# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Douglas W Stephan' _publ_contact_author_email DSTEPHAN@CHEM.UTORONTO.CA _publ_section_title ; 1,4-Addition Reactions of Frustrated Lewis Pairs to 1,3-Dienes ; loop_ _publ_author_name 'Douglas W Stephan' 'Alan Lough' 'Kelvin S H Seto' 'Matthias Ullrich' # Attachment 'CIFs' data_t-Bu3P(CH2C(Me)-C(Me)CH2)B(C6F5)3 _database_code_depnum_ccdc_archive 'CCDC 716691' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C36 H37 B F15 P' _chemical_formula_sum 'C36 H37 B F15 P' _chemical_formula_weight 796.44 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' 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.2350(6) _cell_length_b 17.4496(9) _cell_length_c 14.7710(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.096(3) _cell_angle_gamma 90.00 _cell_volume 3654.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 24270 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.178 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14474 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.51 _reflns_number_total 14474 _reflns_number_gt 9224 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0601P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(10) _refine_ls_number_reflns 14474 _refine_ls_number_parameters 978 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1A C 0.6373(3) 0.3238(2) 0.8552(3) 0.0308(9) Uani 1 1 d . . . H1AA H 0.6940 0.3398 0.8943 0.037 Uiso 1 1 calc R . . H1AB H 0.6119 0.3707 0.8240 0.037 Uiso 1 1 calc R . . C2A C 0.5647(3) 0.2994(2) 0.9192(3) 0.0323(10) Uani 1 1 d . . . C3A C 0.4760(3) 0.3234(2) 0.9102(3) 0.0295(9) Uani 1 1 d . . . C4A C 0.4323(3) 0.3734(2) 0.8345(2) 0.0306(10) Uani 1 1 d . . . H4AA H 0.3827 0.3432 0.7993 0.037 Uiso 1 1 calc R . . H4AB H 0.4814 0.3851 0.7932 0.037 Uiso 1 1 calc R . . C5A C 0.5998(3) 0.2493(3) 0.9986(3) 0.0499(13) Uani 1 1 d . . . H5AA H 0.5842 0.2733 1.0554 0.075 Uiso 1 1 calc R . . H5AB H 0.6683 0.2433 0.9996 0.075 Uiso 1 1 calc R . . H5AC H 0.5696 0.1989 0.9923 0.075 Uiso 1 1 calc R . . C6A C 0.4098(3) 0.2982(3) 0.9792(3) 0.0383(10) Uani 1 1 d . . . H6AA H 0.4386 0.3089 1.0407 0.058 Uiso 1 1 calc R . . H6AB H 0.3976 0.2431 0.9727 0.058 Uiso 1 1 calc R . . H6AC H 0.3501 0.3263 0.9691 0.058 Uiso 1 1 calc R . . P1A P 0.67947(7) 0.26175(6) 0.76607(7) 0.0287(2) Uani 1 1 d . . . C11A C 0.5806(3) 0.2065(2) 0.7022(3) 0.0349(10) Uani 1 1 d . . . C12A C 0.6180(3) 0.1439(3) 0.6419(3) 0.0431(11) Uani 1 1 d . . . H12A H 0.5656 0.1223 0.6026 0.065 Uiso 1 1 calc R . . H12B H 0.6480 0.1034 0.6803 0.065 Uiso 1 1 calc R . . H12C H 0.6644 0.1662 0.6044 0.065 Uiso 1 1 calc R . . C13A C 0.5174(3) 0.2606(3) 0.6388(3) 0.0413(11) Uani 1 1 d . . . H13A H 0.4629 0.2320 0.6112 0.062 Uiso 1 1 calc R . . H13B H 0.5541 0.2805 0.5908 0.062 Uiso 1 1 calc R . . H13C H 0.4955 0.3034 0.6743 0.062 Uiso 1 1 calc R . . C14A C 0.5151(3) 0.1704(3) 0.7690(3) 0.0411(11) Uani 1 1 d . . . H14A H 0.4711 0.1349 0.7359 0.062 Uiso 1 1 calc R . . H14B H 0.4796 0.2109 0.7966 0.062 Uiso 1 1 calc R . . H14C H 0.5532 0.1424 0.8167 0.062 Uiso 1 1 calc R . . C21A C 0.7736(3) 0.1940(3) 0.8180(3) 0.0419(12) Uani 1 1 d . . . C22A C 0.8376(3) 0.1666(3) 0.7461(3) 0.0561(15) Uani 1 1 d . . . H22A H 0.8817 0.1280 0.7729 0.084 Uiso 1 1 calc R . . H22B H 0.8730 0.2103 0.7249 0.084 Uiso 1 1 calc R . . H22C H 0.7989 0.1441 0.6947 0.084 Uiso 1 1 calc R . . C23A C 0.7298(3) 0.1227(3) 0.8594(3) 0.0482(12) Uani 1 1 d . . . H23A H 0.7800 0.0873 0.8818 0.072 Uiso 1 1 calc R . . H23B H 0.6875 0.0971 0.8128 0.072 Uiso 1 1 calc R . . H23C H 0.6939 0.1384 0.9100 0.072 Uiso 1 1 calc R . . C24A C 0.8356(3) 0.2320(3) 0.8954(3) 0.0511(13) Uani 1 1 d . . . H24A H 0.8879 0.1977 0.9155 0.077 Uiso 1 1 calc R . . H24B H 0.7979 0.2423 0.9464 0.077 Uiso 1 1 calc R . . H24C H 0.8608 0.2803 0.8738 0.077 Uiso 1 1 calc R . . C31A C 0.7334(3) 0.3343(2) 0.6906(3) 0.0315(9) Uani 1 1 d . . . C32A C 0.7574(3) 0.3003(3) 0.5990(3) 0.0425(11) Uani 1 1 d . . . H32A H 0.7904 0.3389 0.5654 0.064 Uiso 1 1 calc R . . H32B H 0.6991 0.2852 0.5633 0.064 Uiso 1 1 calc R . . H32C H 0.7980 0.2553 0.6102 0.064 Uiso 1 1 calc R . . C33A C 0.8235(3) 0.3676(3) 0.7397(3) 0.0482(13) Uani 1 1 d . . . H33A H 0.8413 0.4142 0.7085 0.072 Uiso 1 1 calc R . . H33B H 0.8745 0.3299 0.7394 0.072 Uiso 1 1 calc R . . H33C H 0.8124 0.3799 0.8026 0.072 Uiso 1 1 calc R . . C34A C 0.6661(3) 0.4041(3) 0.6697(3) 0.0371(10) Uani 1 1 d . . . H34A H 0.6936 0.4386 0.6268 0.056 Uiso 1 1 calc R . . H34B H 0.6578 0.4317 0.7262 0.056 Uiso 1 1 calc R . . H34C H 0.6047 0.3857 0.6430 0.056 Uiso 1 1 calc R . . B1A B 0.3846(3) 0.4559(3) 0.8641(3) 0.0278(10) Uani 1 1 d . . . C41A C 0.4532(3) 0.4815(2) 0.9563(3) 0.0289(9) Uani 1 1 d . . . C42A C 0.4316(3) 0.4793(2) 1.0455(3) 0.0314(10) Uani 1 1 d . . . F42A F 0.34222(16) 0.46424(14) 1.06591(14) 0.0365(6) Uani 1 1 d . . . C43A C 0.4967(3) 0.4882(2) 1.1198(3) 0.0372(11) Uani 1 1 d . . . F43A F 0.46991(19) 0.48397(16) 1.20453(16) 0.0522(7) Uani 1 1 d . . . C44A C 0.5895(3) 0.5016(3) 1.1053(3) 0.0452(12) Uani 1 1 d . . . F44A F 0.65436(19) 0.50903(18) 1.17927(18) 0.0617(8) Uani 1 1 d . . . C45A C 0.6149(3) 0.5058(3) 1.0209(3) 0.0399(11) Uani 1 1 d . . . F45A F 0.70639(17) 0.51851(19) 1.0046(2) 0.0626(8) Uani 1 1 d . . . C46A C 0.5487(3) 0.4962(2) 0.9483(3) 0.0334(10) Uani 1 1 d . . . F46A F 0.58079(15) 0.50028(14) 0.86406(15) 0.0396(6) Uani 1 1 d . . . C51A C 0.2705(3) 0.4538(2) 0.8789(2) 0.0289(9) Uani 1 1 d . . . C52A C 0.2257(3) 0.5201(3) 0.9041(3) 0.0324(10) Uani 1 1 