Supplementary Material (ESI) for Chemical Science This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'David Cole-Hamilton' _publ_contact_author_name 'David Cole-Hamilton' _publ_contact_author_email djc@st-and.ac.uk _publ_section_title ; Highly selective formation of unsaturated esters or cascade reactions to \"i\"i\"i.-diesters by the methoxycarbonylkation of alkynes catalysed by palladium complexes of 1,2-bis(ditertbutylphosphinomethyl)benzene. ; # Attachment '- BDTBPMB.cif' data_BDTBPMBH2 _database_code_depnum_ccdc_archive 'CCDC 774479' #TrackingRef '- BDTBPMB.cif' # start Validation Reply Form _vrf_PLAT029_BDTBPMBH2 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: Weak data further out. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H44 P2' _chemical_formula_sum 'C24 H44 P2' _chemical_formula_weight 394.53 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' 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 9.9447(19) _cell_length_b 11.839(2) _cell_length_c 11.991(2) _cell_angle_alpha 117.625(6) _cell_angle_beta 92.392(9) _cell_angle_gamma 99.186(8) _cell_volume 1224.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6254 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 28.16 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8995 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6891 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4039 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0639P)^2^+0.8685P] 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 4039 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.62975(4) 0.13939(4) -0.27751(4) 0.01278(14) Uani 1 1 d . . . C1 C 0.59559(17) 0.12421(16) -0.13243(15) 0.0136(3) Uani 1 1 d . . . H1A H 0.5856 0.0315 -0.1542 0.016 Uiso 1 1 calc R . . H1B H 0.6770 0.1735 -0.0673 0.016 Uiso 1 1 calc R . . C2 C 0.46901(17) 0.17190(16) -0.07399(16) 0.0142(3) Uani 1 1 d . . . C3 C 0.45699(18) 0.20572(16) 0.05390(16) 0.0156(4) Uani 1 1 d . . . C4 C 0.56845(18) 0.20166(17) 0.14157(16) 0.0164(4) Uani 1 1 d . . . H4A H 0.5860 0.1121 0.1026 0.020 Uiso 1 1 calc R . . H4B H 0.5321 0.2186 0.2223 0.020 Uiso 1 1 calc R . . P4 P 0.73780(4) 0.31718(4) 0.18080(4) 0.01267(14) Uani 1 1 d . . . C5 C 0.35959(18) 0.17622(17) -0.14802(18) 0.0196(4) Uani 1 1 d . . . H5A H 0.3670 0.1535 -0.2343 0.023 Uiso 1 1 calc R . . C6 C 0.24033(19) 0.21288(18) -0.09883(19) 0.0239(4) Uani 1 1 d . . . H6A H 0.1680 0.2164 -0.1507 0.029 Uiso 1 1 calc R . . C7 C 0.22742(19) 0.24421(18) 0.02607(19) 0.0233(4) Uani 1 1 d . . . H7A H 0.1459 0.2686 0.0604 0.028 Uiso 1 1 calc R . . C8 C 0.33450(19) 0.23970(17) 0.10049(18) 0.0209(4) Uani 1 1 d . . . H8A H 0.3246 0.2603 0.1859 0.025 Uiso 1 1 calc R . . C9 C 0.72896(19) 0.00515(17) -0.35558(16) 0.0174(4) Uani 1 1 d . . . C10 C 0.6171(2) -0.11999(18) -0.42053(18) 0.0234(4) Uani 1 1 d . . . H10A H 0.6602 -0.1953 -0.4639 0.035 Uiso 1 1 calc R . . H10B H 0.5544 -0.1149 -0.4826 0.035 Uiso 1 1 calc R . . H10C H 0.5654 -0.1294 -0.3565 0.035 Uiso 1 1 calc R . . C11 C 0.7996(2) 0.0214(2) -0.46027(19) 0.0272(4) Uani 1 1 d . . . H11A H 0.8513 -0.0479 -0.5012 0.041 Uiso 1 1 calc R . . H11B H 0.8627 0.1062 -0.4228 0.041 Uiso 1 1 calc R . . H11C H 0.7300 0.0163 -0.5236 0.041 Uiso 1 1 calc R . . C12 C 0.8342(2) -0.01063(19) -0.26892(18) 0.0230(4) Uani 1 1 d . . . H12A H 0.8784 -0.0829 -0.3204 0.035 Uiso 1 1 calc R . . H12B H 0.7873 -0.0288 -0.2070 0.035 Uiso 1 1 calc R . . H12C H 0.9039 0.0698 -0.2241 0.035 Uiso 1 1 calc R . . C13 C 0.74818(19) 0.30431(17) -0.20782(17) 0.0176(4) Uani 1 1 d . . . C14 C 0.7606(2) 0.3424(2) -0.31448(18) 0.0257(4) Uani 1 1 d . . . H14A H 0.8216 0.4278 -0.2812 0.039 Uiso 1 1 calc R . . H14B H 0.6695 0.3461 -0.3454 0.039 Uiso 1 1 calc R . . H14C H 0.7985 0.2773 -0.3845 0.039 Uiso 1 1 calc R . . C15 C 0.8921(2) 0.31843(19) -0.14628(18) 0.0250(4) Uani 1 1 d . . . H15A H 0.9430 0.4079 -0.1140 0.037 Uiso 1 1 calc R . . H15B H 0.9410 0.2581 -0.2095 0.037 Uiso 1 1 calc R . . H15C H 0.8846 0.2983 -0.0759 0.037 Uiso 1 1 calc R . . C16 C 0.6729(2) 0.39918(18) -0.10769(18) 0.0236(4) Uani 1 1 d . . . H16A H 0.7297 0.4871 -0.0679 0.035 Uiso 1 1 calc R . . H16B H 0.6557 0.3722 -0.0428 0.035 Uiso 1 1 calc R . . H16C H 0.5852 0.3987 -0.1485 0.035 Uiso 1 1 calc R . . C17 C 0.84964(18) 0.23045(17) 0.23334(16) 0.0164(4) Uani 1 1 d . . . C18 C 0.87621(19) 0.11747(17) 0.10887(17) 0.0194(4) Uani 1 1 d . . . H18A H 0.9340 0.0678 0.1288 0.029 Uiso 1 1 calc R . . H18B H 0.9231 0.1527 0.0580 0.029 Uiso 1 1 calc R . . H18C H 0.7884 0.0602 0.0608 0.029 Uiso 1 1 calc R . . C19 C 0.98759(19) 0.32312(18) 0.30167(18) 0.0222(4) Uani 1 1 d . . . H19A H 1.0461 0.2791 0.3292 0.033 Uiso 1 1 calc R . . H19B H 0.9718 0.4007 0.3759 0.033 Uiso 1 1 calc R . . H19C H 1.0330 0.3488 0.2436 0.033 Uiso 1 1 calc R . . C20 C 0.7889(2) 0.17356(19) 0.31685(17) 0.0231(4) Uani 1 1 d . . . H20A H 0.8555 0.1313 0.3379 0.035 Uiso 1 1 calc R . . H20B H 0.7042 0.1094 0.2706 0.035 Uiso 1 1 calc R . . H20C H 0.7684 0.2437 0.3952 0.035 Uiso 1 1 calc R . . C21 C 0.71405(19) 0.47214(17) 0.32203(16) 0.0173(4) Uani 1 1 d . . . C22 C 0.5899(2) 0.51079(18) 0.27711(19) 0.0263(4) Uani 1 1 d . . . H22A H 0.5721 0.5911 0.3466 0.040 Uiso 1 1 calc R . . H22B H 0.5087 0.4409 0.2515 0.040 Uiso 1 1 calc R . . H22C H 0.6098 0.5249 0.2047 0.040 Uiso 1 1 calc R . . C23 C 0.8409(2) 0.57788(18) 0.34705(18) 0.0231(4) Uani 1 1 d . . . H23A H 0.8321 0.6599 0.4199 0.035 Uiso 1 1 calc R . . H23C H 0.8476 0.5901 0.2719 0.035 Uiso 1 1 calc R . . H23D H 0.9237 0.5511 0.3653 0.035 Uiso 1 1 calc R . . C24 C 0.6891(2) 0.46742(19) 0.44507(17) 0.0241(4) Uani 1 1 d . . . H24C H 0.6786 0.5534 0.5103 0.036 Uiso 1 1 calc R . . H24D H 0.7675 0.4427 0.4743 0.036 Uiso 1 1 calc R . . H24A H 0.6054 0.4032 0.4295 0.036 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 0.0160(2) 0.0139(2) 0.0106(2) 0.00784(18) 0.00088(16) 0.00253(17) C1 0.0166(9) 0.0128(8) 0.0133(8) 0.0080(7) 0.0021(6) 0.0022(6) C2 0.0152(8) 0.0106(8) 0.0167(8) 0.0073(7) 0.0026(7) -0.0004(6) C3 0.0173(9) 0.0101(8) 0.0181(9) 0.0070(7) 0.0031(7) -0.0022(6) C4 0.0215(9) 0.0154(8) 0.0130(8) 0.0086(7) 0.0044(7) -0.0001(7) P4 0.0174(2) 0.0119(2) 0.0101(2) 0.00705(18) 0.00181(16) 0.00100(17) C5 0.0188(9) 0.0188(9) 0.0204(9) 0.0094(8) 0.0005(7) 0.0022(7) C6 0.0165(9) 0.0211(10) 0.0318(11) 0.0117(9) -0.0010(8) 0.0023(7) C7 