Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Petr Kilian' _publ_contact_author_address ; School of Chemistry University of St Andrews St Andrews KY16 9ST UNITED KINGDOM ; _publ_contact_author_email PK7@ST-AND.AC.UK _publ_section_title ; 1,8,9-Substituted Anthracenes, Intramolecular Phosphine Donor Stabilized Metaphosphonate and Phosphenium ; loop_ _publ_author_name 'Petr Kilian' 'A. Slawin' # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 635696' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H47 N2 P3' _chemical_formula_sum 'C30 H47 N2 P3' _chemical_formula_weight 528.61 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.7477(9) _cell_length_b 16.8248(9) _cell_length_c 43.026(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 12123.8(11) _cell_formula_units_Z 16 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 18007 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 26.37 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4576 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9549 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 80212 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.35 _reflns_number_total 10934 _reflns_number_gt 9084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+43.7765P] 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 10934 _refine_ls_number_parameters 640 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.1742 _refine_ls_wR_factor_gt 0.1643 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8659(2) 0.0840(3) 0.71059(9) 0.0187(9) Uani 1 1 d . . . C2 C 0.9183(3) 0.1193(3) 0.73077(10) 0.0260(10) Uani 1 1 d . . . H2A H 0.9453 0.0870 0.7455 0.031 Uiso 1 1 calc R . . C3 C 0.9339(3) 0.2021(3) 0.73048(10) 0.0283(11) Uani 1 1 d . . . H3A H 0.9669 0.2251 0.7460 0.034 Uiso 1 1 calc R . . C4 C 0.9017(3) 0.2482(3) 0.70809(11) 0.0287(10) Uani 1 1 d . . . H4A H 0.9153 0.3030 0.7071 0.034 Uiso 1 1 calc R . . C5 C 0.8479(2) 0.2157(3) 0.68606(10) 0.0229(9) Uani 1 1 d . . . C6 C 0.8149(3) 0.2642(3) 0.66322(11) 0.0272(10) Uani 1 1 d . . . H6A H 0.8268 0.3194 0.6632 0.033 Uiso 1 1 calc R . . C7 C 0.7645(3) 0.2334(2) 0.64028(11) 0.0238(10) Uani 1 1 d . . . C8 C 0.7321(3) 0.2846(3) 0.61684(12) 0.0326(11) Uani 1 1 d . . . H8A H 0.7466 0.3392 0.6165 0.039 Uiso 1 1 calc R . . C9 C 0.6810(3) 0.2559(3) 0.59518(11) 0.0347(12) Uani 1 1 d . . . H9A H 0.6562 0.2912 0.5809 0.042 Uiso 1 1 calc R . . C10 C 0.6646(3) 0.1737(3) 0.59382(11) 0.0288(10) Uani 1 1 d . . . H10A H 0.6326 0.1540 0.5773 0.035 Uiso 1 1 calc R . . C11 C 0.6931(3) 0.1213(2) 0.61548(9) 0.0202(9) Uani 1 1 d . . . C12 C 0.7390(2) 0.1512(2) 0.64172(9) 0.0169(8) Uani 1 1 d . . . C13 C 0.7589(2) 0.1063(2) 0.66906(9) 0.0141(8) Uani 1 1 d . . . C14 C 0.8233(2) 0.1337(2) 0.68825(9) 0.0161(8) Uani 1 1 d . . . P1 P 0.86099(7) -0.02529(7) 0.70667(3) 0.0232(3) Uani 1 1 d . . . C15 C 0.9064(3) -0.0587(3) 0.74435(11) 0.0319(11) Uani 1 1 d . . . H15A H 0.9595 -0.0323 0.7468 0.038 Uiso 1 1 calc R . . C16 C 0.8534(3) -0.0359(3) 0.77210(11) 0.0347(12) Uani 1 1 d . . . H16A H 0.8789 -0.0535 0.7914 0.052 Uiso 1 1 calc R . . H16B H 0.8012 -0.0616 0.7700 0.052 Uiso 1 1 calc R . . H16C H 0.8464 0.0219 0.7726 0.052 Uiso 1 1 calc R . . C17 C 0.9185(4) -0.1475(3) 0.74405(13) 0.0516(16) Uani 1 1 d . . . H17A H 0.9424 -0.1643 0.7638 0.077 Uiso 1 1 calc R . . H17B H 0.9540 -0.1619 0.7269 0.077 Uiso 1 1 calc R . . H17C H 0.8668 -0.1740 0.7413 0.077 Uiso 1 1 calc R . . C18 C 0.9426(3) -0.0370(3) 0.67774(11) 0.0331(11) Uani 1 1 d . . . H18A H 0.9288 0.0003 0.6605 0.040 Uiso 1 1 calc R . . C19 C 1.0262(3) -0.0143(4) 0.68745(13) 0.0447(14) Uani 1 1 d . . . H19A H 1.0629 -0.0230 0.6701 0.067 Uiso 1 1 calc R . . H19B H 1.0426 -0.0470 0.7052 0.067 Uiso 1 1 calc R . . H19C H 1.0272 0.0419 0.6934 0.067 Uiso 1 1 calc R . . C20 C 0.9401(4) -0.1205(3) 0.66301(13) 0.0474(15) Uani 1 1 d . . . H20A H 0.9832 -0.1255 0.6477 0.071 Uiso 1 1 calc R . . H20B H 0.8885 -0.1284 0.6527 0.071 Uiso 1 1 calc R . . H20C H 0.9469 -0.1608 0.6793 0.071 Uiso 1 1 calc R . . P11 P 0.68851(6) 0.01240(6) 0.60868(2) 0.0187(2) Uani 1 1 d . . . C21 C 0.6039(3) 0.0016(3) 0.58080(11) 0.0309(11) Uani 1 1 d . . . H21A H 0.6129 0.0382 0.5628 0.037 Uiso 1 1 calc R . . C22 C 0.5247(3) 0.0220(3) 0.59595(13) 0.0387(12) Uani 1 1 d . . . H22A H 0.4816 0.0161 0.5807 0.058 Uiso 1 1 calc R . . H22B H 0.5261 0.0770 0.6034 0.058 Uiso 1 1 calc R . . H22C H 0.5151 -0.0139 0.6135 0.058 Uiso 1 1 calc R . . C23 C 0.6013(3) -0.0847(4) 0.56883(14) 0.0503(15) Uani 1 1 d . . . H23A H 0.5573 -0.0905 0.5540 0.076 Uiso 1 1 calc R . . H23B H 0.5932 -0.1209 0.5864 0.076 Uiso 1 1 calc R . . H23C H 0.6519 -0.0974 0.5585 0.076 Uiso 1 1 calc R . . C24 C 0.7758(3) 0.0008(3) 0.58164(10) 0.0240(10) Uani 1 1 d . . . H24A H 0.7727 -0.0545 0.5732 0.029 Uiso 1 1 calc R . . C25 C 0.8532(3) 0.0053(3) 0.60018(11) 0.0304(11) Uani 1 1 d . . . H25A H 0.8988 -0.0010 0.5861 0.046 Uiso 1 1 calc R . . H25B H 0.8540 -0.0372 0.6158 0.046 Uiso 1 1 calc R . . H25C H 0.8566 0.0570 0.6106 0.046 Uiso 1 1 calc R . . C26 C 0.7788(3) 0.0561(3) 0.55332(11) 0.0341(11) Uani 1 1 d . . . H26A H 0.8266 0.0443 0.5410 0.051 Uiso 1 1 calc R . . H26B H 0.7806 0.1115 0.5603 0.051 Uiso 1 1 calc R . . H26C H 0.7311 0.0478 0.5405 0.051 Uiso 1 1 calc R . . P13 P 0.68837(6) 0.02858(6) 0.68360(2) 0.0163(2) Uani 1 1 d . . . N1 N 0.6939(2) 0.0487(2) 0.72275(8) 0.0285(9) Uani 1 1 d . . . C27 C 0.6848(3) 0.1260(3) 0.73722(12) 0.0405(13) Uani 1 1 d . . . H27A H 0.6288 0.1339 0.7431 0.061 Uiso 1 1 calc R . . H27B H 0.7008 0.1676 0.7225 0.061 Uiso 1 1 calc R . . H27C H 0.7185 0.1289 0.7558 0.061 Uiso 1 1 calc R . . C28 C 0.6612(3) -0.0157(4) 0.74207(11) 0.0435(14) Uani 1 1 d . . . H28A H 0.6842 -0.0125 0.7630 0.065 Uiso 1 1 calc R . . H28B H 0.6748 -0.0671 0.7328 0.065 Uiso 1 1 calc R . . H28C H 0.6031 -0.0104 0.7433 0.065 Uiso 1 1 calc R . . N2 N 0.6000(2) 0.0710(2) 0.67117(9) 0.0225(8) Uani 1 1 d . . . C29 C 0.5762(3) 0.1534(3) 0.67579(12) 0.0315(11) Uani 1 1 d . . . H29A H 0.5386 0.1690 0.6595 0.047 Uiso 1 1 calc R . . H29B H 0.6235 0.1876 0.6749 0.047 Uiso 1 1 calc R . . H29C H 0.5505 0.1590 0.6961 0.047 Uiso 1 1 calc R . . C30 C 0.5315(3) 0.0181(3) 0.67573(12) 0.0322(11) Uani 1 1 d . . . H30A H 0.5142 0.0206 0.6975 0.048 Uiso 1 1 calc R . . H30B H 0.5469 -0.0365 0.6706 0.048 Uiso 1 1 calc R . . H30C H 0.4876 0.0348 0.6622 0.048 Uiso 1 1 calc R . . C31 C 1.1275(2) 0.2855(3) 0.52922(9) 0.0211(9) Uani 1 1 d . . . C32 C 1.0805(3) 0.3075(3) 0.50437(10) 0.0254(10) Uani 1 1 d . . . H32A H 1.0562 0.2674 0.4921 0.030 Uiso 1 1 calc R . . C33 C 1.0675(3) 0.3883(3) 0.49674(11) 0.0300(11) Uani 1 1 d . . . H33A H 1.0373 0.4015 0.4788 0.036 Uiso 1 1 calc R . . C34 C 1.0974(3) 0.4465(3) 0.51463(11) 0.0289(11) Uani 1 1 d . . . H34A H 1.0870 0.5004 0.5095 0.035 Uiso 1 1 calc R . . C35 C 1.1448(2) 0.4279(3) 0.54130(10) 0.0238(10) Uani 1 1 d . . . C36 C 1.1732(3) 0.4876(3) 0.56042(11) 0.0276(10) Uani 1 1 d . . . H36A H 1.1658 0.5414 0.5544 0.033 Uiso 1 1 calc R . . C37 C 1.2123(3) 0.4708(3) 0.58827(11) 0.0259(10) Uani 1 1 d . . . C38 C 1.2378(3) 0.5329(3) 0.60892(12) 0.0326(11) Uani 1 1 d . . . H38A H 1.2302 0.5869 0.6032 0.039 Uiso 1 1 calc R . . C39 C 1.2721(3) 0.5153(3) 0.63608(12) 0.0344(12) Uani 1 1 d . . . H39A H 1.2922 0.5569 0.6488 0.041 Uiso 1 1 calc R . . C40 C 1.2789(3) 0.4349(3) 0.64610(12) 0.0292(10) Uani 1 1 d . . . H40A H 1.2979 0.4240 0.6665 0.035 Uiso 1 1 calc R . . C41 C 1.2587(2) 0.3726(2) 0.62695(10) 0.0188(9) Uani 1 1 d . . . C42 C 1.2307(2) 0.3892(2) 0.59572(10) 0.0200(9) Uani 1 1 d . . . C43 C 1.2210(2) 0.3303(2) 0.57218(10) 0.0189(9) Uani 1 1 d . . . C44 C 1.1652(2) 0.3462(3) 0.54778(10) 0.0210(9) Uani 1 1 d . . . P31 P 1.13120(7) 0.18225(7) 0.54417(3) 0.0237(3) Uani 1 1 d . . . C45 C 1.0865(3) 0.1217(3) 0.51271(11) 0.0337(11) Uani 1 1 d . . . H45A H 1.0322 0.1426 0.5076 0.040 Uiso 1 1 calc R . . C46 C 1.1388(3) 0.1233(3) 0.48344(12) 0.0429(13) Uani 1 1 d . . . H46A H 1.1137 0.0911 0.4671 0.064 Uiso 1 1 calc R . . H46B H 1.1916 0.1015 0.4883 0.064 Uiso 1 1 calc R . . H46C H 1.1444 0.1782 0.4762 0.064 Uiso 1 1 calc R . . C47 C 1.0792(4) 0.0359(3) 0.52495(13) 0.0460(14) Uani 1 1 d . . . H47A H 1.0556 0.0022 0.5088 0.069 Uiso 1 1 calc R . . H47B H 1.0451 0.0353 0.5434 0.069 Uiso 1 1 calc R . . H47C H 1.1324 0.0157 0.5303 0.069 Uiso 1 1 calc R . . C48 C 1.0497(3) 0.1935(3) 0.57432(10) 0.0260(10) Uani 1 1 d . . . H48A H 1.0601 0.2451 0.5851 0.031 Uiso 1 1 calc R . . C49 C 0.9645(3) 0.1989(3) 0.56135(12) 0.0359(12) Uani 1 1 d . . . H49A H 0.9266 0.2050 0.5785 0.054 Uiso 1 1 calc R . . H49B H 0.9520 0.1504 0.5498 0.054 Uiso 1 1 calc R . . H49C H 0.9604 0.2449 0.5475 0.054 Uiso 1 1 calc R . . C50 C 1.0564(3) 0.1293(3) 0.59899(11) 0.0371(12) Uani 1 1 d . . . H50A H 1.0141 0.1364 0.6144 0.056 Uiso 1 1 calc R . . H50B H 1.1086 0.1331 0.6092 0.056 Uiso 1 1 calc R . . H50C H 1.0510 0.0769 0.5892 0.056 Uiso 1 1 calc R . . P41 P 1.24671(7) 0.27038(6) 0.64161(2) 0.0191(2) Uani 1 1 d . . . C51 C 1.3318(3) 0.2579(3) 0.67004(11) 0.0268(10) Uani 1 1 d . . . H51A H 1.3794 0.2837 0.6603 0.032 Uiso 1 1 calc R . . C52 C 1.3520(3) 0.1698(3) 0.67317(12) 0.0357(12) Uani 1 1 d . . . H52A H 1.3965 0.1633 0.6877 0.054 Uiso 1 1 calc R . . H52B H 1.3672 0.1485 0.6528 0.054 Uiso 1 1 calc R . . H52C H 1.3053 0.1410 0.6810 0.054 Uiso 1 1 calc R . . C53 C 1.3246(3) 0.2928(3) 0.70253(11) 0.0384(12) Uani 1 1 d . . . H53A H 1.3736 0.2819 0.7142 0.058 Uiso 1 1 calc R . . H53B H 1.2790 0.2687 0.7132 0.058 Uiso 1 1 calc R . . H53C H 1.3166 0.3504 0.7011 0.058 Uiso 1 1 calc R . . C54 C 1.1588(3) 0.2884(3) 0.66807(10) 0.0235(10) Uani 1 1 d . . . H54A H 1.1757 0.3252 0.6851 0.028 Uiso 1 1 calc R . . C55 C 1.0881(3) 0.3266(3) 0.65031(11) 0.0309(11) Uani 1 1 d . . . H55A H 1.0435 0.3353 0.6647 0.046 Uiso 1 1 calc R . . H55B H 1.0710 0.2911 0.6335 0.046 Uiso 1 1 calc R . . H55C H 1.1050 0.3776 0.6415 0.046 Uiso 1 1 calc R . . C56 C 1.1330(3) 0.2094(3) 0.68251(11) 0.0306(11) Uani 1 1 d . . . H56A H 1.0873 0.2184 0.6963 0.046 Uiso 1 1 calc R . . H56B H 1.1774 0.1870 0.6945 0.046 Uiso 1 1 calc R . . H56C H 1.1176 0.1723 0.6660 0.046 Uiso 1 1 calc R . . P43 P 1.29473(6) 0.24660(6) 0.56848(2) 0.0187(2) Uani 1 1 d . . . N3 N 1.3121(2) 0.2567(2) 0.52962(8) 0.0257(8) Uani 1 1 d . . . C57 C 1.3252(3) 0.3295(3) 0.51248(11) 0.0306(11) Uani 1 1 d . . . H57A H 1.3822 0.3351 0.5079 0.046 Uiso 1 