d . . . F52A F 0.27852(16) 0.58450(14) 0.92412(15) 0.0382(6) Uani 1 1 d . . . C53A C 0.1311(3) 0.5284(3) 0.9123(3) 0.0362(10) Uani 1 1 d . . . F53A F 0.09453(18) 0.59646(16) 0.93681(18) 0.0520(7) Uani 1 1 d . . . C54A C 0.0726(3) 0.4675(3) 0.8937(3) 0.0387(11) Uani 1 1 d . . . F54A F -0.02145(16) 0.47256(18) 0.89995(18) 0.0575(8) Uani 1 1 d . . . C55A C 0.1114(3) 0.3988(3) 0.8676(3) 0.0376(11) Uani 1 1 d . . . F55A F 0.05550(17) 0.33819(18) 0.84927(19) 0.0563(7) Uani 1 1 d . . . C56A C 0.2080(3) 0.3946(3) 0.8606(3) 0.0330(10) Uani 1 1 d . . . F56A F 0.23596(16) 0.32477(14) 0.83456(17) 0.0442(6) Uani 1 1 d . . . C61A C 0.3914(3) 0.5188(2) 0.7809(3) 0.0293(9) Uani 1 1 d . . . C62A C 0.4212(3) 0.5941(3) 0.7903(3) 0.0319(10) Uani 1 1 d . . . F62A F 0.45465(17) 0.62310(13) 0.87102(15) 0.0396(6) Uani 1 1 d . . . C63A C 0.4205(3) 0.6466(3) 0.7187(3) 0.0414(11) Uani 1 1 d . . . F63A F 0.45008(19) 0.71934(15) 0.73404(17) 0.0499(7) Uani 1 1 d . . . C64A C 0.3899(3) 0.6235(3) 0.6323(3) 0.0425(12) Uani 1 1 d . . . F64A F 0.3887(2) 0.67444(17) 0.56300(17) 0.0618(8) Uani 1 1 d . . . C65A C 0.3594(3) 0.5502(3) 0.6189(3) 0.0401(11) Uani 1 1 d . . . F65A F 0.3264(2) 0.52734(17) 0.53399(16) 0.0570(8) Uani 1 1 d . . . C66A C 0.3597(3) 0.5001(2) 0.6915(3) 0.0321(10) Uani 1 1 d . . . F66A F 0.32426(17) 0.42922(15) 0.67268(15) 0.0433(6) Uani 1 1 d . . . C1B C 0.1101(3) 0.2277(2) 0.3744(3) 0.0317(10) Uani 1 1 d . . . H1BA H 0.0477 0.2179 0.3412 0.038 Uiso 1 1 calc R . . H1BB H 0.1360 0.1770 0.3935 0.038 Uiso 1 1 calc R . . C2B C 0.0907(3) 0.2694(2) 0.4611(3) 0.0297(9) Uani 1 1 d . . . C3B C 0.1329(3) 0.2480(2) 0.5432(2) 0.0278(9) Uani 1 1 d . . . C4B C 0.2029(3) 0.1826(2) 0.5584(3) 0.0281(9) Uani 1 1 d . . . H4BA H 0.2551 0.2002 0.6023 0.034 Uiso 1 1 calc R . . H4BB H 0.2301 0.1723 0.5002 0.034 Uiso 1 1 calc R . . C5B C 0.0125(3) 0.3283(3) 0.4521(3) 0.0407(11) Uani 1 1 d . . . H5BA H -0.0068 0.3406 0.5125 0.061 Uiso 1 1 calc R . . H5BB H -0.0415 0.3075 0.4141 0.061 Uiso 1 1 calc R . . H5BC H 0.0351 0.3748 0.4240 0.061 Uiso 1 1 calc R . . C6B C 0.1166(3) 0.2910(3) 0.6290(3) 0.0389(11) Uani 1 1 d . . . H6BA H 0.0499 0.3053 0.6278 0.058 Uiso 1 1 calc R . . H6BB H 0.1556 0.3373 0.6331 0.058 Uiso 1 1 calc R . . H6BC H 0.1336 0.2582 0.6818 0.058 Uiso 1 1 calc R . . P1B P 0.18689(8) 0.26476(7) 0.28845(7) 0.0329(3) Uani 1 1 d . . . C11B C 0.2744(3) 0.3377(3) 0.3394(3) 0.0433(11) Uani 1 1 d . . . C12B C 0.3542(4) 0.3517(3) 0.2794(4) 0.0623(15) Uani 1 1 d . . . H12D H 0.3900 0.3971 0.3011 0.093 Uiso 1 1 calc R . . H12E H 0.3279 0.3601 0.2166 0.093 Uiso 1 1 calc R . . H12F H 0.3960 0.3070 0.2818 0.093 Uiso 1 1 calc R . . C13B C 0.3178(3) 0.3133(3) 0.4341(3) 0.0462(12) Uani 1 1 d . . . H13D H 0.3656 0.3508 0.4564 0.069 Uiso 1 1 calc R . . H13E H 0.3471 0.2628 0.4301 0.069 Uiso 1 1 calc R . . H13F H 0.2683 0.3109 0.4760 0.069 Uiso 1 1 calc R . . C14B C 0.2243(4) 0.4146(3) 0.3535(3) 0.0504(13) Uani 1 1 d . . . H14D H 0.2688 0.4505 0.3851 0.076 Uiso 1 1 calc R . . H14E H 0.1710 0.4062 0.3900 0.076 Uiso 1 1 calc R . . H14F H 0.2011 0.4359 0.2943 0.076 Uiso 1 1 calc R . . C21B C 0.1071(3) 0.3067(3) 0.1914(3) 0.0431(12) Uani 1 1 d . . . C22B C 0.1607(4) 0.3558(3) 0.1255(3) 0.0553(14) Uani 1 1 d . . . H22D H 0.1169 0.3725 0.0744 0.083 Uiso 1 1 calc R . . H22E H 0.2113 0.3253 0.1027 0.083 Uiso 1 1 calc R . . H22F H 0.1878 0.4008 0.1578 0.083 Uiso 1 1 calc R . . C23B C 0.0333(3) 0.3573(3) 0.2293(3) 0.0496(13) Uani 1 1 d . . . H23D H -0.0018 0.3850 0.1794 0.074 Uiso 1 1 calc R . . H23E H 0.0642 0.3941 0.2722 0.074 Uiso 1 1 calc R . . H23F H -0.0103 0.3254 0.2607 0.074 Uiso 1 1 calc R . . C24B C 0.0556(3) 0.2431(3) 0.1359(3) 0.0494(13) Uani 1 1 d . . . H24D H 0.0108 0.2658 0.0893 0.074 Uiso 1 1 calc R . . H24E H 0.0216 0.2106 0.1762 0.074 Uiso 1 1 calc R . . H24F H 0.1015 0.2119 0.1066 0.074 Uiso 1 1 calc R . . C31B C 0.2496(3) 0.1761(3) 0.2484(3) 0.0449(12) Uani 1 1 d . . . C32B C 0.2925(4) 0.1912(3) 0.1584(3) 0.0596(15) Uani 1 1 d . . . H32D H 0.3290 0.1463 0.1423 0.089 Uiso 1 1 calc R . . H32E H 0.3340 0.2360 0.1651 0.089 Uiso 1 1 calc R . . H32F H 0.2419 0.2008 0.1104 0.089 Uiso 1 1 calc R . . C33B C 0.1812(4) 0.1074(3) 0.2351(3) 0.0520(13) Uani 1 1 d . . . H33D H 0.2137 0.0642 0.2093 0.078 Uiso 1 1 calc R . . H33E H 0.1266 0.1221 0.1937 0.078 Uiso 1 1 calc R . . H33F H 0.1600 0.0925 0.2939 0.078 Uiso 1 1 calc R . . C34B C 0.3294(3) 0.1513(3) 0.3202(3) 0.0551(14) Uani 1 1 d . . . H34D H 0.3598 0.1049 0.2994 0.083 Uiso 1 1 calc R . . H34E H 0.3030 0.1408 0.3779 0.083 Uiso 1 1 calc R . . H34F H 0.3762 0.1925 0.3288 0.083 Uiso 1 1 calc R . . B1B B 0.1626(3) 0.1003(3) 0.5963(3) 0.0249(10) Uani 1 1 d . . . C41B C 0.0695(3) 0.0784(2) 0.5252(2) 0.0239(8) Uani 1 1 d . . . C42B C -0.0151(3) 0.1179(2) 0.5281(2) 0.0289(9) Uani 1 1 d . . . F42B F -0.02862(15) 0.16598(14) 0.59647(14) 0.0333(5) Uani 1 1 d . . . C43B C -0.0906(3) 0.1111(3) 0.4636(3) 0.0404(11) Uani 1 1 d . . . F43B F -0.17060(17) 0.15118(19) 0.47129(18) 0.0615(9) Uani 1 1 d . . . C44B C -0.0842(3) 0.0643(3) 0.3907(3) 0.0458(13) Uani 1 1 d . . . F44B F -0.15726(18) 0.0559(2) 0.3251(2) 0.0764(11) Uani 1 1 d . . . C45B C -0.0032(3) 0.0221(3) 0.3842(3) 0.0347(10) Uani 1 1 d . . . F45B F 0.00420(17) -0.02538(16) 0.31305(16) 0.0489(7) Uani 1 1 d . . . C46B C 0.0701(3) 0.0313(2) 0.4497(3) 0.0279(9) Uani 1 1 d . . . F46B F 0.15012(15) -0.00868(14) 0.43479(14) 0.0370(6) Uani 1 1 d . . . C51B C 0.1386(3) 0.1023(2) 0.7044(2) 0.0246(8) Uani 1 1 d . . . C52B C 0.0625(3) 0.0682(2) 0.7414(3) 