0.0170(9) 0.0158(9) 0.0327(11) 0.0079(8) 0.0082(8) 0.0018(7) C8 0.0217(9) 0.0151(9) 0.0216(9) 0.0064(8) 0.0080(7) -0.0016(7) C9 0.0227(9) 0.0173(9) 0.0145(8) 0.0083(7) 0.0051(7) 0.0071(7) C10 0.0343(11) 0.0161(9) 0.0172(9) 0.0057(8) 0.0040(8) 0.0051(8) C11 0.0348(11) 0.0321(11) 0.0206(10) 0.0150(9) 0.0132(8) 0.0123(9) C12 0.0253(10) 0.0261(10) 0.0240(10) 0.0148(8) 0.0051(8) 0.0123(8) C13 0.0236(10) 0.0153(9) 0.0170(9) 0.0119(7) 0.0012(7) -0.0007(7) C14 0.0354(11) 0.0246(10) 0.0240(10) 0.0191(9) 0.0039(8) -0.0004(8) C15 0.0246(10) 0.0255(10) 0.0232(10) 0.0143(9) -0.0030(8) -0.0062(8) C16 0.0376(11) 0.0138(9) 0.0216(10) 0.0108(8) 0.0048(8) 0.0034(8) C17 0.0221(9) 0.0170(9) 0.0139(8) 0.0104(7) 0.0026(7) 0.0046(7) C18 0.0248(10) 0.0169(9) 0.0183(9) 0.0094(8) 0.0036(7) 0.0061(7) C19 0.0244(10) 0.0208(9) 0.0205(9) 0.0096(8) -0.0013(7) 0.0040(8) C20 0.0345(11) 0.0244(10) 0.0184(9) 0.0162(8) 0.0052(8) 0.0072(8) C21 0.0225(9) 0.0141(8) 0.0139(8) 0.0056(7) 0.0033(7) 0.0032(7) C22 0.0285(11) 0.0172(9) 0.0267(10) 0.0045(8) -0.0025(8) 0.0080(8) C23 0.0291(10) 0.0139(9) 0.0219(10) 0.0062(8) 0.0024(8) 0.0009(8) C24 0.0306(11) 0.0237(10) 0.0147(9) 0.0067(8) 0.0072(8) 0.0034(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 C1 1.8692(17) . ? P1 C13 1.8890(18) . ? P1 C9 1.8904(18) . ? C1 C2 1.526(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.398(2) . ? C2 C3 1.410(2) . ? C3 C8 1.401(3) . ? C3 C4 1.517(2) . ? C4 P4 1.8788(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? P4 C21 1.8921(18) . ? P4 C17 1.8959(18) . ? C5 C6 1.389(3) . ? C5 H5A 0.9500 . ? C6 C7 1.383(3) . ? C6 H6A 0.9500 . ? C7 C8 1.384(3) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C11 1.537(3) . ? C9 C12 1.537(2) . ? C9 C10 1.540(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 C15 1.531(3) . ? C13 C16 1.535(3) . ? C13 C14 1.544(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.533(3) . ? C17 C20 1.538(2) . ? C17 C18 1.543(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C24 1.531(2) . ? C21 C23 1.537(3) . ? C21 C22 1.542(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23C 0.9800 . ? C23 H23D 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C13 102.04(8) . . ? C1 P1 C9 100.06(8) . . ? C13 P1 C9 110.61(8) . . ? C2 C1 P1 115.86(12) . . ? C2 C1 H1A 108.3 . . ? P1 C1 H1A 108.3 . . ? C2 C1 H1B 108.3 . . ? P1 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C5 C2 C3 118.71(16) . . ? C5 C2 C1 120.61(15) . . ? C3 C2 C1 120.60(15) . . ? C8 C3 C2 118.42(16) . . ? C8 C3 C4 118.64(16) . . ? C2 C3 C4 122.89(15) . . ? C3 C4 P4 117.46(12) . . ? C3 C4 H4A 107.9 . . ? P4 C4 H4A 107.9 . . ? C3 C4 H4B 107.9 . . ? P4 C4 H4B 107.9 . . ? H4A C4 H4B 107.2 . . ? C4 P4 C21 104.30(8) . . ? C4 P4 C17 98.99(8) . . ? C21 P4 C17 110.33(8) . . ? C6 C5 C2 121.76(17) . . ? C6 C5 H5A 119.1 . . ? C2 C5 H5A 119.1 . . ? C7 C6 C5 119.65(17) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C8 119.32(17) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C7 C8 C3 122.12(17) . . ? C7 C8 H8A 118.9 . . ? C3 C8 H8A 118.9 . . ? C11 C9 C12 109.64(15) . . ? C11 C9 C10 107.64(15) . . ? C12 C9 C10 108.57(15) . . ? C11 C9 P1 109.05(12) . . ? C12 C9 P1 117.34(12) . . ? C10 C9 P1 104.10(12) . . ? 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 . . ? C15 C13 C16 108.88(15) . . ? C15 C13 C14 109.30(15) . . ? C16 C13 C14 107.71(15) . . ? C15 C13 P1 117.44(13) . . ? C16 C13 P1 105.64(12) . . ? C14 C13 P1 107.45(12) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C19 C17 C20 109.41(15) . . ? C19 C17 C18 108.17(15) . . ? C20 C17 C18 108.35(15) . . ? C19 C17 P4 108.89(12) . . ? C20 C17 P4 116.80(13) . . ? C18 C17 P4 104.86(11) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C24 C21 C23 109.93(15) . . ? C24 C21 C22 108.88(16) . . ? C23 C21 C22 107.14(15) . . ? C24 C21 P4 117.69(13) . . ? C23 C21 P4 107.20(12) . . ? C22 C21 P4 105.48(12) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? C21 C23 H23D 109.5 . . ? H23A C23 H23D 109.5 . . ? H23C C23 H23D 109.5 . . ? C21 C24 H24C 109.5 . . ? C21 C24 H24D 109.5 . . ? H24C C24 H24D 109.5 . . ? C21 C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? H24D C24 H24A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 P1 C1 C2 92.03(13) . . . . ? C9 P1 C1 C2 -154.18(12) . . . . ? P1 C1 C2 C5 24.5(2) . . . . ? P1 C1 C2 C3 -158.96(13) . . . . ? C5 C2 C3 C8 1.3(2) . . . . ? C1 C2 C3 C8 -175.34(15) . . . . ? C5 C2 C3 C4 178.73(15) . . . . ? C1 C2 C3 C4 2.1(2) . . . . ? C8 C3 C4 P4 -117.81(15) . . . . ? C2 C3 C4 P4 64.7(2) . . . . ? C3 C4 P4 C21 86.57(14) . . . . ? C3 C4 P4 C17 -159.65(13) . . . . ? C3 C2 C5 C6 0.1(3) . . . . ? C1 C2 C5 C6 176.66(16) . . . . ? C2 C5 C6 C7 -1.0(3) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C6 C7 C8 C3 0.7(3) . . . . ? C2 C3 C8 C7 -1.7(3) . . . . ? C4 C3 C8 C7 -179.28(16) . . . . ? C1 P1 C9 C11 -165.80(13) . . . . ? C13 P1 C9 C11 -58.76(15) . . . . ? C1 P1 C9 C12 -40.43(15) . . . . ? C13 P1 C9 C12 66.61(15) . . . . ? C1 P1 C9 C10 79.53(12) . . . . ? C13 P1 C9 C10 -173.42(11) . . . . ? C1 P1 C13 C15 68.11(15) . . . . ? C9 P1 C13 C15 -37.62(16) . . . . ? C1 P1 C13 C16 -53.49(13) . . . . ? C9 P1 C13 C16 -159.22(11) . . . . ? C1 P1 C13 C14 -168.28(13) . . . . ? C9 P1 C13 C14 85.99(14) . . . . ? C4 P4 C17 C19 -166.15(12) . . . . ? C21 P4 C17 C19 -57.18(14) . . . . ? C4 P4 C17 C20 -41.66(15) . . . . ? C21 P4 C17 C20 67.32(15) . . . . ? C4 P4 C17 C18 78.27(12) . . . . ? C21 P4 C17 C18 -172.75(11) . . . . ? C4 P4 C21 C24 63.98(15) . . . . ? C17 P4 C21 C24 -41.47(16) . . . . ? C4 P4 C21 C23 -171.59(12) . . . . ? C17 P4 C21 C23 82.96(13) . . . . ? C4 P4 C21 C22 -57.65(14) . . . . ? C17 P4 C21 C22 -163.09(12) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.433 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.055 # Attachment '- Pd(BDTBPMB)Cl2.cif' data_PdBDTBPMBCl2 _database_code_depnum_ccdc_archive 'CCDC 774480' #TrackingRef '- Pd(BDTBPMB)Cl2.cif' # start Validation Reply Form _vrf_PLAT029_PdBDTBPMBCl2 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.89 RESPONSE: Weak data further out. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H44 Cl2 P2 Pd' _chemical_formula_sum 'C24 H44 Cl2 P2 Pd' _chemical_formula_weight 571.83 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' P P 0.1023 0.0942 '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' Pd Pd -0.9988 1.0072 '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 9.1553(15) _cell_length_b 19.646(3) _cell_length_c 15.159(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.766(5) _cell_angle_gamma 90.00 _cell_volume 2669.