3) . . ? C2 C1 P1 108.7(2) . . ? C2 C1 H1A 109.9 . . ? P1 C1 H1A 109.9 . . ? C2 C1 H1B 109.9 . . ? P1 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C1 C2 B1 116.8(3) . . ? C1 C2 H2A 108.1 . . ? B1 C2 H2A 108.1 . . ? C1 C2 H2B 108.1 . . ? B1 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? C3 N1 B1 173.7(3) . . ? N1 C3 C4 178.7(4) . . ? C3 C4 C6A 105.8(10) . . ? C3 C4 C5A 109.3(7) . . ? C6A C4 C5A 116.9(9) . . ? C3 C4 C7B 108.8(4) . . ? C6A C4 C7B 142.7(10) . . ? C5A C4 C7B 63.4(8) . . ? C3 C4 C6B 109.7(4) . . ? C6A C4 C6B 38.2(8) . . ? C5A C4 C6B 138.8(8) . . ? C7B C4 C6B 114.3(5) . . ? C3 C4 C7A 103.8(6) . . ? C6A C4 C7A 110.8(8) . . ? C5A C4 C7A 109.5(8) . . ? C7B C4 C7A 47.3(7) . . ? C6B C4 C7A 73.1(8) . . ? C3 C4 C5B 107.1(4) . . ? C6A C4 C5B 73.5(9) . . ? C5A C4 C5B 46.9(8) . . ? C7B C4 C5B 108.5(5) . . ? C6B C4 C5B 108.2(5) . . ? C7A C4 C5B 146.2(7) . . ? C4 C5A H5AA 109.5 . . ? C4 C5A H5AB 109.5 . . ? C4 C5A H5AC 109.5 . . ? C4 C6A H6AA 109.5 . . ? C4 C6A H6AB 109.5 . . ? C4 C6A H6AC 109.5 . . ? C4 C7A H7AA 109.5 . . ? C4 C7A H7AB 109.5 . . ? C4 C7A H7AC 109.5 . . ? C4 C5B H5BA 109.5 . . ? C4 C5B H5BB 109.5 . . ? H5BA C5B H5BB 109.5 . . ? C4 C5B H5BC 109.5 . . ? H5BA C5B H5BC 109.5 . . ? H5BB C5B H5BC 109.5 . . ? C4 C6B H6BA 109.5 . . ? C4 C6B H6BB 109.5 . . ? H6BA C6B H6BB 109.5 . . ? C4 C6B H6BC 109.5 . . ? H6BA C6B H6BC 109.5 . . ? H6BB C6B H6BC 109.5 . . ? C4 C7B H7BA 109.5 . . ? C4 C7B H7BB 109.5 . . ? H7BA C7B H7BB 109.5 . . ? C4 C7B H7BC 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? C12 C11 C16 118.5(4) . . ? C12 C11 P1 124.2(3) . . ? C16 C11 P1 117.3(3) . . ? C13 C12 C11 119.7(4) . . ? C13 C12 C17 117.3(3) . . ? C11 C12 C17 122.9(3) . . ? C14 C13 C12 122.5(4) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 117.8(4) . . ? C13 C14 C18 120.7(4) . . ? C15 C14 C18 121.5(4) . . ? C14 C15 C16 122.2(4) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C15 C16 C11 119.3(4) . . ? C15 C16 C19 117.7(4) . . ? C11 C16 C19 122.9(4) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 117.3(3) . . ? C22 C21 P1 128.1(3) . . ? C26 C21 P1 113.3(3) . . ? C23 C22 C21 119.6(3) . . ? C23 C22 C27 115.7(3) . . ? C21 C22 C27 124.6(3) . . ? C24 C23 C22 123.3(4) . . ? C24 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? C25 C24 C23 117.0(4) . . ? C25 C24 C28 121.4(4) . . ? C23 C24 C28 121.6(4) . . ? C24 C25 C26 122.5(4) . . ? C24 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C25 C26 C21 120.2(4) . . ? C25 C26 C29 118.3(3) . . ? C21 C26 C29 121.5(3) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 113.6(3) . . ? C32 C31 B1 127.9(3) . . ? C36 C31 B1 118.4(3) . . ? F32 C32 C31 120.8(3) . . ? F32 C32 C33 115.3(3) . . ? C31 C32 C33 123.9(4) . . ? F33 C33 C34 119.8(4) . . ? F33 C33 C32 120.6(4) . . ? C34 C33 C32 119.6(4) . . ? F34 C34 C33 120.7(4) . . ? F34 C34 C35 120.0(4) . . ? C33 C34 C35 119.3(4) . . ? F35 C35 C34 120.2(4) . . ? F35 C35 C36 120.4(4) . . ? C34 C35 C36 119.4(4) . . ? F36 C36 C35 116.2(3) . . ? F36 C36 C31 119.7(3) . . ? C35 C36 C31 124.1(4) . . ? C42 C41 C46 113.5(3) . . ? C42 C41 B1 120.7(3) . . ? C46 C41 B1 125.6(3) . . ? F42 C42 C43 115.9(3) . . ? F42 C42 C41 119.7(3) . . ? C43 C42 C41 124.4(4) . . ? F43 C43 C44 120.6(4) . . ? F43 C43 C42 120.2(4) . . ? C44 C43 C42 119.2(4) . . ? F44 C44 C43 119.9(4) . . ? F44 C44 C45 120.8(4) . . ? C43 C44 C45 119.4(4) . . ? F45 C45 C44 119.5(4) . . ? F45 C45 C46 121.2(4) . . ? C44 C45 C46 119.3(4) . . ? F46 C46 C45 114.9(4) . . ? F46 C46 C41 120.9(3) . . ? C45 C46 C41 124.2(4) . . ? 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 C21 P1 C1 C2 153.1(2) . . . . ? C11 P1 C1 C2 -93.9(3) . . . . ? P1 C1 C2 B1 169.8(2) . . . . ? N1 B1 C2 C1 -66.5(4) . . . . ? C41 B1 C2 C1 49.9(4) . . . . ? C31 B1 C2 C1 177.1(3) . . . . ? C2 B1 N1 C3 17(3) . . . . ? C41 B1 N1 C3 -110(3) . . . . ? C31 B1 N1 C3 134(3) . . . . ? B1 N1 C3 C4 -165(18) . . . . ? N1 C3 C4 C6A -38(20) . . . . ? N1 C3 C4 C5A 89(20) . . . . ? N1 C3 C4 C7B 156(20) . . . . ? N1 C3 C4 C6B -78(20) . . . . ? N1 C3 C4 C7A -154(20) . . . . ? N1 C3 C4 C5B 39(20) . . . . ? C21 P1 C11 C12 46.9(3) . . . . ? C1 P1 C11 C12 -71.0(3) . . . . ? C21 P1 C11 C16 -132.8(3) . . . . ? C1 P1 C11 C16 109.2(3) . . . . ? C16 C11 C12 C13 1.4(5) . . . . ? P1 C11 C12 C13 -178.3(3) . . . . ? C16 C11 C12 C17 -178.4(3) . . . . ? P1 C11 C12 C17 1.9(5) . . . . ? C11 C12 C13 C14 -1.0(6) . . . . ? C17 C12 C13 C14 178.8(4) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C12 C13 C14 C18 -180.0(4) . . . . ? C13 C14 C15 C16 1.6(6) . . . . ? C18 C14 C15 C16 -178.9(4) . . . . ? C14 C15 C16 C11 -1.1(6) . . . . ? C14 C15 C16 C19 177.3(4) . . . . ? C12 C11 C16 C15 -0.4(5) . . . . ? P1 C11 C16 C15 179.4(3) . . . . ? C12 C11 C16 C19 -178.8(4) . . . . ? P1 C11 C16 C19 1.0(5) . . . . ? C11 P1 C21 C22 -121.8(3) . . . . ? C1 P1 C21 C22 -11.6(4) . . . . ? C11 P1 C21 C26 71.3(3) . . . . ? C1 P1 C21 C26 -178.6(3) . . . . ? C26 C21 C22 C23 2.7(5) . . . . ? P1 C21 C22 C23 -163.7(3) . . . . ? C26 C21 C22 C27 -175.6(4) . . . . ? P1 C21 C22 C27 17.9(6) . . . . ? C21 C22 C23 C24 -2.2(6) . . . . ? C27 C22 C23 C24 176.2(4) . . . . ? C22 C23 C24 C25 -0.3(6) . . . . ? C22 C23 C24 C28 -179.5(4) . . . . ? C23 C24 C25 C26 2.2(6) . . . . ? C28 C24 C25 C26 -178.5(4) . . . . ? C24 C25 C26 C21 -1.7(6) . . . . ? C24 C25 C26 C29 178.6(4) . . . . ? C22 C21 C26 C25 -0.9(5) . . . . ? P1 C21 C26 C25 167.6(3) . . . . ? C22 C21 C26 C29 178.9(4) . . . . ? P1 C21 C26 C29 -12.7(5) . . . . ? N1 B1 C31 C32 5.4(5) . . . . ? C2 B1 C31 C32 117.4(4) . . . . ? C41 B1 C31 C32 -109.2(4) . . . . ? N1 B1 C31 C36 -171.6(3) . . . . ? C2 B1 C31 C36 -59.6(4) . . . . ? C41 B1 C31 C36 73.8(4) . . . . ? C36 C31 C32 F32 -177.6(3) . . . . ? B1 C31 C32 F32 5.3(5) . . . . ? C36 C31 C32 C33 2.3(5) . . . . ? B1 C31 C32 C33 -174.8(3) . . . . ? F32 C32 C33 F33 -2.3(5) . . . . ? C31 C32 C33 F33 177.8(3) . . . . ? F32 C32 C33 C34 178.5(3) . . . . ? C31 C32 C33 C34 -1.4(6) . . . . ? F33 C33 C34 F34 -0.6(6) . . . . ? C32 C33 C34 F34 178.6(3) . . . . ? F33 C33 C34 C35 -178.9(3) . . . . ? C32 C33 C34 C35 0.3(6) . . . . ? F34 C34 C35 F35 1.1(6) . . . . ? C33 C34 C35 F35 179.4(3) . . . . ? F34 C34 C35 C36 -178.6(3) . . . . ? C33 C34 C35 C36 -0.3(6) . . . . ? F35 C35 C36 F36 1.9(5) . . . . ? C34 C35 C36 F36 -178.4(3) . . . . ? F35 C35 C36 C31 -178.2(3) . . . . ? C34 C35 C36 C31 1.4(6) . . . . ? C32 C31 C36 