# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Athanasia Dervisi' _publ_contact_author_address ; Department of Chemistry Cardiff University PO Box 912 Cardiff CF10 3TB UNITED KINGDOM ; _publ_contact_author_email DERVISIA@CARDIFF.AC.UK _publ_section_title ; A concise synthesis of a rigid isomannide-based diphosphine ligand and structural characterisation of an alkoxyphosphonium intermediate ; loop_ _publ_author_name 'Athanasia Dervisi' 'Cristina Carcedo' 'Ian A. Fallis' 'K.M Abdul Malik' data_2 _database_code_depnum_ccdc_archive 'CCDC 230131' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H50 Br2 O7 P2' _chemical_formula_sum 'C45 H50 Br2 O7 P2' _chemical_formula_weight 924.61 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3604(2) _cell_length_b 23.4811(5) _cell_length_c 9.7168(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.4880(10) _cell_angle_gamma 90.00 _cell_volume 2125.89(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 38076 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5625 _exptl_absorpt_correction_T_max 0.9052 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16969 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.1045 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.49 _reflns_number_total 9299 _reflns_number_gt 7521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0632P)^2^+0.6745P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(8) _refine_ls_number_reflns 9299 _refine_ls_number_parameters 511 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.011 _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 Br1 Br -0.37946(6) 0.38798(2) 0.27836(6) 0.03442(16) Uani 1 1 d . . . Br2 Br 0.22382(7) 0.23504(3) -0.42184(7) 0.04291(18) Uani 1 1 d . . . P1 P -0.11464(14) 0.22447(6) 0.02887(14) 0.0232(3) Uani 1 1 d . . . P2 P 0.14456(14) 0.43159(6) -0.10118(14) 0.0220(3) Uani 1 1 d . . . O1 O -0.0420(4) 0.27940(15) 0.0982(4) 0.0243(8) Uani 1 1 d . . . O2 O 0.1692(4) 0.36901(15) -0.0466(4) 0.0229(8) Uani 1 1 d . . . O3 O 0.1218(4) 0.37463(15) 0.2199(4) 0.0272(8) Uani 1 1 d . . . O4 O 0.2326(4) 0.25415(16) 0.0697(4) 0.0291(9) Uani 1 1 d . . . C1 C 0.0507(5) 0.2790(2) 0.2283(5) 0.0220(11) Uani 1 1 d . . . H1 H 0.0276 0.2470 0.2904 0.026 Uiso 1 1 calc R . . C2 C 0.2083(5) 0.2791(2) 0.1989(6) 0.0252(11) Uani 1 1 d . . . H2 H 0.2687 0.2599 0.2757 0.030 Uiso 1 1 calc R . . C3 C 0.2473(6) 0.3428(2) 0.1930(6) 0.0260(12) Uani 1 1 d . . . H3 H 0.3290 0.3519 0.2635 0.031 Uiso 1 1 calc R . . C4 C 0.0351(6) 0.3370(2) 0.2947(6) 0.0264(12) Uani 1 1 d . . . H4A H -0.0665 0.3495 0.2853 0.032 Uiso 1 1 calc R . . H4B H 0.0702 0.3360 0.3940 0.032 Uiso 1 1 calc R . . C5 C 0.3328(6) 0.2913(2) 0.0055(7) 0.0310(13) Uani 1 1 d . . . H5A H 0.3221 0.2868 -0.0963 0.037 Uiso 1 1 calc R . . H5B H 0.4331 0.2825 0.0405 0.037 Uiso 1 1 calc R . . C6 C 0.2928(6) 0.3507(2) 0.0459(5) 0.0253(12) Uani 1 1 d . . . H6 H 0.3752 0.3777 0.0444 0.030 Uiso 1 1 calc R . . C7 C 0.0101(6) 0.1672(2) 0.0211(6) 0.0259(12) Uani 1 1 d . . . C8 C 0.0460(6) 0.1355(3) 0.1378(7) 0.0325(13) Uani 1 1 d . . . H8 H 0.0005 0.1426 0.2193 0.039 Uiso 1 1 calc R . . C9 C 0.1490(7) 0.0932(3) 0.1365(8) 0.0421(16) Uani 1 1 d . . . H9 H 0.1729 0.0705 0.2164 0.051 Uiso 1 1 calc R . . C10 C 0.2166(7) 0.0842(3) 0.0185(9) 0.053(2) Uani 1 1 d . . . H10 H 0.2878 0.0553 0.0182 0.063 Uiso 1 1 calc R . . C11 C 0.1831(7) 0.1161(3) -0.0996(8) 0.0407(15) Uani 1 1 d . . . H11 H 0.2304 0.1096 -0.1804 0.049 Uiso 1 1 calc R . . C12 C 0.0789(6) 0.1579(2) -0.0973(7) 0.0323(13) Uani 1 1 d . . . H12 H 0.0543 0.1804 -0.1774 0.039 Uiso 1 1 calc R . . C13 C -0.1840(6) 0.2504(2) -0.1369(5) 0.0259(12) Uani 1 1 d . . . C14 C -0.3272(7) 0.2419(3) -0.1849(6) 0.0369(14) Uani 1 1 d . . . H14 H -0.3889 0.2209 -0.1315 0.044 Uiso 1 1 calc R . . C15 C -0.3788(7) 0.2647(3) -0.3127(7) 0.0422(16) Uani 1 1 d . . . H15 H -0.4749 0.2577 -0.3496 0.051 Uiso 1 1 calc R . . C16 C -0.2881(8) 0.2979(3) -0.3858(7) 0.0441(17) Uani 1 1 d . . . H16 H -0.3249 0.3158 -0.4696 0.053 Uiso 1 1 calc R . . C17 C -0.1452(8) 0.3052(3) -0.3379(7) 0.0393(15) Uani 1 1 d . . . H17 H -0.0835 0.3262 -0.3912 0.047 Uiso 1 1 calc R . . C18 C -0.0926(6) 0.2822(2) -0.2141(6) 0.0312(13) Uani 1 1 d . . . H18 H 0.0051 0.2877 -0.1804 0.037 Uiso 1 1 calc R . . C19 C -0.2562(6) 0.2019(2) 0.1249(6) 0.0271(12) Uani 1 1 d . . . C20 C -0.3130(6) 0.1463(2) 0.1085(7) 0.0328(13) Uani 1 1 d . . . H20 H -0.2715 0.1197 0.0504 0.039 Uiso 1 1 calc R . . C21 C -0.4294(6) 0.1309(3) 0.1780(7) 0.0387(15) Uani 1 1 d . . . H21 H -0.4690 0.0938 0.1669 0.046 Uiso 1 1 calc R . . C22 C -0.4886(6) 0.1703(3) 0.2646(7) 0.0377(15) Uani 1 1 d . . . H22 H -0.5687 0.1597 0.3119 0.045 Uiso 1 1 calc R . . C23 C -0.4320(6) 0.2242(3) 0.2819(6) 0.0317(13) Uani 1 1 d . . . H23 H -0.4717 