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7217 _cell_measurement_theta_min 1.7196 _cell_measurement_theta_max 28.6648 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0700 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 1.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8170 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14255 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4316 _reflns_number_gt 3889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0339P)^2^+2.5154P] 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 4316 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.002 _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 Pd1 Pd 0.70096(2) 0.234949(10) 0.016154(15) 0.01203(9) Uani 1 1 d . . . Cl1 Cl 0.63122(8) 0.30121(3) -0.11595(5) 0.01838(16) Uani 1 1 d . . . Cl2 Cl 0.61022(8) 0.14382(3) -0.08113(5) 0.01992(17) Uani 1 1 d . . . P1 P 0.81697(8) 0.15605(3) 0.12015(5) 0.01256(17) Uani 1 1 d . . . C1 C 0.8881(3) 0.18291(13) 0.23780(19) 0.0165(6) Uani 1 1 d . . . H1A H 0.7998 0.1954 0.2627 0.020 Uiso 1 1 calc R . . H1B H 0.9317 0.1419 0.2710 0.020 Uiso 1 1 calc R . . C2 C 0.9999(3) 0.23920(13) 0.2637(2) 0.0151(6) Uani 1 1 d . . . C3 C 0.9585(3) 0.30813(13) 0.25718(19) 0.0142(6) Uani 1 1 d . . . C4 C 0.7976(3) 0.32879(13) 0.22527(19) 0.0162(6) Uani 1 1 d . . . H4A H 0.7860 0.3743 0.2509 0.019 Uiso 1 1 calc R . . H4B H 0.7365 0.2969 0.2531 0.019 Uiso 1 1 calc R . . P4 P 0.71239(8) 0.33303(3) 0.10357(5) 0.01273(17) Uani 1 1 d . . . C5 C 1.1465(3) 0.22210(14) 0.3037(2) 0.0190(7) Uani 1 1 d . . . H5A H 1.1735 0.1754 0.3106 0.023 Uiso 1 1 calc R . . C6 C 1.2537(3) 0.27107(14) 0.3337(2) 0.0202(7) Uani 1 1 d . . . H6A H 1.3538 0.2582 0.3580 0.024 Uiso 1 1 calc R . . C7 C 1.2131(3) 0.33929(15) 0.3278(2) 0.0195(7) Uani 1 1 d . . . H7A H 1.2850 0.3737 0.3482 0.023 Uiso 1 1 calc R . . C8 C 1.0667(3) 0.35655(14) 0.2919(2) 0.0181(6) Uani 1 1 d . . . H8A H 1.0385 0.4031 0.2907 0.022 Uiso 1 1 calc R . . C9 C 0.6967(3) 0.08018(14) 0.1422(2) 0.0176(6) Uani 1 1 d . . . C10 C 0.5382(3) 0.10735(15) 0.1367(2) 0.0236(7) Uani 1 1 d . . . H10A H 0.4729 0.0701 0.1476 0.035 Uiso 1 1 calc R . . H10B H 0.5006 0.1265 0.0767 0.035 Uiso 1 1 calc R . . H10C H 0.5396 0.1428 0.1823 0.035 Uiso 1 1 calc R . . C11 C 0.6925(3) 0.02167(14) 0.0744(2) 0.0218(7) Uani 1 1 d . . . H11A H 0.6297 -0.0152 0.0894 0.033 Uiso 1 1 calc R . . H11B H 0.7939 0.0046 0.0770 0.033 Uiso 1 1 calc R . . H11C H 0.6511 0.0383 0.0134 0.033 Uiso 1 1 calc R . . C12 C 0.7497(3) 0.04876(14) 0.2367(2) 0.0225(7) Uani 1 1 d . . . H12A H 0.6849 0.0104 0.2443 0.034 Uiso 1 1 calc R . . H12B H 0.7452 0.0833 0.2827 0.034 Uiso 1 1 calc R . . H12C H 0.8526 0.0326 0.2430 0.034 Uiso 1 1 calc R . . C13 C 0.9901(3) 0.12817(14) 0.0790(2) 0.0175(6) Uani 1 1 d . . . C14 C 0.9564(3) 0.09535(15) -0.0142(2) 0.0229(7) Uani 1 1 d . . . H14A H 1.0500 0.0821 -0.0313 0.034 Uiso 1 1 calc R . . H14B H 0.9033 0.1280 -0.0583 0.034 Uiso 1 1 calc R . . H14C H 0.8941 0.0549 -0.0130 0.034 Uiso 1 1 calc R . . C15 C 1.0832(3) 0.07740(15) 0.1452(2) 0.0229(7) Uani 1 1 d . . . H15A H 1.1716 0.0638 0.1223 0.034 Uiso 1 1 calc R . . H15B H 1.0228 0.0371 0.1509 0.034 Uiso 1 1 calc R . . H15C H 1.1145 0.0990 0.2042 0.034 Uiso 1 1 calc R . . C16 C 1.0820(3) 0.19232(15) 0.0704(2) 0.0222(7) Uani 1 1 d . . . H16A H 1.1725 0.1796 0.0492 0.033 Uiso 1 1 calc R . . H16B H 1.1096 0.2146 0.1292 0.033 Uiso 1 1 calc R . . H16C H 1.0224 0.2237 0.0271 0.033 Uiso 1 1 calc R . . C17 C 0.8062(3) 0.41022(14) 0.0617(2) 0.0198(7) Uani 1 1 d . . . C18 C 0.9422(3) 0.38256(15) 0.0289(2) 0.0279(8) Uani 1 1 d . . . H18A H 0.9948 0.4202 0.0066 0.042 Uiso 1 1 calc R . . H18B H 0.9094 0.3498 -0.0199 0.042 Uiso 1 1 calc R . . H18C H 1.0095 0.3600 0.0789 0.042 Uiso 1 1 calc R . . C19 C 0.8588(4) 0.46323(15) 0.1355(2) 0.0294(8) Uani 1 1 d . . . H19A H 0.9059 0.5014 0.1104 0.044 Uiso 1 1 calc R . . H19B H 0.9311 0.4423 0.1847 0.044 Uiso 1 1 calc R . . H19C H 0.7730 0.4799 0.1587 0.044 Uiso 1 1 calc R . . C20 C 0.7039(3) 0.44907(14) -0.0150(2) 0.0241(7) Uani 1 1 d . . . H20A H 0.7583 0.4878 -0.0333 0.036 Uiso 1 1 calc R . . H20B H 0.6159 0.4656 0.0060 0.036 Uiso 1 1 calc R . . H20C H 0.6723 0.4185 -0.0665 0.036 Uiso 1 1 calc R . . C21 C 0.5117(3) 0.35221(14) 0.1106(2) 0.0172(6) Uani 1 1 d . . . C22 C 0.4972(3) 0.41637(15) 0.1666(2) 0.0239(7) Uani 1 1 d . . . H22A H 0.3919 0.4238 0.1683 0.036 Uiso 1 1 calc R . . H22B H 0.5356 0.4558 0.1390 0.036 Uiso 1 1 calc R . . H22C H 0.5546 0.4102 0.2281 0.036 Uiso 1 1 calc R . . C23 C 0.4089(3) 0.35955(15) 0.0173(2) 0.0206(7) Uani 1 1 d . . . H23A H 0.3071 0.3693 0.0245 0.031 Uiso 1 1 calc R . . H23B H 0.4096 0.3171 -0.0165 0.031 Uiso 1 1 calc R . . H23C H 0.4446 0.3969 -0.0156 0.031 Uiso 1 1 calc R . . C24 C 0.4536(3) 0.29119(15) 0.1564(2) 0.0247(7) Uani 1 1 d . . . H24A H 0.3500 0.2995 0.1613 0.037 Uiso 1 1 calc R . . H24B H 0.5153 0.2849 0.2168 0.037 Uiso 1 1 calc R . . H24C H 0.4584 0.2501 0.1205 0.037 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 Pd1 0.01229(15) 0.01060(12) 0.01329(16) 0.00022(7) 0.00285(10) 0.00092(7) Cl1 0.0217(4) 0.0172(4) 0.0158(4) 0.0032(3) 0.0028(3) -0.0004(3) Cl2 0.0232(4) 0.0159(3) 0.0183(5) -0.0036(3) -0.0013(3) -0.0003(3) P1 0.0126(4) 0.0098(3) 0.0156(5) 0.0011(3) 0.0038(3) 0.0015(2) C1 0.0184(16) 0.0138(14) 0.0179(18) 0.0027(11) 0.0052(12) 0.0016(11) C2 0.0179(17) 0.0170(15) 0.0100(18) -0.0006(10) 0.0024(12) -0.0004(10) C3 0.0148(16) 0.0186(15) 0.0088(17) 0.0004(11) 0.0015(12) 0.0023(11) C4 0.0158(16) 0.0136(14) 0.0189(19) -0.0004(11) 0.0030(12) 0.0019(10) P4 0.0135(4) 0.0096(3) 0.0149(5) 0.0001(3) 0.0023(3) 0.0011(2) C5 0.0206(17) 0.0178(15) 0.0177(19) 0.0023(11) 0.0017(13) 0.0040(11) C6 0.0156(17) 0.0272(17) 0.017(2) -0.0006(12) 0.0015(13) 0.0013(11) C7 0.0164(16) 0.0239(16) 0.0171(19) -0.0012(12) 0.0011(13) -0.0048(11) C8 0.0212(17) 0.0174(15) 0.0155(18) -0.0015(11) 0.0027(13) 0.0000(11) C9 0.0165(16) 0.0144(15) 0.0227(19) 0.0013(11) 0.0057(12) -0.0023(11) C10 0.0167(17) 0.0208(16) 0.034(2) 0.0007(13) 0.0080(14) -0.0017(12) C11 0.0227(17) 0.0120(15) 