F36 177.5(3) . . . . ? B1 C31 C36 F36 -5.1(5) . . . . ? C32 C31 C36 C35 -2.3(5) . . . . ? B1 C31 C36 C35 175.1(3) . . . . ? N1 B1 C41 C42 -43.8(4) . . . . ? C2 B1 C41 C42 -158.5(3) . . . . ? C31 B1 C41 C42 73.2(4) . . . . ? N1 B1 C41 C46 140.2(3) . . . . ? C2 B1 C41 C46 25.6(5) . . . . ? C31 B1 C41 C46 -102.7(4) . . . . ? C46 C41 C42 F42 179.9(3) . . . . ? B1 C41 C42 F42 3.5(5) . . . . ? C46 C41 C42 C43 0.5(5) . . . . ? B1 C41 C42 C43 -175.9(3) . . . . ? F42 C42 C43 F43 1.0(5) . . . . ? C41 C42 C43 F43 -179.6(3) . . . . ? F42 C42 C43 C44 179.5(3) . . . . ? C41 C42 C43 C44 -1.0(6) . . . . ? F43 C43 C44 F44 -1.0(6) . . . . ? C42 C43 C44 F44 -179.6(3) . . . . ? F43 C43 C44 C45 179.1(4) . . . . ? C42 C43 C44 C45 0.6(6) . . . . ? F44 C44 C45 F45 0.5(6) . . . . ? C43 C44 C45 F45 -179.6(4) . . . . ? F44 C44 C45 C46 -179.5(3) . . . . ? C43 C44 C45 C46 0.3(6) . . . . ? F45 C45 C46 F46 -1.7(5) . . . . ? C44 C45 C46 F46 178.3(3) . . . . ? F45 C45 C46 C41 179.0(3) . . . . ? C44 C45 C46 C41 -0.9(6) . . . . ? C42 C41 C46 F46 -178.7(3) . . . . ? B1 C41 C46 F46 -2.5(5) . . . . ? C42 C41 C46 C45 0.5(5) . . . . ? B1 C41 C46 C45 176.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.339 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.052 # Attachment '- 8.cif' data_erk5261 _database_code_depnum_ccdc_archive 'CCDC 767249' #TrackingRef '- 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H43 B F10 N3 P' _chemical_formula_weight 917.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8351(4) _cell_length_b 13.8395(4) _cell_length_c 21.6049(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.595(1) _cell_angle_gamma 90.00 _cell_volume 4460.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7911 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 1.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6687 _exptl_absorpt_correction_T_max 0.8852 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43759 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 67.72 _reflns_number_total 7883 _reflns_number_gt 6856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+2.0761P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7883 _refine_ls_number_parameters 592 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.28011(13) 0.58846(14) 0.31643(9) 0.0415(4) Uani 1 1 d . . . H1A H 0.2377 0.5961 0.3403 0.050 Uiso 1 1 calc R . . H1B H 0.3398 0.6057 0.3464 0.050 Uiso 1 1 calc R . . C2 C 0.25398(13) 0.65876(14) 0.25747(9) 0.0397(4) Uani 1 1 d . . . H2A H 0.2976 0.7115 0.2657 0.048 Uiso 1 1 calc R . . H2B H 0.1948 0.6867 0.2512 0.048 Uiso 1 1 calc R . . P1 P 0.25196(3) 0.59220(3) 0.18430(2) 0.03266(13) Uani 1 1 d . . . C11 C 0.33918(12) 0.60842(13) 0.14742(9) 0.0348(4) Uani 1 1 d . . . C12 C 0.42590(12) 0.63838(13) 0.18637(9) 0.0367(4) Uani 1 1 d . . . C13 C 0.49233(13) 0.64499(14) 0.15768(10) 0.0419(4) Uani 1 1 d . . . H13 H 0.5493 0.6677 0.1833 0.050 Uiso 1 1 calc R . . C14 C 0.47785(13) 0.61949(14) 0.09301(10) 0.0431(4) Uani 1 1 d . . . C15 C 0.39280(14) 0.58757(14) 0.05614(10) 0.0434(4) Uani 1 1 d . . . H15 H 0.3822 0.5691 0.0123 0.052 Uiso 1 1 calc R . . C16 C 0.32260(13) 0.58160(13) 0.08100(9) 0.0384(4) Uani 1 1 d . . . C17 C 0.45296(13) 0.66334(17) 0.25808(10) 0.0473(5) Uani 1 1 d . . . H17A H 0.5178 0.6613 0.2775 0.071 Uiso 1 1 calc R . . H17B H 0.4268 0.6171 0.2801 0.071 Uiso 1 1 calc R . . H17C H 0.4318 0.7277 0.2629 0.071 Uiso 1 1 calc R . . C18 C 0.55173(16) 0.62372(19) 0.06391(12) 0.0579(6) Uani 1 1 d . . . H18A H 0.5266 0.6153 0.0167 0.087 Uiso 1 1 calc R . . H18B H 0.5947 0.5727 0.0826 0.087 Uiso 1 1 calc R . . H18C H 0.5815 0.6859 0.0737 0.087 Uiso 1 1 calc R . . C19 C 0.23473(14) 0.54379(18) 0.03447(10) 0.0521(5) Uani 1 1 d . . . H19A H 0.1916 0.5962 0.0218 0.078 Uiso 1 1 calc R . . H19B H 0.2121 0.4936 0.0561 0.078 Uiso 1 1 calc R . . H19C H 0.2440 0.5173 -0.0043 0.078 Uiso 1 1 calc R . . C21 C 0.14226(12) 0.62210(13) 0.12499(9) 0.0367(4) Uani 1 1 d . . . C22 C 0.13142(13) 0.71985(14) 0.10565(10) 0.0423(4) Uani 1 1 d . . . C23 C 0.04735(14) 0.75198(15) 0.06683(11) 0.0494(5) Uani 1 1 d . . . H23 H 0.0406 0.8167 0.0529 0.059 Uiso 1 1 calc R . . C24 C -0.02686(13) 0.69223(16) 0.04792(10) 0.0501(5) Uani 1 1 d . . . C25 C -0.01413(13) 0.59660(16) 0.06665(10) 0.0469(5) Uani 1 1 d . . . H25 H -0.0639 0.5550 0.0535 0.056 Uiso 1 1 calc R . . C26 C 0.06843(12) 0.55852(14) 0.10397(9) 0.0400(4) Uani 1 1 d . . . C27 C 0.20575(15) 0.79377(15) 0.12487(13) 0.0587(6) Uani 1 1 d . . . H27A H 0.1851 0.8530 0.1005 0.088 Uiso 1 1 calc R . . H27B H 0.2570 0.7690 0.1149 0.088 Uiso 1 1 calc R . . H27C H 0.2230 0.8068 0.1716 0.088 Uiso 1 1 calc R . . C28 C -0.11859(15) 0.7312(2) 0.00973(14) 0.0720(8) Uani 1 1 d . . . H28A H -0.1349 0.7808 0.0353 0.108 Uiso 1 1 calc R . . H28B H -0.1621 0.6792 0.0007 0.108 Uiso 1 1 calc R . . H28C H -0.1177 0.7586 -0.0314 0.108 Uiso 1 1 calc R . . C29 C 0.07144(14) 0.45142(15) 0.11689(11) 0.0497(5) Uani 1 1 d . . . H29A H 0.0112 0.4252 0.1002 0.075 Uiso 1 1 calc R . . H29B H 0.0966 0.4398 0.1638 0.075 Uiso 1 1 calc R . . H29C H 0.1085 0.4203 0.0950 0.075 Uiso 1 1 calc R . . B1 B 0.28081(13) 0.47438(16) 0.29472(10) 0.0364(4) Uani 1 1 d . . . C31 C 0.37996(12) 0.43154(13) 0.33782(9) 0.0369(4) Uani 1 1 d . . . C32 C 0.45331(12) 0.41670(13) 0.31757(9) 0.0381(4) Uani 1 1 d . . . F32 F 0.44801(7) 0.43007(9) 0.25453(5) 0.0468(3) Uani 1 1 d . . . C33 C 0.53715(12) 0.38985(14) 0.35935(11) 0.0427(5) Uani 1 1 d . . . F33 F 0.60476(8) 0.37673(9) 0.33541(7) 0.0578(3) Uani 1 1 d . . . C34 C 0.55174(13) 0.37703(15) 0.42471(11) 0.0484(5) Uani 1 1 d . . . F34 F 0.63325(8) 0.35140(11) 0.46603(7) 0.0704(4) Uani 1 1 d . . . C35 C 0.48222(14) 0.39244(15) 0.44798(10) 0.0479(5) Uani 1 1 d . . . F35 F 0.49544(10) 0.38219(11) 0.51278(6) 0.0689(4) Uani 1 1 d . . . C36 C 0.39943(13) 0.41927(15) 0.40498(10) 0.0430(4) Uani 1 1 d . . . F36 F 0.33451(8) 0.43480(11) 0.43152(6) 0.0600(3) Uani 1 1 d . . . C41 C 0.19731(13) 0.40752(15) 0.30079(9) 0.0420(4) Uani 1 1 d . . . C42 C 0.11091(13) 0.44402(17) 0.28194(11) 0.0497(5) Uani 1 1 d . . . F42 F 0.09589(8) 0.53721(11) 0.26252(7) 0.0649(4) Uani 1 1 d . . . C43 C 0.03616(15) 0.3901(2) 0.27835(13) 0.0661(7) Uani 1 1 d . . . F43 F -0.04587(9) 0.43144(16) 0.25760(10) 0.0968(6) Uani 1 1 d . . . C44 C 0.04476(17) 0.2940(2) 0.29357(13) 0.0685(7) Uani 1 1 d . . . F44 F -0.02768(11) 0.23979(15) 0.28790(9) 0.0983(6) Uani 1 