# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jan Paradies' _publ_contact_author_email jan.paradies@kit.edu loop_ _publ_author_name F.Falk R.Frohlich J.Paradies # Attachment '- fro5854.cif' data_fro5854 _database_code_depnum_ccdc_archive 'CCDC 816638' #TrackingRef '- fro5854.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 B2 F8 N2 P2 Pd' _chemical_formula_weight 950.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 '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 11.5738(2) _cell_length_b 11.8493(2) _cell_length_c 17.8777(3) _cell_angle_alpha 71.202(1) _cell_angle_beta 73.601(1) _cell_angle_gamma 74.227(1) _cell_volume 2181.98(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6267 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8807 _exptl_absorpt_correction_T_max 0.9198 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21445 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 27.85 _reflns_number_total 10073 _reflns_number_gt 9059 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+5.8355P] 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 10073 _refine_ls_number_parameters 534 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Pd Pd 0.69382(2) 0.62140(2) 0.742208(14) 0.02443(8) Uani 1 1 d . . . P1 P 0.63223(7) 0.79836(7) 0.78073(5) 0.02461(16) Uani 1 1 d . . . P2 P 0.50997(7) 0.60745(7) 0.72692(4) 0.02204(15) Uani 1 1 d . . . C1 C 0.4288(3) 0.6080(3) 0.91924(18) 0.0301(7) Uani 1 1 d . . . H1A H 0.5093 0.5792 0.8875 0.036 Uiso 1 1 calc R . . H1B H 0.4055 0.5392 0.9644 0.036 Uiso 1 1 calc R . . C2 C 0.4378(3) 0.7113(3) 0.95332(19) 0.0299(6) Uani 1 1 d . . . H2A H 0.3797 0.7088 1.0054 0.036 Uiso 1 1 calc R . . H2B H 0.5208 0.6972 0.9624 0.036 Uiso 1 1 calc R . . C3 C 0.4095(3) 0.8359(3) 0.89542(19) 0.0289(6) Uani 1 1 d . . . C4 C 0.4729(3) 0.8693(3) 0.81426(19) 0.0253(6) Uani 1 1 d . . . C5 C 0.4084(3) 0.9526(3) 0.7572(2) 0.0297(6) Uani 1 1 d . . . H5 H 0.4490 0.9720 0.7025 0.036 Uiso 1 1 calc R . . C6 C 0.2858(3) 1.0076(3) 0.7789(2) 0.0368(8) Uani 1 1 d . . . C7 C 0.2375(3) 0.9977(3) 0.8609(2) 0.0399(8) Uani 1 1 d . . . H7 H 0.1635 1.0492 0.8775 0.048 Uiso 1 1 calc R . . C8 C 0.2980(3) 0.9126(3) 0.9179(2) 0.0346(7) Uani 1 1 d . . . H8 H 0.2636 0.9059 0.9731 0.042 Uiso 1 1 calc R . . C9 C 0.2035(4) 1.0522(4) 0.7189(3) 0.0484(10) Uani 1 1 d . . . H9A H 0.2542 1.0644 0.6639 0.058 Uiso 1 1 calc R . . H9B H 0.1514 1.1308 0.7242 0.058 Uiso 1 1 calc R . . C10 C 0.1194(4) 0.9598(4) 0.7320(3) 0.0456(9) Uani 1 1 d . . . H10A H 0.0382 0.9855 0.7644 0.055 Uiso 1 1 calc R . . H10B H 0.1084 0.9604 0.6795 0.055 Uiso 1 1 calc R . . C11 C 0.1756(3) 0.8322(3) 0.7746(2) 0.0352(7) Uani 1 1 d . . . C12 C 0.2843(3) 0.7693(3) 0.7366(2) 0.0305(7) Uani 1 1 d . . . H12 H 0.3039 0.7870 0.6798 0.037 Uiso 1 1 calc R . . C13 C 0.3654(3) 0.6803(3) 0.78078(18) 0.0240(6) Uani 1 1 d . . . C14 C 0.3346(3) 0.6535(3) 0.86630(19) 0.0277(6) Uani 1 1 d . . . C15 C 0.2134(3) 0.6956(3) 0.9019(2) 0.0352(7) Uani 1 1 d . . . H15 H 0.1839 0.6631 0.9575 0.042 Uiso 1 1 calc R . . C16 C 0.1359(3) 0.7843(3) 0.8570(2) 0.0385(8) Uani 1 1 d . . . H16 H 0.0551 0.8127 0.8826 0.046 Uiso 1 1 calc R . . C21 C 0.7080(3) 0.7821(3) 0.8617(2) 0.0323(7) Uani 1 1 d . . . C22 C 0.7279(4) 0.8851(4) 0.8737(3) 0.0451(9) Uani 1 1 d . . . H22 H 0.7012 0.9627 0.8409 0.054 Uiso 1 1 calc R . . C23 C 0.7879(4) 0.8730(5) 0.9347(3) 0.0590(13) Uani 1 1 d . . . H23 H 0.8018 0.9425 0.9425 0.071 Uiso 1 1 calc R . . C24 C 0.8264(4) 0.7599(6) 0.9832(3) 0.0603(13) Uani 1 1 d . . . H24 H 0.8665 0.7522 1.0240 0.072 Uiso 1 1 calc R . . C25 C 0.8061(4) 0.6584(5) 0.9719(3) 0.0555(11) Uani 1 1 d . . . H25 H 0.8325 0.5813 1.0053 0.067 Uiso 1 1 calc R . . C26 C 0.7472(3) 0.6679(4) 0.9119(2) 0.0408(8) Uani 1 1 d . . . H26 H 0.7335 0.5976 0.9050 0.049 Uiso 1 1 calc R . . C31 C 0.6977(3) 0.9121(3) 0.6942(2) 0.0318(7) Uani 1 1 d . . . C32 C 0.7905(4) 0.8749(4) 0.6333(2) 0.0422(9) Uani 1 1 d . . . H32 H 0.8170 0.7916 0.6359 0.051 Uiso 1 1 calc R . . C33 C 0.8445(4) 0.9602(4) 0.5684(3) 0.0565(12) Uani 1 1 d . . . H33 H 0.9068 0.9345 0.5271 0.068 Uiso 1 1 calc R . . C34 C 0.8071(5) 1.0818(4) 0.5647(3) 0.0615(13) Uani 1 1 d . . . H34 H 0.8439 1.1391 0.5207 0.074 Uiso 1 1 calc R . . C35 C 0.7162(4) 1.1206(4) 0.6248(3) 0.0536(11) Uani 1 1 d . . . H35 H 0.6912 1.2040 0.6219 0.064 Uiso 1 1 calc R . . C36 C 0.6610(4) 1.0364(3) 0.6898(2) 0.0406(8) Uani 1 1 d . . . H36 H 0.5991 1.0630 0.7310 0.049 Uiso 1 1 calc R . . C41 C 0.5082(3) 0.4438(3) 0.75567(18) 0.0253(6) Uani 1 1 d . . . H41 H 0.5717 0.4102 0.7139 0.030 Uiso 1 1 calc R . . C42 C 0.5431(3) 0.3701(3) 0.8366(2) 0.0324(7) Uani 1 1 d . . . H42A H 0.6214 0.3853 0.8382 0.039 Uiso 1 1 calc R . . H42B H 0.4800 0.3956 0.8809 0.039 Uiso 1 1 calc R . . C43 C 0.5548(4) 0.2350(3) 0.8470(2) 0.0382(8) Uani 1 1 d . . . H43A H 0.6229 0.2085 0.8053 0.046 Uiso 1 1 calc R . . H43B H 0.5737 0.1889 0.8999 0.046 Uiso 1 1 calc R . . C44 C 0.4373(4) 0.2079(3) 0.8409(2) 0.0420(9) Uani 1 1 d . . . H44A H 0.4507 0.1218 0.8430 0.050 Uiso 1 1 calc R . . H44B H 0.3720 0.2232 0.8873 0.050 Uiso 1 1 calc R . . C45 C 0.3964(4) 0.2853(3) 0.7633(2) 0.0389(8) Uani 1 1 d . . . H45A H 0.3162 0.2713 0.7645 0.047 Uiso 1 1 calc R . . H45B H 0.4552 0.2603 0.7172 0.047 Uiso 1 1 calc R . . C46 C 0.3869(3) 0.4206(3) 0.7515(2) 0.0328(7) Uani 1 1 d . . . H46A H 0.3207 0.4485 0.7937 0.039 Uiso 1 1 calc R . . H46B H 0.3669 0.4666 0.6989 0.039 Uiso 1 1 calc R . . C51 C 0.5052(3) 0.6646(3) 0.61807(18) 0.0275(6) Uani 1 1 d . . . H51 H 0.4187 0.6786 0.6140 0.033 Uiso 1 1 calc R . . C52 C 0.5463(4) 0.7883(3) 0.5820(2) 0.0363(8) Uani 1 1 d . . . H52A H 0.4950 0.8452 0.6135 0.044 Uiso 1 1 calc R . . H52B H 0.6317 0.7775 0.5858 0.044 Uiso 1 1 calc R . . C53 C 0.5358(5) 0.8419(4) 0.4932(2) 0.0495(10) Uani 1 1 d . . . H53A H 0.4491 0.8623 0.4900 0.059 Uiso 1 1 calc R . . H53B H 0.5683 0.9169 0.4706 0.059 Uiso 1 1 calc R . . C54 C 0.6066(5) 0.7519(4) 0.4436(2) 0.0479(10) Uani 1 1 d . . . H54A H 0.5934 0.7855 0.3882 0.057 Uiso 1 1 calc R . . H54B H 0.6947 0.7392 0.4412 0.057 Uiso 1 1 calc R . . C55 C 0.5655(4) 0.6314(3) 0.4803(2) 0.0412(9) Uani 1 1 d . . . H55A H 0.6136 0.5746 0.4480 0.049 Uiso 1 1 calc R . . H55B H 0.4788 0.6432 0.4790 0.049 Uiso 1 1 calc R . . C56 C 0.5817(4) 0.5767(3) 0.5678(2) 0.0371(8) Uani 1 1 d . . . H56A H 0.5549 0.4986 0.5902 0.045 Uiso 1 1 calc R . . H56B H 0.6686 0.5624 0.5693 0.045 Uiso 1 1 calc R . . N61 N 0.7803(3) 0.4733(3) 0.69415(19) 0.0345(6) Uani 1 1 d . . . C62 C 0.8553(4) 0.4036(3) 0.6695(2) 0.0399(8) Uani 1 1 d . . . C63 C 0.9523(5) 0.3129(5) 0.6376(3) 0.0688(15) Uani 1 1 d . . . H63A H 1.0308 0.3194 0.6436 0.103 Uiso 1 1 calc R . . H63B H 0.9544 0.3266 0.5808 0.103 Uiso 1 1 calc R . . H63C H 0.9364 0.2323 0.6672 0.103 Uiso 1 1 calc R . . N71 N 0.8696(3) 0.6120(3) 0.7549(2) 0.0368(6) Uani 1 1 d . . . C72 C 0.9626(3) 0.5797(4) 0.7699(2) 0.0406(8) Uani 1 1 d . . . C73 C 1.0815(4) 0.5377(5) 0.7917(3) 0.0615(13) Uani 1 1 d . . . H73A H 1.0709 0.5267 0.8492 0.092 Uiso 1 1 calc R . . H73B H 1.1326 0.5973 0.7617 0.092 Uiso 1 1 calc R . . H73C H 1.1207 0.4608 0.7787 0.092 Uiso 1 1 calc R . . B1 B 0.1420(7) 0.6147(6) 0.5693(4) 0.0663(15) Uani 1 1 d . . . F11 F 0.0289(4) 0.6808(5) 0.5648(3) 0.1289(18) Uani 1 1 d . . . F12 F 0.1942(7) 0.6655(5) 0.6063(3) 0.168(3) Uani 1 1 d . . . F13 F 0.2098(3) 0.6210(3) 0.4925(2) 0.0827(10) Uani 1 1 d . . . F14 F 0.1377(4) 0.4982(3) 0.6146(3) 0.1092(14) Uani 1 1 d . . . B2 B -0.0849(5) 1.2561(5) 0.8753(3) 0.0496(11) Uani 1 1 d . . . F21 F 0.0053(3) 1.2882(3) 0.8102(2) 0.0933(12) Uani 1 1 d . . . F22 F -0.1457(5) 1.1899(5) 0.8556(4) 0.1413(19) Uani 1 1 d . . . F23 F -0.1709(3) 1.3555(3) 0.8911(2) 0.0928(12) Uani 1 1 d . . . F24 F -0.0403(3) 1.1852(4) 0.9411(2) 0.0963(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd 0.02226(12) 0.02203(12) 0.02947(13) -0.00983(9) -0.00506(9) -0.00206(8) P1 0.0248(4) 0.0220(4) 0.0274(4) -0.0090(3) -0.0027(3) -0.0052(3) P2 0.0252(4) 0.0207(3) 0.0209(3) -0.0072(3) -0.0053(3) -0.0032(3) C1 0.0398(18) 0.0269(15) 0.0214(14) -0.0058(12) -0.0038(13) -0.0069(13) C2 0.0353(17) 0.0344(17) 0.0219(14) -0.0097(12) -0.0031(12) -0.0105(13) C3 0.0305(16) 0.0314(16) 0.0283(15) -0.0132(13) -0.0027(12) -0.0091(13) C4 0.0262(14) 0.0201(13) 0.0304(15) -0.0093(11) -0.0035(12) -0.0052(11) C5 0.0295(16) 0.0225(14) 0.0346(16) -0.0065(12) -0.0043(13) -0.0051(12) C6 0.0339(18) 0.0229(15) 0.049(2) -0.0074(14) -0.0063(15) -0.0034(13) C7 0.0315(18) 0.0302(17) 0.056(2) -0.0207(16) -0.0006(16) -0.0020(14) C8 0.0342(17) 0.0332(17) 0.0386(18) -0.0202(14) 0.0032(14) -0.0085(14) C9 0.042(2) 0.0316(19) 0.059(2) -0.0012(17) -0.0143(19) 0.0048(16) C10 0.036(2) 0.042(2) 0.057(2) -0.0148(18) -0.0158(18) 0.0037(16) C11 0.0274(16) 0.0349(18) 0.046(2) -0.0153(15) -0.0118(14) -0.0009(13) C12 0.0322(16) 0.0317(16) 0.0302(16) -0.0104(13) -0.0096(13) -0.0049(13) C13 0.0246(14) 0.0236(14) 0.0268(14) -0.0099(11) -0.0052(11) -0.0059(11) C14 0.0331(16) 0.0252(15) 0.0269(15) -0.0089(12) -0.0036(12) -0.0097(12) C15 0.0359(18) 0.0366(18) 0.0335(17) -0.0126(14) 0.0032(14) -0.0151(14) C16 0.0241(16) 0.043(2) 0.048(2) -0.0195(16) 0.0009(14) -0.0068(14) C21 0.0282(16) 0.0380(18) 0.0347(17) -0.0157(14) -0.0034(13) -0.0089(13) C22 0.045(2) 0.055(2) 0.048(2) -0.0297(19) -0.0089(17) -0.0131(18) C23 0.052(3) 0.085(4) 0.061(3) -0.045(3) -0.003(2) -0.026(2) C24 0.043(2) 0.110(4) 0.041(2) -0.031(3) -0.0069(18) -0.027(3) C25 0.043(2) 0.082(3) 0.039(2) -0.010(2) -0.0147(18) -0.011(2) C26 0.0362(19) 0.049(2) 0.0387(19) -0.0101(16) -0.0092(15) -0.0109(16) C31 0.0292(16) 0.0244(15) 0.0388(17) -0.0063(13) -0.0027(13) -0.0079(12) C32 0.0376(19) 0.0333(18) 0.047(2) -0.0105(16) 0.0049(16) -0.0073(15) C33 0.052(3) 0.047(2) 0.053(3) -0.010(2) 0.016(2) -0.015(2) C34 0.057(3) 0.048(3) 0.062(3) 0.002(2) 0.009(2) -0.025(2) C35 0.053(2) 0.0315(19) 0.065(3) -0.0052(19) 0.002(2) -0.0147(18) C36 0.0387(19) 0.0303(18) 0.047(2) -0.0110(15) 0.0032(16) -0.0094(15) C41 0.0268(15) 0.0220(14) 0.0280(14) -0.0074(11) -0.0074(12) -0.0039(11) C42 0.0447(19) 0.0241(15) 0.0312(16) -0.0056(12) -0.0158(14) -0.0058(13) C43 0.055(2) 0.0235(16) 0.0362(18) -0.0050(13) -0.0143(16) -0.0062(15) C44 0.056(2) 0.0313(18) 0.0400(19) -0.0102(15) -0.0009(17) -0.0206(17) C45 0.042(2) 0.0319(17) 0.050(2) -0.0147(15) -0.0103(16) -0.0130(15) C46 0.0319(17) 0.0322(17) 0.0395(18) -0.0127(14) -0.0097(14) -0.0087(13) C51 0.0368(17) 0.0263(15) 0.0211(14) -0.0077(11) -0.0073(12) -0.0062(13) C52 0.055(2) 0.0284(16) 0.0256(15) -0.0085(13) -0.0065(15) -0.0098(15) C53 0.080(3) 0.034(2) 0.0309(18) -0.0036(15) -0.0120(19) -0.013(2) C54 0.076(3) 0.042(2) 0.0258(17) -0.0096(15) -0.0068(18) -0.016(2) C55 0.065(3) 0.0363(19) 0.0265(16) -0.0122(14) -0.0102(16) -0.0114(17) C56 0.052(2) 0.0305(17) 0.0280(16) -0.0108(13) -0.0071(15) -0.0054(15) N61 0.0286(14) 0.0342(15) 0.0443(16) -0.0204(13) -0.0084(12) 0.0008(12) C62 0.0389(19) 0.0379(19) 0.046(2) -0.0196(16) -0.0145(16) 0.0032(16) C63 0.061(3) 0.070(3) 0.082(3) -0.054(3) -0.028(3) 0.030(3) N71 0.0276(15) 0.0357(16) 0.0501(18) -0.0177(13) -0.0096(13) -0.0022(12) C72 0.0340(19) 0.040(2) 0.052(2) -0.0179(17) -0.0098(16) -0.0072(15) C73 0.039(2) 0.071(3) 0.084(3) -0.026(3) -0.028(2) -0.006(2) B1 0.085(4) 0.050(3) 0.056(3) -0.007(3) -0.010(3) -0.016(3) F11 0.098(3) 0.132(4) 0.093(3) -0.023(3) 0.013(2) 0.037(3) F12 0.297(8) 0.165(5) 0.097(3) 0.010(3) -0.083(4) -0.147(5) F13 0.086(2) 0.067(2) 0.069(2) -0.0159(16) 0.0044(17) 0.0011(17) F14 0.133(3) 0.059(2) 0.105(3) 0.000(2) 0.009(3) -0.032(2) B2 0.046(3) 0.055(3) 0.041(2) -0.010(2) -0.003(2) -0.008(2) F21 0.094(3) 0.084(2) 0.074(2) -0.0209(18) 0.0305(18) -0.024(2) F22 0.143(4) 0.138(4) 0.190(5) -0.051(4) -0.064(4) -0.064(4) F23 0.097(3) 0.081(2) 0.0630(19) -0.0132(17) 0.0039(18) 0.0136(19) F24 0.082(2) 0.123(3) 0.0602(19) -0.020(2) -0.0246(17) 0.022(2) _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 Pd N71 2.079(3) . ? Pd N61 2.086(3) . ? Pd P2 2.2757(8) . ? Pd P1 2.2848(8) . ? P1 C4 1.823(3) . ? P1 C31 1.826(3) . ? P1 C21 1.830(3) . ? P2 C13 1.820(3) . ? P2 C41 1.843(3) . ? P2 C51 1.854(3) . ? C1 C14 1.519(5) . ? C1 C2 1.571(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.517(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C8 1.399(5) . ? C3 C4 1.410(4) . ? C4 C5 1.398(4) . ? C5 C6 1.393(5) . ? C5 H5 0.9400 . ? C6 C7 1.393(5) . ? C6 C9 1.508(6) . ? C7 C8 1.379(5) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C9 C10 1.576(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.514(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C16 1.388(5) . ? C11 C12 1.391(5) . ? C12 C13 1.400(4) . ? C12 