0.031(2) -0.0001(12) 0.0060(14) -0.0030(11) C12 0.0294(18) 0.0156(15) 0.023(2) 0.0061(12) 0.0065(14) -0.0010(12) C13 0.0158(16) 0.0172(15) 0.0205(19) -0.0017(11) 0.0063(13) 0.0013(11) C14 0.0231(18) 0.0217(16) 0.026(2) -0.0008(12) 0.0089(14) 0.0046(12) C15 0.0201(17) 0.0253(17) 0.023(2) 0.0001(13) 0.0039(13) 0.0080(12) C16 0.0157(16) 0.0246(16) 0.029(2) -0.0001(13) 0.0098(13) -0.0017(11) C17 0.0212(17) 0.0131(14) 0.025(2) 0.0029(12) 0.0042(13) -0.0027(11) C18 0.0219(18) 0.0220(17) 0.041(2) 0.0096(14) 0.0080(15) -0.0031(12) C19 0.040(2) 0.0158(16) 0.029(2) 0.0026(13) -0.0004(15) -0.0105(13) C20 0.0314(19) 0.0143(15) 0.026(2) 0.0051(12) 0.0052(14) 0.0002(12) C21 0.0140(16) 0.0198(15) 0.0184(19) -0.0009(11) 0.0050(12) 0.0060(11) C22 0.0236(17) 0.0230(16) 0.024(2) -0.0050(13) 0.0017(14) 0.0076(12) C23 0.0146(16) 0.0271(16) 0.0196(19) -0.0017(12) 0.0020(13) 0.0048(11) C24 0.0197(17) 0.0262(17) 0.030(2) 0.0043(13) 0.0099(14) 0.0026(12) _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 Pd1 P1 2.3094(8) . ? Pd1 P4 2.3288(8) . ? Pd1 Cl2 2.3602(7) . ? Pd1 Cl1 2.3645(8) . ? P1 C1 1.847(3) . ? P1 C13 1.898(3) . ? P1 C9 1.922(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.397(4) . ? C2 C3 1.404(4) . ? C3 C8 1.396(4) . ? C3 C4 1.509(4) . ? C4 P4 1.853(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? P4 C21 1.900(3) . ? P4 C17 1.914(3) . ? C5 C6 1.383(4) . ? C5 H5A 0.9500 . ? C6 C7 1.389(4) . ? C6 H6A 0.9500 . ? C7 C8 1.382(4) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C10 1.533(4) . ? C9 C11 1.537(4) . ? C9 C12 1.545(4) . ? 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 1.527(4) . ? C13 C16 1.536(4) . ? C13 C15 1.542(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.532(4) . ? C17 C19 1.533(4) . ? C17 C20 1.538(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C24 1.534(4) . ? C21 C23 1.538(4) . ? C21 C22 1.540(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Pd1 P4 101.88(3) . . ? P1 Pd1 Cl2 88.38(3) . . ? P4 Pd1 Cl2 162.26(3) . . ? P1 Pd1 Cl1 162.72(3) . . ? P4 Pd1 Cl1 89.97(3) . . ? Cl2 Pd1 Cl1 83.60(3) . . ? C1 P1 C13 104.23(13) . . ? C1 P1 C9 98.95(13) . . ? C13 P1 C9 112.30(12) . . ? C1 P1 Pd1 119.34(9) . . ? C13 P1 Pd1 105.55(10) . . ? C9 P1 Pd1 116.04(9) . . ? C2 C1 P1 123.3(2) . . ? C2 C1 H1A 106.5 . . ? P1 C1 H1A 106.5 . . ? C2 C1 H1B 106.5 . . ? P1 C1 H1B 106.5 . . ? H1A C1 H1B 106.5 . . ? C5 C2 C3 118.9(3) . . ? C5 C2 C1 118.6(2) . . ? C3 C2 C1 122.1(2) . . ? C8 C3 C2 118.1(3) . . ? C8 C3 C4 120.5(2) . . ? C2 C3 C4 120.9(2) . . ? C3 C4 P4 121.1(2) . . ? C3 C4 H4A 107.0 . . ? P4 C4 H4A 107.0 . . ? C3 C4 H4B 107.0 . . ? P4 C4 H4B 107.0 . . ? H4A C4 H4B 106.8 . . ? C4 P4 C21 99.71(13) . . ? C4 P4 C17 103.85(13) . . ? C21 P4 C17 111.48(12) . . ? C4 P4 Pd1 119.37(9) . . ? C21 P4 Pd1 105.33(9) . . ? C17 P4 Pd1 115.97(10) . . ? C6 C5 C2 122.0(3) . . ? C6 C5 H5A 119.0 . . ? C2 C5 H5A 119.0 . . ? C5 C6 C7 119.2(3) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C8 C7 C6 119.2(3) . . ? C8 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C7 C8 C3 122.5(3) . . ? C7 C8 H8A 118.7 . . ? C3 C8 H8A 118.7 . . ? C10 C9 C11 109.2(2) . . ? C10 C9 C12 107.7(2) . . ? C11 C9 C12 106.4(2) . . ? C10 C9 P1 106.88(18) . . ? C11 C9 P1 113.6(2) . . ? C12 C9 P1 112.85(19) . . ? 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 C16 106.1(2) . . ? C14 C13 C15 108.0(2) . . ? C16 C13 C15 110.3(2) . . ? C14 C13 P1 113.6(2) . . ? C16 C13 P1 107.45(19) . . ? C15 C13 P1 111.2(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 108.9(2) . . ? C18 C17 C20 109.9(3) . . ? C19 C17 C20 105.5(2) . . ? C18 C17 P4 106.03(18) . . ? C19 C17 P4 113.1(2) . . ? C20 C17 P4 113.47(19) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C24 C21 C23 106.6(2) . . ? C24 C21 C22 108.3(2) . . ? C23 C21 C22 108.9(2) . . ? C24 C21 P4 107.40(19) . . ? C23 C21 P4 112.6(2) . . ? C22 C21 P4 112.7(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P4 Pd1 P1 C1 -0.22(11) . . . . ? Cl2 Pd1 P1 C1 -165.61(11) . . . . ? Cl1 Pd1 P1 C1 132.18(12) . . . . ? P4 Pd1 P1 C13 -116.91(9) . . . . ? Cl2 Pd1 P1 C13 77.69(9) . . . . ? Cl1 Pd1 P1 C13 15.48(14) . . . . ? P4 Pd1 P1 C9 118.03(10) . . . . ? Cl2 Pd1 P1 C9 -47.37(10) . . . . ? Cl1 Pd1 P1 C9 -109.58(13) . . . . ? C13 P1 C1 C2 59.8(3) . . . . ? C9 P1 C1 C2 175.7(2) . . . . ? Pd1 P1 C1 C2 -57.5(3) . . . . ? P1 C1 C2 C5 -106.3(3) . . . . ? P1 C1 C2 C3 80.2(3) . . . . ? C5 C2 C3 C8 -0.4(4) . . . . ? C1 C2 C3 C8 173.1(3) . . . . ? C5 C2 C3 C4 -172.3(3) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C8 C3 C4 P4 106.1(3) . . . . ? C2 C3 C4 P4 -82.2(3) . . . . ? C3 C4 P4 C21 174.5(2) . . . . ? C3 C4 P4 C17 -70.4(2) . . . . ? C3 C4 P4 Pd1 60.6(2) . . . . ? P1 Pd1 P4 C4 -1.34(11) . . . . ? Cl2 Pd1 P4 C4 122.87(13) . . . . ? Cl1 Pd1 P4 C4 -168.67(10) . . . . ? P1 Pd1 P4 C21 -112.14(10) . . . . ? Cl2 Pd1 P4 C21 12.07(14) . . . . ? Cl1 Pd1 P4 C21 80.53(10) . . . . ? P1 Pd1 P4 C17 124.09(10) . . . . ? Cl2 Pd1 P4 C17 -111.70(13) . . . . ? Cl1 Pd1 P4 C17 -43.24(10) . . . . ? C3 C2 C5 C6 -2.8(5) . . . . ? C1 C2 C5 C6 -176.5(3) . . . . ? C2 C5 C6 C7 3.1(5) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C3 -3.0(5) . . . . ? C2 C3 C8 C7 3.3(4) . . . . ? C4 C3 C8 C7 175.2(3) . . . . ? C1 P1 C9 C10 93.1(2) . . . . ? C13 P1 C9 C10 -157.4(2) . . . . ? Pd1 P1 C9 C10 -35.9(2) . . . . ? C1 P1 C9 C11 -146.3(2) . . . . ? C13 P1 C9 C11 -36.8(2) . . . . ? Pd1 P1 C9 C11 84.7(2) . . . . ? C1 P1 C9 C12 -25.1(2) . . . . ? C13 P1 C9 C12 84.4(2) . . . . ? Pd1 P1 C9 C12 -154.09(17) . . . . ? C1 P1 C13 C14 172.9(2) . . . . ? C9 P1 C13 C14 66.8(2) . . . . ? Pd1 P1 C13 C14 -60.5(2) . . . . ? C1 P1 C13 C16 -69.9(2) . . . . ? C9 P1 C13 C16 -176.1(2) . . . . ? Pd1 P1 C13 C16 56.6(2) . . . . ? C1 P1 C13 C15 50.8(2) . . . . ? C9 P1 C13 C15 -55.3(2) . . . . ? Pd1 P1 C13 C15 177.35(17) . . . . ? C4 P4 C17 C18 92.2(2) . . . . ? C21 P4 C17 C18 -161.3(2) . . . . ? Pd1 P4 C17 C18 -40.8(2) . . . . ? C4 P4 C17 C19 -27.0(2) . . . . ? C21 P4 C17 C19 79.5(2) . . . . ? Pd1 P4 C17 C19 -159.98(18) . . . . ? C4 P4 C17 C20 -147.0(2) . . . . ? C21 P4 C17 C20 -40.5(2) . . . . ? Pd1 P4 C17 C20 80.0(2) . . . . ? C4 P4 C21 C24 -63.4(2) . . . . ? C17 P4 C21 C24 -172.5(2) . . . . ? Pd1 P4 C21 C24 60.9(2) . . . . ? C4 P4 C21 C23 179.6(2) . . . . ? C17 P4 C21 C23 70.4(2) . . . . ? Pd1 P4 C21 C23 -56.2(2) . . . . ? C4 P4 C21 C22 55.8(2) . . . . ? C17 P4 C21 C22 -53.4(2) . . . . ? Pd1 P4 C21 C22 -179.