# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _publ_contact_author_name 'Stephan, Douglas W.' _publ_contact_author_email dstephan@chem.utoronto.ca _publ_section_title ; The Synthesis and Exchange Chemistry of Frustrated Lewis Pair-Nitrous Oxide Complexes ; loop_ _publ_author_name R.Neu E.Otten A.Lough D.W.Stephan data_C57H60BF20N2O2PZr_compound13 _database_code_depnum_ccdc_archive 'CCDC 768908' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C57 H60 B F20 N2 O2 P Zr' _chemical_formula_weight 1318.07 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 '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 36.218(7) _cell_length_b 12.304(3) _cell_length_c 31.224(10) _cell_angle_alpha 90.00 _cell_angle_beta 122.397(5) _cell_angle_gamma 90.00 _cell_volume 11749(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6058 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 20.79 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5376 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6761 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13566 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1013 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.61 _reflns_number_total 13566 _reflns_number_gt 7588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13566 _refine_ls_number_parameters 760 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.015 _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 Zr1 Zr 0.618036(11) -0.06781(3) 0.691417(13) 0.02444(10) Uani 1 1 d . . . P1 P 0.66969(3) 0.27463(9) 0.82902(4) 0.0381(3) Uani 1 1 d D . . O1 O 0.63387(8) 0.0971(2) 0.71809(10) 0.0333(6) Uani 1 1 d . A . O2 O 0.63440(8) -0.1309(2) 0.75534(9) 0.0334(6) Uani 1 1 d . . . N1 N 0.64915(10) 0.2270(3) 0.76991(12) 0.0364(8) Uani 1 1 d . A . N2 N 0.64968(10) 0.1250(3) 0.76497(12) 0.0363(8) Uani 1 1 d . . . C1 C 0.54345(11) -0.0922(3) 0.67996(14) 0.0339(10) Uani 1 1 d . . . C2 C 0.54518(11) 0.0166(3) 0.66838(14) 0.0310(9) Uani 1 1 d . . . C3 C 0.54651(11) 0.0199(3) 0.62389(14) 0.0309(9) Uani 1 1 d . . . C4 C 0.54445(11) -0.0879(3) 0.60741(14) 0.0323(9) Uani 1 1 d . . . C5 C 0.54440(11) -0.1583(3) 0.64363(15) 0.0339(9) Uani 1 1 d . . . C6 C 0.53944(13) -0.1334(4) 0.72245(16) 0.0544(13) Uani 1 1 d . . . H6A H 0.5087 -0.1320 0.7120 0.082 Uiso 1 1 calc R . . H6B H 0.5566 -0.0870 0.7523 0.082 Uiso 1 1 calc R . . H6C H 0.5505 -0.2081 0.7308 0.082 Uiso 1 1 calc R . . C7 C 0.54246(13) 0.1132(4) 0.69568(16) 0.0494(12) Uani 1 1 d . . . H7A H 0.5117 0.1332 0.6808 0.074 Uiso 1 1 calc R . . H7B H 0.5582 0.1743 0.6926 0.074 Uiso 1 1 calc R . . H7C H 0.5556 0.0952 0.7316 0.074 Uiso 1 1 calc R . . C8 C 0.54478(14) 0.1220(3) 0.59674(17) 0.0495(12) Uani 1 1 d . . . H8A H 0.5156 0.1543 0.5809 0.074 Uiso 1 1 calc R . . H8B H 0.5510 0.1049 0.5706 0.074 Uiso 1 1 calc R . . H8C H 0.5666 0.1736 0.6210 0.074 Uiso 1 1 calc R . . C9 C 0.53339(13) -0.1218(4) 0.55564(15) 0.0458(11) Uani 1 1 d . . . H9A H 0.5015 -0.1237 0.5324 0.069 Uiso 1 1 calc R . . H9B H 0.5454 -0.1943 0.5576 0.069 Uiso 1 1 calc R . . H9C H 0.5460 -0.0697 0.5432 0.069 Uiso 1 1 calc R . . C10 C 0.53948(14) -0.2800(4) 0.64009(19) 0.0555(13) Uani 1 1 d . . . H10A H 0.5120 -0.3003 0.6371 0.083 Uiso 1 1 calc R . . H10B H 0.5641 -0.3133 0.6707 0.083 Uiso 1 1 calc R . . H10C H 0.5392 -0.3059 0.6102 0.083 Uiso 1 1 calc R . . C11 C 0.67777(12) -0.1917(3) 0.70185(15) 0.0321(9) Uani 1 1 d . . . C12 C 0.64846(11) -0.1807(3) 0.64890(14) 0.0288(8) Uani 1 1 d . . . C13 C 0.65068(11) -0.0717(3) 0.63559(14) 0.0282(8) Uani 1 1 d . . . C14 C 0.68057(12) -0.0151(3) 0.68003(15) 0.0322(9) Uani 1 1 d . . . C15 C 0.69747(11) -0.0890(3) 0.72116(14) 0.0345(10) Uani 1 1 d . . . C16 C 0.68732(14) -0.2967(4) 0.73021(17) 0.0497(12) Uani 1 1 d . . . H16A H 0.7017 -0.3468 0.7192 0.075 Uiso 1 1 calc R . . H16B H 0.6599 -0.3290 0.7233 0.075 Uiso 1 1 calc R . . H16C H 0.7066 -0.2830 0.7667 0.075 Uiso 1 1 calc R . . C17 C 0.62784(13) -0.2771(3) 0.61402(15) 0.0379(10) Uani 1 1 d . . . H17A H 0.6508 -0.3266 0.6184 0.057 Uiso 1 1 calc R . . H17B H 0.6107 -0.2519 0.5788 0.057 Uiso 1 1 calc R . . H17C H 0.6086 -0.3152 0.6222 0.057 Uiso 1 1 calc R . . C18 C 0.63198(13) -0.0267(3) 0.58348(15) 0.0389(10) Uani 1 1 d . . . H18A H 0.6557 -0.0115 0.5780 0.058 Uiso 1 1 calc R . . H18B H 0.6162 0.0408 0.5800 0.058 Uiso 1 1 calc R . . H18C H 0.6118 -0.0796 0.5584 0.058 Uiso 1 1 calc R . . C19 C 0.69403(14) 0.1013(3) 0.68212(17) 0.0477(12) Uani 1 1 d . . . H19A H 0.7128 0.1070 0.6685 0.072 Uiso 1 1 calc R . . H19B H 0.7101 0.1265 0.7174 0.072 Uiso 1 1 calc R . . H19C H 0.6679 0.1464 0.6619 0.072 Uiso 1 1 calc R . . C20 C 0.73180(13) -0.0622(4) 0.77533(16) 0.0505(12) Uani 1 1 d . . . H20A H 0.7584 -0.0370 0.7773 0.076 Uiso 1 1 calc R . . H20B H 0.7385 -0.1273 0.7964 0.076 Uiso 1 1 calc R . . H20C H 0.7209 -0.0049 0.7876 0.076 Uiso 1 1 calc R . . C21 C 0.65265(14) -0.1840(4) 0.80195(16) 0.0513(12) Uani 1 1 d . . . H21A H 0.6443 -0.1460 0.8231 0.077 Uiso 1 1 calc R . . H21B H 0.6846 -0.1844 0.8191 0.077 Uiso 1 1 calc R . . H21C H 0.6419 -0.2590 0.7963 0.077 Uiso 1 1 calc R . . C22 C 0.62753(16) 0.3810(4) 0.8158(2) 0.056(2) Uiso 0.653(4) 1 d PD A 1 C23 C 0.6439(3) 0.4757(6) 0.8545(3) 0.067(2) Uiso 0.653(4) 1 d PD A 1 H23A H 0.6199 0.5271 0.8444 0.101 Uiso 0.653(4) 1 calc PR A 1 H23B H 0.6681 0.5131 0.8551 0.101 Uiso 0.653(4) 1 calc PR A 1 H23C H 0.6540 0.4469 0.8883 0.101 Uiso 0.653(4) 1 calc PR A 1 C25 C 0.61331(17) 0.4392(4) 0.76595(19) 0.0717(16) Uani 1 1 d D A 1 H25A H 0.5914 0.4947 0.7593 0.108 Uiso 0.653(4) 1 calc PR A 1 H25B H 0.6006 0.3864 0.7381 0.108 Uiso 0.653(4) 1 calc PR A 1 H25C H 0.6388 0.4739 0.7685 0.108 Uiso 0.653(4) 1 calc PR A 1 C27 C 0.5850(2) 0.3348(7) 0.8091(3) 0.067(2) Uiso 0.653(4) 1 d PD A 1 H27A H 0.5646 0.3944 0.8021 0.101 Uiso 0.653(4) 1 calc PR A 1 H27B H 0.5919 0.2973 0.8402 0.101 Uiso 0.653(4) 1 calc PR A 1 H27C H 0.5717 0.2834 0.7807 0.101 Uiso 0.653(4) 1 calc PR A 1 C26 C 0.67260(15) 0.1744(4) 0.87501(16) 0.0442(17) Uiso 0.653(4) 1 d PD A 1 C28 C 0.63511(16) 0.0924(4) 0.85180(19) 0.0717(17) Uani 1 1 d D A 1 H28A H 0.6387 0.0422 0.8781 0.108 Uiso 0.653(4) 1 calc PR A 1 H28B H 0.6353 0.0514 0.8250 0.108 Uiso 0.653(4) 1 calc PR A 1 H28C H 0.6072 0.1310 0.8373 0.108 Uiso 0.653(4) 1 calc PR A 1 C29 C 0.67451(18) 0.2294(4) 0.91992(17) 0.0710(16) Uani 1 1 d D A 1 H29A H 0.6760 0.1739 0.9433 0.107 Uiso 0.653(4) 1 calc PR A 1 H29B H 0.6482 0.2738 0.9077 0.107 Uiso 0.653(4) 1 calc PR A 1 H29C H 0.7005 0.2758 0.9376 0.107 Uiso 0.653(4) 1 calc PR A 1 C31 C 0.7120(2) 0.1024(6) 0.8897(3) 0.063(2) Uiso 0.653(4) 1 d PD A 1 H31A H 0.7151 0.0476 0.9142 0.095 Uiso 0.653(4) 1 calc PR A 1 H31B H 0.7385 0.1472 0.9050 0.095 Uiso 0.653(4) 1 calc PR A 1 H31C H 0.7077 0.0663 0.8594 0.095 Uiso 0.653(4) 1 calc PR A 1 C30 C 0.72148(14) 0.3402(4) 0.84390(19) 0.0410(16) Uiso 0.653(4) 1 d PD A 1 C24 C 0.7145(2) 0.4370(5) 0.8093(3) 0.0512(19) Uiso 0.653(4) 1 d PD A 1 H24A H 0.7429 0.4681 0.8190 0.077 Uiso 0.653(4) 1 calc PR A 1 H24B H 0.6968 0.4924 0.8128 0.077 Uiso 0.653(4) 1 calc PR A 1 H24C H 0.6993 0.4124 0.7740 0.077 Uiso 0.653(4) 1 calc PR A 1 C32 C 0.7498(2) 0.3766(7) 0.8997(2) 0.066(2) Uiso 0.653(4) 1 d PD A 1 H32A H 0.7768 0.4102 0.9058 0.098 Uiso 0.653(4) 1 calc PR A 1 H32B H 0.7571 0.3133 0.9219 0.098 Uiso 0.653(4) 1 calc PR A 1 H32C H 0.7335 0.4294 0.9068 0.098 Uiso 0.653(4) 1 calc PR A 1 C33 C 0.7462(3) 0.2578(7) 0.8312(4) 0.050(3) Uiso 0.653(4) 1 d PD A 1 H33A H 0.7739 0.2898 0.8389 0.075 Uiso 0.653(4) 1 calc PR A 1 H33B H 0.7284 0.2394 0.7951 0.075 Uiso 0.653(4) 1 calc PR A 1 H33C H 0.7521 0.1919 0.8515 0.075 Uiso 0.653(4) 1 calc PR A 1 C22A C 0.6589(2) 0.4226(4) 0.8159(3) 0.058(4) Uiso 0.347(4) 1 d PD A 2 C23A C 0.6702(4) 0.4752(9) 0.8667(4) 0.039(3) Uiso 0.347(4) 1 d PD A 2 H23D H 0.6652 0.5537 0.8620 0.058 Uiso 0.347(4) 1 calc PR A 2 H23E H 0.7010 0.4612 0.8927 0.058 Uiso 0.347(4) 1 calc PR A 2 H23F H 0.6516 0.4437 0.8775 0.058 Uiso 0.347(4) 1 calc PR A 2 C25A C 0.61331(17) 0.4392(4) 0.76595(19) 0.0717(16) Uani 0.00 1 d PD A 2 H25D H 0.6081 0.5170 0.7583 0.108 Uiso 0.347(4) 1 calc PR A 2 H25E H 0.5904 0.4094 0.7703 0.108 Uiso 0.347(4) 1 calc PR A 2 H25F H 0.6128 0.4017 0.7379 0.108 Uiso 0.347(4) 1 calc PR A 2 C27A C 0.6957(3) 0.4611(10) 0.8082(5) 0.037(3) Uiso 0.347(4) 1 d PD A 2 H27D H 0.6925 0.5392 0.8008 0.055 Uiso 0.347(4) 1 calc PR A 2 H27E H 0.6936 0.4215 0.7797 0.055 Uiso 0.347(4) 1 calc PR A 2 H27F H 0.7242 0.4471 0.8391 0.055 Uiso 0.347(4) 1 calc PR A 2 C26A C 0.6451(2) 0.2122(5) 0.86264(19) 0.041(3) Uiso 0.347(4) 1 d PD A 2 C28A C 0.63511(16) 0.0924(4) 0.85180(19) 0.0717(17) Uani 0.00 1 d PD A 2 H28D H 0.6220 0.0654 0.8702 0.108 Uiso 0.347(4) 1 calc PR A 2 H28E H 0.6622 0.0527 0.8629 0.108 Uiso 0.347(4) 1 calc PR A 2 H28F H 0.6147 0.0817 0.8153 0.108 Uiso 0.347(4) 1 calc PR A 2 C29A C 0.67451(18) 0.2294(4) 0.91992(17) 0.0710(16) Uani 0.00 1 d PD A 2 H29D H 0.6609 0.1965 0.9367 0.107 Uiso 0.347(4) 1 calc PR A 2 H29E H 0.6786 0.3074 0.9273 0.107 Uiso 0.347(4) 1 calc PR A 2 H29F H 0.7030 0.1952 0.9325 0.107 Uiso 0.347(4) 1 calc PR A 2 C31A C 0.5973(3) 0.2477(11) 0.8338(5) 0.051(4) Uiso 0.347(4) 1 d PD A 2 H31D H 0.5830 0.2173 0.8504 0.077 Uiso 0.347(4) 1 calc PR A 2 H31E H 0.5824 0.2215 0.7988 0.077 Uiso 0.347(4) 1 calc PR A 2 H31F H 0.5957 0.3273 0.8339 0.077 Uiso 0.347(4) 1 calc PR A 2 C30A C 0.72880(18) 0.2316(7) 0.8684(3) 0.055(4) Uiso 0.347(4) 1 d PD A 2 C24A C 0.7386(4) 0.1120(8) 0.8861(5) 0.051(4) Uiso 0.347(4) 1 d PD A 2 H24D H 0.7703 0.1003 0.9061 0.076 Uiso 0.347(4) 1 calc PR A 2 H24E H 0.7252 0.0639 0.8565 0.076 Uiso 0.347(4) 1 calc PR A 2 H24F H 0.7266 0.0958 0.9071 0.076 Uiso 0.347(4) 1 calc PR A 2 C32A C 0.7587(4) 0.3015(10) 0.9158(4) 0.043(3) Uiso 0.347(4) 1 d PD A 2 H32D H 0.7886 0.2729 0.9333 0.065 Uiso 0.347(4) 1 calc PR A 2 H32E H 0.7480 0.2992 0.9387 0.065 Uiso 0.347(4) 1 calc PR A 2 H32F H 0.7586 0.3768 0.9054 0.065 Uiso 0.347(4) 1 calc PR A 2 C33A C 0.7523(6) 0.2315(14) 0.8392(6) 0.041(4) Uiso 0.347(4) 1 d PD A 2 H33D H 0.7828 0.2094 0.8621 0.061 Uiso 0.347(4) 1 calc PR A 2 H33E H 0.7513 0.3046 0.8263 0.061 Uiso 0.347(4) 1 calc PR A 2 H33F H 0.7376 0.1803 0.8108 0.061 Uiso 0.347(4) 1 calc PR A 2 F1 F 0.82107(7) -0.07662(19) 0.88420(8) 0.0430(6) Uani 1 1 d . . . F2 F 0.85038(8) -0.0555(2) 0.82345(9) 0.0589(7) Uani 1 1 d . . . F3 F 0.93735(9) -0.0670(2) 0.85966(10) 0.0598(7) Uani 1 1 d . . . F4 F 0.99505(7) -0.1025(2) 0.96041(9) 0.0494(6) Uani 1 1 d . . . F5 F 0.96657(6) -0.12234(17) 1.02247(8) 0.0337(5) Uani 1 1 d . . . F6 F 0.83781(9) 0.09308(18) 0.95618(10) 0.0553(7) Uani 1 1 d . . . F7 F 0.86420(12) 0.2903(2) 0.99587(12) 0.0880(11) Uani 1 1 d . . . F8 F 0.93748(12) 0.3153(2) 1.08993(14) 0.1003(12) Uani 1 1 d . . . F9 F 0.98355(9) 0.1372(2) 1.14321(12) 0.0803(10) Uani 1 1 d . . . F10 F 0.95825(7) -0.0582(2) 1.10495(9) 0.0494(6) Uani 1 1 d . . . F11 F 0.81419(7) 0.00335(19) 1.02086(8) 0.0411(6) Uani 1 1 d . . . F12 F 0.73422(7) -0.0612(2) 0.98881(10) 0.0625(8) Uani 1 1 d . . . F13 F 0.69763(7) -0.2327(2) 0.92403(10) 0.0653(8) Uani 1 1 d . . . F14 F 0.74556(8) -0.3408(2) 0.89405(10) 0.0596(7) Uani 1 1 d . . . F15 F 0.82737(7) -0.28176(18) 0.92830(9) 0.0442(6) Uani 1 1 d . . . F16 F 0.88144(7) -0.14291(18) 1.09230(8) 0.0381(5) Uani 1 1 d . . . F17 F 0.91054(8) -0.3144(2) 1.15369(9) 0.0529(7) Uani 1 1 d . . . F18 F 0.94317(7) -0.48958(18) 1.13249(9) 0.0452(6) Uani 1 1 d . . . F19 F 0.94581(7) -0.48900(17) 1.04674(9) 0.0426(6) Uani 1 1 d . . . F20 F 0.91979(7) -0.31855(16) 0.98711(8) 0.0332(5) Uani 1 1 d . . . C67 C 0.89201(12) -0.1043(3) 0.95697(14) 0.0279(8) Uani 1 1 d . . . C68 C 0.86465(13) -0.0851(3) 0.90586(15) 0.0345(9) Uani 1 1 d . . . C69 C 0.87931(13) -0.0733(3) 0.87326(15) 0.0392(10) Uani 1 1 d . . . C70 C 0.92320(15) -0.0785(3) 0.89131(17) 0.0418(10) Uani 1 1 d . . . C71 C 0.95207(13) -0.0953(3) 0.94194(16) 0.0370(10) Uani 1 1 d . . . C72 C 0.93633(12) -0.1071(3) 0.97300(14) 0.0295(9) Uani 1 1 d . . . C73 C 0.89575(13) 0.0055(3) 1.02858(15) 0.0313(9) Uani 1 1 d . . . C74 C 0.87479(16) 0.1000(3) 1.00338(18) 0.0456(11) Uani 1 1 d . . . C75 C 0.8874(2) 0.2037(4) 1.0224(2) 0.0583(14) Uani 1 1 d . . . C76 C 0.9247(2) 0.2155(4) 1.0701(2) 0.0611(15) Uani 1 1 d . . . C77 C 0.94720(15) 0.1272(4) 1.0960(2) 0.0519(13) Uani 1 1 d . . . C78 C 0.93312(13) 0.0245(3) 1.07548(17) 0.0369(10) Uani 1 1 d . . . C79 C 0.82567(11) -0.1345(3) 0.97551(14) 0.0287(8) Uani 1 1 d . . . C80 C 0.79947(12) -0.0836(3) 0.98944(14) 0.0317(9) Uani 1 1 d . . . C81 C 0.75712(12) -0.1151(4) 0.97280(16) 0.0408(11) Uani 1 1 d . . . C82 C 0.73865(13) -0.2006(4) 0.94073(16) 0.0449(11) Uani 1 1 d . . . C83 C 0.76318(13) -0.2552(3) 0.92583(16) 0.0424(11) Uani 1 1 d . . . C84 C 0.80509(12) -0.2216(3) 0.94344(15) 0.0332(9) Uani 1 1 d . . . C85 C 0.90021(10) -0.2187(3) 1.03727(13) 0.0230(8) Uani 1 1 d . . . C86 C 0.89846(11) -0.2258(3) 1.08013(14) 0.0286(9) Uani 1 1 d . . . C87 C 0.91284(12) -0.3135(3) 1.11215(14) 0.0327(9) Uani 1 1 d . . . C88 C 0.92949(12) -0.4030(3) 1.10170(15) 0.0332(9) Uani 1 1 d . . . C89 C 0.93084(11) -0.4018(3) 1.05886(15) 0.0304(9) Uani 1 1 d . . . C90 C 0.91681(11) -0.3118(3) 1.02822(14) 0.0260(8) Uani 1 1 d . . . B1 B 0.87853(13) -0.1127(3) 0.99917(16) 0.0258(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 Zr1 0.02439(17) 0.02747(19) 0.02073(19) 0.00036(17) 0.01161(15) -0.00043(16) P1 0.0463(6) 0.0441(7) 0.0335(6) -0.0143(5) 0.0278(5) -0.0160(5) O1 0.0367(14) 0.0352(16) 0.0284(16) -0.0105(12) 0.0177(13) -0.0052(12) O2 0.0299(13) 0.0465(17) 0.0208(14) 0.0071(13) 0.0117(12) 0.0022(12) N2 0.0373(18) 0.036(2) 0.033(2) -0.0060(16) 0.0178(16) -0.0035(16) N1 0.050(2) 0.036(2) 0.036(2) -0.0127(16) 0.0317(17) -0.0110(16) C1 0.0187(17) 0.054(3) 0.025(2) 0.006(2) 0.0088(16) 0.0026(17) C2 0.0201(18) 0.040(2) 0.025(2) -0.0040(18) 0.0066(16) 0.0050(17) C3 0.0270(19) 0.037(2) 0.023(2) 0.0035(18) 0.0091(17) 0.0026(17) C4 0.0264(19) 0.043(3) 0.022(2) -0.0045(18) 0.0096(17) -0.0025(17) C5 0.0272(19) 0.037(2) 0.031(2) -0.0012(19) 0.0110(18) -0.0054(17) C6 0.038(2) 0.091(4) 0.043(3) 0.014(3) 0.027(2) 0.000(2) C7 0.031(2) 0.060(3) 0.044(3) -0.016(2) 0.012(2) 0.010(2) C8 0.050(3) 0.043(3) 0.046(3) 0.018(2) 0.019(2) 0.009(2) C9 0.036(2) 0.068(3) 0.029(2) -0.009(2) 0.014(2) -0.001(2) C10 0.043(3) 0.046(3) 0.066(3) -0.005(3) 0.022(2) -0.016(2) C11 0.035(2) 0.034(2) 0.032(2) 0.0095(19) 0.0220(19) 0.0107(18) C12 0.0283(19) 0.030(2) 0.030(2) -0.0006(17) 0.0168(18) 0.0031(16) C13 0.0332(19) 0.030(2) 0.025(2) 0.0024(18) 0.0185(17) 0.0007(18) C14 0.034(2) 0.039(2) 0.033(2) -0.0039(19) 0.0236(19) -0.0067(18) C15 0.0241(18) 0.051(3) 0.028(2) -0.005(2) 0.0132(17) -0.0020(18) C16 0.055(3) 0.050(3) 0.050(3) 0.018(2) 0.032(2) 0.023(2) C17 0.047(2) 0.029(2) 0.042(3) -0.005(2) 0.028(2) 0.0019(19) C18 0.049(2) 0.042(2) 0.032(2) 0.000(2) 0.025(2) 0.000(2) C19 0.053(3) 0.049(3) 0.053(3) -0.010(2) 0.036(2) -0.021(2) C20 0.034(2) 0.078(3) 0.038(3) -0.005(2) 0.018(2) -0.006(2) C21 0.052(3) 0.070(3) 0.037(3) 0.021(2) 0.027(2) 0.021(2) C25 0.084(4) 0.060(3) 0.072(4) -0.013(3) 0.041(3) 0.018(3) C28 0.080(4) 0.090(4) 0.065(4) -0.002(3) 0.052(3) -0.035(3) C29 0.106(4) 0.079(4) 0.039(3) -0.001(3) 0.046(3) -0.003(3) C25A 0.084(4) 0.060(3) 0.072(4) -0.013(3) 0.041(3) 0.018(3) C28A 0.080(4) 0.090(4) 0.065(4) -0.002(3) 0.052(3) -0.035(3) C29A 0.106(4) 0.079(4) 0.039(3) -0.001(3) 0.046(3) -0.003(3) F1 0.0370(12) 0.0604(16) 0.0269(13) 0.0028(12) 0.0140(10) 