# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kehrald@uni-muenster.de _publ_contact_author_name ' G.Kehr' loop_ _publ_author_name G.Kehr G.Erker 'R. Frohlich' A.Stute data_erk5365 _database_code_depnum_ccdc_archive 'CCDC 809019' #TrackingRef '- 4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H3 F10 P' _chemical_formula_weight 392.13 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' 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 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 19.8040(3) _cell_length_b 8.1425(1) _cell_length_c 17.4927(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.179(1) _cell_angle_gamma 90.00 _cell_volume 2804.38(7) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2563 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description pyramide _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.858 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 2.887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3566 _exptl_absorpt_correction_T_max 0.7611 _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 18878 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 67.50 _reflns_number_total 2470 _reflns_number_gt 2346 _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^)+(0.0531P)^2^+2.2396P] 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 2470 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.15520(2) 0.13407(6) 0.75466(2) 0.03916(15) Uani 1 1 d . . . C1 C 0.10085(9) -0.0350(2) 0.71998(10) 0.0441(4) Uani 1 1 d . . . H1 H 0.0783 -0.0989 0.7541 0.053 Uiso 1 1 calc R . . C2 C 0.09385(10) -0.0658(3) 0.64596(12) 0.0533(5) Uani 1 1 d . . . H2A H 0.1167 -0.0009 0.6125 0.064 Uiso 1 1 calc R . . H2B H 0.0660 -0.1528 0.6264 0.064 Uiso 1 1 calc R . . C11 C 0.21321(8) 0.0487(2) 0.83491(10) 0.0401(4) Uani 1 1 d . . . C12 C 0.22516(9) -0.1147(2) 0.85241(10) 0.0435(4) Uani 1 1 d . . . F12 F 0.19047(6) -0.23389(14) 0.81256(7) 0.0569(3) Uani 1 1 d . . . C13 C 0.27292(9) -0.1650(3) 0.91168(11) 0.0496(5) Uani 1 1 d . . . F13 F 0.28184(6) -0.32490(16) 0.92741(7) 0.0646(3) Uani 1 1 d . . . C14 C 0.30969(9) -0.0498(3) 0.95564(11) 0.0541(5) Uani 1 1 d . . . F14 F 0.35428(6) -0.0983(2) 1.01459(7) 0.0755(4) Uani 1 1 d . . . C15 C 0.29994(10) 0.1136(3) 0.93967(11) 0.0542(5) Uani 1 1 d . . . F15 F 0.33532(6) 0.2276(2) 0.98303(8) 0.0746(4) Uani 1 1 d . . . C16 C 0.25294(9) 0.1607(2) 0.88013(11) 0.0469(4) Uani 1 1 d . . . F16 F 0.24401(6) 0.32226(15) 0.86629(7) 0.0613(3) Uani 1 1 d . . . C21 C 0.09745(8) 0.2458(2) 0.81279(9) 0.0374(4) Uani 1 1 d . . . C22 C 0.06311(9) 0.1760(2) 0.87017(10) 0.0408(4) Uani 1 1 d . . . F22 F 0.07337(6) 0.01765(13) 0.88909(7) 0.0541(3) Uani 1 1 d . . . C23 C 0.01867(9) 0.2636(2) 0.90962(10) 0.0433(4) Uani 1 1 d . . . F23 F -0.01333(6) 0.19231(15) 0.96457(7) 0.0601(3) Uani 1 1 d . . . C24 C 0.00783(9) 0.4271(2) 0.89281(10) 0.0434(4) Uani 1 1 d . . . F24 F -0.03670(6) 0.51430(15) 0.92883(7) 0.0584(3) Uani 1 1 d . . . C25 C 0.04252(9) 0.5027(2) 0.83873(10) 0.0443(4) Uani 1 1 d . . . F25 F 0.03332(7) 0.66309(14) 0.82523(8) 0.0656(3) Uani 1 1 d . . . C26 C 0.08589(8) 0.4116(2) 0.79918(10) 0.0405(4) Uani 1 1 d . . . F26 F 0.11681(6) 0.48926(14) 0.74462(7) 0.0549(3) 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 0.0358(2) 0.0432(3) 0.0392(2) -0.00156(17) 0.00766(17) -0.00588(17) C1 0.0373(9) 0.0473(10) 0.0478(10) -0.0019(8) 0.0052(7) -0.0051(7) C2 0.0494(11) 0.0560(12) 0.0536(11) -0.0084(9) 0.0018(9) -0.0073(9) C11 0.0310(8) 0.0493(10) 0.0409(9) -0.0045(7) 0.0083(7) -0.0026(7) C12 0.0374(9) 0.0505(11) 0.0438(9) -0.0048(8) 0.0101(7) -0.0014(7) F12 0.0586(7) 0.0450(6) 0.0654(7) -0.0058(5) -0.0012(5) -0.0032(5) C13 0.0424(10) 0.0620(12) 0.0469(10) 0.0052(9) 0.0153(8) 0.0075(9) F13 0.0638(7) 0.0681(8) 0.0640(8) 0.0177(6) 0.0163(6) 0.0166(6) C14 0.0341(9) 0.0895(16) 0.0393(9) 0.0033(10) 0.0067(7) 0.0030(10) F14 0.0472(6) 0.1283(12) 0.0492(7) 0.0135(7) -0.0031(5) 0.0054(7) C15 0.0358(9) 0.0809(15) 0.0463(10) -0.0156(10) 0.0057(8) -0.0090(9) F15 0.0549(7) 0.1039(11) 0.0623(8) -0.0237(7) -0.0059(6) -0.0202(7) C16 0.0366(9) 0.0530(11) 0.0519(10) -0.0103(8) 0.0083(8) -0.0042(8) F16 0.0511(7) 0.0521(7) 0.0790(8) -0.0138(6) -0.0003(6) -0.0111(5) C21 0.0314(8) 0.0421(9) 0.0384(8) -0.0007(7) 0.0020(6) -0.0034(7) C22 0.0402(9) 0.0408(9) 0.0413(9) 0.0021(7) 0.0044(7) -0.0023(7) F22 0.0623(7) 0.0429(6) 0.0604(7) 0.0107(5) 0.0216(5) 0.0013(5) C23 0.0399(9) 0.0540(11) 0.0369(9) 0.0007(8) 0.0076(7) -0.0063(8) F23 0.0674(7) 0.0652(7) 0.0521(6) 0.0027(6) 0.0277(6) -0.0052(6) C24 0.0375(9) 0.0529(11) 0.0391(9) -0.0068(8) 0.0011(7) 0.0042(8) F24 0.0543(6) 0.0680(8) 0.0544(6) -0.0088(5) 0.0127(5) 0.0140(5) C25 0.0449(9) 0.0418(10) 0.0448(10) 0.0012(7) -0.0014(8) 0.0029(7) F25 0.0784(8) 0.0438(6) 0.0763(8) 0.0088(6) 0.0167(7) 0.0127(6) C26 0.0378(8) 0.0454(9) 0.0380(8) 0.0040(7) 0.0018(7) -0.0060(7) F26 0.0613(7) 0.0489(6) 0.0569(7) 0.0109(5) 0.0178(5) -0.0050(5) _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 C1 1.8113(18) . ? P1 C21 1.8494(17) . ? P1 C11 1.8511(18) . ? C1 C2 1.311(3) . ? C1 H1 0.9400 . ? C2 H2A 0.9400 . ? C2 H2B 0.9400 . ? C11 C12 1.380(3) . ? C11 C16 1.394(3) . ? C12 F12 1.341(2) . ? C12 C13 1.388(3) . ? C13 F13 1.339(2) . ? C13 C14 1.371(3) . ? C14 F14 1.343(2) . ? C14 C15 1.369(3) . ? C15 F15 1.347(2) . ? C15 C16 1.375(3) . ? C16 F16 1.346(2) . ? C21 C26 1.386(3) . ? C21 C22 1.393(2) . ? C22 F22 1.341(2) . ? C22 C23 1.375(3) . ? C23 F23 1.339(2) . ? C23 C24 1.375(3) . ? C24 F24 1.341(2) . ? C24 C25 1.373(3) . ? C25 F25 1.336(2) . ? C25 C26 1.376(3) . ? C26 F26 1.346(2) . ? 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 C1 P1 C21 100.24(8) . . ? C1 P1 C11 105.46(8) . . ? C21 P1 C11 97.92(7) . . ? C2 C1 P1 118.17(15) . . ? C2 C1 H1 120.9 . . ? P1 C1 H1 120.9 . . ? C1 C2 H2A 120.0 . . ? C1 C2 H2B 120.0 . . ? H2A C2 H2B 120.0 . . ? C12 C11 C16 115.61(17) . . ? C12 C11 P1 127.43(14) . . ? C16 C11 P1 116.81(15) . . ? F12 C12 C11 121.12(16) . . ? F12 C12 C13 116.40(17) . . ? C11 C12 C13 122.48(18) . . ? F13 C13 C14 119.97(18) . . ? F13 C13 C12 120.33(19) . . ? C14 C13 C12 119.68(19) . . ? F14 C14 C15 120.6(2) . . ? F14 C14 C13 119.7(2) . . ? C15 C14 C13 119.70(18) . . ? F15 C15 C14 120.12(19) . . ? F15 C15 C16 120.2(2) . . ? C14 C15 C16 119.68(18) . . ? F16 C16 C15 118.33(17) . . ? F16 C16 C11 118.83(17) . . ? C15 C16 C11 122.8(2) . . ? C26 C21 C22 115.93(16) . . ? C26 C21 P1 119.03(13) . . ? C22 C21 P1 125.03(14) . . ? F22 C22 C23 117.60(15) . . ? F22 C22 C21 119.85(16) . . ? C23 C22 C21 122.55(17) . . ? F23 C23 C22 120.86(17) . . ? F23 C23 C24 119.87(16) . . ? C22 C23 C24 119.26(16) . . ? F24 C24 C25 119.32(17) . . ? F24 C24 C23 120.49(17) . . ? C25 C24 C23 120.19(16) . . ? F25 C25 C24 119.41(17) . . ? F25 C25 C26 121.21(17) . . ? C24 C25 C26 119.38(17) . . ? F26 C26 C25 117.38(16) . . ? F26 C26 C21 120.01(16) . . ? C25 C26 C21 122.61(16) . . ? 