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.785 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.082 # Attachment '- [BDTBPMBH2][BF4]2 .cif' data_[BDTBPMBH2][BF4]2 _database_code_depnum_ccdc_archive 'CCDC 774481' #TrackingRef '- [BDTBPMBH2][BF4]2 .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H46 P2.(B F4)2' _chemical_formula_sum 'C24 H46 B2 F8 P2' _chemical_formula_weight 570.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.722(2) _cell_length_b 15.101(4) _cell_length_c 24.950(7) _cell_angle_alpha 90.779(7) _cell_angle_beta 97.485(9) _cell_angle_gamma 92.145(10) _cell_volume 2882.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8894 _cell_measurement_theta_min 2.1097 _cell_measurement_theta_max 28.6648 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5514 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17527 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0874 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.37 _reflns_number_total 9426 _reflns_number_gt 7615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0639P)^2^+19.2446P] 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 9426 _refine_ls_number_parameters 666 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.2225 _refine_ls_wR_factor_gt 0.2107 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.27722(17) -0.11074(9) 0.86571(5) 0.0158(3) Uani 1 1 d D . . H1 H 0.411(4) -0.145(3) 0.8939(16) 0.007(12) Uiso 1 1 d D . . C1 C 0.2385(6) -0.1527(3) 0.79590(19) 0.0151(10) Uani 1 1 d . . . H1A H 0.1463 -0.2005 0.7930 0.018 Uiso 1 1 calc R . . H1B H 0.1953 -0.1043 0.7720 0.018 Uiso 1 1 calc R . . C2 C 0.4024(7) -0.1886(3) 0.7766(2) 0.0155(11) Uani 1 1 d . . . C3 C 0.4783(7) -0.1554(3) 0.7324(2) 0.0162(11) Uani 1 1 d . . . C4 C 0.4022(7) -0.0836(3) 0.69548(19) 0.0151(10) Uani 1 1 d . . . H4A H 0.4891 -0.0335 0.6964 0.018 Uiso 1 1 calc R . . H4B H 0.2975 -0.0614 0.7095 0.018 Uiso 1 1 calc R . . P4 P 0.34158(17) -0.12117(9) 0.62567(5) 0.0148(3) Uani 1 1 d D . . H4 H 0.476(4) -0.157(3) 0.609(2) 0.018(14) Uiso 1 1 d D . . C5 C 0.6336(7) -0.1908(4) 0.7207(2) 0.0196(11) Uani 1 1 d . . . H5A H 0.6892 -0.1663 0.6922 0.024 Uiso 1 1 calc R . . C6 C 0.7097(7) -0.2607(4) 0.7493(2) 0.0239(12) Uani 1 1 d . . . H6A H 0.8153 -0.2839 0.7404 0.029 Uiso 1 1 calc R . . C7 C 0.6281(7) -0.2963(4) 0.7912(2) 0.0236(12) Uani 1 1 d . . . H7A H 0.6763 -0.3452 0.8106 0.028 Uiso 1 1 calc R . . C8 C 0.4778(7) -0.2604(4) 0.8045(2) 0.0231(12) Uani 1 1 d . . . H8A H 0.4238 -0.2849 0.8334 0.028 Uiso 1 1 calc R . . C9 C 0.3699(7) 0.0039(3) 0.87077(19) 0.0160(11) Uani 1 1 d . . . C10 C 0.4904(8) 0.0151(4) 0.8266(2) 0.0251(13) Uani 1 1 d . . . H10A H 0.5412 0.0757 0.8284 0.038 Uiso 1 1 calc R . . H10B H 0.4225 0.0038 0.7910 0.038 Uiso 1 1 calc R . . H10C H 0.5842 -0.0271 0.8324 0.038 Uiso 1 1 calc R . . C11 C 0.2248(7) 0.0727(4) 0.8628(2) 0.0220(12) Uani 1 1 d . . . H11A H 0.2785 0.1327 0.8656 0.033 Uiso 1 1 calc R . . H11B H 0.1474 0.0652 0.8907 0.033 Uiso 1 1 calc R . . H11C H 0.1568 0.0637 0.8270 0.033 Uiso 1 1 calc R . . C12 C 0.4795(7) 0.0171(4) 0.9266(2) 0.0237(12) Uani 1 1 d . . . H12A H 0.5299 0.0778 0.9300 0.036 Uiso 1 1 calc R . . H12B H 0.5737 -0.0249 0.9303 0.036 Uiso 1 1 calc R . . H12C H 0.4047 0.0070 0.9550 0.036 Uiso 1 1 calc R . . C13 C 0.0821(7) -0.1352(4) 0.8992(2) 0.0215(12) Uani 1 1 d . . . C14 C -0.0829(7) -0.1002(4) 0.8668(2) 0.0251(13) Uani 1 1 d . . . H14A H -0.1842 -0.1146 0.8855 0.038 Uiso 1 1 calc R . . H14B H -0.1004 -0.1279 0.8307 0.038 Uiso 1 1 calc R . . H14C H -0.0695 -0.0358 0.8636 0.038 Uiso 1 1 calc R . . C15 C 0.1095(8) -0.0961(4) 0.9569(2) 0.0272(13) Uani 1 1 d . . . H15A H 0.0057 -0.1098 0.9746 0.041 Uiso 1 1 calc R . . H15B H 0.1285 -0.0317 0.9556 0.041 Uiso 1 1 calc R . . H15C H 0.2117 -0.1219 0.9774 0.041 Uiso 1 1 calc R . . C16 C 0.0647(8) -0.2376(4) 0.9021(2) 0.0271(13) Uani 1 1 d . . . H16A H -0.0376 -0.2543 0.9197 0.041 Uiso 1 1 calc R . . H16B H 0.1700 -0.2598 0.9230 0.041 Uiso 1 1 calc R . . H16C H 0.0508 -0.2633 0.8655 0.041 Uiso 1 1 calc R . . C17 C 0.1754(7) -0.2128(4) 0.6208(2) 0.0189(11) Uani 1 1 d . . . C18 C 0.0287(7) -0.1912(4) 0.6544(2) 0.0243(12) Uani 1 1 d . . . H18A H -0.0581 -0.2406 0.6514 0.036 Uiso 1 1 calc R . . H18B H -0.0274 -0.1373 0.6409 0.036 Uiso 1 1 calc R . . H18C H 0.0780 -0.1819 0.6924 0.036 Uiso 1 1 calc R . . C19 C 0.2679(7) -0.2963(4) 0.6419(2) 0.0249(12) Uani 1 1 d . . . H19A H 0.1827 -0.3464 0.6399 0.037 Uiso 1 1 calc R . . H19B H 0.3202 -0.2861 0.6795 0.037 Uiso 1 1 calc R . . H19C H 0.3597 -0.3096 0.6197 0.037 Uiso 1 1 calc R . . C20 C 0.0982(8) -0.2306(4) 0.5617(2) 0.0254(13) Uani 1 1 d . . . H20A H 0.0102 -0.2795 0.5598 0.038 Uiso 1 1 calc R . . H20B H 0.1915 -0.2466 0.5407 0.038 Uiso 1 1 calc R . . H20C H 0.0434 -0.1772 0.5468 0.038 Uiso 1 1 calc R . . C21 C 0.2960(7) -0.0246(4) 0.5819(2) 0.0181(11) Uani 1 1 d . . . C22 C 0.2950(8) -0.0511(4) 0.5222(2) 0.0268(13) Uani 1 1 d . . . H22A H 0.2701 0.0007 0.4996 0.040 Uiso 1 1 calc R . . H22B H 0.2046 -0.0978 0.5121 0.040 Uiso 1 1 calc R . . H22C H 0.4094 -0.0730 0.5168 0.040 Uiso 1 1 calc R . . C23 C 0.4491(7) 0.0428(4) 0.5980(2) 0.0250(13) Uani 1 1 d . . . H23A H 0.4322 0.0959 0.5760 0.038 Uiso 1 1 calc R . . H23B H 0.5590 0.0163 0.5920 0.038 Uiso 1 1 calc R . . H23C H 0.4536 0.0592 0.6363 0.038 Uiso 1 1 calc R . . C24 C 0.1225(7) 0.0165(4) 0.5909(2) 0.0257(13) Uani 1 1 d . . . H24A H 0.1018 0.0672 0.5671 0.039 Uiso 1 1 calc R . . H24B H 0.1287 0.0364 0.6286 0.039 Uiso 1 1 calc R . . H24C H 0.0266 -0.0279 0.5826 0.039 Uiso 1 1 calc R . . P31 P 0.26918(17) -0.38397(9) 0.36865(5) 0.0146(3) Uani 1 1 d D . . H31 H 0.395(5) -0.336(3) 0.396(2) 0.026(16) Uiso 1 1 d D . . C31 C 0.2349(7) -0.3395(4) 0.3007(2) 0.0170(11) Uani 1 1 d . . . H31A H 0.1766 -0.3860 0.2756 0.020 Uiso 1 1 calc R . . H31B H 0.1553 -0.2896 0.3005 0.020 Uiso 1 1 calc R . . C32 C 0.4040(6) -0.3069(3) 0.2799(2) 0.0152(11) Uani 1 1 d . . . C33 C 0.4594(6) -0.3386(3) 0.2326(2) 0.0151(10) Uani 1 1 d . . . C34 C 0.3587(7) -0.4074(3) 0.19455(19) 0.0159(11) Uani 1 1 d . . . H34A H 0.2500 -0.4256 0.2092 0.019 Uiso 1 1 calc R . . H34B H 0.4299 -0.4604 0.1934 0.019 Uiso 1 1 calc R . . P34 P 0.30191(17) -0.36879(9) 0.12580(5) 0.0155(3) Uani 1 1 d D . . H34 H 