0.2504 0.3424 0.038 Uiso 1 1 calc R . . C24 C -0.3174(6) 0.2402(3) 0.2111(6) 0.0301(12) Uani 1 1 d . . . H24 H -0.2800 0.2777 0.2214 0.036 Uiso 1 1 calc R . . C25 C 0.2341(5) 0.4394(2) -0.2545(5) 0.0235(11) Uani 1 1 d . . . C26 C 0.2629(7) 0.4943(3) -0.3055(6) 0.0327(13) Uani 1 1 d . . . H26 H 0.2387 0.5273 -0.2561 0.039 Uiso 1 1 calc R . . C27 C 0.3255(8) 0.4995(3) -0.4257(7) 0.0400(15) Uani 1 1 d . . . H27 H 0.3433 0.5364 -0.4604 0.048 Uiso 1 1 calc R . . C28 C 0.3635(7) 0.4518(3) -0.4981(7) 0.0380(14) Uani 1 1 d . . . H28 H 0.4073 0.4558 -0.5819 0.046 Uiso 1 1 calc R . . C29 C 0.3368(6) 0.3984(3) -0.4467(6) 0.0347(14) Uani 1 1 d . . . H29 H 0.3654 0.3658 -0.4949 0.042 Uiso 1 1 calc R . . C30 C 0.2697(5) 0.3911(3) -0.3274(5) 0.0266(11) Uani 1 1 d . . . H30 H 0.2484 0.3541 -0.2957 0.032 Uiso 1 1 calc R . . C31 C -0.0458(5) 0.4345(2) -0.1415(5) 0.0236(11) Uani 1 1 d . . . C32 C -0.1344(6) 0.4155(2) -0.0447(6) 0.0288(12) Uani 1 1 d . . . H32 H -0.0943 0.4036 0.0441 0.035 Uiso 1 1 calc R . . C33 C -0.2804(7) 0.4141(3) -0.0775(7) 0.0362(14) Uani 1 1 d . . . H33 H -0.3417 0.4006 -0.0122 0.043 Uiso 1 1 calc R . . C34 C -0.3378(6) 0.4327(3) -0.2078(6) 0.0360(14) Uani 1 1 d . . . H34 H -0.4387 0.4312 -0.2311 0.043 Uiso 1 1 calc R . . C35 C -0.2520(7) 0.4527(3) -0.3016(7) 0.0403(16) Uani 1 1 d . . . H35 H -0.2931 0.4661 -0.3889 0.048 Uiso 1 1 calc R . . C36 C -0.1009(6) 0.4539(3) -0.2697(6) 0.0317(13) Uani 1 1 d . . . H36 H -0.0395 0.4675 -0.3347 0.038 Uiso 1 1 calc R . . C37 C 0.2133(5) 0.4836(2) 0.0188(5) 0.0233(11) Uani 1 1 d . . . C38 C 0.3601(6) 0.4938(2) 0.0397(6) 0.0282(12) Uani 1 1 d . . . H38 H 0.4231 0.4741 -0.0149 0.034 Uiso 1 1 calc R . . C39 C 0.4161(6) 0.5323(3) 0.1391(6) 0.0359(14) Uani 1 1 d . . . H39 H 0.5168 0.5383 0.1531 0.043 Uiso 1 1 calc R . . C40 C 0.3246(7) 0.5620(2) 0.2180(6) 0.0321(13) Uani 1 1 d . . . H40 H 0.3621 0.5888 0.2855 0.038 Uiso 1 1 calc R . . C41 C 0.1774(7) 0.5522(3) 0.1971(6) 0.0330(13) Uani 1 1 d . . . H41 H 0.1149 0.5727 0.2506 0.040 Uiso 1 1 calc R . . C42 C 0.1203(6) 0.5134(2) 0.1005(6) 0.0284(12) Uani 1 1 d . . . H42 H 0.0198 0.5067 0.0889 0.034 Uiso 1 1 calc R . . C43 C -0.1411(8) 0.1568(3) 0.5105(8) 0.0501(18) Uani 1 1 d . . . H43A H -0.1539 0.1578 0.6093 0.075 Uiso 1 1 calc R . . H43B H -0.2184 0.1344 0.4617 0.075 Uiso 1 1 calc R . . H43C H -0.1438 0.1957 0.4737 0.075 Uiso 1 1 calc R . . O5 O -0.0142(7) 0.1329(3) 0.4921(11) 0.104(3) Uani 1 1 d . . . H5 H 0.0425 0.1581 0.4687 0.050 Uiso 1 1 calc R . . O6 O 0.5692(9) 0.6210(4) 0.4089(10) 0.105(3) Uani 1 1 d . . . H6A H 0.5969 0.6528 0.4410 0.050 Uiso 1 1 calc R . . C44 C 0.6450(12) 0.5828(5) 0.4660(10) 0.077(3) Uani 1 1 d . . . H44A H 0.7193 0.5719 0.4065 0.116 Uiso 1 1 calc R . . H44B H 0.5852 0.5497 0.4819 0.116 Uiso 1 1 calc R . . H44C H 0.6904 0.5968 0.5547 0.116 Uiso 1 1 calc R . . O7 O -0.1609(10) 0.4916(4) 0.2545(9) 0.109(3) Uani 1 1 d . . . H7 H -0.1942 0.4599 0.2267 0.050 Uiso 1 1 calc R . . C45 C -0.0787(11) 0.4845(5) 0.3741(9) 0.082(3) Uani 1 1 d . . . H45A H 0.0147 0.4690 0.3554 0.123 Uiso 1 1 calc R . . H45B H -0.1259 0.4580 0.4332 0.123 Uiso 1 1 calc R . . H45C H -0.0649 0.5213 0.4211 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0296(3) 0.0372(3) 0.0361(3) 0.0007(3) 0.0015(2) 0.0040(3) Br2 0.0370(3) 0.0445(4) 0.0468(4) 0.0086(3) 0.0013(3) -0.0004(3) P1 0.0214(6) 0.0247(7) 0.0228(7) 0.0004(5) -0.0001(5) -0.0003(6) P2 0.0211(6) 0.0258(7) 0.0187(7) -0.0001(5) 0.0006(5) 0.0009(6) O1 0.0204(17) 0.0284(19) 0.023(2) -0.0003(15) -0.0051(14) -0.0009(15) O2 0.0189(17) 0.0241(18) 0.025(2) 0.0020(15) -0.0045(14) -0.0009(15) O3 0.0326(19) 0.027(2) 0.023(2) -0.0016(15) 0.0087(15) 0.0010(16) O4 0.0277(19) 0.030(2) 0.031(2) 0.0003(16) 0.0112(16) -0.0036(16) C1 0.013(2) 0.032(3) 0.020(3) 0.004(2) 0.0019(19) 0.000(2) C2 0.022(3) 0.027(3) 0.025(3) 0.005(2) 0.001(2) 0.003(2) C3 0.023(3) 0.030(3) 0.024(3) 0.001(2) -0.005(2) -0.001(2) C4 0.026(3) 0.034(3) 0.019(3) -0.004(2) 0.001(2) -0.004(2) C5 0.025(3) 0.036(3) 0.033(3) 0.009(3) 0.005(2) 0.001(2) C6 0.022(3) 0.037(3) 0.016(3) -0.001(2) -0.003(2) 0.006(2) C7 0.021(2) 0.025(3) 0.031(3) -0.003(2) 0.002(2) -0.007(2) C8 0.026(3) 0.035(3) 0.035(4) -0.001(3) -0.003(2) -0.003(3) C9 0.042(4) 0.031(3) 0.052(4) 0.003(3) -0.002(3) 0.000(3) C10 0.034(3) 0.033(4) 0.090(6) -0.014(4) 0.004(4) 0.004(3) C11 0.034(3) 0.037(3) 0.052(4) -0.009(3) 0.011(3) 0.000(3) C12 0.029(3) 0.029(3) 0.040(4) -0.003(3) 0.005(3) 0.001(2) C13 0.029(3) 0.029(3) 0.019(3) 0.000(2) -0.002(2) 0.000(2) C14 0.037(3) 0.045(4) 0.027(3) 0.000(3) -0.002(2) -0.008(3) C15 0.035(3) 0.052(4) 0.036(4) -0.003(3) -0.014(3) -0.002(3) C16 0.054(4) 0.041(4) 0.033(4) -0.003(3) -0.016(3) 0.004(3) C17 0.052(4) 0.039(3) 0.027(3) 0.002(3) 0.007(3) -0.005(3) C18 0.033(3) 0.030(3) 