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 129.10(16) . . . . ? C11 P1 C1 C2 -129.64(16) . . . . ? C1 P1 C11 C12 15.08(18) . . . . ? C21 P1 C11 C12 118.06(16) . . . . ? C1 P1 C11 C16 -169.55(13) . . . . ? C21 P1 C11 C16 -66.57(14) . . . . ? C16 C11 C12 F12 -179.51(16) . . . . ? P1 C11 C12 F12 -4.1(2) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? P1 C11 C12 C13 176.20(13) . . . . ? F12 C12 C13 F13 -1.0(2) . . . . ? C11 C12 C13 F13 178.77(16) . . . . ? F12 C12 C13 C14 -179.10(16) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? F13 C13 C14 F14 -0.3(3) . . . . ? C12 C13 C14 F14 177.81(16) . . . . ? F13 C13 C14 C15 -179.47(17) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? F14 C14 C15 F15 0.2(3) . . . . ? C13 C14 C15 F15 179.31(16) . . . . ? F14 C14 C15 C16 -178.54(16) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? F15 C15 C16 F16 0.6(3) . . . . ? C14 C15 C16 F16 179.36(17) . . . . ? F15 C15 C16 C11 -177.82(16) . . . . ? C14 C15 C16 C11 0.9(3) . . . . ? C12 C11 C16 F16 -179.99(16) . . . . ? P1 C11 C16 F16 4.1(2) . . . . ? C12 C11 C16 C15 -1.6(3) . . . . ? P1 C11 C16 C15 -177.48(15) . . . . ? C1 P1 C21 C26 -126.81(14) . . . . ? C11 P1 C21 C26 125.81(14) . . . . ? C1 P1 C21 C22 52.58(16) . . . . ? C11 P1 C21 C22 -54.79(16) . . . . ? C26 C21 C22 F22 -177.46(15) . . . . ? P1 C21 C22 F22 3.1(2) . . . . ? C26 C21 C22 C23 2.0(3) . . . . ? P1 C21 C22 C23 -177.41(13) . . . . ? F22 C22 C23 F23 -0.4(3) . . . . ? C21 C22 C23 F23 -179.86(15) . . . . ? F22 C22 C23 C24 178.78(15) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? F23 C23 C24 F24 -2.7(3) . . . . ? C22 C23 C24 F24 178.07(16) . . . . ? F23 C23 C24 C25 177.37(16) . . . . ? C22 C23 C24 C25 -1.8(3) . . . . ? F24 C24 C25 F25 2.7(3) . . . . ? C23 C24 C25 F25 -177.45(16) . . . . ? F24 C24 C25 C26 -177.02(15) . . . . ? C23 C24 C25 C26 2.9(3) . . . . ? F25 C25 C26 F26 -2.2(3) . . . . ? C24 C25 C26 F26 177.47(15) . . . . ? F25 C25 C26 C21 178.83(16) . . . . ? C24 C25 C26 C21 -1.5(3) . . . . ? C22 C21 C26 F26 -179.83(15) . . . . ? P1 C21 C26 F26 -0.4(2) . . . . ? C22 C21 C26 C25 -0.9(2) . . . . ? P1 C21 C26 C25 178.54(13) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.215 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.048 # Attachment '- 7.cif' data_erk5558 _database_code_depnum_ccdc_archive 'CCDC 809020' #TrackingRef '- 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35.75 H14.50 B Cl1.50 F20 N O P' _chemical_formula_weight 948.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 24.3493(10) _cell_length_b 8.8572(2) _cell_length_c 34.2513(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.683(3) _cell_angle_gamma 90.00 _cell_volume 7378.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6365 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3756 _exptl_absorpt_coefficient_mu 2.921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3879 _exptl_absorpt_correction_T_max 0.8677 _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 31219 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 67.30 _reflns_number_total 6421 _reflns_number_gt 5002 _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^)+(0.1006P)^2^+21.8876P] 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 6421 _refine_ls_number_parameters 561 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1846 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.054 _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 0.35425(4) 0.08921(11) 0.12365(3) 0.0453(3) Uani 1 1 d . . . B1 B 0.27909(18) -0.0895(5) 0.15681(11) 0.0435(9) Uani 1 1 d . . . O1 O 0.33901(14) -0.0895(4) 0.05908(8) 0.0702(9) Uani 1 1 d . . . N1 N 0.28738(13) -0.1376(3) 0.11305(8) 0.0453(7) Uani 1 1 d . . . C01 C 0.32393(17) -0.0667(4) 0.09179(10) 0.0506(9) Uani 1 1 d . . . C1 C 0.30191(16) 0.0898(4) 0.15863(11) 0.0474(9) Uani 1 1 d . . . H1 H 0.2717 0.1445 0.1444 0.057 Uiso 1 1 calc R . . C2 C 0.30636(19) 0.1751(5) 0.19742(12) 0.0568(10) Uani 1 1 d . . . H2A H 0.3314 0.1198 0.2155 0.068 Uiso 1 1 calc R . . H2B H 0.2701 0.1763 0.2087 0.068 Uiso 1 1 calc R . . C3 C 0.3268(2) 0.3375(5) 0.19434(14) 0.0723(13) Uani 1 1 d . . . H3A H 0.3635 0.3377 0.1844 0.108 Uiso 1 1 calc R . . H3B H 0.3277 0.3843 0.2200 0.108 Uiso 1 1 calc R . . H3C H 0.3022 0.3938 0.1767 0.108 Uiso 1 1 calc R . . C4 C 0.25614(16) -0.2593(4) 0.09466(10) 0.0469(9) Uani 1 1 d . . . C5 C 0.24721(17) -0.3909(4) 0.11486(11) 0.0526(9) Uani 1 1 d . . . H5 H 0.2631 -0.4034 0.1402 0.063 Uiso 1 1 calc R . . C6 C 0.21522(18) -0.5041(5) 0.09832(13) 0.0574(10) Uani 1 1 d . . . H6 H 0.2094 -0.5930 0.1125 0.069 Uiso 1 1 calc R . . C7 C 0.19131(16) -0.4889(5) 0.06073(12) 0.0562(10) Uani 1 1 d . . . C8 C 0.19987(18) -0.3570(5) 0.04098(12) 0.0588(10) Uani 1 1 d . . . H8 H 0.1839 -0.3448 0.0157 0.071 Uiso 1 1 calc R . . C9 C 0.23158(17) -0.2410(5) 0.05740(11) 0.0548(10) Uani 1 1 d . . . H9 H 0.2364 -0.1508 0.0435 0.066 Uiso 1 1 calc R . . C10 C 0.1578(2) -0.6153(6) 0.04218(16) 0.0737(13) Uani 1 1 d . . . H10A H 0.1384 -0.5786 0.0186 0.111 Uiso 1 1 calc R . . H10B H 0.1313 -0.6510 0.0604 0.111 Uiso 1 1 calc R . . H10C H 0.1819 -0.6975 0.0356 0.111 Uiso 1 1 calc R . . C11 C 0.42449(17) 0.0322(5) 0.13557(12) 0.0577(10) Uani 1 1 d . . . C12 C 0.44860(17) 0.0125(5) 0.17252(12) 0.0575(10) Uani 1 1 d . . . F12 F 0.41973(10) 0.0441(3) 0.20371(7) 0.0708(7) Uani 1 1 d . . . C13 C 0.5011(2) -0.0385(6) 0.17889(15) 0.0701(12) Uani 1 1 d . . . F13 F 0.52227(13) -0.0586(4) 0.21494(9) 0.0981(10) Uani 1 1 d . . . C14 C 0.5317(2) -0.0705(8) 0.14836(18) 0.0915(18) Uani 1 1 d . . . F14 F 0.58401(15) -0.1158(6) 0.15408(13) 0.1398(17) Uani 1 1 d . . . C15 C 0.5108(2) -0.0512(10) 0.11159(18) 0.110(2) Uani 1 1 d . . . F15 F 0.54139(17) -0.0809(9) 0.08084(13) 0.195(3) Uani 1 1 d . . . C16 C 0.4581(2) -0.0005(8) 0.10501(15) 0.0893(18) Uani 1 1 d . . . F16 F 0.44031(13) 0.0259(6) 0.06811(8) 0.1293(17) Uani 1 1 d . . . C21 C 0.35870(16) 0.2579(4) 0.09450(10) 0.0474(9) Uani 1 1 d . . . C22 C 0.39986(18) 0.3653(5) 0.10009(12) 