1 calc R . . H57B H 1.3073 0.3748 0.5250 0.046 Uiso 1 1 calc R . . H57C H 1.2950 0.3278 0.4930 0.046 Uiso 1 1 calc R . . C58 C 1.3352(3) 0.1864(3) 0.51192(11) 0.0355(12) Uani 1 1 d . . . H58A H 1.3119 0.1893 0.4910 0.053 Uiso 1 1 calc R . . H58B H 1.3155 0.1387 0.5225 0.053 Uiso 1 1 calc R . . H58C H 1.3935 0.1840 0.5103 0.053 Uiso 1 1 calc R . . N4 N 1.3757(2) 0.2891(2) 0.58756(9) 0.0248(8) Uani 1 1 d . . . C59 C 1.4117(3) 0.3648(3) 0.57937(12) 0.0319(11) Uani 1 1 d . . . H59A H 1.4440 0.3840 0.5968 0.048 Uiso 1 1 calc R . . H59B H 1.3696 0.4035 0.5747 0.048 Uiso 1 1 calc R . . H59C H 1.4457 0.3579 0.5610 0.048 Uiso 1 1 calc R . . C60 C 1.4371(3) 0.2294(3) 0.59450(11) 0.0311(11) Uani 1 1 d . . . H60A H 1.4714 0.2221 0.5763 0.047 Uiso 1 1 calc R . . H60B H 1.4114 0.1788 0.5997 0.047 Uiso 1 1 calc R . . H60C H 1.4695 0.2474 0.6121 0.047 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 C1 0.016(2) 0.026(2) 0.0133(19) -0.0006(17) 0.0043(16) -0.0050(17) C2 0.019(2) 0.038(3) 0.021(2) 0.000(2) -0.0009(18) -0.0043(19) C3 0.024(2) 0.037(3) 0.024(2) -0.016(2) 0.0028(19) -0.014(2) C4 0.023(2) 0.025(2) 0.037(3) -0.007(2) 0.009(2) -0.009(2) C5 0.020(2) 0.019(2) 0.030(2) -0.0066(19) 0.0091(18) -0.0050(17) C6 0.025(2) 0.014(2) 0.042(3) 0.001(2) 0.006(2) -0.0028(18) C7 0.023(2) 0.014(2) 0.034(2) 0.0013(19) 0.0065(19) 0.0006(17) C8 0.039(3) 0.016(2) 0.043(3) 0.011(2) 0.006(2) 0.002(2) C9 0.042(3) 0.031(3) 0.031(3) 0.016(2) -0.004(2) 0.011(2) C10 0.031(2) 0.027(2) 0.028(2) 0.005(2) -0.006(2) 0.004(2) C11 0.024(2) 0.020(2) 0.017(2) 0.0030(17) 0.0000(17) 0.0017(18) C12 0.016(2) 0.015(2) 0.020(2) -0.0008(17) 0.0047(16) 0.0006(16) C13 0.0153(19) 0.0125(19) 0.0146(19) -0.0018(16) 0.0029(15) 0.0009(16) C14 0.0140(19) 0.019(2) 0.0152(19) -0.0042(16) 0.0039(15) 0.0003(16) P1 0.0193(5) 0.0204(6) 0.0297(6) 0.0059(5) -0.0092(5) -0.0009(5) C15 0.027(2) 0.042(3) 0.026(2) 0.012(2) -0.001(2) 0.006(2) C16 0.033(3) 0.040(3) 0.032(3) 0.007(2) -0.004(2) -0.006(2) C17 0.063(4) 0.052(4) 0.040(3) 0.019(3) 0.000(3) 0.025(3) C18 0.041(3) 0.030(3) 0.028(3) -0.003(2) 0.002(2) 0.007(2) C19 0.041(3) 0.056(4) 0.038(3) -0.007(3) 0.009(2) 0.006(3) C20 0.070(4) 0.038(3) 0.034(3) -0.007(2) -0.004(3) 0.016(3) P11 0.0226(5) 0.0184(5) 0.0152(5) 0.0014(4) -0.0047(4) 0.0010(4) C21 0.033(3) 0.033(3) 0.027(2) -0.002(2) -0.010(2) 0.000(2) C22 0.025(2) 0.046(3) 0.045(3) -0.003(3) -0.009(2) -0.003(2) C23 0.047(3) 0.054(4) 0.050(3) -0.025(3) -0.022(3) 0.005(3) C24 0.030(2) 0.024(2) 0.018(2) 0.0012(18) 0.0020(18) 0.0015(19) C25 0.024(2) 0.039(3) 0.028(2) 0.003(2) 0.0026(19) 0.000(2) C26 0.043(3) 0.038(3) 0.022(2) 0.007(2) 0.003(2) 0.005(2) P13 0.0138(5) 0.0188(5) 0.0163(5) 0.0020(4) 0.0001(4) -0.0020(4) N1 0.026(2) 0.044(2) 0.0150(18) 0.0008(17) 0.0066(15) -0.0093(18) C27 0.028(3) 0.064(4) 0.029(3) -0.023(3) 0.004(2) 0.002(3) C28 0.023(2) 0.079(4) 0.028(3) 0.020(3) -0.002(2) -0.016(3) N2 0.0133(17) 0.0231(19) 0.031(2) 0.0027(16) 0.0010(15) 0.0012(15) C29 0.020(2) 0.037(3) 0.037(3) -0.004(2) 0.003(2) 0.007(2) C30 0.017(2) 0.040(3) 0.040(3) 0.006(2) -0.0026(19) -0.007(2) C31 0.021(2) 0.025(2) 0.018(2) 0.0049(18) 0.0065(17) 0.0026(18) C32 0.022(2) 0.034(3) 0.020(2) 0.003(2) 0.0016(18) 0.0072(19) C33 0.020(2) 0.045(3) 0.025(2) 0.018(2) 0.0044(19) 0.008(2) C34 0.019(2) 0.031(3) 0.037(3) 0.023(2) 0.007(2) 0.0074(19) C35 0.017(2) 0.025(2) 0.029(2) 0.016(2) 0.0033(18) 0.0033(18) C36 0.022(2) 0.016(2) 0.045(3) 0.012(2) 0.005(2) 0.0045(18) C37 0.022(2) 0.018(2) 0.038(3) 0.003(2) 0.0060(19) 0.0004(18) C38 0.029(3) 0.012(2) 0.057(3) -0.001(2) 0.004(2) -0.0017(19) C39 0.037(3) 0.020(2) 0.047(3) -0.012(2) -0.001(2) -0.003(2) C40 0.031(2) 0.020(2) 0.036(3) -0.005(2) -0.004(2) -0.0019(19) C41 0.020(2) 0.011(2) 0.026(2) 0.0023(17) 0.0035(17) 0.0012(16) C42 0.018(2) 0.015(2) 0.028(2) 0.0064(18) 0.0011(17) -0.0009(16) C43 0.018(2) 0.017(2) 0.021(2) 0.0048(17) 0.0054(16) 0.0045(16) C44 0.016(2) 0.026(2) 0.021(2) 0.0089(18) 0.0028(17) 0.0029(17) P31 0.0229(6) 0.0255(6) 0.0228(6) 0.0020(5) -0.0032(5) -0.0003(5) C45 0.045(3) 0.031(3) 0.025(2) -0.006(2) -0.006(2) 0.008(2) C46 0.051(3) 0.045(3) 0.032(3) -0.009(2) 0.002(2) 0.010(3) C47 0.055(4) 0.034(3) 0.049(3) -0.011(3) -0.010(3) 0.001(3) C48 0.027(2) 0.028(2) 0.023(2) 0.0043(19) 0.0019(18) -0.0032(19) C49 0.030(3) 0.040(3) 0.037(3) 0.002(2) 0.005(2) 0.003(2) C50 0.042(3) 0.042(3) 0.027(3) 0.008(2) 0.004(2) -0.007(2) P41 0.0239(5) 0.0169(5) 0.0164(5) -0.0003(4) -0.0017(4) 0.0005(4) C51 0.017(2) 0.029(2) 0.034(3) 0.000(2) -0.0065(18) 0.0006(19) C52 0.030(3) 0.037(3) 0.040(3) 0.008(2) -0.003(2) 0.010(2) C53 0.041(3) 0.045(3) 0.030(3) -0.003(2) -0.014(2) 0.001(2) C54 0.025(2) 0.024(2) 0.022(2) -0.0018(19) 0.0071(18) 0.0059(18) C55 0.031(3) 0.029(3) 0.033(3) 0.002(2) 0.007(2) 0.006(2) C56 0.029(2) 0.035(3) 0.028(2) 0.004(2) 0.008(2) 0.004(2) P43 0.0182(5) 0.0183(5) 0.0197(5) 0.0043(4) 0.0023(4) 0.0026(4) N3 0.031(2) 0.025(2) 0.0209(19) 0.0039(16) 0.0064(16) 0.0070(17) C57 0.033(3) 0.030(3) 0.028(2) 0.008(2) 0.010(2) 0.005(2) C58 0.041(3) 0.037(3) 0.028(3) 0.003(2) 0.013(2) 0.009(2) N4 0.0182(18) 0.0224(19) 0.034(2) 0.0030(17) -0.0024(16) 0.0020(15) C59 0.021(2) 0.032(3) 0.043(3) 0.007(2) 0.000(2) -0.003(2) C60 0.021(2) 0.037(3) 0.035(3) 0.002(2) -0.004(2) 0.011(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 C1 C2 1.370(6) . ? C1 C14 1.461(6) . ? C1 P1 1.848(4) . ? C2 C3 1.417(7) . ? C2 H2A 0.9500 . ? C3 C4 1.349(7) . ? C3 H3A 0.9500 . ? C4 C5 1.418(6) . ? C4 H4A 0.9500 . ? C5 C6 1.392(6) . ? C5 C14 1.443(6) . ? C6 C7 1.399(6) . ? C6 H6A 0.9500 . ? C7 C8 1.434(6) . ? C7 C12 1.449(6) . ? C8 C9 1.355(7) . ? C8 H8A 0.9500 . ? C9 C10 1.412(7) . ? C9 H9A 0.9500 . ? C10 C11 1.369(6) . ? C10 H10A 0.9500 . ? C11 C12 1.455(6) . ? C11 P11 1.857(4) . ? C12 C13 1.437(5) . ? C13 C14 1.434(5) . ? C13 P13 1.871(4) . ? P1 C18 1.859(5) . ? P1 C15 1.877(5) . ? C15 C17 1.508(7) . ? C15 C16 1.535(7) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.510(7) . ? C18 C20 1.542(7) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? P11 C21 1.865(5) . ? P11 C24 1.879(4) . ? C21 C22 1.518(7) . ? C21 C23 1.541(7) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.524(6) . ? C24 C26 1.534(6) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? P13 N1 1.721(4) . ? P13 N2 1.728(4) . ? N1 C27 1.451(6) . ? N1 C28 1.471(6) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? N2 C29 1.456(6) . ? N2 C30 1.465(5) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.378(6) . ? C31 C44 1.440(6) . ? C31 P31 1.854(4) . ? C32 C33 1.415(6) . ? C32 H32A 0.9500 . ? C33 C34 1.342(7) . ? C33 H33A 0.9500 . ? C34 C35 1.430(6) . ? C34 H34A 0.9500 . ? C35 C36 1.381(7) . ? C35 C44 1.445(6) . ? C36 C37 1.395(6) . ? C36 H36A 0.9500 . ? C37 C38 1.436(7) . ? C37 C42 1.442(6) . ? C38 C39 1.335(7) . ? C38 H38A 0.9500 . ? C39 C40 1.426(7) . ? C39 H39A 0.9500 . ? C40 C41 1.375(6) . ? C40 H40A 0.9500 . ? C41 C42 1.451(6) . ? C41 P41 1.842(4) . ? C42 C43 1.427(6) . ? C43 C44 1.431(6) . ? C43 P43 1.879(4) . ? P31 C45 1.852(5) . ? P31 C48 1.893(5) . ? C45 C46 1.534(7) . ? C45 C47 1.540(7) . ? C45 H45A 1.0000 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 C50 1.519(6) . ? C48 C49 1.536(6) . ? C48 H48A 1.0000 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? P41 C54 1.885(4) . ? P41 C51 1.890(4) . ? C51 C53 1.521(7) . ? C51 C52 1.527(6) . ? C51 H51A 1.0000 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 C56 1.529(6) . ? C54 C55 1.549(6) . ? C54 H54A 1.0000 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? P43 N3 1.706(4) . ? P43 N4 1.740(4) . ? N3 C57 1.446(6) . ? N3 C58 1.459(6) . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? N4 C59 1.451(6) . ? N4 C60 1.468(5) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 118.8(4) . . ? C2 C1 P1 121.2(3) . . ? C14 C1 P1 119.2(3) . . ? C1 C2 C3 122.6(4) . . ? C1 C2 H2A 118.7 . . ? C3 C2 H2A 118.7 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 119.8(4) . . ? C6 C5 C14 119.6(4) . . ? C4 C5 C14 120.5(4) . . ? C5 C6 C7 121.3(4) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C6 C7 C8 120.1(4) . . ? C6 C7 C12 120.2(4) . . ? C8 C7 C12 119.5(4) . . ? C9 C8 C7 120.6(4) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 120.1(4) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C11 C10 C9 122.3(4) . . ? C11 C10 H10A 118.8 . . ? C9 C10 H10A 118.8 . . ? C10 C11 C12 119.3(4) . . ? C10 C11 P11 120.9(3) . . ? C12 C11 P11 119.0(3) . . ? C13 C12 C7 117.9(4) . . ? C13 C12 C11 125.2(4) . . ? C7 C12 C11 116.9(4) . . ? C14 C13 C12 118.5(3) . . ? C14 C13 P13 120.5(3) . . ? C12 C13 P13 119.6(3) . . ? C13 C14 C5 119.0(4) . . ? C13 C14 C1 124.2(4) . . ? C5 C14 C1 116.8(4) . . ? C1 P1 C18 97.7(2) . . ? C1 P1 C15 101.6(2) . . ? C18 P1 C15 104.4(2) . . ? C17 C15 C16 109.3(4) . . ? C17 C15 P1 110.1(4) . . ? C16 C15 P1 111.3(3) . . ? C17 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? P1 C15 H15A 108.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 111.7(4) . . ? C19 C18 P1 118.0(3) . . ? C20 C18 P1 110.6(4) . . ? C19 C18 H18A 105.1 . . ? C20 C18 H18A 105.1 . . ? P1 C18 H18A 105.1 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 P11 C21 103.2(2) . . ? C11 P11 C24 99.6(2) . . ? C21 P11 C24 100.5(2) . . ? C22 C21 C23 109.4(4) . . ? C22 C21 P11 111.5(3) . . ? C23 C21 P11 109.2(3) . . ? C22 C21 H21A 108.9 . . ? C23 C21 H21A 108.9 . . ? P11 C21 H21A 108.9 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C26 111.0(4) . . ? C25 C24 P11 109.4(3) . . ? C26 C24 P11 117.0(3) . . ? C25 C24 H24A 106.2 . . ? C26 C24 H24A 106.2 . . ? P11 C24 H24A 106.