0.434(5) -0.319(4) 0.116(3) 0.05(2) Uiso 1 1 d D . . C35 C 0.6225(7) -0.3071(4) 0.2195(2) 0.0203(12) Uani 1 1 d . . . H35A H 0.6643 -0.3309 0.1884 0.024 Uiso 1 1 calc R . . C36 C 0.7234(7) -0.2429(4) 0.2501(2) 0.0230(12) Uani 1 1 d . . . H36A H 0.8328 -0.2227 0.2403 0.028 Uiso 1 1 calc R . . C37 C 0.6618(7) -0.2080(4) 0.2959(2) 0.0244(12) Uani 1 1 d . . . H37A H 0.7272 -0.1622 0.3168 0.029 Uiso 1 1 calc R . . C38 C 0.5056(7) -0.2404(3) 0.3106(2) 0.0190(11) Uani 1 1 d . . . H38A H 0.4658 -0.2171 0.3422 0.023 Uiso 1 1 calc R . . C39 C 0.0749(7) -0.3636(4) 0.4023(2) 0.0209(12) Uani 1 1 d . . . C40 C -0.0931(7) -0.3983(4) 0.3677(2) 0.0255(13) Uani 1 1 d . . . H40A H -0.1939 -0.3862 0.3865 0.038 Uiso 1 1 calc R . . H40B H -0.0875 -0.4623 0.3617 0.038 Uiso 1 1 calc R . . H40C H -0.1055 -0.3685 0.3328 0.038 Uiso 1 1 calc R . . C41 C 0.0692(7) -0.2620(4) 0.4100(2) 0.0237(12) Uani 1 1 d . . . H41A H -0.0328 -0.2478 0.4277 0.036 Uiso 1 1 calc R . . H41B H 0.0607 -0.2338 0.3746 0.036 Uiso 1 1 calc R . . H41C H 0.1760 -0.2399 0.4325 0.036 Uiso 1 1 calc R . . C42 C 0.0936(8) -0.4065(4) 0.4584(2) 0.0254(13) Uani 1 1 d . . . H42A H -0.0101 -0.3952 0.4759 0.038 Uiso 1 1 calc R . . H42B H 0.1978 -0.3810 0.4807 0.038 Uiso 1 1 calc R . . H42C H 0.1049 -0.4706 0.4542 0.038 Uiso 1 1 calc R . . C43 C 0.3492(7) -0.4979(3) 0.3699(2) 0.0166(11) Uani 1 1 d . . . C44 C 0.4601(8) -0.5095(4) 0.4251(2) 0.0248(13) Uani 1 1 d . . . H44A H 0.5049 -0.5694 0.4270 0.037 Uiso 1 1 calc R . . H44B H 0.3878 -0.5006 0.4540 0.037 Uiso 1 1 calc R . . H44C H 0.5584 -0.4659 0.4293 0.037 Uiso 1 1 calc R . . C45 C 0.1987(7) -0.5679(4) 0.3609(2) 0.0225(12) Uani 1 1 d . . . H45A H 0.2464 -0.6272 0.3620 0.034 Uiso 1 1 calc R . . H45B H 0.1301 -0.5595 0.3256 0.034 Uiso 1 1 calc R . . H45C H 0.1235 -0.5618 0.3894 0.034 Uiso 1 1 calc R . . C46 C 0.4638(7) -0.5066(4) 0.3245(2) 0.0219(12) Uani 1 1 d . . . H46A H 0.5087 -0.5664 0.3243 0.033 Uiso 1 1 calc R . . H46B H 0.5619 -0.4630 0.3305 0.033 Uiso 1 1 calc R . . H46C H 0.3940 -0.4960 0.2896 0.033 Uiso 1 1 calc R . . C47 C 0.1182(7) -0.2952(4) 0.1201(2) 0.0185(11) Uani 1 1 d . . . C48 C -0.0582(7) -0.3471(4) 0.1174(2) 0.0283(14) Uani 1 1 d . . . H48A H -0.1533 -0.3055 0.1145 0.042 Uiso 1 1 calc R . . H48B H -0.0602 -0.3817 0.1503 0.042 Uiso 1 1 calc R . . H48C H -0.0735 -0.3871 0.0857 0.042 Uiso 1 1 calc R . . C49 C 0.1217(8) -0.2378(4) 0.0698(2) 0.0273(13) Uani 1 1 d . . . H49A H 0.0233 -0.1982 0.0668 0.041 Uiso 1 1 calc R . . H49B H 0.1124 -0.2761 0.0375 0.041 Uiso 1 1 calc R . . H49C H 0.2317 -0.2024 0.0731 0.041 Uiso 1 1 calc R . . C50 C 0.1410(8) -0.2338(4) 0.1706(2) 0.0306(14) Uani 1 1 d . . . H50A H 0.0438 -0.1935 0.1685 0.046 Uiso 1 1 calc R . . H50B H 0.2515 -0.1992 0.1722 0.046 Uiso 1 1 calc R . . H50C H 0.1421 -0.2696 0.2030 0.046 Uiso 1 1 calc R . . C51 C 0.2877(7) -0.4649(4) 0.0792(2) 0.0218(12) Uani 1 1 d . . . C52 C 0.1638(8) -0.5375(4) 0.0966(2) 0.0284(13) Uani 1 1 d . . . H52A H 0.1578 -0.5882 0.0714 0.043 Uiso 1 1 calc R . . H52B H 0.0469 -0.5142 0.0964 0.043 Uiso 1 1 calc R . . H52C H 0.2074 -0.5564 0.1331 0.043 Uiso 1 1 calc R . . C53 C 0.4766(8) -0.4965(5) 0.0822(3) 0.0385(16) Uani 1 1 d . . . H53A H 0.4788 -0.5480 0.0580 0.058 Uiso 1 1 calc R . . H53B H 0.5184 -0.5129 0.1194 0.058 Uiso 1 1 calc R . . H53C H 0.5525 -0.4485 0.0711 0.058 Uiso 1 1 calc R . . C54 C 0.2256(8) -0.4372(4) 0.0206(2) 0.0262(13) Uani 1 1 d . . . H54A H 0.2193 -0.4892 -0.0036 0.039 Uiso 1 1 calc R . . H54B H 0.3085 -0.3926 0.0094 0.039 Uiso 1 1 calc R . . H54C H 0.1098 -0.4122 0.0189 0.039 Uiso 1 1 calc R . . B1 B 0.6245(8) -0.2432(5) 1.0013(3) 0.0247(14) Uani 1 1 d . . . F1 F 0.7150(6) -0.1647(3) 0.99417(18) 0.0536(12) Uani 1 1 d . . . F2 F 0.5766(5) -0.2439(3) 1.05324(16) 0.0458(10) Uani 1 1 d . . . F3 F 0.7310(6) -0.3133(3) 0.99568(16) 0.0489(11) Uani 1 1 d . . . F4 F 0.4772(6) -0.2510(4) 0.9638(2) 0.0796(17) Uani 1 1 d . . . B2 B 0.1116(8) -0.0472(4) 0.2827(2) 0.0195(13) Uani 1 1 d . . . F5 F 0.1001(5) -0.1366(2) 0.29584(16) 0.0379(9) Uani 1 1 d . . . F6 F 0.1972(4) 0.0017(2) 0.32542(14) 0.0361(9) Uani 1 1 d . . . F7 F -0.0587(4) -0.0173(2) 0.27043(14) 0.0348(9) Uani 1 1 d . . . F8 F 0.1979(5) -0.0383(3) 0.23761(16) 0.0474(10) Uani 1 1 d . . . B3 B 0.6306(8) -0.2576(4) 0.5079(3) 0.0237(14) Uani 1 1 d . . . F9 F 0.6247(7) -0.2589(3) 0.56373(19) 0.0697(14) Uani 1 1 d . . . F10 F 0.7212(5) -0.3308(3) 0.4975(2) 0.0642(14) Uani 1 1 d . . . F11 F 0.4611(6) -0.2613(4) 0.4845(3) 0.0863(19) Uani 1 1 d . . . F12 F 0.7162(6) -0.1796(3) 0.5000(3) 0.0844(19) Uani 1 1 d . . . B4 B 0.8618(8) -0.5575(4) 0.2195(3) 0.0208(13) Uani 1 1 d . . . F13 F 0.8148(8) -0.5633(5) 0.1646(2) 0.119(3) Uani 1 1 d . . . F14 F 0.9070(6) -0.6394(3) 0.2351(3) 0.084(2) Uani 1 1 d . . . F15 F 1.0043(5) -0.4978(3) 0.22953(15) 0.0440(10) Uani 1 1 d . . . F16 F 0.7256(9) -0.5311(4) 0.2411(4) 0.140(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 0.0189(7) 0.0170(7) 0.0119(6) 0.0022(5) 0.0033(5) 0.0012(6) C1 0.017(3) 0.019(3) 0.010(2) 0.0026(19) 0.0043(19) 0.000(2) C2 0.019(3) 0.013(3) 0.013(2) -0.0014(19) -0.001(2) 0.000(2) C3 0.016(3) 0.020(3) 0.012(2) 0.000(2) 0.0001(19) -0.001(2) C4 0.019(3) 0.015(3) 0.012(2) 0.0013(19) 0.0026(19) 0.001(2) P4 0.0179(7) 0.0154(7) 0.0116(6) 0.0014(5) 0.0039(5) 0.0015(5) C5 0.022(3) 0.020(3) 0.016(3) 0.000(2) 0.002(2) 0.002(2) C6 0.020(3) 0.028(3) 0.025(3) -0.002(2) 0.002(2) 0.008(2) C7 0.030(3) 0.019(3) 0.022(3) 0.007(2) 0.004(2) 0.011(2) C8 0.031(3) 0.018(3) 0.021(3) 0.004(2) 0.005(2) 0.002(2) C9 0.019(3) 0.016(3) 0.013(2) 0.000(2) 0.000(2) 0.000(2) C10 0.029(3) 0.023(3) 0.023(3) -0.004(2) 0.008(2) -0.011(2) C11 0.027(3) 0.018(3) 0.020(3) 0.000(2) 0.001(2) 0.000(2) C12 0.026(3) 0.022(3) 0.020(3) 0.000(2) -0.004(2) 0.000(2) C13 0.025(3) 0.026(3) 0.015(3) 0.003(2) 0.012(2) 0.000(2) C14 0.013(3) 0.033(3) 0.031(3) 0.001(3) 0.007(2) 0.002(2) C15 0.033(3) 0.031(3) 0.019(3) 0.001(2) 0.011(2) 0.001(3) C16 0.033(3) 0.026(3) 0.023(3) 0.010(2) 0.011(2) -0.001(3) C17 0.022(3) 0.018(3) 0.017(3) 0.001(2) 0.004(2) -0.004(2) C18 0.022(3) 0.024(3) 0.027(3) -0.005(2) 0.008(2) -0.005(2) C19 0.026(3) 0.016(3) 0.031(3) 0.000(2) -0.005(2) 0.000(2) C20 0.030(3) 0.030(3) 0.016(3) -0.003(2) 0.002(2) -0.005(3) C21 0.020(3) 0.022(3) 0.012(3) 0.004(2) 0.003(2) 0.001(2) C22 0.037(3) 0.031(3) 0.013(3) 0.004(2) 0.006(2) -0.003(3) C23 