0.0586(10) Uani 1 1 d . . . F22 F 0.43703(11) 0.3501(3) 0.12994(8) 0.0750(7) Uani 1 1 d . . . C23 C 0.4041(2) 0.4881(5) 0.07565(15) 0.0689(13) Uani 1 1 d . . . F23 F 0.44458(14) 0.5876(4) 0.08213(11) 0.0999(11) Uani 1 1 d . . . C24 C 0.3661(2) 0.5040(5) 0.04460(14) 0.0702(13) Uani 1 1 d . . . F24 F 0.37139(16) 0.6204(4) 0.02028(10) 0.1039(11) Uani 1 1 d . . . C25 C 0.3253(2) 0.4028(5) 0.03856(12) 0.0611(11) Uani 1 1 d . . . F25 F 0.28903(12) 0.4205(3) 0.00812(7) 0.0806(8) Uani 1 1 d . . . C26 C 0.32098(17) 0.2827(5) 0.06337(11) 0.0530(10) Uani 1 1 d . . . F26 F 0.27851(10) 0.1893(3) 0.05745(7) 0.0662(7) Uani 1 1 d . . . C31 C 0.31863(16) -0.1860(4) 0.18852(10) 0.0451(8) Uani 1 1 d . . . C32 C 0.31237(17) -0.1715(4) 0.22872(11) 0.0500(9) Uani 1 1 d . . . F32 F 0.27027(10) -0.0897(3) 0.24163(6) 0.0593(6) Uani 1 1 d . . . C33 C 0.34665(19) -0.2366(5) 0.25705(11) 0.0607(11) Uani 1 1 d . . . F33 F 0.33635(13) -0.2193(4) 0.29504(7) 0.0834(9) Uani 1 1 d . . . C34 C 0.3908(2) -0.3191(5) 0.24624(14) 0.0666(13) Uani 1 1 d . . . F34 F 0.42551(13) -0.3815(4) 0.27349(9) 0.0946(10) Uani 1 1 d . . . C35 C 0.39980(17) -0.3376(5) 0.20738(14) 0.0608(11) Uani 1 1 d . . . F35 F 0.44294(12) -0.4175(3) 0.19594(10) 0.0855(9) Uani 1 1 d . . . C36 C 0.36357(16) -0.2734(4) 0.17970(11) 0.0507(9) Uani 1 1 d . . . F36 F 0.37524(10) -0.3009(3) 0.14219(7) 0.0656(6) Uani 1 1 d . . . C41 C 0.21260(16) -0.1033(4) 0.16321(10) 0.0473(9) Uani 1 1 d . . . C42 C 0.18735(17) -0.2133(5) 0.18541(11) 0.0559(10) Uani 1 1 d . . . F42 F 0.21757(10) -0.3187(3) 0.20504(7) 0.0667(7) Uani 1 1 d . . . C43 C 0.1314(2) -0.2284(6) 0.18826(14) 0.0701(13) Uani 1 1 d . . . F43 F 0.11110(13) -0.3380(5) 0.21058(10) 0.1029(11) Uani 1 1 d . . . C44 C 0.0969(2) -0.1345(7) 0.16762(18) 0.0812(15) Uani 1 1 d . . . F44 F 0.04242(12) -0.1490(5) 0.16977(13) 0.1235(14) Uani 1 1 d . . . C45 C 0.1185(2) -0.0262(6) 0.14460(16) 0.0755(14) Uani 1 1 d . . . F45 F 0.08535(14) 0.0671(4) 0.12317(13) 0.1155(13) Uani 1 1 d . . . C46 C 0.17466(18) -0.0134(5) 0.14271(13) 0.0587(11) Uani 1 1 d . . . F46 F 0.19255(12) 0.0930(3) 0.11794(9) 0.0810(8) Uani 1 1 d . . . C100 C 0.4701(6) -0.2112(18) -0.0181(4) 0.163(5) Uani 0.75 1 d PU . . H10D H 0.4753 -0.1017 -0.0197 0.195 Uiso 0.75 1 calc PR . . H10E H 0.4386 -0.2295 -0.0020 0.195 Uiso 0.75 1 calc PR . . Cl1 Cl 0.45464(18) -0.2775(6) -0.06376(14) 0.1996(18) Uani 0.75 1 d PU . . Cl2 Cl 0.52554(18) -0.2865(7) 0.00402(13) 0.215(2) Uani 0.75 1 d PU . . 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 0.0504(5) 0.0517(5) 0.0335(5) -0.0004(4) -0.0003(4) -0.0004(4) B1 0.052(2) 0.044(2) 0.0338(19) -0.0012(17) -0.0032(17) -0.0029(18) O1 0.093(2) 0.080(2) 0.0394(15) -0.0131(14) 0.0134(14) -0.0108(17) N1 0.0603(19) 0.0437(16) 0.0314(14) -0.0009(12) -0.0033(13) 0.0020(14) C01 0.066(2) 0.051(2) 0.0353(19) -0.0022(16) -0.0010(17) 0.0018(19) C1 0.055(2) 0.047(2) 0.0406(19) -0.0008(16) 0.0049(16) -0.0004(17) C2 0.071(3) 0.055(2) 0.045(2) -0.0077(18) 0.0078(19) -0.005(2) C3 0.105(4) 0.054(3) 0.059(3) -0.012(2) 0.015(3) -0.013(2) C4 0.058(2) 0.046(2) 0.0364(18) -0.0064(15) -0.0032(16) 0.0044(17) C5 0.068(3) 0.047(2) 0.042(2) -0.0025(16) -0.0051(18) 0.0036(19) C6 0.068(3) 0.046(2) 0.058(2) -0.0054(18) 0.002(2) 0.0009(19) C7 0.051(2) 0.060(3) 0.057(2) -0.018(2) 0.0000(18) 0.0049(19) C8 0.061(2) 0.071(3) 0.043(2) -0.010(2) -0.0073(18) 0.003(2) C9 0.067(3) 0.056(2) 0.041(2) -0.0037(18) -0.0066(18) 0.004(2) C10 0.062(3) 0.078(3) 0.081(3) -0.030(3) -0.002(2) -0.005(2) C11 0.056(2) 0.066(3) 0.050(2) -0.002(2) -0.0034(18) 0.002(2) C12 0.059(2) 0.058(2) 0.055(2) -0.0043(19) -0.0049(19) -0.002(2) F12 0.0649(15) 0.1009(19) 0.0458(13) -0.0038(13) -0.0045(11) -0.0079(14) C13 0.066(3) 0.069(3) 0.073(3) 0.001(2) -0.019(2) 0.006(2) F13 0.084(2) 0.125(3) 0.082(2) 0.0136(19) -0.0294(16) 0.0041(19) C14 0.068(3) 0.119(5) 0.086(4) -0.021(3) -0.014(3) 0.032(3) F14 0.081(2) 0.194(4) 0.141(3) -0.044(3) -0.028(2) 0.065(3) C15 0.075(4) 0.176(7) 0.078(4) -0.039(4) 0.005(3) 0.045(4) F15 0.095(3) 0.391(9) 0.101(3) -0.080(4) 0.011(2) 0.093(4) C16 0.069(3) 0.143(5) 0.055(3) -0.020(3) 0.002(2) 0.029(3) F16 0.077(2) 0.262(5) 0.0489(16) -0.024(2) 0.0045(14) 0.040(3) C21 0.053(2) 0.053(2) 0.0365(18) 0.0002(16) 0.0058(16) -0.0028(17) C22 0.063(2) 0.069(3) 0.045(2) -0.0025(19) 0.0078(19) -0.009(2) F22 0.0664(16) 0.0919(19) 0.0661(16) -0.0044(14) -0.0041(13) -0.0254(14) C23 0.074(3) 0.065(3) 0.071(3) -0.003(2) 0.032(2) -0.016(2) F23 0.102(2) 0.088(2) 0.113(3) -0.0016(18) 0.0373(19) -0.0394(18) C24 0.095(4) 0.061(3) 0.057(3) 0.014(2) 0.029(3) 0.011(3) F24 0.141(3) 0.079(2) 0.095(2) 0.0386(17) 0.046(2) 0.0102(19) C25 0.076(3) 0.064(3) 0.044(2) 0.0044(19) 0.015(2) 0.015(2) F25 0.100(2) 0.0909(19) 0.0507(14) 0.0161(13) 0.0028(14) 0.0346(16) C26 0.062(2) 0.058(2) 0.0389(19) -0.0016(17) 0.0042(17) 0.007(2) F26 0.0654(15) 0.0745(16) 0.0571(14) 0.0035(12) -0.0152(11) -0.0033(13) C31 0.053(2) 0.0422(19) 0.0396(18) 0.0013(15) -0.0048(16) -0.0086(16) C32 0.057(2) 0.052(2) 0.0404(19) 0.0038(16) -0.0065(17) -0.0132(18) F32 0.0706(15) 0.0702(15) 0.0372(11) -0.0047(10) 0.0030(10) -0.0077(12) C33 0.071(3) 0.068(3) 0.041(2) 0.0123(19) -0.0126(19) -0.021(2) F33 0.100(2) 0.108(2) 0.0405(13) 0.0165(13) -0.0162(13) -0.0273(17) C34 0.069(3) 0.062(3) 0.065(3) 0.021(2) -0.030(2) -0.016(2) F34 0.093(2) 0.099(2) 0.088(2) 0.0366(17) -0.0430(17) -0.0049(17) C35 0.052(2) 0.053(2) 0.075(3) 0.006(2) -0.017(2) 0.0001(19) F35 0.0664(17) 0.0767(18) 0.111(2) 0.0044(16) -0.0185(16) 0.0144(14) C36 0.054(2) 0.050(2) 0.047(2) -0.0001(17) -0.0040(17) -0.0033(18) F36 0.0676(15) 0.0700(15) 0.0593(14) -0.0057(12) 0.0019(11) 0.0157(12) C41 0.051(2) 0.052(2) 0.0382(18) -0.0093(16) -0.0018(15) -0.0009(17) C42 0.054(2) 0.069(3) 0.045(2) -0.0077(19) -0.0005(17) -0.011(2) F42 0.0658(15) 0.0742(16) 0.0591(14) 0.0176(12) -0.0066(12) -0.0188(13) C43 0.061(3) 0.091(3) 0.058(3) -0.015(2) 0.001(2) -0.018(3) F43 0.0770(19) 0.144(3) 0.089(2) 0.010(2) 0.0130(16) -0.048(2) C44 0.048(3) 0.101(4) 0.094(4) -0.029(3) -0.002(3) -0.016(3) F44 0.0455(16) 0.168(4) 0.156(3) -0.033(3) -0.0050(18) -0.0082(19) C45 0.058(3) 0.079(3) 0.087(3) -0.023(3) -0.025(3) 0.011(3) F45 0.077(2) 0.107(3) 0.157(3) -0.012(2) -0.049(2) 0.0213(18) C46 0.065(3) 0.051(2) 0.059(2) -0.009(2) -0.015(2) 0.004(2) F46 0.0816(18) 0.0704(17) 0.0875(19) 0.0179(15) -0.0319(15) 0.0012(14) C100 0.153(8) 0.185(9) 0.155(8) -0.004(7) 0.057(7) -0.034(7) Cl1 0.176(3) 0.217(4) 