0.0291(9) Uani 1 1 d . . . F52B F -0.00586(14) 0.03195(13) 0.68697(14) 0.0337(5) Uani 1 1 d . . . C53B C 0.0504(3) 0.0656(2) 0.8331(3) 0.0323(10) Uani 1 1 d . . . F53B F -0.02539(16) 0.03030(14) 0.86355(15) 0.0393(6) Uani 1 1 d . . . C54B C 0.1144(3) 0.1009(3) 0.8942(3) 0.0343(10) Uani 1 1 d . . . F54B F 0.10311(18) 0.09986(16) 0.98367(15) 0.0469(7) Uani 1 1 d . . . C55B C 0.1910(3) 0.1352(2) 0.8621(3) 0.0301(10) Uani 1 1 d . . . F55B F 0.25639(19) 0.16810(16) 0.92165(15) 0.0502(7) Uani 1 1 d . . . C56B C 0.2030(3) 0.1341(2) 0.7720(3) 0.0324(10) Uani 1 1 d . . . F56B F 0.28331(15) 0.16643(14) 0.74790(15) 0.0374(6) Uani 1 1 d . . . C61B C 0.2448(3) 0.0321(2) 0.5960(2) 0.0242(8) Uani 1 1 d . . . C62B C 0.2252(3) -0.0424(2) 0.6168(3) 0.0282(9) Uani 1 1 d . . . F62B F 0.13596(15) -0.05921(13) 0.63893(17) 0.0390(6) Uani 1 1 d . . . C63B C 0.2853(3) -0.1040(2) 0.6163(3) 0.0333(10) Uani 1 1 d . . . F63B F 0.25616(18) -0.17564(14) 0.63350(19) 0.0535(7) Uani 1 1 d . . . C64B C 0.3750(3) -0.0920(3) 0.5934(3) 0.0362(11) Uani 1 1 d . . . F64B F 0.43623(17) -0.15120(15) 0.5895(2) 0.0545(7) Uani 1 1 d . . . C65B C 0.4027(3) -0.0197(3) 0.5735(3) 0.0346(10) Uani 1 1 d . . . F65B F 0.49076(16) -0.00736(16) 0.55091(19) 0.0512(7) Uani 1 1 d . . . C66B C 0.3388(3) 0.0405(2) 0.5746(3) 0.0309(10) Uani 1 1 d . . . F66B F 0.37456(15) 0.10913(14) 0.55269(16) 0.0377(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 C1A 0.034(2) 0.032(2) 0.027(2) 0.0039(18) 0.0043(17) 0.0020(19) C2A 0.042(3) 0.029(2) 0.027(2) 0.0024(18) 0.0116(19) 0.005(2) C3A 0.036(2) 0.024(2) 0.030(2) -0.0096(18) 0.0110(18) -0.0008(19) C4A 0.035(2) 0.032(3) 0.026(2) -0.0033(18) 0.0080(18) -0.0018(19) C5A 0.057(3) 0.056(3) 0.040(2) 0.015(2) 0.025(2) 0.018(3) C6A 0.048(3) 0.030(2) 0.039(2) -0.001(2) 0.015(2) -0.001(2) P1A 0.0295(5) 0.0292(6) 0.0286(5) 0.0051(5) 0.0094(4) 0.0020(5) C11A 0.041(2) 0.030(2) 0.035(2) -0.0054(19) 0.0108(19) -0.004(2) C12A 0.057(3) 0.032(3) 0.043(3) -0.003(2) 0.017(2) -0.001(2) C13A 0.045(2) 0.039(3) 0.039(2) -0.007(2) -0.002(2) -0.007(2) C14A 0.041(2) 0.036(3) 0.048(3) -0.004(2) 0.011(2) -0.009(2) C21A 0.040(3) 0.044(3) 0.043(3) 0.012(2) 0.012(2) 0.013(2) C22A 0.050(3) 0.067(4) 0.055(3) 0.026(3) 0.029(2) 0.036(3) C23A 0.050(3) 0.045(3) 0.053(3) 0.020(2) 0.019(2) 0.018(2) C24A 0.037(3) 0.071(4) 0.045(3) 0.019(3) 0.004(2) 0.010(2) C31A 0.032(2) 0.034(3) 0.029(2) 0.0068(19) 0.0074(17) -0.0008(19) C32A 0.047(3) 0.049(3) 0.034(2) 0.007(2) 0.017(2) -0.003(2) C33A 0.043(3) 0.056(3) 0.048(3) 0.005(2) 0.017(2) -0.010(2) C34A 0.051(3) 0.034(3) 0.027(2) 0.0104(19) 0.0096(19) -0.002(2) B1A 0.033(3) 0.022(3) 0.029(2) 0.000(2) 0.006(2) 0.001(2) C41A 0.035(2) 0.020(2) 0.032(2) -0.0024(17) 0.0085(18) 0.0005(18) C42A 0.028(2) 0.025(2) 0.041(2) -0.0034(19) 0.0040(19) -0.0034(18) F42A 0.0440(14) 0.0384(15) 0.0283(12) -0.0011(11) 0.0095(10) -0.0051(11) C43A 0.056(3) 0.024(2) 0.030(2) -0.0031(19) -0.003(2) -0.008(2) F43A 0.0701(18) 0.0532(18) 0.0322(13) 0.0032(12) -0.0010(13) -0.0210(14) C44A 0.047(3) 0.043(3) 0.042(3) -0.004(2) -0.011(2) -0.013(2) F44A 0.0585(17) 0.072(2) 0.0505(16) -0.0034(15) -0.0202(14) -0.0178(16) C45A 0.032(2) 0.041(3) 0.046(3) -0.006(2) -0.004(2) -0.005(2) F45A 0.0334(15) 0.079(2) 0.0739(19) -0.0172(17) -0.0023(13) -0.0128(15) C46A 0.033(2) 0.030(2) 0.037(2) -0.006(2) 0.0034(19) 0.0012(19) F46A 0.0352(13) 0.0447(16) 0.0398(13) -0.0066(12) 0.0087(11) -0.0022(12) C51A 0.036(2) 0.031(2) 0.0193(19) 0.0025(17) 0.0053(17) 0.001(2) C52A 0.032(2) 0.037(3) 0.029(2) -0.0017(19) 0.0057(18) -0.003(2) F52A 0.0384(13) 0.0355(15) 0.0421(14) -0.0088(11) 0.0107(11) -0.0007(11) C53A 0.036(2) 0.037(3) 0.036(2) -0.005(2) 0.0066(19) 0.012(2) F53A 0.0482(15) 0.0485(18) 0.0613(17) -0.0088(14) 0.0150(13) 0.0157(14) C54A 0.024(2) 0.059(3) 0.033(2) 0.002(2) 0.0056(18) 0.007(2) F54A 0.0282(14) 0.084(2) 0.0611(17) -0.0090(16) 0.0059(12) 0.0041(14) C55A 0.032(2) 0.044(3) 0.035(2) -0.005(2) -0.0007(19) -0.003(2) F55A 0.0334(14) 0.0612(19) 0.0740(19) -0.0161(16) 0.0026(13) -0.0119(14) C56A 0.034(2) 0.032(3) 0.034(2) -0.009(2) 0.0062(19) -0.003(2) F56A 0.0369(13) 0.0371(16) 0.0583(16) -0.0137(13) 0.0031(12) -0.0031(12) C61A 0.0234(19) 0.036(3) 0.030(2) -0.0072(19) 0.0074(17) -0.0060(18) C62A 0.033(2) 0.036(3) 0.027(2) -0.0043(19) 0.0098(18) 0.000(2) F62A 0.0554(15) 0.0312(14) 0.0328(13) -0.0074(11) 0.0080(11) -0.0060(12) C63A 0.043(3) 0.038(3) 0.046(3) -0.004(2) 0.014(2) -0.006(2) F63A 0.0665(18) 0.0336(16) 0.0503(15) 0.0040(12) 0.0097(13) -0.0125(14) C64A 0.043(3) 0.050(3) 0.035(2) 0.011(2) 0.010(2) -0.006(2) F64A 0.087(2) 0.060(2) 0.0379(15) 0.0135(14) 0.0045(14) -0.0125(17) C65A 0.046(3) 0.048(3) 0.027(2) -0.002(2) 0.006(2) 0.003(2) F65A 0.0709(18) 0.069(2) 0.0292(13) -0.0019(14) -0.0046(13) -0.0066(16) C66A 0.037(2) 0.024(2) 0.035(2) -0.0093(19) 0.0027(19) -0.0018(19) F66A 0.0545(15) 0.0413(16) 0.0326(13) -0.0058(11) -0.0043(11) -0.0102(13) C1B 0.037(2) 0.029(2) 0.030(2) 0.0067(18) 0.0055(18) 0.0014(19) C2B 0.031(2) 0.026(2) 0.033(2) -0.0041(19) 0.0062(17) 0.0000(19) C3B 0.032(2) 0.023(2) 0.029(2) -0.0022(17) 0.0080(17) 0.0030(18) C4B 0.031(2) 0.032(2) 0.0220(19) -0.0027(17) 0.0013(17) 0.0008(18) C5B 0.043(3) 0.044(3) 0.036(2) 0.004(2) 0.008(2) 0.017(2) C6B 0.049(3) 0.031(3) 0.037(2) -0.0027(19) 0.005(2) 0.005(2) P1B 0.0414(6) 0.0304(6) 0.0276(5) 0.0031(5) 0.0070(5) 0.0009(5) C11B 0.045(3) 0.040(3) 0.046(3) 0.007(2) 0.008(2) -0.009(2) C12B 0.065(3) 0.061(4) 0.060(3) 0.020(3) 0.006(3) -0.020(3) C13B 0.045(3) 0.050(3) 0.043(3) 0.002(2) 