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 P13 N2 105.52(19) . . ? N1 P13 C13 98.98(18) . . ? N2 P13 C13 98.58(17) . . ? C27 N1 C28 112.3(4) . . ? C27 N1 P13 126.2(3) . . ? C28 N1 P13 112.9(3) . . ? N1 C27 H27A 109.5 . . ? N1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N1 C28 H28A 109.5 . . ? N1 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N1 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C29 N2 C30 110.3(4) . . ? C29 N2 P13 125.8(3) . . ? C30 N2 P13 112.2(3) . . ? N2 C29 H29A 109.5 . . ? N2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N2 C30 H30A 109.5 . . ? N2 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N2 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C44 119.4(4) . . ? C32 C31 P31 122.6(4) . . ? C44 C31 P31 117.2(3) . . ? C31 C32 C33 121.7(4) . . ? C31 C32 H32A 119.2 . . ? C33 C32 H32A 119.2 . . ? C34 C33 C32 120.7(4) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C33 C34 C35 120.5(4) . . ? C33 C34 H34A 119.7 . . ? C35 C34 H34A 119.7 . . ? C36 C35 C34 120.7(4) . . ? C36 C35 C44 119.7(4) . . ? C34 C35 C44 119.6(4) . . ? C35 C36 C37 121.7(4) . . ? C35 C36 H36A 119.1 . . ? C37 C36 H36A 119.1 . . ? C36 C37 C38 121.6(4) . . ? C36 C37 C42 118.9(4) . . ? C38 C37 C42 119.4(4) . . ? C39 C38 C37 120.6(4) . . ? C39 C38 H38A 119.7 . . ? C37 C38 H38A 119.7 . . ? C38 C39 C40 120.6(4) . . ? C38 C39 H39A 119.7 . . ? C40 C39 H39A 119.7 . . ? C41 C40 C39 121.5(4) . . ? C41 C40 H40A 119.2 . . ? C39 C40 H40A 119.2 . . ? C40 C41 C42 119.2(4) . . ? C40 C41 P41 122.2(3) . . ? C42 C41 P41 117.5(3) . . ? C43 C42 C37 118.6(4) . . ? C43 C42 C41 124.1(4) . . ? C37 C42 C41 117.3(4) . . ? C42 C43 C44 117.7(4) . . ? C42 C43 P43 120.4(3) . . ? C44 C43 P43 120.5(3) . . ? C43 C44 C31 124.1(4) . . ? C43 C44 C35 118.3(4) . . ? C31 C44 C35 117.7(4) . . ? C45 P31 C31 104.4(2) . . ? C45 P31 C48 105.4(2) . . ? C31 P31 C48 96.90(19) . . ? C46 C45 C47 110.0(4) . . ? C46 C45 P31 111.1(4) . . ? C47 C45 P31 107.3(3) . . ? C46 C45 H45A 109.5 . . ? C47 C45 H45A 109.5 . . ? P31 C45 H45A 109.5 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C50 C48 C49 111.4(4) . . ? C50 C48 P31 110.7(3) . . ? C49 C48 P31 115.3(3) . . ? C50 C48 H48A 106.2 . . ? C49 C48 H48A 106.2 . . ? P31 C48 H48A 106.2 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C41 P41 C54 98.20(19) . . ? C41 P41 C51 104.1(2) . . ? C54 P41 C51 102.5(2) . . ? C53 C51 C52 108.2(4) . . ? C53 C51 P41 119.5(3) . . ? C52 C51 P41 109.4(3) . . ? C53 C51 H51A 106.3 . . ? C52 C51 H51A 106.3 . . ? P41 C51 H51A 106.3 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C56 C54 C55 110.2(4) . . ? C56 C54 P41 109.1(3) . . ? C55 C54 P41 111.5(3) . . ? C56 C54 H54A 108.7 . . ? C55 C54 H54A 108.7 . . ? P41 C54 H54A 108.7 . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C54 C56 H56A 109.5 . . ? C54 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C54 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? N3 P43 N4 106.76(19) . . ? N3 P43 C43 96.93(18) . . ? N4 P43 C43 99.45(18) . . ? C57 N3 C58 112.3(3) . . ? C57 N3 P43 127.6(3) . . ? C58 N3 P43 118.4(3) . . ? N3 C57 H57A 109.5 . . ? N3 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? N3 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? N3 C58 H58A 109.5 . . ? N3 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? N3 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C59 N4 C60 111.0(4) . . ? C59 N4 P43 124.7(3) . . ? C60 N4 P43 111.1(3) . . ? N4 C59 H59A 109.5 . . ? N4 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? N4 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? N4 C60 H60A 109.5 . . ? N4 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? N4 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 -1.1(6) . . . . ? P1 C1 C2 C3 168.5(3) . . . . ? C1 C2 C3 C4 -5.7(7) . . . . ? C2 C3 C4 C5 4.5(7) . . . . ? C3 C4 C5 C6 179.6(4) . . . . ? C3 C4 C5 C14 3.4(6) . . . . ? C4 C5 C6 C7 177.0(4) . . . . ? C14 C5 C6 C7 -6.7(6) . . . . ? C5 C6 C7 C8 -179.3(4) . . . . ? C5 C6 C7 C12 6.4(6) . . . . ? C6 C7 C8 C9 -177.6(4) . . . . ? C12 C7 C8 C9 -3.3(7) . . . . ? C7 C8 C9 C10 -5.6(7) . . . . ? C8 C9 C10 C11 5.8(8) . . . . ? C9 C10 C11 C12 2.9(7) . . . . ? C9 C10 C11 P11 -167.2(4) . . . . ? C6 C7 C12 C13 7.4(6) . . . . ? C8 C7 C12 C13 -167.0(4) . . . . ? C6 C7 C12 C11 -174.1(4) . . . . ? C8 C7 C12 C11 11.5(6) . . . . ? C10 C11 C12 C13 167.1(4) . . . . ? P11 C11 C12 C13 -22.7(5) . . . . ? C10 C11 C12 C7 -11.3(6) . . . . ? P11 C11 C12 C7 158.9(3) . . . . ? C7 C12 C13 C14 -20.5(5) . . . . ? C11 C12 C13 C14 161.1(4) . . . . ? C7 C12 C13 P13 146.0(3) . . . . ? C11 C12 C13 P13 -32.4(5) . . . . ? C12 C13 C14 C5 20.3(5) . . . . ? P13 C13 C14 C5 -146.0(3) . . . . ? C12 C13 C14 C1 -160.4(4) . . . . ? P13 C13 C14 C1 33.2(5) . . . . ? C6 C5 C14 C13 -6.7(6) . . . . ? C4 C5 C14 C13 169.5(4) . . . . ? C6 C5 C14 C1 174.0(4) . . . . ? C4 C5 C14 C1 -9.8(6) . . . . ? C2 C1 C14 C13 -170.7(4) . . . . ? P1 C1 C14 C13 19.5(5) . . . . ? C2 C1 C14 C5 8.6(5) . . . . ? P1 C1 C14 C5 -161.3(3) . . . . ? C2 C1 P1 C18 -85.3(4) . . . . ? C14 C1 P1 C18 84.3(3) . . . . ? C2 C1 P1 C15 21.3(4) . . . . ? C14 C1 P1 C15 -169.2(3) . . . . ? C1 P1 C15 C17 -172.2(4) . . . . ? C18 P1 C15 C17 -71.1(4) . . . . ? C1 P1 C15 C16 66.3(4) . . . . ? C18 P1 C15 C16 167.5(4) . . . . ? C1 P1 C18 C19 64.2(4) . . . . ? C15 P1 C18 C19 -39.9(5) . . . . ? C1 P1 C18 C20 -165.5(4) . . . . ? C15 P1 C18 C20 90.4(4) . . . . ? C10 C11 P11 C21 -24.8(4) . . . . ? C12 C11 P11 C21 165.0(3) . . . . ? C10 C11 P11 C24 78.5(4) . . . . ? C12 C11 P11 C24 -91.6(3) . . . . ? C11 P11 C21 C22 -68.1(4) . . . . ? C24 P11 C21 C22 -170.7(4) . . . . ? C11 P11 C21 C23 171.0(4) . . . . ? C24 P11 C21 C23 68.3(4) . . . . ? C11 P11 C24 C25 76.1(3) . . . . ? C21 P11 C24 C25 -178.3(3) . . . . ? C11 P11 C24 C26 -51.2(4) . . . . ? C21 P11 C24 C26 54.4(4) . . . . ? C14 C13 P13 N1 28.7(3) . . . . ? C12 C13 P13 N1 -137.5(3) . . . . ? C14 C13 P13 N2 136.0(3) . . . . ? C12 C13 P13 N2 -30.2(3) . . . . ? N2 P13 N1 C27 -51.3(4) . . . . ? C13 P13 N1 C27 50.3(4) . . . . ? N2 P13 N1 C28 93.7(3) . . . . ? C13 P13 N1 C28 -164.8(3) . . . . ? N1 P13 N2 C29 53.7(4) . . . . ? C13 P13 N2 C29 -48.2(4) . . . . ? N1 P13 N2 C30 -85.4(3) . . . . ? C13 P13 N2 C30 172.7(3) . . . . ? C44 C31 C32 C33 -0.6(6) . . . . ? P31 C31 C32 C33 168.6(3) . . . . ? C31 C32 C33 C34 -3.6(7) . . . . ? C32 C33 C34 C35 1.7(7) . . . . ? C33 C34 C35 C36 -177.5(4) . . . . ? C33 C34 C35 C44 4.3(6) . . . . ? C34 C35 C36 C37 173.2(4) . . . . ? C44 C35 C36 C37 -8.6(6) . . . . ? C35 C36 C37 C38 -176.5(4) . . . . ? C35 C36 C37 C42 6.3(6) . . . . ? C36 C37 C38 C39 177.1(4) . . . . ? C42 C37 C38 C39 -5.7(7) . . . . ? C37 C38 C39 C40 -4.6(7) . . . . ? C38 C39 C40 C41 7.2(7) . . . . ? C39 C40 C41 C42 0.7(7) . . . . ? C39 C40 C41 P41 -166.9(4) . . . . ? C36 C37 C42 C43 10.8(6) . . . . ? C38 C37 C42 C43 -166.4(4) . . . . ? C36 C37 C42 C41 -169.6(4) . . . . ? C38 C37 C42 C41 13.1(6) . . . . ? C40 C41 C42 C43 168.9(4) . . . . ? P41 C41 C42 C43 -22.9(5) . . . . ? C40 C41 C42 C37 -10.6(6) . . . . ? P41 C41 C42 C37 157.6(3) . . . . ? C37 C42 C43 C44 -25.2(6) . . . . ? C41 C42 C43 C44 155.3(4) . . . . ? C37 C42 C43 P43 141.4(3) . . . . ? C41 C42 C43 P43 -38.1(5) . . . . ? C42 C43 C44 C31 -157.0(4) . . . . ? P43 C43 C44 C31 36.4(5) . . . . ? C42 C43 C44 C35 22.9(6) . . . . ? P43 C43 C44 C35 -143.7(3) . . . . ? C32 C31 C44 C43 -173.8(4) . . . . ? P31 C31 C44 C43 16.4(5) . . . . ? C32 C31 C44 C35 6.3(6) . . . . ? P31 C31 C44 C35 -163.5(3) . . . . ? C36 C35 C44 C43 -6.2(6) . . . . ? C34 C35 C44 C43 172.0(4) . . . . ? C36 C35 C44 C31 173.6(4) . . . . ? C34 C35 C44 C31 -8.2(6) . . . . ? C32 C31 P31 C45 15.9(4) . . . . ? C44 C31 P31 C45 -174.6(3) . . . . ? C32 C31 P31 C48 -91.9(4) . . . . ? C44 C31 P31 C48 77.5(3) . . . . ? C31 P31 C45 C46 65.7(4) . . . . ? C48 P31 C45 C46 167.2(3) . . . . ? C31 P31 C45 C47 -174.0(4) . . . . ? C48 P31 C45 C47 -72.5(4) . . . . ? C45 P31 C48 C50 93.5(4) . . . . ? C31 P31 C48 C50 -159.4(3) . . . . ? C45 P31 C48 C49 -34.1(4) . . . . ? C31 P31 C48 C49 72.9(4) . . . . ? C40 C41 P41 C54 64.0(4) . . . . ? C42 C41 P41 C54 -103.8(3) . . . . ? C40 C41 P41 C51 -41.2(4) . . . . ? C42 C41 P41 C51 151.0(3) . . . . ? C41 P41 C51 C53 79.3(4) . . . . ? C54 P41 C51 C53 -22.6(4) . . . . ? C41 P41 C51 C52 -155.3(3) . . . . ? C54 P41 C51 C52 102.8(3) . . . . ? C41 P41 C54 C56 177.1(3) . . . . ? C51 P41 C54 C56 -76.4(3) . . . . ? C41 P41 C54 C55 55.3(3) . . . . ? C51 P41 C54 C55 161.7(3) . . . . ? C42 C43 P43 N3 -129.7(3) . . . . ? C44 C43 P43 N3 36.6(4) . . . . ? C42 C43 P43 N4 -21.3(4) . . . . ? C44 C43 P43 N4 144.9(3) . . . . ? N4 P43 N3 C57 -58.0(4) . . . . ? C43 P43 N3 C57 44.0(4) . . . . ? N4 P43 N3 C58 106.3(4) . . . . ? C43 P43 N3 C58 -151.6(4) . . . . ? N3 P43 N4 C59 44.6(4) . . . . ? C43 P43 N4 C59 -55.6(4) . . . . ? N3 P43 N4 C60 -92.8(3) . . . . ? C43 P43 N4 C60 166.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.528 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.080 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 635697' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H36 P2' _chemical_formula_sum 'C26 H36 P2' _chemical_formula_weight 410.49 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.671(11) _cell_length_b 12.549(8) _cell_length_c 13.131(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.265(10) _cell_angle_gamma 90.00 _cell_volume 2362(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3870 _cell_measurement_theta_min 2.1573 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Platelet _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6478 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17029 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4044 _reflns_number_gt 3204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4044 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.29733(4) -0.14951(4) 0.02383(5) 0.02139(18) Uani 1 1 d . . . C1 C 0.38900(15) -0.12606(17) 0.14209(17) 0.0207(5) Uani 1 1 d . . . C2 C 0.46759(16) -0.18743(18) 0.16873(18) 0.0240(5) Uani 1 1 d . . . H2A H 0.4755 -0.2453 0.1248 0.029 Uiso 1 1 calc R . . C3 C 0.53791(16) -0.16803(18) 0.25962(18) 0.0259(5) Uani 1 1 d . . . H3A H 0.5921 -0.2115 0.2744 0.031 Uiso 1 1 calc R . . C4 C 0.52770(15) -0.08801(17) 0.32471(18) 0.0239(5) Uani 1 1 d . . . H4A H 0.5751 -0.0753 0.3850 0.029 Uiso 1 1 calc R . . C5 C 0.44642(15) -0.02212(17) 0.30406(16) 0.0211(5) Uani 1 1 d . . . C6 C 0.43300(15) 0.05833(17) 0.37248(17) 0.0217(5) Uani 1 1 d . . . H6A H 0.4793 0.0696 0.4341 0.026 Uiso 1 1 calc R . . C7 C 0.35338(15) 0.12318(17) 0.35333(17) 0.0213(5) Uani 1 1 d . . . C8 C 0.34009(16) 0.20415(17) 0.42548(17) 0.0239(5) Uani 1 1 d . . . H8A H 0.3861 0.2149 0.4875 0.029 Uiso 1 1 calc R . . C9 C 0.26232(16) 0.26562(18) 0.40604(18) 0.0261(5) Uani 1 1 d . . . H9A H 0.2539 0.3189 0.4546 0.031 Uiso 1 1 calc R . . C10 C 0.19356(16) 0.25070(18) 0.31360(18) 0.0251(5) Uani 1 1 d . . . H10A H 0.1396 0.2946 0.3019 0.030 Uiso 1 1 calc R . . C11 C 0.20167(15) 0.17530(17) 0.23996(17) 0.0205(5) Uani 1 1 d . . . P11 P 0.11515(4) 0.16049(4) 0.11612(5) 0.02159(18) Uani 1 1 d . . . C12 C 0.28368(14) 0.10794(16) 