0.207(4) -0.073(3) 0.019(3) -0.037(3) Cl2 0.163(3) 0.311(6) 0.174(3) -0.083(4) 0.030(3) -0.022(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 P1 C1 1.790(4) . ? P1 C21 1.803(4) . ? P1 C11 1.811(4) . ? P1 C01 1.889(4) . ? B1 N1 1.580(5) . ? B1 C41 1.648(6) . ? B1 C31 1.655(5) . ? B1 C1 1.683(6) . ? O1 C01 1.212(5) . ? N1 C01 1.333(5) . ? N1 C4 1.446(5) . ? C1 C2 1.528(5) . ? C1 H1 0.9900 . ? C2 C3 1.528(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C5 1.378(5) . ? C4 C9 1.393(5) . ? C5 C6 1.376(6) . ? C5 H5 0.9400 . ? C6 C7 1.395(6) . ? C6 H6 0.9400 . ? C7 C8 1.370(6) . ? C7 C10 1.509(6) . ? C8 C9 1.389(6) . ? C8 H8 0.9400 . ? C9 H9 0.9400 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 C12 1.381(6) . ? C11 C16 1.388(6) . ? C12 F12 1.335(5) . ? C12 C13 1.364(6) . ? C13 F13 1.328(5) . ? C13 C14 1.343(8) . ? C14 F14 1.340(6) . ? C14 C15 1.347(8) . ? C15 F15 1.344(7) . ? C15 C16 1.370(7) . ? C16 F16 1.337(6) . ? C21 C22 1.389(6) . ? C21 C26 1.392(5) . ? C22 F22 1.340(5) . ? C22 C23 1.379(6) . ? C23 F23 1.332(5) . ? C23 C24 1.384(7) . ? C24 F24 1.336(5) . ? C24 C25 1.346(7) . ? C25 F25 1.344(5) . ? C25 C26 1.369(6) . ? C26 F26 1.333(5) . ? C31 C36 1.385(6) . ? C31 C32 1.398(5) . ? C32 F32 1.347(5) . ? C32 C33 1.377(6) . ? C33 F33 1.346(5) . ? C33 C34 1.365(7) . ? C34 F34 1.348(5) . ? C34 C35 1.369(7) . ? C35 F35 1.341(5) . ? C35 C36 1.386(6) . ? C36 F36 1.351(5) . ? C41 C46 1.386(6) . ? C41 C42 1.396(6) . ? C42 F42 1.349(5) . ? C42 C43 1.376(6) . ? C43 F43 1.344(6) . ? C43 C44 1.358(8) . ? C44 F44 1.337(6) . ? C44 C45 1.363(8) . ? C45 F45 1.348(6) . ? C45 C46 1.377(7) . ? C46 F46 1.354(5) . ? C100 Cl2 1.658(15) . ? C100 Cl1 1.695(14) . ? C100 H10D 0.9800 . ? C100 H10E 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 C1 P1 C21 115.56(18) . . ? C1 P1 C11 122.97(19) . . ? C21 P1 C11 105.98(19) . . ? C1 P1 C01 96.76(18) . . ? C21 P1 C01 108.55(17) . . ? C11 P1 C01 105.42(19) . . ? N1 B1 C41 106.0(3) . . ? N1 B1 C31 112.8(3) . . ? C41 B1 C31 114.8(3) . . ? N1 B1 C1 103.5(3) . . ? C41 B1 C1 112.9(3) . . ? C31 B1 C1 106.4(3) . . ? C01 N1 C4 117.6(3) . . ? C01 N1 B1 120.6(3) . . ? C4 N1 B1 121.7(3) . . ? O1 C01 N1 131.7(4) . . ? O1 C01 P1 121.9(3) . . ? N1 C01 P1 106.4(3) . . ? C2 C1 B1 120.6(3) . . ? C2 C1 P1 124.1(3) . . ? B1 C1 P1 102.5(2) . . ? C2 C1 H1 102.0 . . ? B1 C1 H1 102.0 . . ? P1 C1 H1 102.0 . . ? C1 C2 C3 114.6(3) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 119.2(4) . . ? C5 C4 N1 120.3(3) . . ? C9 C4 N1 120.4(3) . . ? C6 C5 C4 120.6(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.9(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 118.2(4) . . ? C8 C7 C10 121.1(4) . . ? C6 C7 C10 120.7(4) . . ? C7 C8 C9 121.7(4) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C4 119.4(4) . . ? C8 C9 H9 120.3 . . ? C4 C9 H9 120.3 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 115.1(4) . . ? C12 C11 P1 126.7(3) . . ? C16 C11 P1 118.1(3) . . ? F12 C12 C13 117.8(4) . . ? F12 C12 C11 119.3(4) . . ? C13 C12 C11 122.9(4) . . ? F13 C13 C14 119.4(4) . . ? F13 C13 C12 120.9(5) . . ? C14 C13 C12 119.7(5) . . ? F14 C14 C13 120.5(5) . . ? F14 C14 C15 119.3(5) . . ? C13 C14 C15 120.1(5) . . ? F15 C15 C14 120.6(5) . . ? F15 C15 C16 119.0(5) . . ? C14 C15 C16 120.4(5) . . ? F16 C16 C15 118.2(5) . . ? F16 C16 C11 120.0(4) . . ? C15 C16 C11 121.7(5) . . ? C22 C21 C26 116.3(4) . . ? C22 C21 P1 123.6(3) . . ? C26 C21 P1 120.0(3) . . ? F22 C22 C23 118.3(4) . . ? F22 C22 C21 119.6(4) . . ? C23 C22 C21 122.1(4) . . ? F23 C23 C22 119.8(5) . . ? F23 C23 C24 121.6(4) . . ? C22 C23 C24 118.7(4) . . ? F24 C24 C25 120.7(5) . . ? F24 C24 C23 118.5(5) . . ? C25 C24 C23 120.8(4) . . ? F25 C25 C24 119.7(4) . . ? F25 C25 C26 120.4(4) . . ? C24 C25 C26 120.0(4) . . ? F26 C26 C25 118.0(4) . . ? F26 C26 C21 119.9(4) . . ? C25 C26 C21 122.1(4) . . ? C36 C31 C32 112.9(3) . . ? C36 C31 B1 125.9(3) . . ? C32 C31 B1 120.8(3) . . ? F32 C32 C33 116.1(4) . . ? F32 C32 C31 119.5(3) . . ? C33 C32 C31 124.4(4) . . ? F33 C33 C34 120.5(4) . . ? F33 C33 C32 120.0(5) . . ? C34 C33 C32 119.5(4) . . ? F34 C34 C33 120.5(5) . . ? F34 C34 C35 120.1(5) . . ? C33 C34 C35 119.4(4) . . ? F35 C35 C34 120.7(4) . . ? F35 C35 C36 119.9(4) . . ? C34 C35 C36 119.4(4) . . ? F36 C36 C35 114.9(4) . . ? F36 C36 C31 120.8(3) . . ? C35 C36 C31 124.3(4) . . ? C46 C41 C42 112.1(4) . . ? C46 C41 B1 121.7(4) . . ? C42 C41 B1 125.8(3) . . ? F42 C42 C43 114.6(4) . . ? F42 C42 C41 120.7(4) . . ? C43 C42 C41 124.7(4) . . ? F43 C43 C44 120.1(5) . . ? F43 C43 C42 120.2(5) . . ? C44 C43 C42 119.7(5) . . ? F44 C44 C43 120.3(6) . . ? F44 C44 C45 120.7(6) . . ? C43 C44 C45 119.0(4) . . ? F45 C45 C44 120.6(5) . . ? F45 C45 C46 119.6(5) . . ? C44 C45 C46 119.8(5) . . ? F46 C46 C45 115.9(4) . . ? F46 C46 C41 119.4(4) . . ? C45 C46 C41 124.7(5) . . ? Cl2 C100 Cl1 115.1(9) . . ? Cl2 C100 H10D 108.5 . . ? Cl1 C100 H10D 108.5 . . ? Cl2 C100 H10E 108.5 . . ? Cl1 C100 H10E 108.5 . . ? H10D C100 H10E 107.5 . . ? 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 C41 B1 N1 C01 142.0(3) . . . . ? C31 B1 N1 C01 -91.6(4) . . . . ? C1 B1 N1 C01 22.9(4) . . . . ? C41 B1 N1 C4 -38.2(4) . . . . ? C31 B1 N1 C4 88.2(4) . . . . ? C1 B1 N1 C4 -157.3(3) . . . . ? C4 N1 C01 O1 -4.4(7) . . . . ? B1 N1 C01 O1 175.4(4) . . . . ? C4 N1 C01 P1 177.4(3) . . . . ? B1 N1 C01 P1 -2.8(4) . . . . ? C1 P1 C01 O1 164.7(4) . . . . ? C21 P1 C01 O1 44.8(4) . . . . ? C11 P1 C01 O1 -68.3(4) . . . . ? C1 P1 C01 N1 -16.8(3) . . . . ? C21 P1 C01 N1 -136.7(3) . . . . ? C11 P1 C01 N1 110.1(3) . . . . ? N1 B1 C1 C2 -174.0(3) . . . . ? C41 B1 C1 C2 71.8(4) . . . . ? C31 B1 C1 C2 -55.0(5) . . . . ? N1 B1 C1 P1 -31.1(3) . . . . ? C41 B1 C1 P1 -145.3(3) . . . . ? C31 B1 C1 P1 87.9(3) . . . . ? C21 P1 C1 C2 -76.6(4) . . . . ? C11 P1 C1 C2 55.8(4) . . . . ? C01 P1 C1 C2 169.1(3) . . . . ? C21 P1 C1 B1 142.3(2) . . . . ? C11 P1 C1 B1 -85.4(3) . . . . ? C01 P1 C1 B1 27.9(3) . . . . ? B1 C1 C2 C3 -179.0(4) . . . . ? P1 C1 C2 C3 46.3(5) . . . . ? C01 N1 C4 C5 137.5(4) . . . . ? B1 N1 C4 C5 -42.3(5) . . . . ? C01 N1 C4 C9 -47.0(5) . . . . ? B1 N1 C4 C9 133.2(4) . . . . ? C9 C4 C5 C6 1.1(6) . . . . ? N1 C4 C5 C6 176.7(4) . . . . ? C4 C5 C6 C7 0.3(6) . . . . ? C5 C6 C7 C8 -1.0(6) . . . . ? C5 C6 C7 C10 178.0(4) . . . . ? C6 C7 C8 C9 0.3(6) . . . . ? C10 C7 C8 C9 -178.7(4) . . . . ? C7 C8 C9 C4 1.0(6) . . . . ? C5 C4 C9 C8 -1.7(6) . . . . ? N1 C4 C9 C8 -177.3(4) . . . . ? C1 P1 C11 C12 -13.7(5) . . . . ? C21 