H12 0.9400 . ? C13 C14 1.417(4) . ? C14 C15 1.394(5) . ? C15 C16 1.380(5) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C21 C22 1.391(5) . ? C21 C26 1.399(5) . ? C22 C23 1.402(6) . ? C22 H22 0.9400 . ? C23 C24 1.375(8) . ? C23 H23 0.9400 . ? C24 C25 1.371(7) . ? C24 H24 0.9400 . ? C25 C26 1.386(5) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C32 1.387(5) . ? C31 C36 1.400(5) . ? C32 C33 1.392(5) . ? C32 H32 0.9400 . ? C33 C34 1.372(7) . ? C33 H33 0.9400 . ? C34 C35 1.374(7) . ? C34 H34 0.9400 . ? C35 C36 1.391(5) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C41 C46 1.528(4) . ? C41 C42 1.530(4) . ? C41 H41 0.9900 . ? C42 C43 1.523(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C43 C44 1.519(5) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C44 C45 1.518(5) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C45 C46 1.525(5) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C51 C56 1.527(4) . ? C51 C52 1.545(5) . ? C51 H51 0.9900 . ? C52 C53 1.536(5) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C53 C54 1.523(6) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C54 C55 1.512(5) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C55 C56 1.533(5) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? N61 C62 1.121(5) . ? C62 C63 1.455(5) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C63 H63C 0.9700 . ? N71 C72 1.119(5) . ? C72 C73 1.449(5) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C73 H73C 0.9700 . ? B1 F11 1.340(8) . ? B1 F12 1.358(8) . ? B1 F14 1.363(7) . ? B1 F13 1.365(7) . ? B2 F24 1.352(6) . ? B2 F21 1.354(6) . ? B2 F22 1.361(7) . ? B2 F23 1.369(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 N71 Pd N61 83.25(11) . . ? N71 Pd P2 172.84(8) . . ? N61 Pd P2 89.94(8) . . ? N71 Pd P1 88.41(9) . . ? N61 Pd P1 168.92(9) . . ? P2 Pd P1 98.62(3) . . ? C4 P1 C31 106.03(15) . . ? C4 P1 C21 105.00(15) . . ? C31 P1 C21 105.68(16) . . ? C4 P1 Pd 125.00(10) . . ? C31 P1 Pd 105.32(11) . . ? C21 P1 Pd 108.41(12) . . ? C13 P2 C41 106.87(14) . . ? C13 P2 C51 106.26(14) . . ? C41 P2 C51 106.25(14) . . ? C13 P2 Pd 121.34(10) . . ? C41 P2 Pd 106.37(10) . . ? C51 P2 Pd 108.86(11) . . ? C14 C1 C2 111.1(3) . . ? C14 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? C14 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C3 C2 C1 111.4(3) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C8 C3 C4 116.8(3) . . ? C8 C3 C2 117.4(3) . . ? C4 C3 C2 124.2(3) . . ? C5 C4 C3 118.6(3) . . ? C5 C4 P1 119.3(2) . . ? C3 C4 P1 121.9(2) . . ? C6 C5 C4 122.0(3) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 116.8(3) . . ? C5 C6 C9 120.7(4) . . ? C7 C6 C9 121.2(3) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 121.5(3) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C6 C9 C10 112.0(3) . . ? C6 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C6 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.1(3) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C16 C11 C12 117.0(3) . . ? C16 C11 C10 121.0(3) . . ? C12 C11 C10 120.7(3) . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 118.8(3) . . ? C12 C13 P2 119.3(2) . . ? C14 C13 P2 121.9(2) . . ? C15 C14 C13 117.1(3) . . ? C15 C14 C1 117.5(3) . . ? C13 C14 C1 123.9(3) . . ? C16 C15 C14 121.1(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C22 C21 C26 119.1(3) . . ? C22 C21 P1 119.6(3) . . ? C26 C21 P1 121.3(3) . . ? C21 C22 C23 119.8(4) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.9(4) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.8(5) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 120.0(4) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C32 C31 C36 118.9(3) . . ? C32 C31 P1 119.6(3) . . ? C36 C31 P1 121.4(3) . . ? C31 C32 C33 120.3(4) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 120.1(4) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 120.5(4) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 120.0(4) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 120.1(4) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? C46 C41 C42 110.5(3) . . ? C46 C41 P2 112.2(2) . . ? C42 C41 P2 115.7(2) . . ? C46 C41 H41 105.9 . . ? C42 C41 H41 105.9 . . ? P2 C41 H41 105.9 . . ? C43 C42 C41 109.9(3) . . ? C43 C42 H42A 109.7 . . ? C41 C42 H42A 109.7 . . ? C43 C42 H42B 109.7 . . ? C41 C42 H42B 109.7 . . ? H42A C42 H42B 108.2 . . ? C44 C43 C42 111.6(3) . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43B 109.3 . . ? C42 C43 H43B 109.3 . . ? H43A C43 H43B 108.0 . . ? C45 C44 C43 112.0(3) . . ? C45 C44 H44A 109.2 . . ? C43 C44 H44A 109.2 . . ? C45 C44 H44B 109.2 . . ? C43 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? C44 C45 C46 112.1(3) . . ? C44 C45 H45A 109.2 . . ? C46 C45 H45A 109.2 . . ? C44 C45 H45B 109.2 . . ? C46 C45 H45B 109.2 . . ? H45A C45 H45B 107.9 . . ? C45 C46 C41 110.3(3) . . ? C45 C46 H46A 109.6 . . ? C41 C46 H46A 109.6 . . ? C45 C46 H46B 109.6 . . ? C41 C46 H46B 109.6 . . ? H46A C46 H46B 108.1 . . ? C56 C51 C52 109.8(3) . . ? C56 C51 P2 114.2(2) . . ? C52 C51 P2 109.9(2) . . ? C56 C51 H51 107.6 . . ? C52 C51 H51 107.6 . . ? P2 C51 H51 107.6 . . ? C53 C52 C51 111.1(3) . . ? C53 C52 H52A 109.4 . . ? C51 C52 H52A 109.4 . . ? C53 C52 H52B 109.4 . . ? C51 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? C54 C53 C52 111.0(3) . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53B 109.4 . . ? C52 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C55 C54 C53 111.0(3) . . ? C55 C54 H54A 109.4 . . ? C53 C54 H54A 109.4 . . ? C55 C54 H54B 109.4 . . ? C53 C54 H54B 109.4 . . ? H54A C54 H54B 108.0 . . ? C54 C55 C56 111.3(3) . . ? C54 C55 H55A 109.4 . . ? C56 C55 H55A 109.4 . . ? C54 C55 H55B 109.4 . . ? C56 C55 H55B 109.4 . . ? H55A C55 H55B 108.0 . . ? C51 C56 C55 109.2(3) . . ? C51 C56 H56A 109.8 . . ? C55 C56 H56A 109.8 . . ? C51 C56 H56B 109.8 . . ? C55 C56 H56B 109.8 . . ? H56A C56 H56B 108.3 . . ? C62 N61 Pd 160.1(3) . . ? N61 C62 C63 179.8(5) . . ? C62 C63 H63A 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C62 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C72 N71 Pd 164.0(3) . . ? N71 C72 C73 178.4(5) . . ? C72 C73 H73A 109.5 . . ? C72 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C72 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? F11 B1 F12 108.1(6) . . ? F11 B1 F14 111.2(6) . . ? F12 B1 F14 107.8(5) . . ? F11 B1 F13 108.4(5) . . ? F12 B1 F13 108.5(6) . . ? F14 B1 F13 112.8(5) . . ? F24 B2 F21 112.4(4) . . ? F24 B2 F22 107.5(5) . . ? F21 B2 F22 107.1(5) . . ? F24 B2 F23 112.2(4) . . ? F21 B2 F23 111.7(4) . . ? F22 B2 F23 105.5(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 N71 Pd P1 C4 -163.88(16) . . . . ? N61 Pd P1 C4 155.0(5) . . . . ? P2 Pd P1 C4 14.75(13) . . . . ? N71 Pd P1 C31 73.34(15) . . . . ? N61 Pd P1 C31 32.2(5) . . . . ? P2 Pd P1 C31 -108.02(12) . . . . ? N71 Pd P1 C21 -39.40(15) . . . . ? N61 Pd P1 C21 -80.5(5) . . . . ? P2 Pd P1 C21 139.24(12) . . . . ? N71 Pd P2 C13 144.3(7) . . . . ? N61 Pd P2 C13 162.39(15) . . . . ? P1 Pd P2 C13 -24.66(12) . . . . ? N71 Pd P2 C41 22.1(8) . . . . ? N61 Pd P2 C41 40.18(14) . . . . ? P1 Pd P2 C41 -146.87(11) . . . . ? N71 Pd P2 C51 -92.0(8) . . . . ? N61 Pd P2 C51 -73.93(14) . . . . ? P1 Pd P2 C51 99.01(11) . . . . ? C14 C1 C2 C3 -30.4(4) . . . . ? C1 C2 C3 C8 108.5(3) . . . . ? C1 C2 C3 C4 -56.8(4) . . . . ? C8 C3 C4 C5 -18.1(4) . . . . ? C2 C3 C4 C5 147.4(3) . . . . ? C8 C3 C4 P1 166.9(2) . . . . ? C2 C3 C4 P1 -27.6(4) . . . . ? C31 P1 C4 C5 33.1(3) . . . . ? C21 P1 C4 C5 144.7(3) . . . . ? Pd P1 C4 C5 -89.3(3) . . . . ? C31 P1 C4 C3 -151.9(3) . . . . ? C21 P1 C4 C3 -40.3(3) . . . . ? Pd P1 C4 C3 85.7(3) . . . . ? C3 C4 C5 C6 3.4(5) . . . . ? P1 C4 C5 C6 178.5(3) . . . . ? C4 C5 C6 C7 13.8(5) . . . . ? C4 C5 C6 C9 -153.9(3) . . . . ? C5 C6 C7 C8 -16.0(5) . . . . ? C9 C6 C7 C8 151.6(4) . . . . ? C6 C7 C8 C3 1.2(5) . . . . ? C4 C3 C8 C7 16.1(5) . . . . ? C2 C3 C8 C7 -150.4(3) . . . . ? C5 C6 C9 C10 99.9(4) . . . . ? C7 C6 C9 C10 -67.3(5) . . . . ? C6 C9 C10 C11 -23.9(5) . . . . ? C9 C10 C11 C16 99.7(4) . . . . ? C9 C10 C11 C12 -66.7(5) . . . . ? C16 C11 C12 C13 -15.0(5) . . . . ? C10 C11 C12 C13 152.0(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C11 C12 C13 P2 -176.7(3) . . . . ? C41 P2 C13 C12 -118.9(3) . . . . ? C51 P2 C13 C12 -5.7(3) . . . . ? Pd P2 C13 C12 119.1(2) . . . . ? C41 P2 C13 C14 64.0(3) . . . . ? C51 P2 C13 C14 177.1(2) . . . . ? Pd P2 C13 C14 -58.0(3) . . . . ? C12 C13 C14 C15 15.0(4) . . . . ? P2 C13 C14 C15 -167.9(2) . . . . ? C12 C13 C14 C1 -150.9(3) . . . . ? P2 C13 C14 C1 26.2(4) . . . . ? C2 C1 C14 C15 -60.5(4) . . . . ? C2 C1 C14 C13 105.3(3) . . . . ? C13 C14 C15 C16 -16.2(5) . . . . ? C1 C14 C15 C16 150.7(3) . . . . ? C14 C15 C16 C11 1.5(5) . . . . ? C12 C11 C16 C15 14.1(5) . . . . ? C10 C11 C16 C15 -152.9(4) . . . . ? C4 P1 C21 C22 -70.3(3) . . . . ? C31 P1 C21 C22 41.5(3) . . . . ? Pd P1 C21 C22 154.0(3) . . . . ? C4 P1 C21 C26 110.0(3) . . . . ? C31 P1 C21 C26 -138.2(3) . . . . ? Pd P1 C21 C26 -25.7(3) . . . . ? C26 C21 C22 C23 0.8(6) . . . . ? P1 C21 C22 C23 -178.9(3) . . . . ? C21 C22 C23 C24 -0.5(7) . . . . ? C22 C23 C24 C25 0.0(7) . . . . ? C23 C24 C25 C26 0.1(7) . . . . ? C24 C25 C26 C21 0.3(6) . . . . ? C22 C21 C26 C25 -0.7(6) . . . . ? P1 C21 C26 C25 178.9(3) . . . . ? C4 P1 C31 C32 -149.7(3) . . . . ? C21 P1 C31 C32 99.2(3) . . . . ? Pd P1 C31 C32 -15.5(3) . . . . ? C4 P1 C31 C36 33.9(3) . . . . ? C21 P1 C31 C36 -77.2(3) . . . . ? Pd P1 C31 C36 168.1(3) . . . . ? C36 C31 C32 C33 -1.1(6) . . . . ? P1 C31 C32 C33 -177.6(4) . . . . ? C31 C32 C33 C34 0.7(8) . . . . ? C32 C33 C34 C35 0.0(8) . . . . ? C33 C34 C35 C36 -0.2(8) . . . . ? C34 C35 C36 C31 -0.2(7) . . . . ? C32 C31 C36 C35 0.9(6) . . . . ? P1 C31 C36 C35 177.3(3) . . . . ? C13 P2 C41 C46 46.7(3) . . . . ? C51 P2 C41 C46 -66.4(3) . . . . ? Pd P2 C41 C46 177.7(2) . . . . ? C13 P2 C41 C42 -81.3(3) . . . . ? C51 P2 C41 C42 165.5(2) . . . . ? Pd P2 C41 C42 49.7(3) . . . . ? C46 C41 C42 C43 58.8(4) . . . . ? P2 C41 C42 C43 -172.3(2) . . . . ? C41 C42 C43 C44 -56.6(4) . . . . ? C42 C43 C44 C45 53.8(4) . . . . ? C43 C44 C45 C46 -52.8(4) . . . . ? C44 C45 C46 C41 54.7(4) . . . . ? C42 C41 C46 C45 -57.8(4) . . . . ? P2 C41 C46 C45 171.5(2) . . . . ? C13 P2 C51 C56 -152.2(2) . . . . ? C41 P2 C51 C56 -38.7(3) . . . . ? Pd P2 C51 C56 75.5(3) . . . . ? C13 P2 C51 C52 83.9(3) . . . . ? C41 P2 C51 C52 -162.6(2) . . . . ? Pd P2 C51 C52 -48.4(3) . . . . ? C56 C51 C52 C53 57.1(4) . . . . ? P2 C51 C52 C53 -176.5(3) . . . . ? C51 C52 C53 C54 -54.7(5) . . . . ? C52 C53 C54 C55 54.8(5) . . . . ? C53 C54 C55 C56 -57.8(5) . . . . ? C52 C51 C56 C55 -58.7(4) . . . . ? P2 C51 C56 C55 177.3(3) . . . . ? C54 C55 C56 C51 59.8(4) . . . . ? N71 Pd N61 C62 -10.1(9) . . . . ? P2 Pd N61 C62 172.1(9) . . . . ? P1 Pd N61 C62 31.4(13) . . . . ? Pd N61 C62 C63 151(100) . . . . ? N61 Pd N71 C72 -50.6(12) . . . . ? P2 Pd N71 C72 -32.4(17) . . . . ? P1 Pd N71 C72 136.7(12) . . . . ? Pd N71 C72 C73 -72(16) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.684 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.089 # Attachment '- fro5550.cif' data_fro5550 _database_code_depnum_ccdc_archive 'CCDC 816639' #TrackingRef '- fro5550.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H41.50 B2 F8 N2.50 P2 Pd' _chemical_formula_weight 959.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1729(1) _cell_length_b 16.7826(2) _cell_length_c 21.2782(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.027(1) _cell_angle_gamma 90.00 _cell_volume 4280.59(9) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 9138 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1948 _exptl_absorpt_coefficient_mu 0.