0.25982(17) 0.0191(5) Uani 1 1 d . . . C13 C 0.29784(14) 0.02726(16) 0.19107(17) 0.0201(5) Uani 1 1 d . . . H13A H 0.2523 0.0175 0.1285 0.024 Uiso 1 1 calc R . . C14 C 0.37584(15) -0.03955(17) 0.21031(17) 0.0203(5) Uani 1 1 d . . . C15 C 0.32087(16) -0.28806(17) -0.01360(18) 0.0265(5) Uani 1 1 d . . . H15A H 0.3882 -0.2952 -0.0164 0.032 Uiso 1 1 calc R . . C16 C 0.29799(17) -0.36499(19) 0.0678(2) 0.0331(6) Uani 1 1 d . . . H16A H 0.3104 -0.4383 0.0487 0.050 Uiso 1 1 calc R . . H16B H 0.2321 -0.3578 0.0706 0.050 Uiso 1 1 calc R . . H16C H 0.3369 -0.3482 0.1363 0.050 Uiso 1 1 calc R . . C17 C 0.25989(17) -0.31355(19) -0.12133(19) 0.0321(6) Uani 1 1 d . . . H17A H 0.2726 -0.3864 -0.1413 0.048 Uiso 1 1 calc R . . H17B H 0.2743 -0.2634 -0.1729 0.048 Uiso 1 1 calc R . . H17C H 0.1939 -0.3071 -0.1184 0.048 Uiso 1 1 calc R . . C18 C 0.34528(16) -0.06179(19) -0.06785(18) 0.0281(5) Uani 1 1 d . . . H18A H 0.3619 0.0067 -0.0295 0.034 Uiso 1 1 calc R . . C19 C 0.43488(17) -0.1002(2) -0.0965(2) 0.0329(6) Uani 1 1 d . . . H19A H 0.4543 -0.0490 -0.1441 0.049 Uiso 1 1 calc R . . H19B H 0.4242 -0.1699 -0.1307 0.049 Uiso 1 1 calc R . . H19C H 0.4839 -0.1066 -0.0333 0.049 Uiso 1 1 calc R . . C20 C 0.26994(18) -0.0330(2) -0.1629(2) 0.0369(6) Uani 1 1 d . . . H20A H 0.2966 0.0132 -0.2093 0.055 Uiso 1 1 calc R . . H20B H 0.2190 0.0045 -0.1404 0.055 Uiso 1 1 calc R . . H20C H 0.2458 -0.0982 -0.2002 0.055 Uiso 1 1 calc R . . C21 C 0.02494(16) 0.07252(18) 0.15499(18) 0.0275(5) Uani 1 1 d . . . H21A H -0.0291 0.0697 0.0941 0.033 Uiso 1 1 calc R . . C22 C 0.06265(18) -0.04058(19) 0.1726(2) 0.0372(6) Uani 1 1 d . . . H22A H 0.0153 -0.0865 0.1925 0.056 Uiso 1 1 calc R . . H22B H 0.1189 -0.0405 0.2283 0.056 Uiso 1 1 calc R . . H22C H 0.0780 -0.0675 0.1082 0.056 Uiso 1 1 calc R . . C23 C -0.01296(17) 0.1109(2) 0.2478(2) 0.0373(6) Uani 1 1 d . . . H23A H -0.0595 0.0601 0.2619 0.056 Uiso 1 1 calc R . . H23B H -0.0420 0.1810 0.2323 0.056 Uiso 1 1 calc R . . H23C H 0.0383 0.1162 0.3092 0.056 Uiso 1 1 calc R . . C24 C 0.05710(16) 0.29330(18) 0.10003(19) 0.0276(5) Uani 1 1 d . . . H24A H 0.0355 0.3117 0.1652 0.033 Uiso 1 1 calc R . . C25 C 0.12628(18) 0.37795(18) 0.0800(2) 0.0330(6) Uani 1 1 d . . . H25A H 0.0957 0.4478 0.0722 0.049 Uiso 1 1 calc R . . H25B H 0.1474 0.3604 0.0160 0.049 Uiso 1 1 calc R . . H25C H 0.1800 0.3799 0.1388 0.049 Uiso 1 1 calc R . . C26 C -0.02682(17) 0.2874(2) 0.0093(2) 0.0347(6) Uani 1 1 d . . . H26A H -0.0582 0.3568 0.0003 0.052 Uiso 1 1 calc R . . H26B H -0.0703 0.2330 0.0239 0.052 Uiso 1 1 calc R . . H26C H -0.0060 0.2687 -0.0545 0.052 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 0.0204(3) 0.0217(3) 0.0215(4) -0.0025(2) 0.0034(2) 0.0020(2) C1 0.0217(11) 0.0211(11) 0.0195(13) -0.0003(9) 0.0049(9) -0.0004(8) C2 0.0263(12) 0.0223(11) 0.0241(14) -0.0018(10) 0.0071(10) 0.0002(9) C3 0.0238(12) 0.0300(13) 0.0241(14) 0.0047(10) 0.0054(10) 0.0043(9) C4 0.0234(12) 0.0262(12) 0.0216(13) 0.0020(10) 0.0037(9) -0.0011(9) C5 0.0238(11) 0.0214(11) 0.0187(13) 0.0023(9) 0.0060(9) -0.0022(9) C6 0.0221(11) 0.0248(12) 0.0172(12) 0.0010(9) 0.0021(9) -0.0034(9) C7 0.0248(12) 0.0227(11) 0.0178(13) 0.0020(9) 0.0076(9) -0.0015(9) C8 0.0292(13) 0.0258(12) 0.0167(13) -0.0011(9) 0.0048(10) -0.0048(9) C9 0.0334(13) 0.0231(11) 0.0243(14) -0.0052(10) 0.0116(10) -0.0018(10) C10 0.0260(12) 0.0245(12) 0.0263(14) -0.0012(10) 0.0089(10) 0.0015(9) C11 0.0230(11) 0.0207(11) 0.0187(13) 0.0009(9) 0.0069(9) -0.0014(9) P11 0.0227(3) 0.0205(3) 0.0218(4) 0.0004(2) 0.0052(2) 0.0021(2) C12 0.0205(11) 0.0184(11) 0.0191(13) 0.0025(9) 0.0060(9) -0.0028(8) C13 0.0215(11) 0.0200(11) 0.0191(13) 0.0012(9) 0.0053(9) -0.0015(9) C14 0.0229(11) 0.0213(11) 0.0176(13) 0.0013(9) 0.0062(9) -0.0040(9) C15 0.0250(12) 0.0239(12) 0.0290(14) -0.0034(10) 0.0021(10) 0.0027(9) C16 0.0318(14) 0.0261(12) 0.0400(16) 0.0013(11) 0.0046(11) 0.0005(10) C17 0.0331(14) 0.0280(13) 0.0338(16) -0.0108(11) 0.0040(11) 0.0011(10) C18 0.0322(13) 0.0257(12) 0.0255(14) 0.0026(10) 0.0041(10) 0.0005(10) C19 0.0334(14) 0.0357(14) 0.0304(15) 0.0039(11) 0.0086(11) -0.0015(11) C20 0.0420(15) 0.0324(14) 0.0337(16) 0.0051(11) 0.0023(12) 0.0021(11) C21 0.0256(12) 0.0302(13) 0.0257(14) 0.0013(10) 0.0033(10) -0.0046(10) C22 0.0385(15) 0.0288(13) 0.0450(17) 0.0072(12) 0.0104(12) -0.0072(11) C23 0.0301(14) 0.0476(16) 0.0363(17) 0.0037(13) 0.0121(12) -0.0052(12) C24 0.0309(13) 0.0240(12) 0.0291(15) 0.0011(10) 0.0093(11) 0.0041(10) C25 0.0447(16) 0.0210(12) 0.0331(15) 0.0015(10) 0.0077(12) 0.0018(10) C26 0.0331(14) 0.0316(14) 0.0376(16) 0.0073(11) 0.0036(11) 0.0083(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.849(2) . ? P1 C15 1.859(2) . ? P1 C18 1.875(2) . ? C1 C2 1.369(3) . ? C1 C14 1.446(3) . ? C2 C3 1.423(3) . ? C2 H2A 0.9500 . ? C3 C4 1.348(3) . ? C3 H3A 0.9500 . ? C4 C5 1.429(3) . ? C4 H4A 0.9500 . ? C5 C6 1.393(3) . ? C5 C14 1.447(3) . ? C6 C7 1.402(3) . ? C6 H6A 0.9500 . ? C7 C8 1.431(3) . ? C7 C12 1.434(3) . ? C8 C9 1.356(3) . ? C8 H8A 0.9500 . ? C9 C10 1.416(3) . ? C9 H9A 0.9500 . ? C10 C11 1.376(3) . ? C10 H10A 0.9500 . ? C11 C12 1.448(3) . ? C11 P11 1.847(3) . ? P11 C24 1.863(3) . ? P11 C21 1.876(2) . ? C12 C13 1.401(3) . ? C13 C14 1.398(3) . ? C13 H13A 0.9500 . ? C15 C16 1.530(3) . ? C15 C17 1.538(3) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.521(3) . ? C18 C20 1.524(3) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C23 1.522(3) . ? C21 C22 1.523(3) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.522(3) . ? C24 C25 1.530(3) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C15 103.18(10) . . ? C1 P1 C18 98.09(11) . . ? C15 P1 C18 105.27(11) . . ? C2 C1 C14 118.7(2) . . ? C2 C1 P1 123.22(17) . . ? C14 C1 P1 118.08(16) . . ? C1 C2 C3 122.6(2) . . ? C1 C2 H2A 118.7 . . ? C3 C2 H2A 118.7 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C6 C5 C4 121.6(2) . . ? C6 C5 C14 119.0(2) . . ? C4 C5 C14 119.4(2) . . ? C5 C6 C7 122.1(2) . . ? C5 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C6 C7 C8 121.3(2) . . ? C6 C7 C12 119.4(2) . . ? C8 C7 C12 119.3(2) . . ? C9 C8 C7 120.5(2) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C11 C10 C9 122.8(2) . . ? C11 C10 H10A 118.6 . . ? C9 C10 H10A 118.6 . . ? C10 C11 C12 117.9(2) . . ? C10 C11 P11 122.81(17) . . ? C12 C11 P11 119.28(16) . . ? C11 P11 C24 102.82(11) . . ? C11 P11 C21 102.25(11) . . ? C24 P11 C21 103.03(11) . . ? C13 C12 C7 118.15(19) . . ? C13 C12 C11 122.5(2) . . ? C7 C12 C11 119.37(19) . . ? C14 C13 C12 123.0(2) . . ? C14 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C13 C14 C1 123.4(2) . . ? C13 C14 C5 118.3(2) . . ? C1 C14 C5 118.35(19) . . ? C16 C15 C17 109.9(2) . . ? C16 C15 P1 108.96(17) . . ? C17 C15 P1 109.46(15) . . ? C16 C15 H15A 109.5 . . ? C17 C15 H15A 109.5 . . ? P1 C15 H15A 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 112.8(2) . . ? C19 C18 P1 115.77(17) . . ? C20 C18 P1 111.06(17) . . ? C19 C18 H18A 105.4 . . ? C20 C18 H18A 105.4 . . ? P1 C18 H18A 105.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C23 C21 C22 110.9(2) . . ? C23 C21 P11 115.54(17) . . ? C22 C21 P11 109.58(17) . . ? C23 C21 H21A 106.8 . . ? C22 C21 H21A 106.8 . . ? P11 C21 H21A 106.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C25 110.8(2) . . ? C26 C24 P11 108.64(16) . . ? C25 C24 P11 109.67(17) . . ? C26 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? P11 C24 H24A 109.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C15 P1 C1 C2 17.4(2) . . . . ? C18 P1 C1 C2 -90.5(2) . . . . ? C15 P1 C1 C14 -161.61(17) . . . . ? C18 P1 C1 C14 90.55(18) . . . . ? C14 C1 C2 C3 -1.5(3) . . . . ? P1 C1 C2 C3 179.55(17) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 177.5(2) . . . . ? C3 C4 C5 C14 -2.0(3) . . . . ? C4 C5 C6 C7 -179.7(2) . . . . ? C14 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 178.87(19) . . . . ? C5 C6 C7 C12 -0.9(3) . . . . ? C6 C7 C8 C9 -179.5(2) . . . . ? C12 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C9 C10 C11 P11 -176.65(17) . . . . ? C10 C11 P11 C24 21.7(2) . . . . ? C12 C11 P11 C24 -155.90(16) . . . . ? C10 C11 P11 C21 -84.9(2) . . . . ? C12 C11 P11 C21 97.48(18) . . . . ? C6 C7 C12 C13 0.6(3) . . . . ? C8 C7 C12 C13 -179.24(19) . . . . ? C6 C7 C12 C11 -179.74(19) . . . . ? C8 C7 C12 C11 0.5(3) . . . . ? C10 C11 C12 C13 178.62(19) . . . . ? P11 C11 C12 C13 -3.7(3) . . . . ? C10 C11 C12 C7 -1.1(3) . . . . ? P11 C11 C12 C7 176.65(15) . . . . ? C7 C12 C13 C14 0.9(3) . . . . ? C11 C12 C13 C14 -178.77(19) . . . . ? C12 C13 C14 C1 177.14(19) . . . . ? C12 C13 C14 C5 -2.0(3) . . . . ? C2 C1 C14 C13 -179.4(2) . . . . ? P1 C1 C14 C13 -0.3(3) . . . . ? C2 C1 C14 C5 -0.2(3) . . . . ? P1 C1 C14 C5 178.78(15) . . . . ? C6 C5 C14 C13 1.6(3) . . . . ? C4 C5 C14 C13 -178.87(18) . . . . ? C6 C5 C14 C1 -177.60(18) . . . . ? C4 C5 C14 C1 2.0(3) . . . . ? C1 P1 C15 C16 68.86(18) . . . . ? C18 P1 C15 C16 171.20(16) . . . . ? C1 P1 C15 C17 -170.94(16) . . . . ? C18 P1 C15 C17 -68.60(19) . . . . ? C1 P1 C18 C19 69.3(2) . . . . ? C15 P1 C18 C19 -36.8(2) . . . . ? C1 P1 C18 C20 -160.46(17) . . . . ? C15 P1 C18 C20 93.42(18) . . . . ? C11 P11 C21 C23 53.1(2) . . . . ? C24 P11 C21 C23 -53.3(2) . . . . ? C11 P11 C21 C22 -72.93(19) . . . . ? C24 P11 C21 C22 -179.38(17) . . . . ? C11 P11 C24 C26 -171.17(16) . . . . ? C21 P11 C24 C26 -65.15(19) . . . . ? C11 P11 C24 C25 67.61(18) . . . . ? C21 P11 C24 C25 173.64(16) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.463 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.065 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 635698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H35 O P3 S2.[C2 H4 Cl2]0.5' _chemical_formula_sum 'C27 H37 Cl O P3 S2' _chemical_formula_weight 570.05 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.495(3) _cell_length_b 11.789(4) _cell_length_c 15.095(4) _cell_angle_alpha 97.217(5) _cell_angle_beta 91.854(7) _cell_angle_gamma 108.600(11) _cell_volume 1417.