1 d . . . C45 C 0.12873(17) 0.25345(19) 0.31378(13) 0.0626(6) Uani 1 1 d . . . F45 F 0.13887(12) 0.15915(12) 0.32909(9) 0.0905(5) Uani 1 1 d . . . C46 C 0.20200(14) 0.31025(17) 0.31696(11) 0.0497(5) Uani 1 1 d . . . F46 F 0.28098(8) 0.26295(9) 0.33666(7) 0.0602(3) Uani 1 1 d . . . N3 N 0.26622(9) 0.48316(11) 0.21844(7) 0.0341(3) Uani 1 1 d . . . N4 N 0.27334(10) 0.41116(11) 0.17669(7) 0.0352(3) Uani 1 1 d . . . N5 N 0.28448(10) 0.32953(11) 0.20339(7) 0.0367(3) Uani 1 1 d . . . C51 C 0.29733(12) 0.25632(13) 0.16081(9) 0.0377(4) Uani 1 1 d . . . C52 C 0.27705(14) 0.16304(15) 0.17328(11) 0.0489(5) Uani 1 1 d . . . H52 H 0.2558 0.1503 0.2082 0.059 Uiso 1 1 calc R . . C53 C 0.28827(17) 0.08790(16) 0.13393(13) 0.0625(6) Uani 1 1 d . . . H53 H 0.2734 0.0244 0.1418 0.075 Uiso 1 1 calc R . . C54 C 0.32096(17) 0.10604(18) 0.08371(13) 0.0627(7) Uani 1 1 d . . . H54 H 0.3281 0.0551 0.0571 0.075 Uiso 1 1 calc R . . C55 C 0.34324(16) 0.19884(18) 0.07247(11) 0.0563(6) Uani 1 1 d . . . H55 H 0.3663 0.2109 0.0384 0.068 Uiso 1 1 calc R . . C56 C 0.33206(13) 0.27441(15) 0.11063(10) 0.0449(5) Uani 1 1 d . . . H56 H 0.3478 0.3376 0.1028 0.054 Uiso 1 1 calc R . . C61 C 0.6796(3) 0.1746(3) 0.60938(14) 0.0918(11) Uani 1 1 d . . . H61 H 0.6899 0.2169 0.5786 0.110 Uiso 1 1 calc R . . C62 C 0.7475(2) 0.1151(3) 0.64728(19) 0.0932(11) Uani 1 1 d . . . H62 H 0.8043 0.1163 0.6424 0.112 Uiso 1 1 calc R . . C63 C 0.7311(2) 0.0549(2) 0.69147(18) 0.0861(9) Uani 1 1 d . . . H63 H 0.7770 0.0147 0.7178 0.103 Uiso 1 1 calc R . . C64 C 0.6487(2) 0.0525(2) 0.69786(14) 0.0751(8) Uani 1 1 d . . . H64 H 0.6378 0.0101 0.7284 0.090 Uiso 1 1 calc R . . C65 C 0.5826(2) 0.1098(2) 0.66108(14) 0.0703(7) Uani 1 1 d . . . H65 H 0.5258 0.1071 0.6659 0.084 Uiso 1 1 calc R . . C66 C 0.5971(2) 0.1714(2) 0.61719(14) 0.0776(8) Uani 1 1 d . . . H66 H 0.5507 0.2120 0.5920 0.093 Uiso 1 1 calc R . . C71 C -0.0239(3) 0.5813(5) 0.3930(4) 0.157(2) Uani 1 1 d . . . H71 H -0.0818 0.5544 0.3793 0.188 Uiso 1 1 calc R . . C72 C -0.0107(3) 0.6710(4) 0.3782(2) 0.1213(15) Uani 1 1 d . . . H72 H -0.0598 0.7083 0.3528 0.146 Uiso 1 1 calc R . . C73 C 0.0682(4) 0.7087(4) 0.3979(3) 0.1259(15) Uani 1 1 d . . . H73 H 0.0753 0.7733 0.3872 0.151 Uiso 1 1 calc R . . C74 C 0.1393(3) 0.6587(4) 0.4327(2) 0.1100(12) Uani 1 1 d . . . H74 H 0.1957 0.6889 0.4465 0.132 Uiso 1 1 calc R . . C75 C 0.1334(3) 0.5697(4) 0.4485(2) 0.1099(13) Uani 1 1 d . . . H75 H 0.1851 0.5350 0.4723 0.132 Uiso 1 1 calc R . . C76 C 0.0514(5) 0.5266(3) 0.4301(4) 0.167(2) Uani 1 1 d . . . H76 H 0.0450 0.4622 0.4418 0.200 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 0.0384(10) 0.0470(11) 0.0374(10) -0.0051(8) 0.0104(8) 0.0044(8) C2 0.0344(9) 0.0399(10) 0.0417(10) -0.0056(8) 0.0088(8) 0.0048(8) P1 0.0273(2) 0.0329(2) 0.0335(2) -0.00178(18) 0.00450(18) 0.00102(17) C11 0.0320(9) 0.0317(9) 0.0377(9) 0.0008(7) 0.0077(7) 0.0007(7) C12 0.0336(9) 0.0319(9) 0.0407(10) -0.0001(8) 0.0075(8) 0.0014(7) C13 0.0320(9) 0.0416(10) 0.0489(11) -0.0022(9) 0.0094(8) -0.0016(8) C14 0.0405(10) 0.0404(10) 0.0488(11) 0.0026(9) 0.0157(9) 0.0012(8) C15 0.0458(11) 0.0464(11) 0.0372(10) -0.0008(8) 0.0130(9) 0.0005(9) C16 0.0375(10) 0.0387(10) 0.0354(9) 0.0002(8) 0.0072(8) -0.0004(8) C17 0.0326(10) 0.0608(13) 0.0430(11) -0.0108(10) 0.0053(8) -0.0054(9) C18 0.0497(13) 0.0702(15) 0.0590(13) -0.0013(12) 0.0250(11) -0.0039(11) C19 0.0452(11) 0.0707(15) 0.0372(10) -0.0103(10) 0.0094(9) -0.0098(10) C21 0.0304(9) 0.0385(10) 0.0366(9) -0.0008(8) 0.0054(7) 0.0007(7) C22 0.0344(10) 0.0399(10) 0.0459(11) 0.0023(8) 0.0047(8) 0.0005(8) C23 0.0414(11) 0.0414(11) 0.0542(12) 0.0058(9) 0.0013(9) 0.0065(9) C24 0.0360(11) 0.0557(13) 0.0473(11) -0.0017(10) -0.0009(9) 0.0057(9) C25 0.0312(10) 0.0535(12) 0.0473(11) -0.0050(9) 0.0014(8) -0.0046(8) C26 0.0343(9) 0.0436(10) 0.0375(10) -0.0021(8) 0.0059(8) -0.0024(8) C27 0.0436(12) 0.0383(11) 0.0799(16) 0.0107(11) 0.0017(11) -0.0036(9) C28 0.0400(12) 0.0721(17) 0.0813(18) -0.0003(14) -0.0095(12) 0.0106(11) C29 0.0426(11) 0.0444(11) 0.0530(12) -0.0006(9) 0.0040(9) -0.0095(9) B1 0.0304(10) 0.0448(12) 0.0341(10) 0.0004(9) 0.0111(8) 0.0033(9) C31 0.0315(9) 0.0382(10) 0.0396(10) 0.0028(8) 0.0099(8) -0.0005(7) C32 0.0342(9) 0.0372(10) 0.0415(10) 0.0006(8) 0.0109(8) 0.0008(7) F32 0.0371(6) 0.0623(7) 0.0432(6) 0.0004(5) 0.0164(5) 0.0038(5) C33 0.0289(9) 0.0388(10) 0.0587(12) 0.0024(9) 0.0123(9) 0.0023(8) F33 0.0331(6) 0.0623(8) 0.0790(9) 0.0005(7) 0.0199(6) 0.0078(5) C34 0.0325(10) 0.0439(11) 0.0555(13) 0.0087(9) -0.0027(9) 0.0008(8) F34 0.0385(7) 0.0783(9) 0.0738(9) 0.0190(7) -0.0083(6) 0.0075(6) C35 0.0457(11) 0.0511(12) 0.0380(10) 0.0097(9) 0.0023(9) -0.0047(9) F35 0.0631(8) 0.0919(10) 0.0400(7) 0.0174(7) 0.0020(6) -0.0058(7) C36 0.0379(10) 0.0504(11) 0.0400(10) 0.0040(9) 0.0119(8) -0.0017(8) F36 0.0475(7) 0.0945(10) 0.0407(6) 0.0055(6) 0.0183(5) 0.0029(7) C41 0.0334(10) 0.0559(12) 0.0374(10) -0.0007(9) 0.0127(8) -0.0012(8) C42 0.0347(10) 0.0649(14) 0.0491(12) 0.0024(10) 0.0136(9) 0.0030(9) F42 0.0394(7) 0.0740(9) 0.0774(9) 0.0048(7) 0.0144(6) 0.0150(6) C43 0.0307(11) 0.106(2) 0.0612(14) -0.0041(14) 0.0152(10) -0.0032(12) F43 0.0312(7) 0.1439(16) 0.1122(14) 0.0000(12) 0.0197(8) 0.0041(8) C44 0.0493(14) 0.098(2) 0.0611(15) -0.0017(14) 0.0227(12) -0.0278(14) F44 0.0604(9) 0.1400(16) 0.0981(12) -0.0035(11) 0.0314(9) -0.0514(10) C45 0.0601(15) 0.0698(16) 0.0611(14) 0.0039(12) 0.0247(12) -0.0180(12) F45 0.0906(12) 0.0727(10) 0.1098(13) 0.0167(9) 0.0358(10) -0.0289(9) C46 0.0420(11) 0.0600(13) 0.0482(11) 0.0044(10) 0.0165(9) -0.0051(10) F46 0.0515(7) 0.0529(7) 0.0732(8) 0.0162(6) 0.0169(6) 0.0021(6) N3 0.0326(7) 0.0349(8) 0.0328(8) -0.0024(6) 0.0083(6) 0.0030(6) N4 0.0313(7) 0.0359(8) 0.0354(8) -0.0025(6) 0.0072(6) 0.0026(6) N5 0.0349(8) 0.0336(8) 0.0393(8) -0.0008(7) 0.0092(6) 0.0025(6) C51 0.0300(9) 0.0363(10) 0.0400(10) -0.0034(8) 0.0030(7) 0.0058(7) C52 0.0473(11) 0.0396(11) 0.0559(12) -0.0001(9) 0.0120(10) 0.0038(9) C53 0.0609(14) 0.0369(11) 0.0773(17) -0.0079(11) 0.0070(13) 0.0045(10) C54 0.0615(15) 0.0577(14) 0.0590(14) -0.0182(11) 0.0071(12) 0.0167(11) C55 0.0534(13) 0.0637(15) 0.0487(12) -0.0068(11) 0.0133(10) 0.0169(11) C56 0.0388(10) 0.0480(11) 0.0456(11) -0.0022(9) 0.0111(9) 0.0075(9) C61 0.139(3) 0.088(2) 0.0524(16) -0.0121(15) 0.0379(19) -0.043(2) C62 0.072(2) 0.119(3) 0.097(2) -0.034(2) 0.0382(19) -0.027(2) C63 0.0683(18) 0.080(2) 0.093(2) -0.0062(17) 