0.003(2) -0.013(2) C14B 0.070(3) 0.032(3) 0.048(3) -0.003(2) -0.004(2) -0.012(2) C21B 0.058(3) 0.036(3) 0.034(2) 0.000(2) -0.003(2) 0.007(2) C22B 0.082(4) 0.054(3) 0.030(2) 0.009(2) 0.008(2) 0.004(3) C23B 0.060(3) 0.051(3) 0.037(3) 0.002(2) -0.001(2) 0.010(3) C24B 0.058(3) 0.047(3) 0.041(3) -0.005(2) -0.009(2) 0.003(2) C31B 0.048(3) 0.052(3) 0.037(2) 0.012(2) 0.016(2) 0.013(2) C32B 0.074(4) 0.066(4) 0.043(3) -0.003(3) 0.028(3) 0.005(3) C33B 0.079(4) 0.030(3) 0.049(3) 0.001(2) 0.018(3) 0.015(3) C34B 0.054(3) 0.067(4) 0.046(3) 0.011(3) 0.018(2) 0.016(3) B1B 0.024(2) 0.026(3) 0.024(2) 0.0007(19) -0.0009(18) 0.0025(19) C41B 0.026(2) 0.026(2) 0.0216(19) 0.0011(17) 0.0094(16) 0.0009(17) C42B 0.030(2) 0.030(2) 0.027(2) -0.0015(18) 0.0040(17) 0.0022(18) F42B 0.0288(12) 0.0417(15) 0.0300(12) -0.0077(11) 0.0067(10) 0.0062(11) C43B 0.024(2) 0.060(3) 0.037(2) -0.015(2) 0.0016(18) 0.010(2) F43B 0.0284(13) 0.097(2) 0.0570(17) -0.0292(17) -0.0062(12) 0.0288(14) C44B 0.023(2) 0.069(4) 0.043(3) -0.010(3) -0.013(2) 0.007(2) F44B 0.0370(15) 0.129(3) 0.0596(18) -0.0453(19) -0.0184(14) 0.0167(17) C45B 0.030(2) 0.044(3) 0.030(2) -0.011(2) 0.0046(18) 0.000(2) F45B 0.0378(14) 0.068(2) 0.0394(14) -0.0271(14) -0.0028(11) 0.0054(13) C46B 0.0214(19) 0.029(2) 0.034(2) 0.0005(19) 0.0098(17) 0.0059(18) F46B 0.0346(13) 0.0449(16) 0.0318(12) -0.0115(11) 0.0031(10) 0.0098(11) C51B 0.028(2) 0.017(2) 0.030(2) -0.0009(17) 0.0061(17) -0.0007(17) C52B 0.032(2) 0.027(2) 0.029(2) -0.0092(18) 0.0015(18) 0.0020(18) F52B 0.0297(12) 0.0380(15) 0.0332(12) -0.0038(11) 0.0016(10) -0.0064(11) C53B 0.037(2) 0.026(2) 0.035(2) 0.0047(19) 0.014(2) 0.0028(19) F53B 0.0405(13) 0.0417(16) 0.0378(13) 0.0065(12) 0.0155(11) -0.0030(12) C54B 0.048(3) 0.036(3) 0.020(2) -0.0034(18) 0.0085(19) 0.005(2) F54B 0.0624(17) 0.0542(18) 0.0254(12) -0.0018(12) 0.0114(11) -0.0016(14) C55B 0.037(2) 0.028(2) 0.024(2) -0.0074(18) -0.0042(19) -0.0029(19) F55B 0.0642(17) 0.0541(18) 0.0308(13) -0.0084(13) -0.0044(12) -0.0173(15) C56B 0.033(2) 0.033(2) 0.031(2) -0.0042(19) 0.0038(18) -0.0040(19) F56B 0.0339(13) 0.0455(15) 0.0325(12) -0.0029(11) 0.0008(10) -0.0135(12) C61B 0.0244(19) 0.026(2) 0.0225(19) -0.0041(17) 0.0044(15) -0.0002(17) C62B 0.022(2) 0.033(3) 0.030(2) 0.0010(18) 0.0019(16) -0.0053(18) F62B 0.0322(13) 0.0284(14) 0.0572(15) 0.0024(12) 0.0086(11) -0.0061(11) C63B 0.043(3) 0.017(2) 0.039(2) -0.0025(19) 0.001(2) 0.000(2) F63B 0.0526(16) 0.0239(15) 0.084(2) 0.0036(14) 0.0059(14) 0.0003(12) C64B 0.027(2) 0.031(3) 0.049(3) -0.007(2) -0.004(2) 0.0097(19) F64B 0.0434(15) 0.0361(16) 0.083(2) -0.0036(14) 0.0017(14) 0.0188(13) C65B 0.031(2) 0.033(3) 0.040(2) -0.003(2) 0.0049(19) 0.005(2) F65B 0.0256(13) 0.0486(17) 0.0817(19) 0.0008(14) 0.0173(12) 0.0097(12) C66B 0.037(2) 0.023(2) 0.033(2) -0.0026(18) 0.0017(18) 0.0030(19) F66B 0.0284(12) 0.0307(14) 0.0549(15) 0.0048(12) 0.0088(11) -0.0009(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 C1A C2A 1.521(5) . ? C1A P1A 1.846(4) . ? C2A C3A 1.327(5) . ? C2A C5A 1.512(6) . ? C3A C4A 1.507(6) . ? C3A C6A 1.514(5) . ? C4A B1A 1.667(6) . ? P1A C11A 1.887(4) . ? P1A C31A 1.894(4) . ? P1A C21A 1.897(4) . ? C11A C12A 1.534(6) . ? C11A C14A 1.550(6) . ? C11A C13A 1.559(6) . ? C21A C24A 1.533(7) . ? C21A C22A 1.535(6) . ? C21A C23A 1.542(7) . ? C31A C33A 1.531(6) . ? C31A C32A 1.543(6) . ? C31A C34A 1.563(6) . ? B1A C61A 1.656(6) . ? B1A C51A 1.658(6) . ? B1A C41A 1.666(6) . ? C41A C42A 1.381(6) . ? C41A C46A 1.398(6) . ? C42A F42A 1.359(4) . ? C42A C43A 1.380(6) . ? C43A F43A 1.343(5) . ? C43A C44A 1.377(6) . ? C44A C45A 1.330(6) . ? C44A F44A 1.372(5) . ? C45A F45A 1.363(5) . ? C45A C46A 1.374(6) . ? C46A F46A 1.365(5) . ? C51A C56A 1.375(6) . ? C51A C52A 1.388(6) . ? C52A F52A 1.369(5) . ? C52A C53A 1.371(6) . ? C53A F53A 1.358(5) . ? C53A C54A 1.364(6) . ? C54A F54A 1.353(5) . ? C54A C55A 1.388(7) . ? C55A F55A 1.337(5) . ? C55A C56A 1.390(6) . ? C56A F56A 1.348(5) . ? C61A C62A 1.385(6) . ? C61A C66A 1.396(5) . ? C62A F62A 1.342(5) . ? C62A C63A 1.399(6) . ? C63A F63A 1.351(5) . ? C63A C64A 1.371(6) . ? C64A F64A 1.354(5) . ? C64A C65A 1.360(7) . ? C65A F65A 1.359(5) . ? C65A C66A 1.383(6) . ? C66A F66A 1.356(5) . ? C1B C2B 1.520(5) . ? C1B P1B 1.863(4) . ? C2B C3B 1.356(5) . ? C2B C5B 1.512(6) . ? C3B C6B 1.508(5) . ? C3B C4B 1.518(5) . ? C4B B1B 1.662(6) . ? P1B C11B 1.889(5) . ? P1B C21B 1.895(4) . ? P1B C31B 1.907(5) . ? C11B C12B 1.522(7) . ? C11B C13B 1.538(6) . ? C11B C14B 1.543(7) . ? C21B C23B 1.517(7) . ? C21B C24B 1.528(7) . ? C21B C22B 1.547(7) . ? C31B C32B 1.534(6) . ? C31B C33B 1.545(7) . ? C31B C34B 1.546(6) . ? B1B C41B 1.661(5) . ? B1B C51B 1.663(6) . ? B1B C61B 1.669(6) . ? C41B C46B 1.386(5) . ? C41B C42B 1.392(5) . ? C42B F42B 1.340(4) . ? C42B C43B 1.376(5) . ? C43B F43B 1.350(5) . ? C43B C44B 1.360(6) . ? C44B F44B 1.364(5) . ? C44B C45B 1.379(6) . ? C45B F45B 1.350(5) . ? C45B C46B 1.368(5) . ? C46B F46B 1.370(4) . ? C51B C52B 1.389(5) . ? C51B C56B 1.408(5) . ? C52B F52B 1.362(4) . ? C52B C53B 1.382(5) . ? C53B F53B 1.354(4) . ? C53B C54B 1.370(6) . ? C54B F54B 1.345(4) . ? C54B C55B 1.366(6) . ? C55B F55B 1.350(4) . ? C55B C56B 1.356(5) . ? C56B F56B 1.351(5) . ? C61B C62B 1.369(6) . ? C61B C66B 1.411(5) . ? C62B F62B 1.371(4) . ? C62B C63B 1.374(6) . ? C63B F63B 1.348(5) . ? C63B C64B 1.366(6) . ? C64B F64B 1.357(5) . ? C64B C65B 1.361(6) . ? C65B F65B 1.343(5) . ? C65B C66B 1.390(6) . ? C66B F66B 1.352(5) . ? 