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8454 _exptl_absorpt_correction_T_max 0.9182 _exptl_absorpt_process_details 'DEnzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27747 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 27.90 _reflns_number_total 9924 _reflns_number_gt 8360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+7.7435P] 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 9924 _refine_ls_number_parameters 654 _refine_ls_number_restraints 537 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.098 _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 Pd Pd 0.53459(2) 0.769425(15) 0.811233(11) 0.03199(8) Uani 1 1 d . . . P1 P 0.64766(7) 0.70981(5) 0.75045(4) 0.02869(16) Uani 1 1 d . . . P2 P 0.45285(7) 0.86213(5) 0.74046(4) 0.02997(17) Uani 1 1 d . . . C1 C 0.4162(3) 0.7450(2) 0.62012(19) 0.0445(8) Uani 1 1 d . . . H1A H 0.3434 0.7351 0.5935 0.053 Uiso 1 1 calc R . . H1B H 0.4092 0.7360 0.6647 0.053 Uiso 1 1 calc R . . C2 C 0.5042(3) 0.6866(2) 0.60098(17) 0.0421(8) Uani 1 1 d . . . H2A H 0.5026 0.6366 0.6245 0.050 Uiso 1 1 calc R . . H2B H 0.4848 0.6747 0.5553 0.050 Uiso 1 1 calc R . . C3 C 0.6203(3) 0.7212(2) 0.61497(16) 0.0371(7) Uani 1 1 d . . . C4 C 0.6749(3) 0.74836(19) 0.67494(15) 0.0305(6) Uani 1 1 d . . . C5 C 0.7505(3) 0.8115(2) 0.67793(16) 0.0360(7) Uani 1 1 d . . . H5 H 0.7844 0.8310 0.7180 0.043 Uiso 1 1 calc R . . C6 C 0.7768(3) 0.8462(2) 0.62301(18) 0.0427(8) Uani 1 1 d . . . C7 C 0.7464(3) 0.8047(3) 0.56677(18) 0.0476(9) Uani 1 1 d . . . H7 H 0.7782 0.8180 0.5310 0.057 Uiso 1 1 calc R . . C8 C 0.6695(3) 0.7436(2) 0.56278(17) 0.0447(8) Uani 1 1 d . . . H8 H 0.6496 0.7162 0.5239 0.054 Uiso 1 1 calc R . . C9 C 0.8149(3) 0.9326(3) 0.6237(2) 0.0574(11) Uani 1 1 d . . . H9A H 0.8733 0.9378 0.5975 0.069 Uiso 1 1 calc R . . H9B H 0.8470 0.9479 0.6675 0.069 Uiso 1 1 calc R . . C10 C 0.7158(4) 0.9907(3) 0.5974(2) 0.0531(10) Uani 1 1 d . . . H10A H 0.7237 1.0398 0.6226 0.064 Uiso 1 1 calc R . . H10B H 0.7196 1.0047 0.5531 0.064 Uiso 1 1 calc R . . C11 C 0.6039(3) 0.9535(2) 0.60010(18) 0.0431(8) Uani 1 1 d . . . C12 C 0.5693(3) 0.94025(19) 0.65826(17) 0.0365(7) Uani 1 1 d . . . H12 H 0.5976 0.9720 0.6938 0.044 Uiso 1 1 calc R . . C13 C 0.4928(3) 0.88014(19) 0.66379(15) 0.0323(6) Uani 1 1 d . . . C14 C 0.4512(3) 0.8311(2) 0.61163(16) 0.0375(7) Uani 1 1 d . . . C15 C 0.4668(3) 0.8578(3) 0.55186(17) 0.0457(9) Uani 1 1 d . . . H15 H 0.4253 0.8351 0.5148 0.055 Uiso 1 1 calc R . . C16 C 0.5424(3) 0.9172(3) 0.54650(17) 0.0499(10) Uani 1 1 d . . . H16 H 0.5527 0.9337 0.5057 0.060 Uiso 1 1 calc R . . C21 C 0.6009(3) 0.60794(19) 0.73426(15) 0.0325(6) Uani 1 1 d . . . C22 C 0.6558(3) 0.5578(2) 0.69672(17) 0.0385(7) Uani 1 1 d . . . H22 H 0.7206 0.5756 0.6827 0.046 Uiso 1 1 calc R . . C23 C 0.6148(3) 0.4825(2) 0.68032(18) 0.0451(8) Uani 1 1 d . . . H23 H 0.6530 0.4488 0.6562 0.054 Uiso 1 1 calc R . . C24 C 0.5181(4) 0.4566(2) 0.6993(2) 0.0522(10) Uani 1 1 d . . . H24 H 0.4894 0.4058 0.6872 0.063 Uiso 1 1 calc R . . C25 C 0.4635(3) 0.5054(2) 0.7360(2) 0.0520(10) Uani 1 1 d . . . H25 H 0.3980 0.4874 0.7492 0.062 Uiso 1 1 calc R . . C26 C 0.5045(3) 0.5807(2) 0.75360(17) 0.0408(8) Uani 1 1 d . . . H26 H 0.4668 0.6135 0.7787 0.049 Uiso 1 1 calc R . . C31 C 0.7852(3) 0.70831(19) 0.80106(15) 0.0314(6) Uani 1 1 d . . . C32 C 0.8664(3) 0.6534(2) 0.79162(18) 0.0419(8) Uani 1 1 d . . . H32 H 0.8517 0.6168 0.7577 0.050 Uiso 1 1 calc R . . C33 C 0.9686(3) 0.6523(2) 0.8319(2) 0.0467(9) Uani 1 1 d . . . H33 H 1.0222 0.6141 0.8259 0.056 Uiso 1 1 calc R . . C34 C 0.9925(3) 0.7067(3) 0.88065(19) 0.0489(9) Uani 1 1 d . . . H34 H 1.0624 0.7060 0.9076 0.059 Uiso 1 1 calc R . . C35 C 0.9138(3) 0.7621(3) 0.88980(19) 0.0502(9) Uani 1 1 d . . . H35 H 0.9302 0.7999 0.9227 0.060 Uiso 1 1 calc R . . C36 C 0.8097(3) 0.7625(2) 0.85048(17) 0.0411(8) Uani 1 1 d . . . H36 H 0.7557 0.7998 0.8576 0.049 Uiso 1 1 calc R . . C41 C 0.3043(3) 0.8405(2) 0.72258(17) 0.0391(7) Uani 1 1 d . . . C42 C 0.2569(3) 0.7835(2) 0.7571(2) 0.0499(9) Uani 1 1 d . . . H42 H 0.3015 0.7546 0.7899 0.060 Uiso 1 1 calc R . . C43 C 0.1430(4) 0.7697(3) 0.7425(3) 0.0673(14) Uani 1 1 d . . . H43 H 0.1104 0.7315 0.7658 0.081 Uiso 1 1 calc R . . C44 C 0.0774(4) 0.8110(4) 0.6947(3) 0.0725(15) Uani 1 1 d . . . H44 H 0.0004 0.8008 0.6852 0.087 Uiso 1 1 calc R . . C45 C 0.1238(3) 0.8675(3) 0.6603(2) 0.0613(13) Uani 1 1 d . . . H45 H 0.0784 0.8958 0.6275 0.074 Uiso 1 1 calc R . . C46 C 0.2374(3) 0.8828(3) 0.67400(18) 0.0468(9) Uani 1 1 d . . . H46 H 0.2691 0.9215 0.6507 0.056 Uiso 1 1 calc R . . C51 C 0.4686(3) 0.95615(19) 0.78307(15) 0.0335(7) Uani 1 1 d . . . C52 C 0.5661(3) 0.9715(2) 0.82632(17) 0.0420(8) Uani 1 1 d . . . H52 H 0.6256 0.9351 0.8306 0.050 Uiso 1 1 calc R . . C53 C 0.5757(4) 1.0403(2) 0.86318(19) 0.0525(10) Uani 1 1 d . . . H53 H 0.6421 1.0508 0.8918 0.063 Uiso 1 1 calc R . . C54 C 0.4880(5) 1.0928(3) 0.8577(2) 0.0678(13) Uani 1 1 d . . . H54 H 0.4940 1.1389 0.8831 0.081 Uiso 1 1 calc R . . C55 C 0.3924(5) 1.0784(3) 0.8154(3) 0.0714(14) Uani 1 1 d . . . H55 H 0.3327 1.1146 0.8121 0.086 Uiso 1 1 calc R . . C56 C 0.3821(4) 1.0112(2) 0.7773(2) 0.0549(10) Uani 1 1 d . . . H56 H 0.3165 1.0027 0.7475 0.066 Uiso 1 1 calc R . . N61 N 0.5906(3) 0.68818(19) 0.88387(14) 0.0432(7) Uani 1 1 d . . . C62 C 0.6060(3) 0.6589(2) 0.93233(18) 0.0435(8) Uani 1 1 d . . . C63 C 0.6256(5) 0.6240(3) 0.9953(2) 0.0683(13) Uani 1 1 d . . . H63A H 0.7046 0.6263 1.0128 0.103 Uiso 1 1 calc R . . H63B H 0.6012 0.5689 0.9927 0.103 Uiso 1 1 calc R . . H63C H 0.5842 0.6534 1.0228 0.103 Uiso 1 1 calc R . . N71 N 0.4458(3) 0.82102(19) 0.87544(14) 0.0433(7) Uani 1 1 d . . . C72 C 0.4065(4) 0.8515(3) 0.9131(2) 0.0549(10) Uani 1 1 d . . . C73 C 0.3560(5) 0.8938(5) 0.9605(3) 0.107(2) Uani 1 1 d . . . H73A H 0.4077 0.9337 0.9812 0.160 Uiso 1 1 calc R . . H73B H 0.3387 0.8564 0.9921 0.160 Uiso 1 1 calc R . . H73C H 0.2880 0.9196 0.9398 0.160 Uiso 1 1 calc R . . B1A B 0.2185(11) 0.6162(7) 0.4955(5) 0.056(3) Uani 0.58(2) 1 d PDU A 1 F11A F 0.2820(12) 0.5856(8) 0.5484(5) 0.091(4) Uani 0.58(2) 1 d PDU A 1 F12A F 0.1101(9) 0.5953(10) 0.4929(7) 0.128(5) Uani 0.58(2) 1 d PDU A 1 F13A F 0.2546(7) 0.5871(6) 0.4429(3) 0.085(3) Uani 0.58(2) 1 d PDU A 1 F14A F 0.2276(12) 0.6972(4) 0.4948(4) 0.100(3) Uani 0.58(2) 1 d PDU A 1 B1B B 0.2024(13) 0.6163(8) 0.5058(8) 0.061(6) Uani 0.42(2) 1 d PDU A 2 F11B F 0.2711(14) 0.5915(10) 0.5589(8) 0.073(4) Uani 0.42(2) 1 d PDU A 2 F12B F 0.1143(11) 0.5657(8) 0.4917(7) 0.074(3) Uani 0.42(2) 1 d PDU A 2 F13B F 0.2577(14) 0.6178(14) 0.4557(10) 0.160(7) Uani 0.42(2) 1 d PDU A 2 F14B F 0.1615(17) 0.6894(7) 0.5149(9) 0.129(6) Uani 0.42(2) 1 d PDU A 2 B2A B 1.3134(11) 0.5900(7) 0.9019(5) 0.054(4) Uani 0.533(16) 1 d PDU B 1 F21A F 1.2268(10) 0.5551(8) 0.9238(7) 0.109(4) Uani 0.533(16) 1 d PDU B 1 F22A F 1.2879(10) 0.6063(8) 0.8385(4) 0.105(4) Uani 0.533(16) 1 d PDU B 1 F23A F 1.3438(11) 0.6586(6) 0.9344(5) 0.105(4) Uani 0.533(16) 1 d PDU B 1 F24A F 1.4008(6) 0.5389(5) 0.9108(6) 0.105(3) Uani 0.533(16) 1 d PDU B 1 B2B B 1.2955(11) 0.5981(8) 0.9029(6) 0.056(5) Uani 0.467(16) 1 d PDU B 2 F21B F 1.1990(8) 0.5582(8) 0.9044(7) 0.090(4) Uani 0.467(16) 1 d PDU B 2 F22B F 1.3246(12) 0.5883(9) 0.8449(6) 0.109(5) Uani 0.467(16) 1 d PDU B 2 F23B F 1.2787(11) 0.6765(5) 0.9138(5) 0.092(3) Uani 0.467(16) 1 d PDU B 2 F24B F 1.3774(8) 0.5711(8) 0.9495(7) 0.126(5) Uani 0.467(16) 1 d PDU B 2 N81 N 0.5875(8) 0.5899(6) 0.4577(5) 0.089(3) Uani 0.50 1 d PDU C -1 C82 C 0.5450(14) 0.5404(10) 0.4793(8) 0.076(4) Uani 0.50 1 d PDU C -1 C83 C 0.4818(17) 0.4796(11) 0.5066(9) 0.082(5) Uani 0.50 1 d PDU C -1 H83A H 0.4591 0.5003 0.5450 0.123 Uiso 0.50 1 calc PR C -1 H83B H 0.5281 0.4328 0.5172 0.123 Uiso 0.50 1 calc PR C -1 H83C H 0.4162 0.4654 0.4759 0.123 Uiso 0.50 1 calc PR C -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd 0.03703(14) 0.03082(13) 0.03055(13) 0.00093(9) 0.01264(9) 0.00405(10) P1 0.0302(4) 0.0264(4) 0.0307(4) -0.0002(3) 0.0087(3) 0.0023(3) P2 0.0285(4) 0.0289(4) 0.0342(4) -0.0004(3) 0.0102(3) 0.0016(3) C1 0.0383(18) 0.047(2) 0.049(2) -0.0131(17) 0.0090(15) -0.0056(15) C2 0.047(2) 0.0391(19) 0.0390(18) -0.0077(15) 0.0042(15) 0.0006(15) C3 0.0408(18) 0.0369(17) 0.0339(16) -0.0018(14) 0.0072(13) 0.0077(14) C4 0.0291(15) 0.0330(16) 0.0304(15) 0.0016(12) 0.0081(12) 0.0048(12) C5 0.0274(15) 0.0431(18) 0.0372(17) 0.0066(14) 0.0049(12) 0.0022(13) C6 0.0305(16) 0.053(2) 0.046(2) 0.0159(17) 0.0109(14) 0.0019(15) C7 0.047(2) 0.062(2) 0.0384(18) 0.0134(18) 0.0202(15) 0.0153(18) C8 0.054(2) 0.048(2) 0.0340(18) -0.0021(15) 0.0130(15) 0.0126(17) C9 0.049(2) 0.067(3) 0.057(2) 0.021(2) 0.0095(18) -0.018(2) C10 0.061(2) 0.045(2) 0.060(2) 0.0062(19) 0.030(2) -0.0044(19) C11 0.051(2) 0.0356(18) 0.046(2) 0.0096(15) 0.0177(16) 0.0102(15) C12 0.0420(18) 0.0276(15) 0.0416(18) 0.0013(13) 0.0123(14) 0.0040(13) C13 0.0295(15) 0.0314(15) 0.0371(16) 0.0019(13) 0.0092(12) 0.0070(12) C14 0.0276(15) 0.0449(19) 0.0398(17) -0.0047(15) 0.0053(13) 0.0073(14) C15 0.0428(19) 0.058(2) 0.0343(17) -0.0041(17) 0.0023(14) 0.0144(17) C16 0.065(2) 0.054(2) 0.0344(18) 0.0138(17) 0.0171(17) 0.024(2) C21 0.0342(16) 0.0272(15) 0.0358(16) 0.0008(13) 0.0051(12) 0.0006(12) C22 0.0402(18) 0.0340(17) 0.0426(18) -0.0038(14) 0.0109(14) 0.0011(14) C23 0.055(2) 0.0302(17) 0.050(2) -0.0056(15) 0.0073(17) 0.0035(15) C24 0.063(3) 0.0331(18) 0.061(2) -0.0032(18) 0.0115(19) -0.0107(18) C25 0.052(2) 0.045(2) 0.061(2) 0.0025(19) 0.0149(18) -0.0161(18) C26 0.0413(18) 0.0382(18) 0.0452(19) 0.0022(15) 0.0137(15) 0.0001(15) C31 0.0324(15) 0.0320(15) 0.0306(15) 0.0030(12) 0.0077(12) -0.0008(12) C32 0.0353(17) 0.0423(19) 0.049(2) -0.0056(16) 0.0091(14) 0.0041(15) C33 0.0335(17) 0.045(2) 0.061(2) 0.0055(18) 0.0078(16) 0.0079(15) C34 0.0397(19) 0.059(2) 0.046(2) 0.0097(19) 0.0010(15) -0.0048(17) C35 0.050(2) 0.055(2) 0.043(2) -0.0103(18) -0.0008(16) 0.0012(18) C36 0.0434(19) 0.0406(18) 0.0387(18) -0.0066(15) 0.0051(14) 0.0051(15) C41 0.0303(16) 0.0424(18) 0.0471(19) -0.0101(15) 0.0141(14) 0.0030(14) C42 0.043(2) 0.049(2) 0.062(2) -0.0079(19) 0.0192(17) -0.0087(17) C43 0.046(2) 0.070(3) 0.094(4) -0.021(3) 0.034(2) -0.023(2) C44 0.034(2) 0.096(4) 0.089(4) -0.038(3) 0.015(2) -0.008(2) C45 0.0344(19) 0.092(4) 0.057(2) -0.025(2) 0.0070(17) 0.012(2) C46 0.0346(17) 0.060(2) 0.047(2) -0.0106(18) 0.0092(15) 0.0080(16) C51 0.0397(17) 0.0275(15) 0.0358(16) 0.0011(13) 0.0130(13) 0.0016(13) C52 0.0448(19) 0.0392(19) 0.0435(19) -0.0050(15) 0.0124(15) -0.0016(15) C53 0.072(3) 0.045(2) 0.042(2) -0.0103(17) 0.0147(18) -0.015(2) C54 0.102(4) 0.043(2) 0.061(3) -0.018(2) 0.021(3) -0.002(2) C55 0.082(3) 0.046(2) 0.088(4) -0.015(2) 0.018(3) 0.023(2) C56 0.055(2) 0.041(2) 0.067(3) -0.0065(19) 0.007(2) 0.0112(18) N61 0.0501(17) 0.0443(17) 0.0378(16) 0.0039(14) 0.0145(13) 0.0044(14) C62 0.053(2) 0.0395(19) 0.0397(19) 0.0020(16) 0.0127(15) 0.0028(16) C63 0.093(4) 0.069(3) 0.043(2) 0.018(2) 0.013(2) 0.010(3) N71 0.0528(18) 0.0414(16) 0.0412(16) 0.0025(13) 0.0233(14) 0.0031(14) C72 0.054(2) 0.066(3) 0.048(2) -0.005(2) 0.0218(18) -0.001(2) C73 0.087(4) 0.156(7) 0.090(4) -0.053(4) 0.051(3) 0.006(4) B1A 0.051(6) 0.075(7) 0.045(5) 0.014(4) 0.012(5) 0.004(5) F11A 0.093(6) 0.092(6) 0.078(6) -0.005(5) -0.015(5) 0.015(5) F12A 0.081(5) 0.168(9) 0.132(7) 0.021(7) 0.007(5) -0.024(6) F13A 0.100(5) 0.097(5) 0.060(3) -0.015(3) 0.022(3) -0.014(3) F14A 0.152(8) 0.066(4) 0.073(4) 0.007(3) -0.003(4) 0.018(4) B1B 0.048(8) 0.072(9) 0.061(9) 0.002(6) 0.001(6) -0.020(6) F11B 0.074(7) 0.083(7) 0.058(5) 0.013(5) -0.002(5) -0.015(5) F12B 0.068(6) 0.074(6) 0.079(6) -0.006(4) 0.004(4) -0.029(4) F13B 0.183(10) 0.164(11) 0.149(10) 0.047(8) 0.076(8) -0.014(8) F14B 0.147(9) 0.090(7) 0.137(8) -0.006(6) -0.010(7) 0.031(6) B2A 0.057(6) 0.057(7) 0.051(7) -0.005(5) 0.020(5) -0.007(5) F21A 0.097(7) 0.128(7) 0.115(7) 0.001(5) 0.057(6) -0.045(5) F22A 0.116(7) 0.124(7) 0.070(5) 0.013(4) 0.005(4) 0.012(5) F23A 0.118(7) 0.099(6) 0.112(6) -0.045(5) 0.054(5) -0.038(5) F24A 0.084(4) 0.084(5) 0.142(7) 0.005(5) 0.006(4) 0.007(4) B2B 0.052(7) 0.063(8) 0.053(8) 0.002(6) 0.015(5) 0.001(6) F21B 0.060(4) 0.102(6) 0.108(7) -0.009(5) 0.018(4) -0.013(4) F22B 0.111(7) 0.145(8) 0.089(7) -0.026(6) 0.069(6) -0.011(6) F23B 0.113(7) 0.070(5) 0.099(6) 0.007(4) 0.036(5) -0.002(4) F24B 0.094(6) 0.144(8) 0.127(8) 0.038(6) -0.017(5) 0.020(5) N81 0.080(5) 0.083(6) 0.097(6) -0.025(5) -0.004(5) 0.020(5) C82 0.083(8) 0.069(7) 0.074(8) -0.018(6) 0.008(6) 0.011(6) C83 0.091(9) 0.082(10) 0.074(8) -0.020(7) 0.015(6) 0.009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd N71 2.074(3) . ? Pd N61 2.085(3) . ? Pd P2 2.2709(8) . ? Pd P1 2.2777(8) . ? P1 C4 1.816(3) . ? P1 C21 1.816(3) . ? P1 C31 1.826(3) . ? P2 C13 1.807(3) . ? P2 C51 1.813(3) . ? P2 C41 1.818(3) . ? C1 C14 1.525(5) . ? C1 C2 1.557(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.509(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C8 1.401(5) . ? C3 C4 1.408(5) . ? C4 C5 1.397(5) . ? C5 C6 1.393(5) . ? C5 H5 0.9400 . ? C6 C7 1.379(6) . ? C6 C9 1.521(6) . ? C7 C8 1.382(6) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C9 C10 1.575(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.509(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C16 1.391(6) . ? C11 C12 1.393(5) . ? C12 C13 1.391(5) . ? C12 H12 0.9400 . ? C13 C14 1.404(5) . ? C14 C15 1.393(5) . ? C15 C16 1.374(6) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C21 C26 1.387(5) . ? C21 C22 1.406(4) . ? C22 C23 1.380(5) . ? C22 H22 0.9400 . ? C23 C24 1.380(6) . ? C23 H23 0.9400 . ? C24 C25 