0.0082(12) F2 0.0725(17) 0.077(2) 0.0274(14) 0.0105(13) 0.0272(13) 0.0142(15) F3 0.0813(18) 0.0751(19) 0.0542(17) 0.0019(15) 0.0571(15) -0.0004(15) F4 0.0457(14) 0.0578(16) 0.0614(17) -0.0045(13) 0.0398(13) -0.0076(12) F5 0.0297(11) 0.0384(13) 0.0311(13) -0.0007(10) 0.0151(10) -0.0037(10) F6 0.100(2) 0.0346(15) 0.0471(17) 0.0146(12) 0.0499(17) 0.0197(14) F7 0.181(3) 0.0247(15) 0.101(3) 0.0170(16) 0.104(3) 0.0152(18) F8 0.152(3) 0.0358(17) 0.152(3) -0.0484(19) 0.108(3) -0.0431(19) F9 0.0587(17) 0.073(2) 0.106(3) -0.0599(19) 0.0417(18) -0.0322(15) F10 0.0347(12) 0.0487(16) 0.0526(16) -0.0224(13) 0.0154(12) -0.0023(12) F11 0.0452(13) 0.0489(15) 0.0365(14) 0.0007(12) 0.0268(11) 0.0124(12) F12 0.0422(14) 0.103(2) 0.0541(17) 0.0160(16) 0.0335(13) 0.0239(14) F13 0.0295(13) 0.103(2) 0.0526(17) 0.0214(16) 0.0150(12) -0.0088(14) F14 0.0466(15) 0.0513(17) 0.0577(18) -0.0072(14) 0.0126(13) -0.0184(13) F15 0.0384(12) 0.0357(13) 0.0503(15) -0.0152(12) 0.0182(12) -0.0012(11) F16 0.0437(12) 0.0445(14) 0.0339(13) 0.0021(11) 0.0260(11) 0.0111(11) F17 0.0591(15) 0.0710(18) 0.0423(15) 0.0211(13) 0.0363(13) 0.0129(13) F18 0.0428(13) 0.0365(14) 0.0524(16) 0.0203(12) 0.0230(12) 0.0036(11) F19 0.0455(13) 0.0220(12) 0.0560(16) -0.0018(11) 0.0243(12) 0.0028(10) F20 0.0456(12) 0.0267(12) 0.0323(13) -0.0057(10) 0.0242(11) 0.0020(10) C67 0.037(2) 0.0221(19) 0.029(2) 0.0009(16) 0.0206(18) 0.0018(16) C68 0.042(2) 0.033(2) 0.031(2) 0.0037(18) 0.0211(19) 0.0067(18) C69 0.052(3) 0.039(2) 0.030(2) 0.003(2) 0.024(2) 0.008(2) C70 0.066(3) 0.035(2) 0.044(3) -0.003(2) 0.042(2) -0.002(2) C71 0.043(2) 0.034(2) 0.045(3) -0.004(2) 0.031(2) -0.0049(19) C72 0.038(2) 0.025(2) 0.026(2) -0.0032(17) 0.0169(19) -0.0019(17) C73 0.046(2) 0.024(2) 0.044(3) -0.0059(19) 0.038(2) -0.0036(18) C74 0.081(3) 0.030(2) 0.051(3) 0.001(2) 0.052(3) 0.003(2) C75 0.109(4) 0.022(3) 0.081(4) 0.002(3) 0.076(4) 0.002(3) C76 0.098(4) 0.029(3) 0.092(4) -0.022(3) 0.075(4) -0.023(3) C77 0.052(3) 0.049(3) 0.072(4) -0.031(3) 0.044(3) -0.022(2) C78 0.044(2) 0.027(2) 0.055(3) -0.015(2) 0.036(2) -0.010(2) C79 0.0309(19) 0.026(2) 0.026(2) 0.0099(17) 0.0130(17) 0.0058(16) C80 0.036(2) 0.034(2) 0.029(2) 0.0088(19) 0.0206(18) 0.0075(18) C81 0.031(2) 0.062(3) 0.032(2) 0.022(2) 0.018(2) 0.017(2) C82 0.030(2) 0.061(3) 0.036(3) 0.017(2) 0.012(2) -0.001(2) C83 0.036(2) 0.041(3) 0.033(3) 0.006(2) 0.007(2) -0.007(2) C84 0.030(2) 0.032(2) 0.032(2) 0.0023(19) 0.0131(19) 0.0017(18) C85 0.0192(17) 0.026(2) 0.022(2) -0.0009(16) 0.0098(16) -0.0019(15) C86 0.0257(18) 0.030(2) 0.032(2) -0.0006(18) 0.0167(18) -0.0006(16) C87 0.032(2) 0.043(2) 0.027(2) 0.0056(19) 0.0184(18) -0.0038(18) C88 0.0279(19) 0.032(2) 0.034(2) 0.0110(18) 0.0129(18) -0.0028(17) C89 0.0230(18) 0.022(2) 0.039(2) -0.0029(17) 0.0120(18) -0.0027(15) C90 0.0265(18) 0.022(2) 0.025(2) -0.0045(16) 0.0112(17) -0.0066(15) B1 0.031(2) 0.023(2) 0.023(2) 0.0014(18) 0.0148(19) 0.0026(18) _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 Zr1 O2 1.916(2) . ? Zr1 O1 2.151(3) . ? Zr1 C5 2.513(4) . ? Zr1 C15 2.519(3) . ? Zr1 C11 2.521(4) . ? Zr1 C3 2.543(4) . ? Zr1 C1 2.545(3) . ? Zr1 C12 2.544(4) . ? Zr1 C2 2.554(3) . ? Zr1 C14 2.558(3) . ? Zr1 C4 2.560(4) . ? Zr1 C13 2.578(3) . ? P1 N1 1.683(3) . ? P1 C26 1.852(4) . ? P1 C30 1.858(4) . ? P1 C22A 1.861(5) . ? P1 C26A 1.867(5) . ? P1 C22 1.881(4) . ? P1 C30A 1.885(5) . ? O1 N2 1.300(4) . ? O2 C21 1.397(4) . ? N2 N1 1.266(4) . ? C1 C2 1.397(5) . ? C1 C5 1.411(5) . ? C1 C6 1.498(5) . ? C2 C3 1.416(5) . ? C2 C7 1.496(5) . ? C3 C4 1.410(5) . ? C3 C8 1.498(5) . ? C4 C5 1.425(5) . ? C4 C9 1.501(5) . ? C5 C10 1.505(6) . ? C11 C12 1.414(5) . ? C11 C15 1.417(5) . ? C11 C16 1.498(5) . ? C12 C13 1.418(5) . ? C12 C17 1.510(5) . ? C13 C14 1.405(5) . ? C13 C18 1.494(5) . ? C14 C15 1.418(5) . ? C14 C19 1.503(5) . ? C15 C20 1.504(5) . ? C22 C25 1.531(5) . ? C22 C27 1.545(5) . ? C22 C23 1.549(5) . ? C26 C29 1.525(4) . ? C26 C31 1.525(4) . ? C26 C28 1.527(4) . ? C30 C24 1.536(5) . ? C30 C33 1.539(5) . ? C30 C32 1.540(5) . ? C22A C27A 1.549(5) . ? C22A C23A 1.552(5) . ? C26A C31A 1.527(5) . ? C30A C33A 1.542(5) . ? C30A C32A 1.544(5) . ? C30A C24A 1.546(5) . ? F1 C68 1.348(4) . ? F2 C69 1.349(4) . ? F3 C70 1.342(4) . ? F4 C71 1.342(4) . ? F5 C72 1.345(4) . ? F6 C74 1.363(5) . ? F7 C75 1.335(5) . ? F8 C76 1.341(5) . ? F9 C77 1.357(5) . ? F10 C78 1.346(5) . ? F11 C80 1.353(4) . ? F12 C81 1.350(5) . ? F13 C82 1.343(4) . ? F14 C83 1.350(5) . ? F15 C84 1.353(4) . ? F16 C86 1.348(4) . ? F17 C87 1.344(4) . ? F18 C88 1.339(4) . ? F19 C89 1.344(4) . ? F20 C90 1.347(4) . ? C67 C68 1.375(5) . ? C67 C72 1.403(5) . ? C67 B1 1.636(5) . ? C68 C69 1.385(5) . ? C69 C70 1.374(6) . ? C70 C71 1.365(6) . ? C71 C72 1.371(5) . ? C73 C74 1.381(6) . ? C73 C78 1.381(6) . ? C73 B1 1.654(6) . ? C74 C75 1.378(6) . ? C75 C76 1.382(7) . ? C76 C77 1.339(7) . ? C77 C78 1.385(6) . ? C79 C84 1.381(5) . ? C79 C80 1.387(5) . ? C79 B1 1.663(5) . ? C80 C81 1.385(5) . ? C81 C82 1.356(6) . ? C82 C83 1.379(6) . ? C83 C84 1.372(5) . ? C85 C86 1.376(5) . ? C85 C90 1.391(5) . ? C85 B1 1.652(5) . ? C86 C87 1.370(5) . ? C87 C88 1.376(5) . ? C88 C89 1.365(5) . ? C89 C90 1.371(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 O2 Zr1 O1 96.27(11) . . ? O2 Zr1 C5 94.39(12) . . ? O1 Zr1 C5 128.75(11) . . ? O2 Zr1 C15 85.37(11) . . ? O1 Zr1 C15 86.57(12) . . ? C5 Zr1 C15 144.30(13) . . ? O2 Zr1 C11 81.69(11) . . ? O1 Zr1 C11 119.21(11) . . ? C5 Zr1 C11 111.90(13) . . ? C15 Zr1 C11 32.65(12) . . ? O2 Zr1 C3 130.14(11) . . ? O1 Zr1 C3 82.11(11) . . ? C5 Zr1 C3 53.86(13) . . ? C15 Zr1 C3 143.57(13) . . ? C11 Zr1 C3 141.83(13) . . ? O2 Zr1 C1 79.12(11) . . ? O1 Zr1 C1 102.02(11) . . ? C5 Zr1 C1 32.39(12) . . ? C15 Zr1 C1 162.95(13) . . ? C11 Zr1 C1 136.02(13) . . ? C3 Zr1 C1 53.17(12) . . ? O2 Zr1 C12 110.11(12) . . ? O1 Zr1 C12 128.07(11) . . ? C5 Zr1 C12 93.84(12) . . ? C15 Zr1 C12 53.65(12) . . ? C11 Zr1 C12 32.41(11) . . ? C3 Zr1 C12 109.42(12) . . ? C1 Zr1 C12 125.88(12) . . ? O2 Zr1 C2 98.88(12) . . ? O1 Zr1 C2 75.31(11) . . ? C5 Zr1 C2 53.52(13) . . ? C15 Zr1 C2 161.70(13) . . ? C11 Zr1 C2 165.42(13) . . ? C3 Zr1 C2 32.25(12) . . ? C1 Zr1 C2 31.79(12) . . ? C12 Zr1 C2 138.24(12) . . ? O2 Zr1 C14 116.43(12) . . ? O1 Zr1 C14 75.06(11) . . ? C5 Zr1 C14 140.10(13) . . ? C15 Zr1 C14 32.43(12) . . ? C11 Zr1 C14 53.76(12) . . ? C3 Zr1 C14 111.20(13) . . ? C1 Zr1 C14 164.27(12) . . ? C12 Zr1 C14 53.31(12) . . ? C2 Zr1 C14 135.70(13) . . ? O2 Zr1 C4 126.83(12) . . ? O1 Zr1 C4 113.78(11) . . ? C5 Zr1 C4 32.62(12) . . ? C15 Zr1 C4 136.40(12) . . ? C11 Zr1 C4 115.10(13) . . ? C3 Zr1 C4 32.08(12) . . ? C1 Zr1 C4 53.19(12) . . ? C12 Zr1 C4 85.23(12) . . ? C2 Zr1 C4 53.09(12) . . ? C14 Zr1 C4 113.30(12) . . ? O2 Zr1 C13 134.34(11) . . ? O1 Zr1 C13 98.96(11) . . ? C5 Zr1 C13 108.40(12) . . ? C15 Zr1 C13 53.16(12) . . ? C11 Zr1 C13 53.37(12) . . ? C3 Zr1 C13 94.58(12) . . ? C1 Zr1 C13 137.68(12) . . ? C12 Zr1 C13 32.14(11) . . ? C2 Zr1 C13 126.58(12) . . ? C14 Zr1 C13 31.75(11) . . ? C4 Zr1 C13 84.74(12) . . ? N1 P1 C26 115.25(19) . . ? N1 P1 C30 102.6(2) . . ? C26 P1 C30 117.7(2) . . ? N1 P1 C22A 100.5(3) . . ? C26 P1 C22A 137.8(3) . . ? C30 P1 C22A 72.2(3) . . ? N1 P1 C26A 114.2(2) . . ? C26 P1 C26A 30.3(3) . . ? C30 P1 C26A 139.5(2) . . ? C22A P1 C26A 114.8(3) . . ? N1 P1 C22 99.9(2) . . ? C26 P1 C22 109.6(2) . . ? C30 P1 C22 110.2(2) . . ? C22A P1 C22 38.9(3) . . ? C26A P1 C22 80.4(3) . . ? N1 P1 C30A 107.3(3) . . ? C26 P1 C30A 74.6(3) . . ? C30 P1 C30A 46.9(3) . . ? C22A P1 C30A 116.7(4) . . ? C26A P1 C30A 103.6(4) . . ? C22 P1 C30A 147.5(3) . . ? N2 O1 Zr1 123.4(2) . . ? C21 O2 Zr1 169.9(2) . . ? N1 N2 O1 111.9(3) . . ? N2 N1 P1 116.9(3) . . ? C2 C1 C5 108.7(3) . . ? C2 C1 C6 126.4(4) . . ? C5 C1 C6 124.9(4) . . ? C2 C1 Zr1 74.5(2) . . ? C5 C1 Zr1 72.5(2) . . ? C6 C1 Zr1 121.0(2) . . ? C1 C2 C3 108.1(3) . . ? C1 C2 C7 126.0(4) . . ? C3 C2 C7 125.7(4) . . ? C1 C2 Zr1 73.8(2) . . ? C3 C2 Zr1 73.4(2) . . ? C7 C2 Zr1 122.4(2) . . ? C4 C3 C2 108.0(3) . . ? C4 C3 C8 127.2(4) . . ? C2 C3 C8 124.5(4) . . ? C4 C3 Zr1 74.6(2) . . ? C2 C3 Zr1 74.3(2) . . ? C8 C3 Zr1 122.7(3) . . ? C3 C4 C5 107.7(3) . . ? C3 C4 C9 125.9(4) . . ? C5 C4 C9 124.9(4) . . ? C3 C4 Zr1 73.3(2) . . ? C5 C4 Zr1 71.9(2) . . ? C9 C4 Zr1 131.4(3) . . ? C1 C5 C4 107.3(3) . . ? C1 C5 C10 125.5(4) . . ? C4 C5 C10 126.6(4) . . ? C1 C5 Zr1 75.1(2) . . ? C4 C5 Zr1 75.5(2) . . ? C10 C5 Zr1 122.1(3) . . ? C12 C11 C15 107.7(3) . . ? C12 C11 C16 124.4(4) . . ? C15 C11 C16 127.8(4) . . ? C12 C11 Zr1 74.7(2) . . ? C15 C11 Zr1 73.6(2) . . ? C16 C11 Zr1 120.5(2) . . ? C11 C12 C13 108.0(3) . . ? C11 C12 C17 122.7(3) . . ? C13 C12 C17 127.9(3) . . ? C11 C12 Zr1 72.9(2) . . ? C13 C12 Zr1 75.2(2) . . ? C17 C12 Zr1 128.3(2) . . ? C14 C13 C12 108.3(3) . . ? C14 C13 C18 123.4(3) . . ? C12 C13 C18 127.3(3) . . ? C14 C13 Zr1 73.3(2) . . ? C12 C13 Zr1 72.6(2) . . ? C18 C13 Zr1 128.7(2) . . ? C13 C14 C15 107.8(3) . . ? C13 C14 C19 125.2(4) . . ? C15 C14 C19 126.9(4) . . ? C13 C14 Zr1 74.9(2) . . ? C15 C14 Zr1 72.3(2) . . ? C19 C14 Zr1 121.8(3) . . ? C11 C15 C14 108.2(3) . . ? C11 C15 C20 126.8(4) . . ? C14 C15 C20 125.0(4) . . ? C11 C15 Zr1 73.8(2) . . ? C14 C15 Zr1 75.3(2) . . ? C20 C15 Zr1 119.0(3) . . ? C25 C22 C27 105.4(5) . . ? C25 C22 C23 102.7(5) . . ? C27 C22 C23 108.6(5) . . ? C25 C22 P1 109.9(3) . . ? C27 C22 P1 114.0(4) . . ? C23 C22 P1 115.2(4) . . ? C29 C26 C31 114.0(5) . . ? C29 C26 C28 108.7(4) . . ? C31 C26 C28 102.1(4) . . ? C29 C26 P1 111.9(3) . . ? C31 C26 P1 106.0(4) . . ? C28 C26 P1 113.9(3) . . ? C24 C30 C33 103.2(5) . . ? C24 C30 C32 109.2(5) . . ? C33 C30 C32 110.9(6) . . ? C24 C30 P1 113.4(4) . . ? C33 C30 P1 107.4(4) . . ? C32 C30 P1 112.4(4) . . ? C27A C22A C23A 104.7(7) . . ? C27A C22A P1 103.8(6) . . ? C23A C22A P1 105.9(6) . . ? C31A C26A P1 106.5(6) . . ? C33A C30A C32A 103.9(10) . . ? C33A C30A C24A 96.7(9) . . ? C32A C30A C24A 106.1(8) . . ? C33A C30A P1 114.1(8) . . ? C32A C30A P1 115.9(6) . . ? C24A C30A P1 117.6(7) . . ? C68 C67 C72 113.2(3) . . ? C68 C67 B1 127.3(3) . . ? C72 C67 B1 119.3(3) . . ? F1 C68 C67 121.2(3) . . ? F1 C68 C69 115.5(3) . . ? C67 C68 C69 123.3(4) . . ? F2 C69 C70 119.6(4) . . ? F2 C69 C68 119.8(4) . . ? C70 C69 C68 120.6(4) . . ? F3 C70 C71 120.7(4) . . ? F3 C70 C69 120.5(4) . . ? C71 C70 C69 118.8(4) . . ? F4 C71 C70 120.0(4) . . ? F4 C71 C72 121.0(4) . . ? C70 C71 C72 119.0(4) . . ? F5 C72 C71 115.9(3) . . ? F5 C72 C67 119.0(3) . . ? C71 C72 C67 125.1(4) . . ? C74 C73 C78 112.9(4) . . ? C74 C73 B1 119.7(4) . . ? C78 C73 B1 126.9(3) . . ? F6 C74 C75 115.5(4) . . ? F6 C74 C73 119.0(4) . . ? C75 C74 C73 125.5(5) . . ? F7 C75 C74 121.3(5) . . ? F7 C75 C76 120.8(5) . . ? C74 C75 C76 117.9(5) . . ? C77 C76 F8 121.1(6) . . ? C77 C76 C75 119.6(4) . . ? F8 C76 C75 119.3(5) . . ? C76 C77 F9 120.3(4) . . ? C76 C77 C78 120.4(5) . . ? F9 C77 C78 119.2(5) . . ? F10 C78 C73 121.2(3) . . ? F10 C78 C77 115.2(4) . . ? C73 C78 C77 123.6(4) . . ? C84 C79 C80 112.5(3) . . ? C84 C79 B1 119.5(3) . . ? C80 C79 B1 127.3(3) . . ? F11 C80 C81 114.8(3) . . ? F11 C80 C79 120.9(3) . . ? C81 C80 C79 124.2(4) . . ? F12 C81 C82 119.8(4) . . ? F12 C81 C80 120.0(4) . . ? C82 C81 C80 120.2(4) . . ? F13 C82 C81 121.4(4) . . ? F13 C82 C83 120.3(4) . . ? C81 C82 C83 118.3(4) . . ? F14 C83 C84 121.0(4) . . ? F14 C83 C82 119.5(4) . . ? C84 C83 C82 119.5(4) . . ? F15 C84 C83 115.7(4) . . ? F15 C84 C79 119.1(3) . . ? C83 C84 C79 125.1(4) . . ? C86 C85 C90 113.2(3) . . ? C86 C85 B1 119.9(3) . . ? C90 C85 B1 126.4(3) . . ? F16 C86 C87 116.3(3) . . ? F16 C86 C85 119.5(3) . . ? C87 C86 C85 124.2(3) . . ? F17 C87 C86 121.0(4) . . ? F17 C87 C88 119.0(3) . . ? C86 C87 C88 120.1(4) . . ? F18 C88 C89 121.2(4) . . ? F18 C88 C87 120.5(4) . . ? C89 C88 C87 118.3(3) . . ? F19 C89 C88 120.0(3) . . ? F19 C89 C90 120.2(4) . . ? C88 C89 C90 119.8(4) . . ? F20 C90 C89 115.2(3) . . ? F20 C90 C85 120.6(3) . . ? C89 C90 C85 124.2(4) . . ? C67 B1 C85 113.5(3) . . ? C67 B1 C73 101.8(3) . . ? C85 B1 C73 113.7(3) . . ? C67 B1 C79 114.9(3) . . ? C85 B1 C79 100.5(3) . . ? C73 B1 C79 113.0(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.826 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.086 _vrf_PLAT601_rneu41 ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 72.00 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). 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 72 \%A^3^ containing approximately 18 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. ; # end Validation Reply Form # Attachment 'All-Compounds.cif' data_C30H30BF12N2OP_compound5 _database_code_depnum_ccdc_archive 'CCDC 786852' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C30 H30 B F12 N2 O P' _chemical_formula_weight 704.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.6507(6) _cell_length_b 13.7877(6) _cell_length_c 19.5448(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3139.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6705 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.65 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6472 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28943 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7187 _reflns_number_gt 6151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.5434P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(8) _refine_ls_number_reflns 7187 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 F1 F 1.13977(11) 0.44032(10) 0.00643(6) 0.0352(3) Uani 1 1 d . . . P1 P 0.79001(4) 0.44369(4) 0.08161(3) 0.02105(11) Uani 1 1 d . . . F8 F 1.33263(11) 0.57668(9) 0.27213(6) 0.0343(3) Uani 1 1 d . . . F7 F 1.47966(13) 0.46821(12) 0.34051(7) 0.0528(4) Uani 1 1 d . . . F6 F 1.40331(13) 0.20450(10) 0.19480(8) 0.0452(4) Uani 1 1 d . . . F4 F 1.36941(10) 0.65176(9) 0.14035(7) 0.0335(3) Uani 1 1 d . . . F3 F 1.48289(12) 0.70402(10) 0.02850(9) 0.0537(4) Uani 1 1 d . . . F12 F 1.14758(13) 0.72244(9) 0.10595(7) 0.0389(3) Uani 1 1 d . . . F11 F 1.04164(15) 0.85486(11) 0.17571(8) 0.0562(5) Uani 1 1 d . . . F10 F 0.97304(14) 0.63088(13) 0.35411(8) 0.0598(5) Uani 1 1 d . . . F9 F 1.09072(12) 0.49757(10) 0.28551(6) 0.0385(3) Uani 1 1 d . . . F5 F 1.25962(11) 0.31282(9) 0.12335(7) 0.0350(3) Uani 1 1 d . . . F2 F 1.25248(15) 0.49248(14) -0.10286(7) 0.0614(5) Uani 1 1 d . . . O1 O 1.09225(10) 0.43772(9) 0.14005(6) 0.0198(3) Uani 1 1 d . . . N1 N 0.92389(14) 0.40747(12) 0.10663(9) 0.0222(3) Uani 1 1 d . . . N2 N 0.99418(14) 0.47472(11) 0.11739(8) 0.0207(3) Uani 1 1 d . . . C19 C 1.28294(15) 0.44962(14) 0.19609(9) 0.0196(4) Uani 1 1 d . . . C24 C 1.34535(17) 0.48400(15) 0.25130(10) 0.0253(4) Uani 1 1 d . . . C23 C 1.42249(18) 0.42803(17) 0.28735(11) 0.0326(5) Uani 1 1 d . . . C22 C 1.44332(19) 0.33342(18) 0.27047(12) 0.0338(5) Uani 1 1 d . . . C21 C 1.38530(19) 0.29758(16) 0.21518(12) 0.0303(5) Uani 1 1 d . . . C20 C 1.30915(16) 0.35419(15) 0.17864(10) 0.0245(4) Uani 1 1 d . . . C13 C 1.24932(15) 0.54322(14) 0.07998(10) 0.0209(4) Uani 1 1 d . . . C18 C 1.33891(17) 0.60996(15) 0.08001(11) 0.0273(4) Uani 1 1 d . . . C17 C 1.3970(2) 0.63833(17) 0.02218(14) 0.0380(6) Uani 1 1 d . . . C16 C 1.3707(2) 0.6001(2) -0.04042(14) 0.0459(7) Uani 1 1 d . . . C15 C 1.2832(2) 0.5337(2) -0.04273(11) 0.0406(6) Uani 1 1 d . . . C25 C 1.12859(16) 0.60230(14) 0.19336(10) 0.0219(4) Uani 1 1 d . . . C30 C 1.10991(18) 0.69544(16) 0.16862(11) 0.0284(5) Uani 1 1 d . . . C29 C 1.0511(2) 0.76550(17) 0.20446(13) 0.0372(6) Uani 1 1 d . . . C28 C 