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 C2A C1A P1A 124.1(3) . . ? C3A C2A C5A 120.4(4) . . ? C3A C2A C1A 122.9(4) . . ? C5A C2A C1A 116.6(4) . . ? C2A C3A C4A 125.7(4) . . ? C2A C3A C6A 119.0(4) . . ? C4A C3A C6A 115.3(3) . . ? C3A C4A B1A 117.1(3) . . ? C1A P1A C11A 112.38(18) . . ? C1A P1A C31A 101.66(19) . . ? C11A P1A C31A 111.76(19) . . ? C1A P1A C21A 109.90(19) . . ? C11A P1A C21A 110.6(2) . . ? C31A P1A C21A 110.24(19) . . ? C12A C11A C14A 109.8(4) . . ? C12A C11A C13A 107.1(3) . . ? C14A C11A C13A 106.3(4) . . ? C12A C11A P1A 111.8(3) . . ? C14A C11A P1A 110.7(3) . . ? C13A C11A P1A 110.8(3) . . ? C24A C21A C22A 108.2(4) . . ? C24A C21A C23A 106.3(4) . . ? C22A C21A C23A 108.0(4) . . ? C24A C21A P1A 111.8(3) . . ? C22A C21A P1A 110.8(3) . . ? C23A C21A P1A 111.6(3) . . ? C33A C31A C32A 108.7(3) . . ? C33A C31A C34A 105.8(4) . . ? C32A C31A C34A 107.8(3) . . ? C33A C31A P1A 110.0(3) . . ? C32A C31A P1A 113.1(3) . . ? C34A C31A P1A 111.3(3) . . ? C61A B1A C51A 103.6(3) . . ? C61A B1A C41A 111.1(3) . . ? C51A B1A C41A 114.1(3) . . ? C61A B1A C4A 109.0(3) . . ? C51A B1A C4A 116.2(3) . . ? C41A B1A C4A 102.9(3) . . ? C42A C41A C46A 112.7(4) . . ? C42A C41A B1A 127.5(4) . . ? C46A C41A B1A 119.0(3) . . ? F42A C42A C43A 114.9(4) . . ? F42A C42A C41A 120.6(3) . . ? C43A C42A C41A 124.4(4) . . ? F43A C43A C44A 120.6(4) . . ? F43A C43A C42A 120.6(4) . . ? C44A C43A C42A 118.8(4) . . ? C45A C44A F44A 121.4(4) . . ? C45A C44A C43A 119.9(4) . . ? F44A C44A C43A 118.7(4) . . ? C44A C45A F45A 121.2(4) . . ? C44A C45A C46A 120.0(4) . . ? F45A C45A C46A 118.8(4) . . ? F46A C46A C45A 116.3(4) . . ? F46A C46A C41A 119.5(3) . . ? C45A C46A C41A 124.2(4) . . ? C56A C51A C52A 112.0(4) . . ? C56A C51A B1A 128.0(4) . . ? C52A C51A B1A 119.7(4) . . ? F52A C52A C53A 114.8(4) . . ? F52A C52A C51A 119.1(3) . . ? C53A C52A C51A 126.2(4) . . ? F53A C53A C54A 119.6(4) . . ? F53A C53A C52A 121.2(4) . . ? C54A C53A C52A 119.1(4) . . ? F54A C54A C53A 121.7(4) . . ? F54A C54A C55A 119.8(4) . . ? C53A C54A C55A 118.6(4) . . ? F55A C55A C54A 119.7(4) . . ? F55A C55A C56A 121.2(4) . . ? C54A C55A C56A 119.2(4) . . ? F56A C56A C51A 122.2(4) . . ? F56A C56A C55A 112.9(4) . . ? C51A C56A C55A 125.0(4) . . ? C62A C61A C66A 112.7(4) . . ? C62A C61A B1A 126.3(3) . . ? C66A C61A B1A 120.8(4) . . ? F62A C62A C61A 121.9(4) . . ? F62A C62A C63A 113.8(4) . . ? C61A C62A C63A 124.3(4) . . ? F63A C63A C64A 120.0(4) . . ? F63A C63A C62A 120.4(4) . . ? C64A C63A C62A 119.5(4) . . ? F64A C64A C65A 121.7(4) . . ? F64A C64A C63A 119.5(4) . . ? C65A C64A C63A 118.8(4) . . ? F65A C65A C64A 119.3(4) . . ? F65A C65A C66A 120.5(4) . . ? C64A C65A C66A 120.2(4) . . ? F66A C66A C65A 116.2(3) . . ? F66A C66A C61A 119.4(4) . . ? C65A C66A C61A 124.4(4) . . ? C2B C1B P1B 124.7(3) . . ? C3B C2B C5B 122.0(3) . . ? C3B C2B C1B 121.5(4) . . ? C5B C2B C1B 116.0(3) . . ? C2B C3B C6B 121.6(4) . . ? C2B C3B C4B 124.9(3) . . ? C6B C3B C4B 113.4(3) . . ? C3B C4B B1B 117.2(3) . . ? C1B P1B C11B 111.62(19) . . ? C1B P1B C21B 107.5(2) . . ? C11B P1B C21B 111.8(2) . . ? C1B P1B C31B 104.4(2) . . ? C11B P1B C31B 111.1(2) . . ? C21B P1B C31B 110.1(2) . . ? C12B C11B C13B 108.3(4) . . ? C12B C11B C14B 108.5(4) . . ? C13B C11B C14B 105.7(4) . . ? C12B C11B P1B 112.1(3) . . ? C13B C11B P1B 111.9(3) . . ? C14B C11B P1B 110.1(3) . . ? C23B C21B C24B 107.8(4) . . ? C23B C21B C22B 107.8(4) . . ? C24B C21B C22B 107.8(4) . . ? C23B C21B P1B 109.5(3) . . ? C24B C21B P1B 110.6(3) . . ? C22B C21B P1B 113.2(3) . . ? C32B C31B C33B 108.6(4) . . ? C32B C31B C34B 108.5(4) . . ? C33B C31B C34B 106.7(4) . . ? C32B C31B P1B 111.3(4) . . ? C33B C31B P1B 111.2(3) . . ? C34B C31B P1B 110.5(3) . . ? C41B B1B C4B 105.4(3) . . ? C41B B1B C51B 113.1(3) . . ? C4B B1B C51B 114.3(3) . . ? C41B B1B C61B 110.8(3) . . ? C4B B1B C61B 110.6(3) . . ? C51B B1B C61B 102.7(3) . . ? C46B C41B C42B 112.7(3) . . ? C46B C41B B1B 125.7(3) . . ? C42B C41B B1B 120.8(3) . . ? F42B C42B C43B 114.9(3) . . ? F42B C42B C41B 121.0(3) . . ? C43B C42B C41B 124.1(4) . . ? F43B C43B C44B 119.6(3) . . ? F43B C43B C42B 120.6(4) . . ? C44B C43B C42B 119.8(4) . . ? C43B C44B F44B 121.7(4) . . ? C43B C44B C45B 119.4(4) . . ? F44B C44B C45B 118.9(4) . . ? F45B C45B C46B 121.0(3) . . ? F45B C45B C44B 120.4(3) . . ? C46B C45B C44B 118.6(4) . . ? C45B C46B F46B 114.8(3) . . ? C45B C46B C41B 125.4(4) . . ? F46B C46B C41B 119.8(3) . . ? C52B C51B C56B 111.8(3) . . ? C52B C51B B1B 127.0(3) . . ? C56B C51B B1B 120.9(3) . . ? F52B C52B C53B 114.7(4) . . ? F52B C52B C51B 120.6(3) . . ? C53B C52B C51B 124.7(4) . . ? F53B C53B C54B 119.2(4) . . ? F53B C53B C52B 120.9(4) . . ? C54B C53B C52B 119.9(4) . . ? F54B C54B C55B 121.0(4) . . ? F54B C54B C53B 120.7(4) . . ? C55B C54B C53B 118.2(4) . . ? F55B C55B C56B 120.4(4) . . ? F55B C55B C54B 119.1(3) . . ? C56B C55B C54B 120.5(4) . . ? F56B C56B C55B 115.8(3) . . ? F56B C56B C51B 119.4(3) . . ? C55B C56B C51B 124.8(4) . . ? C62B C61B C66B 111.4(3) . . ? C62B C61B B1B 121.3(3) . . ? C66B C61B B1B 127.2(3) . . ? C61B C62B F62B 117.9(3) . . ? C61B C62B C63B 127.0(4) . . ? F62B C62B C63B 115.1(3) . . ? F63B C63B C64B 119.9(4) . . ? F63B C63B C62B 121.5(4) . . ? C64B C63B C62B 118.5(4) . . ? F64B C64B C65B 119.8(4) . . ? F64B C64B C63B 120.8(4) . . ? C65B C64B C63B 119.4(4) . . ? F65B C65B C64B 119.8(4) . . ? F65B C65B C66B 120.5(4) . . ? C64B C65B C66B 119.7(4) . . ? F66B C66B C65B 114.0(3) . . ? F66B C66B C61B 122.1(3) . . ? C65B C66B C61B 123.9(4) . . ? _vrf_PLAT601_k08264 ; PROBLEM: Structure Contains Solvent Accessible VOIDS of 94.00 A**3 RESPONSE: During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecules (possibly dichloromethane and/or hexane). Attempts made to model the solvent molecule were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 107 \%A^3^ containing approximately 24 electrons. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered solvent molecules were carried out by St\"ahler et al. (2001), Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005). References: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13 Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005). Acta Cryst. E61, m2014-m2017. Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M. (2003). Acta Cryst. E59, o975-o977. Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M. (2003). Acta Cryst. C59, m84-m86. St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst. C57, 26-27. ; _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.766 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.063 _vrf_PLAT410_k08264 ; PROBLEM: Short Intra H...H Contact H1AB .. H4AB .. 1.89 Ang. RESPONSE: All H atoms were included in caculated positions as per the defaults of the refinement software. ; #===end data_Bu3PCH(CH-CH)CH(CH2CH2)B(C6F5)3 _database_code_depnum_ccdc_archive 'CCDC 716692' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C36 H35 B F15 P' _chemical_formula_sum 'C36 H35 B F15 P' _chemical_formula_weight 794.42 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' 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1460(18) _cell_length_b 13.313(3) _cell_length_c 16.843(3) _cell_angle_alpha 81.44(3) _cell_angle_beta 77.24(3) _cell_angle_gamma 76.04(3) _cell_volume 1931.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 20781 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.168 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20781 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.105 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8732 _reflns_number_gt 3894 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H. (1995). Acta Cryst. A51, 33-38. Nonius B.V (1997-2002). Collect. Data collection software, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307-326. London: Academic press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. ; _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^)+(0.0990P)^2^] 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 8732 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1576 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1896 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 0.55348(11) 0.33009(6) 0.73989(5) 0.0509(3) Uani 1 1 d . . . F1 F -0.2294(3) 0.62885(16) 0.81256(11) 0.0722(6) Uani 1 1 d . . . F2 F -0.2662(4) 0.5705(2) 0.97187(13) 0.1125(10) Uani 1 1 d . . . F3 F -0.0770(5) 0.6090(2) 1.06249(14) 0.1364(13) Uani 1 1 d . . . F4 F 0.1553(4) 0.7072(2) 0.98656(17) 0.1312(12) Uani 1 1 d . . . F5 F 0.1957(3) 0.76481(17) 0.82806(15) 0.0880(8) Uani 1 1 d . . . F6 F -0.0305(2) 0.92075(14) 0.80327(11) 0.0614(5) Uani 1 1 d . . . F7 F 0.0618(2) 1.09350(15) 0.74490(13) 0.0702(6) Uani 1 1 d . . . F8 F 0.1918(2) 1.12676(16) 0.58357(14) 0.0789(7) Uani 1 1 d . . . F9 F 0.2352(2) 0.97466(16) 0.48342(13) 0.0759(6) Uani 1 1 d . . . F10 F 0.1594(2) 0.79524(15) 0.54211(11) 0.0607(5) Uani 1 1 d . . . F11 F -0.2774(2) 0.85609(15) 0.75912(11) 0.0614(5) Uani 1 1 d . . . F12 F -0.5217(2) 0.89416(17) 0.68878(14) 0.0781(6) Uani 1 1 d . . . F13 F -0.5116(2) 0.79799(16) 0.55517(12) 0.0706(6) Uani 1 1 d . . . F14 F -0.2515(2) 0.66142(14) 0.49500(10) 0.0565(5) Uani 1 1 d . . . F15 F -0.0084(2) 0.62357(14) 0.56077(10) 0.0508(5) Uani 1 1 d . . . C1 C 0.6193(5) 0.3189(3) 0.8406(2) 0.0621(10) Uani 1 1 d . . . C2 C 0.6070(5) 0.4270(3) 0.8680(2) 0.0806(13) Uani 1 1 d . . . H2A H 0.6393 0.4182 0.9208 0.121 Uiso 1 1 calc R . . H2B H 0.5004 0.4662 0.8734 0.121 Uiso 1 1 calc R . . H2C H 0.6735 0.4650 0.8271 0.121 Uiso 1 1 calc R . . C3 C 0.5133(5) 0.2651(3) 0.9092(2) 0.0774(12) Uani 1 1 d . . . H3A H 0.5411 0.2663 0.9619 0.116 Uiso 1 1 calc R . . H3B H 0.5252 0.1929 0.8987 0.116 Uiso 1 1 calc R . . H3C H 0.4064 0.3020 0.9105 0.116 Uiso 1 1 calc R . . C4 C 0.7859(5) 0.2554(3) 0.8361(2) 0.0777(13) Uani 1 1 d . . . H4A H 0.8116 0.2440 0.8907 0.117 Uiso 1 1 calc R . . H4B H 0.8564 0.2939 0.7985 0.117 Uiso 1 1 calc R . . H4C H 0.7954 0.1882 0.8162 0.117 Uiso 1 1 calc R . . C5 C 0.5022(4) 0.2037(3) 0.7291(2) 0.0609(10) Uani 1 1 d . . . C6 C 0.3503(5) 0.1923(3) 0.7887(2) 0.0781(12) Uani 1 1 d . . . H6A H 0.3044 0.1435 0.7694 0.117 Uiso 1 1 calc R . . H6B H 0.2790 0.2603 0.7910 0.117 Uiso 1 1 calc R . . H6C H 0.3716 0.1660 0.8434 0.117 Uiso 1 1 calc R . . C7 C 0.6268(5) 0.1069(3) 0.7477(2) 0.0722(12) Uani 1 1 d . . . H7A H 0.5960 0.0441 0.7396 0.108 Uiso 1 1 calc R . . H7B H 0.6390 0.1032 0.8045 0.108 Uiso 1 1 calc R . . H7C H 0.7245 0.1119 0.7108 0.108 Uiso 1 1 calc R . . C8 C 0.4825(5) 0.2016(3) 0.6401(2) 0.0752(12) Uani 1 1 d . . . H8A H 0.4569 0.1357 0.6352 0.113 Uiso 1 1 calc R . . H8B H 0.5785 0.2082 0.6021 0.113 Uiso 1 1 calc R . . H8C H 0.3997 0.2596 0.6269 0.113 Uiso 1 1 calc R . . C9 C 0.7027(4) 0.3644(3) 0.6507(2) 0.0628(10) Uani 1 1 d . . . C10 C 0.7795(5) 0.4490(3) 0.6695(3) 0.0809(13) Uani 1 1 d . . . H10A H 0.8555 0.4658 0.6215 0.121 Uiso 1 1 calc R . . H10B H 0.8303 0.4223 0.7163 0.121 Uiso 1 1 calc R . . H10C H 0.7007 0.5118 0.6826 0.121 Uiso 1 1 calc R . . C11 C 0.6284(5) 0.4121(3) 0.5756(2) 0.0758(12) Uani 1 1 d . . . H11A H 0.7080 0.4281 0.5292 0.114 Uiso 1 1 calc