1.380(6) . ? C24 H24 0.9400 . ? C25 C26 1.387(5) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C36 1.383(5) . ? C31 C32 1.392(5) . ? C32 C33 1.383(5) . ? C32 H32 0.9400 . ? C33 C34 1.374(6) . ? C33 H33 0.9400 . ? C34 C35 1.374(6) . ? C34 H34 0.9400 . ? C35 C36 1.391(5) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C41 C42 1.391(5) . ? C41 C46 1.395(5) . ? C42 C43 1.387(6) . ? C42 H42 0.9400 . ? C43 C44 1.368(8) . ? C43 H43 0.9400 . ? C44 C45 1.377(8) . ? C44 H44 0.9400 . ? C45 C46 1.386(5) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? C51 C56 1.391(5) . ? C51 C52 1.393(5) . ? C52 C53 1.389(5) . ? C52 H52 0.9400 . ? C53 C54 1.374(7) . ? C53 H53 0.9400 . ? C54 C55 1.364(7) . ? C54 H54 0.9400 . ? C55 C56 1.381(6) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? N61 C62 1.128(4) . ? C62 C63 1.444(5) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C63 H63C 0.9700 . ? N71 C72 1.125(5) . ? C72 C73 1.455(6) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C73 H73C 0.9700 . ? B1A F11A 1.351(10) . ? B1A F12A 1.358(11) . ? B1A F13A 1.364(11) . ? B1A F14A 1.364(10) . ? B1B F11B 1.349(12) . ? B1B F14B 1.350(12) . ? B1B F13B 1.358(12) . ? B1B F12B 1.360(11) . ? B2A F24A 1.354(12) . ? B2A F21A 1.358(11) . ? B2A F22A 1.359(11) . ? B2A F23A 1.361(10) . ? B2B F22B 1.351(11) . ? B2B F24B 1.356(12) . ? B2B F23B 1.358(12) . ? B2B F21B 1.359(11) . ? N81 C82 1.120(14) . ? C82 C83 1.458(14) . ? C83 H83A 0.9700 . ? C83 H83B 0.9700 . ? C83 H83C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N71 Pd N61 85.73(12) . . ? N71 Pd P2 86.12(9) . . ? N61 Pd P2 171.41(8) . . ? N71 Pd P1 173.47(9) . . ? N61 Pd P1 88.95(8) . . ? P2 Pd P1 99.36(3) . . ? C4 P1 C21 105.49(15) . . ? C4 P1 C31 103.69(14) . . ? C21 P1 C31 108.88(15) . . ? C4 P1 Pd 124.59(10) . . ? C21 P1 Pd 108.73(11) . . ? C31 P1 Pd 104.70(10) . . ? C13 P2 C51 106.50(15) . . ? C13 P2 C41 105.01(16) . . ? C51 P2 C41 107.07(15) . . ? C13 P2 Pd 123.88(10) . . ? C51 P2 Pd 105.58(11) . . ? C41 P2 Pd 107.86(13) . . ? C14 C1 C2 110.2(3) . . ? C14 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? C14 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C1 111.7(3) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C8 C3 C4 115.6(3) . . ? C8 C3 C2 117.5(3) . . ? C4 C3 C2 125.6(3) . . ? C5 C4 C3 119.3(3) . . ? C5 C4 P1 116.8(2) . . ? C3 C4 P1 123.8(3) . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 116.8(4) . . ? C7 C6 C9 121.7(3) . . ? C5 C6 C9 120.4(4) . . ? C6 C7 C8 120.4(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 121.9(3) . . ? C7 C8 H8 119.0 . . ? C3 C8 H8 119.0 . . ? C6 C9 C10 111.9(3) . . ? C6 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C6 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.8(3) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C16 C11 C12 117.1(4) . . ? C16 C11 C10 120.7(3) . . ? C12 C11 C10 121.0(4) . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.9(3) . . ? C12 C13 P2 119.1(3) . . ? C14 C13 P2 119.9(3) . . ? C15 C14 C13 116.4(3) . . ? C15 C14 C1 119.9(3) . . ? C13 C14 C1 122.1(3) . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 121.4(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C26 C21 C22 118.8(3) . . ? C26 C21 P1 120.5(3) . . ? C22 C21 P1 120.5(2) . . ? C23 C22 C21 120.4(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.2(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.9(4) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.5(4) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C36 C31 C32 118.7(3) . . ? C36 C31 P1 119.6(3) . . ? C32 C31 P1 121.7(3) . . ? C33 C32 C31 120.3(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 120.6(3) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 119.7(4) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 120.1(4) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C31 C36 C35 120.6(3) . . ? C31 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C42 C41 C46 119.9(3) . . ? C42 C41 P2 121.1(3) . . ? C46 C41 P2 119.0(3) . . ? C43 C42 C41 119.1(4) . . ? C43 C42 H42 120.4 . . ? C41 C42 H42 120.4 . . ? C44 C43 C42 120.9(5) . . ? C44 C43 H43 119.5 . . ? C42 C43 H43 119.5 . . ? C43 C44 C45 120.2(4) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 120.2(5) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C41 119.6(4) . . ? C45 C46 H46 120.2 . . ? C41 C46 H46 120.2 . . ? C56 C51 C52 118.7(3) . . ? C56 C51 P2 121.4(3) . . ? C52 C51 P2 119.7(3) . . ? C53 C52 C51 120.3(4) . . ? C53 C52 H52 119.8 . . ? C51 C52 H52 119.8 . . ? C54 C53 C52 119.8(4) . . ? C54 C53 H53 120.1 . . ? C52 C53 H53 120.1 . . ? C55 C54 C53 120.3(4) . . ? C55 C54 H54 119.9 . . ? C53 C54 H54 119.9 . . ? C54 C55 C56 120.8(4) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C55 C56 C51 120.0(4) . . ? C55 C56 H56 120.0 . . ? C51 C56 H56 120.0 . . ? C62 N61 Pd 160.6(3) . . ? N61 C62 C63 178.1(4) . . ? C62 C63 H63A 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C62 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C72 N71 Pd 173.8(4) . . ? N71 C72 C73 177.8(6) . . ? C72 C73 H73A 109.5 . . ? C72 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C72 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? F11A B1A F12A 110.3(10) . . ? F11A B1A F13A 109.2(9) . . ? F12A B1A F13A 108.9(9) . . ? F11A B1A F14A 110.6(9) . . ? F12A B1A F14A 109.8(9) . . ? F13A B1A F14A 108.0(9) . . ? F11B B1B F14B 110.5(11) . . ? F11B B1B F13B 110.1(11) . . ? F14B B1B F13B 110.0(11) . . ? F11B B1B F12B 110.0(11) . . ? F14B B1B F12B 107.6(11) . . ? F13B B1B F12B 108.6(11) . . ? F24A B2A F21A 108.5(9) . . ? F24A B2A F22A 107.7(9) . . ? F21A B2A F22A 111.8(10) . . ? F24A B2A F23A 109.1(9) . . ? F21A B2A F23A 110.4(10) . . ? F22A B2A F23A 109.3(9) . . ? F22B B2B F24B 110.5(11) . . ? F22B B2B F23B 110.3(10) . . ? F24B B2B F23B 108.2(10) . . ? F22B B2B F21B 109.1(10) . . ? F24B B2B F21B 110.3(10) . . ? F23B B2B F21B 108.5(10) . . ? N81 C82 C83 175.5(14) . . ? 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 N71 Pd P1 C4 -135.6(8) . . . . ? N61 Pd P1 C4 -171.00(16) . . . . ? P2 Pd P1 C4 11.17(14) . . . . ? N71 Pd P1 C21 99.2(8) . . . . ? N61 Pd P1 C21 63.81(14) . . . . ? P2 Pd P1 C21 -114.02(11) . . . . ? N71 Pd P1 C31 -17.1(8) . . . . ? N61 Pd P1 C31 -52.44(14) . . . . ? P2 Pd P1 C31 129.73(11) . . . . ? N71 Pd P2 C13 170.07(16) . . . . ? N61 Pd P2 C13 -171.7(6) . . . . ? P1 Pd P2 C13 -6.35(14) . . . . ? N71 Pd P2 C51 47.22(14) . . . . ? N61 Pd P2 C51 65.5(6) . . . . ? P1 Pd P2 C51 -129.19(11) . . . . ? N71 Pd P2 C41 -66.97(15) . . . . ? N61 Pd P2 C41 -48.7(6) . . . . ? P1 Pd P2 C41 116.61(12) . . . . ? C14 C1 C2 C3 31.9(4) . . . . ? C1 C2 C3 C8 -109.6(4) . . . . ? C1 C2 C3 C4 56.4(5) . . . . ? C8 C3 C4 C5 18.1(5) . . . . ? C2 C3 C4 C5 -148.1(3) . . . . ? C8 C3 C4 P1 -165.5(3) . . . . ? C2 C3 C4 P1 28.3(5) . . . . ? C21 P1 C4 C5 -155.7(2) . . . . ? C31 P1 C4 C5 -41.3(3) . . . . ? Pd P1 C4 C5 77.7(3) . . . . ? C21 P1 C4 C3 27.8(3) . . . . ? C31 P1 C4 C3 142.2(3) . . . . ? Pd P1 C4 C3 -98.8(3) . . . . ? C3 C4 C5 C6 -2.7(5) . . . . ? P1 C4 C5 C6 -179.3(3) . . . . ? C4 C5 C6 C7 -14.8(5) . . . . ? C4 C5 C6 C9 153.1(3) . . . . ? C5 C6 C7 C8 16.2(5) . . . . ? C9 C6 C7 C8 -151.4(4) . . . . ? C6 C7 C8 C3 -0.4(6) . . . . ? C4 C3 C8 C7 -16.9(5) . . . . ? C2 C3 C8 C7 150.5(4) . . . . ? C7 C6 C9 C10 70.4(5) . . . . ? C5 C6 C9 C10 -96.8(4) . . . . ? C6 C9 C10 C11 20.4(5) . . . . ? C9 C10 C11 C16 -97.3(4) . . . . ? C9 C10 C11 C12 69.8(5) . . . . ? C16 C11 C12 C13 13.5(5) . . . . ? C10 C11 C12 C13 -154.0(3) . . . . ? C11 C12 C13 C14 1.3(5) . . . . ? C11 C12 C13 P2 178.0(3) . . . . ? C51 P2 C13 C12 27.8(3) . . . . ? C41 P2 C13 C12 141.1(3) . . . . ? Pd P2 C13 C12 -94.7(3) . . . . ? C51 P2 C13 C14 -155.5(3) . . . . ? C41 P2 C13 C14 -42.2(3) . . . . ? Pd P2 C13 C14 82.1(3) . . . . ? C12 C13 C14 C15 -16.0(5) . . . . ? P2 C13 C14 C15 167.3(2) . . . . ? C12 C13 C14 C1 149.8(3) . . . . ? P2 C13 C14 C1 -26.9(4) . . . . ? C2 C1 C14 C15 59.1(4) . . . . ? C2 C1 C14 C13 -106.2(4) . . . . ? C13 C14 C15 C16 15.9(5) . . . . ? C1 C14 C15 C16 -150.2(3) . . . . ? C14 C15 C16 C11 -1.3(6) . . . . ? C12 C11 C16 C15 -13.7(5) . . . . ? C10 C11 C16 C15 153.9(4) . . . . ? C4 P1 C21 C26 -130.5(3) . . . . ? C31 P1 C21 C26 118.8(3) . . . . ? Pd P1 C21 C26 5.3(3) . . . . ? C4 P1 C21 C22 43.4(3) . . . . ? C31 P1 C21 C22 -67.3(3) . . . . ? Pd P1 C21 C22 179.2(2) . . . . ? C26 C21 C22 C23 -0.9(5) . . . . ? P1 C21 C22 C23 -174.9(3) . . . . ? C21 C22 C23 C24 1.7(6) . . . . ? C22 C23 C24 C25 -1.5(6) . . . . ? C23 C24 C25 C26 0.7(6) . . . . ? C24 C25 C26 C21 0.1(6) . . . . ? C22 C21 C26 C25 0.0(5) . . . . ? P1 C21 C26 C25 174.0(3) . . . . ? C4 P1 C31 C36 108.9(3) . . . . ? C21 P1 C31 C36 -139.2(3) . . . . ? Pd P1 C31 C36 -23.0(3) . . . . ? C4 P1 C31 C32 -71.7(3) . . . . ? C21 P1 C31 C32 40.3(3) . . . . ? Pd P1 C31 C32 156.4(3) . . . . ? C36 C31 C32 C33 1.3(5) . . . . ? P1 C31 C32 C33 -178.2(3) . . . . ? C31 C32 C33 C34 -1.8(6) . . . . ? C32 C33 C34 C35 0.6(6) . . . . ? C33 C34 C35 C36 0.9(6) . . . . ? C32 C31 C36 C35 0.2(5) . . . . ? P1 C31 C36 C35 179.7(3) . . . . ? C34 C35 C36 C31 -1.4(6) . . . . ? C13 P2 C41 C42 142.9(3) . . . . ? C51 P2 C41 C42 -104.2(3) . . . . ? Pd P2 C41 C42 9.0(3) . . . . ? C13 P2 C41 C46 -38.1(3) . . . . ? C51 P2 C41 C46 74.9(3) . . . . ? Pd P2 C41 C46 -171.9(3) . . . . ? C46 C41 C42 C43 -0.1(6) . . . . ? P2 C41 C42 C43 179.0(3) . . . . ? C41 C42 C43 C44 0.4(7) . . . . ? C42 C43 C44 C45 -0.4(7) . . . . ? C43 C44 C45 C46 0.1(7) . . . . ? C44 C45 C46 C41 0.2(6) . . . . ? C42 C41 C46 C45 -0.2(5) . . . . ? P2 C41 C46 C45 -179.3(3) . . . . ? C13 P2 C51 C56 88.6(3) . . . . ? C41 P2 C51 C56 -23.3(4) . . . . ? Pd P2 C51 C56 -138.0(3) . . . . ? C13 P2 C51 C52 -96.4(3) . . . . ? C41 P2 C51 C52 151.7(3) . . . . ? Pd P2 C51 C52 36.9(3) . . . . ? C56 C51 C52 C53 0.5(5) . . . . ? P2 C51 C52 C53 -174.7(3) . . . . ? C51 C52 C53 C54 1.0(6) . . . . ? C52 C53 C54 C55 -1.1(7) . . . . ? C53 C54 C55 C56 -0.3(8) . . . . ? C54 C55 C56 C51 1.8(8) . . . . ? C52 C51 C56 C55 -1.9(6) . . . . ? P2 C51 C56 C55 173.2(4) . . . . ? N71 Pd N61 C62 -8.1(10) . . . . ? P2 Pd N61 C62 -26.4(15) . . . . ? P1 Pd N61 C62 168.1(10) . . . . ? Pd N61 C62 C63 -30(14) . . . . ? N61 Pd N71 C72 73(3) . . . . ? P2 Pd N71 C72 -110(3) . . . . ? P1 Pd N71 C72 37(4) . . . . ? Pd N71 C72 C73 80(15) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.589 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.078 # Attachment '- fro5548.cif' data_fro5548 _database_code_depnum_ccdc_archive 'CCDC 816640' #TrackingRef '- fro5548.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H34 P2' _chemical_formula_weight 576.61 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 8.9076(2) _cell_length_b 10.8103(2) _cell_length_c 16.3061(4) _cell_angle_alpha 92.514(1) _cell_angle_beta 93.546(1) _cell_angle_gamma 101.289(1) _cell_volume 1534.33(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3652 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9353 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14101 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 27.89 _reflns_number_total 7124 _reflns_number_gt 5989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+2.8567P] 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 7124 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2044 _refine_ls_wR_factor_gt 0.1905 _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 P1 P 0.25709(8) 0.65479(7) 0.32224(5) 0.0345(2) Uani 1 1 d . . . P2 P 0.24564(9) 0.72862(7) 0.07972(5) 0.0369(2) Uani 1 1 d . . . C1 C 0.3770(4) 0.4835(3) 0.1318(2) 0.0495(8) Uani 1 1 d . . . H1A H 0.3823 0.4099 0.0956 0.059 Uiso 1 1 calc R . . H1B H 0.2718 0.4979 0.1259 0.059 Uiso 1 1 calc R . . C2 C 0.4141(4) 0.4529(3) 0.2236(2) 0.0415(7) Uani 1 1 d . . . H2A H 0.3175 0.4287 0.2499 0.050 Uiso 1 1 calc R . . H2B H 0.4653 0.3805 0.2236 0.050 Uiso 1 1 calc R . . C3 C 0.5148(3) 0.5623(3) 0.27380(18) 0.0338(6) Uani 1 1 d . . . C4 C 0.4607(3) 0.6665(3) 0.30636(17) 0.0298(5) Uani 1 1 d . . . C5 C 0.5607(3) 0.7841(3) 0.31460(16) 0.0297(5) Uani 1 1 d . . . H5 H 0.5237 0.8552 0.3332 0.036 Uiso 1 1 calc R . . C6 C 0.7146(3) 0.7991(3) 0.29599(16) 0.0312(6) Uani 1 1 d . . . C7 C 0.7731(3) 0.6891(3) 0.28792(19) 0.0370(6) Uani 1 1 d . . . H7 H 0.8798 0.6938 0.2901 0.044 Uiso 1 1 calc R . . C8 C 0.6734(4) 0.5723(3) 0.2766(2) 0.0382(6) Uani 1 1 d . . . H8 H 0.7139 0.4987 0.2708 0.046 Uiso 1 1 calc R . . C9 C 0.8003(3) 0.9239(3) 0.2687(2) 0.0380(6) Uani 1 1 d . . . H9A H 0.8977 0.9490 0.3022 0.046 Uiso 1 1 calc R . . H9B H 0.7395 0.9889 0.2780 0.046 Uiso 1 1 calc R . . C10 C 0.8338(3) 0.9160(3) 0.1751(2) 