1.0030(2) 0.74726(19) 0.26695(13) 0.0416(6) Uani 1 1 d . . . C27 C 1.01809(19) 0.6548(2) 0.29262(12) 0.0396(6) Uani 1 1 d . . . C26 C 1.07997(18) 0.58590(16) 0.25721(11) 0.0285(5) Uani 1 1 d . . . C9 C 0.73222(17) 0.52470(17) 0.15075(11) 0.0307(5) Uani 1 1 d . . . C11 C 0.7725(2) 0.4897(2) 0.22197(11) 0.0416(6) Uani 1 1 d . . . H19A H 0.7441 0.5331 0.2565 0.062 Uiso 1 1 calc R . . H19B H 0.8548 0.4887 0.2234 0.062 Uiso 1 1 calc R . . H19C H 0.7435 0.4256 0.2303 0.062 Uiso 1 1 calc R . . C12 C 0.7773(2) 0.62912(17) 0.14263(13) 0.0403(6) Uani 1 1 d . . . H20A H 0.7486 0.6562 0.1007 0.060 Uiso 1 1 calc R . . H20B H 0.8597 0.6284 0.1416 0.060 Uiso 1 1 calc R . . H20C H 0.7517 0.6678 0.1805 0.060 Uiso 1 1 calc R . . C10 C 0.59986(19) 0.5272(2) 0.14894(13) 0.0423(6) Uani 1 1 d . . . H21A H 0.5723 0.5726 0.1824 0.063 Uiso 1 1 calc R . . H21B H 0.5703 0.4638 0.1590 0.063 Uiso 1 1 calc R . . H21C H 0.5746 0.5468 0.1043 0.063 Uiso 1 1 calc R . . C1 C 0.79739(18) 0.50310(16) -0.00475(10) 0.0267(4) Uani 1 1 d . . . C2 C 0.8920(2) 0.58135(16) -0.00666(12) 0.0332(5) Uani 1 1 d . . . H23A H 0.9651 0.5519 0.0023 0.050 Uiso 1 1 calc R . . H23B H 0.8765 0.6296 0.0275 0.050 Uiso 1 1 calc R . . H23C H 0.8933 0.6113 -0.0510 0.050 Uiso 1 1 calc R . . C3 C 0.8290(2) 0.42843(19) -0.05988(11) 0.0400(6) Uani 1 1 d . . . H24A H 0.8348 0.4602 -0.1034 0.060 Uiso 1 1 calc R . . H24B H 0.7706 0.3794 -0.0620 0.060 Uiso 1 1 calc R . . H24C H 0.9013 0.3990 -0.0487 0.060 Uiso 1 1 calc R . . C5 C 0.71926(19) 0.32164(16) 0.07823(13) 0.0345(5) Uani 1 1 d . . . C7 C 0.6035(2) 0.3242(2) 0.03974(16) 0.0517(7) Uani 1 1 d . . . H26A H 0.5675 0.2617 0.0426 0.078 Uiso 1 1 calc R . . H26B H 0.6167 0.3403 -0.0074 0.078 Uiso 1 1 calc R . . H26C H 0.5544 0.3720 0.0601 0.078 Uiso 1 1 calc R . . C6 C 0.8011(2) 0.24851(16) 0.04369(14) 0.0439(6) Uani 1 1 d . . . H27A H 0.8737 0.2489 0.0670 0.066 Uiso 1 1 calc R . . H27B H 0.8122 0.2665 -0.0033 0.066 Uiso 1 1 calc R . . H27C H 0.7684 0.1847 0.0459 0.066 Uiso 1 1 calc R . . C8 C 0.6984(2) 0.28408(19) 0.15116(14) 0.0449(6) Uani 1 1 d . . . H28A H 0.6679 0.2195 0.1491 0.067 Uiso 1 1 calc R . . H28B H 0.6446 0.3258 0.1740 0.067 Uiso 1 1 calc R . . H28C H 0.7695 0.2836 0.1759 0.067 Uiso 1 1 calc R . . C14 C 1.22506(18) 0.50626(16) 0.01554(10) 0.0278(4) Uani 1 1 d . . . B1 B 1.18809(17) 0.51205(16) 0.15190(11) 0.0181(4) Uani 1 1 d . . . C4 C 0.68124(19) 0.54950(19) -0.02305(12) 0.0383(6) Uani 1 1 d . . . H1A H 0.6840 0.5737 -0.0691 0.058 Uiso 1 1 calc R . . H1B H 0.6657 0.6020 0.0078 0.058 Uiso 1 1 calc R . . H1C H 0.6216 0.5017 -0.0194 0.058 Uiso 1 1 calc R . . H2 H 1.490(2) 0.2983(17) 0.2937(12) 0.033(6) Uiso 1 1 d . . . H3 H 0.964(2) 0.7937(19) 0.2887(14) 0.043(7) Uiso 1 1 d . . . H1 H 1.409(3) 0.613(2) -0.0790(15) 0.055(8) Uiso 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 F1 0.0353(7) 0.0465(7) 0.0239(6) -0.0127(6) -0.0033(5) 0.0052(6) P1 0.0172(2) 0.0234(2) 0.0226(2) 0.0023(2) -0.00203(19) -0.0013(2) F8 0.0401(7) 0.0324(7) 0.0304(7) -0.0102(6) -0.0101(5) -0.0022(6) F7 0.0522(9) 0.0679(10) 0.0384(8) -0.0056(7) -0.0283(7) 0.0011(8) F6 0.0487(9) 0.0299(7) 0.0570(9) -0.0002(7) -0.0089(7) 0.0144(6) F4 0.0267(6) 0.0301(7) 0.0435(8) 0.0002(6) -0.0016(5) -0.0063(5) F3 0.0349(8) 0.0394(8) 0.0869(12) 0.0277(8) 0.0223(8) 0.0015(6) F12 0.0558(9) 0.0297(7) 0.0312(7) 0.0041(6) -0.0007(6) 0.0141(6) F11 0.0741(11) 0.0346(8) 0.0599(10) -0.0146(7) -0.0226(8) 0.0297(8) F10 0.0539(9) 0.0846(12) 0.0409(8) -0.0287(9) 0.0266(7) -0.0152(9) F9 0.0474(8) 0.0419(7) 0.0261(6) -0.0016(6) 0.0121(6) -0.0146(6) F5 0.0396(7) 0.0308(6) 0.0347(7) -0.0123(6) -0.0113(6) 0.0099(6) F2 0.0721(11) 0.0950(12) 0.0173(6) -0.0018(8) 0.0042(6) 0.0222(10) O1 0.0183(6) 0.0196(6) 0.0215(7) -0.0006(6) -0.0033(5) 0.0020(5) N1 0.0186(8) 0.0224(8) 0.0255(8) 0.0001(7) -0.0033(7) -0.0012(6) N2 0.0186(7) 0.0255(9) 0.0181(8) -0.0017(7) -0.0004(6) 0.0013(6) C19 0.0176(8) 0.0239(9) 0.0171(8) 0.0036(8) 0.0017(7) -0.0023(8) C24 0.0234(10) 0.0293(11) 0.0232(10) 0.0006(9) 0.0001(8) -0.0015(8) C23 0.0284(11) 0.0471(14) 0.0223(10) 0.0039(10) -0.0100(8) -0.0052(10) C22 0.0267(11) 0.0432(14) 0.0315(12) 0.0143(11) -0.0051(9) 0.0068(10) C21 0.0299(11) 0.0265(11) 0.0346(12) 0.0054(10) 0.0033(9) 0.0053(9) C20 0.0212(10) 0.0295(10) 0.0227(10) -0.0015(9) 0.0004(8) 0.0006(8) C13 0.0212(8) 0.0212(9) 0.0203(9) 0.0017(8) 0.0015(7) 0.0053(7) C18 0.0239(10) 0.0265(10) 0.0314(11) 0.0069(10) 0.0040(9) 0.0068(8) C17 0.0277(11) 0.0335(12) 0.0529(15) 0.0194(12) 0.0120(10) 0.0072(10) C16 0.0446(15) 0.0582(17) 0.0348(14) 0.0216(13) 0.0190(12) 0.0195(13) C15 0.0444(14) 0.0588(16) 0.0185(10) 0.0062(10) 0.0055(10) 0.0203(13) C25 0.0167(9) 0.0254(10) 0.0236(10) -0.0074(8) -0.0020(7) -0.0022(7) C30 0.0262(10) 0.0299(11) 0.0293(11) -0.0089(10) -0.0082(9) 0.0048(9) C29 0.0355(12) 0.0337(12) 0.0424(13) -0.0173(11) -0.0137(11) 0.0149(10) C28 0.0287(12) 0.0458(15) 0.0503(16) -0.0308(13) -0.0072(11) 0.0105(11) C27 0.0260(11) 0.0646(17) 0.0283(12) -0.0227(12) 0.0070(9) -0.0101(11) C26 0.0245(10) 0.0329(12) 0.0280(11) -0.0073(9) 0.0005(8) -0.0081(9) C9 0.0229(10) 0.0409(13) 0.0283(11) -0.0031(10) 0.0048(8) 0.0058(9) C11 0.0359(13) 0.0650(16) 0.0238(11) -0.0037(12) 0.0018(9) 0.0068(12) C12 0.0381(13) 0.0363(13) 0.0464(14) -0.0128(12) 0.0067(11) 0.0076(10) C10 0.0260(11) 0.0614(17) 0.0395(13) 0.0060(13) 0.0073(10) 0.0114(11) C1 0.0267(10) 0.0302(11) 0.0232(10) 0.0048(9) 0.0003(8) 0.0024(9) C2 0.0339(12) 0.0333(12) 0.0325(12) 0.0095(10) 0.0048(9) -0.0037(9) C3 0.0439(13) 0.0503(15) 0.0256(11) -0.0041(11) 0.0016(10) -0.0023(12) C5 0.0275(10) 0.0308(11) 0.0451(13) 0.0087(11) -0.0122(10) -0.0127(9) C7 0.0385(14) 0.0486(16) 0.0678(19) 0.0156(14) -0.0241(13) -0.0202(12) C6 0.0500(16) 0.0258(11) 0.0560(16) -0.0042(11) -0.0167(13) -0.0052(11) C8 0.0319(12) 0.0453(14) 0.0576(16) 0.0247(13) -0.0060(12) -0.0100(11) C14 0.0259(11) 0.0343(11) 0.0231(10) 0.0026(9) 0.0026(8) 0.0126(9) B1 0.0181(10) 0.0201(10) 0.0161(9) -0.0013(9) 0.0003(8) 0.0003(8) C4 0.0305(12) 0.0492(14) 0.0353(12) 0.0145(12) -0.0049(9) 0.0064(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 F1 C14 1.359(3) . ? P1 N1 1.7092(16) . ? P1 C5 1.875(2) . ? P1 C9 1.878(2) . ? P1 C1 1.878(2) . ? F8 C24 1.349(2) . ? F7 C23 1.353(2) . ? F6 C21 1.360(3) . ? F4 C18 1.360(3) . ? F3 C17 1.355(3) . ? F12 C30 1.353(3) . ? F11 C29 1.359(3) . ? F10 C27 1.352(3) . ? F9 C26 1.343(3) . ? F5 C20 1.351(2) . ? F2 C15 1.354(3) . ? O1 N2 1.327(2) . ? O1 B1 1.533(2) . ? N1 N2 1.255(2) . ? C19 C24 1.385(3) . ? C19 C20 1.393(3) . ? C19 B1 1.646(3) . ? C24 C23 1.378(3) . ? C23 C22 1.367(3) . ? C22 C21 1.367(3) . ? C21 C20 1.381(3) . ? C13 C14 1.388(3) . ? C13 C18 1.392(3) . ? C13 B1 1.634(3) . ? C18 C17 1.375(3) . ? C17 C16 1.367(4) . ? C16 C15 1.371(4) . ? C15 C14 1.378(3) . ? C25 C26 1.389(3) . ? C25 C30 1.389(3) . ? C25 B1 1.639(3) . ? C30 C29 1.376(3) . ? C29 C28 1.367(4) . ? C28 C27 1.381(4) . ? C27 C26 1.379(3) . ? C9 C12 1.541(3) . ? C9 C10 1.543(3) . ? C9 C11 1.546(3) . ? C1 C3 1.535(3) . ? C1 C4 1.539(3) . ? C1 C2 1.543(3) . ? C5 C8 1.536(3) . ? C5 C6 1.543(4) . ? C5 C7 1.544(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C5 98.57(9) . . ? N1 P1 C9 107.16(9) . . ? C5 P1 C9 113.67(11) . . ? N1 P1 C1 110.05(9) . . ? C5 P1 C1 112.33(10) . . ? C9 P1 C1 113.81(10) . . ? N2 O1 B1 114.86(14) . . ? N2 N1 P1 115.32(13) . . ? N1 N2 O1 109.49(14) . . ? C24 C19 C20 113.52(17) . . ? C24 C19 B1 125.62(17) . . ? C20 C19 B1 120.85(16) . . ? F8 C24 C23 116.59(18) . . ? F8 C24 C19 120.11(18) . . ? C23 C24 C19 123.30(19) . . ? F7 C23 C22 119.24(19) . . ? F7 C23 C24 119.0(2) . . ? C22 C23 C24 121.8(2) . . ? C21 C22 C23 116.6(2) . . ? F6 C21 C22 119.8(2) . . ? F6 C21 C20 118.8(2) . . ? C22 C21 C20 121.5(2) . . ? F5 C20 C21 116.70(18) . . ? F5 C20 C19 120.06(17) . . ? C21 C20 C19 123.24(19) . . ? C14 C13 C18 113.33(18) . . ? C14 C13 B1 126.53(17) . . ? C18 C13 B1 120.07(17) . . ? F4 C18 C17 117.6(2) . . ? F4 C18 C13 118.47(17) . . ? C17 C18 C13 123.9(2) . . ? F3 C17 C16 120.3(2) . . ? F3 C17 C18 118.6(2) . . ? C16 C17 C18 121.0(2) . . ? C17 C16 C15 117.0(2) . . ? F2 C15 C16 120.3(2) . . ? F2 C15 C14 118.2(2) . . ? C16 C15 C14 121.4(2) . . ? C26 C25 C30 113.52(19) . . ? C26 C25 B1 119.55(18) . . ? C30 C25 B1 126.59(18) . . ? F12 C30 C29 115.4(2) . . ? F12 C30 C25 121.22(18) . . ? C29 C30 C25 123.4(2) . . ? F11 C29 C28 120.2(2) . . ? F11 C29 C30 117.8(2) . . ? C28 C29 C30 122.0(2) . . ? C29 C28 C27 116.2(2) . . ? F10 C27 C26 118.7(2) . . ? F10 C27 C28 119.9(2) . . ? C26 C27 C28 121.3(2) . . ? F9 C26 C27 117.8(2) . . ? F9 C26 C25 118.64(18) . . ? C27 C26 C25 123.5(2) . . ? C12 C9 C10 108.5(2) . . ? C12 C9 C11 106.3(2) . . ? C10 C9 C11 109.33(18) . . ? C12 C9 P1 111.06(15) . . ? C10 C9 P1 110.80(16) . . ? C11 C9 P1 110.71(15) . . ? C3 C1 C4 109.05(19) . . ? C3 C1 C2 106.30(18) . . ? C4 C1 C2 109.39(18) . . ? C3 C1 P1 110.44(15) . . ? C4 C1 P1 110.49(14) . . ? C2 C1 P1 111.07(14) . . ? C8 C5 C6 106.48(19) . . ? C8 C5 C7 108.7(2) . . ? C6 C5 C7 109.9(2) . . ? C8 C5 P1 109.85(16) . . ? C6 C5 P1 109.27(15) . . ? C7 C5 P1 112.39(16) . . ? F1 C14 C15 115.76(19) . . ? F1 C14 C13 120.91(17) . . ? C15 C14 C13 123.3(2) . . ? O1 B1 C13 111.33(15) . . ? O1 B1 C25 105.91(14) . . ? C13 B1 C25 114.23(16) . . ? O1 B1 C19 102.63(15) . . ? C13 B1 C19 107.21(14) . . ? C25 B1 C19 114.94(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.307 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.042 data_C60H66B2F24O2P2_compound7 _database_code_depnum_ccdc_archive 'CCDC 786853' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C60 H66 B2 F24 N4 O2 P2' _chemical_formula_weight 1414.73 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 0.201 0.288 0.700 18 0 ' ' 2 0.500 0.500 0.000 173 68 ' ' 3 0.799 0.712 0.300 18 0 ' ' _platon_squeeze_details ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6910(5) _cell_length_b 12.8326(5) _cell_length_c 13.5442(6) _cell_angle_alpha 63.637(2) _cell_angle_beta 88.082(2) _cell_angle_gamma 72.341(2) _cell_volume 1722.62(13) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9006 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9348 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27807 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7846 _reflns_number_gt 5627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0529P] 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 7846 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.02780(4) 0.27782(4) 0.34834(4) 0.02891(13) Uani 1 1 d . . . F1 F 0.17642(9) 0.15400(10) 0.12544(9) 0.0373(3) Uani 1 1 d . . . F2 F 0.21416(12) 0.27407(12) -0.08182(10) 0.0528(3) Uani 1 1 d . . . F3 F 0.44075(14) 0.23878(13) -0.14240(10) 0.0565(4) Uani 1 1 d . . . F4 F 0.63351(11) 0.07984(12) 0.01414(10) 0.0478(3) Uani 1 1 d . . . F5 F 0.59981(9) -0.03821(10) 0.22641(9) 0.0369(3) Uani 1 1 d . . . F6 F 0.49848(11) 0.16109(10) 0.28649(8) 0.0365(3) Uani 1 1 d . . . F7 F 0.40464(10) -0.18326(10) 0.55724(9) 0.0345(3) Uani 1 1 d . . . F8 F 0.60640(9) -0.24163(10) 0.43032(9) 0.0362(3) Uani 1 1 d . . . F9 F 0.65727(11) -0.46281(10) 0.44454(10) 0.0437(3) Uani 1 1 d . . . F10 F 0.49112(12) -0.52358(11) 0.36191(11) 0.0486(3) Uani 1 1 d . . . F11 F 0.27092(12) -0.35215(12) 0.26442(12) 0.0543(4) Uani 1 1 d . . . F12 F 0.22270(10) -0.12463(10) 0.23827(10) 0.0382(3) Uani 1 1 d . . . O1 O 0.24284(10) 0.00247(11) 0.34355(10) 0.0267(3) Uani 1 1 d . . . N1 N 0.09354(14) 0.13954(15) 0.35104(15) 0.0352(4) Uani 1 1 d . . . N2 N 0.20301(13) 0.11376(14) 0.33637(13) 0.0297(3) Uani 1 1 d . . . C1 C 0.0189(2) 0.2318(2) 0.50036(18) 0.0404(5) Uani 1 1 d . . . C2 C 0.1442(2) 0.1460(2) 0.56510(19) 0.0500(6) Uani 1 1 d . . . H2A H 0.2028 0.1906 0.5416 0.075 Uiso 1 1 calc R . . H2B H 0.1699 0.0748 0.5501 0.075 Uiso 1 1 calc R . . H2C H 0.1395 0.1181 0.6448 0.075 Uiso 1 1 calc R . . C3 C -0.0698(2) 0.1590(3) 0.5439(2) 0.0593(7) Uani 1 1 d . . . H3A H -0.0471 0.0896 0.5264 0.089 Uiso 1 1 calc R . . H3B H -0.1519 0.2127 0.5085 0.089 Uiso 1 1 calc R . . H3C H -0.0672 0.1284 0.6244 0.089 Uiso 1 1 calc R . . C4 C -0.0240(3) 0.3440(2) 0.5228(2) 0.0593(7) Uani 1 1 d . . . H4A H 0.0354 0.3878 0.5021 0.089 Uiso 1 1 calc R . . H4B H -0.0326 0.3168 0.6019 0.089 Uiso 1 1 calc R . . H4C H -0.1022 0.3990 0.4788 0.089 Uiso 1 1 calc R . . C5 C -0.12213(18) 0.3249(2) 0.2674(2) 0.0426(5) Uani 1 1 d . . . C6 C -0.1630(2) 0.2132(2) 0.2957(3) 0.0579(7) Uani 1 1 d . . . H6A H -0.1764 0.1775 0.3740 0.087 Uiso 1 1 calc R . . H6B H -0.1003 0.1518 0.2821 0.087 Uiso 1 1 calc R . . H6C H -0.2383 0.2388 0.2491 0.087 Uiso 1 1 calc R . . C7 C -0.2203(2) 0.4203(3) 0.2894(3) 0.0640(8) Uani 1 1 d . . . H7A H -0.2927 0.4533 0.2367 0.096 Uiso 1 1 calc R . . H7B H -0.1905 0.4874 0.2802 0.096 Uiso 1 1 calc R . . H7C H -0.2404 0.3814 0.3653 0.096 Uiso 1 1 calc R . . C8 C -0.1104(2) 0.3801(2) 0.1421(2) 0.0545(6) Uani 1 1 d . . . H8A H -0.0452 0.3216 0.1273 0.082 Uiso 1 1 calc R . . H8B H -0.0919 0.4567 0.1184 0.082 Uiso 1 1 calc R . . H8C H -0.1866 0.3971 0.1010 0.082 Uiso 1 1 calc R . . C9 C 0.11182(18) 0.39062(17) 0.28244(17) 0.0352(4) Uani 1 1 d . . . C10 C 0.0295(2) 0.52102(19) 0.2548(2) 0.0505(6) Uani 1 1 d . . . H10A H 0.0773 0.5771 0.2302 0.076 Uiso 1 1 calc R . . H10B H -0.0068 0.5211 0.3211 0.076 Uiso 1 1 calc R . . H10C H -0.0345 0.5481 0.1956 0.076 Uiso 1 1 calc R . . C11 C 0.1610(2) 0.3871(2) 0.17608(19) 0.0477(6) Uani 1 1 d . . . H11A H 0.0956 0.3940 0.1278 0.071 Uiso 1 1 calc R . . H11B H 0.2261 0.3094 0.1963 0.071 Uiso 1 1 calc R . . H11C H 0.1923 0.4558 0.1368 0.071 Uiso 1 1 calc R . . C12 C 0.22322(19) 0.3582(2) 0.3609(2) 0.0442(5) Uani 1 1 d . . . H12A H 0.2718 0.4111 0.3215 0.066 Uiso 1 1 calc R . . H12B H 0.2720 0.2720 0.3858 0.066 Uiso 1 1 calc R . . H12C H 0.1968 0.3708 0.4253 0.066 Uiso 1 1 calc R . . C13 C 0.38737(15) 0.05349(16) 0.18917(14) 0.0246(4) Uani 1 1 d . . . C14 C 0.29357(16) 0.13280(16) 0.10513(15) 0.0279(4) Uani 1 1 d . . . C15 C 0.30969(18) 0.19594(17) -0.00475(16) 0.0343(4) Uani 1 1 d . . . C16 C 0.4239(2) 0.17897(18) -0.03567(16) 0.0364(5) Uani 1 1 d . . . C17 C 0.52124(17) 0.09888(18) 0.04350(17) 0.0337(4) Uani 1 1 d . . . C18 C 0.50118(16) 0.03906(16) 0.15234(15) 0.0280(4) Uani 1 1 d . . . C19 C 0.44797(15) -0.01446(15) 0.41179(14) 0.0231(4) Uani 1 1 d . . . C20 C 0.49858(15) 0.07648(16) 0.39216(14) 0.0248(4) Uani 1 1 d . . . C21 C 0.45165(15) -0.08971(15) 0.52467(14) 0.0240(4) Uani 1 1 d . . . C22 C 0.40923(15) -0.17129(16) 0.33744(14) 0.0255(4) Uani 1 1 d . . . C23 C 0.51897(16) -0.26277(17) 0.38670(15) 0.0272(4) Uani 1 1 d . . . C24 C 0.54833(17) -0.37947(17) 0.39494(15) 0.0322(4) Uani 1 1 d . . . C25 C 0.46526(19) -0.41038(17) 0.35400(16) 0.0354(4) Uani 1 1 d . . . C26 C 0.35497(18) -0.32343(19) 0.30418(17) 0.0355(4) Uani 1 1 d . . . C27 C 0.33028(16) -0.20650(17) 0.29490(15) 0.0286(4) Uani 1 1 d . . . B1 B 0.37514(17) -0.02983(18) 0.32028(16) 0.0240(4) Uani 1 1 d . . . C30 C 0.9398(2) 0.0334(3) 0.0836(2) 0.0663(8) Uani 1 1 d . . . H30A H 0.8634 0.0656 0.1098 0.080 Uiso 1 1 calc R . . H30B H 1.0076 0.0133 0.1377 0.080 Uiso 1 1 calc R . . C29 C 0.9509(3) 0.1295(3) -0.0274(3) 0.0746(9) Uani 1 1 d . . . H29A H 0.9580 0.2004 -0.0194 0.090 Uiso 1 1 calc R . . H29B H 0.8767 0.1587 -0.0781 0.090 Uiso 1 1 calc R . . C28 C 0.9411(3) -0.0820(3) 0.0773(3) 0.0806(9) Uani 1 1 d . . . H28A H 0.9414 -0.1464 0.1529 0.097 Uiso 1 1 calc R . . H28B H 0.8664 -0.0642 0.0321 0.097 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 