R . . H11B H 0.5526 0.4762 0.5888 0.114 Uiso 1 1 calc R . . H11C H 0.5775 0.3623 0.5613 0.114 Uiso 1 1 calc R . . C12 C 0.8324(5) 0.2702(3) 0.6278(2) 0.0725(11) Uani 1 1 d . . . H12A H 0.9138 0.2932 0.5858 0.109 Uiso 1 1 calc R . . H12B H 0.7920 0.2200 0.6065 0.109 Uiso 1 1 calc R . . H12C H 0.8744 0.2373 0.6764 0.109 Uiso 1 1 calc R . . C13 C 0.3763(4) 0.4353(3) 0.7464(2) 0.0612(10) Uani 1 1 d . . . H13A H 0.3190 0.4256 0.8039 0.073 Uiso 1 1 calc R . . C14 C 0.4047(4) 0.5442(3) 0.7361(2) 0.0676(11) Uani 1 1 d . . . H14A H 0.4921 0.5540 0.7531 0.081 Uiso 1 1 calc R . . C15 C 0.3149(4) 0.6263(3) 0.7046(2) 0.0634(10) Uani 1 1 d . . . H15A H 0.3473 0.6903 0.6972 0.076 Uiso 1 1 calc R . . C16 C 0.1657(4) 0.6287(2) 0.6792(2) 0.0514(9) Uani 1 1 d . . . H16A H 0.1862 0.6362 0.6180 0.062 Uiso 1 1 calc R . . C17 C 0.1245(4) 0.5214(3) 0.7077(2) 0.0585(9) Uani 1 1 d . . . H17A H 0.0791 0.5181 0.7668 0.070 Uiso 1 1 calc R . . H17B H 0.0462 0.5135 0.6781 0.070 Uiso 1 1 calc R . . C18 C 0.2638(4) 0.4318(3) 0.6926(2) 0.0647(11) Uani 1 1 d . . . H18A H 0.3147 0.4374 0.6343 0.078 Uiso 1 1 calc R . . H18B H 0.2307 0.3647 0.7055 0.078 Uiso 1 1 calc R . . C19 C -0.0166(4) 0.7034(3) 0.81030(19) 0.0567(9) Uani 1 1 d . . . C20 C -0.1296(5) 0.6529(3) 0.8522(2) 0.0681(11) Uani 1 1 d . . . C21 C -0.1531(6) 0.6212(3) 0.9361(2) 0.0867(14) Uani 1 1 d . . . C22 C -0.0571(7) 0.6401(3) 0.9801(2) 0.0951(17) Uani 1 1 d . . . C23 C 0.0566(7) 0.6883(3) 0.9430(3) 0.0978(17) Uani 1 1 d . . . C24 C 0.0761(5) 0.7179(3) 0.8606(2) 0.0746(12) Uani 1 1 d . . . C25 C 0.0693(4) 0.8423(2) 0.67762(19) 0.0458(8) Uani 1 1 d . . . C26 C 0.0426(4) 0.9252(3) 0.7240(2) 0.0509(9) Uani 1 1 d . . . C27 C 0.0854(4) 1.0191(3) 0.6943(2) 0.0566(9) Uani 1 1 d . . . C28 C 0.1506(4) 1.0356(3) 0.6130(3) 0.0581(10) Uani 1 1 d . . . C29 C 0.1725(4) 0.9595(3) 0.5630(2) 0.0549(9) Uani 1 1 d . . . C30 C 0.1324(4) 0.8670(2) 0.5970(2) 0.0494(8) Uani 1 1 d . . . C31 C -0.1281(3) 0.7371(2) 0.66588(17) 0.0414(7) Uani 1 1 d . . . C32 C -0.2647(4) 0.8049(3) 0.69324(19) 0.0468(8) Uani 1 1 d . . . C33 C -0.3930(4) 0.8264(3) 0.6576(2) 0.0517(8) Uani 1 1 d . . . C34 C -0.3893(4) 0.7780(3) 0.59050(19) 0.0479(8) Uani 1 1 d . . . C35 C -0.2586(4) 0.7105(2) 0.56048(18) 0.0439(8) Uani 1 1 d . . . C36 C -0.1305(3) 0.6917(2) 0.59773(17) 0.0391(7) Uani 1 1 d . . . B1 B 0.0239(4) 0.7261(3) 0.7091(2) 0.0457(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0687(6) 0.0423(5) 0.0524(5) 0.0126(4) -0.0333(5) -0.0230(4) F1 0.1047(17) 0.0800(14) 0.0461(11) 0.0007(10) -0.0066(11) -0.0587(13) F2 0.207(3) 0.0879(18) 0.0427(12) 0.0010(12) 0.0174(15) -0.075(2) F3 0.280(4) 0.0857(18) 0.0455(14) 0.0112(12) -0.0548(19) -0.032(2) F4 0.218(3) 0.112(2) 0.0996(19) 0.0020(16) -0.116(2) -0.033(2) F5 0.1102(18) 0.0739(15) 0.1058(18) 0.0130(13) -0.0762(16) -0.0323(14) F6 0.0804(14) 0.0579(12) 0.0560(12) 0.0012(9) -0.0223(11) -0.0298(11) F7 0.0765(14) 0.0543(12) 0.0910(15) -0.0020(11) -0.0295(12) -0.0262(11) F8 0.0730(14) 0.0552(13) 0.1081(17) 0.0208(12) -0.0181(13) -0.0302(11) F9 0.0756(14) 0.0662(14) 0.0719(15) 0.0227(11) 0.0008(12) -0.0203(12) F10 0.0672(13) 0.0595(12) 0.0536(11) 0.0089(9) -0.0097(10) -0.0211(10) F11 0.0579(12) 0.0713(13) 0.0603(12) -0.0250(10) -0.0052(10) -0.0186(10) F12 0.0446(12) 0.0868(16) 0.1027(17) -0.0317(13) -0.0099(11) -0.0046(12) F13 0.0502(12) 0.0899(15) 0.0787(14) -0.0015(11) -0.0334(11) -0.0137(11) F14 0.0664(12) 0.0690(13) 0.0425(10) -0.0059(9) -0.0218(9) -0.0203(10) F15 0.0518(11) 0.0550(11) 0.0464(10) -0.0041(9) -0.0127(9) -0.0105(10) C1 0.094(3) 0.050(2) 0.055(2) 0.0030(16) -0.044(2) -0.017(2) C2 0.121(4) 0.056(2) 0.085(3) -0.001(2) -0.065(3) -0.020(2) C3 0.129(4) 0.059(2) 0.049(2) 0.0118(18) -0.034(2) -0.024(2) C4 0.105(3) 0.064(2) 0.077(3) 0.000(2) -0.063(3) -0.005(2) C5 0.084(3) 0.049(2) 0.065(2) 0.0118(17) -0.037(2) -0.033(2) C6 0.097(3) 0.065(3) 0.085(3) 0.019(2) -0.034(3) -0.043(2) C7 0.111(3) 0.042(2) 0.072(3) 0.0042(18) -0.043(2) -0.017(2) C8 0.110(3) 0.064(2) 0.071(2) -0.0031(19) -0.049(2) -0.030(2) C9 0.072(2) 0.059(2) 0.065(2) 0.0233(18) -0.034(2) -0.027(2) C10 0.078(3) 0.072(3) 0.104(3) 0.023(2) -0.036(2) -0.039(2) C11 0.082(3) 0.081(3) 0.066(2) 0.034(2) -0.034(2) -0.028(2) C12 0.074(3) 0.071(3) 0.073(3) 0.015(2) -0.027(2) -0.018(2) C13 0.073(3) 0.049(2) 0.073(2) 0.0107(17) -0.038(2) -0.0257(19) C14 0.070(2) 0.048(2) 0.100(3) 0.0130(19) -0.052(2) -0.0229(19) C15 0.058(2) 0.052(2) 0.090(3) 0.0196(19) -0.038(2) -0.0257(18) C16 0.054(2) 0.047(2) 0.057(2) 0.0146(15) -0.0246(17) -0.0178(17) C17 0.056(2) 0.054(2) 0.070(2) 0.0120(17) -0.0253(19) -0.0206(18) C18 0.065(2) 0.050(2) 0.091(3) 0.0103(19) -0.038(2) -0.0241(19) C19 0.088(3) 0.048(2) 0.0427(19) 0.0093(16) -0.0257(19) -0.026(2) C20 0.125(4) 0.052(2) 0.0380(19) 0.0045(16) -0.021(2) -0.039(2) C21 0.168(5) 0.060(3) 0.040(2) 0.0026(19) -0.014(3) -0.049(3) C22 0.196(6) 0.062(3) 0.035(2) 0.0122(19) -0.039(3) -0.038(3) C23 0.185(5) 0.065(3) 0.068(3) 0.004(2) -0.078(3) -0.032(3) C24 0.117(4) 0.060(2) 0.066(2) 0.0140(19) -0.056(3) -0.035(2) C25 0.0465(19) 0.0454(19) 0.052(2) 0.0080(15) -0.0230(16) -0.0168(15) C26 0.050(2) 0.053(2) 0.054(2) 0.0103(17) -0.0233(18) -0.0192(17) C27 0.052(2) 0.045(2) 0.081(3) 0.0042(19) -0.029(2) -0.0176(17) C28 0.043(2) 0.045(2) 0.085(3) 0.023(2) -0.0198(19) -0.0193(17) C29 0.046(2) 0.052(2) 0.061(2) 0.0186(18) -0.0117(18) -0.0129(17) C30 0.0419(18) 0.047(2) 0.061(2) 0.0077(17) -0.0192(17) -0.0112(16) C31 0.0442(19) 0.0468(19) 0.0373(17) 0.0071(14) -0.0105(15) -0.0220(16) C32 