0.0409(7) Uani 1 1 d . . . H10A H 0.8314 0.9978 0.1519 0.049 Uiso 1 1 calc R . . H10B H 0.9369 0.8986 0.1704 0.049 Uiso 1 1 calc R . . C11 C 0.7189(3) 0.8149(3) 0.12653(18) 0.0358(6) Uani 1 1 d . . . C12 C 0.5647(3) 0.8249(3) 0.11397(18) 0.0343(6) Uani 1 1 d . . . H12 H 0.5399 0.9055 0.1138 0.041 Uiso 1 1 calc R . . C13 C 0.4471(3) 0.7184(3) 0.10171(17) 0.0321(6) Uani 1 1 d . . . C14 C 0.4845(4) 0.5973(3) 0.10407(18) 0.0369(6) Uani 1 1 d . . . C15 C 0.6375(4) 0.5909(3) 0.0949(2) 0.0452(8) Uani 1 1 d . . . H15 H 0.6627 0.5124 0.0811 0.054 Uiso 1 1 calc R . . C16 C 0.7529(4) 0.6976(3) 0.1057(2) 0.0438(7) Uani 1 1 d . . . H16 H 0.8551 0.6909 0.0989 0.053 Uiso 1 1 calc R . . C21 C 0.2096(3) 0.5171(3) 0.38440(19) 0.0366(6) Uani 1 1 d . . . C22 C 0.3118(4) 0.4667(4) 0.4328(3) 0.0601(10) Uani 1 1 d . . . H22 H 0.4175 0.5006 0.4334 0.072 Uiso 1 1 calc R . . C23 C 0.2598(5) 0.3661(4) 0.4808(3) 0.0703(12) Uani 1 1 d . . . H23 H 0.3308 0.3330 0.5140 0.084 Uiso 1 1 calc R . . C24 C 0.1068(5) 0.3146(4) 0.4804(3) 0.0631(11) Uani 1 1 d . . . H24 H 0.0726 0.2462 0.5127 0.076 Uiso 1 1 calc R . . C25 C 0.0043(5) 0.3637(4) 0.4326(3) 0.0624(11) Uani 1 1 d . . . H25 H -0.1011 0.3291 0.4323 0.075 Uiso 1 1 calc R . . C26 C 0.0544(4) 0.4642(3) 0.3846(2) 0.0487(8) Uani 1 1 d . . . H26 H -0.0175 0.4970 0.3519 0.058 Uiso 1 1 calc R . . C31 C 0.2624(3) 0.7833(3) 0.40037(19) 0.0363(6) Uani 1 1 d . . . C32 C 0.3478(4) 0.7956(3) 0.4759(2) 0.0466(8) Uani 1 1 d . . . H32 H 0.4080 0.7360 0.4892 0.056 Uiso 1 1 calc R . . C33 C 0.3439(5) 0.8961(4) 0.5317(2) 0.0555(9) Uani 1 1 d . . . H33 H 0.4025 0.9044 0.5823 0.067 Uiso 1 1 calc R . . C34 C 0.2553(5) 0.9832(4) 0.5133(3) 0.0571(10) Uani 1 1 d . . . H34 H 0.2527 1.0504 0.5515 0.069 Uiso 1 1 calc R . . C35 C 0.1711(4) 0.9723(4) 0.4398(3) 0.0551(9) Uani 1 1 d . . . H35 H 0.1108 1.0322 0.4273 0.066 Uiso 1 1 calc R . . C36 C 0.1741(4) 0.8728(3) 0.3832(2) 0.0433(7) Uani 1 1 d . . . H36 H 0.1154 0.8660 0.3327 0.052 Uiso 1 1 calc R . . C41 C 0.2355(3) 0.7260(3) -0.0327(2) 0.0376(6) Uani 1 1 d . . . C42 C 0.1021(4) 0.6572(3) -0.0751(2) 0.0489(8) Uani 1 1 d . . . H42 H 0.0236 0.6122 -0.0457 0.059 Uiso 1 1 calc R . . C43 C 0.0847(5) 0.6546(4) -0.1601(3) 0.0604(10) Uani 1 1 d . . . H43 H -0.0055 0.6078 -0.1880 0.072 Uiso 1 1 calc R . . C44 C 0.1977(5) 0.7196(4) -0.2038(2) 0.0555(10) Uani 1 1 d . . . H44 H 0.1840 0.7186 -0.2614 0.067 Uiso 1 1 calc R . . C45 C 0.3332(5) 0.7875(3) -0.1632(2) 0.0493(8) Uani 1 1 d . . . H45 H 0.4113 0.8315 -0.1932 0.059 Uiso 1 1 calc R . . C46 C 0.3513(4) 0.7891(3) -0.0782(2) 0.0437(7) Uani 1 1 d . . . H46 H 0.4432 0.8335 -0.0507 0.052 Uiso 1 1 calc R . . C51 C 0.2427(3) 0.8946(3) 0.10636(19) 0.0338(6) Uani 1 1 d . . . C52 C 0.2766(4) 0.9387(3) 0.1878(2) 0.0423(7) Uani 1 1 d . . . H52 H 0.3114 0.8862 0.2260 0.051 Uiso 1 1 calc R . . C53 C 0.2602(4) 1.0589(3) 0.2139(2) 0.0486(8) Uani 1 1 d . . . H53 H 0.2842 1.0870 0.2694 0.058 Uiso 1 1 calc R . . C54 C 0.2086(4) 1.1374(3) 0.1586(2) 0.0456(8) Uani 1 1 d . . . H54 H 0.1954 1.2183 0.1763 0.055 Uiso 1 1 calc R . . C55 C 0.1772(4) 1.0956(3) 0.0778(2) 0.0504(8) Uani 1 1 d . . . H55 H 0.1435 1.1489 0.0397 0.060 Uiso 1 1 calc R . . C56 C 0.1943(4) 0.9758(3) 0.0514(2) 0.0440(7) Uani 1 1 d . . . H56 H 0.1728 0.9492 -0.0045 0.053 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 0.0299(4) 0.0303(4) 0.0425(4) 0.0000(3) 0.0047(3) 0.0038(3) P2 0.0306(4) 0.0339(4) 0.0458(4) 0.0004(3) 0.0046(3) 0.0054(3) C1 0.056(2) 0.0301(15) 0.057(2) -0.0027(14) -0.0150(16) 0.0045(14) C2 0.0450(17) 0.0282(14) 0.0501(18) -0.0045(12) 0.0099(14) 0.0041(12) C3 0.0388(15) 0.0272(13) 0.0354(14) 0.0005(10) 0.0064(11) 0.0056(11) C4 0.0306(13) 0.0281(13) 0.0303(13) 0.0010(10) 0.0036(10) 0.0050(10) C5 0.0302(13) 0.0294(13) 0.0298(13) -0.0007(10) 0.0027(10) 0.0067(10) C6 0.0310(13) 0.0329(14) 0.0285(13) -0.0004(10) -0.0008(10) 0.0047(11) C7 0.0303(14) 0.0422(16) 0.0398(15) 0.0028(12) 0.0016(11) 0.0107(12) C8 0.0414(16) 0.0322(14) 0.0450(16) 0.0046(12) 0.0073(13) 0.0151(12) C9 0.0303(14) 0.0336(14) 0.0478(17) 0.0030(12) 0.0036(12) 0.0006(11) C10 0.0293(14) 0.0462(17) 0.0479(18) 0.0097(14) 0.0113(12) 0.0049(12) C11 0.0333(14) 0.0419(16) 0.0343(14) 0.0067(12) 0.0084(11) 0.0097(12) C12 0.0343(14) 0.0341(14) 0.0370(15) 0.0077(11) 0.0070(11) 0.0105(11) C13 0.0347(14) 0.0339(14) 0.0295(13) 0.0027(10) 0.0036(11) 0.0103(11) C14 0.0467(17) 0.0329(14) 0.0309(14) -0.0041(11) -0.0027(12) 0.0106(12) C15 0.056(2) 0.0446(17) 0.0399(16) -0.0076(13) -0.0010(14) 0.0253(15) C16 0.0426(17) 0.057(2) 0.0378(16) 0.0026(14) 0.0104(13) 0.0232(15) C21 0.0365(15) 0.0314(14) 0.0408(16) 0.0009(11) 0.0100(12) 0.0019(11) C22 0.0444(19) 0.058(2) 0.080(3) 0.032(2) 0.0111(18) 0.0072(17) C23 0.065(3) 0.065(3) 0.087(3) 0.039(2) 0.019(2) 0.015(2) C24 0.080(3) 0.0408(19) 0.067(3) 0.0110(17) 0.032(2) 0.0000(19) C25 0.052(2) 0.056(2) 0.070(3) 0.0033(19) 0.0215(19) -0.0167(18) C26 0.0376(17) 0.0507(19) 0.053(2) 0.0001(15) 0.0067(14) -0.0023(14) C31 0.0312(14) 0.0345(14) 0.0421(16) -0.0005(12) 0.0098(12) 0.0026(11) C32 0.0444(18) 0.0510(19) 0.0441(18) -0.0001(14) 0.0062(14) 0.0085(15) C33 0.054(2) 0.064(2) 0.0426(19) -0.0105(16) 0.0062(16) -0.0011(18) C34 0.055(2) 0.054(2) 0.059(2) -0.0196(17) 0.0151(18) 0.0021(17) C35 0.051(2) 0.0461(19) 0.070(2) -0.0093(17) 0.0130(18) 0.0147(16) C36 0.0370(16) 0.0394(16) 0.0532(19) -0.0051(14) 0.0078(14) 0.0076(13) C41 0.0329(14) 0.0361(15) 0.0446(16) -0.0061(12) -0.0008(12) 0.0112(12) C42 0.0376(16) 0.0499(19) 0.058(2) -0.0094(16) -0.0008(15) 0.0110(14) C43 0.050(2) 0.070(3) 0.061(2) -0.0207(19) -0.0116(18) 0.0214(19) C44 0.068(2) 0.059(2) 0.0450(19) -0.0123(16) -0.0083(17) 0.0329(19) C45 0.061(2) 0.0457(18) 0.0446(18) -0.0008(14) 0.0077(16) 0.0187(16) C46 0.0436(17) 0.0408(16) 0.0460(18) -0.0052(13) -0.0001(14) 0.0092(13) C51 0.0272(13) 0.0353(14) 0.0404(15) 0.0046(11) 0.0061(11) 0.0083(11) C52 0.0406(16) 0.0440(17) 0.0445(17) 0.0034(13) 0.0007(13) 0.0146(14) C53 0.0468(18) 0.0463(18) 0.0509(19) -0.0081(15) -0.0013(15) 0.0089(15) C54 0.0421(17) 0.0304(15) 0.063(2) -0.0019(14) 0.0100(15) 0.0042(13) C55 0.056(2) 0.0421(18) 0.060(2) 0.0160(15) 0.0126(17) 0.0209(16) C56 0.0516(19) 0.0459(17) 0.0392(16) 0.0065(13) 0.0076(14) 0.0192(15) _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 C4 1.828(3) . ? P1 C21 1.834(3) . ? P1 C31 1.835(3) . ? P2 C41 1.829(3) . ? P2 C51 1.833(3) . ? P2 C13 1.834(3) . ? C1 C14 1.508(5) . ? C1 C2 1.576(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.511(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C8 1.393(4) . ? C3 C4 1.405(4) . ? C4 C5 1.398(4) . ? C5 C6 1.402(4) . ? C5 H5 0.9400 . ? C6 C7 1.393(4) . ? C6 C9 1.513(4) . ? C7 C8 1.392(4) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C9 C10 1.576(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.502(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C16 1.393(4) . ? C11 C12 1.402(4) . ? C12 C13 1.394(4) . ? C12 H12 0.9400 . ? C13 C14 1.414(4) . ? C14 C15 1.395(5) . ? C15 C16 1.384(5) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C21 C22 1.374(5) . ? C21 C26 1.390(4) . ? C22 C23 1.391(5) . ? C22 H22 0.9400 . ? C23 C24 1.367(6) . ? C23 H23 0.9400 . ? C24 C25 1.364(7) . ? C24 H24 0.9400 . ? C25 C26 1.385(5) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C36 1.388(4) . ? C31 C32 1.394(5) . ? C32 C33 1.393(5) . ? C32 H32 0.9400 . ? C33 C34 1.373(6) . ? C33 H33 0.9400 . ? C34 C35 1.362(6) . ? C34 H34 0.9400 . ? C35 C36 1.392(5) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C41 C46 1.394(5) . ? C41 C42 1.397(4) . ? C42 C43 1.383(6) . ? C42 H42 0.9400 . ? C43 C44 1.368(6) . ? C43 H43 0.9400 . ? C44 C45 1.394(6) . ? C44 H44 0.9400 . ? C45 C46 1.384(5) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? C51 C52 1.385(5) . ? C51 C56 1.390(4) . ? C52 C53 1.387(5) . ? C52 H52 0.9400 . ? C53 C54 1.383(5) . ? C53 H53 0.9400 . ? C54 C55 1.368(5) . ? C54 H54 0.9400 . ? C55 C56 1.386(5) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 P1 C21 104.18(13) . . ? C4 P1 C31 101.98(13) . . ? C21 P1 C31 100.58(14) . . ? C41 P2 C51 101.50(14) . . ? C41 P2 C13 100.51(13) . . ? C51 P2 C13 103.66(13) . . ? C14 C1 C2 113.6(3) . . ? C14 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C14 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 113.5(3) . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C8 C3 C4 116.9(3) . . ? C8 C3 C2 118.6(3) . . ? C4 C3 C2 123.6(3) . . ? C5 C4 C3 118.4(3) . . ? C5 C4 P1 120.1(2) . . ? C3 C4 P1 120.8(2) . . ? C4 C5 C6 122.0(3) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 116.4(3) . . ? C7 C6 C9 121.5(3) . . ? C5 C6 C9 120.8(3) . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C3 C8 C7 121.4(3) . . ? C3 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C6 C9 C10 112.0(2) . . ? C6 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C6 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 112.0(2) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C16 C11 C12 116.3(3) . . ? C16 C11 C10 121.4(3) . . ? C12 C11 C10 121.2(3) . . ? C13 C12 C11 121.7(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.0(3) . . ? C12 C13 P2 122.6(2) . . ? C14 C13 P2 118.4(2) . . ? C15 C14 C13 116.6(3) . . ? C15 C14 C1 119.1(3) . . ? C13 C14 C1 123.1(3) . . ? C16 C15 C14 121.3(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C11 120.5(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C22 C21 C26 118.2(3) . . ? C22 C21 P1 126.1(2) . . ? C26 C21 P1 115.6(3) . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.9(4) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C25 C24 C23 119.3(4) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.5(4) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.7(4) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C36 C31 C32 118.2(3) . . ? C36 C31 P1 117.6(2) . . ? C32 C31 P1 124.1(2) . . ? C33 C32 C31 120.1(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 120.5(4) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 120.0(3) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 120.2(4) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C31 C36 C35 120.9(3) . . ? C31 C36 H36 119.5 . . ? C35 C36 H36 119.6 . . ? C46 C41 C42 118.4(3) . . ? C46 C41 P2 124.2(2) . . ? C42 C41 P2 117.4(3) . . ? C43 C42 C41 120.5(4) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C44 C43 C42 120.5(4) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C45 120.4(4) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C46 C45 C44 119.2(4) . . ? C46 C45 H45 120.4 . . ? C44 C45 H45 120.4 . . ? C45 C46 C41 121.1(3) . . ? C45 C46 H46 119.5 . . ? C41 C46 H46 119.5 . . ? C52 C51 C56 117.6(3) . . ? C52 C51 P2 118.3(2) . . ? C56 C51 P2 123.8(2) . . ? C51 C52 C53 121.3(3) . . ? C51 C52 H52 119.3 . . ? C53 C52 H52 119.3 . . ? C54 C53 C52 120.2(3) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C55 C54 C53 119.0(3) . . ? C55 C54 H54 120.5 . . ? C53 C54 H54 120.5 . . ? C54 C55 C56 120.9(3) . . ? C54 C55 H55 119.5 . . ? C56 C55 H55 119.5 . . ? C55 C56 C51 120.9(3) . . ? C55 C56 H56 119.6 . . ? C51 C56 H56 119.6 . . ? 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 C14 C1 C2 C3 17.8(4) . . . . ? C1 C2 C3 C8 -90.9(4) . . . . ? C1 C2 C3 C4 77.7(4) . . . . ? C8 C3 C4 C5 20.1(4) . . . . ? C2 C3 C4 C5 -148.6(3) . . . . ? C8 C3 C4 P1 -169.5(2) . . . . ? C2 C3 C4 P1 21.8(4) . . . . ? C21 P1 C4 C5 -136.3(2) . . . . ? C31 P1 C4 C5 -31.9(3) . . . . ? C21 P1 C4 C3 53.5(3) . . . . ? C31 P1 C4 C3 157.8(2) . . . . ? C3 C4 C5 C6 -3.8(4) . . . . ? P1 C4 C5 C6 -174.3(2) . . . . ? C4 C5 C6 C7 -14.8(4) . . . . ? C4 C5 C6 C9 152.8(3) . . . . ? C5 C6 C7 C8 16.9(4) . . . . ? C9 C6 C7 C8 -150.6(3) . . . . ? C4 C3 C8 C7 -18.3(4) . . . . ? C2 C3 C8 C7 151.0(3) . . . . ? C6 C7 C8 C3 -0.5(5) . . . . ? C7 C6 C9 C10 57.3(4) . . . . ? C5 C6 C9 C10 -109.6(3) . . . . ? C6 C9 C10 C11 26.1(4) . . . . ? C9 C10 C11 C16 -100.5(3) . . . . ? C9 C10 C11 C12 67.1(4) . . . . ? C16 C11 C12 C13 15.8(4) . . . . ? C10 C11 C12 C13 -152.4(3) . . . . ? C11 C12 C13 C14 1.6(4) . . . . ? C11 C12 C13 P2 -176.7(2) . . . . ? C41 P2 C13 C12 90.1(3) . . . . ? C51 P2 C13 C12 -14.6(3) . . . . ? C41 P2 C13 C14 -88.2(2) . . . . ? C51 P2 C13 C14 167.1(2) . . . . ? C12 C13 C14 C15 -17.9(4) . . . . ? P2 C13 C14 C15 160.4(2) . . . . ? C12 C13 C14 C1 149.9(3) . . . . ? P2 C13 C14 C1 -31.7(4) . . . . ? C2 C1 C14 C15 68.3(4) . . . . ? C2 C1 C14 C13 -99.2(4) . . . . ? C13 C14 C15 C16 17.2(5) . . . . ? C1 C14 C15 C16 -151.1(3) . . . . ? C14 C15 C16 C11 0.3(5) . . . . ? C12 C11 C16 C15 -16.7(4) . . . . ? C10 C11 C16 C15 151.4(3) . . . . ? C4 P1 C21 C22 22.0(4) . . . . ? C31 P1 C21 C22 -83.4(3) . . . . ? C4 P1 C21 C26 -161.3(2) . . . . ? C31 P1 C21 C26 93.3(3) . . . . ? C26 C21 C22 C23 -0.4(6) . . . . ? P1 C21 C22 C23 176.2(4) . . . . ? C21 C22 C23 C24 0.5(8) . . . . ? C22 C23 C24 C25 -0.5(7) . . . . ? C23 C24 C25 C26 0.3(7) . . . . ? C24 C25 C26 C21 -0.2(6) . . . . ? C22 C21 C26 C25 0.2(5) . . . . ? P1 C21 C26 C25 -176.8(3) . . . . ? C4 P1 C31 C36 125.6(2) . . . . ? C21 P1 C31 C36 -127.3(2) . . . . ? C4 P1 C31 C32 -55.3(3) . . . . ? C21 P1 C31 C32 51.9(3) . . . . ? C36 C31 C32 C33 -0.4(5) . . . . ? P1 C31 C32 C33 -179.6(3) . . . . ? C31 C32 C33 C34 0.6(6) . . . . ? C32 C33 C34 C35 -0.5(6) . . . . ? C33 C34 C35 C36 0.2(6) . . . . ? C32 C31 C36 C35 0.2(5) . . . . ? P1 C31 C36 C35 179.4(3) . . . . ? C34 C35 C36 C31 -0.1(6) . . . . ? C51 P2 C41 C46 66.7(3) . . . . ? C13 P2 C41 C46 -39.7(3) . . . . ? C51 P2 C41 C42 -112.6(3) . . . . ? C13 P2 C41 C42 140.9(3) . . . . ? C46 C41 C42 C43 -1.5(5) . . . . ? P2 C41 C42 C43 177.9(3) . . . . ? C41 C42 C43 C44 -0.1(6) . . . . ? C42 C43 C44 C45 1.2(6) . . . . ? C43 C44 C45 C46 -0.6(5) . . . . ? C44 C45 C46 C41 -1.1(5) . . . . ? C42 C41 C46 C45 2.2(5) . . . . ? P2 C41 C46 C45 -177.2(2) . . . . ? C41 P2 C51 C52 -168.6(2) . . . . ? C13 P2 C51 C52 -64.6(3) . . . . ? C41 P2 C51 C56 17.9(3) . . . . ? C13 P2 C51 C56 121.8(3) . . . . ? C56 C51 C52 C53 1.1(5) . . . . ? P2 C51 C52 C53 -172.8(3) . . . . ? C51 C52 C53 C54 0.2(5) . . . . ? C52 C53 C54 C55 -1.2(5) . . . . ? C53 C54 C55 C56 0.9(5) . . . . ? C54 C55 C56 C51 0.5(5) . . . . ? C52 C51 C56 C55 -1.5(5) . . . . ? P2 C51 C56 C55 172.