0.0044(16) 0.0058(15) C64 0.086(2) 0.0671(17) 0.0668(17) 0.0016(14) 0.0185(15) -0.0133(15) C65 0.0699(17) 0.0723(17) 0.0689(17) -0.0197(14) 0.0235(14) -0.0080(14) C66 0.093(2) 0.0642(17) 0.0565(15) -0.0144(13) -0.0004(15) 0.0067(15) C71 0.080(3) 0.143(5) 0.230(7) -0.050(5) 0.029(4) -0.033(3) C72 0.096(3) 0.150(4) 0.104(3) 0.001(3) 0.014(2) 0.034(3) C73 0.122(4) 0.116(3) 0.155(4) 0.027(3) 0.066(3) 0.006(3) C74 0.076(2) 0.133(4) 0.133(3) -0.008(3) 0.051(2) -0.006(2) C75 0.100(3) 0.124(3) 0.101(3) 0.008(3) 0.028(2) 0.044(3) C76 0.192(6) 0.067(3) 0.257(8) 0.013(3) 0.097(6) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.545(3) . ? C1 B1 1.648(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 P1 1.8206(19) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? P1 N3 1.6616(15) . ? P1 C11 1.8251(19) . ? P1 C21 1.8269(18) . ? C11 C12 1.411(3) . ? C11 C16 1.419(3) . ? C12 C13 1.392(3) . ? C12 C17 1.503(3) . ? C13 C14 1.384(3) . ? C13 H13 0.9400 . ? C14 C15 1.387(3) . ? C14 C18 1.504(3) . ? C15 C16 1.390(3) . ? C15 H15 0.9400 . ? C16 C19 1.511(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.409(3) . ? C21 C26 1.411(3) . ? C22 C23 1.387(3) . ? C22 C27 1.509(3) . ? C23 C24 1.382(3) . ? C23 H23 0.9400 . ? C24 C25 1.379(3) . ? C24 C28 1.509(3) . ? C25 C26 1.389(3) . ? C25 H25 0.9400 . ? C26 C29 1.506(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? B1 N3 1.590(2) . ? B1 C31 1.644(3) . ? B1 C41 1.655(3) . ? C31 C32 1.387(3) . ? C31 C36 1.389(3) . ? C32 F32 1.349(2) . ? C32 C33 1.383(3) . ? C33 F33 1.348(2) . ? C33 C34 1.364(3) . ? C34 F34 1.348(2) . ? C34 C35 1.372(3) . ? C35 F35 1.352(2) . ? C35 C36 1.379(3) . ? C36 F36 1.352(2) . ? C41 C42 1.385(3) . ? C41 C46 1.387(3) . ? C42 F42 1.352(3) . ? C42 C43 1.379(3) . ? C43 F43 1.351(3) . ? C43 C44 1.366(4) . ? C44 F44 1.341(3) . ? C44 C45 1.373(4) . ? C45 F45 1.343(3) . ? C45 C46 1.384(3) . ? C46 F46 1.348(2) . ? N3 N4 1.374(2) . ? N4 N5 1.254(2) . ? N5 C51 1.428(2) . ? C51 C52 1.378(3) . ? C51 C56 1.393(3) . ? C52 C53 1.392(3) . ? C52 H52 0.9400 . ? C53 C54 1.373(4) . ? C53 H53 0.9400 . ? C54 C55 1.375(4) . ? C54 H54 0.9400 . ? C55 C56 1.379(3) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? C61 C66 1.374(5) . ? C61 C62 1.383(5) . ? C61 H61 0.9400 . ? C62 C63 1.356(5) . ? C62 H62 0.9400 . ? C63 C64 1.358(4) . ? C63 H63 0.9400 . ? C64 C65 1.341(4) . ? C64 H64 0.9400 . ? C65 C66 1.351(4) . ? C65 H65 0.9400 . ? C66 H66 0.9400 . ? C71 C72 1.317(7) . ? C71 C76 1.413(8) . ? C71 H71 0.9400 . ? C72 C73 1.287(6) . ? C72 H72 0.9400 . ? C73 C74 1.321(6) . ? C73 H73 0.9400 . ? C74 C75 1.290(6) . ? C74 H74 0.9400 . ? C75 C76 1.362(7) . ? C75 H75 0.9400 . ? C76 H76 0.9400 . ? 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 C2 C1 B1 113.21(15) . . ? C2 C1 H1A 108.9 . . ? B1 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? B1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C1 C2 P1 108.62(13) . . ? C1 C2 H2A 110.0 . . ? P1 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? P1 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? N3 P1 C2 96.54(8) . . ? N3 P1 C11 107.18(8) . . ? C2 P1 C11 121.42(9) . . ? N3 P1 C21 118.21(8) . . ? C2 P1 C21 103.31(8) . . ? C11 P1 C21 110.29(8) . . ? C12 C11 C16 119.55(17) . . ? C12 C11 P1 120.22(14) . . ? C16 C11 P1 119.93(14) . . ? C13 C12 C11 118.92(17) . . ? C13 C12 C17 116.57(17) . . ? C11 C12 C17 124.51(17) . . ? C14 C13 C12 122.62(18) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C13 C14 C15 117.47(18) . . ? C13 C14 C18 121.58(19) . . ? C15 C14 C18 120.94(19) . . ? C14 C15 C16 123.06(19) . . ? C14 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C15 C16 C11 118.33(17) . . ? C15 C16 C19 116.16(17) . . ? C11 C16 C19 125.48(17) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 119.85(17) . . ? C22 C21 P1 114.71(13) . . ? C26 C21 P1 125.08(14) . . ? C23 C22 C21 118.93(18) . . ? C23 C22 C27 116.80(18) . . ? C21 C22 C27 124.27(17) . . ? C24 C23 C22 122.37(19) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C25 C24 C23 117.49(18) . . ? C25 C24 C28 121.5(2) . . ? C23 C24 C28 121.0(2) . . ? C24 C25 C26 123.43(19) . . ? C24 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C25 C26 C21 117.85(18) . . ? C25 C26 C29 116.49(17) . . ? C21 C26 C29 125.65(17) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N3 B1 C31 113.19(14) . . ? N3 B1 C1 102.08(15) . . ? C31 B1 C1 106.29(15) . . ? N3 B1 C41 106.41(15) . . ? C31 B1 C41 112.96(16) . . ? C1 B1 C41 115.56(15) . . ? C32 C31 C36 113.30(17) . . ? C32 C31 B1 128.06(17) . . ? C36 C31 B1 118.10(16) . . ? F32 C32 C33 114.65(16) . . ? F32 C32 C31 121.54(16) . . ? C33 C32 C31 123.79(18) . . ? F33 C33 C34 119.94(17) . . ? F33 C33 C32 119.86(19) . . ? C34 C33 C32 120.20(18) . . ? F34 C34 C33 120.8(2) . . ? F34 C34 C35 120.4(2) . . ? C33 C34 C35 118.77(18) . . ? F35 C35 C34 119.92(18) . . ? F35 C35 C36 120.5(2) . . ? C34 C35 C36 119.55(19) . . ? F36 C36 C35 116.32(18) . . ? F36 C36 C31 119.33(17) . . ? C35 C36 C31 124.35(19) . . ? C42 C41 C46 113.10(19) . . ? C42 C41 B1 120.62(19) . . ? C46 C41 B1 125.89(17) . . ? F42 C42 C43 116.1(2) . . ? F42 C42 C41 119.50(19) . . ? C43 C42 C41 124.3(2) . . ? F43 C43 C44 119.9(2) . . ? F43 C43 C42 120.1(3) . . ? C44 C43 C42 119.9(2) . . ? F44 C44 C43 120.6(3) . . ? F44 C44 C45 120.5(3) . . ? C43 C44 C45 118.8(2) . . ? F45 C45 C44 119.9(2) . . ? F45 C45 C46 120.7(2) . . ? C44 C45 C46 119.3(2) . . ? F46 C46 C45 114.4(2) . . ? F46 C46 C41 121.11(18) . . ? C45 C46 C41 124.5(2) . . ? N4 N3 B1 127.56(14) . . ? N4 N3 P1 113.34(11) . . ? B1 N3 P1 118.71(12) . . ? N5 N4 N3 112.42(14) . . ? N4 N5 C51 111.81(15) . . ? C52 C51 C56 119.93(18) . . ? C52 C51 N5 116.47(18) . . ? C56 C51 N5 123.54(17) . . ? C51 C52 C53 119.6(2) . . ? C51 C52 H52 120.2 . . ? C53 C52 H52 120.2 . . ? C54 C53 C52 120.4(2) . . ? C54 C53 H53 119.8 . . ? C52 C53 H53 119.8 . . ? C53 C54 C55 119.8(2) . . ? C53 C54 H54 120.1 . . ? C55 C54 H54 120.1 . . ? C54 C55 C56 120.7(2) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C55 C56 C51 119.5(2) . . ? C55 C56 H56 120.3 . . ? C51 C56 H56 120.3 . . ? C66 C61 C62 119.3(3) . . ? C66 C61 H61 120.3 . . ? C62 C61 H61 120.3 . . ? C63 C62 C61 119.3(3) . . ? C63 C62 H62 120.4 . . ? C61 C62 H62 120.4 . . ? C62 C63 C64 120.2(3) . . ? C62 C63 H63 119.9 . . ? C64 C63 H63 119.9 . . ? C65 C64 C63 120.7(3) . . ? C65 C64 H64 119.7 . . ? C63 C64 H64 119.7 . . ? C64 C65 C66 120.5(3) . . ? C64 C65 H65 119.8 . . ? C66 C65 H65 119.8 . . ? C65 C66 C61 120.0(3) . . ? C65 C66 H66 120.0 . . ? C61 C66 H66 120.0 . . ? C72 C71 C76 118.1(4) . . ? C72 C71 H71 120.9 . . ? C76 C71 H71 120.9 . . ? C73 C72 C71 121.1(5) . . ? C73 C72 H72 119.4 . . ? C71 C72 H72 119.4 . . ? C72 C73 C74 121.6(5) . . ? C72 C73 H73 119.2 . . ? C74 C73 H73 119.2 . . ? C75 C74 C73 121.9(4) . . ? C75 C74 H74 119.1 . . ? C73 C74 H74 119.1 . . ? C74 C75 C76 119.2(4) . . ? C74 C75 H75 120.4 . . ? C76 C75 H75 120.4 . . ? C75 C76 C71 118.1(4) . . ? C75 C76 H76 120.9 . . ? C71 C76 H76 120.9 . . ? 