0.0279(2) 0.0262(3) 0.0335(3) -0.0156(2) 0.00432(19) -0.00691(19) F1 0.0262(5) 0.0435(7) 0.0325(6) -0.0136(5) -0.0023(4) -0.0034(5) F2 0.0587(8) 0.0457(7) 0.0292(6) -0.0026(6) -0.0123(6) -0.0046(6) F3 0.0810(10) 0.0577(8) 0.0251(6) -0.0097(6) 0.0166(6) -0.0301(7) F4 0.0452(7) 0.0603(8) 0.0465(7) -0.0279(7) 0.0255(6) -0.0249(6) F5 0.0249(5) 0.0417(6) 0.0362(6) -0.0138(5) 0.0024(4) -0.0064(5) F6 0.0604(7) 0.0315(6) 0.0181(5) -0.0047(5) 0.0038(5) -0.0258(5) F7 0.0516(7) 0.0333(6) 0.0262(6) -0.0111(5) 0.0081(5) -0.0280(5) F8 0.0294(5) 0.0353(6) 0.0410(7) -0.0181(5) -0.0064(5) -0.0045(5) F9 0.0421(6) 0.0314(6) 0.0440(7) -0.0158(5) -0.0003(5) 0.0043(5) F10 0.0681(8) 0.0279(6) 0.0524(8) -0.0215(6) 0.0067(6) -0.0138(6) F11 0.0608(8) 0.0444(7) 0.0687(9) -0.0296(7) -0.0076(7) -0.0240(6) F12 0.0318(6) 0.0376(6) 0.0437(7) -0.0196(5) -0.0085(5) -0.0062(5) O1 0.0261(6) 0.0240(6) 0.0305(7) -0.0132(5) 0.0056(5) -0.0078(5) N1 0.0298(8) 0.0341(9) 0.0446(10) -0.0214(8) 0.0116(7) -0.0096(7) N2 0.0282(8) 0.0355(9) 0.0264(8) -0.0147(7) 0.0055(6) -0.0110(7) C1 0.0487(12) 0.0410(12) 0.0342(11) -0.0191(10) 0.0107(9) -0.0157(10) C2 0.0677(15) 0.0434(13) 0.0321(12) -0.0110(10) 0.0028(10) -0.0182(11) C3 0.0689(16) 0.0623(16) 0.0555(16) -0.0283(13) 0.0321(13) -0.0331(13) C4 0.0783(18) 0.0593(16) 0.0548(15) -0.0405(13) 0.0172(13) -0.0196(14) C5 0.0302(10) 0.0462(12) 0.0540(14) -0.0271(11) -0.0014(9) -0.0085(9) C6 0.0386(12) 0.0638(16) 0.085(2) -0.0409(15) 0.0059(12) -0.0228(12) C7 0.0305(11) 0.0730(18) 0.088(2) -0.0475(16) 0.0007(12) 0.0017(11) C8 0.0469(13) 0.0630(16) 0.0523(15) -0.0276(13) -0.0109(11) -0.0123(11) C9 0.0357(10) 0.0264(10) 0.0365(11) -0.0081(8) -0.0017(8) -0.0098(8) C10 0.0553(14) 0.0242(10) 0.0612(15) -0.0127(10) -0.0107(11) -0.0070(10) C11 0.0511(13) 0.0443(13) 0.0409(13) -0.0085(10) 0.0084(10) -0.0238(11) C12 0.0401(11) 0.0354(11) 0.0522(14) -0.0131(10) -0.0043(10) -0.0154(9) C13 0.0286(9) 0.0235(9) 0.0228(9) -0.0111(7) 0.0025(7) -0.0089(7) C14 0.0293(9) 0.0272(9) 0.0268(9) -0.0130(8) 0.0035(7) -0.0074(7) C15 0.0421(11) 0.0273(10) 0.0249(10) -0.0078(8) -0.0060(8) -0.0054(8) C16 0.0578(13) 0.0308(10) 0.0233(10) -0.0115(8) 0.0120(9) -0.0198(9) C17 0.0367(10) 0.0365(10) 0.0352(11) -0.0200(9) 0.0126(8) -0.0163(8) C18 0.0298(9) 0.0269(9) 0.0267(9) -0.0119(8) 0.0024(7) -0.0087(7) C19 0.0236(8) 0.0217(8) 0.0229(9) -0.0093(7) 0.0027(7) -0.0071(7) C20 0.0297(9) 0.0228(9) 0.0167(8) -0.0044(7) 0.0031(7) -0.0088(7) C21 0.0268(8) 0.0217(8) 0.0246(9) -0.0089(7) 0.0044(7) -0.0120(7) C22 0.0300(9) 0.0255(9) 0.0196(9) -0.0086(7) 0.0045(7) -0.0098(7) C23 0.0294(9) 0.0288(9) 0.0228(9) -0.0116(8) 0.0016(7) -0.0085(7) C24 0.0376(10) 0.0267(10) 0.0245(9) -0.0081(8) 0.0041(8) -0.0056(8) C25 0.0516(12) 0.0246(9) 0.0302(10) -0.0131(8) 0.0097(9) -0.0121(9) C26 0.0426(11) 0.0359(11) 0.0366(11) -0.0192(9) 0.0046(9) -0.0198(9) C27 0.0298(9) 0.0272(9) 0.0253(9) -0.0100(8) 0.0008(7) -0.0071(7) B1 0.0220(9) 0.0249(10) 0.0229(10) -0.0085(8) 0.0019(7) -0.0082(8) C30 0.0529(15) 0.078(2) 0.0688(19) -0.0427(17) -0.0102(13) -0.0060(14) C29 0.0768(19) 0.0581(17) 0.079(2) -0.0369(17) -0.0252(16) 0.0037(15) C28 0.086(2) 0.080(2) 0.084(2) -0.0427(19) 0.0089(18) -0.0293(18) _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 1.6905(16) . ? P1 C9 1.874(2) . ? P1 C5 1.881(2) . ? P1 C1 1.882(2) . ? F1 C14 1.357(2) . ? F2 C15 1.346(2) . ? F3 C16 1.344(2) . ? F4 C17 1.341(2) . ? F5 C18 1.349(2) . ? F6 C20 1.3588(19) . ? F7 C21 1.361(2) . ? F8 C23 1.349(2) . ? F9 C24 1.345(2) . ? F10 C25 1.346(2) . ? F11 C26 1.350(2) . ? F12 C27 1.350(2) . ? O1 N2 1.3198(19) . ? O1 B1 1.536(2) . ? N1 N2 1.253(2) . ? C1 C3 1.534(3) . ? C1 C4 1.535(3) . ? C1 C2 1.541(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.532(3) . ? C5 C7 1.534(3) . ? C5 C8 1.541(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.535(3) . ? C9 C12 1.539(3) . ? C9 C11 1.547(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.383(2) . ? C13 C18 1.393(2) . ? C13 B1 1.645(3) . ? C14 C15 1.382(3) . ? C15 C16 1.368(3) . ? C16 C17 1.376(3) . ? C17 C18 1.378(3) . ? C19 C20 1.384(2) . ? C19 C21 1.393(2) . ? C19 B1 1.640(3) . ? C20 C21 1.382(2) 2_656 ? C21 C20 1.382(2) 2_656 ? C22 C27 1.381(3) . ? C22 C23 1.385(2) . ? C22 B1 1.643(3) . ? C23 C24 1.384(3) . ? C24 C25 1.369(3) . ? C25 C26 1.371(3) . ? C26 C27 1.387(3) . ? C30 C29 1.495(4) . ? C30 C28 1.515(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C29 C28 1.505(4) 2_755 ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C28 C29 1.505(4) 2_755 ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 C9 114.87(9) . . ? N1 P1 C5 99.63(9) . . ? C9 P1 C5 113.14(10) . . ? N1 P1 C1 101.19(9) . . ? C9 P1 C1 113.17(10) . . ? C5 P1 C1 113.56(10) . . ? N2 O1 B1 111.26(13) . . ? N2 N1 P1 116.48(14) . . ? N1 N2 O1 109.81(15) . . ? C3 C1 C4 107.9(2) . . ? C3 C1 C2 107.13(19) . . ? C4 C1 C2 110.6(2) . . ? C3 C1 P1 110.39(16) . . ? C4 C1 P1 111.81(16) . . ? C2 C1 P1 108.85(14) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C7 109.2(2) . . ? C6 C5 C8 106.3(2) . . ? C7 C5 C8 108.6(2) . . ? C6 C5 P1 110.75(16) . . ? C7 C5 P1 111.81(16) . . ? C8 C5 P1 109.99(15) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C12 108.67(18) . . ? C10 C9 C11 109.89(18) . . ? C12 C9 C11 105.86(18) . . ? C10 C9 P1 110.33(15) . . ? C12 C9 P1 110.71(14) . . ? C11 C9 P1 111.26(14) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 113.61(16) . . ? C14 C13 B1 126.66(15) . . ? C18 C13 B1 119.51(15) . . ? F1 C14 C15 114.55(15) . . ? F1 C14 C13 121.54(16) . . ? C15 C14 C13 123.91(17) . . ? F2 C15 C16 119.58(18) . . ? F2 C15 C14 120.68(18) . . ? C16 C15 C14 119.74(17) . . ? F3 C16 C15 120.35(18) . . ? F3 C16 C17 120.33(18) . . ? C15 C16 C17 119.32(17) . . ? F4 C17 C16 119.98(18) . . ? F4 C17 C18 120.99(17) . . ? C16 C17 C18 119.03(17) . . ? F5 C18 C17 116.52(16) . . ? F5 C18 C13 119.13(16) . . ? C17 C18 C13 124.36(17) . . ? C20 C19 C21 112.25(15) . . ? C20 C19 B1 127.36(15) . . ? C21 C19 B1 120.00(15) . . ? F6 C20 C21 116.22(15) . 2_656 ? F6 C20 C19 120.10(15) . . ? C21 C20 C19 123.66(16) 2_656 . ? F7 C21 C20 116.75(15) . 2_656 ? F7 C21 C19 119.17(15) . . ? C20 C21 C19 124.09(16) 2_656 . ? C27 C22 C23 113.55(16) . . ? C27 C22 B1 121.18(15) . . ? C23 C22 B1 125.11(16) . . ? F8 C23 C24 115.19(15) . . ? F8 C23 C22 120.56(16) . . ? C24 C23 C22 124.25(17) . . ? F9 C24 C25 120.11(17) . . ? F9 C24 C23 120.20(18) . . ? C25 C24 C23 119.68(17) . . ? F10 C25 C24 120.86(18) . . ? F10 C25 C26 120.47(19) . . ? C24 C25 C26 118.67(18) . . ? F11 C26 C25 119.79(18) . . ? F11 C26 C27 120.34(17) . . ? C25 C26 C27 119.87(18) . . ? F12 C27 C22 120.26(16) . . ? F12 C27 C26 115.80(16) . . ? C22 C27 C26 123.93(17) . . ? O1 B1 C19 104.47(13) . . ? O1 B1 C22 104.06(14) . . ? C19 B1 C22 114.82(14) . . ? O1 B1 C13 110.99(14) . . ? C19 B1 C13 116.29(14) . . ? C22 B1 C13 105.60(14) . . ? C29 C30 C28 110.9(3) . . ? C29 C30 H30A 109.5 . . ? C28 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 108.0 . . ? C30 C29 C28 112.1(2) . 2_755 ? C30 C29 H29A 109.2 . . ? C28 C29 H29A 109.2 2_755 . ? C30 C29 H29B 109.2 . . ? C28 C29 H29B 109.2 2_755 . ? H29A C29 H29B 107.9 . . ? C29 C28 C30 112.6(3) 2_755 . ? C29 C28 H28A 109.1 2_755 . ? C30 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 2_755 . ? C30 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.385 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.055 data_C36H36BF12N2OP_compound8 _database_code_depnum_ccdc_archive 'CCDC 786854' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C36 H36 B F12 N2 O P' _chemical_formula_weight 782.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 19.5019(10) _cell_length_b 16.3963(7) _cell_length_c 21.7273(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6947.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7230 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 22.78 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9086 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60514 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.57 _reflns_number_total 7992 _reflns_number_gt 5435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+3.3204P] 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 7992 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 1.01509(3) 0.36743(3) 0.42023(2) 0.01800(11) Uani 1 1 d . . . F1 F 0.96358(7) 0.08192(8) 0.54571(6) 0.0408(3) Uani 1 1 d . . . F2 F 0.91018(9) 0.01441(9) 0.44743(6) 0.0580(4) Uani 1 1 d . . . F3 F 0.74414(9) 0.22163(11) 0.43724(7) 0.0673(5) Uani 1 1 d . . . F4 F 0.79804(7) 0.29302(8) 0.53562(6) 0.0419(3) Uani 1 1 d . . . F5 F 0.95036(6) 0.36089(8) 0.69842(5) 0.0360(3) Uani 1 1 d . . . F6 F 0.87215(7) 0.40587(9) 0.79269(6) 0.0480(4) Uani 1 1 d . . . F7 F 0.69866(7) 0.22820(9) 0.72456(6) 0.0444(4) Uani 1 1 d . . . F8 F 0.77455(6) 0.18208(8) 0.63227(5) 0.0367(3) Uani 1 1 d . . . F9 F 0.91291(6) 0.09957(7) 0.67330(5) 0.0279(3) Uani 1 1 d . . . F10 F 1.01582(7) 0.02159(7) 0.72804(5) 0.0341(3) Uani 1 1 d . . . F11 F 1.16991(7) 0.21801(10) 0.65144(6) 0.0525(4) Uani 1 1 d . . . F12 F 1.06926(6) 0.29859(8) 0.60016(5) 0.0354(3) Uani 1 1 d . . . O1 O 0.93646(7) 0.32811(7) 0.57209(5) 0.0204(3) Uani 1 1 d . . . N1 N 0.97907(8) 0.38291(9) 0.49127(7) 0.0206(3) Uani 1 1 d . . . N2 N 0.96590(8) 0.31611(9) 0.51736(7) 0.0199(3) Uani 1 1 d . . . C1 C 1.03200(10) 0.25968(11) 0.40570(9) 0.0226(4) Uani 1 1 d . . . H1 H 0.9902 0.2295 0.4196 0.027 Uiso 1 1 calc R . . C2 C 1.04072(12) 0.23990(12) 0.33679(9) 0.0292(5) Uani 1 1 d . . . H2A H 1.0000 0.2591 0.3137 0.035 Uiso 1 1 calc R . . H2B H 1.0815 0.2686 0.3205 0.035 Uiso 1 1 calc R . . C3 C 1.04918(14) 0.14786(14) 0.32796(12) 0.0426(6) Uani 1 1 d . . . H3A H 1.0059 0.1202 0.3394 0.051 Uiso 1 1 calc R . . H3B H 1.0582 0.1364 0.2840 0.051 Uiso 1 1 calc R . . C4 C 1.10728(13) 0.11327(13) 0.36644(11) 0.0387(6) Uani 1 1 d . . . H4A H 1.1514 0.1360 0.3519 0.046 Uiso 1 1 calc R . . H4B H 1.1089 0.0533 0.3612 0.046 Uiso 1 1 calc R . . C5 C 1.09775(13) 0.13360(13) 0.43418(10) 0.0361(5) Uani 1 1 d . . . H5A H 1.1372 0.1124 0.4580 0.043 Uiso 1 1 calc R . . H5B H 1.0556 0.1069 0.4497 0.043 Uiso 1 1 calc R . . C6 C 1.09222(11) 0.22547(12) 0.44343(9) 0.0280(5) Uani 1 1 d . . . H6A H 1.1354 0.2520 0.4303 0.034 Uiso 1 1 calc R . . H6B H 1.0851 0.2376 0.4876 0.034 Uiso 1 1 calc R . . C7 C 0.95164(10) 0.40317(11) 0.36537(8) 0.0199(4) Uani 1 1 d . . . H7 H 0.9702 0.3927 0.3232 0.024 Uiso 1 1 calc R . . C8 C 0.88498(10) 0.35380(12) 0.37181(9) 0.0269(5) Uani 1 1 d . . . H8A H 0.8949 0.2952 0.3656 0.032 Uiso 1 1 calc R . . H8B H 0.8664 0.3607 0.4139 0.032 Uiso 1 1 calc R . . C9 C 0.83151(11) 0.38172(13) 0.32485(10) 0.0329(5) Uani 1 1 d . . . H9A H 0.8483 0.3698 0.2828 0.039 Uiso 1 1 calc R . . H9B H 0.7884 0.3509 0.3313 0.039 Uiso 1 1 calc R . . C10 C 0.81718(12) 0.47255(14) 0.33077(11) 0.0366(5) Uani 1 1 d . . . H10A H 0.7841 0.4894 0.2986 0.044 Uiso 1 1 calc R . . H10B H 0.7962 0.4837 0.3714 0.044 Uiso 1 1 calc R . . C11 C 0.88269(12) 0.52177(13) 0.32417(11) 0.0348(5) Uani 1 1 d . . . H11A H 0.8723 0.5803 0.3305 0.042 Uiso 1 1 calc R . . H11B H 0.9008 0.5151 0.2819 0.042 Uiso 1 1 calc R . . C12 C 0.93745(11) 0.49509(12) 0.37051(10) 0.0272(5) Uani 1 1 d . . . H12A H 0.9218 0.5080 0.4127 0.033 Uiso 1 1 calc R . . H12B H 0.9804 0.5257 0.3628 0.033 Uiso 1 1 calc R . . C13 C 1.08801(10) 0.43498(11) 0.42210(8) 0.0197(4) Uani 1 1 d . . . H13 H 1.0688 0.4910 0.4281 0.024 Uiso 1 1 calc R . . C14 C 1.12901(10) 0.43838(13) 0.36184(8) 0.0253(4) Uani 1 1 d . . . H14A H 1.1513 0.3851 0.3543 0.030 Uiso 1 1 calc R . . H14B H 1.0977 0.4499 0.3270 0.030 Uiso 1 1 calc R . . C15 C 1.18351(12) 0.50530(14) 0.36618(10) 0.0356(5) Uani 1 1 d . . . H15A H 1.2125 0.5034 0.3288 0.043 Uiso 1 1 calc R . . H15B H 1.1604 0.5591 0.3671 0.043 Uiso 1 1 calc R . . C16 C 1.22920(11) 0.49758(13) 0.42257(10) 0.0334(5) Uani 1 1 d . . . H16A H 1.2582 0.4483 0.4186 0.040 Uiso 1 1 calc R . . H16B H 1.2599 0.5456 0.4251 0.040 Uiso 1 1 calc R . . C17 C 1.18683(11) 0.49180(13) 0.48087(10) 0.0297(5) Uani 1 1 d . . . H17A H 1.1611 0.5432 0.4869 0.036 Uiso 1 1 calc R . . H17B H 1.2176 0.4842 0.5167 0.036 Uiso 1 1 calc R . . C18 C 1.13662(11) 0.42036(12) 0.47694(9) 0.0266(5) Uani 1 1 d . . . H18A H 1.1099 0.4163 0.5156 0.032 Uiso 1 1 calc R . . H18B H 1.1621 0.3687 0.4711 0.032 Uiso 1 1 calc R . . C19 C 0.88291(11) 0.19104(12) 0.54691(8) 0.0236(4) Uani 1 1 d . . . C20 C 0.90856(12) 0.11940(12) 0.52158(9) 0.0283(5) Uani 1 1 d . . . C21 C 0.88135(13) 0.08323(14) 0.46931(10) 0.0362(6) Uani 1 1 d . . . C22 C 0.82611(14) 0.11599(15) 0.44013(10) 0.0422(6) Uani 1 1 d . . . H22 H 0.8070 0.0910 0.4046 0.051 Uiso 1 1 calc R . . C23 C 0.79912(13) 0.18635(16) 0.46398(10) 0.0413(6) Uani 1 1 d . . . C24 C 0.82718(12) 0.22222(13) 0.51549(9) 0.0294(5) Uani 1 1 d . . . C25 C 0.86654(10) 0.27048(11) 0.65910(8) 0.0192(4) Uani 1 1 d . . . C26 C 0.88781(10) 0.32591(12) 0.70337(8) 0.0230(4) Uani 1 1 d . . . C27 C 0.84784(11) 0.34974(12) 0.75270(9) 0.0283(5) Uani 1 1 d . . . C28 C 0.78333(11) 0.31848(13) 0.76115(9) 0.0282(5) Uani 1 1 d . . . H28 H 0.7554 0.3346 0.7948 0.034 Uiso 1 1 calc R . . C29 C 0.76120(10) 0.26280(13) 0.71861(9) 0.0273(5) Uani 1 1 d . . . C30 C 0.80187(10) 0.23954(12) 0.66987(8) 0.0228(4) Uani 1 1 d . . . C31 C 0.98525(10) 0.20242(11) 0.63333(8) 0.0198(4) Uani 1 1 d . . . C32 C 0.97675(10) 0.13151(11) 0.66782(8) 0.0211(4) Uani 1 1 d . . . C33 C 1.02968(11) 0.09035(12) 0.69557(9) 0.0250(4) Uani 1 1 d . . . C34 C 1.09589(11) 0.11751(14) 0.69088(9) 0.0317(5) Uani 1 1 d . . . H34 H 1.1329 0.0891 0.7095 0.038 Uiso 1 1 calc R . . C35 C 1.10589(11) 0.18779(14) 0.65799(9) 0.0316(5) Uani 1 1 d . . . C36 C 1.05235(11) 0.22929(12) 0.63085(8) 0.0246(4) Uani 1 1 d . . . B1 B 0.91803(11) 0.24525(13) 0.60229(10) 0.0196(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0194(3) 0.0153(2) 0.0194(2) -0.00032(19) 0.00341(19) 0.0009(2) F1 0.0467(9) 0.0371(7) 0.0387(7) -0.0137(6) -0.0047(6) 0.0116(6) F2 0.0878(13) 0.0450(9) 0.0412(8) -0.0228(7) 0.0001(8) -0.0040(8) F3 0.0638(12) 0.0826(12) 0.0556(9) 0.0129(9) -0.0401(8) -0.0023(9) F4 0.0389(8) 0.0411(8) 0.0458(8) 0.0068(6) -0.0132(6) 0.0075(6) F5 0.0308(8) 0.0458(8) 0.0313(6) -0.0117(6) 0.0072(5) -0.0209(6) F6 0.0520(9) 0.0558(9) 0.0361(7) -0.0246(7) 0.0148(6) -0.0253(7) F7 0.0229(7) 0.0717(10) 0.0386(7) -0.0096(7) 0.0090(6) -0.0170(7) F8 0.0300(7) 0.0465(8) 0.0335(6) -0.0140(6) 0.0050(5) -0.0193(6) F9 0.0245(7) 0.0226(6) 0.0366(6) 0.0049(5) 0.0013(5) -0.0049(5) F10 0.0401(8) 0.0257(6) 0.0366(7) 0.0095(5) -0.0006(6) 0.0052(6) F11 0.0212(8) 0.0935(12) 0.0429(8) 0.0277(8) -0.0047(6) -0.0148(7) F12 0.0292(7) 0.0435(7) 0.0335(6) 0.0143(6) -0.0051(5) -0.0159(6) O1 0.0231(8) 0.0196(7) 0.0184(6) 0.0002(5) 0.0058(5) -0.0016(6) N2 0.0192(9) 0.0211(8) 0.0195(7) -0.0003(6) 0.0023(6) 0.0007(7) N1 0.0237(10) 0.0162(8) 0.0219(8) 0.0008(6) 0.0040(7) -0.0003(7) C1 0.0242(12) 0.0164(9) 0.0271(10) -0.0022(8) 0.0046(8) 0.0013(8) C2 0.0326(13) 0.0269(11) 0.0282(11) -0.0081(9) 0.0007(9) 0.0056(9) C3 0.0474(16) 0.0310(13) 0.0493(14) -0.0209(11) -0.0037(12) 0.0050(11) C4 0.0416(15) 0.0217(11) 0.0528(14) -0.0091(10) 0.0060(11) 0.0079(10) C5 0.0397(14) 0.0226(11) 0.0460(13) 0.0043(10) 0.0058(11) 0.0108(10) C6 0.0329(13) 0.0219(10) 0.0292(10) -0.0001(8) 0.0015(9) 0.0077(9) C7 0.0200(11) 0.0191(9) 0.0206(9) 0.0004(7) 0.0013(7) 0.0005(8) C8 0.0225(12) 0.0272(11) 0.0312(10) 0.0002(9) 0.0010(8) -0.0031(9) C9 