0.030(3) -0.001(2) -0.005(2) 0.002(2) C19 0.025(3) 0.030(3) 0.026(3) 0.004(2) 0.002(2) -0.004(2) C20 0.036(3) 0.024(3) 0.037(4) 0.004(2) -0.002(3) -0.003(3) C21 0.032(3) 0.034(3) 0.049(4) 0.003(3) 0.001(3) -0.001(3) C22 0.021(3) 0.048(4) 0.044(4) 0.015(3) 0.003(3) 0.003(3) C23 0.023(3) 0.041(3) 0.030(3) -0.003(3) 0.003(2) 0.002(3) C24 0.035(3) 0.026(3) 0.028(3) -0.004(2) 0.000(2) -0.005(3) C25 0.019(2) 0.029(3) 0.023(3) -0.002(2) 0.005(2) 0.000(2) C26 0.041(3) 0.033(3) 0.026(3) 0.002(2) 0.009(3) 0.001(3) C27 0.056(4) 0.029(3) 0.036(4) 0.004(3) 0.007(3) -0.002(3) C28 0.038(3) 0.048(4) 0.028(3) 0.005(3) 0.003(3) 0.002(3) C29 0.032(3) 0.044(4) 0.027(3) -0.002(3) -0.002(2) 0.010(3) C30 0.023(2) 0.031(3) 0.026(3) 0.001(3) 0.001(2) -0.001(3) C31 0.018(2) 0.027(3) 0.025(3) -0.002(2) -0.002(2) -0.003(2) C32 0.024(3) 0.037(3) 0.025(3) 0.002(2) 0.001(2) 0.002(2) C33 0.034(3) 0.044(3) 0.031(3) 0.001(3) 0.002(2) -0.003(3) C34 0.018(2) 0.056(4) 0.032(3) -0.003(3) -0.005(2) 0.007(3) C35 0.032(3) 0.051(4) 0.035(4) 0.001(3) -0.008(3) 0.010(3) C36 0.026(3) 0.042(3) 0.028(3) 0.007(3) 0.001(2) 0.005(3) C37 0.021(2) 0.025(3) 0.022(3) 0.000(2) -0.001(2) -0.002(2) C38 0.028(3) 0.031(3) 0.025(3) -0.001(2) 0.002(2) -0.002(2) C39 0.030(3) 0.042(4) 0.035(4) 0.002(3) -0.004(3) -0.011(3) C40 0.041(3) 0.026(3) 0.028(3) -0.006(2) -0.004(3) -0.001(3) C41 0.034(3) 0.035(3) 0.029(3) -0.002(3) 0.002(2) 0.001(3) C42 0.026(3) 0.035(3) 0.024(3) -0.001(2) 0.001(2) 0.003(2) C43 0.043(4) 0.063(5) 0.043(4) 0.004(4) 0.002(3) -0.002(4) O5 0.052(4) 0.093(5) 0.167(8) -0.049(5) 0.007(4) -0.013(4) O6 0.077(5) 0.086(5) 0.145(8) -0.015(5) -0.024(5) -0.018(4) C44 0.076(6) 0.095(7) 0.059(6) -0.002(5) 0.004(5) -0.032(6) O7 0.124(7) 0.095(6) 0.111(7) 0.010(5) 0.028(6) -0.029(5) C45 0.088(7) 0.127(9) 0.033(5) -0.010(5) 0.011(5) -0.050(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.579(4) . ? P1 C19 1.773(6) . ? P1 C13 1.785(5) . ? P1 C7 1.787(6) . ? P2 O2 1.572(4) . ? P2 C37 1.767(5) . ? P2 C25 1.787(5) . ? P2 C31 1.789(5) . ? O1 C1 1.463(6) . ? O2 C6 1.460(6) . ? O3 C3 1.437(6) . ? O3 C4 1.442(7) . ? O4 C2 1.423(7) . ? O4 C5 1.463(7) . ? C1 C4 1.522(8) . ? C1 C2 1.530(7) . ? C2 C3 1.541(8) . ? C3 C6 1.541(8) . ? C5 C6 1.506(8) . ? C7 C8 1.371(8) . ? C7 C12 1.388(8) . ? C8 C9 1.386(9) . ? C9 C10 1.378(11) . ? C10 C11 1.382(11) . ? C11 C12 1.384(9) . ? C13 C14 1.391(8) . ? C13 C18 1.406(8) . ? C14 C15 1.396(9) . ? C15 C16 1.397(10) . ? C16 C17 1.384(10) . ? C17 C18 1.367(9) . ? C19 C24 1.389(8) . ? C19 C20 1.413(8) . ? C20 C21 1.383(9) . ? C21 C22 1.400(10) . ? C22 C23 1.377(9) . ? C23 C24 1.381(8) . ? C25 C30 1.393(8) . ? C25 C26 1.416(8) . ? C26 C27 1.361(9) . ? C27 C28 1.387(9) . ? C28 C29 1.381(9) . ? C29 C30 1.381(8) . ? C31 C36 1.379(8) . ? C31 C32 1.385(8) . ? C32 C33 1.374(8) . ? C33 C34 1.397(9) . ? C34 C35 1.356(9) . ? C35 C36 1.419(8) . ? C37 C38 1.391(8) . ? C37 C42 1.418(8) . ? C38 C39 1.389(8) . ? C39 C40 1.391(9) . ? C40 C41 1.392(9) . ? C41 C42 1.379(8) . ? C43 O5 1.341(10) . ? O6 C44 1.240(12) . ? O7 C45 1.341(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C19 109.4(2) . . ? O1 P1 C13 102.2(2) . . ? C19 P1 C13 110.5(3) . . ? O1 P1 C7 112.1(2) . . ? C19 P1 C7 108.8(3) . . ? C13 P1 C7 113.6(3) . . ? O2 P2 C37 113.0(2) . . ? O2 P2 C25 108.2(2) . . ? C37 P2 C25 108.0(3) . . ? O2 P2 C31 102.8(2) . . ? C37 P2 C31 114.2(3) . . ? C25 P2 C31 110.5(2) . . ? C1 O1 P1 124.0(3) . . ? C6 O2 P2 124.4(3) . . ? C3 O3 C4 106.4(4) . . ? C2 O4 C5 107.0(4) . . ? O1 C1 C4 106.7(4) . . ? O1 C1 C2 110.0(4) . . ? C4 C1 C2 102.2(4) . . ? O4 C2 C1 113.7(4) . . ? O4 C2 C3 108.0(4) . . ? C1 C2 C3 104.2(4) . . ? O3 C3 C6 114.1(4) . . ? O3 C3 C2 107.3(4) . . ? C6 C3 C2 103.8(5) . . ? O3 C4 C1 104.7(4) . . ? O4 C5 C6 104.8(5) . . ? O2 C6 C5 108.3(4) . . ? O2 C6 C3 109.5(4) . . ? C5 C6 C3 103.1(5) . . ? C8 C7 C12 120.2(5) . . ? C8 C7 P1 118.9(5) . . ? C12 C7 P1 120.7(4) . . ? C7 C8 C9 119.9(6) . . ? C10 C9 C8 119.5(7) . . ? C9 C10 C11 121.5(6) . . ? C10 C11 C12 118.4(6) . . ? C11 C12 C7 120.5(6) . . ? C14 C13 C18 120.9(5) . . ? C14 C13 P1 120.6(4) . . ? C18 C13 P1 118.4(4) . . ? C13 C14 C15 118.9(6) . . ? C16 C15 C14 119.4(6) . . ? C17 C16 C15 120.9(6) . . ? C18 C17 C16 120.2(6) . . ? C17 C18 C13 119.6(6) . . ? C24 C19 C20 119.6(5) . . ? C24 C19 P1 119.7(4) . . ? C20 C19 P1 120.6(5) . . ? C21 C20 C19 119.4(6) . . ? C20 C21 C22 119.8(6) . . ? C23 C22 C21 120.7(6) . . ? C22 C23 C24 119.8(6) . . ? C23 C24 C19 120.6(6) . . ? C30 C25 C26 120.0(5) . . ? C30 C25 P2 119.6(4) . . ? C26 C25 P2 120.3(4) . . ? C27 C26 C25 119.6(5) . . ? C26 C27 C28 121.0(6) . . ? C29 C28 C27 119.0(6) . . ? C28 C29 C30 121.9(6) . . ? C29 C30 C25 118.4(6) . . ? C36 C31 C32 121.5(5) . . ? C36 C31 P2 119.3(4) . . ? C32 C31 P2 119.2(4) . . ? C33 C32 C31 