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 B1 C1 C2 P1 -10.01(19) . . . . ? C1 C2 P1 N3 7.59(14) . . . . ? C1 C2 P1 C11 -107.14(14) . . . . ? C1 C2 P1 C21 128.66(13) . . . . ? N3 P1 C11 C12 -82.57(15) . . . . ? C2 P1 C11 C12 26.60(18) . . . . ? C21 P1 C11 C12 147.49(14) . . . . ? N3 P1 C11 C16 91.08(15) . . . . ? C2 P1 C11 C16 -159.75(14) . . . . ? C21 P1 C11 C16 -38.85(17) . . . . ? C16 C11 C12 C13 2.8(3) . . . . ? P1 C11 C12 C13 176.50(14) . . . . ? C16 C11 C12 C17 -176.55(18) . . . . ? P1 C11 C12 C17 -2.9(3) . . . . ? C11 C12 C13 C14 -2.8(3) . . . . ? C17 C12 C13 C14 176.67(19) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C12 C13 C14 C18 -177.64(19) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C18 C14 C15 C16 179.4(2) . . . . ? C14 C15 C16 C11 -0.7(3) . . . . ? C14 C15 C16 C19 -179.06(19) . . . . ? C12 C11 C16 C15 -1.1(3) . . . . ? P1 C11 C16 C15 -174.84(14) . . . . ? C12 C11 C16 C19 177.00(19) . . . . ? P1 C11 C16 C19 3.3(3) . . . . ? N3 P1 C21 C22 171.05(14) . . . . ? C2 P1 C21 C22 66.01(17) . . . . ? C11 P1 C21 C22 -65.19(17) . . . . ? N3 P1 C21 C26 -2.1(2) . . . . ? C2 P1 C21 C26 -107.10(18) . . . . ? C11 P1 C21 C26 121.71(17) . . . . ? C26 C21 C22 C23 0.9(3) . . . . ? P1 C21 C22 C23 -172.55(16) . . . . ? C26 C21 C22 C27 -179.6(2) . . . . ? P1 C21 C22 C27 6.9(3) . . . . ? C21 C22 C23 C24 1.9(3) . . . . ? C27 C22 C23 C24 -177.6(2) . . . . ? C22 C23 C24 C25 -2.8(3) . . . . ? C22 C23 C24 C28 175.6(2) . . . . ? C23 C24 C25 C26 1.0(3) . . . . ? C28 C24 C25 C26 -177.4(2) . . . . ? C24 C25 C26 C21 1.7(3) . . . . ? C24 C25 C26 C29 -176.7(2) . . . . ? C22 C21 C26 C25 -2.6(3) . . . . ? P1 C21 C26 C25 170.14(15) . . . . ? C22 C21 C26 C29 175.6(2) . . . . ? P1 C21 C26 C29 -11.6(3) . . . . ? C2 C1 B1 N3 7.6(2) . . . . ? C2 C1 B1 C31 126.46(16) . . . . ? C2 C1 B1 C41 -107.36(19) . . . . ? N3 B1 C31 C32 10.2(3) . . . . ? C1 B1 C31 C32 -101.1(2) . . . . ? C41 B1 C31 C32 131.2(2) . . . . ? N3 B1 C31 C36 -178.93(17) . . . . ? C1 B1 C31 C36 69.8(2) . . . . ? C41 B1 C31 C36 -57.9(2) . . . . ? C36 C31 C32 F32 -176.73(17) . . . . ? B1 C31 C32 F32 -5.5(3) . . . . ? C36 C31 C32 C33 1.6(3) . . . . ? B1 C31 C32 C33 172.88(18) . . . . ? F32 C32 C33 F33 -1.7(3) . . . . ? C31 C32 C33 F33 179.85(17) . . . . ? F32 C32 C33 C34 178.00(18) . . . . ? C31 C32 C33 C34 -0.5(3) . . . . ? F33 C33 C34 F34 0.1(3) . . . . ? C32 C33 C34 F34 -179.62(18) . . . . ? F33 C33 C34 C35 178.89(18) . . . . ? C32 C33 C34 C35 -0.8(3) . . . . ? F34 C34 C35 F35 0.2(3) . . . . ? C33 C34 C35 F35 -178.62(19) . . . . ? F34 C34 C35 C36 179.57(19) . . . . ? C33 C34 C35 C36 0.7(3) . . . . ? F35 C35 C36 F36 0.4(3) . . . . ? C34 C35 C36 F36 -178.92(19) . . . . ? F35 C35 C36 C31 179.94(19) . . . . ? C34 C35 C36 C31 0.6(3) . . . . ? C32 C31 C36 F36 177.79(17) . . . . ? B1 C31 C36 F36 5.6(3) . . . . ? C32 C31 C36 C35 -1.7(3) . . . . ? B1 C31 C36 C35 -173.90(19) . . . . ? N3 B1 C41 C42 -71.5(2) . . . . ? C31 B1 C41 C42 163.74(18) . . . . ? C1 B1 C41 C42 41.0(3) . . . . ? N3 B1 C41 C46 100.9(2) . . . . ? C31 B1 C41 C46 -23.9(3) . . . . ? C1 B1 C41 C46 -146.6(2) . . . . ? C46 C41 C42 F42 -177.64(19) . . . . ? B1 C41 C42 F42 -4.4(3) . . . . ? C46 C41 C42 C43 -0.9(3) . . . . ? B1 C41 C42 C43 172.4(2) . . . . ? F42 C42 C43 F43 -1.3(3) . . . . ? C41 C42 C43 F43 -178.1(2) . . . . ? F42 C42 C43 C44 176.4(2) . . . . ? C41 C42 C43 C44 -0.4(4) . . . . ? F43 C43 C44 F44 0.2(4) . . . . ? C42 C43 C44 F44 -177.4(2) . . . . ? F43 C43 C44 C45 179.2(2) . . . . ? C42 C43 C44 C45 1.5(4) . . . . ? F44 C44 C45 F45 -1.1(4) . . . . ? C43 C44 C45 F45 179.9(2) . . . . ? F44 C44 C45 C46 177.7(2) . . . . ? C43 C44 C45 C46 -1.3(4) . . . . ? F45 C45 C46 F46 -0.5(3) . . . . ? C44 C45 C46 F46 -179.3(2) . . . . ? F45 C45 C46 C41 178.7(2) . . . . ? C44 C45 C46 C41 -0.2(4) . . . . ? C42 C41 C46 F46 -179.73(19) . . . . ? B1 C41 C46 F46 7.4(3) . . . . ? C42 C41 C46 C45 1.2(3) . . . . ? B1 C41 C46 C45 -171.6(2) . . . . ? C31 B1 N3 N4 56.4(2) . . . . ? C1 B1 N3 N4 170.25(15) . . . . ? C41 B1 N3 N4 -68.2(2) . . . . ? C31 B1 N3 P1 -115.86(15) . . . . ? C1 B1 N3 P1 -2.04(18) . . . . ? C41 B1 N3 P1 119.49(14) . . . . ? C2 P1 N3 N4 -176.51(12) . . . . ? C11 P1 N3 N4 -50.73(13) . . . . ? C21 P1 N3 N4 74.56(14) . . . . ? C2 P1 N3 B1 -3.16(14) . . . . ? C11 P1 N3 B1 122.62(13) . . . . ? C21 P1 N3 B1 -112.08(13) . . . . ? B1 N3 N4 N5 7.0(2) . . . . ? P1 N3 N4 N5 179.68(12) . . . . ? N3 N4 N5 C51 -176.38(14) . . . . ? N4 N5 C51 C52 -156.49(17) . . . . ? N4 N5 C51 C56 26.3(2) . . . . ? C56 C51 C52 C53 -2.4(3) . . . . ? N5 C51 C52 C53 -179.75(18) . . . . ? C51 C52 C53 C54 1.2(3) . . . . ? C52 C53 C54 C55 0.4(4) . . . . ? C53 C54 C55 C56 -0.8(4) . . . . ? C54 C55 C56 C51 -0.4(3) . . . . ? C52 C51 C56 C55 2.0(3) . . . . ? N5 C51 C56 C55 179.13(18) . . . . ? C66 C61 C62 C63 -0.1(5) . . . . ? C61 C62 C63 C64 0.7(5) . . . . ? C62 C63 C64 C65 -0.5(5) . . . . ? C63 C64 C65 C66 -0.3(4) . . . . ? C64 C65 C66 C61 0.9(4) . . . . ? C62 C61 C66 C65 -0.7(4) . . . . ? C76 C71 C72 C73 -1.3(9) . . . . ? C71 C72 C73 C74 1.1(8) . . . . ? C72 C73 C74 C75 0.4(8) . . . . ? C73 C74 C75 C76 -1.7(8) . . . . ? C74 C75 C76 C71 1.4(8) . . . . ? C72 C71 C76 C75 0.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.72 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.233 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.041 # Attachment '- 11.cif' data_erk5243 _database_code_depnum_ccdc_archive 'CCDC 767250' #TrackingRef '- 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H33 B Cl2 F10 N O P' _chemical_formula_weight 834.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0829(6) _cell_length_b 15.0592(7) _cell_length_c 19.0565(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.870(2) _cell_angle_gamma 90.00 _cell_volume 3698.