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4387 _cell_measurement_theta_min 1.3638 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6562 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7649 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4431 _reflns_number_gt 3947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.5340P] 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 4431 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 S1 S 0.94394(7) 0.51911(5) 0.74081(3) 0.02102(14) Uani 1 1 d . . . P1 P 0.81346(6) 0.35416(5) 0.76246(3) 0.01268(13) Uani 1 1 d . . . C1 C 0.7133(2) 0.25684(18) 0.65560(12) 0.0122(4) Uani 1 1 d . . . C2 C 0.7880(2) 0.30791(19) 0.58403(13) 0.0149(4) Uani 1 1 d . . . H2A H 0.8950 0.3676 0.5952 0.018 Uiso 1 1 calc R . . C3 C 0.7156(3) 0.27710(19) 0.49517(13) 0.0165(4) Uani 1 1 d . . . H3A H 0.7764 0.3095 0.4473 0.020 Uiso 1 1 calc R . . C4 C 0.5574(3) 0.20022(19) 0.47991(12) 0.0150(4) Uani 1 1 d . . . H4A H 0.5012 0.1865 0.4222 0.018 Uiso 1 1 calc R . . C5 C 0.4742(2) 0.13969(18) 0.54962(12) 0.0123(4) Uani 1 1 d . . . C6 C 0.3139(2) 0.05797(18) 0.52716(12) 0.0141(4) Uani 1 1 d . . . H6A H 0.2629 0.0515 0.4690 0.017 Uiso 1 1 calc R . . C7 C 0.2270(2) -0.01393(18) 0.58693(12) 0.0131(4) Uani 1 1 d . . . C8 C 0.0636(2) -0.09835(19) 0.56335(13) 0.0154(4) Uani 1 1 d . . . H8A H 0.0093 -0.1009 0.5068 0.019 Uiso 1 1 calc R . . C9 C -0.0162(2) -0.17516(19) 0.61996(13) 0.0166(4) Uani 1 1 d . . . H9A H -0.1271 -0.2275 0.6043 0.020 Uiso 1 1 calc R . . C10 C 0.0669(2) -0.17663(18) 0.70205(13) 0.0151(4) Uani 1 1 d . . . H10A H 0.0125 -0.2316 0.7410 0.018 Uiso 1 1 calc R . . C11 C 0.2253(2) -0.09946(18) 0.72601(12) 0.0120(4) Uani 1 1 d . . . C12 C 0.3120(2) -0.01066(18) 0.67114(12) 0.0118(4) Uani 1 1 d . . . C13 C 0.4748(2) 0.07224(18) 0.69693(12) 0.0112(4) Uani 1 1 d . . . C14 C 0.5556(2) 0.15667(18) 0.63884(12) 0.0112(4) Uani 1 1 d . . . P13 P 0.57936(6) 0.03336(5) 0.79329(3) 0.01032(13) Uani 1 1 d . . . S2 S 0.73961(6) -0.04266(5) 0.74677(3) 0.01542(13) Uani 1 1 d . . . O2 O 0.62279(16) 0.12278(12) 0.87708(8) 0.0141(3) Uani 1 1 d . . . P11 P 0.34572(6) -0.10403(5) 0.82333(3) 0.01096(13) Uani 1 1 d . . . C15 C 0.9557(2) 0.2857(2) 0.81347(13) 0.0164(4) Uani 1 1 d . . . H15A H 0.8878 0.2106 0.8363 0.020 Uiso 1 1 calc R . . C16 C 1.0697(3) 0.3720(2) 0.89146(14) 0.0252(5) Uani 1 1 d . . . H16A H 1.1429 0.3325 0.9166 0.038 Uiso 1 1 calc R . . H16B H 1.0017 0.3928 0.9379 0.038 Uiso 1 1 calc R . . H16C H 1.1375 0.4458 0.8697 0.038 Uiso 1 1 calc R . . C17 C 1.0613(3) 0.2514(2) 0.74071(14) 0.0213(5) Uani 1 1 d . . . H17A H 1.1375 0.2149 0.7667 0.032 Uiso 1 1 calc R . . H17B H 1.1258 0.3241 0.7165 0.032 Uiso 1 1 calc R . . H17C H 0.9880 0.1932 0.6925 0.032 Uiso 1 1 calc R . . C18 C 0.6364(2) 0.36226(19) 0.82718(12) 0.0154(4) Uani 1 1 d . . . H18A H 0.5656 0.2782 0.8334 0.019 Uiso 1 1 calc R . . C19 C 0.6941(3) 0.4336(2) 0.92052(14) 0.0259(5) Uani 1 1 d . . . H19A H 0.5969 0.4360 0.9529 0.039 Uiso 1 1 calc R . . H19B H 0.7639 0.5163 0.9153 0.039 Uiso 1 1 calc R . . H19C H 0.7587 0.3944 0.9533 0.039 Uiso 1 1 calc R . . C20 C 0.5326(3) 0.4206(2) 0.77542(14) 0.0228(5) Uani 1 1 d . . . H20A H 0.4378 0.4254 0.8092 0.034 Uiso 1 1 calc R . . H20B H 0.4917 0.3716 0.7168 0.034 Uiso 1 1 calc R . . H20C H 0.6018 0.5021 0.7671 0.034 Uiso 1 1 calc R . . C21 C 0.3536(2) -0.25557(18) 0.83102(12) 0.0144(4) Uani 1 1 d . . . H21A H 0.2421 -0.3048 0.8479 0.017 Uiso 1 1 calc R . . C22 C 0.3863(3) -0.31978(19) 0.74239(13) 0.0178(4) Uani 1 1 d . . . H22A H 0.3891 -0.4003 0.7507 0.027 Uiso 1 1 calc R . . H22B H 0.4935 -0.2724 0.7230 0.027 Uiso 1 1 calc R . . H22C H 0.2972 -0.3278 0.6968 0.027 Uiso 1 1 calc R . . C23 C 0.4825(3) -0.2476(2) 0.90750(13) 0.0211(5) Uani 1 1 d . . . H23A H 0.4875 -0.3285 0.9121 0.032 Uiso 1 1 calc R . . H23B H 0.4499 -0.2141 0.9640 0.032 Uiso 1 1 calc R . . H23C H 0.5922 -0.1949 0.8951 0.032 Uiso 1 1 calc R . . C24 C 0.2654(2) -0.04697(19) 0.92443(12) 0.0160(4) Uani 1 1 d . . . H24A H 0.3565 -0.0227 0.9736 0.019 Uiso 1 1 calc R . . C25 C 0.1167(3) -0.1430(2) 0.95463(14) 0.0255(5) Uani 1 1 d . . . H25A H 0.0782 -0.1083 1.0088 0.038 Uiso 1 1 calc R . . H25B H 0.1503 -0.2117 0.9675 0.038 Uiso 1 1 calc R . . H25C H 0.0262 -0.1705 0.9070 0.038 Uiso 1 1 calc R . . C26 C 0.2229(3) 0.0668(2) 0.90969(14) 0.0219(5) Uani 1 1 d . . . H26A H 0.1800 0.0969 0.9640 0.033 Uiso 1 1 calc R . . H26B H 0.1382 0.0468 0.8595 0.033 Uiso 1 1 calc R . . H26C H 0.3235 0.1291 0.8962 0.033 Uiso 1 1 calc R . . C27 C 0.4194(3) 0.4628(2) 0.47450(14) 0.0263(5) Uani 1 1 d . . . H27A H 0.4332 0.3916 0.4374 0.032 Uiso 1 1 calc R . . H27B H 0.3827 0.5113 0.4344 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.26716(7) 0.41445(6) 0.55350(4) 0.03300(16) 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 S1 0.0211(3) 0.0127(3) 0.0234(3) 0.0038(2) 0.0002(2) -0.0030(2) P1 0.0115(3) 0.0113(3) 0.0128(3) 0.00139(19) -0.00096(19) 0.0006(2) C1 0.0112(9) 0.0120(11) 0.0147(10) 0.0019(7) -0.0003(7) 0.0060(9) C2 0.0133(10) 0.0147(12) 0.0174(10) 0.0032(8) 0.0022(8) 0.0048(9) C3 0.0200(11) 0.0186(12) 0.0142(10) 0.0055(8) 0.0052(8) 0.0093(10) C4 0.0211(11) 0.0160(12) 0.0109(10) 0.0013(8) -0.0005(8) 0.0106(10) C5 0.0155(10) 0.0117(11) 0.0120(10) 0.0002(7) -0.0005(7) 0.0084(9) C6 0.0162(10) 0.0162(12) 0.0119(10) -0.0007(8) -0.0038(7) 0.0095(9) C7 0.0129(10) 0.0131(11) 0.0148(10) -0.0013(8) -0.0027(7) 0.0079(9) C8 0.0125(10) 0.0168(12) 0.0171(10) -0.0021(8) -0.0051(8) 0.0072(9) C9 0.0110(10) 0.0145(12) 0.0223(11) -0.0024(8) -0.0032(8) 0.0037(9) C10 0.0136(10) 0.0129(11) 0.0185(10) 0.0019(8) 0.0024(8) 0.0042(9) C11 0.0125(9) 0.0128(11) 0.0118(9) -0.0004(7) 0.0002(7) 0.0066(9) C12 0.0129(10) 0.0122(11) 0.0122(9) -0.0017(7) -0.0001(7) 0.0080(9) C13 0.0120(9) 0.0129(11) 0.0100(9) -0.0003(7) -0.0009(7) 0.0068(9) C14 0.0128(10) 0.0118(11) 0.0100(9) -0.0006(7) 0.0005(7) 0.0064(9) P13 0.0097(3) 0.0107(3) 0.0099(2) 0.00177(19) -0.00091(18) 0.0025(2) S2 0.0123(3) 0.0171(3) 0.0186(3) 0.0033(2) 0.00183(19) 0.0067(2) O2 0.0139(7) 0.0135(8) 0.0124(7) 0.0003(5) -0.0009(5) 0.0017(6) P11 0.0101(2) 0.0111(3) 0.0112(3) 0.00169(19) 0.00028(18) 0.0027(2) C15 0.0120(10) 0.0183(12) 0.0176(10) 0.0047(8) -0.0021(8) 0.0025(9) C16 0.0185(11) 0.0300(15) 0.0214(12) 0.0023(9) -0.0063(8) 0.0012(11) C17 0.0153(11) 0.0276(14) 0.0229(11) 0.0059(9) 0.0010(8) 0.0088(10) C18 0.0157(10) 0.0124(11) 0.0167(10) 0.0010(8) 0.0027(8) 0.0029(9) C19 0.0292(12) 0.0268(14) 0.0191(11) -0.0039(9) 0.0029(9) 0.0079(11) C20 0.0221(11) 0.0226(13) 0.0271(12) 0.0052(9) 0.0035(9) 0.0111(11) C21 0.0150(10) 0.0132(11) 0.0149(10) 0.0037(8) -0.0005(8) 0.0037(9) C22 0.0214(11) 0.0136(12) 0.0191(11) 0.0010(8) -0.0007(8) 0.0072(10) C23 0.0264(12) 0.0209(13) 0.0175(11) 0.0057(8) -0.0017(8) 0.0091(10) C24 0.0139(10) 0.0226(12) 0.0116(10) 0.0009(8) 0.0017(7) 0.0064(9) C25 0.0181(11) 0.0366(15) 0.0220(12) 0.0078(10) 0.0078(9) 0.0071(11) C26 0.0201(11) 0.0236(13) 0.0232(11) -0.0038(9) 0.0010(8) 0.0115(10) C27 0.0294(13) 0.0275(14) 0.0214(12) -0.0012(9) 0.0009(9) 0.0105(12) Cl1 0.0267(3) 0.0376(4) 0.0256(3) 0.0002(2) 0.0059(2) -0.0010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9812(9) . ? P1 C18 1.8411(19) . ? P1 C15 1.850(2) . ? P1 C1 1.8614(19) . ? C1 C2 1.377(3) . ? C1 C14 1.465(3) . ? C2 C3 1.411(3) . ? C2 H2A 0.9500 . ? C3 C4 1.353(3) . ? C3 H3A 0.9500 . ? C4 C5 1.425(3) . ? C4 H4A 0.9500 . ? C5 C6 1.396(3) . ? C5 C14 1.454(3) . ? C6 C7 1.383(3) . ? C6 H6A 0.9500 . ? C7 C8 1.429(3) . ? C7 C12 1.431(3) . ? C8 C9 1.360(3) . ? C8 H8A 0.9500 . ? C9 C10 1.411(3) . ? C9 H9A 0.9500 . ? C10 C11 1.369(3) . ? C10 H10A 0.9500 . ? C11 C12 1.446(3) . ? C11 P11 1.7791(19) . ? C12 C13 1.423(3) . ? C13 C14 1.433(3) . ? C13 P13 1.8598(18) . ? P13 O2 1.4946(14) . ? P13 S2 1.9575(8) . ? P13 P11 2.2272(9) . ? P11 C21 1.827(2) . ? P11 C24 1.8303(19) . ? C15 C16 1.535(3) . ? C15 C17 1.536(3) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.526(3) . ? C18 C20 1.529(3) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.531(3) . ? C21 C23 1.538(3) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.530(3) . ? C24 C26 1.534(3) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C27 1.495(4) 2_666 ? C27 Cl1 1.794(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 P1 C15 115.72(9) . . ? C18 P1 C1 103.88(9) . . ? C15 P1 C1 108.44(9) . . ? C18 P1 S1 109.00(7) . . ? C15 P1 S1 108.80(8) . . ? C1 P1 S1 110.93(7) . . ? C2 C1 C14 118.86(17) . . ? C2 C1 P1 110.02(15) . . ? C14 C1 P1 129.61(14) . . ? C1 C2 C3 124.13(19) . . ? C1 C2 H2A 117.9 . . ? C3 C2 H2A 117.9 . . ? C4 C3 C2 118.30(18) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C3 C4 C5 120.66(18) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 116.94(17) . . ? C6 C5 C14 121.25(18) . . ? C4 C5 C14 121.72(18) . . ? C7 C6 C5 122.08(17) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C8 121.89(17) . . ? C6 C7 C12 117.89(18) . . ? C8 C7 C12 119.93(18) . . ? C9 C8 C7 121.59(18) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C8 C9 C10 119.57(18) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 120.56(19) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 122.23(17) . . ? C10 C11 P11 123.48(16) . . ? C12 C11 P11 114.22(14) . . ? C13 C12 C7 121.50(18) . . ? C13 C12 C11 122.51(16) . . ? C7 C12 C11 115.94(17) . . ? C12 C13 C14 119.92(16) . . ? C12 C13 P13 113.12(14) . . ? C14 C13 P13 125.37(14) . . ? C13 C14 C5 116.40(17) . . ? C13 C14 C1 128.96(16) . . ? C5 C14 C1 114.61(17) . . ? O2 P13 C13 117.10(8) . . ? O2 P13 S2 120.72(6) . . ? C13 P13 S2 108.11(6) . . ? O2 P13 P11 102.76(6) . . ? C13 P13 P11 92.90(7) . . ? S2 P13 P11 111.39(4) . . ? C11 P11 C21 112.48(9) . . ? C11 P11 C24 110.57(9) . . ? C21 P11 C24 109.96(9) . . ? C11 P11 P13 95.81(7) . . ? C21 P11 P13 117.04(7) . . ? C24 P11 P13 110.25(7) . . ? C16 C15 C17 109.89(17) . . ? C16 C15 P1 112.02(15) . . ? C17 C15 P1 108.48(13) . . ? C16 C15 H15A 108.8 . . ? C17 C15 H15A 108.8 . . ? P1 C15 H15A 108.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 110.37(17) . . ? C19 C18 P1 111.75(14) . . ? C20 C18 P1 108.65(14) . . ? C19 C18 H18A 108.7 . . ? C20 C18 H18A 108.7 . . ? P1 C18 H18A 108.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C23 112.28(16) . . ? C22 C21 P11 113.21(14) . . ? C23 C21 P11 108.92(14) . . ? C22 C21 H21A 107.4 . . ? C23 C21 H21A 107.4 . . ? P11 C21 H21A 107.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C26 111.64(17) . . ? C25 C24 P11 112.52(15) . . ? C26 C24 P11 109.82(14) . . ? C25 C24 H24A 107.5 . . ? C26 C24 H24A 107.5 . . ? P11 C24 H24A 107.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C27 C27 Cl1 108.2(2) 2_666 . ? C27 C27 H27A 110.1 2_666 . ? Cl1 C27 H27A 110.1 . . ? C27 C27 H27B 110.1 2_666 . ? Cl1 C27 H27B 110.1 . . ? H27A C27 H27B 108.4 . . ? 