119.8(5) . . ? C32 C33 C34 119.4(6) . . ? C35 C34 C33 121.1(5) . . ? C34 C35 C36 120.1(6) . . ? C31 C36 C35 118.1(6) . . ? C38 C37 C42 119.0(5) . . ? C38 C37 P2 120.5(4) . . ? C42 C37 P2 120.5(4) . . ? C39 C38 C37 121.0(5) . . ? C38 C39 C40 119.9(5) . . ? C39 C40 C41 119.3(5) . . ? C42 C41 C40 121.5(6) . . ? C41 C42 C37 119.3(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 C19 P1 O1 C1 72.8(4) . . . . ? C13 P1 O1 C1 -170.0(4) . . . . ? C7 P1 O1 C1 -48.0(4) . . . . ? C37 P2 O2 C6 -32.4(5) . . . . ? C25 P2 O2 C6 87.1(4) . . . . ? C31 P2 O2 C6 -156.0(4) . . . . ? P1 O1 C1 C4 -151.5(3) . . . . ? P1 O1 C1 C2 98.5(5) . . . . ? C5 O4 C2 C1 136.2(4) . . . . ? C5 O4 C2 C3 21.1(5) . . . . ? O1 C1 C2 O4 -27.3(6) . . . . ? C4 C1 C2 O4 -140.3(4) . . . . ? O1 C1 C2 C3 90.0(5) . . . . ? C4 C1 C2 C3 -23.0(5) . . . . ? C4 O3 C3 C6 137.4(5) . . . . ? C4 O3 C3 C2 23.0(5) . . . . ? O4 C2 C3 O3 122.3(4) . . . . ? C1 C2 C3 O3 1.1(5) . . . . ? O4 C2 C3 C6 1.1(5) . . . . ? C1 C2 C3 C6 -120.1(4) . . . . ? C3 O3 C4 C1 -38.3(5) . . . . ? O1 C1 C4 O3 -77.8(5) . . . . ? C2 C1 C4 O3 37.6(5) . . . . ? C2 O4 C5 C6 -35.6(5) . . . . ? P2 O2 C6 C5 -143.9(4) . . . . ? P2 O2 C6 C3 104.4(5) . . . . ? O4 C5 C6 O2 -80.9(5) . . . . ? O4 C5 C6 C3 35.1(5) . . . . ? O3 C3 C6 O2 -23.2(6) . . . . ? C2 C3 C6 O2 93.2(5) . . . . ? O3 C3 C6 C5 -138.3(4) . . . . ? C2 C3 C6 C5 -21.9(5) . . . . ? O1 P1 C7 C8 79.1(5) . . . . ? C19 P1 C7 C8 -42.1(5) . . . . ? C13 P1 C7 C8 -165.6(4) . . . . ? O1 P1 C7 C12 -95.4(5) . . . . ? C19 P1 C7 C12 143.4(4) . . . . ? C13 P1 C7 C12 19.9(5) . . . . ? C12 C7 C8 C9 -1.5(8) . . . . ? P1 C7 C8 C9 -176.1(5) . . . . ? C7 C8 C9 C10 1.4(9) . . . . ? C8 C9 C10 C11 -0.6(10) . . . . ? C9 C10 C11 C12 -0.1(10) . . . . ? C10 C11 C12 C7 0.0(9) . . . . ? C8 C7 C12 C11 0.8(8) . . . . ? P1 C7 C12 C11 175.3(5) . . . . ? O1 P1 C13 C14 -127.7(5) . . . . ? C19 P1 C13 C14 -11.3(6) . . . . ? C7 P1 C13 C14 111.3(5) . . . . ? O1 P1 C13 C18 48.8(5) . . . . ? C19 P1 C13 C18 165.2(4) . . . . ? C7 P1 C13 C18 -72.2(5) . . . . ? C18 C13 C14 C15 1.1(9) . . . . ? P1 C13 C14 C15 177.5(5) . . . . ? C13 C14 C15 C16 -3.3(10) . . . . ? C14 C15 C16 C17 4.5(11) . . . . ? C15 C16 C17 C18 -3.3(10) . . . . ? C16 C17 C18 C13 1.0(10) . . . . ? C14 C13 C18 C17 0.1(9) . . . . ? P1 C13 C18 C17 -176.4(5) . . . . ? O1 P1 C19 C24 20.8(5) . . . . ? C13 P1 C19 C24 -91.0(5) . . . . ? C7 P1 C19 C24 143.6(5) . . . . ? O1 P1 C19 C20 -162.8(4) . . . . ? C13 P1 C19 C20 85.3(5) . . . . ? C7 P1 C19 C20 -40.0(5) . . . . ? C24 C19 C20 C21 0.5(9) . . . . ? P1 C19 C20 C21 -175.9(5) . . . . ? C19 C20 C21 C22 -0.7(9) . . . . ? C20 C21 C22 C23 -0.2(10) . . . . ? C21 C22 C23 C24 1.3(9) . . . . ? C22 C23 C24 C19 -1.5(9) . . . . ? C20 C19 C24 C23 0.7(9) . . . . ? P1 C19 C24 C23 177.1(4) . . . . ? O2 P2 C25 C30 19.7(5) . . . . ? C37 P2 C25 C30 142.4(4) . . . . ? C31 P2 C25 C30 -92.0(5) . . . . ? O2 P2 C25 C26 -163.1(4) . . . . ? C37 P2 C25 C26 -40.5(5) . . . . ? C31 P2 C25 C26 85.1(5) . . . . ? C30 C25 C26 C27 0.0(8) . . . . ? P2 C25 C26 C27 -177.1(5) . . . . ? C25 C26 C27 C28 -1.0(10) . . . . ? C26 C27 C28 C29 0.1(10) . . . . ? C27 C28 C29 C30 1.8(9) . . . . ? C28 C29 C30 C25 -2.8(8) . . . . ? C26 C25 C30 C29 1.8(8) . . . . ? P2 C25 C30 C29 179.0(4) . . . . ? O2 P2 C31 C36 -129.0(5) . . . . ? C37 P2 C31 C36 108.3(5) . . . . ? C25 P2 C31 C36 -13.7(6) . . . . ? O2 P2 C31 C32 48.9(5) . . . . ? C37 P2 C31 C32 -73.8(5) . . . . ? C25 P2 C31 C32 164.1(4) . . . . ? C36 C31 C32 C33 2.0(9) . . . . ? P2 C31 C32 C33 -175.8(5) . . . . ? C31 C32 C33 C34 -1.0(9) . . . . ? C32 C33 C34 C35 -0.8(10) . . . . ? C33 C34 C35 C36 1.6(10) . . . . ? C32 C31 C36 C35 -1.3(9) . . . . ? P2 C31 C36 C35 176.5(5) . . . . ? C34 C35 C36 C31 -0.5(9) . . . . ? O2 P2 C37 C38 75.6(5) . . . . ? C25 P2 C37 C38 -44.1(5) . . . . ? C31 P2 C37 C38 -167.4(4) . . . . ? O2 P2 C37 C42 -101.1(5) . . . . ? C25 P2 C37 C42 139.3(5) . . . . ? C31 P2 C37 C42 15.9(5) . . . . ? C42 C37 C38 C39 0.3(8) . . . . ? P2 C37 C38 C39 -176.5(5) . . . . ? C37 C38 C39 C40 -1.1(9) . . . . ? C38 C39 C40 C41 0.7(9) . . . . ? C39 C40 C41 C42 0.4(9) . . . . ? C40 C41 C42 C37 -1.2(9) . . . . ? C38 C37 C42 C41 0.8(8) . . . . ? P2 C37 C42 C41 177.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 Br1 0.84 2.51 3.201(8) 140.7 . O5 H5 Br2 0.84 2.63 3.325(7) 140.6 1_556 O6 H6A Br2 0.84 2.58 3.301(8) 144.9 2_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.185 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.094 data_4 _database_code_depnum_ccdc_archive 'CCDC 230132' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H34 N2 O2 P2 Rh, CH3CN, BF4' _chemical_formula_sum 'C36 H37 B F4 N3 O2 P2 Rh' _chemical_formula_weight 795.