0.029(3) 0.023(3) 0.023(3) 0.007(2) 0.006(2) 0.000(2) C24 0.024(3) 0.025(3) 0.029(3) 0.010(2) 0.005(2) 0.006(2) P31 0.0171(7) 0.0159(7) 0.0111(6) 0.0013(5) 0.0037(5) -0.0010(5) C31 0.020(3) 0.019(3) 0.014(3) 0.000(2) 0.008(2) 0.000(2) C32 0.016(3) 0.014(3) 0.016(3) 0.005(2) 0.004(2) 0.002(2) C33 0.014(3) 0.014(3) 0.017(3) 0.003(2) 0.0032(19) 0.000(2) C34 0.015(3) 0.019(3) 0.013(3) 0.004(2) 0.0028(19) 0.001(2) P34 0.0152(7) 0.0189(7) 0.0126(6) 0.0021(5) 0.0028(5) 0.0010(5) C35 0.016(3) 0.028(3) 0.019(3) 0.003(2) 0.006(2) 0.003(2) C36 0.020(3) 0.030(3) 0.020(3) 0.008(2) 0.006(2) -0.001(2) C37 0.028(3) 0.022(3) 0.023(3) -0.001(2) 0.002(2) -0.009(2) C38 0.023(3) 0.018(3) 0.015(3) -0.001(2) 0.003(2) -0.003(2) C39 0.023(3) 0.025(3) 0.017(3) 0.002(2) 0.008(2) 0.002(2) C40 0.016(3) 0.033(3) 0.029(3) 0.002(3) 0.008(2) -0.002(2) C41 0.026(3) 0.024(3) 0.022(3) 0.003(2) 0.007(2) 0.007(2) C42 0.033(3) 0.026(3) 0.019(3) 0.002(2) 0.012(2) 0.003(3) C43 0.021(3) 0.014(3) 0.015(3) -0.001(2) 0.004(2) -0.001(2) C44 0.036(3) 0.021(3) 0.017(3) 0.009(2) 0.001(2) 0.005(3) C45 0.023(3) 0.017(3) 0.027(3) -0.001(2) -0.001(2) -0.002(2) C46 0.029(3) 0.019(3) 0.018(3) 0.003(2) 0.006(2) 0.007(2) C47 0.019(3) 0.020(3) 0.017(3) 0.004(2) 0.002(2) 0.004(2) C48 0.017(3) 0.041(4) 0.028(3) 0.014(3) 0.003(2) 0.008(3) C49 0.030(3) 0.035(3) 0.018(3) 0.014(2) 0.006(2) 0.007(3) C50 0.039(4) 0.029(3) 0.024(3) -0.002(3) 0.003(3) 0.012(3) C51 0.023(3) 0.025(3) 0.017(3) -0.006(2) 0.001(2) 0.003(2) C52 0.035(3) 0.026(3) 0.023(3) 0.002(2) 0.000(2) -0.004(3) C53 0.035(4) 0.047(4) 0.034(4) -0.015(3) 0.004(3) 0.012(3) C54 0.030(3) 0.034(3) 0.014(3) -0.001(2) 0.001(2) -0.006(3) B1 0.021(3) 0.027(4) 0.025(3) 0.007(3) 0.000(3) -0.001(3) F1 0.060(3) 0.037(2) 0.072(3) 0.009(2) 0.038(2) -0.005(2) F2 0.058(3) 0.037(2) 0.049(2) 0.0123(18) 0.028(2) 0.0087(19) F3 0.062(3) 0.043(2) 0.042(2) -0.0124(18) 0.0026(19) 0.023(2) F4 0.053(3) 0.096(4) 0.078(4) 0.041(3) -0.036(3) -0.008(3) B2 0.020(3) 0.022(3) 0.018(3) 0.003(2) 0.006(2) 0.004(3) F5 0.038(2) 0.0225(19) 0.053(2) 0.0122(17) 0.0049(17) 0.0000(16) F6 0.0267(19) 0.041(2) 0.038(2) -0.0055(17) -0.0049(15) -0.0025(16) F7 0.0268(19) 0.043(2) 0.033(2) -0.0036(16) -0.0054(15) 0.0143(16) F8 0.056(3) 0.051(3) 0.042(2) 0.0067(19) 0.0317(19) 0.001(2) B3 0.022(3) 0.026(4) 0.024(3) -0.001(3) 0.008(3) 0.001(3) F9 0.094(4) 0.074(3) 0.046(3) 0.000(2) 0.026(3) 0.017(3) F10 0.038(2) 0.044(3) 0.114(4) -0.026(3) 0.027(2) 0.001(2) F11 0.030(2) 0.097(4) 0.125(5) -0.048(4) -0.016(3) 0.013(3) F12 0.054(3) 0.048(3) 0.143(5) 0.044(3) -0.016(3) -0.005(2) B4 0.014(3) 0.022(3) 0.027(3) 0.000(3) 0.002(2) 0.005(3) F13 0.113(5) 0.154(6) 0.066(4) 0.053(4) -0.054(3) -0.083(5) F14 0.041(3) 0.032(2) 0.166(6) 0.015(3) -0.038(3) 0.001(2) F15 0.045(2) 0.047(2) 0.036(2) 0.0081(18) -0.0004(17) -0.0268(19) F16 0.113(5) 0.066(4) 0.268(10) -0.068(5) 0.143(6) -0.032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.829(5) . ? P1 C13 1.844(5) . ? P1 C9 1.844(5) . ? P1 H1 1.299(5) . ? C1 C2 1.527(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C8 1.401(7) . ? C2 C3 1.404(7) . ? C3 C5 1.394(8) . ? C3 C4 1.517(7) . ? C4 P4 1.821(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? P4 C17 1.843(5) . ? P4 C21 1.852(5) . ? P4 H4 1.300(5) . ? C5 C6 1.388(8) . ? C5 H5A 0.9500 . ? C6 C7 1.393(8) . ? C6 H6A 0.9500 . ? C7 C8 1.377(8) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C10 1.539(7) . ? C9 C12 1.539(7) . ? C9 C11 1.553(7) . ? 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 1.532(8) . ? C13 C15 1.535(7) . ? C13 C16 1.550(8) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C20 1.534(7) . ? C17 C18 1.536(7) . ? C17 C19 1.538(7) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.535(7) . ? C21 C24 1.539(8) . ? C21 C23 1.540(8) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? P31 C31 1.823(5) . ? P31 C39 1.846(5) . ? P31 C43 1.848(5) . ? P31 H31 1.300(5) . ? C31 C32 1.534(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.391(7) . ? C32 C38 1.406(7) . ? C33 C35 1.410(7) . ? C33 C34 1.519(7) . ? C34 P34 1.824(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? P34 C47 1.827(5) . ? P34 C51 1.839(6) . ? P34 H34 1.300(5) . ? C35 C36 1.378(8) . ? C35 H35A 0.9500 . ? C36 C37 1.397(8) . ? C36 H36A 0.9500 . ? C37 C38 1.380(7) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 C40 1.532(8) . ? C39 C42 1.543(7) . ? C39 C41 1.547(8) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 C46 1.533(7) . ? C43 C45 1.534(7) . ? C43 C44 1.540(7) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 C49 1.536(7) . ? C47 C48 1.539(7) . ? C47 C50 1.542(8) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.532(8) . ? C51 C53 1.545(8) . ? C51 C54 1.546(7) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? B1 F4 1.375(8) . ? B1 F1 1.379(8) . ? B1 F3 1.381(8) . ? B1 F2 1.394(8) . ? B2 F6 1.370(7) . ? B2 F8 1.385(7) . ? B2 F5 1.395(7) . ? B2 F7 1.404(7) . ? B3 F12 1.358(8) . ? B3 F11 1.361(8) . ? B3 F10 1.370(8) . ? B3 F9 1.400(8) . ? B4 F16 1.314(8) . ? B4 F14 1.346(8) . ? B4 F13 1.372(8) . ? B4 F15 1.391(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C13 109.4(2) . . ? C1 P1 C9 112.4(2) . . ? C13 P1 C9 117.6(2) . . ? C1 P1 H1 113(2) . . ? C13 P1 H1 109(2) . . ? C9 P1 H1 95(2) . . ? C2 C1 P1 112.8(3) . . ? C2 C1 H1A 109.0 . . ? P1 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? P1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C8 C2 C3 118.9(5) . . ? C8 C2 C1 116.9(4) . . ? C3 C2 C1 124.2(4) . . ? C5 C3 C2 118.5(5) . . ? C5 C3 C4 116.9(4) . . ? C2 C3 C4 124.6(5) . . ? C3 C4 P4 113.5(3) . . ? C3 C4 H4A 108.9 . . ? P4 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? P4 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 P4 C17 111.2(2) . . ? C4 P4 C21 109.8(2) . . ? C17 P4 C21 117.8(2) . . ? C4 P4 H4 109(2) . . ? C17 P4 H4 104(2) . . ? C21 P4 H4 105(2) . . ? C6 C5 C3 122.2(5) . . ? C6 C5 H5A 118.9 . . ? C3 C5 H5A 118.9 . . ? C5 C6 C7 118.7(5) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C8 C7 C6 119.9(5) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C2 121.6(5) . . ? C7 C8 H8A 119.2 . . ? C2 C8 H8A 119.2 . . ? C10 C9 C12 109.0(4) . . ? C10 C9 C11 109.5(4) . . ? C12 C9 C11 110.5(4) . . ? C10 C9 P1 107.8(4) . . ? C12 C9 P1 108.3(4) . . ? C11 C9 P1 111.7(4) . . ? 