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 C18 P1 C1 C2 134.06(14) . . . . ? C15 P1 C1 C2 -102.34(14) . . . . ? S1 P1 C1 C2 17.08(14) . . . . ? C18 P1 C1 C14 -31.50(19) . . . . ? C15 P1 C1 C14 92.11(18) . . . . ? S1 P1 C1 C14 -148.47(15) . . . . ? C14 C1 C2 C3 5.7(3) . . . . ? P1 C1 C2 C3 -161.67(15) . . . . ? C1 C2 C3 C4 5.8(3) . . . . ? C2 C3 C4 C5 -8.2(3) . . . . ? C3 C4 C5 C6 -177.27(17) . . . . ? C3 C4 C5 C14 -0.7(3) . . . . ? C4 C5 C6 C7 174.09(16) . . . . ? C14 C5 C6 C7 -2.5(3) . . . . ? C5 C6 C7 C8 -179.37(17) . . . . ? C5 C6 C7 C12 -5.6(3) . . . . ? C6 C7 C8 C9 174.97(18) . . . . ? C12 C7 C8 C9 1.3(3) . . . . ? C7 C8 C9 C10 -3.4(3) . . . . ? C8 C9 C10 C11 1.6(3) . . . . ? C9 C10 C11 C12 2.4(3) . . . . ? C9 C10 C11 P11 -174.38(14) . . . . ? C6 C7 C12 C13 6.1(3) . . . . ? C8 C7 C12 C13 -179.93(16) . . . . ? C6 C7 C12 C11 -171.43(16) . . . . ? C8 C7 C12 C11 2.5(2) . . . . ? C10 C11 C12 C13 178.09(17) . . . . ? P11 C11 C12 C13 -4.8(2) . . . . ? C10 C11 C12 C7 -4.4(3) . . . . ? P11 C11 C12 C7 172.72(13) . . . . ? C7 C12 C13 C14 1.4(3) . . . . ? C11 C12 C13 C14 178.78(16) . . . . ? C7 C12 C13 P13 -165.03(14) . . . . ? C11 C12 C13 P13 12.4(2) . . . . ? C12 C13 C14 C5 -9.0(2) . . . . ? P13 C13 C14 C5 155.60(14) . . . . ? C12 C13 C14 C1 173.09(17) . . . . ? P13 C13 C14 C1 -22.3(3) . . . . ? C6 C5 C14 C13 9.7(3) . . . . ? C4 C5 C14 C13 -166.64(16) . . . . ? C6 C5 C14 C1 -172.06(16) . . . . ? C4 C5 C14 C1 11.6(2) . . . . ? C2 C1 C14 C13 164.28(18) . . . . ? P1 C1 C14 C13 -31.2(3) . . . . ? C2 C1 C14 C5 -13.6(2) . . . . ? P1 C1 C14 C5 150.84(14) . . . . ? C12 C13 P13 O2 -117.50(13) . . . . ? C14 C13 P13 O2 76.97(17) . . . . ? C12 C13 P13 S2 102.05(13) . . . . ? C14 C13 P13 S2 -63.48(16) . . . . ? C12 C13 P13 P11 -11.58(13) . . . . ? C14 C13 P13 P11 -177.10(15) . . . . ? C10 C11 P11 C21 51.04(18) . . . . ? C12 C11 P11 C21 -126.00(14) . . . . ? C10 C11 P11 C24 -72.31(18) . . . . ? C12 C11 P11 C24 110.65(14) . . . . ? C10 C11 P11 P13 173.50(15) . . . . ? C12 C11 P11 P13 -3.55(13) . . . . ? O2 P13 P11 C11 126.55(8) . . . . ? C13 P13 P11 C11 7.92(8) . . . . ? S2 P13 P11 C11 -102.82(7) . . . . ? O2 P13 P11 C21 -114.55(9) . . . . ? C13 P13 P11 C21 126.83(9) . . . . ? S2 P13 P11 C21 16.09(8) . . . . ? O2 P13 P11 C24 12.09(9) . . . . ? C13 P13 P11 C24 -106.54(9) . . . . ? S2 P13 P11 C24 142.72(7) . . . . ? C18 P1 C15 C16 -75.36(18) . . . . ? C1 P1 C15 C16 168.46(15) . . . . ? S1 P1 C15 C16 47.70(16) . . . . ? C18 P1 C15 C17 163.17(14) . . . . ? C1 P1 C15 C17 46.99(17) . . . . ? S1 P1 C15 C17 -73.76(15) . . . . ? C15 P1 C18 C19 58.09(19) . . . . ? C1 P1 C18 C19 176.81(15) . . . . ? S1 P1 C18 C19 -64.87(16) . . . . ? C15 P1 C18 C20 -179.89(14) . . . . ? C1 P1 C18 C20 -61.17(16) . . . . ? S1 P1 C18 C20 57.15(15) . . . . ? C11 P11 C21 C22 44.94(17) . . . . ? C24 P11 C21 C22 168.64(14) . . . . ? P13 P11 C21 C22 -64.58(15) . . . . ? C11 P11 C21 C23 170.61(13) . . . . ? C24 P11 C21 C23 -65.69(16) . . . . ? P13 P11 C21 C23 61.09(14) . . . . ? C11 P11 C24 C25 82.11(16) . . . . ? C21 P11 C24 C25 -42.69(16) . . . . ? P13 P11 C24 C25 -173.19(12) . . . . ? C11 P11 C24 C26 -42.91(17) . . . . ? C21 P11 C24 C26 -167.71(14) . . . . ? P13 P11 C24 C26 61.79(15) . . . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.290 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.055 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 635699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H35 O P3 Se2' _chemical_formula_sum 'C26 H35 O P3 Se2' _chemical_formula_weight 614.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8828(14) _cell_length_b 21.658(3) _cell_length_c 14.892(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.566(4) _cell_angle_gamma 90.00 _cell_volume 2746.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 10301 _cell_measurement_theta_min 1.7083 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 2.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7291 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17349 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4935 _reflns_number_gt 4544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+1.4841P] 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 4935 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Se1 Se 0.64869(3) -0.283718(12) 0.18604(2) 0.03246(9) Uani 1 1 d . . . P1 P 0.70338(7) -0.19084(3) 0.23130(4) 0.02090(14) Uani 1 1 d . . . C1 C 0.6133(3) -0.13552(11) 0.13541(17) 0.0242(5) Uani 1 1 d . . . C2 C 0.4920(3) -0.16246(13) 0.06854(18) 0.0315(6) Uani 1 1 d . . . H2A H 0.4425 -0.1976 0.0857 0.038 Uiso 1 1 calc R . . C3 C 0.4366(3) -0.14054(14) -0.0248(2) 0.0385(7) Uani 1 1 d . . . H3A H 0.3454 -0.1579 -0.0671 0.046 Uiso 1 1 calc R . . C4 C 0.5156(3) -0.09480(13) -0.05238(18) 0.0352(7) Uani 1 1 d . . . H4A H 0.4895 -0.0840 -0.1168 0.042 Uiso 1 1 calc R . . C5 C 0.6381(3) -0.06220(12) 0.01363(17) 0.0273(6) Uani 1 1 d . . . C6 C 0.7119(3) -0.01439(12) -0.01902(17) 0.0307(6) Uani 1 1 d . . . H6A H 0.6844 -0.0065 -0.0845 0.037 Uiso 1 1 calc R . . C7 C 0.8243(3) 0.02223(12) 0.04070(17) 0.0274(6) Uani 1 1 d . . . C8 C 0.9065(3) 0.06968(13) 0.00747(18) 0.0343(7) Uani 1 1 d . . . H8A H 0.8885 0.0749 -0.0581 0.041 Uiso 1 1 calc R . . C9 C 1.0092(4) 0.10733(13) 0.0671(2) 0.0367(7) Uani 1 1 d . . . H9A H 1.0653 0.1376 0.0435 0.044 Uiso 1 1 calc R . . C10 C 1.0331(3) 0.10150(12) 0.16496(19) 0.0305(6) Uani 1 1 d . . . H10A H 1.1042 0.1284 0.2068 0.037 Uiso 1 1 calc R . . C11 C 0.9544(3) 0.05731(11) 0.19954(16) 0.0234(5) Uani 1 1 d . . . C12 C 0.8515(3) 0.01384(11) 0.13927(16) 0.0215(5) Uani 1 1 d . . . C13 C 0.7752(3) -0.03426(11) 0.17494(15) 0.0188(5) Uani 1 1 d . . . C14 C 0.6784(3) -0.07760(11) 0.11263(16) 0.0219(5) Uani 1 1 d . . . P11 P 0.95375(7) 0.05336(3) 0.31892(4) 0.01904(14) Uani 1 1 d . . . P13 P 0.77663(7) -0.02220(3) 0.29807(4) 0.01805(14) Uani 1 1 d . . . Se2 Se 0.55492(3) 0.009394(13) 0.299367(19) 0.02979(9) Uani 1 1 d . . . O2 O 0.85889(19) -0.06943(7) 0.36798(11) 0.0229(4) Uani 1 1 d . . . C15 C 0.6300(3) -0.17594(12) 0.33344(18) 0.0296(6) Uani 1 1 d . . . H15A H 0.6733 -0.1354 0.3613 0.036 Uiso 1 1 calc R . . C16 C 0.6805(5) -0.22523(17) 0.4093(2) 0.0571(10) Uani 1 1 d . . . H16A H 0.6391 -0.2149 0.4618 0.086 Uiso 1 1 calc R . . H16B H 0.7955 -0.2270 0.4313 0.086 Uiso 1 1 calc R . . H16C H 0.6394 -0.2655 0.3834 0.086 Uiso 1 1 calc R . . C17 C 0.4516(4) -0.17078(17) 0.3004(2) 0.0510(9) Uani 1 1 d . . . H17A H 0.4118 -0.1627 0.3542 0.076 Uiso 1 1 calc R . . H17B H 0.4069 -0.2095 0.2703 0.076 Uiso 1 1 calc R . . H17C H 0.4213 -0.1368 0.2553 0.076 Uiso 1 1 calc R . . C18 C 0.9151(3) -0.17773(11) 0.25185(17) 0.0236(5) Uani 1 1 d . . . H18A H 0.9371 -0.1333 0.2688 0.028 Uiso 1 1 calc R . . C19 C 1.0151(3) -0.21695(12) 0.33227(19) 0.0323(6) Uani 1 1 d . . . H19A H 1.1265 -0.2083 0.3407 0.048 Uiso 1 1 calc R . . H19B H 0.9943 -0.2608 0.3176 0.048 Uiso 1 1 calc R . . H19C H 0.9884 -0.2069 0.3901 0.048 Uiso 1 1 calc R . . C20 C 0.9611(3) -0.19017(14) 0.16147(19) 0.0363(7) Uani 1 1 d . . . H20A H 1.0738 -0.1829 0.1729 0.054 Uiso 1 1 calc R . . H20B H 0.9020 -0.1625 0.1119 0.054 Uiso 1 1 calc R . . H20C H 0.9367 -0.2331 0.1421 0.054 Uiso 1 1 calc R . . C21 C 0.9019(3) 0.12871(11) 0.35701(17) 0.0258(5) Uani 1 1 d . . . H21A H 0.9967 0.1557 0.3683 0.031 Uiso 1 1 calc R . . C22 C 0.7687(3) 0.16025(12) 0.28268(18) 0.0293(6) Uani 1 1 d . . . H22A H 0.7458 0.2004 0.3062 0.044 Uiso 1 1 calc R . . H22B H 0.6746 0.1343 0.2688 0.044 Uiso 1 1 calc R . . H22C H 0.8006 0.1663 0.2255 0.044 Uiso 1 1 calc R . . C23 C 0.8630(4) 0.12217(13) 0.45016(18) 0.0370(7) Uani 1 1 d . . . H23A H 0.8356 0.1627 0.4702 0.055 Uiso 1 1 calc R . . H23B H 0.9545 0.1057 0.4977 0.055 Uiso 1 1 calc R . . H23C H 0.7740 0.0939 0.4423 0.055 Uiso 1 1 calc R . . C24 C 1.1379(3) 0.02539(11) 0.39867(17) 0.0245(5) Uani 1 1 d . . . H24A H 1.1142 0.0106 0.4568 0.029 Uiso 1 1 calc R . . C25 C 1.2632(3) 0.07568(12) 0.42774(19) 0.0320(6) Uani 1 1 d . . . H25A H 1.3588 0.0581 0.4703 0.048 Uiso 1 1 calc R . . H25B H 1.2243 0.1091 0.4596 0.048 Uiso 1 1 calc R . . H25C H 1.2869 0.0921 0.3720 0.048 Uiso 1 1 calc R . . C26 C 1.1989(3) -0.02991(13) 0.3559(2) 0.0351(6) Uani 1 1 d . . . H26A H 1.2972 -0.0445 0.3994 0.053 Uiso 1 1 calc R . . H26B H 1.2178 -0.0176 0.2967 0.053 Uiso 1 1 calc R . . H26C H 1.1207 -0.0631 0.3440 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 Se1 0.03916(18) 0.01709(15) 0.03884(16) -0.00693(10) 0.00742(13) -0.00409(11) P1 0.0234(3) 0.0168(3) 0.0234(3) -0.0027(2) 0.0081(3) -0.0013(2) C1 0.0231(12) 0.0212(13) 0.0273(12) -0.0036(10) 0.0056(11) 0.0043(10) C2 0.0258(14) 0.0282(15) 0.0350(14) -0.0070(11) 0.0000(12) 0.0006(11) C3 0.0351(16) 0.0339(16) 0.0359(15) -0.0081(12) -0.0068(13) 0.0073(13) C4 0.0421(16) 0.0321(16) 0.0230(13) -0.0041(11) -0.0043(12) 0.0118(13) C5 0.0318(14) 0.0260(14) 0.0223(12) -0.0006(10) 0.0046(11) 0.0127(11) C6 0.0439(17) 0.0304(15) 0.0180(12) 0.0035(10) 0.0091(12) 0.0114(12) C7 0.0378(15) 0.0233(14) 0.0249(12) 0.0062(10) 0.0152(12) 0.0120(11) C8 0.0522(18) 0.0300(15) 0.0283(13) 0.0109(11) 0.0238(13) 0.0103(13) C9 0.0524(18) 0.0261(15) 0.0423(16) 0.0098(12) 0.0309(15) 0.0020(13) C10 0.0367(15) 0.0242(14) 0.0354(14) 0.0044(11) 0.0179(12) -0.0006(12) C11 0.0285(13) 0.0191(13) 0.0263(12) 0.0051(9) 0.0136(11) 0.0026(10) C12 0.0248(13) 0.0194(13) 0.0226(12) 0.0038(9) 0.0105(11) 0.0064(10) C13 0.0199(12) 0.0172(12) 0.0201(11) 0.0001(9) 0.0070(10) 0.0046(9) C14 0.0228(12) 0.0224(13) 0.0199(11) -0.0016(9) 0.0052(10) 0.0088(10) P11 0.0221(3) 0.0139(3) 0.0216(3) 0.0013(2) 0.0069(3) -0.0007(2) P13 0.0217(3) 0.0159(3) 0.0178(3) -0.0006(2) 0.0076(2) -0.0013(2) Se2 0.02401(15) 0.03349(17) 0.03515(16) -0.00362(11) 0.01372(12) 0.00139(11) O2 0.0300(9) 0.0184(9) 0.0188(8) 0.0034(6) 0.0043(7) -0.0044(7) C15 0.0360(15) 0.0259(14) 0.0339(14) -0.0084(11) 0.0212(12) -0.0117(12) C16 0.082(3) 0.058(2) 0.0432(18) 0.0106(16) 0.0381(19) -0.006(2) C17 0.0424(18) 0.054(2) 0.068(2) -0.0203(17) 0.0346(17) -0.0119(16) C18 0.0230(13) 0.0163(12) 0.0320(13) -0.0024(10) 0.0084(11) 0.0003(10) C19 0.0305(15) 0.0296(16) 0.0332(14) 0.0006(11) 0.0033(13) 0.0023(11) C20 0.0351(16) 0.0419(18) 0.0378(15) 0.0095(13) 0.0198(13) 0.0131(13) C21 0.0287(13) 0.0163(12) 0.0283(13) -0.0020(10) 0.0016(11) 0.0014(10) C22 0.0320(14) 0.0214(13) 0.0315(13) 0.0027(10) 0.0042(12) 0.0042(11) C23 0.0490(18) 0.0342(16) 0.0242(13) -0.0060(11) 