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.2793(2) _cell_length_b 15.1367(4) _cell_length_c 11.5954(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.7005(12) _cell_angle_gamma 90.00 _cell_volume 1772.81(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 'all obs. reflections in the data set' _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.47 _exptl_crystal_description bloc _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8335 _exptl_absorpt_correction_T_max 0.8739 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius kappa CCD area detector' _diffrn_measurement_method 'omega & phi scan to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16148 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6563 _reflns_number_gt 6270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+1.3331P] 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 'calculated positions, riding model' _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 -0.04(2) _refine_ls_number_reflns 6563 _refine_ls_number_parameters 445 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Rh1 Rh 0.06262(2) 0.335017(17) 0.236436(18) 0.01656(6) Uani 1 1 d . . . P1 P 0.14680(8) 0.19917(6) 0.22135(7) 0.01716(17) Uani 1 1 d . . . P2 P 0.17036(8) 0.36860(6) 0.41721(7) 0.01701(17) Uani 1 1 d . . . O1 O 0.4118(2) 0.24022(17) 0.3477(2) 0.0260(5) Uani 1 1 d . . . O2 O 0.1765(2) 0.19241(16) 0.5121(2) 0.0249(5) Uani 1 1 d . . . C1 C 0.3124(3) 0.2175(2) 0.5169(3) 0.0229(7) Uani 1 1 d . . . H1 H 0.3688 0.1995 0.5931 0.028 Uiso 1 1 calc R . . C2 C 0.3258(3) 0.3173(2) 0.4941(3) 0.0219(8) Uani 1 1 d . . . H2 H 0.3579 0.3486 0.5699 0.026 Uiso 1 1 calc R . . C3 C 0.4340(3) 0.3169(2) 0.4204(3) 0.0258(8) Uani 1 1 d . . . H3A H 0.4290 0.3710 0.3718 0.031 Uiso 1 1 calc R . . H3B H 0.5225 0.3142 0.4716 0.031 Uiso 1 1 calc R . . C4 C 0.3587(3) 0.1726(2) 0.4122(3) 0.0259(8) Uani 1 1 d . . . H4 H 0.4275 0.1269 0.4405 0.031 Uiso 1 1 calc R . . C5 C 0.2330(3) 0.1289(2) 0.3427(3) 0.0230(7) Uani 1 1 d . . . H5 H 0.2557 0.0706 0.3112 0.028 Uiso 1 1 calc R . . C6 C 0.1540(4) 0.1149(2) 0.4400(3) 0.0258(8) Uani 1 1 d . . . H6A H 0.0586 0.1082 0.4067 0.031 Uiso 1 1 calc R . . H6B H 0.1849 0.0614 0.4861 0.031 Uiso 1 1 calc R . . C7 C 0.0083(3) 0.1243(2) 0.1606(3) 0.0190(7) Uani 1 1 d . . . C8 C -0.1084(4) 0.1328(3) 0.2050(3) 0.0254(8) Uani 1 1 d . . . H8 H -0.1127 0.1743 0.2656 0.030 Uiso 1 1 calc R . . C9 C -0.2188(4) 0.0810(2) 0.1612(3) 0.0269(8) Uani 1 1 d . . . H9 H -0.2973 0.0865 0.1929 0.032 Uiso 1 1 calc R . . C10 C -0.2136(4) 0.0216(2) 0.0718(3) 0.0279(8) Uani 1 1 d . . . H10 H -0.2889 -0.0133 0.0414 0.034 Uiso 1 1 calc R . . C11 C -0.0993(4) 0.0128(2) 0.0264(3) 0.0272(8) Uani 1 1 d . . . H11 H -0.0965 -0.0277 -0.0358 0.033 Uiso 1 1 calc R . . C12 C 0.0123(3) 0.0632(2) 0.0715(3) 0.0222(7) Uani 1 1 d . . . H12 H 0.0913 0.0558 0.0412 0.027 Uiso 1 1 calc R . . C13 C 0.2556(3) 0.1944(2) 0.1133(3) 0.0200(7) Uani 1 1 d . . . C14 C 0.3332(3) 0.1208(3) 0.0995(3) 0.0267(8) Uani 1 1 d . . . H14 H 0.3324 0.0710 0.1491 0.032 Uiso 1 1 calc R . . C15 C 0.4111(4) 0.1198(3) 0.0146(4) 0.0336(9) Uani 1 1 d . . . H15 H 0.4624 0.0689 0.0058 0.040 Uiso 1 1 calc R . . C16 C 0.4155(3) 0.1920(3) -0.0583(3) 0.0310(9) Uani 1 1 d . . . H16 H 0.4700 0.1907 -0.1161 0.037 Uiso 1 1 calc R . . C17 C 0.3399(4) 0.2661(3) -0.0463(3) 0.0296(8) Uani 1 1 d . . . H17 H 0.3417 0.3158 -0.0959 0.036 Uiso 1 1 calc R . . C18 C 0.2610(3) 0.2669(2) 0.0398(3) 0.0244(7) Uani 1 1 d . . . H18 H 0.2100 0.3179 0.0486 0.029 Uiso 1 1 calc R . . C19 C 0.2266(3) 0.4840(2) 0.4168(3) 0.0203(7) Uani 1 1 d . . . C20 C 0.2113(4) 0.5449(3) 0.5029(3) 0.0312(9) Uani 1 1 d . . . H20 H 0.1722 0.5274 0.5674 0.037 Uiso 1 1 calc R . . C21 C 0.2532(5) 0.6318(3) 0.4944(4) 0.0410(10) Uani 1 1 d . . . H21 H 0.2401 0.6735 0.5524 0.049 Uiso 1 1 calc R . . C22 C 0.3129(4) 0.6583(3) 0.4042(4) 0.0335(9) Uani 1 1 d . . . H22 H 0.3408 0.7178 0.3994 0.040 Uiso 1 1 calc R . . C23 C 0.3325(4) 0.5975(3) 0.3197(3) 0.0279(8) Uani 1 1 d . . . H23 H 0.3770 0.6146 0.2584 0.033 Uiso 1 1 calc R . . C24 C 0.2871(3) 0.5119(2) 0.3248(3) 0.0240(7) Uani 1 1 d . . . H24 H 0.2972 0.4713 0.2646 0.029 Uiso 1 1 calc R . . C25 C 0.0632(3) 0.3694(2) 0.5272(3) 0.0222(7) Uani 1 1 d . . . C26 C 0.1118(4) 0.3670(3) 0.6475(3) 0.0306(9) Uani 1 1 d . . . H26 H 0.2044 0.3616 0.6755 0.037 Uiso 1 1 calc R . . C27 C 0.0272(4) 0.3725(3) 0.7262(3) 0.0361(9) Uani 1 1 d . . . H27 H 0.0615 0.3695 0.8081 0.043 Uiso 1 1 calc R . . C28 C -0.1087(4) 0.3822(2) 0.6865(3) 0.0319(9) Uani 1 1 d . . . H28 H -0.1667 0.3883 0.7410 0.038 Uiso 1 1 calc R . . C29 C -0.1582(4) 0.3829(3) 0.5677(4) 0.0316(9) Uani 1 1 d . . . H29 H -0.2508 0.3885 0.5401 0.038 Uiso 1 1 calc R . . C30 C -0.0733(3) 0.3756(3) 0.4881(3) 0.0267(8) Uani 1 1 d . . . H30 H -0.1084 0.3747 0.4063 0.032 Uiso 1 1 calc R . . N1 N -0.0231(3) 