0.0240(12) 0.0408(13) 0.0338(11) -0.0025(10) -0.0023(9) -0.0039(10) C10 0.0262(13) 0.0436(14) 0.0401(12) 0.0002(11) -0.0055(10) 0.0080(10) C11 0.0350(14) 0.0274(11) 0.0418(12) 0.0036(10) -0.0073(10) 0.0074(10) C12 0.0275(12) 0.0194(10) 0.0349(11) 0.0000(8) -0.0038(9) 0.0030(8) C13 0.0208(11) 0.0174(9) 0.0209(9) -0.0011(7) 0.0026(8) 0.0000(8) C14 0.0210(11) 0.0327(11) 0.0221(9) 0.0021(8) 0.0012(8) -0.0010(9) C15 0.0299(13) 0.0392(13) 0.0377(12) 0.0085(10) 0.0081(10) -0.0076(10) C16 0.0217(12) 0.0315(12) 0.0470(13) -0.0059(10) 0.0002(10) -0.0033(9) C17 0.0272(13) 0.0277(11) 0.0341(11) -0.0074(9) -0.0053(9) -0.0001(9) C18 0.0295(12) 0.0279(11) 0.0225(10) 0.0004(8) -0.0023(8) -0.0030(9) C19 0.0275(12) 0.0236(10) 0.0197(9) 0.0042(8) 0.0004(8) -0.0081(9) C20 0.0355(13) 0.0271(11) 0.0223(10) -0.0007(8) -0.0005(9) -0.0071(9) C21 0.0499(16) 0.0328(12) 0.0260(11) -0.0065(9) 0.0032(10) -0.0114(11) C22 0.0549(17) 0.0470(15) 0.0247(11) -0.0006(10) -0.0075(11) -0.0240(13) C23 0.0403(15) 0.0532(15) 0.0303(12) 0.0144(11) -0.0145(10) -0.0112(12) C24 0.0352(14) 0.0264(11) 0.0266(10) 0.0054(9) -0.0033(9) -0.0046(10) C25 0.0199(11) 0.0177(9) 0.0199(9) 0.0028(7) -0.0006(7) -0.0003(8) C26 0.0183(11) 0.0267(10) 0.0240(9) 0.0020(8) 0.0023(8) -0.0072(8) C27 0.0335(13) 0.0277(11) 0.0239(10) -0.0042(9) 0.0009(9) -0.0081(9) C28 0.0271(12) 0.0334(11) 0.0240(10) -0.0001(9) 0.0060(8) 0.0007(9) C29 0.0160(11) 0.0361(12) 0.0297(10) 0.0034(9) 0.0016(8) -0.0048(9) C30 0.0231(11) 0.0231(10) 0.0222(9) -0.0007(8) -0.0025(8) -0.0045(8) C31 0.0228(11) 0.0198(9) 0.0169(8) -0.0034(7) 0.0013(8) -0.0031(8) C32 0.0201(11) 0.0215(9) 0.0218(9) -0.0039(8) 0.0028(7) -0.0016(8) C33 0.0304(12) 0.0245(10) 0.0201(9) 0.0011(8) 0.0023(8) 0.0044(9) C34 0.0242(12) 0.0483(14) 0.0227(10) 0.0042(9) -0.0003(8) 0.0075(10) C35 0.0191(12) 0.0524(14) 0.0233(10) 0.0046(10) 0.0005(8) -0.0066(10) C36 0.0266(12) 0.0307(11) 0.0164(9) 0.0038(8) 0.0004(8) -0.0059(9) B1 0.0189(12) 0.0200(11) 0.0200(10) 0.0015(8) 0.0014(8) -0.0033(9) _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 1.7146(15) . ? P1 C13 1.8030(19) . ? P1 C7 1.8154(19) . ? P1 C1 1.8249(19) . ? F1 C20 1.343(2) . ? F2 C21 1.347(3) . ? F3 C23 1.350(3) . ? F4 C24 1.364(2) . ? F5 C26 1.352(2) . ? F6 C27 1.352(2) . ? F7 C29 1.351(2) . ? F8 C30 1.356(2) . ? F9 C32 1.356(2) . ? F10 C33 1.357(2) . ? F11 C35 1.351(2) . ? F12 C36 1.358(2) . ? O1 N2 1.3351(18) . ? O1 B1 1.551(2) . ? N2 N1 1.260(2) . ? C1 C6 1.538(3) . ? C1 C2 1.541(3) . ? C2 C3 1.530(3) . ? C3 C4 1.518(3) . ? C4 C5 1.521(3) . ? C5 C6 1.523(3) . ? C7 C12 1.536(3) . ? C7 C8 1.538(3) . ? C8 C9 1.529(3) . ? C9 C10 1.521(3) . ? C10 C11 1.518(3) . ? C11 C12 1.532(3) . ? C13 C14 1.535(3) . ? C13 C18 1.541(3) . ? C14 C15 1.531(3) . ? C15 C16 1.520(3) . ? C16 C17 1.515(3) . ? C17 C18 1.529(3) . ? C19 C24 1.382(3) . ? C19 C20 1.390(3) . ? C19 B1 1.645(3) . ? C20 C21 1.387(3) . ? C21 C22 1.360(3) . ? C22 C23 1.370(4) . ? C23 C24 1.378(3) . ? C25 C30 1.379(3) . ? C25 C26 1.387(3) . ? C25 B1 1.644(3) . ? C26 C27 1.382(3) . ? C27 C28 1.371(3) . ? C28 C29 1.369(3) . ? C29 C30 1.377(3) . ? C31 C36 1.382(3) . ? C31 C32 1.393(3) . ? C31 B1 1.633(3) . ? C32 C33 1.373(3) . ? C33 C34 1.370(3) . ? C34 C35 1.370(3) . ? C35 C36 1.379(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C13 102.24(8) . . ? N1 P1 C7 105.31(8) . . ? C13 P1 C7 110.74(9) . . ? N1 P1 C1 111.91(8) . . ? C13 P1 C1 117.13(9) . . ? C7 P1 C1 108.79(9) . . ? N2 O1 B1 110.32(13) . . ? N1 N2 O1 111.13(14) . . ? N2 N1 P1 111.10(12) . . ? C6 C1 C2 110.91(16) . . ? C6 C1 P1 113.50(13) . . ? C2 C1 P1 113.06(13) . . ? C3 C2 C1 109.94(18) . . ? C4 C3 C2 112.34(19) . . ? C3 C4 C5 111.10(19) . . ? C4 C5 C6 110.68(18) . . ? C5 C6 C1 110.13(18) . . ? C12 C7 C8 110.95(16) . . ? C12 C7 P1 113.06(13) . . ? C8 C7 P1 110.27(13) . . ? C9 C8 C7 110.98(17) . . ? C10 C9 C8 111.23(18) . . ? C11 C10 C9 110.98(18) . . ? C10 C11 C12 111.90(18) . . ? C11 C12 C7 110.98(17) . . ? C14 C13 C18 110.17(16) . . ? C14 C13 P1 114.45(13) . . ? C18 C13 P1 114.01(13) . . ? C15 C14 C13 109.58(16) . . ? C16 C15 C14 113.39(17) . . ? C17 C16 C15 111.06(18) . . ? C16 C17 C18 110.51(17) . . ? C17 C18 C13 108.53(16) . . ? C24 C19 C20 113.58(18) . . ? C24 C19 B1 119.28(18) . . ? C20 C19 B1 126.59(18) . . ? F1 C20 C21 115.45(19) . . ? F1 C20 C19 121.29(17) . . ? C21 C20 C19 123.2(2) . . ? F2 C21 C22 119.8(2) . . ? F2 C21 C20 119.2(2) . . ? C22 C21 C20 121.0(2) . . ? C21 C22 C23 117.4(2) . . ? F3 C23 C22 120.2(2) . . ? F3 C23 C24 118.8(2) . . ? C22 C23 C24 120.9(2) . . ? F4 C24 C23 117.3(2) . . ? F4 C24 C19 118.95(18) . . ? C23 C24 C19 123.8(2) . . ? C30 C25 C26 113.38(17) . . ? C30 C25 B1 126.39(17) . . ? C26 C25 B1 120.19(17) . . ? F5 C26 C27 116.78(17) . . ? F5 C26 C25 119.52(17) . . ? C27 C26 C25 123.69(18) . . ? F6 C27 C28 119.37(18) . . ? F6 C27 C26 119.57(19) . . ? C28 C27 C26 121.06(19) . . ? C29 C28 C27 116.63(19) . . ? F7 C29 C28 119.99(18) . . ? F7 C29 C30 118.50(18) . . ? C28 C29 C30 121.50(19) . . ? F8 C30 C29 115.43(17) . . ? F8 C30 C25 120.84(17) . . ? C29 C30 C25 123.73(18) . . ? C36 C31 C32 113.56(18) . . ? C36 C31 B1 127.38(17) . . ? C32 C31 B1 119.05(17) . . ? F9 C32 C33 117.51(17) . . ? F9 C32 C31 118.61(17) . . ? C33 C32 C31 123.86(18) . . ? F10 C33 C34 119.77(18) . . ? F10 C33 C32 119.14(18) . . ? C34 C33 C32 121.08(19) . . ? C33 C34 C35 116.52(19) . . ? F11 C35 C34 119.68(19) . . ? F11 C35 C36 118.27(19) . . ? C34 C35 C36 122.0(2) . . ? F12 C36 C35 116.05(18) . . ? F12 C36 C31 121.05(18) . . ? C35 C36 C31 122.90(19) . . ? O1 B1 C31 111.43(15) . . ? O1 B1 C25 103.81(14) . . ? C31 B1 C25 106.77(15) . . ? O1 B1 C19 105.09(14) . . ? C31 B1 C19 113.82(16) . . ? C25 B1 C19 115.51(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.395 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.054 data_C37H44BCl2F3OP_compound9 _database_code_depnum_ccdc_archive 'CCDC 786855' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C37 H47 B Cl F3 O P2' _chemical_formula_weight 672.95 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5346(5) _cell_length_b 21.1476(9) _cell_length_c 17.6877(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.6040(10) _cell_angle_gamma 90.00 _cell_volume 3480.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9953 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.74 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8561 _exptl_absorpt_correction_T_max 0.8971 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44879 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 30.95 _reflns_number_total 11037 _reflns_number_gt 8728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+1.1971P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11037 _refine_ls_number_parameters 432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.03882(3) 0.285272(14) 0.339144(17) 0.01520(7) Uani 1 1 d . . . F1 F -0.21461(9) 0.04974(4) 0.00113(5) 0.03022(18) Uani 1 1 d . . . F2 F 0.37509(12) 0.03838(5) 0.52865(5) 0.0436(2) Uani 1 1 d . . . F3 F 0.58408(9) 0.27134(5) 0.08718(5) 0.0365(2) Uani 1 1 d . . . O1 O 0.07347(9) 0.24461(4) 0.27438(5) 0.01777(16) Uani 1 1 d . . . C1 C 0.04438(12) 0.14809(5) 0.18384(7) 0.0171(2) Uani 1 1 d . . . C2 C -0.09053(13) 0.17067(6) 0.14600(7) 0.0219(2) Uani 1 1 d . . . H2 H -0.1231 0.2086 0.1626 0.026 Uiso 1 1 calc R . . C3 C -0.17854(14) 0.13857(6) 0.08426(7) 0.0238(2) Uani 1 1 d . . . H3 H -0.2672 0.1550 0.0596 0.029 Uiso 1 1 calc R . . C4 C -0.12994(14) 0.08203(6) 0.06114(7) 0.0214(2) Uani 1 1 d . . . C5 C 0.00179(15) 0.05697(6) 0.09574(7) 0.0232(2) Uani 1 1 d . . . H5 H 0.0325 0.0186 0.0793 0.028 Uiso 1 1 calc R . . C6 C 0.08749(14) 0.09075(6) 0.15607(7) 0.0209(2) Uani 1 1 d . . . H6 H 0.1774 0.0746 0.1790 0.025 Uiso 1 1 calc R . . C7 C 0.21772(13) 0.14249(5) 0.32801(7) 0.0183(2) Uani 1 1 d . . . C8 C 0.14844(14) 0.08765(6) 0.34575(7) 0.0227(2) Uani 1 1 d . . . H8 H 0.0658 0.0741 0.3113 0.027 Uiso 1 1 calc R . . C9 C 0.19872(17) 0.05259(6) 0.41308(8) 0.0274(3) Uani 1 1 d . . . H9 H 0.1496 0.0170 0.4241 0.033 Uiso 1 1 calc R . . C10 C 0.32325(16) 0.07231(7) 0.46270(8) 0.0284(3) Uani 1 1 d . . . C11 C 0.39772(14) 0.12527(7) 0.44893(7) 0.0265(3) Uani 1 1 d . . . H11 H 0.4816 0.1376 0.4833 0.032 Uiso 1 1 calc R . . C12 C 0.34328(13) 0.15980(6) 0.38173(7) 0.0214(2) Uani 1 1 d . . . H12 H 0.3923 0.1959 0.3721 0.026 Uiso 1 1 calc R . . C13 C 0.28395(12) 0.21277(6) 0.21207(6) 0.0175(2) Uani 1 1 d . . . C14 C 0.41199(13) 0.17971(6) 0.21448(7) 0.0202(2) Uani 1 1 d . . . H14 H 0.4295 0.1433 0.2445 0.024 Uiso 1 1 calc R . . C15 C 0.51450(13) 0.19907(7) 0.17384(7) 0.0238(2) Uani 1 1 d . . . H15 H 0.5988 0.1762 0.1765 0.029 Uiso 1 1 calc R . . C16 C 0.48683(14) 0.25303(7) 0.12968(7) 0.0248(3) Uani 1 1 d . . . C17 C 0.36426(15) 0.28850(7) 0.12527(8) 0.0263(3) Uani 1 1 d . . . H17 H 0.3488 0.3252 0.0957 0.032 Uiso 1 1 calc R . . C18 C 0.26395(14) 0.26773(6) 0.16657(7) 0.0224(2) Uani 1 1 d . . . H18 H 0.1806 0.2912 0.1638 0.027 Uiso 1 1 calc R . . C19 C 0.19984(12) 0.31715(6) 0.40170(7) 0.0182(2) Uani 1 1 d . . . H19 H 0.2476 0.2820 0.4333 0.022 Uiso 1 1 calc R . . C20 C 0.30630(14) 0.34250(7) 0.35498(8) 0.0256(3) Uani 1 1 d . . . H20A H 0.3285 0.3094 0.3214 0.031 Uiso 1 1 calc R . . H20B H 0.2630 0.3775 0.3227 0.031 Uiso 1 1 calc R . . C21 C 0.44441(15) 0.36468(8) 0.40971(10) 0.0344(3) Uani 1 1 d . . . H21A H 0.5090 0.3821 0.3796 0.041 Uiso 1 1 calc R . . H21B H 0.4917 0.3288 0.4386 0.041 Uiso 1 1 calc R . . C22 C 0.41363(16) 0.41476(7) 0.46624(10) 0.0343(3) Uani 1 1 d . . . H22A H 0.5025 0.4262 0.5019 0.041 Uiso 1 1 calc R . . H22B H 0.3754 0.4524 0.4377 0.041 Uiso 1 1 calc R . . C23 C 0.30666(15) 0.39054(7) 0.51164(8) 0.0277(3) Uani 1 1 d . . . H23A H 0.2846 0.4241 0.5446 0.033 Uiso 1 1 calc R . . H23B H 0.3495 0.3559 0.5447 0.033 Uiso 1 1 calc R . . C24 C 0.16752(13) 0.36780(6) 0.45802(7) 0.0220(2) Uani 1 1 d . . . H24A H 0.1190 0.4033 0.4288 0.026 Uiso 1 1 calc R . . H24B H 0.1041 0.3503 0.4888 0.026 Uiso 1 1 calc R . . C25 C -0.07013(13) 0.35157(5) 0.29233(7) 0.0184(2) Uani 1 1 d . . . H25 H -0.0033 0.3863 0.2897 0.022 Uiso 1 1 calc R . . C26 C -0.17987(14) 0.37704(6) 0.33709(7) 0.0233(2) Uani 1 1 d . . . H26A H -0.2511 0.3448 0.3394 0.028 Uiso 1 1 calc R . . H26B H -0.1312 0.3875 0.3897 0.028 Uiso 1 1 calc R . . C27 C -0.25405(15) 0.43594(6) 0.29697(9) 0.0290(3) Uani 1 1 d . . . H27A H -0.3238 0.4512 0.3252 0.035 Uiso 1 1 calc R . . H27B H -0.1832 0.4690 0.2976 0.035 Uiso 1 1 calc R . . C28 C -0.32976(15) 0.42209(7) 0.21338(9) 0.0290(3) Uani 1 1 d . . . H28A H -0.4069 0.3921 0.2127 0.035 Uiso 1 1 calc R . . H28B H -0.3714 0.4607 0.1887 0.035 Uiso 1 1 calc R . . C29 C -0.22396(16) 0.39510(7) 0.16865(8) 0.0289(3) Uani 1 1 d . . . H29A H -0.1535 0.4272 0.1641 0.035 Uiso 1 1 calc R . . H29B H -0.2751 0.3839 0.1168 0.035 Uiso 1 1 calc R . . C30 C -0.14664(15) 0.33673(6) 0.20840(7) 0.0233(2) Uani 1 1 d . . . H30A H -0.0767 0.3223 0.1798 0.028 Uiso 1 1 calc R . . H30B H -0.2157 0.3030 0.2082 0.028 Uiso 1 1 calc R . . C31 C -0.06374(13) 0.24262(6) 0.39832(7) 0.0188(2) Uani 1 1 d . . . H31 H -0.1162 0.2744 0.4216 0.023 Uiso 1 1 calc R . . C32 C -0.17729(14) 0.20117(6) 0.34528(7) 0.0238(2) Uani 1 1 d . . . H32A H -0.2385 0.2277 0.3070 0.029 Uiso 1 1 calc R . . H32B H -0.1295 0.1710 0.3181 0.029 Uiso 1 1 calc R . . C33 C -0.26942(15) 0.16564(7) 0.39204(8) 0.0298(3) Uani 1 1 d . . . H33A H -0.3246 0.1957 0.4151 0.036 Uiso 1 1 calc R . . H33B H -0.3364 0.1383 0.3578 0.036 Uiso 1 1 calc R . . C34 C -0.17577(16) 0.12610(7) 0.45568(8) 0.0306(3) Uani 1 1 d . . . H34A H -0.1245 0.0944 0.4326 0.037 Uiso 1 1 calc R . . H34B H -0.2359 0.1045 0.4852 0.037 Uiso 1 1 calc R . . C35 C -0.06831(16) 0.16846(7) 0.50956(8) 0.0284(3) Uani 1 1 d . . . H35A H -0.0088 0.1427 0.5494 0.034 Uiso 1 1 calc R . . H35B H -0.1201 0.1984 0.5348 0.034 Uiso 1 1 calc R . . C36 C 0.02782(14) 0.20461(6) 0.46536(7) 0.0222(2) Uani 1 1 d . . . H36A H 0.0879 0.1750 0.4450 0.027 Uiso 1 1 calc R . . H36B H 0.0901 0.2331 0.5005 0.027 Uiso 1 1 calc R . . C37 C 0.3083(2) 0.48789(11) 0.19699(14) 0.0527(5) Uani 1 1 d . . . CL1 P 0.2720(2) 0.53945(13) 0.27196(16) 0.0522(4) Uani 0.50 1 d P . . CL2 P 0.1529(4) 0.44850(16) 0.1514(2) 0.0561(7) Uani 0.50 1 d P . . B1 B 0.15700(14) 0.18526(6) 0.25152(7) 0.0163(2) Uani 1 1 d . . . Cl1A Cl 0.3259(4) 0.53220(13) 0.27691(17) 0.1129(11) Uani 0.50 1 d P . . Cl2A Cl 0.1423(4) 0.45422(15) 0.1641(2) 0.0672(9) Uani 0.50 1 d P . . H44 H 0.338(3) 0.5135(13) 0.1545(16) 0.084(8) Uiso 1 1 d . . . H43 H 0.379(4) 0.4473(18) 0.221(2) 0.141(14) Uiso 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 0.01399(13) 0.01630(13) 0.01525(13) -0.00145(10) 0.00307(10) 0.00043(10) F1 0.0298(4) 0.0335(4) 0.0247(4) -0.0098(3) 0.0004(3) -0.0085(3) F2 0.0528(6) 0.0502(6) 0.0263(4) 0.0180(4) 0.0057(4) 0.0147(5) F3 0.0242(4) 0.0542(6) 0.0343(5) 0.0077(4) 0.0134(4) -0.0073(4) O1 0.0174(4) 0.0184(4) 0.0176(4) -0.0025(3) 0.0040(3) 0.0025(3) C1 0.0174(5) 0.0174(5) 0.0173(5) -0.0003(4) 0.0054(4) -0.0004(4) C2 0.0200(5) 0.0222(6) 0.0231(6) -0.0044(4) 0.0037(5) 0.0026(4) C3 0.0174(5) 0.0285(6) 0.0239(6) -0.0033(5) 0.0009(5) 0.0010(5) C4 0.0227(6) 0.0237(6) 0.0176(5) -0.0032(4) 0.0039(4) -0.0070(5) C5 0.0280(6) 0.0184(5) 0.0232(6) -0.0037(4) 0.0055(5) 0.0010(5) C6 0.0210(5) 0.0189(5) 0.0216(5) -0.0004(4) 0.0019(4) 0.0030(4) C7 0.0184(5) 0.0191(5) 0.0180(5) -0.0010(4) 0.0053(4) 0.0026(4) C8 0.0271(6) 0.0206(5) 0.0206(5) -0.0007(4) 0.0053(5) -0.0003(5) C9 0.0392(8) 0.0206(6) 0.0244(6) 0.0032(5) 0.0110(6) 0.0021(5) C10 0.0356(7) 0.0317(7) 0.0184(6) 0.0067(5) 0.0072(5) 0.0116(6) C11 0.0210(6) 0.0392(7) 0.0185(5) 0.0008(5) 0.0026(5) 0.0063(5) C12 0.0182(5) 0.0269(6) 0.0195(5) -0.0010(4) 0.0050(4) 0.0021(5) C13 0.0168(5) 0.0200(5) 0.0149(5) -0.0013(4) 0.0020(4) -0.0005(4) C14 0.0188(5) 0.0239(6) 0.0177(5) 0.0004(4) 0.0035(4) 0.0021(4) C15 0.0159(5) 0.0341(7) 0.0213(6) -0.0024(5) 0.0040(4) 0.0012(5) C16 0.0183(5) 0.0370(7) 0.0199(5) -0.0013(5) 0.0062(4) -0.0078(5) C17 0.0266(6) 0.0284(6) 0.0241(6) 0.0053(5) 0.0060(5) -0.0029(5) C18 0.0200(6) 0.0240(6) 0.0230(6) 0.0028(5) 0.0044(5) 0.0014(5) C19 0.0156(5) 0.0191(5) 0.0189(5) -0.0028(4) 0.0016(4) -0.0006(4) C20 0.0189(6) 0.0310(6) 0.0275(6) -0.0056(5) 0.0064(5) -0.0052(5) C21 0.0181(6) 0.0395(8) 0.0455(9) -0.0131(7) 0.0068(6) -0.0066(6) C22 0.0233(6) 0.0330(7) 0.0439(8) -0.0140(6) 0.0013(6) -0.0071(6) C23 0.0261(6) 0.0287(6) 0.0243(6) -0.0084(5) -0.0035(5) 0.0006(5) C24 0.0199(5) 0.0240(6) 0.0209(5) -0.0061(4) 0.0021(4) -0.0001(5) C25 0.0167(5) 0.0174(5) 0.0211(5) -0.0007(4) 0.0039(4) 0.0013(4) C26 0.0217(6) 0.0247(6) 0.0237(6) -0.0038(5) 0.0051(5) 0.0056(5) C27 0.0266(6) 0.0220(6) 0.0384(7) -0.0040(5) 0.0073(6) 0.0067(5) C28 0.0230(6) 0.0250(6) 0.0373(7) 0.0049(5) 0.0028(5) 0.0066(5) C29 0.0303(7) 0.0288(6) 0.0268(6) 0.0077(5) 0.0041(5) 0.0083(5) C30 0.0257(6) 0.0244(6) 0.0186(5) 0.0007(4) 0.0025(5) 0.0067(5) C31 0.0173(5) 0.0223(5) 0.0171(5) 0.0001(4) 0.0043(4) -0.0004(4) C32 0.0193(6) 0.0306(6) 0.0205(5) 0.0031(5) 0.0021(4) -0.0060(5) C33 0.0222(6) 0.0363(7) 0.0309(7) 0.0048(6) 0.0060(5) -0.0077(5) C34 0.0320(7) 0.0320(7) 0.0297(7) 0.0066(5) 0.0105(6) -0.0055(6) C35 0.0321(7) 0.0344(7) 0.0195(6) 0.0059(5) 0.0074(5) -0.0001(6) C36 0.0216(6) 0.0266(6) 0.0176(5) 0.0016(4) 0.0025(4) 0.0000(5) C37 0.0386(10) 0.0584(12) 0.0636(13) -0.0132(10) 0.0167(9) -0.0040(9) CL1 0.0596(7) 0.0550(8) 0.0436(7) -0.0128(5) 0.0145(6) 0.0142(6) CL2 0.0457(12) 