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6323 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 2.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4931 _exptl_absorpt_correction_T_max 0.9222 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27107 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.48 _diffrn_reflns_theta_max 67.52 _reflns_number_total 6490 _reflns_number_gt 4687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & MInor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+5.2958P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6490 _refine_ls_number_parameters 502 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 P1 P 0.57023(7) 0.90518(6) 0.21067(5) 0.0411(3) Uani 1 1 d . . . C1 C 0.5216(3) 0.9207(3) 0.1161(2) 0.0455(9) Uani 1 1 d . . . H1A H 0.4928 0.8642 0.0963 0.055 Uiso 1 1 calc R . . H1B H 0.4644 0.9636 0.1110 0.055 Uiso 1 1 calc R . . C2 C 0.6011(3) 0.9531(3) 0.0712(2) 0.0470(9) Uani 1 1 d . . . H2A H 0.6138 1.0165 0.0803 0.056 Uiso 1 1 calc R . . H2B H 0.5714 0.9462 0.0207 0.056 Uiso 1 1 calc R . . O3 O 0.71977(19) 0.85310(15) 0.15746(13) 0.0411(6) Uani 1 1 d . . . N4 N 0.6969(2) 0.91181(19) 0.21195(16) 0.0420(7) Uani 1 1 d . . . C5 C 0.7842(3) 0.9256(2) 0.2679(2) 0.0448(9) Uani 1 1 d . . . C6 C 0.7843(3) 0.9948(3) 0.3163(2) 0.0532(10) Uani 1 1 d . . . H6 H 0.7256 1.0314 0.3144 0.064 Uiso 1 1 calc R . . C7 C 0.8720(4) 1.0095(3) 0.3677(2) 0.0612(12) Uani 1 1 d . . . H7 H 0.8723 1.0560 0.4007 0.073 Uiso 1 1 calc R . . C8 C 0.9583(4) 0.9562(3) 0.3705(3) 0.0664(13) Uani 1 1 d . . . H8 H 1.0171 0.9662 0.4055 0.080 Uiso 1 1 calc R . . C9 C 0.9585(4) 0.8885(3) 0.3221(3) 0.0604(12) Uani 1 1 d . . . H9 H 1.0179 0.8529 0.3236 0.072 Uiso 1 1 calc R . . C10 C 0.8712(3) 0.8726(3) 0.2713(2) 0.0509(10) Uani 1 1 d . . . H10 H 0.8712 0.8256 0.2388 0.061 Uiso 1 1 calc R . . C11 C 0.5092(3) 0.7994(2) 0.2273(2) 0.0436(9) Uani 1 1 d . . . C12 C 0.3998(3) 0.7990(3) 0.2140(2) 0.0491(9) Uani 1 1 d . . . C13 C 0.3491(3) 0.7189(3) 0.2182(2) 0.0544(10) Uani 1 1 d . . . H13 H 0.2761 0.7188 0.2096 0.065 Uiso 1 1 calc R . . C14 C 0.3997(3) 0.6397(3) 0.2342(2) 0.0528(10) Uani 1 1 d . . . C15 C 0.5077(3) 0.6421(3) 0.2496(2) 0.0498(10) Uani 1 1 d . . . H15 H 0.5440 0.5890 0.2622 0.060 Uiso 1 1 calc R . . C16 C 0.5639(3) 0.7204(2) 0.2472(2) 0.0430(8) Uani 1 1 d . . . C17 C 0.3306(3) 0.8796(3) 0.1950(3) 0.0676(13) Uani 1 1 d . . . H17A H 0.3147 0.8858 0.1436 0.101 Uiso 1 1 calc R . . H17B H 0.3661 0.9324 0.2155 0.101 Uiso 1 1 calc R . . H17C H 0.2667 0.8719 0.2137 0.101 Uiso 1 1 calc R . . C18 C 0.3408(4) 0.5544(3) 0.2354(3) 0.0706(13) Uani 1 1 d . . . H18A H 0.3889 0.5049 0.2407 0.106 Uiso 1 1 calc R . . H18B H 0.2920 0.5481 0.1913 0.106 Uiso 1 1 calc R . . H18C H 0.3033 0.5551 0.2752 0.106 Uiso 1 1 calc R . . C19 C 0.6800(3) 0.7153(3) 0.2682(2) 0.0533(10) Uani 1 1 d . . . H19A H 0.7121 0.7254 0.2266 0.080 Uiso 1 1 calc R . . H19B H 0.6993 0.6569 0.2876 0.080 Uiso 1 1 calc R . . H19C H 0.7034 0.7601 0.3038 0.080 Uiso 1 1 calc R . . C21 C 0.5364(3) 0.9876(3) 0.2721(2) 0.0453(9) Uani 1 1 d . . . C22 C 0.5200(4) 0.9624(3) 0.3410(2) 0.0554(10) Uani 1 1 d . . . C23 C 0.4847(4) 1.0257(3) 0.3836(2) 0.0624(12) Uani 1 1 d . . . H23 H 0.4720 1.0083 0.4287 0.075 Uiso 1 1 calc R . . C24 C 0.4672(3) 1.1131(3) 0.3634(2) 0.0557(11) Uani 1 1 d . . . C25 C 0.4894(3) 1.1376(3) 0.2979(2) 0.0494(10) Uani 1 1 d . . . H25 H 0.4812 1.1974 0.2840 0.059 Uiso 1 1 calc R . . C26 C 0.5237(3) 1.0773(2) 0.2515(2) 0.0448(9) Uani 1 1 d . . . C27 C 0.5454(6) 0.8719(3) 0.3742(3) 0.0858(18) Uani 1 1 d . . . H27A H 0.5548 0.8769 0.4256 0.129 Uiso 1 1 calc R . . H27B H 0.6088 0.8498 0.3605 0.129 Uiso 1 1 calc R . . H27C H 0.4890 0.8312 0.3577 0.129 Uiso 1 1 calc R . . C28 C 0.4315(4) 1.1794(3) 0.4128(3) 0.0725(14) Uani 1 1 d . . . H28A H 0.4896 1.1967 0.4489 0.109 Uiso 1 1 calc R . . H28B H 0.3779 1.1530 0.4355 0.109 Uiso 1 1 calc R . . H28C H 0.4039 1.2314 0.3860 0.109 Uiso 1 1 calc R . . C29 C 0.5510(4) 1.1132(3) 0.1834(2) 0.0552(11) Uani 1 1 d . . . H29A H 0.4966 1.0980 0.1440 0.083 Uiso 1 1 calc R . . H29B H 0.6161 1.0875 0.1756 0.083 Uiso 1 1 calc R . . H29C H 0.5579 1.1773 0.1868 0.083 Uiso 1 1 calc R . . B1 B 0.7112(3) 0.9008(3) 0.0871(2) 0.0419(9) Uani 1 1 d . . . C31 C 0.7194(3) 0.8213(2) 0.0281(2) 0.0429(9) Uani 1 1 d . . . C32 C 0.7458(3) 0.7332(3) 0.0407(2) 0.0518(10) Uani 1 1 d . . . F32 F 0.7658(2) 0.70038(15) 0.10787(14) 0.0727(8) Uani 1 1 d . . . C33 C 0.7559(4) 0.6723(3) -0.0117(3) 0.0644(12) Uani 1 1 d . . . F33 F 0.7828(3) 0.58757(18) 0.00489(19) 0.0967(10) Uani 1 1 d . . . C34 C 0.7376(4) 0.6977(3) -0.0817(3) 0.0628(12) Uani 1 1 d . . . F34 F 0.7450(3) 0.6391(2) -0.13391(17) 0.0903(10) Uani 1 1 d . . . C35 C 0.7116(3) 0.7847(3) -0.0983(2) 0.0564(11) Uani 1 1 d . . . F35 F 0.6949(2) 0.8117(2) -0.16640(14) 0.0803(8) Uani 1 1 d . . . C36 C 0.7050(3) 0.8431(3) -0.0437(2) 0.0465(9) Uani 1 1 d . . . F36 F 0.68473(18) 0.92886(16) -0.06371(12) 0.0578(6) Uani 1 1 d . . . C41 C 0.8153(3) 0.9651(2) 0.0859(2) 0.0433(9) Uani 1 1 d . . . C42 C 0.9140(3) 0.9281(3) 0.1017(2) 0.0481(9) Uani 1 1 d . . . F42 F 0.92436(18) 0.84088(15) 0.11933(14) 0.0604(6) Uani 1 1 d . . . C43 C 1.0048(3) 0.9725(3) 0.0986(2) 0.0575(11) Uani 1 1 d . . . F43 F 1.0966(2) 0.9302(2) 0.11293(17) 0.0818(9) Uani 1 1 d . . . C44 C 1.0008(4) 1.0610(3) 0.0796(3) 0.0622(12) Uani 1 1 d . . . F44 F 1.0880(2) 1.1062(2) 0.07680(18) 0.0906(10) Uani 1 1 d . . . C45 C 0.9063(4) 1.1011(3) 0.0631(2) 0.0598(11) Uani 1 1 d . . . F45 F 0.9005(3) 1.18713(18) 0.04364(18) 0.0879(9) Uani 1 1 d . . . C46 C 0.8169(3) 1.0530(3) 0.0657(2) 0.0505(10) Uani 1 1 d . . . F46 F 0.7289(2) 1.10003(16) 0.04583(17) 0.0751(8) Uani 1 1 d . . . C51 C 0.6528(5) 0.3052(4) 0.0203(5) 0.113(2) Uani 1 1 d . . . H51A H 0.6975 0.2557 0.0111 0.135 Uiso 1 1 calc R . . H51B H 0.6731 0.3217 0.0705 0.135 Uiso 1 1 calc R . . Cl1 Cl 0.67825(19) 0.39367(14) -0.03081(12) 0.1342(8) Uani 1 1 d . . . Cl2 Cl 0.52865(16) 0.26794(18) 0.00802(16) 0.1689(12) 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 P1 0.0420(5) 0.0360(5) 0.0450(5) 0.0021(4) 0.0069(4) 0.0018(4) C1 0.041(2) 0.045(2) 0.050(2) 0.0034(17) 0.0063(17) 0.0025(16) C2 0.051(2) 0.048(2) 0.044(2) 0.0071(17) 0.0116(17) 0.0073(18) O3 0.0444(14) 0.0376(13) 0.0413(14) 0.0007(11) 0.0075(11) 0.0034(11) N4 0.0449(18) 0.0396(16) 0.0406(17) -0.0013(13) 0.0053(14) 0.0042(13) C5 0.043(2) 0.040(2) 