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.879 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.069 # Attachment '- fro5461.cif' data_fro5461 _database_code_depnum_ccdc_archive 'CCDC 816641' #TrackingRef '- fro5461.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Br P' _chemical_formula_weight 471.35 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' Br Br -0.2901 2.4595 '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 8.7264(2) _cell_length_b 11.1117(3) _cell_length_c 12.1982(3) _cell_angle_alpha 81.623(1) _cell_angle_beta 73.365(1) _cell_angle_gamma 78.493(1) _cell_volume 1105.57(5) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2750 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5494 _exptl_absorpt_correction_T_max 0.7334 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10091 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 27.86 _reflns_number_total 5012 _reflns_number_gt 4481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+1.2574P] 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 5012 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1252 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Br1 Br -0.44227(4) 0.83213(3) 1.93112(3) 0.04917(12) Uani 1 1 d . . . P1 P -0.31181(8) 0.76615(6) 1.61499(5) 0.03027(15) Uani 1 1 d . . . C11 C -0.1165(3) 0.7769(2) 1.63972(19) 0.0278(5) Uani 1 1 d . . . C12 C -0.0039(3) 0.6716(2) 1.6565(2) 0.0302(5) Uani 1 1 d . . . H12 H -0.0287 0.5932 1.6560 0.036 Uiso 1 1 calc R . . C13 C 0.1439(3) 0.6810(3) 1.6738(2) 0.0338(5) Uani 1 1 d . . . C14 C 0.1930(3) 0.7954(3) 1.6456(2) 0.0383(6) Uani 1 1 d . . . H14 H 0.3018 0.8016 1.6370 0.046 Uiso 1 1 calc R . . C15 C 0.0829(4) 0.9005(3) 1.6300(2) 0.0372(6) Uani 1 1 d . . . H15 H 0.1179 0.9774 1.6112 0.045 Uiso 1 1 calc R . . C16 C -0.0792(3) 0.8941(2) 1.6419(2) 0.0305(5) Uani 1 1 d . . . C17 C 0.2319(3) 0.5778(3) 1.7398(3) 0.0430(6) Uani 1 1 d . . . H17A H 0.3453 0.5886 1.7235 0.052 Uiso 1 1 calc R . . H17B H 0.2308 0.4988 1.7135 0.052 Uiso 1 1 calc R . . C18 C 0.1528(4) 0.5745(3) 1.8727(3) 0.0545(8) Uani 1 1 d . . . H18A H 0.0896 0.5070 1.8968 0.065 Uiso 1 1 calc R . . H18B H 0.2390 0.5571 1.9124 0.065 Uiso 1 1 calc R . . C21 C -0.2154(3) 0.8210(3) 1.9112(2) 0.0353(5) Uani 1 1 d . . . C22 C -0.1234(4) 0.7059(3) 1.9247(2) 0.0382(6) Uani 1 1 d . . . H22 H -0.1733 0.6353 1.9447 0.046 Uiso 1 1 calc R . . C23 C 0.0430(4) 0.6943(3) 1.9086(2) 0.0433(7) Uani 1 1 d . . . C24 C 0.1037(4) 0.8023(4) 1.9039(3) 0.0517(8) Uani 1 1 d . . . H24 H 0.2079 0.7979 1.9134 0.062 Uiso 1 1 calc R . . C25 C 0.0108(4) 0.9164(3) 1.8853(2) 0.0492(8) Uani 1 1 d . . . H25 H 0.0551 0.9883 1.8795 0.059 Uiso 1 1 calc R . . C26 C -0.1463(4) 0.9270(3) 1.8749(2) 0.0401(6) Uani 1 1 d . . . C27 C -0.2166(4) 1.0359(3) 1.8048(3) 0.0449(7) Uani 1 1 d . . . H27A H -0.1578 1.1042 1.7982 0.054 Uiso 1 1 calc R . . H27B H -0.3303 1.0630 1.8450 0.054 Uiso 1 1 calc R . . C28 C -0.2068(4) 1.0048(2) 1.6796(2) 0.0411(6) Uani 1 1 d . . . H28A H -0.3128 0.9887 1.6785 0.049 Uiso 1 1 calc R . . H28B H -0.1823 1.0765 1.6248 0.049 Uiso 1 1 calc R . . C31 C -0.2549(3) 0.7758(2) 1.4572(2) 0.0316(5) Uani 1 1 d . . . C32 C -0.1072(3) 0.7166(3) 1.3913(2) 0.0391(6) Uani 1 1 d . . . H32 H -0.0298 0.6707 1.4278 0.047 Uiso 1 1 calc R . . C33 C -0.0746(4) 0.7252(3) 1.2732(3) 0.0448(7) Uani 1 1 d . . . H33 H 0.0239 0.6837 1.2298 0.054 Uiso 1 1 calc R . . C34 C -0.1865(4) 0.7950(3) 1.2181(3) 0.0488(7) Uani 1 1 d . . . H34 H -0.1640 0.8007 1.1375 0.059 Uiso 1 1 calc R . . C35 C -0.3299(4) 0.8554(3) 1.2816(3) 0.0508(8) Uani 1 1 d . . . H35 H -0.4050 0.9036 1.2443 0.061 Uiso 1 1 calc R . . C36 C -0.3651(4) 0.8458(3) 1.4007(2) 0.0408(6) Uani 1 1 d . . . H36 H -0.4644 0.8870 1.4434 0.049 Uiso 1 1 calc R . . C41 C -0.3270(3) 0.6018(3) 1.6535(2) 0.0330(5) Uani 1 1 d . . . C42 C -0.3531(4) 0.5570(3) 1.7698(3) 0.0421(6) Uani 1 1 d . . . H42 H -0.3508 0.6090 1.8233 0.050 Uiso 1 1 calc R . . C43 C -0.3820(4) 0.4386(3) 1.8074(3) 0.0491(7) Uani 1 1 d . . . H43 H -0.3978 0.4102 1.8857 0.059 Uiso 1 1 calc R . . C44 C -0.3879(4) 0.3613(3) 1.7296(3) 0.0528(8) Uani 1 1 d . . . H44 H -0.4090 0.2807 1.7550 0.063 Uiso 1 1 calc R . . C45 C -0.3628(4) 0.4031(3) 1.6155(3) 0.0542(8) Uani 1 1 d . . . H45 H -0.3668 0.3509 1.5626 0.065 Uiso 1 1 calc R . . C46 C -0.3314(4) 0.5225(3) 1.5772(3) 0.0438(7) Uani 1 1 d . . . H46 H -0.3130 0.5495 1.4986 0.053 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 Br1 0.04263(18) 0.0528(2) 0.04486(19) -0.00853(13) 0.00048(13) -0.00616(13) P1 0.0277(3) 0.0358(3) 0.0262(3) -0.0035(2) -0.0064(2) -0.0035(2) C11 0.0282(11) 0.0341(12) 0.0205(10) -0.0044(9) -0.0039(8) -0.0063(9) C12 0.0296(11) 0.0323(12) 0.0274(11) -0.0054(9) -0.0043(9) -0.0046(9) C13 0.0277(11) 0.0427(14) 0.0287(12) -0.0062(10) -0.0037(9) -0.0040(10) C14 0.0331(13) 0.0529(16) 0.0298(13) -0.0014(11) -0.0047(10) -0.0163(12) C15 0.0449(15) 0.0423(14) 0.0262(12) 0.0033(10) -0.0074(11) -0.0191(12) C16 0.0399(13) 0.0302(12) 0.0200(10) 0.0007(9) -0.0065(9) -0.0069(10) C17 0.0312(13) 0.0483(16) 0.0470(16) -0.0004(13) -0.0121(12) -0.0012(12) C18 0.0489(18) 0.060(2) 0.0463(18) 0.0101(15) -0.0144(14) 0.0007(15) C21 0.0442(14) 0.0402(14) 0.0200(11) -0.0037(9) -0.0039(10) -0.0094(11) C22 0.0476(15) 0.0432(14) 0.0225(11) 0.0030(10) -0.0082(11) -0.0105(12) C23 0.0504(16) 0.0543(17) 0.0240(12) 0.0052(11) -0.0124(11) -0.0087(13) C24 0.0527(18) 0.077(2) 0.0321(14) -0.0009(14) -0.0166(13) -0.0220(17) C25 0.067(2) 0.0590(19) 0.0286(14) -0.0073(13) -0.0089(13) -0.0288(16) C26 0.0562(17) 0.0393(14) 0.0237(12) -0.0093(10) -0.0025(11) -0.0126(12) C27 0.0607(19) 0.0309(13) 0.0383(15) -0.0066(11) -0.0044(13) -0.0069(12) C28 0.0543(17) 0.0286(12) 0.0369(14) 0.0000(10) -0.0135(12) 0.0007(12) C31 0.0316(12) 0.0365(13) 0.0279(12) -0.0022(10) -0.0077(9) -0.0089(10) C32 0.0385(14) 0.0453(15) 0.0324(13) -0.0062(11) -0.0075(11) -0.0053(12) C33 0.0490(16) 0.0505(17) 0.0323(14) -0.0085(12) -0.0004(12) -0.0144(13) C34 0.0622(19) 0.063(2) 0.0275(13) 0.0001(13) -0.0114(13) -0.0289(16) C35 0.0550(18) 0.065(2) 0.0379(16) 0.0074(14) -0.0233(14) -0.0157(16) C36 0.0359(14) 0.0512(16) 0.0361(14) -0.0005(12) -0.0135(11) -0.0060(12) C41 0.0245(11) 0.0397(13) 0.0346(13) -0.0036(10) -0.0069(9) -0.0067(10) C42 0.0448(15) 0.0464(16) 0.0398(15) 0.0012(12) -0.0163(12) -0.0151(13) C43 0.0493(17) 0.0503(17) 0.0493(18) 0.0110(14) -0.0197(14) -0.0134(14) C44 0.0448(16) 0.0320(14) 0.076(2) 0.0002(14) -0.0122(16) -0.0035(12) C45 0.0546(19) 0.0442(17) 0.062(2) -0.0195(15) -0.0022(16) -0.0122(14) C46 0.0476(16) 0.0445(15) 0.0374(15) -0.0096(12) -0.0015(12) -0.0136(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C21 1.905(3) . ? P1 C31 1.837(3) . ? P1 C41 1.839(3) . ? P1 C11 1.843(2) . ? C11 C12 1.400(3) . ? C11 C16 1.410(3) . ? C12 C13 1.391(4) . ? C12 H12 0.9400 . ? C13 C14 1.387(4) . ? C13 C17 1.511(4) . ? C14 C15 1.384(4) . ? C14 H14 0.9400 . ? C15 C16 1.396(4) . ? C15 H15 0.9400 . ? C16 C28 1.513(4) . ? C17 C18 1.568(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C23 1.518(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C21 C22 1.383(4) . ? C21 C26 1.388(4) . ? C22 C23 1.390(4) . ? C22 H22 0.9400 . ? C23 C24 1.393(5) . ? C24 C25 1.388(5) . ? C24 H24 0.9400 . ? C25 C26 1.393(5) . ? C25 H25 0.9400 . ? C26 C27 1.508(4) . ? C27 C28 1.589(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C31 C36 1.389(4) . ? C31 C32 1.401(4) . ? C32 C33 1.379(4) . ? C32 H32 0.9400 . ? C33 C34 1.389(5) . ? C33 H33 0.9400 . ? C34 C35 1.370(5) . ? C34 H34 0.9400 . ? C35 C36 1.389(4) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C41 C46 1.385(4) . ? C41 C42 1.402(4) . ? C42 C43 1.376(4) . ? C42 H42 0.9400 . ? C43 C44 1.388(5) . ? C43 H43 0.9400 . ? C44 C45 1.371(5) . ? C44 H44 0.9400 . ? C45 C46 1.394(5) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C41 101.82(12) . . ? C31 P1 C11 100.16(11) . . ? C41 P1 C11 103.29(11) . . ? C12 C11 C16 119.0(2) . . ? C12 C11 P1 121.79(19) . . ? C16 C11 P1 119.17(19) . . ? C13 C12 C11 121.3(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 117.2(2) . . ? C14 C13 C17 120.9(3) . . ? C12 C13 C17 121.0(3) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 121.1(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 116.9(2) . . ? C15 C16 C28 118.6(2) . . ? C11 C16 C28 123.2(2) . . ? C13 C17 C18 112.1(2) . . ? C13 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C13 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C23 C18 C17 112.9(3) . . ? C23 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? C23 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C22 C21 C26 122.2(3) . . ? C22 C21 Br1 118.6(2) . . ? C26 C21 Br1 118.9(2) . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 116.8(3) . . ? C22 C23 C18 119.8(3) . . ? C24 C23 C18 122.1(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 121.7(3) . . ? C24 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? C21 C26 C25 115.0(3) . . ? C21 C26 C27 123.0(3) . . ? C25 C26 C27 120.6(3) . . ? C26 C27 C28 112.6(2) . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27B 109.1 . . ? C28 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C16 C28 C27 112.6(2) . . ? C16 C28 H28A 109.1 . . ? C27 C28 H28A 109.1 . . ? C16 C28 H28B 109.1 . . ? C27 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C36 C31 C32 118.5(2) . . ? C36 C31 P1 117.8(2) . . ? C32 C31 P1 123.7(2) . . ? C33 C32 C31 120.5(3) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.3(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 119.7(3) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 120.5(3) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C36 C31 120.5(3) . . ? C35 C36 H36 119.7 . . ? C31 C36 H36 119.7 . . ? C46 C41 C42 117.5(3) . . ? C46 C41 P1 124.2(2) . . ? C42 C41 P1 117.9(2) . . ? C43 C42 C41 121.6(3) . . ? C43 C42 H42 119.2 . . ? C41 C42 H42 119.2 . . ? C42 C43 C44 119.8(3) . . ? C42 C43 H43 120.1 . . ? C44 C43 H43 120.1 . . ? C45 C44 C43 119.6(3) . . ? C45 C44 H44 120.2 . . ? C43 C44 H44 120.2 . . ? C44 C45 C46 120.5(3) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C41 C46 C45 120.9(3) . . ? C41 C46 H46 119.5 . . ? C45 C46 H46 119.5 . . ? 