0.0482(9) 0.0769(12) -0.0226(8) 0.0193(8) -0.0213(8) B1 0.0155(5) 0.0165(5) 0.0168(5) -0.0010(4) 0.0038(4) 0.0016(4) Cl1A 0.225(3) 0.0610(13) 0.0668(13) -0.0187(10) 0.062(2) -0.0484(18) Cl2A 0.0391(8) 0.0691(15) 0.0894(19) 0.0253(14) 0.0052(11) 0.0021(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5251(8) . ? P1 C19 1.8151(12) . ? P1 C31 1.8199(12) . ? P1 C25 1.8318(12) . ? F1 C4 1.3679(14) . ? F2 C10 1.3669(15) . ? F3 C16 1.3708(14) . ? O1 B1 1.5854(15) . ? C1 C2 1.3981(17) . ? C1 C6 1.4033(16) . ? C1 B1 1.6256(17) . ? C2 C3 1.3992(17) . ? C2 H2 0.9300 . ? C3 C4 1.3765(18) . ? C3 H3 0.9300 . ? C4 C5 1.3774(19) . ? C5 C6 1.3915(17) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.4036(17) . ? C7 C12 1.4049(17) . ? C7 B1 1.6255(17) . ? C8 C9 1.3959(18) . ? C8 H8 0.9300 . ? C9 C10 1.378(2) . ? C9 H9 0.9300 . ? C10 C11 1.376(2) . ? C11 C12 1.3951(18) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.3993(16) . ? C13 C18 1.4027(17) . ? C13 B1 1.6307(17) . ? C14 C15 1.3951(17) . ? C14 H14 0.9300 . ? C15 C16 1.3753(19) . ? C15 H15 0.9300 . ? C16 C17 1.3765(19) . ? C17 C18 1.3951(18) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.5383(17) . ? C19 C24 1.5391(16) . ? C19 H19 0.9800 . ? C20 C21 1.5279(19) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.528(2) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.518(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.5303(18) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C30 1.5367(17) . ? C25 C26 1.5405(17) . ? C25 H25 0.9800 . ? C26 C27 1.5285(18) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.525(2) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.522(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.5281(18) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C36 1.5370(17) . ? C31 C32 1.5419(17) . ? C31 H31 0.9800 . ? C32 C33 1.5288(18) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.525(2) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.528(2) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.5325(18) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 Cl1A 1.674(3) . ? C37 Cl2A 1.717(4) . ? C37 CL2 1.737(4) . ? C37 CL1 1.808(3) . ? C37 H44 1.02(3) . ? C37 H43 1.11(4) . ? CL1 Cl1A 0.526(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 O1 P1 C19 111.97(5) . . ? O1 P1 C31 112.59(5) . . ? C19 P1 C31 108.82(5) . . ? O1 P1 C25 106.65(5) . . ? C19 P1 C25 108.18(5) . . ? C31 P1 C25 108.45(5) . . ? P1 O1 B1 147.26(8) . . ? C2 C1 C6 115.89(11) . . ? C2 C1 B1 125.33(10) . . ? C6 C1 B1 118.60(10) . . ? C1 C2 C3 122.71(11) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 118.02(12) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? F1 C4 C3 118.96(11) . . ? F1 C4 C5 118.64(11) . . ? C3 C4 C5 122.39(11) . . ? C4 C5 C6 117.98(11) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 122.98(11) . . ? C5 C6 H6 118.5 . . ? C1 C6 H6 118.5 . . ? C8 C7 C12 115.93(11) . . ? C8 C7 B1 123.12(11) . . ? C12 C7 B1 120.94(10) . . ? C9 C8 C7 122.60(12) . . ? C9 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C10 C9 C8 118.06(13) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? F2 C10 C11 118.29(13) . . ? F2 C10 C9 119.04(13) . . ? C11 C10 C9 122.67(12) . . ? C10 C11 C12 117.81(12) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C11 C12 C7 122.92(12) . . ? C11 C12 H12 118.5 . . ? C7 C12 H12 118.5 . . ? C14 C13 C18 116.10(11) . . ? C14 C13 B1 122.19(10) . . ? C18 C13 B1 121.36(10) . . ? C15 C14 C13 122.84(12) . . ? C15 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C16 C15 C14 117.84(12) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? F3 C16 C15 118.49(12) . . ? F3 C16 C17 118.85(12) . . ? C15 C16 C17 122.65(12) . . ? C16 C17 C18 117.99(12) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? C17 C18 C13 122.57(12) . . ? C17 C18 H18 118.7 . . ? C13 C18 H18 118.7 . . ? C20 C19 C24 110.74(10) . . ? C20 C19 P1 111.81(8) . . ? C24 C19 P1 113.01(8) . . ? C20 C19 H19 107.0 . . ? C24 C19 H19 107.0 . . ? P1 C19 H19 107.0 . . ? C21 C20 C19 110.19(11) . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C20 C21 C22 111.42(12) . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 111.06(12) . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C24 111.70(11) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C19 110.54(10) . . ? C23 C24 H24A 109.5 . . ? C19 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C30 C25 C26 109.60(10) . . ? C30 C25 P1 112.53(8) . . ? C26 C25 P1 114.65(8) . . ? C30 C25 H25 106.5 . . ? C26 C25 H25 106.5 . . ? P1 C25 H25 106.5 . . ? C27 C26 C25 110.10(11) . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.2 . . ? C28 C27 C26 111.51(11) . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? C26 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C29 C28 C27 110.40(11) . . ? C29 C28 H28A 109.6 . . ? C27 C28 H28A 109.6 . . ? C29 C28 H28B 109.6 . . ? C27 C28 H28B 109.6 . . ? H28A C28 H28B 108.1 . . ? C28 C29 C30 111.81(11) . . ? C28 C29 H29A 109.3 . . ? C30 C29 H29A 109.3 . . ? C28 C29 H29B 109.3 . . ? C30 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? C29 C30 C25 111.05(11) . . ? C29 C30 H30A 109.4 . . ? C25 C30 H30A 109.4 . . ? C29 C30 H30B 109.4 . . ? C25 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C36 C31 C32 112.17(10) . . ? C36 C31 P1 114.64(8) . . ? C32 C31 P1 109.02(8) . . ? C36 C31 H31 106.9 . . ? C32 C31 H31 106.9 . . ? P1 C31 H31 106.9 . . ? C33 C32 C31 111.12(10) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C34 C33 C32 110.84(11) . . ? C34 C33 H33A 109.5 . . ? C32 C33 H33A 109.5 . . ? C34 C33 H33B 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C33 C34 C35 110.12(12) . . ? C33 C34 H34A 109.6 . . ? C35 C34 H34A 109.6 . . ? C33 C34 H34B 109.6 . . ? C35 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C34 C35 C36 111.63(11) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 110.62(10) . . ? C35 C36 H36A 109.5 . . ? C31 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 108.1 . . ? Cl1A C37 Cl2A 115.7(2) . . ? Cl1A C37 CL2 125.4(2) . . ? Cl2A C37 CL2 9.7(3) . . ? Cl1A C37 CL1 16.80(15) . . ? Cl2A C37 CL1 100.88(19) . . ? CL2 C37 CL1 110.45(19) . . ? Cl1A C37 H44 109.4(15) . . ? Cl2A C37 H44 111.0(16) . . ? CL2 C37 H44 105.2(16) . . ? CL1 C37 H44 110.5(15) . . ? Cl1A C37 H43 100(2) . . ? Cl2A C37 H43 104.1(19) . . ? CL2 C37 H43 100.9(19) . . ? CL1 C37 H43 113(2) . . ? H44 C37 H43 116(2) . . ? Cl1A CL1 C37 67.0(5) . . ? O1 B1 C7 109.61(9) . . ? O1 B1 C1 106.42(9) . . ? C7 B1 C1 113.70(10) . . ? O1 B1 C13 106.73(9) . . ? C7 B1 C13 113.07(9) . . ? C1 B1 C13 106.87(9) . . ? CL1 Cl1A C37 96.2(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.95 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.747 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.055 data_C55H42BF20N2OP_Compound10 _database_code_depnum_ccdc_archive 'CCDC 786856' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C55 H42 B F20 N2 O P' _chemical_formula_weight 1168.69 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 0.500 0.000 1.000 232 70 ' ' _platon_squeeze_details ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.3838(3) _cell_length_b 12.5415(3) _cell_length_c 18.4913(5) _cell_angle_alpha 94.7030(10) _cell_angle_beta 103.5460(10) _cell_angle_gamma 101.7340(10) _cell_volume 2708.21(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9902 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 28.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6711 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51443 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.50 _reflns_number_total 13665 _reflns_number_gt 9650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.0857P] 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 13665 _refine_ls_number_parameters 730 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.80697(3) 0.76416(3) 0.31326(2) 0.02081(9) Uani 1 1 d . . . F1 F 0.19106(8) 0.07682(8) 0.19789(5) 0.0302(2) Uani 1 1 d . . . F2 F 0.15752(9) 0.07875(10) 0.05019(5) 0.0463(3) Uani 1 1 d . . . F3 F 0.32198(10) 0.19872(10) -0.00585(5) 0.0486(3) Uani 1 1 d . . . F4 F 0.51562(9) 0.32224(9) 0.09081(6) 0.0434(3) Uani 1 1 d . . . F5 F 0.54780(8) 0.32954(8) 0.23647(5) 0.0315(2) Uani 1 1 d . . . F6 F 0.59757(8) 0.14916(8) 0.30024(5) 0.0312(2) Uani 1 1 d . . . F7 F 0.80716(8) 0.24332(9) 0.38290(6) 0.0432(3) Uani 1 1 d . . . F8 F 0.84087(9) 0.40258(10) 0.50089(6) 0.0481(3) Uani 1 1 d . . . F9 F 0.65672(9) 0.45846(8) 0.53629(5) 0.0409(3) Uani 1 1 d . . . F10 F 0.44798(8) 0.36582(8) 0.45687(5) 0.0305(2) Uani 1 1 d . . . F11 F 0.37997(8) 0.41845(7) 0.30474(5) 0.0288(2) Uani 1 1 d . . . F12 F 0.21322(9) 0.52055(8) 0.31336(6) 0.0395(2) Uani 1 1 d . . . F13 F 0.02555(9) 0.41503(10) 0.35442(7) 0.0496(3) Uani 1 1 d . . . F14 F 0.00484(8) 0.20026(9) 0.37773(7) 0.0501(3) Uani 1 1 d . . . F15 F 0.15846(8) 0.09293(8) 0.35823(6) 0.0341(2) Uani 1 1 d . . . F16 F 0.36639(8) 0.12792(8) 0.46085(5) 0.0304(2) Uani 1 1 d . . . F17 F 0.35371(10) -0.07095(9) 0.50398(5) 0.0421(3) Uani 1 1 d . . . F18 F 0.35837(10) -0.24522(8) 0.40668(6) 0.0456(3) Uani 1 1 d . . . F19 F 0.37759(8) -0.21429(7) 0.26629(5) 0.0338(2) Uani 1 1 d . . . F20 F 0.38910(8) -0.01929(7) 0.22161(5) 0.0273(2) Uani 1 1 d . . . O1 O 0.74977(9) 0.60024(9) 0.12394(5) 0.0232(2) Uani 1 1 d . . . N1 N 0.74788(11) 0.69770(10) 0.22306(7) 0.0230(3) Uani 1 1 d . . . N2 N 0.81061(11) 0.65143(10) 0.19459(7) 0.0217(3) Uani 1 1 d . . . C2 C 0.93668(13) 0.63996(13) 0.09710(8) 0.0232(3) Uani 1 1 d . . . C3 C 1.04262(14) 0.61890(15) 0.12594(9) 0.0302(4) Uani 1 1 d . . . H2 H 1.0482 0.5495 0.1384 0.036 Uiso 1 1 calc R . . C4 C 1.14138(15) 0.70184(16) 0.13643(10) 0.0393(4) Uani 1 1 d . . . H3 H 1.2124 0.6868 0.1550 0.047 Uiso 1 1 calc R . . C5 C 1.13471(16) 0.80511(17) 0.11968(11) 0.0417(5) Uani 1 1 d . . . H4 H 1.2008 0.8599 0.1270 0.050 Uiso 1 1 calc R . . C6 C 1.02878(16) 0.82743(16) 0.09177(10) 0.0383(4) Uani 1 1 d . . . H5 H 1.0235 0.8975 0.0807 0.046 Uiso 1 1 calc R . . C7 C 0.93093(15) 0.74515(14) 0.08041(9) 0.0299(4) Uani 1 1 d . . . H6 H 0.8601 0.7604 0.0613 0.036 Uiso 1 1 calc R . . C1 C 0.82501(13) 0.55321(12) 0.08398(8) 0.0212(3) Uani 1 1 d . . . C8 C 0.75398(13) 0.53217(12) 0.00240(8) 0.0216(3) Uani 1 1 d . . . C9 C 0.80020(14) 0.56547(14) -0.05603(8) 0.0269(3) Uani 1 1 d . . . H9 H 0.8758 0.6043 -0.0456 0.032 Uiso 1 1 calc R . . C10 C 0.73447(15) 0.54122(15) -0.12980(9) 0.0316(4) Uani 1 1 d . . . H10 H 0.7662 0.5638 -0.1685 0.038 Uiso 1 1 calc R . . C11 C 0.62204(15) 0.48364(15) -0.14598(9) 0.0330(4) Uani 1 1 d . . . H11 H 0.5780 0.4674 -0.1954 0.040 Uiso 1 1 calc R . . C12 C 0.57577(15) 0.45058(16) -0.08856(10) 0.0377(4) Uani 1 1 d . . . H12 H 0.5000 0.4121 -0.0993 0.045 Uiso 1 1 calc R . . C13 C 0.64112(15) 0.47415(14) -0.01472(9) 0.0323(4) Uani 1 1 d . . . H13 H 0.6090 0.4509 0.0236 0.039 Uiso 1 1 calc R . . C14 C 0.84076(13) 0.44406(13) 0.11079(8) 0.0244(3) Uani 1 1 d . . . C15 C 0.88970(15) 0.37741(14) 0.07034(9) 0.0319(4) Uani 1 1 d . . . H15 H 0.9077 0.3984 0.0267 0.038 Uiso 1 1 calc R . . C16 C 0.91183(18) 0.28060(16) 0.09401(11) 0.0428(5) Uani 1 1 d . . . H16 H 0.9463 0.2380 0.0671 0.051 Uiso 1 1 calc R . . C17 C 0.8827(2) 0.24700(17) 0.15776(11) 0.0500(5) Uani 1 1 d . . . H17 H 0.8988 0.1826 0.1744 0.060 Uiso 1 1 calc R . . C18 C 0.8298(2) 0.30962(17) 0.19629(11) 0.0501(5) Uani 1 1 d . . . H18 H 0.8077 0.2860 0.2381 0.060 Uiso 1 1 calc R . . C19 C 0.80897(16) 0.40778(15) 0.17332(9) 0.0359(4) Uani 1 1 d . . . H19 H 0.7735 0.4496 0.2000 0.043 Uiso 1 1 calc R . . C20 C 0.71987(14) 0.67427(14) 0.36537(9) 0.0285(4) Uani 1 1 d . . . C21 C 0.59679(16) 0.68985(17) 0.34961(11) 0.0417(5) Uani 1 1 d . . . H21A H 0.5527 0.6379 0.3730 0.063 Uiso 1 1 calc R . . H21B H 0.5634 0.6782 0.2964 0.063 Uiso 1 1 calc R . . H21C H 0.5975 0.7631 0.3696 0.063 Uiso 1 1 calc R . . C22 C 0.70977(19) 0.55328(14) 0.33593(10) 0.0417(5) Uani 1 1 d . . . H22A H 0.7846 0.5389 0.3437 0.063 Uiso 1 1 calc R . . H22B H 0.6722 0.5391 0.2833 0.063 Uiso 1 1 calc R . . H22C H 0.6662 0.5063 0.3625 0.063 Uiso 1 1 calc R . . C23 C 0.77289(17) 0.69757(17) 0.45079(9) 0.0397(4) Uani 1 1 d . . . H23A H 0.7231 0.6549 0.4758 0.060 Uiso 1 1 calc R . . H23B H 0.7832 0.7743 0.4676 0.060 Uiso 1 1 calc R . . H23C H 0.8455 0.6781 0.4622 0.060 Uiso 1 1 calc R . . C24 C 0.96426(14) 0.77292(15) 0.34611(9) 0.0314(4) Uani 1 1 d . . . C25 C 0.98597(17) 0.65840(18) 0.35798(11) 0.0454(5) Uani 1 1 d . . . H25A H 1.0667 0.6631 0.3721 0.068 Uiso 1 1 calc R . . H25B H 0.9518 0.6088 0.3122 0.068 Uiso 1 1 calc R . . H25C H 0.9530 0.6319 0.3970 0.068 Uiso 1 1 calc R . . C26 C 1.01640(17) 0.85297(19) 0.42035(10) 0.0477(5) Uani 1 1 d . . . H26A H 0.9770 0.8295 0.4573 0.072 Uiso 1 1 calc R . . H26B H 1.0087 0.9258 0.4115 0.072 Uiso 1 1 calc R . . H26C H 1.0958 0.8532 0.4382 0.072 Uiso 1 1 calc R . . C27 C 1.02903(15) 0.81505(17) 0.28778(10) 0.0399(4) Uani 1 1 d . . . H27A H 1.1085 0.8160 0.3060 0.060 Uiso 1 1 calc R . . H27B H 1.0205 0.8880 0.2803 0.060 Uiso 1 1 calc R . . H27C H 0.9981 0.7671 0.2410 0.060 Uiso 1 1 calc R . . C28 C 0.76920(16) 0.90014(13) 0.30415(10) 0.0331(4) Uani 1 1 d . . . C29 C 0.7721(2) 0.95836(16) 0.38170(12) 0.0513(5) Uani 1 1 d . . . H29A H 0.8469 0.9684 0.4147 0.077 Uiso 1 1 calc R . . H29B H 0.7170 0.9142 0.4024 0.077 Uiso 1 1 calc R . . H29C H 0.7541 1.0287 0.3762 0.077 Uiso 1 1 calc R . . C30 C 0.85346(19) 0.97394(16) 0.26999(12) 0.0492(5) Uani 1 1 d . . . H30A H 0.8276 1.0396 0.2596 0.074 Uiso 1 1 calc R . . H30B H 0.8580 0.9352 0.2242 0.074 Uiso 1 1 calc R . . H30C H 0.9275 0.9932 0.3048 0.074 Uiso 1 1 calc R . . C31 C 0.65022(18) 0.88589(17) 0.25001(12) 0.0474(5) Uani 1 1 d . . . H31A H 0.6320 0.9564 0.2465 0.071 Uiso 1 1 calc R . . H31B H 0.5943 0.8391 0.2686 0.071 Uiso 1 1 calc R . . H31C H 0.6503 0.8532 0.2012 0.071 Uiso 1 1 calc R . . C32 C 0.37298(13) 0.19902(12) 0.22610(8) 0.0206(3) Uani 1 1 d . . . C33 C 0.27442(13) 0.14032(13) 0.17367(8) 0.0242(3) Uani 1 1 d . . . C34 C 0.25518(15) 0.13908(14) 0.09711(9) 0.0309(4) Uani 1 1 d . . . C35 C 0.33753(15) 0.19950(15) 0.06856(9) 0.0330(4) Uani 1 1 d . . . C36 C 0.43477(15) 0.26101(14) 0.11748(9) 0.0296(4) Uani 1 1 d . . . C37 C 0.44988(13) 0.26112(12) 0.19387(9) 0.0241(3) Uani 1 1 d . . . C38 C 0.51039(12) 0.25616(12) 0.37075(8) 0.0197(3) Uani 1 1 d . . . C39 C 0.60790(13) 0.22719(12) 0.35803(8) 0.0235(3) Uani 1 1 d . . . C40 C 0.71744(13) 0.27417(14) 0.40008(10) 0.0289(4) Uani 1 1 d . . . C41 C 0.73449(14) 0.35342(14) 0.45976(9) 0.0304(4) Uani 1 1 d . . . C42 C 0.64167(14) 0.38275(13) 0.47729(8) 0.0275(3) Uani 1 1 d . . . C43 C 0.53328(13) 0.33329(12) 0.43364(8) 0.0226(3) Uani 1 1 d . . . C44 C 0.28070(12) 0.25051(12) 0.33157(8) 0.0205(3) Uani 1 1 d . . . C45 C 0.28547(13) 0.35968(13) 0.32079(8) 0.0232(3) Uani 1 1 d . . . C46 C 0.20192(15) 0.41513(13) 0.32577(9) 0.0284(4) Uani 1 1 d . . . C47 C 0.10650(14) 0.36216(15) 0.34566(9) 0.0333(4) Uani 1 1 d . . . C48 C 0.09642(14) 0.25462(15) 0.35711(10) 0.0321(4) Uani 1 1 d . . . C49 C 0.18092(13) 0.20076(13) 0.34857(9) 0.0254(3) Uani 1 1 d . . . C50 C 0.37204(12) 0.06556(12) 0.33738(8) 0.0192(3) Uani 1 1 d . . . C51 C 0.36694(13) 0.04443(13) 0.40952(8) 0.0227(3) Uani 1 1 d . . . C52 C 0.36148(14) -0.05724(14) 0.43344(9) 0.0277(3) Uani 1 1 d . . . C53 C 0.36403(14) -0.14530(13) 0.38518(9) 0.0296(4) Uani 1 1 d . . . C54 C 0.37309(13) -0.12931(12) 0.31395(9) 0.0249(3) Uani 1 1 