P1 C11 C12 122.4(4) . . . . ? C01 P1 C11 C12 -122.6(4) . . . . ? C1 P1 C11 C16 164.1(4) . . . . ? C21 P1 C11 C16 -59.8(5) . . . . ? C01 P1 C11 C16 55.2(5) . . . . ? C16 C11 C12 F12 178.7(5) . . . . ? P1 C11 C12 F12 -3.4(6) . . . . ? C16 C11 C12 C13 -1.4(7) . . . . ? P1 C11 C12 C13 176.4(4) . . . . ? F12 C12 C13 F13 1.2(7) . . . . ? C11 C12 C13 F13 -178.6(4) . . . . ? F12 C12 C13 C14 -179.5(5) . . . . ? C11 C12 C13 C14 0.6(8) . . . . ? F13 C13 C14 F14 -3.0(9) . . . . ? C12 C13 C14 F14 177.7(5) . . . . ? F13 C13 C14 C15 179.8(6) . . . . ? C12 C13 C14 C15 0.5(10) . . . . ? F14 C14 C15 F15 1.8(12) . . . . ? C13 C14 C15 F15 179.1(7) . . . . ? F14 C14 C15 C16 -178.0(7) . . . . ? C13 C14 C15 C16 -0.7(12) . . . . ? F15 C15 C16 F16 -3.9(12) . . . . ? C14 C15 C16 F16 175.8(7) . . . . ? F15 C15 C16 C11 -180.0(7) . . . . ? C14 C15 C16 C11 -0.2(12) . . . . ? C12 C11 C16 F16 -174.8(5) . . . . ? P1 C11 C16 F16 7.2(8) . . . . ? C12 C11 C16 C15 1.2(9) . . . . ? P1 C11 C16 C15 -176.8(6) . . . . ? C1 P1 C21 C22 105.4(4) . . . . ? C11 P1 C21 C22 -34.5(4) . . . . ? C01 P1 C21 C22 -147.3(3) . . . . ? C1 P1 C21 C26 -77.5(4) . . . . ? C11 P1 C21 C26 142.6(3) . . . . ? C01 P1 C21 C26 29.8(4) . . . . ? C26 C21 C22 F22 178.8(4) . . . . ? P1 C21 C22 F22 -4.0(6) . . . . ? C26 C21 C22 C23 -1.6(6) . . . . ? P1 C21 C22 C23 175.6(3) . . . . ? F22 C22 C23 F23 0.0(6) . . . . ? C21 C22 C23 F23 -179.6(4) . . . . ? F22 C22 C23 C24 179.6(4) . . . . ? C21 C22 C23 C24 0.0(7) . . . . ? F23 C23 C24 F24 1.7(7) . . . . ? C22 C23 C24 F24 -177.9(4) . . . . ? F23 C23 C24 C25 -179.7(4) . . . . ? C22 C23 C24 C25 0.7(7) . . . . ? F24 C24 C25 F25 -1.1(6) . . . . ? C23 C24 C25 F25 -179.8(4) . . . . ? F24 C24 C25 C26 178.9(4) . . . . ? C23 C24 C25 C26 0.3(7) . . . . ? F25 C25 C26 F26 -3.1(6) . . . . ? C24 C25 C26 F26 176.8(4) . . . . ? F25 C25 C26 C21 178.0(4) . . . . ? C24 C25 C26 C21 -2.1(6) . . . . ? C22 C21 C26 F26 -176.2(4) . . . . ? P1 C21 C26 F26 6.5(5) . . . . ? C22 C21 C26 C25 2.6(6) . . . . ? P1 C21 C26 C25 -174.7(3) . . . . ? N1 B1 C31 C36 14.8(5) . . . . ? C41 B1 C31 C36 136.4(4) . . . . ? C1 B1 C31 C36 -97.9(4) . . . . ? N1 B1 C31 C32 -172.5(3) . . . . ? C41 B1 C31 C32 -50.9(5) . . . . ? C1 B1 C31 C32 74.8(4) . . . . ? C36 C31 C32 F32 -179.9(3) . . . . ? B1 C31 C32 F32 6.5(5) . . . . ? C36 C31 C32 C33 -0.2(6) . . . . ? B1 C31 C32 C33 -173.8(4) . . . . ? F32 C32 C33 F33 1.5(5) . . . . ? C31 C32 C33 F33 -178.3(4) . . . . ? F32 C32 C33 C34 -178.8(4) . . . . ? C31 C32 C33 C34 1.4(6) . . . . ? F33 C33 C34 F34 -1.5(6) . . . . ? C32 C33 C34 F34 178.8(4) . . . . ? F33 C33 C34 C35 178.7(4) . . . . ? C32 C33 C34 C35 -1.0(6) . . . . ? F34 C34 C35 F35 0.0(6) . . . . ? C33 C34 C35 F35 179.8(4) . . . . ? F34 C34 C35 C36 179.6(4) . . . . ? C33 C34 C35 C36 -0.6(6) . . . . ? F35 C35 C36 F36 1.1(6) . . . . ? C34 C35 C36 F36 -178.6(4) . . . . ? F35 C35 C36 C31 -178.4(4) . . . . ? C34 C35 C36 C31 2.0(6) . . . . ? C32 C31 C36 F36 179.0(3) . . . . ? B1 C31 C36 F36 -7.8(6) . . . . ? C32 C31 C36 C35 -1.6(6) . . . . ? B1 C31 C36 C35 171.7(4) . . . . ? N1 B1 C41 C46 -64.0(4) . . . . ? C31 B1 C41 C46 170.9(3) . . . . ? C1 B1 C41 C46 48.6(5) . . . . ? N1 B1 C41 C42 108.4(4) . . . . ? C31 B1 C41 C42 -16.8(5) . . . . ? C1 B1 C41 C42 -139.0(4) . . . . ? C46 C41 C42 F42 175.0(3) . . . . ? B1 C41 C42 F42 2.0(6) . . . . ? C46 C41 C42 C43 -2.5(6) . . . . ? B1 C41 C42 C43 -175.6(4) . . . . ? F42 C42 C43 F43 2.6(6) . . . . ? C41 C42 C43 F43 -179.8(4) . . . . ? F42 C42 C43 C44 -175.8(4) . . . . ? C41 C42 C43 C44 1.9(7) . . . . ? F43 C43 C44 F44 0.9(8) . . . . ? C42 C43 C44 F44 179.2(4) . . . . ? F43 C43 C44 C45 -178.7(5) . . . . ? C42 C43 C44 C45 -0.4(8) . . . . ? F44 C44 C45 F45 -0.8(8) . . . . ? C43 C44 C45 F45 178.8(5) . . . . ? F44 C44 C45 C46 -179.8(4) . . . . ? C43 C44 C45 C46 -0.2(8) . . . . ? F45 C45 C46 F46 -1.6(6) . . . . ? C44 C45 C46 F46 177.4(4) . . . . ? F45 C45 C46 C41 -179.7(4) . . . . ? C44 C45 C46 C41 -0.6(7) . . . . ? C42 C41 C46 F46 -176.1(3) . . . . ? B1 C41 C46 F46 -2.7(6) . . . . ? C42 C41 C46 C45 1.9(6) . . . . ? B1 C41 C46 C45 175.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 67.30 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.825 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.071 # Attachment '- 10.cif' data_erk5582 _database_code_depnum_ccdc_archive 'CCDC 809021' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H17 B F20 N3 P' _chemical_formula_weight 913.31 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 9.7940(3) _cell_length_b 13.5562(5) _cell_length_c 26.7495(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.441(2) _cell_angle_gamma 90.00 _cell_volume 3521.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6127 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 2.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6557 _exptl_absorpt_correction_T_max 0.7949 _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 29109 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 67.52 _reflns_number_total 6200 _reflns_number_gt 5057 _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 (BruerkAXS, 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^)+(0.0661P)^2^+2.6266P] 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 6200 _refine_ls_number_parameters 554 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.10453(6) 0.53032(5) 0.10849(2) 0.03506(16) Uani 1 1 d . . . B1 B 0.0460(3) 0.7173(2) 0.14425(10) 0.0349(6) Uani 1 1 d . . . C1 C 0.1765(2) 0.64452(18) 0.13308(9) 0.0374(5) Uani 1 1 d . . . H1 H 0.2090 0.6757 0.1033 0.045 Uiso 1 1 calc R . . C2 C 0.3057(3) 0.6464(2) 0.17279(10) 0.0425(6) Uani 1 1 d . . . H2A H 0.3453 0.7128 0.1735 0.051 Uiso 1 1 calc R . . H2B H 0.2771 0.6340 0.2060 0.051 Uiso 1 1 calc R . . C3 C 0.4176(3) 0.5726(2) 0.16443(12) 0.0552(8) Uani 1 1 d . . . H3A H 0.3846 0.5062 0.1690 0.083 Uiso 1 1 calc R . . H3B H 0.4987 0.5848 0.1885 0.083 Uiso 1 1 calc R . . H3C H 0.4409 0.5797 0.1305 0.083 Uiso 1 1 calc R . . N1 N -0.0339(2) 0.55564(15) 0.06745(8) 0.0371(5) Uani 1 1 d . . . N2 N -0.0964(2) 0.64080(15) 0.06373(8) 0.0368(5) Uani 1 1 d . . . N3 N -0.0707(2) 0.71326(15) 0.09577(7) 0.0337(4) Uani 1 1 d . . . C11 C 0.0525(3) 0.43549(19) 0.15047(9) 0.0379(5) Uani 1 1 d . . . C12 C 0.0877(3) 0.43248(19) 0.20252(10) 0.0418(6) Uani 1 1 d . . . F12 F 0.18011(17) 0.49539(12) 0.22604(6) 0.0550(4) Uani 1 1 d . . . C13 C 0.0287(3) 0.3669(2) 0.23263(10) 0.0441(6) Uani 1 1 d . . . F13 F 