0.049(2) 0.0053(16) 0.0016(17) -0.0028(16) C6 0.055(3) 0.045(2) 0.057(3) -0.0029(19) 0.004(2) -0.0013(19) C7 0.066(3) 0.058(3) 0.054(3) -0.005(2) -0.003(2) -0.009(2) C8 0.061(3) 0.071(3) 0.059(3) 0.009(2) -0.014(2) -0.013(2) C9 0.052(3) 0.058(3) 0.066(3) 0.007(2) -0.003(2) -0.001(2) C10 0.046(2) 0.048(2) 0.055(2) 0.0018(18) 0.0007(19) -0.0001(18) C11 0.041(2) 0.041(2) 0.049(2) 0.0022(16) 0.0086(17) 0.0001(16) C12 0.048(2) 0.046(2) 0.054(2) 0.0030(18) 0.0098(19) 0.0031(17) C13 0.044(2) 0.055(2) 0.063(3) 0.007(2) 0.010(2) -0.0043(19) C14 0.055(3) 0.046(2) 0.058(3) -0.0005(19) 0.013(2) -0.0095(19) C15 0.058(3) 0.039(2) 0.055(2) 0.0018(17) 0.014(2) -0.0002(18) C16 0.049(2) 0.0385(19) 0.042(2) 0.0008(16) 0.0095(17) 0.0026(16) C17 0.045(2) 0.061(3) 0.099(4) 0.014(3) 0.018(2) 0.008(2) C18 0.072(3) 0.051(3) 0.090(4) 0.006(2) 0.017(3) -0.019(2) C19 0.050(2) 0.043(2) 0.066(3) 0.0104(19) 0.009(2) 0.0046(18) C21 0.045(2) 0.046(2) 0.045(2) 0.0021(17) 0.0065(17) 0.0023(17) C22 0.069(3) 0.047(2) 0.051(2) 0.0038(19) 0.012(2) 0.003(2) C23 0.083(3) 0.058(3) 0.049(2) -0.005(2) 0.021(2) -0.002(2) C24 0.060(3) 0.054(2) 0.054(3) -0.009(2) 0.013(2) -0.002(2) C25 0.050(2) 0.040(2) 0.058(3) -0.0033(18) 0.0091(19) 0.0028(17) C26 0.041(2) 0.043(2) 0.051(2) -0.0011(17) 0.0063(17) -0.0025(16) C27 0.152(6) 0.055(3) 0.051(3) 0.012(2) 0.022(3) 0.019(3) C28 0.087(4) 0.065(3) 0.071(3) -0.017(2) 0.028(3) -0.001(3) C29 0.067(3) 0.038(2) 0.062(3) 0.0026(18) 0.015(2) -0.0029(19) B1 0.043(2) 0.041(2) 0.041(2) 0.0026(18) 0.0060(18) 0.0011(18) C31 0.037(2) 0.044(2) 0.048(2) -0.0023(17) 0.0079(16) -0.0026(16) C32 0.058(3) 0.044(2) 0.054(2) -0.0012(19) 0.013(2) -0.0015(19) F32 0.109(2) 0.0427(13) 0.0671(17) 0.0062(12) 0.0175(15) 0.0114(13) C33 0.072(3) 0.041(2) 0.082(3) -0.012(2) 0.019(3) -0.001(2) F33 0.142(3) 0.0460(15) 0.106(2) -0.0141(15) 0.033(2) 0.0096(16) C34 0.057(3) 0.069(3) 0.064(3) -0.026(2) 0.016(2) -0.009(2) F34 0.099(2) 0.090(2) 0.085(2) -0.0461(17) 0.0250(17) -0.0040(17) C35 0.047(2) 0.077(3) 0.046(2) -0.009(2) 0.0088(19) -0.002(2) F35 0.0813(19) 0.114(2) 0.0463(15) -0.0081(15) 0.0122(13) 0.0132(17) C36 0.037(2) 0.051(2) 0.052(2) -0.0032(19) 0.0081(17) 0.0003(17) F36 0.0619(15) 0.0616(14) 0.0506(14) 0.0087(11) 0.0122(11) 0.0106(11) C41 0.046(2) 0.0397(19) 0.043(2) -0.0043(16) 0.0048(17) -0.0005(16) C42 0.049(2) 0.048(2) 0.048(2) -0.0062(18) 0.0097(18) -0.0016(18) F42 0.0523(14) 0.0509(13) 0.0771(17) 0.0025(12) 0.0088(12) 0.0095(11) C43 0.040(2) 0.071(3) 0.062(3) -0.010(2) 0.011(2) -0.002(2) F43 0.0426(14) 0.103(2) 0.099(2) -0.0118(17) 0.0112(14) 0.0015(14) C44 0.054(3) 0.073(3) 0.062(3) -0.016(2) 0.019(2) -0.026(2) F44 0.0708(18) 0.103(2) 0.103(2) -0.0116(18) 0.0304(17) -0.0436(17) C45 0.074(3) 0.047(2) 0.061(3) -0.003(2) 0.021(2) -0.017(2) F45 0.107(2) 0.0524(16) 0.108(2) 0.0106(15) 0.0288(19) -0.0261(15) C46 0.051(2) 0.043(2) 0.059(3) 0.0006(18) 0.010(2) -0.0015(18) F46 0.0641(16) 0.0461(14) 0.113(2) 0.0217(14) 0.0098(15) 0.0030(12) C51 0.090(5) 0.072(4) 0.174(7) 0.014(4) 0.013(5) 0.013(3) Cl1 0.1596(19) 0.1198(15) 0.1383(17) 0.0365(12) 0.0679(15) 0.0399(13) Cl2 0.1082(14) 0.178(2) 0.233(3) -0.134(2) 0.0662(16) -0.0646(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N4 1.656(3) . ? P1 C21 1.811(4) . ? P1 C1 1.821(4) . ? P1 C11 1.834(4) . ? C1 C2 1.534(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 B1 1.623(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? O3 N4 1.434(4) . ? O3 B1 1.509(5) . ? N4 C5 1.438(5) . ? C5 C10 1.383(6) . ? C5 C6 1.392(6) . ? C6 C7 1.392(6) . ? C6 H6 0.9400 . ? C7 C8 1.379(7) . ? C7 H7 0.9400 . ? C8 C9 1.376(7) . ? C8 H8 0.9400 . ? C9 C10 1.386(6) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C16 1.406(5) . ? C11 C12 1.410(5) . ? C12 C13 1.386(6) . ? C12 C17 1.520(6) . ? C13 C14 1.374(6) . ? C13 H13 0.9400 . ? C14 C15 1.393(6) . ? C14 C18 1.500(6) . ? C15 C16 1.395(5) . ? C15 H15 0.9400 . ? C16 C19 1.505(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C26 1.410(5) . ? C21 C22 1.418(6) . ? C22 C23 1.382(6) . ? C22 C27 1.515(6) . ? C23 C24 1.380(6) . ? C23 H23 0.9400 . ? C24 C25 1.380(6) . ? C24 C28 1.501(6) . ? C25 C26 1.394(6) . ? C25 H25 0.9400 . ? C26 C29 1.503(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? B1 C31 1.659(6) . ? B1 C41 1.675(6) . ? C31 C32 1.382(5) . ? C31 C36 1.387(5) . ? C32 F32 1.355(5) . ? C32 C33 1.377(6) . ? C33 F33 1.347(5) . ? C33 C34 1.369(7) . ? C34 F34 1.346(5) . ? C34 C35 1.376(7) . ? C35 F35 1.342(5) . ? C35 C36 1.377(6) . ? C36 F36 1.359(5) . ? C41 C46 1.380(5) . ? C41 C42 1.390(5) . ? C42 F42 1.357(5) . ? C42 C43 1.374(6) . ? C43 F43 1.345(5) . ? C43 C44 1.379(7) . ? C44 F44 1.337(5) . ? C44 C45 1.364(7) . ? C45 F45 1.346(5) . ? C45 C46 1.384(6) . ? C46 F46 1.349(5) . ? C51 Cl2 1.697(7) . ? C51 Cl1 1.716(7) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 P1 C21 107.68(17) . . ? N4 P1 C1 100.72(17) . . ? C21 P1 C1 117.94(18) . . ? N4 P1 C11 120.93(16) . . ? C21 P1 C11 108.78(18) . . ? C1 P1 C11 101.19(18) . . ? C2 C1 P1 115.9(3) . . ? C2 C1 H1A 108.3 . . ? P1 C1 H1A 108.3 . . ? C2 C1 H1B 108.3 . . ? P1 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C1 C2 B1 114.0(3) . . ? C1 C2 H2A 108.7 . . ? B1 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? B1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N4 O3 B1 110.9(3) . . ? O3 N4 C5 112.8(3) . . ? O3 N4 P1 106.6(2) . . ? C5 N4 P1 133.3(3) . . ? C10 C5 C6 119.6(4) . . ? C10 C5 N4 119.6(3) . . ? C6 C5 N4 120.7(3) . . ? C5 C6 C7 119.5(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.3(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 120.1(4) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 120.4(4) . . ? C5 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C16 C11 C12 120.0(3) . . ? C16 C11 P1 124.4(3) . . ? C12 C11 P1 115.5(3) . . ? C13 C12 C11 118.3(4) . . ? C13 C12 C17 115.8(4) . . ? C11 C12 C17 125.8(4) . . ? C14 C13 C12 123.4(4) . . ? C14 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C14 C15 117.2(4) . . ? C13 C14 C18 121.2(4) . . ? C15 C14 C18 121.6(4) . . ? C14 C15 C16 122.4(4) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C15 C16 C11 118.5(4) . . ? C15 C16 C19 117.5(3) . . ? C11 C16 C19 124.0(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C26 C21 C22 119.0(4) . . ? C26 C21 P1 120.5(3) . . ? C22 C21 P1 120.5(3) . . ? C23 C22 C21 118.6(4) . . ? C23 C22 C27 116.5(4) . . ? C21 