d . . . C55 C 0.37739(12) -0.02613(12) 0.29198(8) 0.0214(3) Uani 1 1 d . . . B1 B 0.38397(14) 0.19250(13) 0.31663(9) 0.0193(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 0.0232(2) 0.02025(19) 0.01945(17) 0.00194(14) 0.00690(15) 0.00470(15) F1 0.0231(5) 0.0328(5) 0.0306(5) 0.0080(4) 0.0052(4) -0.0027(4) F2 0.0388(6) 0.0594(7) 0.0278(5) 0.0061(5) -0.0048(4) -0.0026(5) F3 0.0518(7) 0.0747(8) 0.0244(5) 0.0180(5) 0.0120(5) 0.0191(6) F4 0.0435(6) 0.0536(7) 0.0427(6) 0.0239(5) 0.0263(5) 0.0087(5) F5 0.0277(5) 0.0297(5) 0.0343(5) 0.0069(4) 0.0110(4) -0.0040(4) F6 0.0272(5) 0.0303(5) 0.0398(5) 0.0005(4) 0.0143(4) 0.0099(4) F7 0.0191(5) 0.0517(7) 0.0636(7) 0.0140(5) 0.0130(5) 0.0140(5) F8 0.0241(6) 0.0530(7) 0.0518(7) 0.0091(5) -0.0120(5) -0.0016(5) F9 0.0463(6) 0.0344(6) 0.0300(5) -0.0057(4) -0.0080(4) 0.0072(5) F10 0.0299(5) 0.0350(5) 0.0277(5) -0.0024(4) 0.0074(4) 0.0125(4) F11 0.0337(5) 0.0234(5) 0.0312(5) 0.0086(4) 0.0112(4) 0.0058(4) F12 0.0521(7) 0.0295(5) 0.0384(5) 0.0053(4) 0.0033(5) 0.0218(5) F13 0.0321(6) 0.0492(7) 0.0688(8) -0.0084(6) 0.0073(5) 0.0252(5) F14 0.0214(5) 0.0482(7) 0.0829(8) -0.0056(6) 0.0256(5) 0.0044(5) F15 0.0224(5) 0.0256(5) 0.0571(6) 0.0069(4) 0.0181(4) 0.0024(4) F16 0.0399(6) 0.0302(5) 0.0251(4) 0.0038(4) 0.0157(4) 0.0086(4) F17 0.0581(7) 0.0433(6) 0.0322(5) 0.0196(5) 0.0202(5) 0.0124(5) F18 0.0625(8) 0.0264(5) 0.0528(6) 0.0217(5) 0.0170(6) 0.0122(5) F19 0.0368(6) 0.0218(5) 0.0411(5) -0.0009(4) 0.0062(4) 0.0098(4) F20 0.0350(5) 0.0251(5) 0.0243(4) 0.0027(4) 0.0112(4) 0.0088(4) O1 0.0198(5) 0.0303(6) 0.0180(5) -0.0007(4) 0.0052(4) 0.0035(4) N2 0.0227(7) 0.0223(6) 0.0193(6) 0.0025(5) 0.0059(5) 0.0027(5) N1 0.0230(7) 0.0256(7) 0.0201(6) 0.0029(5) 0.0066(5) 0.0041(5) C2 0.0218(8) 0.0281(8) 0.0179(7) 0.0002(6) 0.0066(6) 0.0009(6) C3 0.0231(8) 0.0347(9) 0.0302(8) -0.0042(7) 0.0057(7) 0.0052(7) C4 0.0199(9) 0.0481(12) 0.0435(10) -0.0119(8) 0.0072(7) 0.0018(8) C5 0.0290(10) 0.0455(12) 0.0425(10) -0.0104(9) 0.0153(8) -0.0105(8) C6 0.0410(11) 0.0339(10) 0.0347(9) 0.0034(7) 0.0117(8) -0.0050(8) C7 0.0273(9) 0.0325(9) 0.0272(8) 0.0064(7) 0.0057(7) 0.0016(7) C1 0.0193(8) 0.0255(8) 0.0186(7) 0.0014(6) 0.0068(6) 0.0031(6) C8 0.0222(8) 0.0231(8) 0.0195(7) 0.0028(6) 0.0060(6) 0.0043(6) C9 0.0245(8) 0.0323(9) 0.0238(7) 0.0028(6) 0.0085(6) 0.0040(7) C10 0.0378(10) 0.0383(10) 0.0210(7) 0.0064(7) 0.0101(7) 0.0103(8) C11 0.0369(10) 0.0367(10) 0.0206(7) 0.0021(7) 0.0002(7) 0.0065(8) C12 0.0278(9) 0.0420(11) 0.0322(9) -0.0002(8) -0.0003(7) -0.0057(8) C13 0.0310(9) 0.0360(10) 0.0248(8) 0.0045(7) 0.0073(7) -0.0039(7) C14 0.0246(8) 0.0255(8) 0.0204(7) 0.0033(6) 0.0045(6) 0.0013(6) C15 0.0372(10) 0.0333(9) 0.0293(8) 0.0073(7) 0.0151(7) 0.0085(8) C16 0.0551(13) 0.0365(10) 0.0463(11) 0.0098(8) 0.0239(10) 0.0180(9) C17 0.0761(16) 0.0379(11) 0.0470(11) 0.0192(9) 0.0227(11) 0.0247(11) C18 0.0824(16) 0.0415(11) 0.0362(10) 0.0174(9) 0.0290(11) 0.0157(11) C19 0.0519(12) 0.0327(9) 0.0279(8) 0.0068(7) 0.0191(8) 0.0090(8) C20 0.0334(9) 0.0297(9) 0.0248(8) 0.0058(6) 0.0138(7) 0.0044(7) C21 0.0342(11) 0.0478(12) 0.0437(10) 0.0041(9) 0.0193(8) 0.0007(9) C22 0.0615(13) 0.0266(9) 0.0383(10) 0.0074(8) 0.0214(9) 0.0017(9) C23 0.0477(12) 0.0473(11) 0.0259(8) 0.0066(8) 0.0151(8) 0.0080(9) C24 0.0239(9) 0.0437(10) 0.0242(8) -0.0005(7) 0.0043(6) 0.0067(7) C25 0.0390(11) 0.0647(14) 0.0375(10) 0.0102(9) 0.0029(8) 0.0298(10) C26 0.0323(10) 0.0695(14) 0.0290(9) -0.0117(9) 0.0036(8) -0.0040(10) C27 0.0242(9) 0.0583(12) 0.0326(9) -0.0053(8) 0.0099(7) 0.0005(8) C28 0.0434(11) 0.0222(8) 0.0384(9) 0.0063(7) 0.0143(8) 0.0131(7) C29 0.0769(16) 0.0315(10) 0.0509(12) -0.0049(9) 0.0242(11) 0.0200(10) C30 0.0627(14) 0.0304(10) 0.0526(12) 0.0140(9) 0.0160(10) 0.0021(9) C31 0.0492(13) 0.0439(11) 0.0578(12) 0.0141(9) 0.0133(10) 0.0282(10) C32 0.0217(8) 0.0184(7) 0.0241(7) 0.0050(6) 0.0080(6) 0.0067(6) C33 0.0236(8) 0.0246(8) 0.0267(7) 0.0081(6) 0.0089(6) 0.0058(6) C34 0.0284(9) 0.0340(9) 0.0271(8) 0.0046(7) 0.0007(7) 0.0075(7) C35 0.0384(10) 0.0445(10) 0.0220(8) 0.0125(7) 0.0103(7) 0.0169(8) C36 0.0323(9) 0.0316(9) 0.0337(8) 0.0152(7) 0.0185(7) 0.0110(7) C37 0.0240(8) 0.0215(8) 0.0288(8) 0.0056(6) 0.0099(6) 0.0054(6) C38 0.0190(8) 0.0181(7) 0.0231(7) 0.0074(6) 0.0065(6) 0.0038(6) C39 0.0231(8) 0.0205(7) 0.0286(8) 0.0058(6) 0.0089(6) 0.0056(6) C40 0.0187(8) 0.0312(9) 0.0408(9) 0.0167(7) 0.0090(7) 0.0087(7) C41 0.0200(8) 0.0310(9) 0.0331(8) 0.0129(7) -0.0043(6) -0.0006(7) C42 0.0333(9) 0.0220(8) 0.0230(7) 0.0058(6) -0.0005(7) 0.0049(7) C43 0.0233(8) 0.0221(8) 0.0240(7) 0.0078(6) 0.0063(6) 0.0065(6) C44 0.0180(7) 0.0221(7) 0.0206(7) 0.0005(6) 0.0034(6) 0.0058(6) C45 0.0234(8) 0.0254(8) 0.0193(7) 0.0022(6) 0.0023(6) 0.0058(6) C46 0.0339(9) 0.0246(8) 0.0242(7) -0.0002(6) -0.0017(7) 0.0130(7) C47 0.0249(9) 0.0388(10) 0.0354(9) -0.0069(7) 0.0005(7) 0.0183(8) C48 0.0176(8) 0.0374(10) 0.0393(9) -0.0047(7) 0.0078(7) 0.0054(7) C49 0.0213(8) 0.0232(8) 0.0311(8) 0.0003(6) 0.0070(6) 0.0047(6) C50 0.0134(7) 0.0199(7) 0.0245(7) 0.0043(6) 0.0058(6) 0.0026(6) C51 0.0192(8) 0.0245(8) 0.0247(7) 0.0033(6) 0.0069(6) 0.0041(6) C52 0.0269(9) 0.0329(9) 0.0258(8) 0.0130(7) 0.0090(7) 0.0059(7) C53 0.0281(9) 0.0227(8) 0.0390(9) 0.0142(7) 0.0078(7) 0.0052(7) C54 0.0199(8) 0.0200(8) 0.0332(8) 0.0015(6) 0.0040(6) 0.0051(6) C55 0.0177(7) 0.0245(8) 0.0232(7) 0.0057(6) 0.0063(6) 0.0049(6) B1 0.0190(8) 0.0173(8) 0.0226(8) 0.0033(6) 0.0077(6) 0.0038(6) _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 1.7217(13) . ? P1 C28 1.8682(17) . ? P1 C24 1.8770(17) . ? P1 C20 1.8798(16) . ? F1 C33 1.3569(17) . ? F2 C34 1.3478(19) . ? F3 C35 1.3429(18) . ? F4 C36 1.3477(18) . ? F5 C37 1.3585(18) . ? F6 C39 1.3526(17) . ? F7 C40 1.3436(18) . ? F8 C41 1.3481(18) . ? F9 C42 1.3377(18) . ? F10 C43 1.3513(17) . ? F11 C45 1.3597(18) . ? F12 C46 1.3452(19) . ? F13 C47 1.3416(19) . ? F14 C48 1.3518(19) . ? F15 C49 1.3594(18) . ? F16 C51 1.3566(17) . ? F17 C52 1.3524(17) . ? F18 C53 1.3387(18) . ? F19 C54 1.3448(17) . ? F20 C55 1.3502(16) . ? O1 N2 1.3752(15) . ? O1 C1 1.4955(17) . ? N2 N1 1.2418(17) . ? C2 C3 1.383(2) . ? C2 C7 1.391(2) . ? C2 C1 1.531(2) . ? C3 C4 1.398(2) . ? C3 H2 0.9300 . ? C4 C5 1.370(3) . ? C4 H3 0.9300 . ? C5 C6 1.386(3) . ? C5 H4 0.9300 . ? C6 C7 1.383(2) . ? C6 H5 0.9300 . ? C7 H6 0.9300 . ? C1 C14 1.527(2) . ? C1 C8 1.529(2) . ? C8 C13 1.387(2) . ? C8 C9 1.391(2) . ? C9 C10 1.388(2) . ? C9 H9 0.9300 . ? C10 C11 1.382(2) . ? C10 H10 0.9300 . ? C11 C12 1.374(2) . ? C11 H11 0.9300 . ? C12 C13 1.388(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.388(2) . ? C14 C15 1.393(2) . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 C17 1.384(3) . ? C16 H16 0.9300 . ? C17 C18 1.375(3) . ? C17 H17 0.9300 . ? C18 C19 1.388(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.539(3) . ? C20 C22 1.539(2) . ? C20 C23 1.540(2) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.538(3) . ? C24 C26 1.551(2) . ? C24 C27 1.553(2) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C30 1.535(3) . ? C28 C31 1.542(3) . ? C28 C29 1.544(2) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C37 1.382(2) . ? C32 C33 1.391(2) . ? C32 B1 1.658(2) . ? C33 C34 1.378(2) . ? C34 C35 1.377(2) . ? C35 C36 1.364(2) . ? C36 C37 1.381(2) . ? C38 C43 1.385(2) . ? C38 C39 1.394(2) . ? C38 B1 1.648(2) . ? C39 C40 1.377(2) . ? C40 C41 1.370(2) . ? C41 C42 1.374(2) . ? C42 C43 1.382(2) . ? C44 C49 1.384(2) . ? C44 C45 1.391(2) . ? C44 B1 1.659(2) . ? C45 C46 1.375(2) . ? C46 C47 1.378(3) . ? C47 C48 1.367(3) . ? C48 C49 1.387(2) . ? C50 C55 1.389(2) . ? C50 C51 1.394(2) . ? C50 B1 1.654(2) . ? C51 C52 1.377(2) . ? C52 C53 1.372(2) . ? C53 C54 1.375(2) . ? C54 C55 1.382(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 N1 P1 C28 101.00(7) . . ? N1 P1 C24 112.99(7) . . ? C28 P1 C24 114.09(8) . . ? N1 P1 C20 100.21(7) . . ? C28 P1 C20 113.51(8) . . ? C24 P1 C20 113.51(8) . . ? N2 O1 C1 110.68(10) . . ? N1 N2 O1 108.52(12) . . ? N2 N1 P1 115.98(10) . . ? C3 C2 C7 118.67(15) . . ? C3 C2 C1 122.94(15) . . ? C7 C2 C1 118.37(14) . . ? C2 C3 C4 120.05(17) . . ? C2 C3 H2 120.0 . . ? C4 C3 H2 120.0 . . ? C5 C4 C3 120.76(18) . . ? C5 C4 H3 119.6 . . ? C3 C4 H3 119.6 . . ? C4 C5 C6 119.59(17) . . ? C4 C5 H4 120.2 . . ? C6 C5 H4 120.2 . . ? C7 C6 C5 119.79(18) . . ? C7 C6 H5 120.1 . . ? C5 C6 H5 120.1 . . ? C6 C7 C2 121.11(17) . . ? C6 C7 H6 119.4 . . ? C2 C7 H6 119.4 . . ? O1 C1 C14 109.75(11) . . ? O1 C1 C8 102.21(11) . . ? C14 C1 C8 109.52(12) . . ? O1 C1 C2 107.58(11) . . ? C14 C1 C2 113.87(13) . . ? C8 C1 C2 113.21(12) . . ? C13 C8 C9 118.57(14) . . ? C13 C8 C1 119.30(13) . . ? C9 C8 C1 122.08(13) . . ? C10 C9 C8 120.57(15) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.21(15) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.55(15) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.54(16) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C8 C13 C12 120.56(15) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C19 C14 C15 118.27(15) . . ? C19 C14 C1 123.48(14) . . ? C15 C14 C1 118.25(13) . . ? C16 C15 C14 121.00(15) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 120.04(17) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 119.48(18) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.61(17) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 120.49(16) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C22 105.75(15) . . ? C21 C20 C23 108.42(14) . . ? C22 C20 C23 110.64(15) . . ? C21 C20 P1 111.59(12) . . ? C22 C20 P1 108.53(11) . . ? C23 C20 P1 111.75(12) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C26 109.85(16) . . ? C25 C24 C27 106.65(15) . . ? C26 C24 C27 107.67(15) . . ? C25 C24 P1 110.13(13) . . ? C26 C24 P1 110.29(12) . . ? C27 C24 P1 112.15(12) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C30 C28 C31 106.24(16) . . ? C30 C28 C29 108.98(16) . . ? C31 C28 C29 110.00(16) . . ? C30 C28 P1 110.32(13) . . ? C31 C28 P1 110.66(12) . . ? C29 C28 P1 110.54(13) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C37 C32 C33 112.98(13) . . ? C37 C32 B1 127.77(13) . . ? C33 C32 B1 119.20(12) . . ? F1 C33 C34 116.24(14) . . ? F1 C33 C32 119.07(13) . . ? C34 C33 C32 124.66(14) . . ? F2 C34 C35 119.94(14) . . ? F2 C34 C33 120.76(15) . . ? C35 C34 C33 119.30(15) . . ? F3 C35 C36 120.68(15) . . ? F3 C35 C34 120.71(16) . . ? C36 C35 C34 118.61(14) . . ? F4 C36 C35 119.60(14) . . ? F4 C36 C37 120.21(15) . . ? C35 C36 C37 120.19(14) . . ? F5 C37 C36 114.33(13) . . ? F5 C37 C32 121.50(13) . . ? C36 C37 C32 124.17(15) . . ? C43 C38 C39 113.15(13) . . ? C43 C38 B1 127.13(13) . . ? C39 C38 B1 119.55(13) . . ? F6 C39 C40 116.08(13) . . ? F6 C39 C38 119.47(13) . . ? C40 C39 C38 124.44(14) . . ? F7 C40 C41 119.96(15) . . ? F7 C40 C39 120.68(15) . . ? C41 C40 C39 119.36(15) . . ? F8 C41 C40 120.66(16) . . ? F8 C41 C42 120.13(15) . . ? C40 C41 C42 119.21(14) . . ? F9 C42 C41 119.96(14) . . ? F9 C42 C43 120.59(15) . . ? C41 C42 C43 119.45(14) . . ? F10 C43 C42 114.69(13) . . ? F10 C43 C38 121.05(13) . . ? C42 C43 C38 124.25(14) . . ? C49 C44 C45 112.79(14) . . ? C49 C44 B1 127.67(13) . . ? C45 C44 B1 119.32(13) . . ? F11 C45 C46 116.08(14) . . ? F11 C45 C44 118.65(13) . . ? C46 C45 C44 125.26(15) . . ? F12 C46 C45 121.15(15) . . ? F12 C46 C47 119.75(15) . . ? C45 C46 C47 119.08(15) . . ? F13 C47 C48 120.54(16) . . ? F13 C47 C46 120.85(16) . . ? C48 C47 C46 118.61(15) . . ? F14 C48 C47 120.38(15) . . ? F14 C48 C49 119.40(16) . . ? C47 C48 C49 120.22(15) . . ? F15 C49 C44 121.56(13) . . ? F15 C49 C48 114.51(14) . . ? C44 C49 C48 123.93(15) . . ? C55 C50 C51 112.98(13) . . ? C55 C50 B1 126.82(12) . . ? C51 C50 B1 119.89(12) . . ? F16 C51 C52 116.21(13) . . ? F16 C51 C50 119.26(13) . . ? C52 C51 C50 124.53(14) . . ? F17 C52 C53 119.78(14) . . ? F17 C52 C51 120.61(14) . . ? C53 C52 C51 119.61(14) . . ? F18 C53 C52 121.00(15) . . ? F18 C53 C54 120.17(15) . . ? C52 C53 C54 118.83(14) . . ? F19 C54 C53 119.65(14) . . ? F19 C54 C55 120.63(14) . . ? C53 C54 C55 119.72(14) . . ? F20 C55 C54 114.68(13) . . ? F20 C55 C50 121.07(13) . . ? C54 C55 C50 124.25(14) . . ? C38 B1 C50 102.46(11) . . ? C38 B1 C32 113.25(12) . . ? C50 B1 C32 112.77(11) . . ? C38 B1 C44 112.54(12) . . ? C50 B1 C44 114.04(12) . . ? C32 B1 C44 102.22(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.351 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.048 data_C42H43BF15N2OPZr_Compound11 _database_code_depnum_ccdc_archive 'CCDC 786857' #TrackingRef 'All-Compounds.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C21 H21.50 B0.50 F7.50 N O0.50 P0.50 Zr0.50' _chemical_formula_weight 504.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 15.6655(7) _cell_length_b 12.5681(6) _cell_length_c 21.5094(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.812(2) _cell_angle_gamma 90.00 _cell_volume 4225.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9953 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.74 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6714 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35224 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.42 _reflns_number_total 9538 _reflns_number_gt 6004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+3.7172P] 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 9538 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Zr1 Zr 0.25193(2) 0.74590(3) 0.024618(18) 0.02648(12) Uani 1 1 d . . . P1 P 0.26551(6) 0.33952(8) 0.12722(5) 0.0249(2) Uani 1 1 d . . . O1 O 0.26439(17) 0.6303(2) 0.09542(14) 0.0364(7) Uani 1 1 d . . . N1 N 0.2735(2) 0.4749(3) 0.13700(17) 0.0357(9) Uani 1 1 d . . . N2 N 0.2559(2) 0.5223(3) 0.08761(17) 0.0372(9) Uani 1 1 d . . . C48 C 0.4083(3) 0.7112(5) 0.0197(2) 0.0515(14) Uani 1 1 d . . . H48A H 0.4474 0.6866 0.0542 0.062 Uiso 1 1 calc R . . C49 C 0.3662(3) 0.6465(4) -0.0261(2) 0.0372(10) Uani 1 1 d . . . H49A H 0.3708 0.5689 -0.0286 0.045 Uiso 1 1 calc R . . C50 C 0.3462(3) 0.8177(4) -0.0556(2) 0.0446(12) Uani 1 1 d . . . H50A H 0.3336 0.8797 -0.0823 0.054 Uiso 1 1 calc R . . C53 C 0.1363(3) 0.7898(4) -0.0561(2) 0.0377(11) Uani 1 1 d . . . H53A H 0.1447 0.8233 -0.0964 0.045 Uiso 1 1 calc R . . C54 C 0.3287(3) 0.7118(4) -0.0718(2) 0.0391(11) Uani 1 1 d . . . H54A H 0.3019 0.6876 -0.1118 0.047 Uiso 1 1 calc R . . C56 C 0.0952(3) 0.7672(5) 0.0409(2) 0.0606(17) Uani 1 1 d . . . H56A H 0.0709 0.7820 0.0809 0.073 Uiso 1 1 calc R . . C57 C 0.1315(3) 0.6812(4) -0.0456(2) 0.0454(13) Uani 1 1 d . . . H57A H 0.1348 0.6255 -0.0772 0.054 Uiso 1 1 calc R . . C58 C 0.1044(3) 0.6674(5) 0.0151(3) 0.0641(18) Uani 1 1 d . . . H58A H 0.0871 0.5999 0.0333 0.077 Uiso 1 1 calc R . . C60 C 0.1144(3) 0.8428(4) -0.0029(2) 0.0491(13) Uani 1 1 d . . . H60A H 0.1055 0.9197 0.0007 0.059 Uiso 1 1 calc R . . C61 C 0.3959(3) 0.8184(4) 0.0002(2) 0.0501(13) Uani 1 1 d . . . H61A H 0.4240 0.8808 0.0196 0.060 Uiso 1 1 calc R . . C65 C 0.2679(3) 0.8941(4) 0.0839(2) 0.0472(12) Uani 1 1 d . . . H65A H 0.2184 0.9034 0.1073 0.071 Uiso 1 1 calc R . . H65B H 0.2743 0.9548 0.0575 0.071 Uiso 1 1 calc R . . H65C H 0.3178 0.8870 0.1120 0.071 Uiso 1 1 calc R . . F15 F 1.05847(13) -0.01421(18) 0.14284(11) 0.0351(6) Uani 1 1 d . . . F14 F 1.02559(13) 0.09982(18) 0.24252(10) 0.0321(5) Uani 1 1 d . . . F13 F 0.93593(15) 0.27901(17) 0.19824(10) 0.0322(5) Uani 1 1 d . . . F12 F 0.74195(13) 0.02338(18) 0.38723(11) 0.0354(6) Uani 1 1 d . . . F11 F 0.57742(13) 0.0643(2) 0.39468(10) 0.0384(6) Uani 1 1 d . . . F10 