0.0610(2) 0.37132(13) 0.28272(6) 0.0620(5) Uani 1 1 d . . . C14 C -0.0661(3) 0.3003(2) 0.21139(11) 0.0476(7) Uani 1 1 d . . . F14 F -0.1263(2) 0.23835(13) 0.24061(7) 0.0659(5) Uani 1 1 d . . . C15 C -0.1003(3) 0.2978(2) 0.15995(11) 0.0491(7) Uani 1 1 d . . . F15 F -0.1898(2) 0.23143(14) 0.13874(7) 0.0751(6) Uani 1 1 d . . . C16 C -0.0403(3) 0.3637(2) 0.13060(9) 0.0430(6) Uani 1 1 d . . . F16 F -0.0723(2) 0.35610(12) 0.08046(6) 0.0594(5) Uani 1 1 d . . . C21 C 0.2155(3) 0.46964(19) 0.06851(10) 0.0400(6) Uani 1 1 d . . . C22 C 0.2722(3) 0.3761(2) 0.07646(11) 0.0484(7) Uani 1 1 d . . . F22 F 0.2515(2) 0.32393(13) 0.11727(7) 0.0703(5) Uani 1 1 d . . . C23 C 0.3524(3) 0.3338(2) 0.04411(12) 0.0536(7) Uani 1 1 d . . . F23 F 0.4046(2) 0.24348(15) 0.05312(8) 0.0811(6) Uani 1 1 d . . . C24 C 0.3795(3) 0.3845(2) 0.00202(11) 0.0525(7) Uani 1 1 d . . . F24 F 0.45802(19) 0.34406(16) -0.02963(7) 0.0735(6) Uani 1 1 d . . . C25 C 0.3257(3) 0.4773(2) -0.00732(10) 0.0468(7) Uani 1 1 d . . . F25 F 0.34992(18) 0.52594(15) -0.04881(6) 0.0623(5) Uani 1 1 d . . . C26 C 0.2457(3) 0.5185(2) 0.02551(10) 0.0409(6) Uani 1 1 d . . . F26 F 0.19777(17) 0.60998(12) 0.01566(6) 0.0500(4) Uani 1 1 d . . . C31 C -0.0145(3) 0.67679(19) 0.19558(9) 0.0388(6) Uani 1 1 d . . . C32 C 0.0399(3) 0.7066(2) 0.24395(10) 0.0441(6) Uani 1 1 d . . . F32 F 0.14226(16) 0.77408(13) 0.25047(6) 0.0554(4) Uani 1 1 d . . . C33 C -0.0065(3) 0.6732(2) 0.28756(10) 0.0523(7) Uani 1 1 d . . . F33 F 0.0476(2) 0.70878(17) 0.33274(6) 0.0736(6) Uani 1 1 d . . . C34 C -0.1059(3) 0.6016(2) 0.28530(11) 0.0507(7) Uani 1 1 d . . . F34 F -0.14770(19) 0.56572(16) 0.32731(7) 0.0701(5) Uani 1 1 d . . . C35 C -0.1624(3) 0.5679(2) 0.23899(11) 0.0445(6) Uani 1 1 d . . . F35 F -0.25887(17) 0.49684(13) 0.23494(7) 0.0586(4) Uani 1 1 d . . . C36 C -0.1175(3) 0.60643(19) 0.19604(10) 0.0394(6) Uani 1 1 d . . . F36 F -0.17979(15) 0.56733(11) 0.15214(6) 0.0450(4) Uani 1 1 d . . . C41 C 0.0918(3) 0.83484(19) 0.14844(9) 0.0370(5) Uani 1 1 d . . . C42 C 0.0191(3) 0.90395(19) 0.17284(10) 0.0408(6) Uani 1 1 d . . . F42 F -0.08690(16) 0.87566(12) 0.19701(6) 0.0522(4) Uani 1 1 d . . . C43 C 0.0454(3) 1.0034(2) 0.17480(12) 0.0491(7) Uani 1 1 d . . . F43 F -0.0292(2) 1.06490(13) 0.19964(8) 0.0710(5) Uani 1 1 d . . . C44 C 0.1510(3) 1.0404(2) 0.15145(14) 0.0575(8) Uani 1 1 d . . . F44 F 0.1769(2) 1.13750(14) 0.15296(11) 0.0942(8) Uani 1 1 d . . . C45 C 0.2278(3) 0.9767(2) 0.12675(12) 0.0506(7) Uani 1 1 d . . . F45 F 0.33321(19) 1.01084(13) 0.10387(9) 0.0734(6) Uani 1 1 d . . . C46 C 0.1976(3) 0.87748(19) 0.12557(10) 0.0404(6) Uani 1 1 d . . . F46 F 0.28044(16) 0.82188(12) 0.09981(6) 0.0509(4) Uani 1 1 d . . . C51 C -0.1486(2) 0.80073(18) 0.07657(9) 0.0358(5) Uani 1 1 d . . . C52 C -0.2650(3) 0.8308(2) 0.09723(9) 0.0397(6) Uani 1 1 d . . . C53 C -0.3280(3) 0.9189(2) 0.08027(10) 0.0450(6) Uani 1 1 d . . . H53 H -0.4054 0.9406 0.0946 0.054 Uiso 1 1 calc R . . C54 C -0.2804(3) 0.9758(2) 0.04288(11) 0.0465(6) Uani 1 1 d . . . C55 C -0.1721(3) 0.9387(2) 0.02033(11) 0.0456(6) Uani 1 1 d . . . H55 H -0.1428 0.9737 -0.0067 0.055 Uiso 1 1 calc R . . C56 C -0.1046(3) 0.85157(19) 0.03596(9) 0.0387(6) Uani 1 1 d . . . C57 C -0.3302(3) 0.7710(2) 0.13538(11) 0.0507(7) Uani 1 1 d . . . H57A H -0.3402 0.7031 0.1241 0.076 Uiso 1 1 calc R . . H57B H -0.4200 0.7980 0.1390 0.076 Uiso 1 1 calc R . . H57C H -0.2721 0.7734 0.1676 0.076 Uiso 1 1 calc R . . C58 C -0.3480(3) 1.0735(2) 0.02740(14) 0.0639(9) Uani 1 1 d . . . H58A H -0.4381 1.0763 0.0387 0.096 Uiso 1 1 calc R . . H58B H -0.3578 1.0797 -0.0090 0.096 Uiso 1 1 calc R . . H58C H -0.2914 1.1270 0.0426 0.096 Uiso 1 1 calc R . . C59 C 0.0081(3) 0.8129(2) 0.00799(11) 0.0486(7) Uani 1 1 d . . . H59A H 0.0276 0.8607 -0.0171 0.073 Uiso 1 1 calc R . . H59B H -0.0212 0.7513 -0.0085 0.073 Uiso 1 1 calc R . . H59C H 0.0905 0.8016 0.0316 0.073 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 P1 0.0371(3) 0.0308(3) 0.0366(3) 0.0017(3) 0.0023(2) -0.0001(2) B1 0.0343(14) 0.0337(15) 0.0360(14) 0.0007(11) 0.0023(11) -0.0032(11) C1 0.0369(13) 0.0341(13) 0.0403(13) 0.0024(10) 0.0020(10) -0.0008(10) C2 0.0365(13) 0.0395(15) 0.0495(15) -0.0006(12) -0.0023(11) -0.0038(11) C3 0.0372(14) 0.0594(19) 0.0662(19) -0.0037(15) -0.0044(13) 0.0046(13) N1 0.0384(11) 0.0313(11) 0.0401(11) 0.0005(9) 0.0002(9) -0.0018(9) N2 0.0368(11) 0.0317(11) 0.0413(11) 0.0003(9) 0.0032(9) -0.0011(9) N3 0.0343(10) 0.0297(10) 0.0366(11) 0.0002(8) 0.0028(8) -0.0011(8) C11 0.0398(13) 0.0329(13) 0.0403(13) 0.0013(10) 0.0031(10) 0.0007(10) C12 0.0442(14) 0.0350(14) 0.0441(14) 0.0010(11) -0.0016(11) 0.0002(11) F12 0.0605(10) 0.0520(10) 0.0476(9) 0.0071(7) -0.0117(7) -0.0128(8) C13 0.0584(17) 0.0367(14) 0.0373(14) 0.0070(11) 0.0063(12) 0.0046(12) F13 0.0933(13) 0.0531(10) 0.0378(9) 0.0092(7) 0.0021(8) -0.0024(9) C14 0.0614(17) 0.0338(14) 0.0496(16) 0.0068(12) 0.0147(13) -0.0002(13) F14 0.0913(13) 0.0477(10) 0.0629(11) 0.0097(8) 0.0256(9) -0.0172(9) C15 0.0595(17) 0.0342(14) 0.0531(17) 0.0002(12) 0.0060(13) -0.0109(13) F15 0.0964(15) 0.0540(11) 0.0714(12) 0.0012(9) -0.0022(10) -0.0379(10) C16 0.0551(16) 0.0358(14) 0.0371(14) -0.0006(11) 0.0023(11) -0.0014(12) F16 0.0895(13) 0.0445(9) 0.0412(9) -0.0015(7) -0.0027(8) -0.0167(9) C21 0.0403(13) 0.0361(14) 0.0426(14) -0.0002(11) 0.0013(11) -0.0006(11) C22 0.0520(16) 0.0418(16) 0.0512(16) 0.0027(13) 0.0058(13) 0.0045(13) F22 0.0863(13) 0.0503(11) 0.0788(12) 0.0209(9) 0.0274(10) 0.0289(10) C23 0.0466(16) 0.0455(17) 0.0677(19) -0.0105(14) 0.0034(14) 0.0092(13) F23 0.0884(14) 0.0570(12) 0.0997(15) -0.0070(11) 0.0189(12) 0.0309(11) C24 0.0405(15) 0.0601(19) 0.0568(17) -0.0211(15) 0.0059(12) -0.0015(13) F24 0.0617(11) 0.0869(14) 0.0756(12) -0.0320(11) 0.0221(9) 0.0034(10) C25 0.0374(14) 0.0600(19) 0.0426(15) -0.0057(13) 0.0040(11) -0.0095(13) F25 0.0554(10) 0.0857(13) 0.0483(9) -0.0024(9) 0.0158(7) -0.0112(9) C26 0.0352(13) 0.0420(15) 0.0441(14) -0.0018(12) 0.0005(10) -0.0013(11) F26 0.0583(10) 0.0449(9) 0.0478(9) 0.0078(7) 0.0101(7) 0.0016(7) C31 0.0372(13) 0.0368(14) 0.0421(14) 0.0038(11) 0.0033(10) 0.0027(11) C32 0.0420(14) 0.0469(16) 0.0426(14) 0.0021(12) 0.0023(11) -0.0016(12) F32 0.0527(9) 0.0650(11) 0.0463(9) -0.0038(8) -0.0025(7) -0.0128(8) C33 0.0539(17) 0.068(2) 0.0342(14) 0.0013(13) 0.0016(12) 0.0079(15) F33 0.0733(12) 0.1079(17) 0.0377(9) -0.0011(9) -0.0003(8) -0.0060(11) C34 0.0508(16) 0.0584(19) 0.0448(16) 0.0179(14) 0.0138(12) 0.0100(14) F34 0.0722(12) 