C22 C27 124.7(4) . . ? C24 C23 C22 123.3(4) . . ? C24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 C24 C25 117.2(4) . . ? C23 C24 C28 120.9(4) . . ? C25 C24 C28 121.8(4) . . ? C24 C25 C26 122.7(4) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? C25 C26 C21 118.9(4) . . ? C25 C26 C29 117.6(4) . . ? C21 C26 C29 123.4(4) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 B1 C2 109.0(3) . . ? O3 B1 C31 104.8(3) . . ? C2 B1 C31 112.5(3) . . ? O3 B1 C41 110.5(3) . . ? C2 B1 C41 114.5(3) . . ? C31 B1 C41 105.1(3) . . ? C32 C31 C36 112.7(4) . . ? C32 C31 B1 128.2(4) . . ? C36 C31 B1 118.9(3) . . ? F32 C32 C33 114.5(4) . . ? F32 C32 C31 121.1(4) . . ? C33 C32 C31 124.4(4) . . ? F33 C33 C34 119.2(4) . . ? F33 C33 C32 121.0(5) . . ? C34 C33 C32 119.8(4) . . ? F34 C34 C33 121.0(5) . . ? F34 C34 C35 119.9(5) . . ? C33 C34 C35 119.0(4) . . ? F35 C35 C34 120.3(4) . . ? F35 C35 C36 121.1(4) . . ? C34 C35 C36 118.6(4) . . ? F36 C36 C35 115.4(4) . . ? F36 C36 C31 119.3(3) . . ? C35 C36 C31 125.3(4) . . ? C46 C41 C42 112.8(4) . . ? C46 C41 B1 127.5(3) . . ? C42 C41 B1 119.5(3) . . ? F42 C42 C43 115.5(4) . . ? F42 C42 C41 119.4(3) . . ? C43 C42 C41 125.0(4) . . ? F43 C43 C42 120.6(4) . . ? F43 C43 C44 120.2(4) . . ? C42 C43 C44 119.1(4) . . ? F44 C44 C45 120.7(5) . . ? F44 C44 C43 120.5(5) . . ? C45 C44 C43 118.8(4) . . ? F45 C45 C44 119.8(4) . . ? F45 C45 C46 120.3(4) . . ? C44 C45 C46 119.9(4) . . ? F46 C46 C41 121.9(4) . . ? F46 C46 C45 113.7(4) . . ? C41 C46 C45 124.4(4) . . ? Cl2 C51 Cl1 116.9(4) . . ? Cl2 C51 H51A 108.1 . . ? Cl1 C51 H51A 108.1 . . ? Cl2 C51 H51B 108.1 . . ? Cl1 C51 H51B 108.1 . . ? H51A C51 H51B 107.3 . . ? 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 N4 P1 C1 C2 -12.1(3) . . . . ? C21 P1 C1 C2 104.7(3) . . . . ? C11 P1 C1 C2 -136.9(3) . . . . ? P1 C1 C2 B1 45.8(4) . . . . ? B1 O3 N4 C5 -116.3(3) . . . . ? B1 O3 N4 P1 89.5(3) . . . . ? C21 P1 N4 O3 -173.8(2) . . . . ? C1 P1 N4 O3 -49.7(2) . . . . ? C11 P1 N4 O3 60.4(3) . . . . ? C21 P1 N4 C5 39.5(4) . . . . ? C1 P1 N4 C5 163.6(3) . . . . ? C11 P1 N4 C5 -86.3(4) . . . . ? O3 N4 C5 C10 -11.0(5) . . . . ? P1 N4 C5 C10 134.2(4) . . . . ? O3 N4 C5 C6 165.4(3) . . . . ? P1 N4 C5 C6 -49.4(5) . . . . ? C10 C5 C6 C7 -0.3(6) . . . . ? N4 C5 C6 C7 -176.7(4) . . . . ? C5 C6 C7 C8 0.3(7) . . . . ? C6 C7 C8 C9 0.4(7) . . . . ? C7 C8 C9 C10 -1.1(7) . . . . ? C6 C5 C10 C9 -0.4(6) . . . . ? N4 C5 C10 C9 176.0(4) . . . . ? C8 C9 C10 C5 1.1(7) . . . . ? N4 P1 C11 C16 5.1(4) . . . . ? C21 P1 C11 C16 -120.2(3) . . . . ? C1 P1 C11 C16 115.0(4) . . . . ? N4 P1 C11 C12 -170.6(3) . . . . ? C21 P1 C11 C12 64.1(3) . . . . ? C1 P1 C11 C12 -60.7(3) . . . . ? C16 C11 C12 C13 -2.7(6) . . . . ? P1 C11 C12 C13 173.2(3) . . . . ? C16 C11 C12 C17 177.5(4) . . . . ? P1 C11 C12 C17 -6.6(6) . . . . ? C11 C12 C13 C14 -0.4(7) . . . . ? C17 C12 C13 C14 179.5(4) . . . . ? C12 C13 C14 C15 2.7(7) . . . . ? C12 C13 C14 C18 -177.8(4) . . . . ? C13 C14 C15 C16 -1.9(6) . . . . ? C18 C14 C15 C16 178.5(4) . . . . ? C14 C15 C16 C11 -1.0(6) . . . . ? C14 C15 C16 C19 177.3(4) . . . . ? C12 C11 C16 C15 3.3(6) . . . . ? P1 C11 C16 C15 -172.2(3) . . . . ? C12 C11 C16 C19 -174.9(4) . . . . ? P1 C11 C16 C19 9.6(6) . . . . ? N4 P1 C21 C26 80.3(3) . . . . ? C1 P1 C21 C26 -32.6(4) . . . . ? C11 P1 C21 C26 -147.0(3) . . . . ? N4 P1 C21 C22 -101.1(4) . . . . ? C1 P1 C21 C22 145.9(3) . . . . ? C11 P1 C21 C22 31.6(4) . . . . ? C26 C21 C22 C23 4.7(6) . . . . ? P1 C21 C22 C23 -173.9(4) . . . . ? C26 C21 C22 C27 -170.8(5) . . . . ? P1 C21 C22 C27 10.6(7) . . . . ? C21 C22 C23 C24 -1.8(7) . . . . ? C27 C22 C23 C24 174.1(5) . . . . ? C22 C23 C24 C25 -2.0(7) . . . . ? C22 C23 C24 C28 -178.3(5) . . . . ? C23 C24 C25 C26 3.0(7) . . . . ? C28 C24 C25 C26 179.3(4) . . . . ? C24 C25 C26 C21 -0.1(6) . . . . ? C24 C25 C26 C29 -176.7(4) . . . . ? C22 C21 C26 C25 -3.8(6) . . . . ? P1 C21 C26 C25 174.8(3) . . . . ? C22 C21 C26 C29 172.6(4) . . . . ? P1 C21 C26 C29 -8.8(5) . . . . ? N4 O3 B1 C2 -49.9(4) . . . . ? N4 O3 B1 C31 -170.5(3) . . . . ? N4 O3 B1 C41 76.8(3) . . . . ? C1 C2 B1 O3 -17.5(5) . . . . ? C1 C2 B1 C31 98.3(4) . . . . ? C1 C2 B1 C41 -141.8(3) . . . . ? O3 B1 C31 C32 -10.0(5) . . . . ? C2 B1 C31 C32 -128.2(4) . . . . ? C41 B1 C31 C32 106.5(4) . . . . ? O3 B1 C31 C36 174.5(3) . . . . ? C2 B1 C31 C36 56.3(4) . . . . ? C41 B1 C31 C36 -68.9(4) . . . . ? C36 C31 C32 F32 178.1(4) . . . . ? B1 C31 C32 F32 2.4(6) . . . . ? C36 C31 C32 C33 -0.9(6) . . . . ? B1 C31 C32 C33 -176.6(4) . . . . ? F32 C32 C33 F33 0.4(7) . . . . ? C31 C32 C33 F33 179.5(4) . . . . ? F32 C32 C33 C34 179.9(4) . . . . ? C31 C32 C33 C34 -1.0(7) . . . . ? F33 C33 C34 F34 0.7(7) . . . . ? C32 C33 C34 F34 -178.8(4) . . . . ? F33 C33 C34 C35 -179.0(4) . . . . ? C32 C33 C34 C35 1.5(7) . . . . ? F34 C34 C35 F35 -0.9(6) . . . . ? C33 C34 C35 F35 178.9(4) . . . . ? F34 C34 C35 C36 -179.7(4) . . . . ? C33 C34 C35 C36 0.1(7) . . . . ? F35 C35 C36 F36 -2.3(6) . . . . ? C34 C35 C36 F36 176.5(4) . . . . ? F35 C35 C36 C31 179.0(4) . . . . ? C34 C35 C36 C31 -2.2(6) . . . . ? C32 C31 C36 F36 -176.1(3) . . . . ? B1 C31 C36 F36 0.0(5) . . . . ? C32 C31 C36 C35 2.5(6) . . . . ? B1 C31 C36 C35 178.7(4) . . . . ? O3 B1 C41 C46 -131.1(4) . . . . ? C2 B1 C41 C46 -7.6(6) . . . . ? C31 B1 C41 C46 116.4(4) . . . . ? O3 B1 C41 C42 53.8(5) . . . . ? C2 B1 C41 C42 177.3(3) . . . . ? C31 B1 C41 C42 -58.7(4) . . . . ? C46 C41 C42 F42 -177.2(4) . . . . ? B1 C41 C42 F42 -1.4(5) . . . . ? C46 C41 C42 C43 0.4(6) . . . . ? B1 C41 C42 C43 176.2(4) . . . . ? F42 C42 C43 F43 -0.4(6) . . . . ? C41 C42 C43 F43 -178.1(4) . . . . ? F42 C42 C43 C44 178.7(4) . . . . ? C41 C42 C43 C44 1.0(7) . . . . ? F43 C43 C44 F44 -1.5(7) . . . . ? C42 C43 C44 F44 179.4(4) . . . . ? F43 C43 C44 C45 177.8(4) . . . . ? C42 C43 C44 C45 -1.2(7) . . . . ? F44 C44 C45 F45 0.1(7) . . . . ? C43 C44 C45 F45 -179.2(4) . . . . ? F44 C44 C45 C46 179.4(4) . . . . ? C43 C44 C45 C46 0.1(7) . . . . ? C42 C41 C46 F46 177.6(4) . . . . ? B1 C41 C46 F46 2.3(6) . . . . ? C42 C41 C46 C45 -1.7(6) . . . . ? B1 C41 C46 C45 -177.0(4) . . . . ? F45 C45 C46 F46 1.4(6) . . . . ? C44 C45 C46 F46 -177.8(4) . . . . ? F45 C45 C46 C41 -179.2(4) . . . . ? C44 C45 C46 C41 1.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 67.52 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.587 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.061