F 0.99919(15) 0.47151(19) 0.22047(12) 0.0421(6) Uani 1 1 d . . . F9 F 0.86854(15) 0.25572(18) 0.40985(10) 0.0340(5) Uani 1 1 d . . . F8 F 0.76497(14) -0.0811(2) 0.10231(11) 0.0427(6) Uani 1 1 d . . . F7 F 0.75073(14) 0.27353(18) 0.22279(11) 0.0357(6) Uani 1 1 d . . . F6 F 0.49657(13) 0.2118(2) 0.31892(11) 0.0403(6) Uani 1 1 d . . . F5 F 0.93257(16) 0.4481(2) 0.42980(11) 0.0443(7) Uani 1 1 d . . . F4 F 0.72922(13) 0.02673(19) 0.20194(11) 0.0363(6) Uani 1 1 d . . . F3 F 0.99838(16) 0.56015(19) 0.33529(13) 0.0501(7) Uani 1 1 d . . . C14 C 0.9577(2) 0.0559(3) 0.20960(17) 0.0235(8) Uani 1 1 d . . . C16 C 0.9769(2) -0.0022(3) 0.15860(18) 0.0258(9) Uani 1 1 d . . . F2 F 0.58598(14) 0.31596(19) 0.23352(11) 0.0407(6) Uani 1 1 d . . . C18 C 0.8753(2) 0.0724(3) 0.22882(17) 0.0212(8) Uani 1 1 d . . . F1 F 0.92908(15) -0.10553(19) 0.07072(11) 0.0391(6) Uani 1 1 d . . . C20 C 0.5806(2) 0.1921(3) 0.31482(18) 0.0273(9) Uani 1 1 d . . . C21 C 0.7572(2) 0.1495(3) 0.30559(17) 0.0206(8) Uani 1 1 d . . . C24 C 0.6216(2) 0.1187(3) 0.35306(18) 0.0268(9) Uani 1 1 d . . . B1 B 0.8609(3) 0.1307(3) 0.2969(2) 0.0213(9) Uani 1 1 d . . . C26 C 0.9027(2) 0.2524(3) 0.30358(17) 0.0215(8) Uani 1 1 d . . . C27 C 0.9032(2) 0.3036(3) 0.36110(18) 0.0243(9) Uani 1 1 d . . . C28 C 0.8133(2) 0.0214(3) 0.19013(18) 0.0251(9) Uani 1 1 d . . . C30 C 0.9347(2) 0.4038(3) 0.37238(19) 0.0303(10) Uani 1 1 d . . . C32 C 0.7113(2) 0.2219(3) 0.26796(18) 0.0236(9) Uani 1 1 d . . . C33 C 0.9350(2) 0.3144(3) 0.25774(18) 0.0237(9) Uani 1 1 d . . . C34 C 0.8290(2) -0.0363(3) 0.13772(18) 0.0275(9) Uani 1 1 d . . . C35 C 0.7081(2) 0.0989(3) 0.34743(17) 0.0235(8) Uani 1 1 d . . . C38 C 0.9677(2) 0.4158(3) 0.2676(2) 0.0274(9) Uani 1 1 d . . . C39 C 0.6257(2) 0.2441(3) 0.27198(18) 0.0268(9) Uani 1 1 d . . . C40 C 0.9120(2) -0.0488(3) 0.12177(18) 0.0275(9) Uani 1 1 d . . . C42 C 0.9095(2) 0.0532(3) 0.34907(18) 0.0285(9) Uani 1 1 d . . . H42A H 0.9686 0.0463 0.3405 0.043 Uiso 1 1 calc R . . H42B H 0.8829 -0.0157 0.3476 0.043 Uiso 1 1 calc R . . H42C H 0.9055 0.0835 0.3897 0.043 Uiso 1 1 calc R . . C45 C 0.9676(2) 0.4605(3) 0.3256(2) 0.0316(10) Uani 1 1 d . . . C112 C 0.3650(2) 0.2957(3) 0.09045(18) 0.0267(9) Uani 1 1 d . . . C111 C 0.2628(3) 0.2955(4) 0.2104(2) 0.0376(11) Uani 1 1 d . . . C110 C 0.1650(2) 0.3032(3) 0.07876(19) 0.0301(10) Uani 1 1 d . . . C109 C 0.3823(3) 0.3705(4) 0.0365(2) 0.0369(10) Uani 1 1 d . . . H10A H 0.4332 0.3481 0.0177 0.055 Uiso 1 1 calc R . . H10B H 0.3899 0.4417 0.0521 0.055 Uiso 1 1 calc R . . H10C H 0.3347 0.3686 0.0060 0.055 Uiso 1 1 calc R . . C108 C 0.1755(3) 0.3207(4) 0.00931(19) 0.0401(11) Uani 1 1 d . . . H10D H 0.1235 0.3015 -0.0141 0.060 Uiso 1 1 calc R . . H10E H 0.2216 0.2774 -0.0036 0.060 Uiso 1 1 calc R . . H10F H 0.1881 0.3943 0.0021 0.060 Uiso 1 1 calc R . . C107 C 0.3568(3) 0.1796(3) 0.0672(2) 0.0382(11) Uani 1 1 d . . . H10G H 0.4085 0.1591 0.0486 0.057 Uiso 1 1 calc R . . H10H H 0.3094 0.1740 0.0368 0.057 Uiso 1 1 calc R . . H10I H 0.3476 0.1335 0.1017 0.057 Uiso 1 1 calc R . . C106 C 0.4435(2) 0.3040(4) 0.1370(2) 0.0344(10) Uani 1 1 d . . . H10J H 0.4936 0.2812 0.1173 0.052 Uiso 1 1 calc R . . H10K H 0.4353 0.2596 0.1724 0.052 Uiso 1 1 calc R . . H10L H 0.4507 0.3765 0.1504 0.052 Uiso 1 1 calc R . . C105 C 0.2827(3) 0.1764(4) 0.2189(2) 0.0486(13) Uani 1 1 d . . . H10M H 0.2806 0.1577 0.2621 0.073 Uiso 1 1 calc R . . H10N H 0.3388 0.1618 0.2056 0.073 Uiso 1 1 calc R . . H10O H 0.2412 0.1354 0.1944 0.073 Uiso 1 1 calc R . . C104 C 0.1394(3) 0.1886(4) 0.0893(2) 0.0448(12) Uani 1 1 d . . . H10P H 0.0881 0.1727 0.0641 0.067 Uiso 1 1 calc R . . H10Q H 0.1294 0.1784 0.1324 0.067 Uiso 1 1 calc R . . H10R H 0.1846 0.1422 0.0780 0.067 Uiso 1 1 calc R . . C103 C 0.3290(3) 0.3603(4) 0.2518(2) 0.0460(12) Uani 1 1 d . . . H10S H 0.3276 0.3376 0.2943 0.069 Uiso 1 1 calc R . . H10T H 0.3152 0.4346 0.2488 0.069 Uiso 1 1 calc R . . H10U H 0.3852 0.3488 0.2378 0.069 Uiso 1 1 calc R . . C102 C 0.0915(2) 0.3774(4) 0.0965(2) 0.0437(12) Uani 1 1 d . . . H10V H 0.0400 0.3592 0.0721 0.065 Uiso 1 1 calc R . . H10W H 0.1065 0.4499 0.0885 0.065 Uiso 1 1 calc R . . H10X H 0.0826 0.3690 0.1400 0.065 Uiso 1 1 calc R . . C101 C 0.1756(3) 0.3199(5) 0.2344(2) 0.0541(14) Uani 1 1 d . . . H10Y H 0.1746 0.2971 0.2769 0.081 Uiso 1 1 calc R . . H10Z H 0.1320 0.2829 0.2094 0.081 Uiso 1 1 calc R . . H11A H 0.1651 0.3951 0.2320 0.081 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 Zr1 0.02426(18) 0.0251(2) 0.0304(2) -0.00102(18) 0.00360(14) -0.00007(16) P1 0.0204(4) 0.0247(6) 0.0296(6) -0.0021(5) 0.0023(4) -0.0031(4) O1 0.0367(15) 0.0222(17) 0.0499(19) 0.0085(14) -0.0003(13) -0.0041(12) N1 0.0305(18) 0.037(2) 0.039(2) 0.0032(18) 0.0005(15) -0.0018(16) N2 0.0291(17) 0.044(3) 0.039(2) 0.0056(19) 0.0012(15) 0.0005(16) C48 0.023(2) 0.089(4) 0.043(3) 0.005(3) 0.0044(19) 0.011(2) C49 0.037(2) 0.035(3) 0.042(3) 0.001(2) 0.017(2) 0.0054(19) C50 0.034(2) 0.043(3) 0.058(3) 0.010(3) 0.017(2) -0.007(2) C53 0.031(2) 0.043(3) 0.039(3) 0.007(2) -0.0004(18) 0.0001(19) C54 0.034(2) 0.052(3) 0.033(3) -0.003(2) 0.0123(18) -0.004(2) C56 0.042(3) 0.100(5) 0.042(3) 0.020(3) 0.014(2) 0.028(3) C57 0.027(2) 0.043(3) 0.065(4) -0.013(3) -0.013(2) 0.003(2) C58 0.020(2) 0.070(4) 0.100(5) 0.053(4) -0.009(2) -0.013(2) C60 0.048(3) 0.049(3) 0.050(3) -0.003(3) -0.003(2) 0.025(2) C61 0.029(2) 0.055(4) 0.067(4) -0.015(3) 0.010(2) -0.016(2) C65 0.063(3) 0.040(3) 0.040(3) -0.007(2) 0.014(2) -0.002(2) F15 0.0267(11) 0.0338(14) 0.0463(15) -0.0062(11) 0.0134(10) 0.0037(10) F14 0.0223(10) 0.0328(14) 0.0411(14) -0.0091(11) 0.0018(9) -0.0042(9) F13 0.0462(13) 0.0252(13) 0.0258(13) 0.0018(10) 0.0073(10) -0.0060(10) F12 0.0311(12) 0.0356(14) 0.0403(14) 0.0187(11) 0.0075(10) 0.0033(10) F11 0.0266(11) 0.0551(17) 0.0346(14) 0.0054(12) 0.0112(10) -0.0065(11) F10 0.0405(13) 0.0273(14) 0.0600(17) 0.0113(12) 0.0141(12) -0.0040(11) F9 0.0471(13) 0.0308(14) 0.0248(12) -0.0020(11) 0.0065(10) 0.0058(11) F8 0.0344(13) 0.0477(16) 0.0458(15) -0.0251(13) 0.0009(11) -0.0107(11) F7 0.0336(12) 0.0377(15) 0.0351(14) 0.0158(11) -0.0017(10) -0.0047(10) F6 0.0233(11) 0.0473(16) 0.0505(16) -0.0070(12) 0.0035(10) 0.0069(10) F5 0.0568(16) 0.0354(15) 0.0393(15) -0.0174(12) -0.0075(12) 0.0081(12) F4 0.0218(11) 0.0431(15) 0.0444(14) -0.0175(12) 0.0052(10) -0.0091(10) F3 0.0526(16) 0.0218(14) 0.0751(19) -0.0106(13) -0.0020(14) -0.0113(12) C14 0.0247(18) 0.018(2) 0.027(2) 0.0020(17) 0.0004(15) -0.0034(15) C16 0.0251(18) 0.021(2) 0.032(2) 0.0026(18) 0.0106(16) 0.0019(16) F2 0.0346(13) 0.0326(15) 0.0531(16) 0.0094(12) -0.0119(11) 0.0044(11) C18 0.0241(17) 0.013(2) 0.027(2) -0.0013(16) 0.0024(15) -0.0001(14) F1 0.0481(14) 0.0357(15) 0.0347(14) -0.0160(12) 0.0111(11) 0.0031(11) C20 0.0220(18) 0.029(2) 0.031(2) -0.0103(19) 0.0009(16) 0.0023(16) C21 0.0246(17) 0.015(2) 0.023(2) -0.0049(16) 0.0028(14) -0.0023(15) C24 0.0258(18) 0.027(2) 0.028(2) -0.0043(18) 0.0037(16) -0.0036(16) B1 0.0235(19) 0.018(2) 0.022(2) -0.0006(18) 0.0030(16) -0.0013(17) C26 0.0219(16) 0.017(2) 0.025(2) -0.0005(18) -0.0005(14) 0.0028(15) C27 0.0261(18) 0.019(2) 0.028(2) 0.0009(18) -0.0018(16) 0.0048(16) C28 0.0247(18) 0.021(2) 0.030(2) -0.0042(18) 0.0062(15) -0.0033(16) C30 0.028(2) 0.030(2) 0.031(2) -0.007(2) -0.0054(17) 0.0077(18) C32 0.0274(18) 0.019(2) 0.025(2) -0.0015(16) 0.0019(15) -0.0037(15) C33 0.0203(17) 0.022(2) 0.029(2) -0.0015(18) 0.0016(15) 0.0027(15) C34 0.030(2) 0.019(2) 0.033(2) -0.0043(18) 0.0001(16) -0.0052(16) C35 0.0256(18) 0.020(2) 0.025(2) 0.0005(17) 0.0020(15) 0.0027(15) C38 0.0211(17) 0.019(2) 0.043(3) 0.0080(19) 0.0043(16) 0.0017(15) C39 0.0316(19) 0.020(2) 0.028(2) 0.0012(19) -0.0081(16) 0.0014(17) C40 0.037(2) 0.021(2) 0.025(2) -0.0021(18) 0.0073(16) 0.0005(17) C42 0.0275(19) 0.028(2) 0.030(2) 0.0022(19) 0.0009(16) -0.0005(17) C45 0.0245(19) 0.016(2) 0.053(3) -0.010(2) -0.0055(18) 0.0021(16) C112 0.0226(18) 0.024(2) 0.033(2) -0.0016(18) 0.0031(16) 0.0013(16) C111 0.036(2) 0.049(3) 0.028(2) 0.000(2) 0.0032(18) 0.001(2) C110 0.0231(18) 0.033(3) 0.033(2) 0.0022(19) -0.0046(16) -0.0096(17) C109 0.034(2) 0.040(3) 0.038(3) 0.008(2) 0.0140(18) 0.0042(19) C108 0.034(2) 0.045(3) 0.040(3) 0.005(2) -0.0106(18) -0.007(2) C107 0.042(2) 0.027(3) 0.046(3) -0.003(2) 0.007(2) 0.0013(19) C106 0.0218(18) 0.034(3) 0.047(3) 0.000(2) 0.0026(17) 0.0016(17) C105 0.059(3) 0.049(3) 0.038(3) 0.016(2) 0.002(2) -0.011(2) C104 0.046(3) 0.040(3) 0.047(3) 0.003(2) -0.006(2) -0.018(2) C103 0.042(2) 0.059(3) 0.036(3) -0.007(2) -0.006(2) 0.001(2) C102 0.024(2) 0.049(3) 0.057(3) 0.008(2) -0.0022(19) -0.0007(19) C101 0.035(2) 0.087(4) 0.041(3) -0.002(3) 0.008(2) -0.001(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 Zr1 O1 2.105(3) . ? Zr1 C65 2.261(4) . ? Zr1 C57 2.474(4) . ? Zr1 C53 2.486(4) . ? Zr1 C49 2.492(4) . ? Zr1 C48 2.498(4) . ? Zr1 C54 2.503(4) . ? Zr1 C58 2.509(4) . ? Zr1 C60 2.511(4) . ? Zr1 C50 2.513(4) . ? Zr1 C56 2.518(5) . ? Zr1 C61 2.519(4) . ? P1 N1 1.719(4) . ? P1 C111 1.876(4) . ? P1 C112 1.877(4) . ? P1 C110 1.886(4) . ? O1 N2 1.372(5) . ? N1 N2 1.233(5) . ? C48 C49 1.407(6) . ? C48 C61 1.421(7) . ? C49 C54 1.382(6) . ? C50 C61 1.387(7) . ? C50 C54 1.399(7) . ? C53 C57 1.386(7) . ? C53 C60 1.387(6) . ? C56 C58 1.383(8) . ? C56 C60 1.385(7) . ? C57 C58 1.412(7) . ? F15 C16 1.352(4) . ? F14 C14 1.355(4) . ? F13 C33 1.356(4) . ? F12 C35 1.362(4) . ? F11 C24 1.353(4) . ? F10 C38 1.351(4) . ? F9 C27 1.354(4) . ? F8 C34 1.342(4) . ? F7 C32 1.352(4) . ? F6 C20 1.348(4) . ? F5 C30 1.357(4) . ? F4 C28 1.360(4) . ? F3 C45 1.353(4) . ? C14 C16 1.368(5) . ? C14 C18 1.397(5) . ? C16 C40 1.378(5) . ? F2 C39 1.349(4) . ? C18 C28 1.392(5) . ? C18 B1 1.666(6) . ? F1 C40 1.351(4) . ? C20 C39 1.365(6) . ? C20 C24 1.367(5) . ? C21 C35 1.377(5) . ? C21 C32 1.386(5) . ? C21 B1 1.665(5) . ? C24 C35 1.392(5) . ? B1 C42 1.635(6) . ? B1 C26 1.667(6) . ? C26 C33 1.379(5) . ? C26 C27 1.394(5) . ? C27 C30 1.369(6) . ? C28 C34 1.376(5) . ? C30 C45 1.361(6) . ? C32 C39 1.378(5) . ? C33 C38 1.385(5) . ? C34 C40 1.375(5) . ? C38 C45 1.369(6) . ? C112 C109 1.531(6) . ? C112 C106 1.537(5) . ? C112 C107 1.545(6) . ? C111 C101 1.524(6) . ? C111 C105 1.537(7) . ? C111 C103 1.552(6) . ? C110 C104 1.515(6) . ? C110 C108 1.530(6) . ? C110 C102 1.548(6) . ? 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 O1 Zr1 C65 99.17(15) . . ? O1 Zr1 C57 104.20(15) . . ? C65 Zr1 C57 131.76(17) . . ? O1 Zr1 C53 133.37(13) . . ? C65 Zr1 C53 105.01(17) . . ? C57 Zr1 C53 32.45(15) . . ? O1 Zr1 C49 86.32(13) . . ? C65 Zr1 C49 127.13(17) . . ? C57 Zr1 C49 96.24(16) . . ? C53 Zr1 C49 108.47(15) . . ? O1 Zr1 C48 82.29(15) . . ? C65 Zr1 C48 95.49(18) . . ? C57 Zr1 C48 128.81(17) . . ? C53 Zr1 C48 132.88(15) . . ? C49 Zr1 C48 32.75(15) . . ? O1 Zr1 C54 117.05(14) . . ? C65 Zr1 C54 124.55(16) . . ? C57 Zr1 C54 80.00(16) . . ? C53 Zr1 C54 80.05(15) . . ? C49 Zr1 C54 32.11(14) . . ? C48 Zr1 C54 53.72(15) . . ? O1 Zr1 C58 80.09(14) . . ? C65 Zr1 C58 115.9(2) . . ? C57 Zr1 C58 32.90(17) . . ? C53 Zr1 C58 53.56(15) . . ? C49 Zr1 C58 116.9(2) . . ? C48 Zr1 C58 146.0(2) . . ? C54 Zr1 C58 110.8(2) . . ? O1 Zr1 C60 122.84(15) . . ? C65 Zr1 C60 78.14(17) . . ? C57 Zr1 C60 53.71(16) . . ? C53 Zr1 C60 32.22(15) . . ? C49 Zr1 C60 140.34(15) . . ? C48 Zr1 C60 154.61(18) . . ? C54 Zr1 C60 109.87(16) . . ? C58 Zr1 C60 53.15(18) . . ? O1 Zr1 C50 135.59(14) . . ? C65 Zr1 C50 92.50(17) . . ? C57 Zr1 C50 99.07(17) . . ? C53 Zr1 C50 82.82(15) . . ? C49 Zr1 C50 53.65(15) . . ? C48 Zr1 C50 53.88(16) . . ? C54 Zr1 C50 32.38(15) . . ? C58 Zr1 C50 131.74(18) . . ? C60 Zr1 C50 101.45(17) . . ? O1 Zr1 C56 90.98(15) . . ? C65 Zr1 C56 84.6(2) . . ? C57 Zr1 C56 53.78(17) . . ? C53 Zr1 C56 53.24(15) . . ? C49 Zr1 C56 148.17(19) . . ? C48 Zr1 C56 173.21(17) . . ? C54 Zr1 C56 131.33(16) . . ? C58 Zr1 C56 31.95(19) . . ? C60 Zr1 C56 31.98(17) . . ? C50 Zr1 C56 132.91(16) . . ? O1 Zr1 C61 111.05(15) . . ? C65 Zr1 C61 75.68(17) . . ? C57 Zr1 C61 130.39(17) . . ? C53 Zr1 C61 113.26(17) . . ? C49 Zr1 C61 53.95(16) . . ? C48 Zr1 C61 32.90(17) . . ? C54 Zr1 C61 53.37(15) . . ? C58 Zr1 C61 163.3(2) . . ? C60 Zr1 C61 122.77(19) . . ? C50 Zr1 C61 31.99(15) . . ? C56 Zr1 C61 152.3(2) . . ? N1 P1 C111 100.5(2) . . ? N1 P1 C112 106.67(17) . . ? C111 P1 C112 112.78(18) . . ? N1 P1 C110 111.01(18) . . ? C111 P1 C110 112.64(18) . . ? C112 P1 C110 112.48(18) . . ? N2 O1 Zr1 126.2(2) . . ? N2 N1 P1 111.3(3) . . ? N1 N2 O1 111.0(3) . . ? C49 C48 C61 107.0(4) . . ? C49 C48 Zr1 73.4(2) . . ? C61 C48 Zr1 74.4(2) . . ? C54 C49 C48 108.3(4) . . ? C54 C49 Zr1 74.4(2) . . ? C48 C49 Zr1 73.8(2) . . ? C61 C50 C54 108.2(4) . . ? C61 C50 Zr1 74.3(3) . . ? C54 C50 Zr1 73.4(2) . . ? C57 C53 C60 108.7(4) . . ? C57 C53 Zr1 73.3(2) . . ? C60 C53 Zr1 74.9(3) . . ? C49 C54 C50 108.7(4) . . ? C49 C54 Zr1 73.5(2) . . ? C50 C54 Zr1 74.2(3) . . ? C58 C56 C60 108.4(5) . . ? C58 C56 Zr1 73.7(3) . . ? C60 C56 Zr1 73.7(3) . . ? C53 C57 C58 107.1(5) . . ? C53 C57 Zr1 74.2(2) . . ? C58 C57 Zr1 74.9(3) . . ? C56 C58 C57 107.8(4) . . ? C56 C58 Zr1 74.4(3) . . ? C57 C58 Zr1 72.2(2) . . ? C56 C60 C53 108.0(5) . . ? C56 C60 Zr1 74.3(3) . . ? C53 C60 Zr1 72.9(2) . . ? C50 C61 C48 107.9(4) . . ? C50 C61 Zr1 73.8(2) . . ? C48 C61 Zr1 72.7(2) . . ? F14 C14 C16 115.4(3) . . ? F14 C14 C18 119.6(3) . . ? C16 C14 C18 125.0(3) . . ? F15 C16 C14 121.5(3) . . ? F15 C16 C40 118.9(3) . . ? C14 C16 C40 119.6(3) . . ? C28 C18 C14 112.1(3) . . ? C28 C18 B1 126.8(3) . . ? C14 C18 B1 120.5(3) . . ? F6 C20 C39 120.6(3) . . ? F6 C20 C24 120.4(4) . . ? C39 C20 C24 119.1(3) . . ? C35 C21 C32 113.2(3) . . ? C35 C21 B1 126.8(3) . . ? C32 C21 B1 120.0(3) . . ? F11 C24 C20 120.0(3) . . ? F11 C24 C35 120.7(3) . . ? C20 C24 C35 119.3(4) . . ? C42 B1 C21 114.9(3) . . ? C42 B1 C18 104.9(3) . . ? C21 B1 C18 110.6(3) . . ? C42 B1 C26 109.0(3) . . ? C21 B1 C26 103.9(3) . . ? C18 B1 C26 113.9(3) . . ? C33 C26 C27 113.2(3) . . ? C33 C26 B1 128.1(3) . . ? C27 C26 B1 118.6(3) . . ? F9 C27 C30 115.5(3) . . ? F9 C27 C26 120.3(3) . . ? C30 C27 C26 124.2(4) . . ? F4 C28 C34 114.0(3) . . ? F4 C28 C18 120.8(3) . . ? C34 C28 C18 125.3(3) . . ? F5 C30 C45 119.4(4) . . ? F5 C30 C27 120.5(4) . . ? C45 C30 C27 120.0(4) . . ? F7 C32 C39 116.1(3) . . ? F7 C32 C21 119.4(3) . . ? C39 C32 C21 124.4(4) . . ? F13 C33 C26 121.2(3) . . ? F13 C33 C38 114.8(3) . . ? C26 C33 C38 124.1(4) . . ? F8 C34 C40 119.6(3) . . ? F8 C34 C28 121.3(3) . . ? C40 C34 C28 119.2(3) . . ? F12 C35 C21 121.5(3) . . ? F12 C35 C24 114.3(3) . . ? C21 C35 C24 124.3(3) . . ? F10 C38 C45 119.6(4) . . ? F10 C38 C33 120.8(4) . . ? C45 C38 C33 119.6(4) . . ? F2 C39 C20 119.7(3) . . ? F2 C39 C32 120.6(4) . . ? C20 C39 C32 119.7(3) . . ? F1 C40 C34 120.3(3) . . ? F1 C40 C16 120.8(3) . . ? C34 C40 C16 118.8(4) . . ? F3 C45 C30 121.3(4) . . ? F3 C45 C38 119.8(4) . . ? C30 C45 C38 118.9(4) . . ? C109 C112 C106 106.1(3) . . ? C109 C112 C107 110.5(3) . . ? C106 C112 C107 108.7(3) . . ? C109 C112 P1 109.4(3) . . ? C106 C112 P1 110.9(3) . . ? C107 C112 P1 111.1(3) . . ? C101 C111 C105 109.6(4) . . ? C101 C111 C103 106.3(4) . . ? C105 C111 C103 108.7(4) . . ? C101 C111 P1 109.9(3) . . ? C105 C111 P1 112.6(3) . . ? C103 C111 P1 109.6(3) . . ? C104 C110 C108 109.2(4) . . ? C104 C110 C102 109.1(3) . . ? C108 C110 C102 106.5(3) . . ? C104 C110 P1 111.5(3) . . ? C108 C110 P1 111.4(3) . . ? C102 C110 P1 108.9(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.599 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.090