0.0048(13) 0.0133(14) C24 0.0236(13) 0.0214(13) 0.0297(13) 0.0074(10) 0.0097(11) 0.0011(10) C25 0.0273(14) 0.0258(14) 0.0395(15) 0.0034(11) 0.0040(12) -0.0035(11) C26 0.0270(14) 0.0267(15) 0.0533(17) -0.0005(13) 0.0140(13) 0.0022(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.1332(7) . ? P1 C18 1.839(2) . ? P1 C15 1.846(3) . ? P1 C1 1.861(3) . ? C1 C2 1.372(3) . ? C1 C14 1.461(4) . ? C2 C3 1.418(4) . ? C2 H2A 0.9500 . ? C3 C4 1.344(4) . ? C3 H3A 0.9500 . ? C4 C5 1.428(4) . ? C4 H4A 0.9500 . ? C5 C6 1.386(4) . ? C5 C14 1.453(3) . ? C6 C7 1.382(4) . ? C6 H6A 0.9500 . ? C7 C8 1.428(4) . ? C7 C12 1.430(3) . ? C8 C9 1.351(4) . ? C8 H8A 0.9500 . ? C9 C10 1.417(4) . ? C9 H9A 0.9500 . ? C10 C11 1.369(3) . ? C10 H10A 0.9500 . ? C11 C12 1.435(3) . ? C11 P11 1.782(2) . ? C12 C13 1.426(3) . ? C13 C14 1.423(3) . ? C13 P13 1.849(2) . ? P11 C21 1.829(2) . ? P11 C24 1.829(2) . ? P11 P13 2.2297(9) . ? P13 O2 1.4935(17) . ? P13 Se2 2.0901(7) . ? C15 C17 1.524(4) . ? C15 C16 1.526(4) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.529(3) . ? C18 C20 1.538(3) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C23 1.529(4) . ? C21 C22 1.531(3) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.527(4) . ? C24 C25 1.529(4) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 P1 C15 114.85(11) . . ? C18 P1 C1 102.94(11) . . ? C15 P1 C1 110.13(12) . . ? C18 P1 Se1 109.16(8) . . ? C15 P1 Se1 108.85(9) . . ? C1 P1 Se1 110.81(8) . . ? C2 C1 C14 118.5(2) . . ? C2 C1 P1 111.1(2) . . ? C14 C1 P1 128.21(18) . . ? C1 C2 C3 123.4(3) . . ? C1 C2 H2A 118.3 . . ? C3 C2 H2A 118.3 . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 C14 121.5(2) . . ? C4 C5 C14 120.3(2) . . ? C7 C6 C5 122.0(2) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C8 122.5(2) . . ? C6 C7 C12 117.9(2) . . ? C8 C7 C12 119.6(2) . . ? C9 C8 C7 121.5(2) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 121.7(2) . . ? C10 C11 P11 123.8(2) . . ? C12 C11 P11 114.18(17) . . ? C13 C12 C7 121.1(2) . . ? C13 C12 C11 122.2(2) . . ? C7 C12 C11 116.7(2) . . ? C14 C13 C12 120.1(2) . . ? C14 C13 P13 124.89(18) . . ? C12 C13 P13 113.37(17) . . ? C13 C14 C5 116.0(2) . . ? C13 C14 C1 128.3(2) . . ? C5 C14 C1 115.7(2) . . ? C11 P11 C21 109.85(11) . . ? C11 P11 C24 114.01(12) . . ? C21 P11 C24 110.60(11) . . ? C11 P11 P13 95.70(9) . . ? C21 P11 P13 117.89(9) . . ? C24 P11 P13 108.19(8) . . ? O2 P13 C13 117.28(10) . . ? O2 P13 Se2 119.52(7) . . ? C13 P13 Se2 108.38(7) . . ? O2 P13 P11 102.72(7) . . ? C13 P13 P11 92.69(8) . . ? Se2 P13 P11 112.82(3) . . ? C17 C15 C16 110.5(3) . . ? C17 C15 P1 108.99(19) . . ? C16 C15 P1 112.9(2) . . ? C17 C15 H15A 108.1 . . ? C16 C15 H15A 108.1 . . ? P1 C15 H15A 108.1 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 110.4(2) . . ? C19 C18 P1 112.50(18) . . ? C20 C18 P1 109.97(18) . . ? C19 C18 H18A 107.9 . . ? C20 C18 H18A 107.9 . . ? P1 C18 H18A 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C23 C21 C22 111.7(2) . . ? C23 C21 P11 109.93(17) . . ? C22 C21 P11 112.63(17) . . ? C23 C21 H21A 107.4 . . ? C22 C21 H21A 107.4 . . ? P11 C21 H21A 107.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C25 111.1(2) . . ? C26 C24 P11 110.29(18) . . ? C25 C24 P11 113.08(17) . . ? C26 C24 H24A 107.3 . . ? C25 C24 H24A 107.3 . . ? P11 C24 H24A 107.3 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C18 P1 C1 C2 136.6(2) . . . . ? C15 P1 C1 C2 -100.5(2) . . . . ? Se1 P1 C1 C2 20.0(2) . . . . ? C18 P1 C1 C14 -26.3(2) . . . . ? C15 P1 C1 C14 96.6(2) . . . . ? Se1 P1 C1 C14 -142.9(2) . . . . ? C14 C1 C2 C3 6.6(4) . . . . ? P1 C1 C2 C3 -158.1(2) . . . . ? C1 C2 C3 C4 6.6(4) . . . . ? C2 C3 C4 C5 -9.5(4) . . . . ? C3 C4 C5 C6 -178.2(3) . . . . ? C3 C4 C5 C14 -0.7(4) . . . . ? C4 C5 C6 C7 175.7(2) . . . . ? C14 C5 C6 C7 -1.8(4) . . . . ? C5 C6 C7 C8 176.9(2) . . . . ? C5 C6 C7 C12 -6.6(4) . . . . ? C6 C7 C8 C9 176.1(3) . . . . ? C12 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 -2.2(4) . . . . ? C8 C9 C10 C11 1.0(4) . . . . ? C9 C10 C11 C12 2.9(4) . . . . ? C9 C10 C11 P11 -170.4(2) . . . . ? C6 C7 C12 C13 5.3(4) . . . . ? C8 C7 C12 C13 -178.1(2) . . . . ? C6 C7 C12 C11 -172.6(2) . . . . ? C8 C7 C12 C11 4.0(3) . . . . ? C10 C11 C12 C13 176.8(2) . . . . ? P11 C11 C12 C13 -9.3(3) . . . . ? C10 C11 C12 C7 -5.3(4) . . . . ? P11 C11 C12 C7 168.63(18) . . . . ? C7 C12 C13 C14 4.4(3) . . . . ? C11 C12 C13 C14 -177.8(2) . . . . ? C7 C12 C13 P13 -161.86(19) . . . . ? C11 C12 C13 P13 16.0(3) . . . . ? C12 C13 C14 C5 -12.2(3) . . . . ? P13 C13 C14 C5 152.35(18) . . . . ? C12 C13 C14 C1 168.3(2) . . . . ? P13 C13 C14 C1 -27.2(3) . . . . ? C6 C5 C14 C13 11.2(4) . . . . ? C4 C5 C14 C13 -166.2(2) . . . . ? C6 C5 C14 C1 -169.2(2) . . . . ? C4 C5 C14 C1 13.4(3) . . . . ? C2 C1 C14 C13 163.5(2) . . . . ? P1 C1 C14 C13 -34.6(4) . . . . ? C2 C1 C14 C5 -16.0(3) . . . . ? P1 C1 C14 C5 145.8(2) . . . . ? C10 C11 P11 C21 50.7(3) . . . . ? C12 C11 P11 C21 -123.06(19) . . . . ? C10 C11 P11 C24 -74.1(2) . . . . ? C12 C11 P11 C24 112.16(19) . . . . ? C10 C11 P11 P13 173.1(2) . . . . ? C12 C11 P11 P13 -0.66(18) . . . . ? C14 C13 P13 O2 76.1(2) . . . . ? C12 C13 P13 O2 -118.42(17) . . . . ? C14 C13 P13 Se2 -63.0(2) . . . . ? C12 C13 P13 Se2 102.50(17) . . . . ? C14 C13 P13 P11 -178.10(19) . . . . ? C12 C13 P13 P11 -12.63(17) . . . . ? C11 P11 P13 O2 125.70(11) . . . . ? C21 P11 P13 O2 -118.27(11) . . . . ? C24 P11 P13 O2 8.11(12) . . . . ? C11 P11 P13 C13 6.95(11) . . . . ? C21 P11 P13 C13 122.98(11) . . . . ? C24 P11 P13 C13 -110.64(11) . . . . ? C11 P11 P13 Se2 -104.29(8) . . . . ? C21 P11 P13 Se2 11.75(10) . . . . ? C24 P11 P13 Se2 138.12(9) . . . . ? C18 P1 C15 C17 164.22(19) . . . . ? C1 P1 C15 C17 48.6(2) . . . . ? Se1 P1 C15 C17 -73.1(2) . . . . ? C18 P1 C15 C16 -72.6(2) . . . . ? C1 P1 C15 C16 171.7(2) . . . . ? Se1 P1 C15 C16 50.1(2) . . . . ? C15 P1 C18 C19 57.8(2) . . . . ? C1 P1 C18 C19 177.54(18) . . . . ? Se1 P1 C18 C19 -64.71(19) . . . . ? C15 P1 C18 C20 -178.71(18) . . . . ? C1 P1 C18 C20 -59.00(19) . . . . ? Se1 P1 C18 C20 58.76(18) . . . . ? C11 P11 C21 C23 166.59(18) . . . . ? C24 P11 C21 C23 -66.7(2) . . . . ? P13 P11 C21 C23 58.5(2) . . . . ? C11 P11 C21 C22 41.4(2) . . . . ? C24 P11 C21 C22 168.07(18) . . . . ? P13 P11 C21 C22 -66.7(2) . . . . ? C11 P11 C24 C26 -43.4(2) . . . . ? C21 P11 C24 C26 -167.75(18) . . . . ? P13 P11 C24 C26 61.74(19) . . . . ? C11 P11 C24 C25 81.8(2) . . . . ? C21 P11 C24 C25 -42.6(2) . . . . ? P13 P11 C24 C25 -173.13(17) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.558 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.065 data_12 _database_code_depnum_ccdc_archive 'CCDC 635700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H35 Cl P3. I3 ' _chemical_formula_sum 'C26 H35 Cl I3 P3' _chemical_formula_weight 856.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 11.026(2) _cell_length_b 11.026(2) _cell_length_c 25.560(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3107.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 12601 _cell_measurement_theta_min 2.0123 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.0300 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 3.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6812 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19345 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.33 _reflns_number_total 5115 _reflns_number_gt 4920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Poor crystal quality and heavy absorption resulted in restrained refinement being needed, with l C2, C4, C6, C12, C13 and C19 being refined isotropically and a default 'DELU' instruction being used, leading to 61 restraints with the 62nd restrint being GOOF. ; _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^)+(0.0441P)^2^+64.7989P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 5115 _refine_ls_number_parameters 269 _refine_ls_number_restraints 62 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.13638(10) -0.27606(10) -0.20881(4) 0.0381(3) Uani 1 1 d U . . I2 I -0.31168(8) -0.08817(8) -0.22738(3) 0.01979(19) Uani 1 1 d U . . I3 I -0.48524(9) 0.10593(10) -0.24813(4) 0.0329(3) Uani 1 1 d U . . Cl13 Cl 0.2961(3) 0.2899(3) -0.19915(14) 0.0245(7) Uani 1 1 d U . . P1 P 0.0092(3) 0.2627(3) -0.18208(13) 0.0144(7) Uani 1 1 d U . . P11 P 0.3224(3) 0.5777(3) -0.17353(14) 0.0188(7) Uani 1 1 d U . . P13 P 0.1630(3) 0.4128(3) -0.17266(13) 0.0156(7) Uani 1 1 d U . . C1 C -0.0600(10) 0.3248(11) -0.2395(5) 0.012(2) Uani 1 1 d U . . C2 C -0.1564(11) 0.2792(12) -0.2652(5) 0.015(3) Uiso 1 1 d U . . H2A H -0.1933 0.2076 -0.2520 0.018 Uiso 1 1 calc R . . C3 C -0.2044(13) 0.3317(15) -0.3100(5) 0.028(3) Uani 1 1 d U . . H3A H -0.2755 0.2995 -0.3258 0.033 Uiso 1 1 calc R . . C4 C -0.1475(12) 0.4310(12) -0.3313(5) 0.018(3) Uiso 1 1 d U . . H4A H -0.1781 0.4649 -0.3628 0.021 Uiso 1 1 calc R . . C5 C -0.0406(11) 0.4863(12) -0.3066(5) 0.016(2) Uani 1 1 d U . . C6 C 0.0154(12) 0.5842(12) -0.3283(5) 0.017(3) Uiso 1 1 d U . . H6A H -0.0116 0.6148 -0.3610 0.020 Uiso 1 1 calc R . . C7 C 0.1116(12) 0.6394(11) -0.3028(5) 0.016(2) Uani 1 1 d U . . C8 C 0.1686(12) 0.7444(12) -0.3248(5) 0.019(3) Uani 1 1 d U . . H8A H 0.1351 0.7784 -0.3557 0.023 Uiso 1 1 calc R . . C9 C 0.2690(13) 0.7980(14) -0.3035(6) 0.026(3) Uani 1 1 d U . . H9A H 0.3063 0.8661 -0.3196 0.031 Uiso 1 1 calc R . . C10 C 0.3157(12) 0.7478(12) -0.2560(5) 0.018(3) Uani 1 1 d U . . H10A H 0.3839 0.7849 -0.2399 0.022 Uiso 1 1 calc R . . C11 C 0.2631(11) 0.6442(12) -0.2323(5) 0.017(2) Uani 1 1 d U . . C12 C 0.1611(10) 0.5857(10) -0.2554(5) 0.011(2) Uiso 1 1 d U . . C13 C 0.1128(10) 0.4792(10) -0.2321(5) 0.012(2) Uiso 1 1 d U . . C14 C 0.0036(11) 0.4301(11) -0.2593(5) 0.015(2) Uani 1 1 d U . . C15 C -0.0905(13) 0.2910(12) -0.1261(5) 0.020(3) Uani 1 1 d U . . H15A H -0.0421 0.2739 -0.0938 0.024 Uiso 1 1 calc R . . C16 C -0.1258(15) 0.4230(14) -0.1240(6) 0.030(3) Uani 1 1 d U . . H16A H -0.1788 0.4370 -0.0938 0.045 Uiso 1 1 calc R . . H16B H -0.1688 0.4449 -0.1562 0.045 Uiso 1 1 calc R . . H16C H -0.0527 0.4730 -0.1206 0.045 Uiso 1 1 calc R . . C17 C -0.2043(16) 0.2072(16) -0.1241(7) 0.040(4) Uani 1 1 d U . . H17A H -0.2528 0.2269 -0.0931 0.059 Uiso 1 1 calc R . . H17B H -0.1784 0.1223 -0.1224 0.059 Uiso 1 1 calc R . . H17C H -0.2532 0.2197 -0.1557 0.059 Uiso 1 1 calc R . . C18 C 0.0177(14) 0.1001(12) -0.1905(6) 