0.4588(2) 0.2321(2) 0.0224(6) Uani 1 1 d . . . C31 C -0.0615(4) 0.5295(3) 0.2328(3) 0.0250(8) Uani 1 1 d . . . C32 C -0.1066(5) 0.6201(3) 0.2370(4) 0.0415(10) Uani 1 1 d . . . H32A H -0.1926 0.6209 0.2621 0.062 Uiso 1 1 calc R . . H32B H -0.1156 0.6467 0.1589 0.062 Uiso 1 1 calc R . . H32C H -0.0422 0.6538 0.2929 0.062 Uiso 1 1 calc R . . N2 N -0.0508(3) 0.31103(18) 0.0726(2) 0.0222(7) Uani 1 1 d . . . C33 C -0.1157(3) 0.2806(2) -0.0074(3) 0.0233(7) Uani 1 1 d . . . C34 C -0.1971(4) 0.2333(3) -0.1037(3) 0.0365(9) Uani 1 1 d . . . H34A H -0.2053 0.1714 -0.0813 0.055 Uiso 1 1 calc R . . H34B H -0.1558 0.2363 -0.1732 0.055 Uiso 1 1 calc R . . H34C H -0.2852 0.2604 -0.1214 0.055 Uiso 1 1 calc R . . N3 N 0.6314(6) 0.4914(4) 0.2761(6) 0.0886(19) Uani 1 1 d . . . C35 C 0.6281(5) 0.4246(5) 0.2293(5) 0.0631(16) Uani 1 1 d . . . C36 C 0.6265(5) 0.3394(6) 0.1709(5) 0.0820(18) Uani 1 1 d . . . H36A H 0.7135 0.3112 0.1929 0.123 Uiso 1 1 calc R . . H36B H 0.6062 0.3480 0.0857 0.123 Uiso 1 1 calc R . . H36C H 0.5589 0.3015 0.1948 0.123 Uiso 1 1 calc R . . B1 B 0.5430(4) 0.4005(3) -0.2295(4) 0.0292(9) Uani 1 1 d . . . F1 F 0.6360(3) 0.40787(17) -0.1263(2) 0.0590(8) Uani 1 1 d . . . F2 F 0.5855(3) 0.44796(18) -0.3168(2) 0.0513(7) Uani 1 1 d . . . F3 F 0.5309(2) 0.31173(14) -0.2607(2) 0.0371(6) Uani 1 1 d . . . F4 F 0.4229(3) 0.43248(19) -0.2135(3) 0.0552(8) 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 Rh1 0.01777(11) 0.01540(11) 0.01580(10) -0.00074(12) 0.00129(7) 0.00117(11) P1 0.0188(4) 0.0151(4) 0.0180(4) 0.0001(3) 0.0045(3) 0.0003(3) P2 0.0182(4) 0.0162(4) 0.0163(4) -0.0007(3) 0.0023(3) -0.0015(3) O1 0.0247(12) 0.0247(14) 0.0297(13) 0.0000(11) 0.0080(10) -0.0014(10) O2 0.0311(13) 0.0207(13) 0.0230(12) 0.0006(10) 0.0053(10) -0.0044(10) C1 0.0217(17) 0.0229(18) 0.0226(16) 0.0035(14) 0.0000(13) -0.0002(14) C2 0.0235(15) 0.022(2) 0.0183(14) 0.0011(13) -0.0003(12) -0.0029(13) C3 0.0201(15) 0.025(2) 0.0314(17) 0.0044(15) 0.0022(13) -0.0017(13) C4 0.0259(18) 0.0228(19) 0.0281(19) 0.0049(15) 0.0028(14) 0.0043(15) C5 0.0282(19) 0.0186(18) 0.0205(17) 0.0019(14) 0.0005(14) 0.0013(14) C6 0.034(2) 0.0198(19) 0.0223(17) 0.0026(15) 0.0024(15) -0.0046(15) C7 0.0208(16) 0.0184(17) 0.0182(15) 0.0034(13) 0.0045(13) -0.0004(13) C8 0.029(2) 0.023(2) 0.0246(19) -0.0012(16) 0.0071(15) -0.0008(16) C9 0.0258(18) 0.025(2) 0.0309(19) 0.0020(16) 0.0084(15) -0.0028(15) C10 0.0269(18) 0.0221(19) 0.032(2) 0.0009(16) -0.0013(15) -0.0102(15) C11 0.038(2) 0.0199(18) 0.0237(17) -0.0023(15) 0.0053(15) -0.0055(15) C12 0.0273(18) 0.0186(17) 0.0223(17) -0.0009(14) 0.0087(14) -0.0007(14) C13 0.0173(16) 0.0215(18) 0.0215(16) -0.0013(14) 0.0047(12) -0.0007(13) C14 0.0246(18) 0.0248(19) 0.0322(19) 0.0028(16) 0.0089(15) 0.0047(15) C15 0.028(2) 0.034(2) 0.041(2) -0.0085(18) 0.0141(17) 0.0057(17) C16 0.0252(19) 0.041(2) 0.0302(19) -0.0057(18) 0.0146(15) -0.0036(17) C17 0.031(2) 0.028(2) 0.031(2) 0.0020(17) 0.0113(16) -0.0033(16) C18 0.0283(18) 0.0199(18) 0.0261(18) 0.0006(15) 0.0080(14) -0.0003(14) C19 0.0199(16) 0.0202(18) 0.0185(15) 0.0007(14) -0.0023(12) 0.0010(13) C20 0.043(2) 0.028(2) 0.0246(19) -0.0049(16) 0.0096(17) -0.0077(17) C21 0.059(3) 0.026(2) 0.040(2) -0.0093(19) 0.012(2) -0.010(2) C22 0.037(2) 0.0209(19) 0.039(2) 0.0023(17) -0.0035(17) -0.0077(16) C23 0.0238(18) 0.028(2) 0.031(2) 0.0107(17) 0.0027(15) -0.0006(15) C24 0.0278(19) 0.0206(19) 0.0235(17) 0.0053(15) 0.0044(14) 0.0000(15) C25 0.0290(17) 0.0170(15) 0.0219(16) -0.0033(13) 0.0087(13) -0.0044(14) C26 0.0301(18) 0.041(2) 0.0220(17) -0.0045(15) 0.0068(14) -0.0054(16) C27 0.047(2) 0.043(2) 0.0225(19) -0.0049(17) 0.0161(17) -0.0086(19) C28 0.043(2) 0.022(2) 0.036(2) -0.0009(17) 0.0224(18) 0.0005(17) C29 0.0281(19) 0.026(2) 0.045(2) 0.0064(17) 0.0154(17) 0.0028(16) C30 0.0264(18) 0.0251(18) 0.0290(19) 0.0068(16) 0.0064(15) -0.0034(15) N1 0.0205(14) 0.0247(17) 0.0212(14) -0.0003(12) 0.0018(11) 0.0039(12) C31 0.030(2) 0.025(2) 0.0195(17) -0.0008(15) 0.0035(15) 0.0040(16) C32 0.056(3) 0.030(2) 0.041(2) 0.0027(19) 0.016(2) 0.018(2) N2 0.0210(13) 0.0249(19) 0.0196(13) 0.0013(12) 0.0005(10) 0.0000(11) C33 0.0245(17) 0.0224(19) 0.0219(17) 0.0010(14) 0.0012(14) 0.0011(14) C34 0.049(2) 0.025(2) 0.028(2) 0.0028(17) -0.0130(17) -0.0019(18) N3 0.076(4) 0.082(4) 0.121(5) 0.018(4) 0.053(4) 0.002(3) C35 0.041(3) 0.088(5) 0.067(4) 0.021(4) 0.027(3) 0.005(3) C36 0.060(3) 0.123(6) 0.066(3) -0.020(5) 0.019(3) -0.022(5) B1 0.025(2) 0.029(2) 0.033(2) -0.001(2) 0.0050(17) -0.0007(18) F1 0.0783(19) 0.0371(16) 0.0482(16) -0.0138(13) -0.0232(14) 0.0048(15) F2 0.0540(16) 0.0489(16) 0.0584(17) 0.0068(13) 0.0298(14) -0.0073(13) F3 0.0409(12) 0.0255(15) 0.0391(12) -0.0076(10) -0.0079(9) 0.0002(9) F4 0.0422(14) 0.0470(17) 0.086(2) 0.0104(15) 0.0359(15) 