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 C31 P1 C11 C12 -91.8(2) . . . . ? C41 P1 C11 C12 13.0(2) . . . . ? C31 P1 C11 C16 88.2(2) . . . . ? C41 P1 C11 C16 -166.96(19) . . . . ? C16 C11 C12 C13 -0.7(4) . . . . ? P1 C11 C12 C13 179.27(19) . . . . ? C11 C12 C13 C14 -15.8(4) . . . . ? C11 C12 C13 C17 153.6(3) . . . . ? C12 C13 C14 C15 16.2(4) . . . . ? C17 C13 C14 C15 -153.1(3) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C11 -16.4(4) . . . . ? C14 C15 C16 C28 151.5(3) . . . . ? C12 C11 C16 C15 16.6(3) . . . . ? P1 C11 C16 C15 -163.39(18) . . . . ? C12 C11 C16 C28 -150.7(2) . . . . ? P1 C11 C16 C28 29.3(3) . . . . ? C14 C13 C17 C18 93.0(3) . . . . ? C12 C13 C17 C18 -76.0(4) . . . . ? C13 C17 C18 C23 -17.9(4) . . . . ? C26 C21 C22 C23 4.0(4) . . . . ? Br1 C21 C22 C23 178.8(2) . . . . ? C21 C22 C23 C24 13.6(4) . . . . ? C21 C22 C23 C18 -153.8(3) . . . . ? C17 C18 C23 C22 96.7(3) . . . . ? C17 C18 C23 C24 -70.0(4) . . . . ? C22 C23 C24 C25 -16.6(4) . . . . ? C18 C23 C24 C25 150.4(3) . . . . ? C23 C24 C25 C26 2.3(5) . . . . ? C22 C21 C26 C25 -17.9(4) . . . . ? Br1 C21 C26 C25 167.3(2) . . . . ? C22 C21 C26 C27 148.5(3) . . . . ? Br1 C21 C26 C27 -26.3(3) . . . . ? C24 C25 C26 C21 14.7(4) . . . . ? C24 C25 C26 C27 -152.1(3) . . . . ? C21 C26 C27 C28 -66.6(4) . . . . ? C25 C26 C27 C28 99.0(3) . . . . ? C15 C16 C28 C27 -62.9(3) . . . . ? C11 C16 C28 C27 104.2(3) . . . . ? C26 C27 C28 C16 -21.2(4) . . . . ? C41 P1 C31 C36 114.3(2) . . . . ? C11 P1 C31 C36 -139.7(2) . . . . ? C41 P1 C31 C32 -65.7(3) . . . . ? C11 P1 C31 C32 40.4(3) . . . . ? C36 C31 C32 C33 -1.7(4) . . . . ? P1 C31 C32 C33 178.2(2) . . . . ? C31 C32 C33 C34 1.4(5) . . . . ? C32 C33 C34 C35 0.0(5) . . . . ? C33 C34 C35 C36 -1.0(5) . . . . ? C34 C35 C36 C31 0.6(5) . . . . ? C32 C31 C36 C35 0.7(4) . . . . ? P1 C31 C36 C35 -179.2(2) . . . . ? C31 P1 C41 C46 -13.5(3) . . . . ? C11 P1 C41 C46 -117.1(2) . . . . ? C31 P1 C41 C42 173.6(2) . . . . ? C11 P1 C41 C42 70.0(2) . . . . ? C46 C41 C42 C43 0.0(4) . . . . ? P1 C41 C42 C43 173.4(2) . . . . ? C41 C42 C43 C44 -0.8(5) . . . . ? C42 C43 C44 C45 0.8(5) . . . . ? C43 C44 C45 C46 0.0(5) . . . . ? C42 C41 C46 C45 0.8(4) . . . . ? P1 C41 C46 C45 -172.1(3) . . . . ? C44 C45 C46 C41 -0.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.836 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.067 # Attachment '- fro5259.cif' data_fro5259 _database_code_depnum_ccdc_archive 'CCDC 816642' #TrackingRef '- fro5259.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Br P S' _chemical_formula_weight 503.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9519(1) _cell_length_b 17.2205(3) _cell_length_c 16.6525(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.739(1) _cell_angle_gamma 90.00 _cell_volume 2275.47(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4476 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5043 _exptl_absorpt_correction_T_max 0.7552 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13470 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 27.88 _reflns_number_total 5306 _reflns_number_gt 4090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+4.7598P] 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 5306 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Br1 Br 0.24244(5) 0.52541(3) 0.89124(3) 0.06059(15) Uani 1 1 d . . . P1 P -0.15792(10) 0.52504(5) 0.71098(5) 0.03120(18) Uani 1 1 d . . . S1 S 0.05359(11) 0.47770(6) 0.68234(6) 0.0480(2) Uani 1 1 d . . . C11 C -0.2438(4) 0.7467(2) 0.8489(2) 0.0424(8) Uani 1 1 d . . . H11 H -0.2877 0.7940 0.8666 0.051 Uiso 1 1 calc R . . C12 C -0.1348(5) 0.7463(2) 0.7868(2) 0.0443(8) Uani 1 1 d . . . H12 H -0.1032 0.7938 0.7643 0.053 Uiso 1 1 calc R . . C13 C -0.0718(4) 0.6781(2) 0.7574(2) 0.0382(7) Uani 1 1 d . . . C14 C -0.1551(4) 0.60883(18) 0.77745(18) 0.0314(6) Uani 1 1 d . . . C15 C -0.2579(4) 0.60984(19) 0.84221(18) 0.0331(7) Uani 1 1 d . . . H15 H -0.3086 0.5634 0.8579 0.040 Uiso 1 1 calc R . . C16 C -0.2875(4) 0.6782(2) 0.88440(19) 0.0363(7) Uani 1 1 d . . . C17 C -0.3361(5) 0.6768(2) 0.9711(2) 0.0490(9) Uani 1 1 d . . . H17A H -0.3678 0.6237 0.9852 0.059 Uiso 1 1 calc R . . H17B H -0.4345 0.7102 0.9763 0.059 Uiso 1 1 calc R . . C18 C -0.1883(5) 0.7051(3) 1.0315(2) 0.0608(12) Uani 1 1 d . . . H18A H -0.2110 0.7584 1.0485 0.073 Uiso 1 1 calc R . . H18B H -0.1834 0.6720 1.0795 0.073 Uiso 1 1 calc R . . C21 C 0.1595(4) 0.6259(2) 0.9150(2) 0.0432(8) Uani 1 1 d . . . C22 C 0.0476(4) 0.6306(2) 0.9752(2) 0.0425(8) Uani 1 1 d . . . H22 H 0.0180 0.5857 1.0031 0.051 Uiso 1 1 calc R . . C23 C -0.0208(5) 0.7025(2) 0.9942(2) 0.0505(9) Uani 1 1 d . . . C24 C 0.0539(6) 0.7676(3) 0.9636(3) 0.0635(12) Uani 1 1 d . . . H24 H 0.0318 0.8169 0.9849 0.076 Uiso 1 1 calc R . . C25 C 0.1615(5) 0.7609(3) 0.9015(3) 0.0666(13) Uani 1 1 d . . . H25 H 0.2083 0.8061 0.8805 0.080 Uiso 1 1 calc R . . C26 C 0.2020(4) 0.6894(3) 0.8696(3) 0.0547(10) Uani 1 1 d . . . C27 C 0.2492(5) 0.6810(3) 0.7831(3) 0.0703(14) Uani 1 1 d . . . H27A H 0.3115 0.6324 0.7780 0.084 Uiso 1 1 calc R . . H27B H 0.3249 0.7237 0.7709 0.084 Uiso 1 1 calc R . . C28 C 0.0963(5) 0.6813(2) 0.7199(2) 0.0529(10) Uani 1 1 d . . . H28A H 0.1007 0.7283 0.6871 0.064 Uiso 1 1 calc R . . H28B H 0.1053 0.6365 0.6841 0.064 Uiso 1 1 calc R . . C31 C -0.2904(4) 0.45415(17) 0.75718(18) 0.0312(6) Uani 1 1 d . . . C32 C -0.2180(4) 0.4060(2) 0.8172(2) 0.0399(8) Uani 1 1 d . . . H32 H -0.1026 0.4107 0.8326 0.048 Uiso 1 1 calc R . . C33 C -0.3142(5) 0.3514(2) 0.8541(2) 0.0436(8) Uani 1 1 d . . . H33 H -0.2646 0.3197 0.8951 0.052 Uiso 1 1 calc R . . C34 C -0.4829(5) 0.3435(2) 0.8309(2) 0.0415(8) Uani 1 1 d . . . H34 H -0.5479 0.3056 0.8553 0.050 Uiso 1 1 calc R . . C35 C -0.5561(4) 0.3910(2) 0.7722(2) 0.0419(8) Uani 1 1 d . . . H35 H -0.6712 0.3855 0.7564 0.050 Uiso 1 1 calc R . . C36 C -0.4615(4) 0.44688(19) 0.7361(2) 0.0360(7) Uani 1 1 d . . . H36 H -0.5132 0.4801 0.6971 0.043 Uiso 1 1 calc R . . C41 C -0.2815(4) 0.56220(18) 0.62356(18) 0.0326(6) Uani 1 1 d . . . C42 C -0.2410(4) 0.5408(2) 0.5468(2) 0.0388(7) Uani 1 1 d . . . H42 H -0.1480 0.5082 0.5401 0.047 Uiso 1 1 calc R . . C43 C -0.3375(5) 0.5673(2) 0.4795(2) 0.0440(8) Uani 1 1 d . . . H43 H -0.3090 0.5531 0.4276 0.053 Uiso 1 1 calc R . . C44 C -0.4746(5) 0.6143(2) 0.4890(2) 0.0457(8) Uani 1 1 d . . . H44 H -0.5404 0.6315 0.4435 0.055 Uiso 1 1 calc R . . C45 C -0.5162(4) 0.6364(2) 0.5649(2) 0.0417(8) Uani 1 1 d . . . H45 H -0.6100 0.6686 0.5711 0.050 Uiso 1 1 calc R . . C46 C -0.4191(4) 0.61110(19) 0.6320(2) 0.0372(7) Uani 1 1 d . . . H46 H -0.4462 0.6270 0.6836 0.045 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 Br1 0.0582(3) 0.0594(3) 0.0641(3) -0.0081(2) 0.00303(19) 0.0163(2) P1 0.0295(4) 0.0335(4) 0.0304(4) -0.0031(3) 0.0005(3) 0.0039(3) S1 0.0365(4) 0.0551(6) 0.0529(5) -0.0052(5) 0.0070(4) 0.0139(4) C11 0.0459(19) 0.0362(17) 0.044(2) -0.0053(15) -0.0063(15) 0.0105(15) C12 0.055(2) 0.0350(18) 0.042(2) 0.0031(15) -0.0026(16) 0.0015(15) C13 0.0421(18) 0.0386(17) 0.0339(17) -0.0006(14) 0.0016(13) -0.0033(14) C14 0.0299(15) 0.0326(15) 0.0313(16) -0.0026(13) -0.0018(12) -0.0003(12) C15 0.0293(15) 0.0378(17) 0.0316(16) -0.0043(13) -0.0020(12) -0.0002(12) C16 0.0332(16) 0.0412(18) 0.0341(17) -0.0071(14) -0.0013(13) 0.0060(13) C17 0.054(2) 0.053(2) 0.041(2) -0.0088(17) 0.0100(16) 0.0087(18) C18 0.068(3) 0.076(3) 0.037(2) -0.015(2) -0.0024(18) 0.026(2) C21 0.0354(17) 0.047(2) 0.046(2) -0.0017(16) -0.0103(14) 0.0061(15) C22 0.0453(19) 0.048(2) 0.0330(17) 0.0017(15) -0.0087(14) 0.0059(16) C23 0.056(2) 0.055(2) 0.0377(19) -0.0108(17) -0.0167(16) 0.0140(18) C24 0.057(2) 0.050(2) 0.079(3) -0.019(2) -0.032(2) 0.007(2) C25 0.046(2) 0.050(2) 0.101(4) 0.011(3) -0.018(2) -0.0086(19) C26 0.0288(17) 0.066(3) 0.068(3) 0.013(2) -0.0070(16) -0.0046(17) C27 0.043(2) 0.092(4) 0.077(3) 0.034(3) 0.014(2) 0.004(2) C28 0.054(2) 0.050(2) 0.057(2) -0.0048(19) 0.0188(18) -0.0133(18) C31 0.0357(16) 0.0284(15) 0.0290(15) -0.0038(12) -0.0012(12) 0.0036(12) C32 0.0373(17) 0.0400(18) 0.0410(19) 0.0032(15) -0.0083(14) 0.0012(14) C33 0.055(2) 0.0387(18) 0.0360(18) 0.0071(15) -0.0030(15) 0.0030(16) C34 0.050(2) 0.0346(17) 0.0408(19) -0.0013(14) 0.0097(15) 0.0004(15) C35 0.0353(17) 0.0381(18) 0.051(2) -0.0013(16) -0.0043(15) -0.0021(14) C36 0.0380(17) 0.0322(16) 0.0368(17) 0.0034(14) -0.0063(13) 0.0014(13) C41 0.0367(16) 0.0317(15) 0.0293(15) -0.0008(12) 0.0027(12) -0.0005(12) C42 0.0378(17) 0.0439(19) 0.0353(17) -0.0045(15) 0.0069(13) -0.0048(14) C43 0.051(2) 0.052(2) 0.0290(17) 0.0013(15) 0.0020(14) -0.0071(17) C44 0.050(2) 0.048(2) 0.0368(19) 0.0092(16) -0.0093(15) -0.0096(17) C45 0.0417(18) 0.0390(18) 0.0436(19) 0.0067(15) -0.0030(14) 0.0010(14) C46 0.0396(17) 0.0387(17) 0.0336(17) -0.0007(14) 0.0030(13) 0.0045(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C21 1.903(4) . ? P1 C31 1.816(3) . ? P1 C14 1.818(3) . ? P1 C41 1.819(3) . ? P1 S1 1.9559(11) . ? C11 C16 1.375(5) . ? C11 C12 1.392(5) . ? C11 H11 0.9400 . ? C12 C13 1.378(5) . ? C12 H12 0.9400 . ? C13 C14 1.415(4) . ? C13 C28 1.513(5) . ? C14 C15 1.395(4) . ? C15 C16 1.399(4) . ? C15 H15 0.9400 . ? C16 C17 1.519(5) . ? C17 C18 1.574(6) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C23 1.507(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C21 C26 1.384(5) . ? C21 C22 1.385(5) . ? C22 C23 1.397(5) . ? C22 H22 0.9400 . ? C23 C24 1.382(6) . ? C24 C25 1.389(7) . ? C24 H24 0.9400 . ? C25 C26 1.388(6) . ? C25 H25 0.9400 . ? C26 C27 1.518(6) . ? C27 C28 1.555(6) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C31 C36 1.388(4) . ? C31 C32 1.394(4) . ? C32 C33 1.382(5) . ? C32 H32 0.9400 . ? C33 C34 1.378(5) . ? C33 H33 0.9400 . ? C34 C35 1.376(5) . ? C34 H34 0.9400 . ? C35 C36 1.383(5) . ? C35 H35 0.9400 . ? C36 H36 0.9400 . ? C41 C42 1.389(4) . ? C41 C46 1.395(4) . ? C42 C43 1.393(5) . ? C42 H42 0.9400 . ? C43 C44 1.375(5) . ? C43 H43 0.9400 . ? C44 C45 1.381(5) . ? C44 H44 0.9400 . ? C45 C46 1.387(5) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C14 105.07(14) . . ? C31 P1 C41 106.11(14) . . ? C14 P1 C41 101.11(14) . . ? C31 P1 S1 110.79(11) . . ? C14 P1 S1 120.17(11) . . ? C41 P1 S1 112.32(11) . . ? C16 C11 C12 120.1(3) . . ? C16 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 121.8(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 116.6(3) . . ? C12 C13 C28 117.9(3) . . ? C14 C13 C28 124.5(3) . . ? C15 C14 C13 118.6(3) . . ? C15 C14 P1 119.7(2) . . ? C13 C14 P1 120.9(2) . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 116.8(3) . . ? C11 C16 C17 120.6(3) . . ? C15 C16 C17 121.7(3) . . ? C16 C17 C18 112.2(3) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C23 C18 C17 111.7(3) . . ? C23 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C23 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C26 C21 C22 122.8(4) . . ? C26 C21 Br1 120.2(3) . . ? C22 C21 Br1 116.9(3) . . ? C21 C22 C23 119.6(4) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 116.9(4) . . ? C24 C23 C18 122.8(4) . . ? C22 C23 C18 119.1(4) . . ? C23 C24 C25 120.5(4) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 121.9(4) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C21 C26 C25 114.8(4) . . ? C21 C26 C27 121.9(4) . . ? C25 C26 C27 121.7(4) . . ? C26 C27 C28 114.3(3) . . ? C26 C27 H27A 108.7 . . ? C28 C27 H27A 108.7 . . ? C26 C27 H27B 108.7 . . ? C28 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? C13 C28 C27 113.2(3) . . ? C13 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? C13 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.8 . . ? C36 C31 C32 118.7(3) . . ? C36 C31 P1 122.7(2) . . ? C32 C31 P1 118.7(2) . . ? C33 C32 C31 120.6(3) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C35 C34 C33 120.0(3) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C31 120.3(3) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? C42 C41 C46 119.0(3) . . ? C42 C41 P1 119.9(2) . . ? C46 C41 P1 121.2(2) . . ? C41 C42 C43 120.3(3) . . ? C41 C42 H42 119.9 . . ? C43 C42 H42 119.9 . . ? C44 C43 C42 120.0(3) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 120.5(3) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C44 C45 C46 119.8(3) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C45 C46 C41 120.5(3) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? 