0.027(3) Uani 1 1 d U . . H18A H -0.0675 0.0691 -0.1919 0.032 Uiso 1 1 calc R . . C19 C 0.0824(14) 0.0529(14) -0.2382(6) 0.032(4) Uiso 1 1 d U . . H19A H 0.0817 -0.0360 -0.2377 0.048 Uiso 1 1 calc R . . H19B H 0.1664 0.0819 -0.2381 0.048 Uiso 1 1 calc R . . H19C H 0.0411 0.0820 -0.2697 0.048 Uiso 1 1 calc R . . C20 C 0.0787(18) 0.0423(15) -0.1413(7) 0.042(4) Uani 1 1 d U . . H20A H 0.0828 -0.0459 -0.1457 0.063 Uiso 1 1 calc R . . H20B H 0.0307 0.0616 -0.1101 0.063 Uiso 1 1 calc R . . H20C H 0.1609 0.0749 -0.1373 0.063 Uiso 1 1 calc R . . C21 C 0.2806(13) 0.6801(13) -0.1197(6) 0.024(3) Uani 1 1 d U . . H21A H 0.3005 0.6380 -0.0861 0.028 Uiso 1 1 calc R . . C22 C 0.1425(14) 0.7014(14) -0.1207(6) 0.031(3) Uani 1 1 d U . . H22A H 0.1196 0.7552 -0.0918 0.046 Uiso 1 1 calc R . . H22B H 0.1004 0.6236 -0.1169 0.046 Uiso 1 1 calc R . . H22C H 0.1197 0.7389 -0.1541 0.046 Uiso 1 1 calc R . . C23 C 0.3484(17) 0.8025(15) -0.1199(7) 0.042(4) Uani 1 1 d U . . H23A H 0.3215 0.8516 -0.0901 0.063 Uiso 1 1 calc R . . H23B H 0.3309 0.8458 -0.1525 0.063 Uiso 1 1 calc R . . H23C H 0.4358 0.7880 -0.1172 0.063 Uiso 1 1 calc R . . C24 C 0.4880(13) 0.5865(15) -0.1767(6) 0.029(3) Uani 1 1 d U . . H24A H 0.5136 0.6727 -0.1818 0.035 Uiso 1 1 calc R . . C25 C 0.5393(16) 0.507(2) -0.2218(8) 0.065(7) Uani 1 1 d U . . H25A H 0.6277 0.5152 -0.2232 0.098 Uiso 1 1 calc R . . H25B H 0.5041 0.5328 -0.2551 0.098 Uiso 1 1 calc R . . H25C H 0.5183 0.4215 -0.2154 0.098 Uiso 1 1 calc R . . C26 C 0.5418(16) 0.5367(19) -0.1232(8) 0.050(5) Uani 1 1 d U . . H26A H 0.6304 0.5429 -0.1239 0.074 Uiso 1 1 calc R . . H26B H 0.5182 0.4516 -0.1187 0.074 Uiso 1 1 calc R . . H26C H 0.5098 0.5848 -0.0941 0.074 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 I1 0.0490(7) 0.0441(6) 0.0212(5) -0.0006(4) 0.0048(5) 0.0314(5) I2 0.0225(4) 0.0232(4) 0.0137(4) -0.0038(3) -0.0010(3) 0.0051(4) I3 0.0307(5) 0.0350(6) 0.0331(6) -0.0037(4) -0.0062(4) 0.0179(4) Cl13 0.0162(15) 0.0220(16) 0.035(2) 0.0045(14) -0.0063(14) 0.0034(12) P1 0.0140(15) 0.0155(16) 0.0137(17) -0.0001(12) -0.0002(13) 0.0023(12) P11 0.0150(16) 0.0211(17) 0.0203(18) 0.0021(14) 0.0002(13) -0.0020(13) P13 0.0131(15) 0.0211(17) 0.0127(16) -0.0007(13) 0.0002(12) 0.0069(13) C1 0.006(5) 0.022(6) 0.008(5) 0.004(4) -0.003(4) 0.000(4) C3 0.019(7) 0.058(10) 0.005(6) 0.003(6) -0.008(5) -0.012(6) C5 0.016(6) 0.018(6) 0.013(6) -0.003(5) -0.001(5) 0.010(4) C7 0.020(6) 0.010(5) 0.017(6) -0.004(5) 0.004(5) 0.012(4) C8 0.022(6) 0.021(7) 0.014(7) 0.007(5) -0.001(5) 0.004(5) C9 0.024(7) 0.033(8) 0.021(7) 0.009(6) 0.000(6) 0.000(5) C10 0.027(7) 0.023(7) 0.004(6) 0.005(4) -0.002(5) -0.003(5) C11 0.015(5) 0.026(6) 0.009(5) 0.001(4) 0.007(4) -0.002(5) C14 0.017(6) 0.016(6) 0.011(6) 0.006(4) 0.009(4) 0.011(5) C15 0.030(7) 0.019(6) 0.010(5) 0.009(5) 0.004(5) -0.002(5) C16 0.034(9) 0.031(7) 0.026(8) 0.003(6) 0.016(6) 0.007(6) C17 0.033(8) 0.048(9) 0.038(10) -0.005(8) 0.021(7) -0.016(7) C18 0.034(8) 0.012(5) 0.035(8) -0.004(5) -0.017(6) 0.004(5) C20 0.054(11) 0.024(8) 0.048(10) 0.011(7) -0.016(8) 0.012(7) C21 0.029(6) 0.024(6) 0.018(6) -0.005(5) -0.015(5) -0.002(5) C22 0.032(6) 0.029(8) 0.032(9) -0.009(6) 0.012(6) -0.010(6) C23 0.054(10) 0.033(8) 0.040(10) -0.006(7) -0.003(8) -0.023(8) C24 0.018(5) 0.044(9) 0.026(8) 0.019(6) 0.007(5) -0.005(5) C25 0.029(8) 0.113(18) 0.055(10) -0.014(11) -0.025(8) 0.043(11) C26 0.029(9) 0.065(13) 0.054(9) -0.004(9) -0.027(8) 0.008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.8729(14) . ? I2 I3 2.9196(14) . ? Cl13 P13 2.109(5) . ? P1 C1 1.791(11) . ? P1 C18 1.808(13) . ? P1 C15 1.832(13) . ? P1 P13 2.382(5) . ? P11 C11 1.794(13) . ? P11 C24 1.831(14) . ? P11 C21 1.840(14) . ? P11 P13 2.528(5) . ? P13 C13 1.775(12) . ? C1 C2 1.346(17) . ? C1 C14 1.448(17) . ? C2 C3 1.390(19) . ? C2 H2A 0.9500 . ? C3 C4 1.37(2) . ? C3 H3A 0.9500 . ? C4 C5 1.470(18) . ? C4 H4A 0.9500 . ? C5 C6 1.361(18) . ? C5 C14 1.444(17) . ? C6 C7 1.385(18) . ? C6 H6A 0.9500 . ? C7 C8 1.434(19) . ? C7 C12 1.453(18) . ? C8 C9 1.37(2) . ? C8 H8A 0.9500 . ? C9 C10 1.430(19) . ? C9 H9A 0.9500 . ? C10 C11 1.417(18) . ? C10 H10A 0.9500 . ? C11 C12 1.425(17) . ? C12 C13 1.421(16) . ? C13 C14 1.492(17) . ? C15 C16 1.507(19) . ? C15 C17 1.56(2) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.51(2) . ? C18 C20 1.56(2) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.54(2) . ? C21 C23 1.54(2) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.56(3) . ? C24 C26 1.59(2) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 I2 I3 178.47(5) . . ? C1 P1 C18 107.7(6) . . ? C1 P1 C15 108.7(6) . . ? C18 P1 C15 107.0(7) . . ? C1 P1 P13 96.9(4) . . ? C18 P1 P13 131.6(5) . . ? C15 P1 P13 103.3(5) . . ? C11 P11 C24 107.8(6) . . ? C11 P11 C21 106.5(6) . . ? C24 P11 C21 104.5(7) . . ? C11 P11 P13 92.7(4) . . ? C24 P11 P13 137.1(6) . . ? C21 P11 P13 105.1(5) . . ? C13 P13 Cl13 101.9(4) . . ? C13 P13 P1 88.7(4) . . ? Cl13 P13 P1 90.93(17) . . ? C13 P13 P11 85.0(4) . . ? Cl13 P13 P11 88.60(16) . . ? P1 P13 P11 173.48(19) . . ? C2 C1 C14 120.8(11) . . ? C2 C1 P1 126.4(10) . . ? C14 C1 P1 112.7(8) . . ? C1 C2 C3 123.2(12) . . ? C1 C2 H2A 118.4 . . ? C3 C2 H2A 118.4 . . ? C4 C3 C2 119.0(12) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 121.8(12) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C14 121.9(12) . . ? C6 C5 C4 121.2(12) . . ? C14 C5 C4 116.9(12) . . ? C5 C6 C7 120.2(12) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C8 120.4(12) . . ? C6 C7 C12 120.1(12) . . ? C8 C7 C12 119.4(12) . . ? C9 C8 C7 123.2(12) . . ? C9 C8 H8A 118.4 . . ? C7 C8 H8A 118.4 . . ? C8 C9 C10 117.5(13) . . ? C8 C9 H9A 121.2 . . ? C10 C9 H9A 121.2 . . ? C11 C10 C9 121.9(12) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 C12 120.7(11) . . ? C10 C11 P11 122.6(10) . . ? C12 C11 P11 116.8(9) . . ? C13 C12 C11 119.7(11) . . ? C13 C12 C7 123.0(11) . . ? C11 C12 C7 117.3(11) . . ? C12 C13 C14 114.1(10) . . ? C12 C13 P13 125.6(9) . . ? C14 C13 P13 120.0(9) . . ? C5 C14 C1 118.2(11) . . ? C5 C14 C13 120.4(11) . . ? C1 C14 C13 121.3(10) . . ? C16 C15 C17 111.3(13) . . ? C16 C15 P1 110.3(9) . . ? C17 C15 P1 114.0(10) . . ? C16 C15 H15A 106.9 . . ? C17 C15 H15A 106.9 . . ? P1 C15 H15A 106.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 107.8(13) . . ? C19 C18 P1 117.6(11) . . ? C20 C18 P1 109.4(10) . . ? C19 C18 H18A 107.2 . . ? C20 C18 H18A 107.2 . . ? P1 C18 H18A 107.2 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C23 110.2(12) . . ? C22 C21 P11 109.2(9) . . ? C23 C21 P11 114.4(11) . . ? C22 C21 H21A 107.6 . . ? C23 C21 H21A 107.6 . . ? P11 C21 H21A 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C26 107.8(14) . . ? C25 C24 P11 111.3(12) . . ? C26 C24 P11 108.4(10) . . ? C25 C24 H24A 109.7 . . ? C26 C24 H24A 109.7 . . ? P11 C24 H24A 109.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C1 P1 P13 C13 -4.3(6) . . . . ? C18 P1 P13 C13 116.9(8) . . . . ? C15 P1 P13 C13 -115.4(6) . . . . ? C1 P1 P13 Cl13 -106.2(4) . . . . ? C18 P1 P13 Cl13 15.0(7) . . . . ? C15 P1 P13 Cl13 142.7(5) . . . . ? C1 P1 P13 P11 -20.4(17) . . . . ? C18 P1 P13 P11 100.8(17) . . . . ? C15 P1 P13 P11 -131.5(17) . . . . ? C11 P11 P13 C13 2.3(6) . . . . ? C24 P11 P13 C13 -117.7(8) . . . . ? C21 P11 P13 C13 110.2(6) . . . . ? C11 P11 P13 Cl13 104.4(4) . . . . ? C24 P11 P13 Cl13 -15.6(8) . . . . ? C21 P11 P13 Cl13 -147.7(5) . . . . ? C11 P11 P13 P1 18.5(17) . . . . ? C24 P11 P13 P1 -101.5(18) . . . . ? C21 P11 P13 P1 126.4(17) . . . . ? C18 P1 C1 C2 42.3(13) . . . . ? C15 P1 C1 C2 -73.3(13) . . . . ? P13 P1 C1 C2 -179.9(11) . . . . ? C18 P1 C1 C14 -134.1(10) . . . . ? C15 P1 C1 C14 110.3(9) . . . . ? P13 P1 C1 C14 3.7(9) . . . . ? C14 C1 C2 C3 -3(2) . . . . ? P1 C1 C2 C3 -179.3(11) . . . . ? C1 C2 C3 C4 4(2) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C3 C4 C5 C6 179.5(14) . . . . ? C3 C4 C5 C14 1.2(19) . . . . ? C14 C5 C6 C7 -5.5(19) . . . . ? C4 C5 C6 C7 176.2(12) . . . . ? C5 C6 C7 C8 -178.4(12) . . . . ? C5 C6 C7 C12 6.2(18) . . . . ? C6 C7 C8 C9 -175.4(13) . . . . ? C12 C7 C8 C9 0(2) . . . . ? C7 C8 C9 C10 -2(2) . . . . ? C8 C9 C10 C11 2(2) . . . . ? C9 C10 C11 C12 0(2) . . . . ? C9 C10 C11 P11 178.5(11) . . . . ? C24 P11 C11 C10 -37.8(13) . . . . ? C21 P11 C11 C10 73.9(12) . . . . ? P13 P11 C11 C10 -179.5(11) . . . . ? C24 P11 C11 C12 140.5(10) . . . . ? C21 P11 C11 C12 -107.9(10) . . . . ? P13 P11 C11 C12 -1.3(9) . . . . ? C10 C11 C12 C13 177.5(12) . . . . ? P11 C11 C12 C13 -0.8(15) . . . . ? C10 C11 C12 C7 -2.2(17) . . . . ? P11 C11 C12 C7 179.5(9) . . . . ? C6 C7 C12 C13 -2.2(18) . . . . ? C8 C7 C12 C13 -177.6(11) . . . . ? C6 C7 C12 C11 177.5(11) . . . . ? C8 C7 C12 C11 2.1(17) . . . . ? C11 C12 C13 C14 177.9(11) . . . . ? C7 C12 C13 C14 -2.4(16) . . . . ? C11 C12 C13 P13 3.8(17) . . . . ? C7 C12 C13 P13 -176.5(9) . . . . ? Cl13 P13 C13 C12 -91.1(10) . . . . ? P1 P13 C13 C12 178.2(10) . . . . ? P11 P13 C13 C12 -3.6(10) . . . . ? Cl13 P13 C13 C14 95.1(9) . . . . ? P1 P13 C13 C14 4.4(9) . . . . ? P11 P13 C13 C14 -177.4(9) . . . . ? C6 C5 C14 C1 -178.7(12) . . . . ? C4 C5 C14 C1 -0.4(16) . . . . ? C6 C5 C14 C13 0.7(18) . . . . ? C4 C5 C14 C13 179.1(11) . . . . ? C2 C1 C14 C5 1.3(17) . . . . ? P1 C1 C14 C5 177.9(9) . . . . ? C2 C1 C14 C13 -178.1(12) . . . . ? P1 C1 C14 C13 -1.5(14) . . . . ? C12 C13 C14 C5 3.1(16) . . . . ? P13 C13 C14 C5 177.6(9) . . . . ? C12 C13 C14 C1 -177.5(11) . . . . ? P13 C13 C14 C1 -3.0(15) . . . . ? C1 P1 C15 C16 -50.8(12) . . . . ? C18 P1 C15 C16 -166.9(11) . . . . ? P13 P1 C15 C16 51.3(11) . . . . ? C1 P1 C15 C17 75.3(12) . . . . ? C18 P1 C15 C17 -40.8(13) . . . . ? P13 P1 C15 C17 177.4(10) . . . . ? C1 P1 C18 C19 56.1(12) . . . . ? C15 P1 C18 C19 172.8(11) . . . . ? P13 P1 C18 C19 -60.8(13) . . . . ? C1 P1 C18 C20 179.5(11) . . . . ? C15 P1 C18 C20 -63.8(13) . . . . ? P13 P1 C18 C20 62.6(14) . . . . ? C11 P11 C21 C22 54.2(11) . . . . ? C24 P11 C21 C22 168.1(10) . . . . ? P13 P11 C21 C22 -43.4(11) . . . . ? C11 P11 C21 C23 -69.8(12) . . . . ? C24 P11 C21 C23 44.1(13) . . . . ? P13 P11 C21 C23 -167.4(10) . . . . ? C11 P11 C24 C25 -65.6(14) . . . . ? C21 P11 C24 C25 -178.5(13) . . . . ? P13 P11 C24 C25 49.2(15) . . . . ? C11 P11 C24 C26 176.0(11) . . . . ? C21 P11 C24 C26 63.0(13) . . . . ? P13 P11 C24 C26 -69.3(15) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 2.166 _refine_diff_density_min -1.634 _refine_diff_density_rms 0.224