0.0906(14) 0.0510(10) 0.0265(10) 0.0218(9) 0.0070(10) C35 0.0411(14) 0.0404(15) 0.0540(16) 0.0109(12) 0.0145(12) 0.0040(12) F35 0.0548(10) 0.0524(10) 0.0721(11) 0.0143(8) 0.0216(8) -0.0080(8) C36 0.0406(13) 0.0360(14) 0.0418(14) 0.0021(11) 0.0064(11) 0.0021(11) F36 0.0464(8) 0.0406(8) 0.0484(8) -0.0005(7) 0.0074(6) -0.0075(7) C41 0.0382(13) 0.0340(13) 0.0375(13) 0.0008(10) 0.0006(10) -0.0026(10) C42 0.0380(13) 0.0381(14) 0.0467(14) -0.0025(11) 0.0064(11) -0.0036(11) F42 0.0516(9) 0.0454(9) 0.0629(10) -0.0046(7) 0.0203(8) -0.0012(7) C43 0.0494(16) 0.0336(14) 0.0643(18) -0.0072(13) 0.0071(13) 0.0017(12) F43 0.0760(12) 0.0408(10) 0.1007(15) -0.0168(9) 0.0282(11) 0.0020(9) C44 0.0565(18) 0.0270(14) 0.089(2) 0.0007(14) 0.0087(16) -0.0064(13) F44 0.0921(15) 0.0331(10) 0.164(2) -0.0078(12) 0.0432(15) -0.0149(10) C45 0.0450(15) 0.0394(16) 0.0685(19) 0.0055(14) 0.0116(13) -0.0070(12) F45 0.0640(11) 0.0469(10) 0.1157(16) 0.0112(10) 0.0359(11) -0.0128(9) C46 0.0396(14) 0.0346(14) 0.0465(14) 0.0014(11) 0.0045(11) 0.0003(11) F46 0.0494(9) 0.0426(9) 0.0644(10) 0.0022(7) 0.0220(7) -0.0018(7) C51 0.0346(12) 0.0326(13) 0.0389(13) 0.0016(10) 0.0003(10) 0.0005(10) C52 0.0368(13) 0.0407(15) 0.0410(13) -0.0016(11) 0.0030(10) 0.0022(11) C53 0.0385(14) 0.0488(16) 0.0473(15) -0.0034(12) 0.0041(11) 0.0076(12) C54 0.0441(15) 0.0373(15) 0.0568(17) 0.0015(12) 0.0009(12) 0.0051(12) C55 0.0487(15) 0.0385(15) 0.0493(15) 0.0077(12) 0.0059(12) 0.0032(12) C56 0.0389(13) 0.0363(14) 0.0403(13) 0.0030(11) 0.0030(10) -0.0003(11) C57 0.0412(14) 0.0585(18) 0.0538(16) 0.0055(14) 0.0117(12) 0.0032(13) C58 0.0610(19) 0.0458(18) 0.084(2) 0.0096(16) 0.0065(16) 0.0140(15) C59 0.0519(16) 0.0434(16) 0.0532(16) 0.0099(13) 0.0174(13) 0.0063(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.666(2) . ? P1 C1 1.790(3) . ? P1 C21 1.817(3) . ? P1 C11 1.822(3) . ? B1 N3 1.615(3) . ? B1 C41 1.655(4) . ? B1 C31 1.657(4) . ? B1 C1 1.672(4) . ? C1 C2 1.543(3) . ? C1 H1 0.9900 . ? C2 C3 1.522(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? N1 N2 1.304(3) . ? N2 N3 1.306(3) . ? N3 C51 1.466(3) . ? C11 C16 1.390(4) . ? C11 C12 1.391(4) . ? C12 F12 1.340(3) . ? C12 C13 1.376(4) . ? C13 F13 1.337(3) . ? C13 C14 1.365(4) . ? C14 F14 1.335(3) . ? C14 C15 1.374(4) . ? C15 F15 1.330(3) . ? C15 C16 1.371(4) . ? C16 F16 1.341(3) . ? C21 C22 1.390(4) . ? C21 C26 1.392(4) . ? C22 F22 1.338(3) . ? C22 C23 1.368(4) . ? C23 F23 1.336(3) . ? C23 C24 1.374(5) . ? C24 F24 1.333(3) . ? C24 C25 1.375(4) . ? C25 F25 1.338(3) . ? C25 C26 1.369(4) . ? C26 F26 1.340(3) . ? C31 C36 1.389(4) . ? C31 C32 1.394(4) . ? C32 F32 1.352(3) . ? C32 C33 1.382(4) . ? C33 F33 1.345(3) . ? C33 C34 1.371(4) . ? C34 F34 1.336(3) . ? C34 C35 1.368(4) . ? C35 F35 1.344(3) . ? C35 C36 1.384(4) . ? C36 F36 1.359(3) . ? C41 C42 1.389(4) . ? C41 C46 1.395(4) . ? C42 F42 1.348(3) . ? C42 C43 1.373(4) . ? C43 F43 1.340(3) . ? C43 C44 1.370(4) . ? C44 F44 1.340(3) . ? C44 C45 1.370(4) . ? C45 F45 1.348(3) . ? C45 C46 1.377(4) . ? C46 F46 1.359(3) . ? C51 C52 1.391(3) . ? C51 C56 1.401(3) . ? C52 C53 1.392(4) . ? C52 C57 1.508(4) . ? C53 C54 1.391(4) . ? C53 H53 0.9400 . ? C54 C55 1.381(4) . ? C54 C58 1.514(4) . ? C55 C56 1.391(4) . ? C55 H55 0.9400 . ? C56 C59 1.506(4) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C57 H57C 0.9700 . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C58 H58C 0.9700 . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C59 H59C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C1 108.17(11) . . ? N1 P1 C21 101.71(11) . . ? C1 P1 C21 111.76(12) . . ? N1 P1 C11 106.43(11) . . ? C1 P1 C11 120.78(12) . . ? C21 P1 C11 106.24(12) . . ? N3 B1 C41 104.14(19) . . ? N3 B1 C31 111.26(19) . . ? C41 B1 C31 112.7(2) . . ? N3 B1 C1 108.33(19) . . ? C41 B1 C1 111.9(2) . . ? C31 B1 C1 108.4(2) . . ? C2 C1 B1 116.4(2) . . ? C2 C1 P1 121.04(18) . . ? B1 C1 P1 107.59(16) . . ? C2 C1 H1 103.0 . . ? B1 C1 H1 103.0 . . ? P1 C1 H1 103.0 . . ? C3 C2 C1 115.5(2) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 N1 P1 124.49(17) . . ? N1 N2 N3 124.5(2) . . ? N2 N3 C51 109.34(18) . . ? N2 N3 B1 127.46(19) . . ? C51 N3 B1 122.42(19) . . ? C16 C11 C12 115.3(2) . . ? C16 C11 P1 118.67(19) . . ? C12 C11 P1 125.8(2) . . ? F12 C12 C13 116.5(2) . . ? F12 C12 C11 121.1(2) . . ? C13 C12 C11 122.5(2) . . ? F13 C13 C14 120.5(2) . . ? F13 C13 C12 119.6(2) . . ? C14 C13 C12 119.9(2) . . ? F14 C14 C13 120.0(2) . . ? F14 C14 C15 120.1(3) . . ? C13 C14 C15 119.9(2) . . ? F15 C15 C16 120.2(3) . . ? F15 C15 C14 120.4(3) . . ? C16 C15 C14 119.4(3) . . ? F16 C16 C15 117.5(2) . . ? F16 C16 C11 119.5(2) . . ? C15 C16 C11 123.0(2) . . ? C22 C21 C26 115.9(2) . . ? C22 C21 P1 125.5(2) . . ? C26 C21 P1 118.6(2) . . ? F22 C22 C23 117.1(3) . . ? F22 C22 C21 120.5(2) . . ? C23 C22 C21 122.5(3) . . ? F23 C23 C22 120.5(3) . . ? F23 C23 C24 119.7(3) . . ? C22 C23 C24 119.8(3) . . ? F24 C24 C23 120.2(3) . . ? F24 C24 C25 120.0(3) . . ? C23 C24 C25 119.8(3) . . ? F25 C25 C26 120.6(3) . . ? F25 C25 C24 119.8(3) . . ? C26 C25 C24 119.6(3) . . ? F26 C26 C25 117.8(2) . . ? F26 C26 C21 119.7(2) . . ? C25 C26 C21 122.5(3) . . ? C36 C31 C32 112.4(2) . . ? C36 C31 B1 124.9(2) . . ? C32 C31 B1 122.6(2) . . ? F32 C32 C33 115.6(2) . . ? F32 C32 C31 120.3(2) . . ? C33 C32 C31 124.1(3) . . ? F33 C33 C34 119.3(3) . . ? F33 C33 C32 120.5(3) . . ? C34 C33 C32 120.3(3) . . ? F34 C34 C35 120.6(3) . . ? F34 C34 C33 120.9(3) . . ? C35 C34 C33 118.5(2) . . ? F35 C35 C34 120.6(2) . . ? F35 C35 C36 119.9(3) . . ? C34 C35 C36 119.4(3) . . ? F36 C36 C35 114.5(2) . . ? F36 C36 C31 120.4(2) . . ? C35 C36 C31 125.1(3) . . ? C42 C41 C46 112.4(2) . . ? C42 C41 B1 122.0(2) . . ? C46 C41 B1 125.4(2) . . ? F42 C42 C43 114.4(2) . . ? F42 C42 C41 120.4(2) . . ? C43 C42 C41 125.2(2) . . ? F43 C43 C44 119.4(3) . . ? F43 C43 C42 121.2(3) . . ? C44 C43 C42 119.4(3) . . ? F44 C44 C45 121.3(3) . . ? F44 C44 C43 119.8(3) . . ? C45 C44 C43 118.9(3) . . ? F45 C45 C44 120.2(3) . . ? F45 C45 C46 120.0(3) . . ? C44 C45 C46 119.8(3) . . ? F46 C46 C45 114.4(2) . . ? F46 C46 C41 121.3(2) . . ? C45 C46 C41 124.3(3) . . ? C52 C51 C56 120.9(2) . . ? C52 C51 N3 120.9(2) . . ? C56 C51 N3 118.1(2) . . ? C51 C52 C53 118.3(2) . . ? C51 C52 C57 123.4(2) . . ? C53 C52 C57 118.2(2) . . ? C54 C53 C52 122.3(2) . . ? C54 C53 H53 118.8 . . ? C52 C53 H53 118.8 . . ? C55 C54 C53 117.4(2) . . ? C55 C54 C58 122.2(3) . . ? C53 C54 C58 120.4(3) . . ? C54 C55 C56 122.7(3) . . ? C54 C55 H55 118.7 . . ? C56 C55 H55 118.7 . . ? C55 C56 C51 118.0(2) . . ? C55 C56 C59 119.8(2) . . ? C51 C56 C59 122.2(2) . . ? C52 C57 H57A 109.5 . . ? C52 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C52 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C54 C58 H58A 109.5 . . ? C54 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C54 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C56 C59 H59A 109.5 . . ? C56 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C56 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? 