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 C16 C11 C12 C13 2.0(5) . . . . ? C11 C12 C13 C14 16.1(5) . . . . ? C11 C12 C13 C28 -153.1(4) . . . . ? C12 C13 C14 C15 -18.6(5) . . . . ? C28 C13 C14 C15 149.8(3) . . . . ? C12 C13 C14 P1 151.1(3) . . . . ? C28 C13 C14 P1 -40.5(5) . . . . ? C31 P1 C14 C15 -6.3(3) . . . . ? C41 P1 C14 C15 104.0(3) . . . . ? S1 P1 C14 C15 -131.9(2) . . . . ? C31 P1 C14 C13 -175.8(3) . . . . ? C41 P1 C14 C13 -65.6(3) . . . . ? S1 P1 C14 C13 58.6(3) . . . . ? C13 C14 C15 C16 3.6(5) . . . . ? P1 C14 C15 C16 -166.2(2) . . . . ? C12 C11 C16 C15 -17.2(5) . . . . ? C12 C11 C16 C17 152.4(3) . . . . ? C14 C15 C16 C11 14.4(5) . . . . ? C14 C15 C16 C17 -155.1(3) . . . . ? C11 C16 C17 C18 -61.3(4) . . . . ? C15 C16 C17 C18 107.8(4) . . . . ? C16 C17 C18 C23 -18.1(5) . . . . ? C26 C21 C22 C23 -3.0(5) . . . . ? Br1 C21 C22 C23 -178.5(3) . . . . ? C21 C22 C23 C24 -13.3(5) . . . . ? C21 C22 C23 C18 154.6(3) . . . . ? C17 C18 C23 C24 100.0(5) . . . . ? C17 C18 C23 C22 -67.2(5) . . . . ? C22 C23 C24 C25 15.6(5) . . . . ? C18 C23 C24 C25 -151.8(4) . . . . ? C23 C24 C25 C26 -1.9(6) . . . . ? C22 C21 C26 C25 16.3(5) . . . . ? Br1 C21 C26 C25 -168.3(3) . . . . ? C22 C21 C26 C27 -149.6(4) . . . . ? Br1 C21 C26 C27 25.8(5) . . . . ? C24 C25 C26 C21 -13.9(6) . . . . ? C24 C25 C26 C27 152.1(4) . . . . ? C21 C26 C27 C28 86.1(5) . . . . ? C25 C26 C27 C28 -78.9(5) . . . . ? C12 C13 C28 C27 80.3(5) . . . . ? C14 C13 C28 C27 -87.9(4) . . . . ? C26 C27 C28 C13 -8.3(6) . . . . ? C14 P1 C31 C36 94.1(3) . . . . ? C41 P1 C31 C36 -12.5(3) . . . . ? S1 P1 C31 C36 -134.7(2) . . . . ? C14 P1 C31 C32 -84.8(3) . . . . ? C41 P1 C31 C32 168.6(3) . . . . ? S1 P1 C31 C32 46.4(3) . . . . ? C36 C31 C32 C33 0.8(5) . . . . ? P1 C31 C32 C33 179.8(3) . . . . ? C31 C32 C33 C34 0.9(5) . . . . ? C32 C33 C34 C35 -1.3(5) . . . . ? C33 C34 C35 C36 0.0(5) . . . . ? C34 C35 C36 C31 1.8(5) . . . . ? C32 C31 C36 C35 -2.2(5) . . . . ? P1 C31 C36 C35 178.9(3) . . . . ? C31 P1 C41 C42 -107.4(3) . . . . ? C14 P1 C41 C42 143.2(3) . . . . ? S1 P1 C41 C42 13.8(3) . . . . ? C31 P1 C41 C46 71.5(3) . . . . ? C14 P1 C41 C46 -38.0(3) . . . . ? S1 P1 C41 C46 -167.3(2) . . . . ? C46 C41 C42 C43 -0.5(5) . . . . ? P1 C41 C42 C43 178.3(3) . . . . ? C41 C42 C43 C44 -0.6(5) . . . . ? C42 C43 C44 C45 0.9(5) . . . . ? C43 C44 C45 C46 0.0(5) . . . . ? C44 C45 C46 C41 -1.2(5) . . . . ? C42 C41 C46 C45 1.5(5) . . . . ? P1 C41 C46 C45 -177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.669 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.065 data_fro4902 _database_code_depnum_ccdc_archive 'CCDC 816643' #TrackingRef '- fro4902.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Br O P' _chemical_formula_weight 487.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 8.7032(2) _cell_length_b 10.9880(2) _cell_length_c 11.9218(3) _cell_angle_alpha 82.583(1) _cell_angle_beta 76.308(1) _cell_angle_gamma 78.288(2) _cell_volume 1080.69(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 987 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 3.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4812 _exptl_absorpt_correction_T_max 0.8473 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12873 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 68.09 _reflns_number_total 3751 _reflns_number_gt 3402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0833P)^2^+1.1052P] 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 3751 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Br1 Br 0.36704(4) 0.74444(4) 0.51694(3) 0.04867(18) Uani 1 1 d . . . P1 P 0.27558(9) 0.76804(7) 0.86340(6) 0.0262(2) Uani 1 1 d . . . O1 O 0.4175(3) 0.6900(2) 0.79700(18) 0.0342(5) Uani 1 1 d . . . C11 C -0.2258(4) 0.7324(3) 0.8357(3) 0.0379(7) Uani 1 1 d . . . H11 H -0.3345 0.7266 0.8450 0.045 Uiso 1 1 calc R . . C12 C -0.1170(4) 0.6296(3) 0.8610(3) 0.0378(7) Uani 1 1 d . . . H12 H -0.1529 0.5540 0.8888 0.045 Uiso 1 1 calc R . . C13 C 0.0444(4) 0.6341(3) 0.8466(2) 0.0316(6) Uani 1 1 d . . . C14 C 0.0847(4) 0.7533(3) 0.8375(2) 0.0277(6) Uani 1 1 d . . . C15 C -0.0262(4) 0.8560(3) 0.8118(2) 0.0296(6) Uani 1 1 d . . . H15 H 0.0003 0.9359 0.8045 0.036 Uiso 1 1 calc R . . C16 C -0.1754(4) 0.8447(3) 0.7963(3) 0.0334(7) Uani 1 1 d . . . C17 C -0.2633(4) 0.9408(3) 0.7208(3) 0.0422(8) Uani 1 1 d . . . H17A H -0.2126 1.0149 0.7047 0.051 Uiso 1 1 calc R . . H17B H -0.3746 0.9657 0.7625 0.051 Uiso 1 1 calc R . . C18 C -0.2633(5) 0.8914(4) 0.6031(3) 0.0454(8) Uani 1 1 d . . . H18A H -0.3647 0.8626 0.6095 0.054 Uiso 1 1 calc R . . H18B H -0.2561 0.9597 0.5416 0.054 Uiso 1 1 calc R . . C21 C 0.1535(4) 0.7110(3) 0.5603(3) 0.0349(7) Uani 1 1 d . . . C22 C 0.0317(4) 0.8055(3) 0.5411(3) 0.0370(7) Uani 1 1 d . . . H22 H 0.0549 0.8837 0.5074 0.044 Uiso 1 1 calc R . . C23 C -0.1264(4) 0.7868(3) 0.5711(3) 0.0383(7) Uani 1 1 d . . . C24 C -0.1500(5) 0.6648(4) 0.5945(3) 0.0439(8) Uani 1 1 d . . . H24 H -0.2508 0.6453 0.5962 0.053 Uiso 1 1 calc R . . C25 C -0.0256(5) 0.5722(3) 0.6153(3) 0.0453(8) Uani 1 1 d . . . H25 H -0.0437 0.4896 0.6317 0.054 Uiso 1 1 calc R . . C26 C 0.1255(5) 0.5958(3) 0.6130(3) 0.0391(7) Uani 1 1 d . . . C27 C 0.2336(5) 0.5125(4) 0.6843(3) 0.0505(9) Uani 1 1 d . . . H27A H 0.3393 0.5375 0.6643 0.061 Uiso 1 1 calc R . . H27B H 0.2483 0.4263 0.6648 0.061 Uiso 1 1 calc R . . C28 C 0.1645(4) 0.5179(3) 0.8184(3) 0.0401(7) Uani 1 1 d . . . H28A H 0.1134 0.4451 0.8486 0.048 Uiso 1 1 calc R . . H28B H 0.2533 0.5137 0.8571 0.048 Uiso 1 1 calc R . . C31 C 0.2552(4) 0.7298(3) 1.0174(3) 0.0294(6) Uani 1 1 d . . . C32 C 0.3799(4) 0.6494(3) 1.0546(3) 0.0340(7) Uani 1 1 d . . . H32 H 0.4710 0.6154 1.0006 0.041 Uiso 1 1 calc R . . C33 C 0.3705(5) 0.6186(3) 1.1725(3) 0.0435(8) Uani 1 1 d . . . H33 H 0.4542 0.5620 1.1981 0.052 Uiso 1 1 calc R . . C34 C 0.2412(5) 0.6700(4) 1.2507(3) 0.0438(8) Uani 1 1 d . . . H34 H 0.2375 0.6511 1.3304 0.053 Uiso 1 1 calc R . . C35 C 0.1152(5) 0.7497(4) 1.2143(3) 0.0438(8) Uani 1 1 d . . . H35 H 0.0252 0.7843 1.2688 0.053 Uiso 1 1 calc R . . C36 C 0.1216(4) 0.7784(3) 1.0982(3) 0.0378(7) Uani 1 1 d . . . H36 H 0.0346 0.8315 1.0733 0.045 Uiso 1 1 calc R . . C41 C 0.2910(3) 0.9307(3) 0.8390(3) 0.0281(6) Uani 1 1 d . . . C42 C 0.3131(4) 0.9960(3) 0.9242(3) 0.0355(7) Uani 1 1 d . . . H42 H 0.3068 0.9588 1.0003 0.043 Uiso 1 1 calc R . . C43 C 0.3447(5) 1.1159(3) 0.8971(3) 0.0420(8) Uani 1 1 d . . . H43 H 0.3617 1.1594 0.9547 0.050 Uiso 1 1 calc R . . C44 C 0.3513(4) 1.1717(3) 0.7876(3) 0.0401(7) Uani 1 1 d . . . H44 H 0.3724 1.2534 0.7701 0.048 Uiso 1 1 calc R . . C45 C 0.3268(4) 1.1084(3) 0.7025(3) 0.0393(7) Uani 1 1 d . . . H45 H 0.3297 1.1473 0.6272 0.047 Uiso 1 1 calc R . . C46 C 0.2985(4) 0.9887(3) 0.7279(3) 0.0340(7) Uani 1 1 d . . . H46 H 0.2840 0.9453 0.6693 0.041 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 Br1 0.0433(3) 0.0631(3) 0.0398(3) -0.00953(18) -0.00433(16) -0.01202(18) P1 0.0256(4) 0.0302(4) 0.0243(4) -0.0017(3) -0.0082(3) -0.0056(3) O1 0.0290(11) 0.0393(12) 0.0340(11) -0.0077(9) -0.0061(9) -0.0034(9) C11 0.0273(15) 0.062(2) 0.0283(15) -0.0086(14) -0.0033(12) -0.0164(14) C12 0.0432(18) 0.0496(19) 0.0259(15) 0.0022(13) -0.0073(13) -0.0241(15) C13 0.0376(17) 0.0381(16) 0.0227(14) 0.0028(12) -0.0102(12) -0.0141(13) C14 0.0287(15) 0.0360(15) 0.0210(13) -0.0047(11) -0.0068(11) -0.0087(12) C15 0.0289(15) 0.0350(15) 0.0257(14) -0.0078(11) -0.0049(11) -0.0055(12) C16 0.0258(15) 0.0473(18) 0.0278(15) -0.0118(13) -0.0056(12) -0.0032(13) C17 0.0318(17) 0.0481(19) 0.0473(19) -0.0096(15) -0.0138(14) 0.0006(14) C18 0.045(2) 0.054(2) 0.0396(18) 0.0008(15) -0.0196(15) -0.0030(16) C21 0.0418(18) 0.0408(17) 0.0221(14) -0.0064(12) -0.0041(12) -0.0081(14) C22 0.0484(19) 0.0393(17) 0.0233(14) 0.0003(12) -0.0077(13) -0.0098(14) C23 0.0470(19) 0.0482(19) 0.0220(14) -0.0017(13) -0.0131(13) -0.0078(15) C24 0.052(2) 0.054(2) 0.0328(17) -0.0095(15) -0.0127(15) -0.0190(17) C25 0.067(2) 0.0368(18) 0.0352(17) -0.0089(14) -0.0091(16) -0.0155(16) C26 0.053(2) 0.0332(16) 0.0298(16) -0.0090(13) -0.0069(14) -0.0021(14) C27 0.059(2) 0.0389(19) 0.047(2) -0.0017(16) -0.0108(18) 0.0046(17) C28 0.050(2) 0.0308(16) 0.0432(18) 0.0023(13) -0.0185(15) -0.0088(14) C31 0.0327(15) 0.0295(15) 0.0294(15) 0.0003(11) -0.0118(12) -0.0089(12) C32 0.0323(16) 0.0356(16) 0.0353(16) 0.0008(12) -0.0112(13) -0.0069(12) C33 0.046(2) 0.048(2) 0.0419(19) 0.0087(15) -0.0229(16) -0.0142(16) C34 0.059(2) 0.054(2) 0.0277(16) 0.0040(14) -0.0171(15) -0.0265(17) C35 0.048(2) 0.050(2) 0.0314(17) -0.0064(14) -0.0022(15) -0.0116(16) C36 0.0374(17) 0.0422(18) 0.0312(16) 0.0009(13) -0.0063(13) -0.0048(14) C41 0.0247(14) 0.0309(15) 0.0294(14) -0.0014(11) -0.0069(11) -0.0063(11) C42 0.0419(18) 0.0378(17) 0.0284(15) -0.0034(13) -0.0074(13) -0.0110(13) C43 0.050(2) 0.0411(18) 0.0374(18) -0.0121(14) -0.0047(15) -0.0127(15) C44 0.0445(19) 0.0267(15) 0.049(2) 0.0004(13) -0.0109(15) -0.0063(13) C45 0.0384(17) 0.0418(18) 0.0375(17) 0.0064(14) -0.0120(14) -0.0087(14) C46 0.0367(16) 0.0395(17) 0.0292(15) -0.0004(13) -0.0124(13) -0.0099(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C21 1.905(3) . ? P1 O1 1.473(2) . ? P1 C41 1.800(3) . ? P1 C14 1.802(3) . ? P1 C31 1.804(3) . ? C11 C12 1.370(5) . ? C11 C16 1.381(5) . ? C12 C13 1.385(5) . ? C13 C14 1.408(4) . ? C13 C28 1.496(5) . ? C14 C15 1.381(4) . ? C15 C16 1.385(4) . ? C16 C17 1.504(5) . ? C17 C18 1.568(5) . ? C18 C23 1.492(5) . ? C21 C22 1.364(5) . ? C21 C26 1.380(5) . ? C22 C23 1.388(5) . ? C23 C24 1.380(5) . ? C24 C25 1.373(6) . ? C25 C26 1.385(6) . ? C26 C27 1.508(5) . ? C27 C28 1.574(5) . ? C31 C32 1.376(4) . ? C31 C36 1.385(5) . ? C32 C33 1.389(5) . ? C33 C34 1.355(6) . ? C34 C35 1.377(6) . ? C35 C36 1.369(5) . ? C41 C46 1.386(4) . ? C41 C42 1.387(4) . ? C42 C43 1.383(5) . ? C43 C44 1.362(5) . ? C44 C45 1.380(5) . ? C45 C46 1.370(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 O1 P1 C41 111.50(13) . . ? O1 P1 C14 115.65(13) . . ? C41 P1 C14 107.74(14) . . ? O1 P1 C31 111.56(13) . . ? C41 P1 C31 105.65(14) . . ? C14 P1 C31 104.01(13) . . ? C12 C11 C16 119.8(3) . . ? C11 C12 C13 121.8(3) . . ? C12 C13 C14 116.6(3) . . ? C12 C13 C28 118.3(3) . . ? C14 C13 C28 123.9(3) . . ? C15 C14 C13 118.5(3) . . ? C15 C14 P1 122.0(2) . . ? C13 C14 P1 119.4(2) . . ? C14 C15 C16 121.9(3) . . ? C11 C16 C15 117.0(3) . . ? C11 C16 C17 121.2(3) . . ? C15 C16 C17 120.8(3) . . ? C16 C17 C18 112.4(3) . . ? C23 C18 C17 111.8(3) . . ? C22 C21 C26 122.1(3) . . ? C22 C21 Br1 117.8(3) . . ? C26 C21 Br1 120.1(3) . . ? C21 C22 C23 120.4(3) . . ? C24 C23 C22 116.7(3) . . ? C24 C23 C18 120.2(3) . . ? C22 C23 C18 121.7(3) . . ? C25 C24 C23 119.7(3) . . ? C24 C25 C26 122.5(3) . . ? C21 C26 C25 114.5(3) . . ? C21 C26 C27 123.4(3) . . ? C25 C26 C27 120.9(3) . . ? C26 C27 C28 112.7(3) . . ? C13 C28 C27 112.4(3) . . ? C32 C31 C36 119.3(3) . . ? C32 C31 P1 117.7(2) . . ? C36 C31 P1 123.0(2) . . ? C31 C32 C33 119.7(3) . . ? C34 C33 C32 120.3(3) . . ? C33 C34 C35 120.4(3) . . ? C36 C35 C34 119.8(3) . . ? C35 C36 C31 120.4(3) . . ? C46 C41 C42 118.8(3) . . ? C46 C41 P1 118.7(2) . . ? C42 C41 P1 122.1(2) . . ? C43 C42 C41 119.9(3) . . ? C44 C43 C42 120.6(3) . . ? C43 C44 C45 120.0(3) . . ? C46 C45 C44 119.9(3) . . ? C45 C46 C41 120.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 -1.0(5) . . . . ? C11 C12 C13 C14 17.7(4) . . . . ? C11 C12 C13 C28 -150.3(3) . . . . ? C12 C13 C14 C15 -17.3(4) . . . . ? C28 C13 C14 C15 149.9(3) . . . . ? C12 C13 C14 P1 161.0(2) . . . . ? C28 C13 C14 P1 -31.8(4) . . . . ? O1 P1 C14 C15 -129.5(2) . . . . ? C41 P1 C14 C15 -4.0(3) . . . . ? C31 P1 C14 C15 107.8(3) . . . . ? O1 P1 C14 C13 52.3(3) . . . . ? C41 P1 C14 C13 177.8(2) . . . . ? C31 P1 C14 C13 -70.4(3) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? P1 C14 C15 C16 -177.4(2) . . . . ? C12 C11 C16 C15 -15.8(4) . . . . ? C12 C11 C16 C17 153.0(3) . . . . ? C14 C15 C16 C11 15.9(4) . . . . ? C14 C15 C16 C17 -152.9(3) . . . . ? C11 C16 C17 C18 -61.2(4) . . . . ? C15 C16 C17 C18 107.2(4) . . . . ? C16 C17 C18 C23 -23.5(4) . . . . ? C26 C21 C22 C23 -2.2(5) . . . . ? Br1 C21 C22 C23 -179.9(2) . . . . ? C21 C22 C23 C24 -14.6(5) . . . . ? C21 C22 C23 C18 151.7(3) . . . . ? C17 C18 C23 C24 98.2(4) . . . . ? C17 C18 C23 C22 -67.6(4) . . . . ? C22 C23 C24 C25 15.8(5) . . . . ? C18 C23 C24 C25 -150.7(3) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C22 C21 C26 C25 17.1(4) . . . . ? Br1 C21 C26 C25 -165.3(2) . . . . ? C22 C21 C26 C27 -150.7(3) . . . . ? Br1 C21 C26 C27 26.9(4) . . . . ? C24 C25 C26 C21 -15.8(5) . . . . ? C24 C25 C26 C27 152.3(3) . . . . ? C21 C26 C27 C28 101.3(4) . . . . ? C25 C26 C27 C28 -65.7(4) . . . . ? C12 C13 C28 C27 94.7(4) . . . . ? C14 C13 C28 C27 -72.3(4) . . . . ? C26 C27 C28 C13 -21.2(5) . . . . ? O1 P1 C31 C32 8.8(3) . . . . ? C41 P1 C31 C32 -112.5(2) . . . . ? C14 P1 C31 C32 134.2(2) . . . . ? O1 P1 C31 C36 -171.8(3) . . . . ? C41 P1 C31 C36 66.9(3) . . . . ? C14 P1 C31 C36 -46.5(3) . . . . ? C36 C31 C32 C33 -0.3(5) . . . . ? P1 C31 C32 C33 179.1(3) . . . . ? C31 C32 C33 C34 -1.7(5) . . . . ? C32 C33 C34 C35 2.3(5) . . . . ? C33 C34 C35 C36 -0.8(6) . . . . ? C34 C35 C36 C31 -1.3(6) . . . . ? C32 C31 C36 C35 1.8(5) . . . . ? P1 C31 C36 C35 -177.5(3) . . . . ? O1 P1 C41 C46 62.4(3) . . . . ? C14 P1 C41 C46 -65.5(3) . . . . ? C31 P1 C41 C46 -176.3(2) . . . . ? O1 P1 C41 C42 -110.4(3) . . . . ? C14 P1 C41 C42 121.7(3) . . . . ? C31 P1 C41 C42 11.0(3) . . . . ? C46 C41 C42 C43 -1.0(5) . . . . ? P1 C41 C42 C43 171.8(3) . . . . ? C41 C42 C43 C44 1.2(5) . . . . ? C42 C43 C44 C45 -0.2(6) . . . . ? C43 C44 C45 C46 -1.0(5) . . . . ? C44 C45 C46 C41 1.2(5) . . . . ? C42 C41 C46 C45 -0.2(5) . . . . ? P1 C41 C46 C45 -173.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 68.09 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.676 _refine_diff_density_min -0.945 _refine_diff_density_rms 0.106