0.0157(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 Rh1 N1 2.068(3) . ? Rh1 N2 2.069(3) . ? Rh1 P2 2.2398(9) . ? Rh1 P1 2.2503(9) . ? P1 C13 1.829(3) . ? P1 C5 1.853(4) . ? P1 C7 1.853(3) . ? P2 C25 1.834(3) . ? P2 C19 1.840(4) . ? P2 C2 1.850(3) . ? O1 C3 1.428(4) . ? O1 C4 1.434(4) . ? O2 C6 1.434(4) . ? O2 C1 1.438(4) . ? C1 C4 1.541(5) . ? C1 C2 1.545(5) . ? C2 C3 1.523(4) . ? C4 C5 1.539(5) . ? C5 C6 1.522(5) . ? C7 C12 1.394(5) . ? C7 C8 1.397(5) . ? C8 C9 1.395(5) . ? C9 C10 1.382(5) . ? C10 C11 1.380(5) . ? C11 C12 1.395(5) . ? C13 C14 1.396(5) . ? C13 C18 1.397(5) . ? C14 C15 1.380(5) . ? C15 C16 1.388(6) . ? C16 C17 1.386(5) . ? C17 C18 1.398(5) . ? C19 C20 1.389(5) . ? C19 C24 1.397(5) . ? C20 C21 1.393(6) . ? C21 C22 1.368(6) . ? C22 C23 1.385(6) . ? C23 C24 1.382(5) . ? C25 C26 1.392(5) . ? C25 C30 1.395(5) . ? C26 C27 1.375(5) . ? C27 C28 1.396(6) . ? C28 C29 1.377(6) . ? C29 C30 1.387(5) . ? N1 C31 1.140(5) . ? C31 C32 1.451(6) . ? N2 C33 1.135(4) . ? C33 C34 1.453(5) . ? N3 C35 1.144(8) . ? C35 C36 1.456(10) . ? B1 F4 1.370(5) . ? B1 F2 1.377(5) . ? B1 F1 1.390(5) . ? B1 F3 1.392(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Rh1 N2 88.39(11) . . ? N1 Rh1 P2 87.21(8) . . ? N2 Rh1 P2 174.82(8) . . ? N1 Rh1 P1 174.09(8) . . ? N2 Rh1 P1 85.84(8) . . ? P2 Rh1 P1 98.61(3) . . ? C13 P1 C5 103.32(16) . . ? C13 P1 C7 103.87(15) . . ? C5 P1 C7 99.39(15) . . ? C13 P1 Rh1 112.48(11) . . ? C5 P1 Rh1 127.01(12) . . ? C7 P1 Rh1 107.99(11) . . ? C25 P2 C19 102.99(15) . . ? C25 P2 C2 104.14(15) . . ? C19 P2 C2 98.97(15) . . ? C25 P2 Rh1 113.34(12) . . ? C19 P2 Rh1 108.32(11) . . ? C2 P2 Rh1 126.04(11) . . ? C3 O1 C4 107.9(3) . . ? C6 O2 C1 106.8(3) . . ? O2 C1 C4 107.0(3) . . ? O2 C1 C2 111.6(3) . . ? C4 C1 C2 104.2(3) . . ? C3 C2 C1 101.0(3) . . ? C3 C2 P2 112.8(2) . . ? C1 C2 P2 113.4(2) . . ? O1 C3 C2 106.3(3) . . ? O1 C4 C5 113.4(3) . . ? O1 C4 C1 107.4(3) . . ? C5 C4 C1 104.5(3) . . ? C6 C5 C4 100.5(3) . . ? C6 C5 P1 113.4(2) . . ? C4 C5 P1 112.8(2) . . ? O2 C6 C5 105.5(3) . . ? C12 C7 C8 118.6(3) . . ? C12 C7 P1 124.2(2) . . ? C8 C7 P1 117.1(3) . . ? C9 C8 C7 120.8(3) . . ? C10 C9 C8 119.8(3) . . ? C11 C10 C9 120.2(3) . . ? C10 C11 C12 120.2(3) . . ? C7 C12 C11 120.4(3) . . ? C14 C13 C18 117.9(3) . . ? C14 C13 P1 123.0(3) . . ? C18 C13 P1 119.0(2) . . ? C15 C14 C13 120.7(3) . . ? C14 C15 C16 121.0(4) . . ? C17 C16 C15 119.6(3) . . ? C16 C17 C18 119.3(3) . . ? C13 C18 C17 121.5(3) . . ? C20 C19 C24 118.3(3) . . ? C20 C19 P2 123.5(3) . . ? C24 C19 P2 118.3(3) . . ? C19 C20 C21 119.9(4) . . ? C22 C21 C20 121.3(4) . . ? C21 C22 C23 119.4(4) . . ? C24 C23 C22 119.9(3) . . ? C23 C24 C19 121.2(3) . . ? C26 C25 C30 118.7(3) . . ? C26 C25 P2 123.1(3) . . ? C30 C25 P2 118.1(3) . . ? C27 C26 C25 120.7(4) . . ? C26 C27 C28 120.3(4) . . ? C29 C28 C27 119.5(3) . . ? C28 C29 C30 120.2(4) . . ? C29 C30 C25 120.5(4) . . ? C31 N1 Rh1 175.0(3) . . ? N1 C31 C32 178.1(4) . . ? C33 N2 Rh1 165.4(3) . . ? N2 C33 C34 174.3(4) . . ? N3 C35 C36 178.9(7) . . ? F4 B1 F2 109.4(4) . . ? F4 B1 F1 110.4(4) . . ? F2 B1 F1 109.3(3) . . ? F4 B1 F3 109.7(3) . . ? F2 B1 F3 109.7(4) . . ? F1 B1 F3 108.4(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 N1 Rh1 P1 C13 59.0(8) . . . . ? N2 Rh1 P1 C13 71.24(14) . . . . ? P2 Rh1 P1 C13 -111.43(12) . . . . ? N1 Rh1 P1 C5 -172.4(8) . . . . ? N2 Rh1 P1 C5 -160.15(16) . . . . ? P2 Rh1 P1 C5 17.18(15) . . . . ? N1 Rh1 P1 C7 -55.0(8) . . . . ? N2 Rh1 P1 C7 -42.79(13) . . . . ? P2 Rh1 P1 C7 134.54(11) . . . . ? N1 Rh1 P2 C25 72.34(15) . . . . ? N2 Rh1 P2 C25 40.4(9) . . . . ? P1 Rh1 P2 C25 -108.64(13) . . . . ? N1 Rh1 P2 C19 -41.29(14) . . . . ? N2 Rh1 P2 C19 -73.2(9) . . . . ? P1 Rh1 P2 C19 137.73(11) . . . . ? N1 Rh1 P2 C2 -157.65(15) . . . . ? N2 Rh1 P2 C2 170.4(9) . . . . ? P1 Rh1 P2 C2 21.37(13) . . . . ? C6 O2 C1 C4 19.2(3) . . . . ? C6 O2 C1 C2 132.7(3) . . . . ? O2 C1 C2 C3 -141.3(3) . . . . ? C4 C1 C2 C3 -26.2(3) . . . . ? O2 C1 C2 P2 -20.4(3) . . . . ? C4 C1 C2 P2 94.7(3) . . . . ? C25 P2 C2 C3 -175.3(2) . . . . ? C19 P2 C2 C3 -69.4(3) . . . . ? Rh1 P2 C2 C3 51.2(3) . . . . ? C25 P2 C2 C1 70.7(3) . . . . ? C19 P2 C2 C1 176.6(2) . . . . ? Rh1 P2 C2 C1 -62.8(3) . . . . ? C4 O1 C3 C2 -33.2(3) . . . . ? C1 C2 C3 O1 36.6(3) . . . . ? P2 C2 C3 O1 -84.7(3) . . . . ? C3 O1 C4 C5 130.2(3) . . . . ? C3 O1 C4 C1 15.2(3) . . . . ? O2 C1 C4 O1 126.4(3) . . . . ? C2 C1 C4 O1 8.1(3) . . . . ? O2 C1 C4 C5 5.7(3) . . . . ? C2 C1 C4 C5 -112.7(3) . . . . ? O1 C4 C5 C6 -143.0(3) . . . . ? C1 C4 C5 C6 -26.3(3) . . . . ? O1 C4 C5 P1 -21.9(4) . . . . ? C1 C4 C5 P1 94.8(3) . . . . ? C13 P1 C5 C6 -174.3(2) . . . . ? C7 P1 C5 C6 -67.5(3) . . . . ? Rh1 P1 C5 C6 53.6(3) . . . . ? C13 P1 C5 C4 72.2(3) . . . . ? C7 P1 C5 C4 179.0(2) . . . . ? Rh1 P1 C5 C4 -59.9(3) . . . . ? C1 