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 N3 B1 C1 C2 173.9(2) . . . . ? C41 B1 C1 C2 59.7(3) . . . . ? C31 B1 C1 C2 -65.2(3) . . . . ? N3 B1 C1 P1 -46.5(2) . . . . ? C41 B1 C1 P1 -160.72(17) . . . . ? C31 B1 C1 P1 74.4(2) . . . . ? N1 P1 C1 C2 179.30(19) . . . . ? C21 P1 C1 C2 -69.5(2) . . . . ? C11 P1 C1 C2 56.5(2) . . . . ? N1 P1 C1 B1 41.93(19) . . . . ? C21 P1 C1 B1 153.10(16) . . . . ? C11 P1 C1 B1 -80.88(19) . . . . ? B1 C1 C2 C3 174.4(2) . . . . ? P1 C1 C2 C3 40.6(3) . . . . ? C1 P1 N1 N2 -15.3(2) . . . . ? C21 P1 N1 N2 -133.1(2) . . . . ? C11 P1 N1 N2 115.9(2) . . . . ? P1 N1 N2 N3 -9.6(3) . . . . ? N1 N2 N3 C51 173.5(2) . . . . ? N1 N2 N3 B1 3.6(4) . . . . ? C41 B1 N3 N2 147.2(2) . . . . ? C31 B1 N3 N2 -91.1(3) . . . . ? C1 B1 N3 N2 27.9(3) . . . . ? C41 B1 N3 C51 -21.5(3) . . . . ? C31 B1 N3 C51 100.1(2) . . . . ? C1 B1 N3 C51 -140.8(2) . . . . ? N1 P1 C11 C16 36.2(2) . . . . ? C1 P1 C11 C16 159.8(2) . . . . ? C21 P1 C11 C16 -71.7(2) . . . . ? N1 P1 C11 C12 -137.7(2) . . . . ? C1 P1 C11 C12 -14.0(3) . . . . ? C21 P1 C11 C12 114.5(2) . . . . ? C16 C11 C12 F12 177.5(2) . . . . ? P1 C11 C12 F12 -8.5(4) . . . . ? C16 C11 C12 C13 -3.7(4) . . . . ? P1 C11 C12 C13 170.3(2) . . . . ? F12 C12 C13 F13 2.7(4) . . . . ? C11 C12 C13 F13 -176.2(2) . . . . ? F12 C12 C13 C14 -179.8(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? F13 C13 C14 F14 -0.7(4) . . . . ? C12 C13 C14 F14 -178.2(3) . . . . ? F13 C13 C14 C15 178.7(3) . . . . ? C12 C13 C14 C15 1.3(4) . . . . ? F14 C14 C15 F15 -2.4(4) . . . . ? C13 C14 C15 F15 178.1(3) . . . . ? F14 C14 C15 C16 178.3(3) . . . . ? C13 C14 C15 C16 -1.2(4) . . . . ? F15 C15 C16 F16 -2.0(4) . . . . ? C14 C15 C16 F16 177.3(3) . . . . ? F15 C15 C16 C11 179.2(3) . . . . ? C14 C15 C16 C11 -1.5(5) . . . . ? C12 C11 C16 F16 -175.0(2) . . . . ? P1 C11 C16 F16 10.5(3) . . . . ? C12 C11 C16 C15 3.8(4) . . . . ? P1 C11 C16 C15 -170.6(2) . . . . ? N1 P1 C21 C22 -124.0(2) . . . . ? C1 P1 C21 C22 120.8(2) . . . . ? C11 P1 C21 C22 -12.8(3) . . . . ? N1 P1 C21 C26 54.6(2) . . . . ? C1 P1 C21 C26 -60.6(2) . . . . ? C11 P1 C21 C26 165.8(2) . . . . ? C26 C21 C22 F22 178.6(2) . . . . ? P1 C21 C22 F22 -2.7(4) . . . . ? C26 C21 C22 C23 -0.3(4) . . . . ? P1 C21 C22 C23 178.4(2) . . . . ? F22 C22 C23 F23 1.2(4) . . . . ? C21 C22 C23 F23 -179.8(3) . . . . ? F22 C22 C23 C24 -178.8(3) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? F23 C23 C24 F24 -0.3(4) . . . . ? C22 C23 C24 F24 179.7(3) . . . . ? F23 C23 C24 C25 179.9(3) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? F24 C24 C25 F25 1.5(4) . . . . ? C23 C24 C25 F25 -178.7(3) . . . . ? F24 C24 C25 C26 -179.7(2) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? F25 C25 C26 F26 -2.6(4) . . . . ? C24 C25 C26 F26 178.5(2) . . . . ? F25 C25 C26 C21 178.6(2) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? C22 C21 C26 F26 -178.4(2) . . . . ? P1 C21 C26 F26 2.8(3) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? P1 C21 C26 C25 -178.4(2) . . . . ? N3 B1 C31 C36 29.9(3) . . . . ? C41 B1 C31 C36 146.4(2) . . . . ? C1 B1 C31 C36 -89.1(3) . . . . ? N3 B1 C31 C32 -154.0(2) . . . . ? C41 B1 C31 C32 -37.5(3) . . . . ? C1 B1 C31 C32 86.9(3) . . . . ? C36 C31 C32 F32 179.4(2) . . . . ? B1 C31 C32 F32 2.8(4) . . . . ? C36 C31 C32 C33 -2.5(4) . . . . ? B1 C31 C32 C33 -179.0(3) . . . . ? F32 C32 C33 F33 1.1(4) . . . . ? C31 C32 C33 F33 -177.2(3) . . . . ? F32 C32 C33 C34 -177.1(3) . . . . ? C31 C32 C33 C34 4.6(5) . . . . ? F33 C33 C34 F34 -1.0(4) . . . . ? C32 C33 C34 F34 177.2(3) . . . . ? F33 C33 C34 C35 178.4(3) . . . . ? C32 C33 C34 C35 -3.4(4) . . . . ? F34 C34 C35 F35 -1.4(4) . . . . ? C33 C34 C35 F35 179.2(3) . . . . ? F34 C34 C35 C36 179.8(2) . . . . ? C33 C34 C35 C36 0.4(4) . . . . ? F35 C35 C36 F36 0.8(3) . . . . ? C34 C35 C36 F36 179.6(2) . . . . ? F35 C35 C36 C31 -177.1(2) . . . . ? C34 C35 C36 C31 1.7(4) . . . . ? C32 C31 C36 F36 -178.4(2) . . . . ? B1 C31 C36 F36 -2.0(4) . . . . ? C32 C31 C36 C35 -0.7(4) . . . . ? B1 C31 C36 C35 175.8(2) . . . . ? N3 B1 C41 C42 84.3(3) . . . . ? C31 B1 C41 C42 -36.4(3) . . . . ? C1 B1 C41 C42 -158.9(2) . . . . ? N3 B1 C41 C46 -90.6(3) . . . . ? C31 B1 C41 C46 148.7(2) . . . . ? C1 B1 C41 C46 26.2(3) . . . . ? C46 C41 C42 F42 180.0(2) . . . . ? B1 C41 C42 F42 4.4(4) . . . . ? C46 C41 C42 C43 0.2(4) . . . . ? B1 C41 C42 C43 -175.3(3) . . . . ? F42 C42 C43 F43 0.8(4) . . . . ? C41 C42 C43 F43 -179.4(3) . . . . ? F42 C42 C43 C44 -179.9(3) . . . . ? C41 C42 C43 C44 -0.2(5) . . . . ? F43 C43 C44 F44 -1.1(5) . . . . ? C42 C43 C44 F44 179.7(3) . . . . ? F43 C43 C44 C45 179.1(3) . . . . ? C42 C43 C44 C45 -0.1(5) . . . . ? F44 C44 C45 F45 0.9(5) . . . . ? C43 C44 C45 F45 -179.3(3) . . . . ? F44 C44 C45 C46 -179.4(3) . . . . ? C43 C44 C45 C46 0.3(5) . . . . ? F45 C45 C46 F46 -0.6(4) . . . . ? C44 C45 C46 F46 179.7(3) . . . . ? F45 C45 C46 C41 179.3(3) . . . . ? C44 C45 C46 C41 -0.3(5) . . . . ? C42 C41 C46 F46 180.0(2) . . . . ? B1 C41 C46 F46 -4.7(4) . . . . ? C42 C41 C46 C45 0.0(4) . . . . ? B1 C41 C46 C45 175.4(3) . . . . ? N2 N3 C51 C52 105.3(3) . . . . ? B1 N3 C51 C52 -84.2(3) . . . . ? N2 N3 C51 C56 -73.1(3) . . . . ? B1 N3 C51 C56 97.5(3) . . . . ? C56 C51 C52 C53 -6.9(4) . . . . ? N3 C51 C52 C53 174.8(2) . . . . ? C56 C51 C52 C57 170.3(3) . . . . ? N3 C51 C52 C57 -8.0(4) . . . . ? C51 C52 C53 C54 1.5(4) . . . . ? C57 C52 C53 C54 -175.9(3) . . . . ? C52 C53 C54 C55 4.1(4) . . . . ? C52 C53 C54 C58 -177.1(3) . . . . ? C53 C54 C55 C56 -4.5(4) . . . . ? C58 C54 C55 C56 176.6(3) . . . . ? C54 C55 C56 C51 -0.6(4) . . . . ? C54 C55 C56 C59 177.0(3) . . . . ? C52 C51 C56 C55 6.5(4) . . . . ? N3 C51 C56 C55 -175.2(2) . . . . ? C52 C51 C56 C59 -171.0(3) . . . . ? N3 C51 C56 C59 7.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.52 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.198 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.049