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 C15 110.9(5) . . ? C14 C13 C16 109.6(5) . . ? C15 C13 C16 108.8(4) . . ? C14 C13 P1 111.4(4) . . ? C15 C13 P1 109.9(4) . . ? C16 C13 P1 106.1(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C20 C17 C18 109.7(4) . . ? C20 C17 C19 108.0(5) . . ? C18 C17 C19 110.6(4) . . ? C20 C17 P4 110.4(4) . . ? C18 C17 P4 110.6(4) . . ? C19 C17 P4 107.4(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C24 110.8(5) . . ? C22 C21 C23 108.4(4) . . ? C24 C21 C23 110.0(5) . . ? C22 C21 P4 110.5(4) . . ? C24 C21 P4 111.3(3) . . ? C23 C21 P4 105.7(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C31 P31 C39 108.8(2) . . ? C31 P31 C43 112.8(2) . . ? C39 P31 C43 117.5(2) . . ? C31 P31 H31 107(3) . . ? C39 P31 H31 105(3) . . ? C43 P31 H31 105(3) . . ? C32 C31 P31 113.7(4) . . ? C32 C31 H31A 108.8 . . ? P31 C31 H31A 108.8 . . ? C32 C31 H31B 108.8 . . ? P31 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C33 C32 C38 119.1(5) . . ? C33 C32 C31 123.7(5) . . ? C38 C32 C31 117.1(4) . . ? C32 C33 C35 118.2(5) . . ? C32 C33 C34 124.6(4) . . ? C35 C33 C34 117.1(4) . . ? C33 C34 P34 113.9(3) . . ? C33 C34 H34A 108.8 . . ? P34 C34 H34A 108.8 . . ? C33 C34 H34B 108.8 . . ? P34 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C34 P34 C47 112.4(2) . . ? C34 P34 C51 108.4(2) . . ? C47 P34 C51 117.8(3) . . ? C34 P34 H34 106(3) . . ? C47 P34 H34 105(3) . . ? C51 P34 H34 107(3) . . ? C36 C35 C33 122.5(5) . . ? C36 C35 H35A 118.8 . . ? C33 C35 H35A 118.8 . . ? C35 C36 C37 118.6(5) . . ? C35 C36 H36A 120.7 . . ? C37 C36 H36A 120.7 . . ? C38 C37 C36 119.8(5) . . ? C38 C37 H37A 120.1 . . ? C36 C37 H37A 120.1 . . ? C37 C38 C32 121.5(5) . . ? C37 C38 H38A 119.2 . . ? C32 C38 H38A 119.2 . . ? C40 C39 C42 110.6(5) . . ? C40 C39 C41 109.5(5) . . ? C42 C39 C41 108.7(4) . . ? C40 C39 P31 111.4(4) . . ? C42 C39 P31 110.2(4) . . ? C41 C39 P31 106.5(4) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C46 C43 C45 109.1(4) . . ? C46 C43 C44 109.8(4) . . ? C45 C43 C44 110.8(4) . . ? C46 C43 P31 107.7(3) . . ? C45 C43 P31 112.0(4) . . ? C44 C43 P31 107.4(4) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C49 C47 C48 110.4(4) . . ? C49 C47 C50 108.5(5) . . ? C48 C47 C50 108.6(5) . . ? C49 C47 P34 109.5(4) . . ? C48 C47 P34 111.9(4) . . ? C50 C47 P34 107.8(4) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C47 C49 H49A 109.5 . . ? C47 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C47 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C52 C51 C53 111.5(5) . . ? C52 C51 C54 110.3(4) . . ? C53 C51 C54 108.7(5) . . ? C52 C51 P34 110.5(4) . . ? C53 C51 P34 105.0(4) . . ? C54 C51 P34 110.7(4) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? F4 B1 F1 109.8(5) . . ? F4 B1 F3 110.2(6) . . ? F1 B1 F3 109.4(5) . . ? F4 B1 F2 109.6(5) . . ? F1 B1 F2 109.2(5) . . ? F3 B1 F2 108.7(5) . . ? F6 B2 F8 110.6(5) . . ? F6 B2 F5 110.5(5) . . ? F8 B2 F5 109.3(5) . . ? F6 B2 F7 109.2(5) . . ? F8 B2 F7 109.0(5) . . ? F5 B2 F7 108.3(5) . . ? F12 B3 F11 113.2(6) . . ? F12 B3 F10 113.8(5) . . ? F11 B3 F10 113.9(6) . . ? F12 B3 F9 104.3(6) . . ? F11 B3 F9 105.8(5) . . ? F10 B3 F9 104.5(5) . . ? F16 B4 F14 112.2(6) . . ? F16 B4 F13 107.6(7) . . ? F14 B4 F13 105.9(6) . . ? F16 B4 F15 112.4(6) . . ? F14 B4 F15 110.7(5) . . ? F13 B4 F15 107.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 P1 C1 C2 -144.4(4) . . . . ? C9 P1 C1 C2 83.0(4) . . . . ? P1 C1 C2 C8 61.3(5) . . . . ? P1 C1 C2 C3 -120.0(5) . . . . ? C8 C2 C3 C5 -4.9(7) . . . . ? C1 C2 C3 C5 176.5(5) . . . . ? C8 C2 C3 C4 174.4(5) . . . . ? C1 C2 C3 C4 -4.2(8) . . . . ? C5 C3 C4 P4 62.4(5) . . . . ? C2 C3 C4 P4 -116.9(5) . . . . ? C3 C4 P4 C17 60.1(4) . . . . ? C3 C4 P4 C21 -167.9(3) . . . . ? C2 C3 C5 C6 3.6(8) . . . . ? C4 C3 C5 C6 -175.7(5) . . . . ? C3 C5 C6 C7 -0.3(8) . . . . ? C5 C6 C7 C8 -1.8(9) . . . . ? C6 C7 C8 C2 0.5(9) . . . . ? C3 C2 C8 C7 2.9(8) . . . . ? C1 C2 C8 C7 -178.4(5) . . . . ? C1 P1 C9 C10 -34.2(4) . . . . ? C13 P1 C9 C10 -162.7(4) . . . . ? C1 P1 C9 C12 -152.1(4) . . . . ? C13 P1 C9 C12 79.5(4) . . . . ? C1 P1 C9 C11 86.1(4) . . . . ? C13 P1 C9 C11 -42.4(4) . . . . ? C1 P1 C13 C14 -53.8(5) . . . . ? C9 P1 C13 C14 76.0(5) . . . . ? C1 P1 C13 C15 -177.1(4) . . . . ? C9 P1 C13 C15 -47.3(5) . . . . ? C1 P1 C13 C16 65.4(4) . . . . ? C9 P1 C13 C16 -164.8(3) . . . . ? C4 P4 C17 C20 168.2(4) . . . . ? C21 P4 C17 C20 40.4(5) . . . . ? C4 P4 C17 C18 46.5(4) . . . . ? C21 P4 C17 C18 -81.3(4) . . . . ? C4 P4 C17 C19 -74.3(4) . . . . ? C21 P4 C17 C19 157.9(4) . . . . ? C4 P4 C21 C22 164.3(4) . . . . ? C17 P4 C21 C22 -67.2(4) . . . . ? C4 P4 C21 C24 -72.2(4) . . . . ? C17 P4 C21 C24 56.3(5) . . . . ? C4 P4 C21 C23 47.2(4) . . . . ? C17 P4 C21 C23 175.7(3) . . . . ? C39 P31 C31 C32 149.4(4) . . . . ? C43 P31 C31 C32 -78.4(4) . . . . ? P31 C31 C32 C33 122.5(5) . . . . ? P31 C31 C32 C38 -58.4(6) . . . . ? C38 C32 C33 C35 4.6(7) . . . . ? C31 C32 C33 C35 -176.4(5) . . . . ? C38 C32 C33 C34 -177.3(5) . . . . ? C31 C32 C33 C34 1.7(8) . . . . ? C32 C33 C34 P34 121.0(5) . . . . ? C35 C33 C34 P34 -60.9(6) . . . . ? C33 C34 P34 C47 -76.6(4) . . . . ? C33 C34 P34 C51 151.5(4) . . . . ? C32 C33 C35 C36 -3.6(8) . . . . ? C34 C33 C35 C36 178.1(5) . . . . ? C33 C35 C36 C37 0.2(8) . . . . ? C35 C36 C37 C38 2.3(8) . . . . ? C36 C37 C38 C32 -1.3(8) . . . . ? C33 C32 C38 C37 -2.3(8) . . . . ? C31 C32 C38 C37 178.6(5) . . . . ? C31 P31 C39 C40 52.8(4) . . . . ? C43 P31 C39 C40 -76.9(4) . . . . ? C31 P31 C39 C42 175.8(4) . . . . ? C43 P31 C39 C42 46.2(5) . . . . ? C31 P31 C39 C41 -66.5(4) . . . . ? C43 P31 C39 C41 163.9(3) . . . . ? C31 P31 C43 C46 32.7(4) . . . . ? C39 P31 C43 C46 160.4(3) . . . . ? C31 P31 C43 C45 -87.3(4) . . . . ? C39 P31 C43 C45 40.5(5) . . . . ? C31 P31 C43 C44 150.9(4) . . . . ? C39 P31 C43 C44 -81.4(4) . . . . ? C34 P34 C47 C49 158.1(4) . . . . ? C51 P34 C47 C49 -74.8(5) . . . . ? C34 P34 C47 C48 -79.2(4) . . . . ? C51 P34 C47 C48 47.9(5) . . . . ? C34 P34 C47 C50 40.2(4) . . . . ? C51 P34 C47 C50 167.3(4) . . . . ? C34 P34 C51 C52 53.2(4) . . . . ? C47 P34 C51 C52 -75.8(4) . . . . ? C34 P34 C51 C53 -67.2(4) . . . . ? C47 P34 C51 C53 163.8(4) . . . . ? C34 P34 C51 C54 175.6(4) . . . . ? C47 P34 C51 C54 46.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 1.433 _refine_diff_density_min -1.039 _refine_diff_density_rms 0.100