0.048(2) 0.053(2) 0.0458(18) -0.0078(15) -0.0086(16) -0.0216(17) C33 0.040(2) 0.050(2) 0.062(2) -0.0090(17) -0.0025(17) -0.0089(16) C34 0.043(2) 0.056(2) 0.0502(19) 0.0066(16) -0.0228(16) -0.0146(17) C35 0.052(2) 0.0474(19) 0.0372(17) 0.0073(14) -0.0166(16) -0.0209(17) C36 0.0405(18) 0.0412(18) 0.0342(16) 0.0046(14) -0.0093(14) -0.0095(15) B1 0.052(2) 0.049(2) 0.043(2) 0.0098(17) -0.0194(18) -0.0213(19) _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 C13 1.863(4) . ? P1 C9 1.876(4) . ? P1 C5 1.895(3) . ? P1 C1 1.895(3) . ? F1 C20 1.363(4) . ? F2 C21 1.352(5) . ? F3 C22 1.372(4) . ? F4 C23 1.369(5) . ? F5 C24 1.360(5) . ? F6 C26 1.354(4) . ? F7 C27 1.350(4) . ? F8 C28 1.349(4) . ? F9 C29 1.343(4) . ? F10 C30 1.369(4) . ? F11 C32 1.356(3) . ? F12 C33 1.353(4) . ? F13 C34 1.334(3) . ? F14 C35 1.345(3) . ? F15 C36 1.353(3) . ? C1 C3 1.543(6) . ? C1 C4 1.545(5) . ? C1 C2 1.547(5) . ? C5 C7 1.545(5) . ? C5 C6 1.550(6) . ? C5 C8 1.553(5) . ? C9 C12 1.534(5) . ? C9 C11 1.549(4) . ? C9 C10 1.564(5) . ? C13 C14 1.512(4) . ? C13 C18 1.527(4) . ? C14 C15 1.318(4) . ? C15 C16 1.510(4) . ? C16 C17 1.546(4) . ? C16 B1 1.647(5) . ? C17 C18 1.525(5) . ? C19 C20 1.375(5) . ? C19 C24 1.385(5) . ? C19 B1 1.661(5) . ? C20 C21 1.396(5) . ? C21 C22 1.355(6) . ? C22 C23 1.341(7) . ? C23 C24 1.370(6) . ? C25 C30 1.378(5) . ? C25 C26 1.390(5) . ? C25 B1 1.677(5) . ? C26 C27 1.389(5) . ? C27 C28 1.375(5) . ? C28 C29 1.363(5) . ? C29 C30 1.376(5) . ? C31 C36 1.381(4) . ? C31 C32 1.383(4) . ? C31 B1 1.673(4) . ? C32 C33 1.385(4) . ? C33 C34 1.372(4) . ? C34 C35 1.358(4) . ? C35 C36 1.402(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 C13 P1 C9 109.92(17) . . ? C13 P1 C5 108.64(16) . . ? C9 P1 C5 111.03(18) . . ? C13 P1 C1 106.06(17) . . ? C9 P1 C1 111.72(17) . . ? C5 P1 C1 109.32(15) . . ? C3 C1 C4 108.5(3) . . ? C3 C1 C2 105.4(3) . . ? C4 C1 C2 109.2(3) . . ? C3 C1 P1 110.0(2) . . ? C4 C1 P1 111.8(3) . . ? C2 C1 P1 111.7(2) . . ? C7 C5 C6 107.6(3) . . ? C7 C5 C8 106.8(3) . . ? C6 C5 C8 109.0(3) . . ? C7 C5 P1 112.9(2) . . ? C6 C5 P1 110.1(3) . . ? C8 C5 P1 110.3(2) . . ? C12 C9 C11 109.7(3) . . ? C12 C9 C10 106.8(3) . . ? C11 C9 C10 105.9(3) . . ? C12 C9 P1 112.3(2) . . ? C11 C9 P1 110.4(3) . . ? C10 C9 P1 111.5(3) . . ? C14 C13 C18 108.9(3) . . ? C14 C13 P1 114.5(2) . . ? C18 C13 P1 116.8(3) . . ? C15 C14 C13 123.7(3) . . ? C14 C15 C16 126.4(3) . . ? C15 C16 C17 107.9(2) . . ? C15 C16 B1 115.0(3) . . ? C17 C16 B1 112.8(3) . . ? C18 C17 C16 112.3(3) . . ? C17 C18 C13 109.5(3) . . ? C20 C19 C24 112.1(3) . . ? C20 C19 B1 124.0(3) . . ? C24 C19 B1 123.0(3) . . ? F1 C20 C19 120.7(3) . . ? F1 C20 C21 114.2(4) . . ? C19 C20 C21 125.1(4) . . ? F2 C21 C22 120.9(4) . . ? F2 C21 C20 120.9(4) . . ? C22 C21 C20 118.2(4) . . ? C23 C22 C21 119.9(4) . . ? C23 C22 F3 120.7(4) . . ? C21 C22 F3 119.4(5) . . ? C22 C23 F4 120.6(4) . . ? C22 C23 C24 120.0(4) . . ? F4 C23 C24 119.3(5) . . ? F5 C24 C23 115.9(4) . . ? F5 C24 C19 119.5(3) . . ? C23 C24 C19 124.6(4) . . ? C30 C25 C26 112.0(3) . . ? C30 C25 B1 120.8(3) . . ? C26 C25 B1 127.0(3) . . ? F6 C26 C27 114.2(3) . . ? F6 C26 C25 121.8(3) . . ? C27 C26 C25 124.0(3) . . ? F7 C27 C28 120.6(3) . . ? F7 C27 C26 120.0(3) . . ? C28 C27 C26 119.5(3) . . ? F8 C28 C29 120.7(4) . . ? F8 C28 C27 119.8(4) . . ? C29 C28 C27 119.5(3) . . ? F9 C29 C28 120.2(3) . . ? F9 C29 C30 121.7(3) . . ? C28 C29 C30 118.2(3) . . ? F10 C30 C29 113.9(3) . . ? F10 C30 C25 119.4(3) . . ? C29 C30 C25 126.7(3) . . ? C36 C31 C32 113.1(2) . . ? C36 C31 B1 126.5(3) . . ? C32 C31 B1 120.0(3) . . ? F11 C32 C31 119.4(2) . . ? F11 C32 C33 115.9(3) . . ? C31 C32 C33 124.7(3) . . ? F12 C33 C34 120.0(3) . . ? F12 C33 C32 120.5(3) . . ? C34 C33 C32 119.5(3) . . ? F13 C34 C35 120.9(3) . . ? F13 C34 C33 120.4(3) . . ? C35 C34 C33 118.7(3) . . ? F14 C35 C34 120.2(2) . . ? F14 C35 C36 119.8(3) . . ? C34 C35 C36 120.0(3) . . ? F15 C36 C31 122.8(2) . . ? F15 C36 C35 113.4(3) . . ? C31 C36 C35 123.9(3) . . ? C16 B1 C19 104.9(2) . . ? C16 B1 C31 112.9(3) . . ? C19 B1 C31 112.8(3) . . ? C16 B1 C25 112.5(3) . . ? C19 B1 C25 112.7(3) . . ? C31 B1 C25 101.4(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.363 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.061 _vrf_PLAT601_k0867 ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 283.00 A**3 RESPONSE: During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecules (solvents present are bromobenzene/hexane). Attempts made to model the solvent molecule were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 283.0 \%A^3^ containing approximately 54 electrons. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered solvent molecules were carried out by St\"ahler et al. (2001), Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005). References: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13 Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005). Acta Cryst. E61, m2014-m2017. Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M. (2003). Acta Cryst. E59, o975-o977. Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M. (2003). Acta Cryst. C59, m84-m86. St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst. C57, 26-27. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material #loop_ # _platon_squeeze_void_nr # _platon_squeeze_void_average_x # _platon_squeeze_void_average_y # _platon_squeeze_void_average_z # _platon_squeeze_void_volume # _platon_squeeze_void_count_electrons # _platon_squeeze_void_content # 1 -0.016 0.000 0.000 285 54 . #===end