O2 C6 C5 -37.3(3) . . . . ? C4 C5 C6 O2 39.1(3) . . . . ? P1 C5 C6 O2 -81.6(3) . . . . ? C13 P1 C7 C12 15.3(3) . . . . ? C5 P1 C7 C12 -91.1(3) . . . . ? Rh1 P1 C7 C12 134.9(3) . . . . ? C13 P1 C7 C8 -162.3(3) . . . . ? C5 P1 C7 C8 91.4(3) . . . . ? Rh1 P1 C7 C8 -42.6(3) . . . . ? C12 C7 C8 C9 0.2(5) . . . . ? P1 C7 C8 C9 177.9(3) . . . . ? C7 C8 C9 C10 -1.1(6) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C8 C7 C12 C11 1.1(5) . . . . ? P1 C7 C12 C11 -176.4(3) . . . . ? C10 C11 C12 C7 -1.6(5) . . . . ? C5 P1 C13 C14 31.0(3) . . . . ? C7 P1 C13 C14 -72.4(3) . . . . ? Rh1 P1 C13 C14 171.1(3) . . . . ? C5 P1 C13 C18 -149.7(3) . . . . ? C7 P1 C13 C18 106.9(3) . . . . ? Rh1 P1 C13 C18 -9.6(3) . . . . ? C18 C13 C14 C15 -1.0(5) . . . . ? P1 C13 C14 C15 178.3(3) . . . . ? C13 C14 C15 C16 0.8(6) . . . . ? C14 C15 C16 C17 -0.5(6) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C14 C13 C18 C17 0.9(5) . . . . ? P1 C13 C18 C17 -178.4(3) . . . . ? C16 C17 C18 C13 -0.6(5) . . . . ? C25 P2 C19 C20 13.4(3) . . . . ? C2 P2 C19 C20 -93.5(3) . . . . ? Rh1 P2 C19 C20 133.7(3) . . . . ? C25 P2 C19 C24 -166.2(3) . . . . ? C2 P2 C19 C24 87.0(3) . . . . ? Rh1 P2 C19 C24 -45.8(3) . . . . ? C24 C19 C20 C21 1.4(6) . . . . ? P2 C19 C20 C21 -178.2(3) . . . . ? C19 C20 C21 C22 -1.8(7) . . . . ? C20 C21 C22 C23 -0.2(7) . . . . ? C21 C22 C23 C24 2.5(6) . . . . ? C22 C23 C24 C19 -2.9(5) . . . . ? C20 C19 C24 C23 0.9(5) . . . . ? P2 C19 C24 C23 -179.5(3) . . . . ? C19 P2 C25 C26 -79.4(3) . . . . ? C2 P2 C25 C26 23.5(3) . . . . ? Rh1 P2 C25 C26 163.8(3) . . . . ? C19 P2 C25 C30 98.5(3) . . . . ? C2 P2 C25 C30 -158.6(3) . . . . ? Rh1 P2 C25 C30 -18.3(3) . . . . ? C30 C25 C26 C27 -1.3(6) . . . . ? P2 C25 C26 C27 176.6(3) . . . . ? C25 C26 C27 C28 -1.3(6) . . . . ? C26 C27 C28 C29 2.5(6) . . . . ? C27 C28 C29 C30 -1.1(6) . . . . ? C28 C29 C30 C25 -1.5(6) . . . . ? C26 C25 C30 C29 2.7(5) . . . . ? P2 C25 C30 C29 -175.3(3) . . . . ? N2 Rh1 N1 C31 -137(3) . . . . ? P2 Rh1 N1 C31 46(3) . . . . ? P1 Rh1 N1 C31 -124(3) . . . . ? Rh1 N1 C31 C32 -28(15) . . . . ? N1 Rh1 N2 C33 -139.5(11) . . . . ? P2 Rh1 N2 C33 -107.6(13) . . . . ? P1 Rh1 N2 C33 41.7(11) . . . . ? Rh1 N2 C33 C34 -8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.491 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.070 data_ddppm _database_code_depnum_ccdc_archive 'CCDC 230133' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 O2 P2' _chemical_formula_sum 'C30 H28 O2 P2' _chemical_formula_weight 482.46 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.5522(9) _cell_length_b 14.0034(11) _cell_length_c 15.4518(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2499.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 'all obs. reflections in the data set' _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 24.78 _exptl_crystal_description needle-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius kappa CCD area detector' _diffrn_measurement_method 'phi & omega scan to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24363 _diffrn_reflns_av_R_equivalents 0.2142 _diffrn_reflns_av_sigmaI/netI 0.1577 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 24.78 _reflns_number_total 4278 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^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 'calculated positions, riding model' _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 0.14(19) _refine_ls_number_reflns 4278 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1324 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1602 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.07367(13) 0.35225(12) 0.03932(10) 0.0421(4) Uani 1 1 d . . . P2 P 0.03722(14) -0.05011(12) -0.07253(10) 0.0432(5) Uani 1 1 d . . . O1 O 0.0717(4) 0.2308(3) -0.1183(3) 0.0527(12) Uani 1 1 d . . . O2 O -0.0906(4) 0.1068(3) 0.0161(3) 0.0551(13) Uani 1 1 d . . . C1 C -0.0817(5) 0.1280(4) -0.0724(4) 0.0431(15) Uani 1 1 d . . . H1 H -0.1585 0.1196 -0.1012 0.052 Uiso 1 1 calc R . . C2 C 0.0113(5) 0.0703(4) -0.1202(4) 0.0380(15) Uani 1 1 d . . . H2 H -0.0118 0.0630 -0.1822 0.046 Uiso 1 1 calc R . . C3 C 0.1158(5) 0.1380(5) -0.1145(4) 0.0448(16) Uani 1 1 d . . . H3A H 0.1580 0.1280 -0.0595 0.054 Uiso 1 1 calc R . . H3B H 0.1696 0.1265 -0.1632 0.054 Uiso 1 1 calc R . . C4 C -0.0412(5) 0.2324(4) -0.0805(4) 0.0432(16) Uani 1 1 d . . . H4 H -0.0959 0.2696 -0.1177 0.052 Uiso 1 1 calc R . . C5 C -0.0442(5) 0.2697(4) 0.0130(4) 0.0467(16) Uani 1 1 d . . . H5 H -0.1203 0.3015 0.0242 0.056 Uiso 1 1 calc R . . C6 C -0.0374(6) 0.1762(5) 0.0649(4) 0.060(2) Uani 1 1 d . . . H6A H 0.0444 0.1588 0.0759 0.072 Uiso 1 1 calc R . . H6B H -0.0773 0.1834 0.1212 0.072 Uiso 1 1 calc R . . C7 C 0.0283(5) 0.3966(4) 0.1457(4) 0.0383(15) Uani 1 1 d . . . C8 C 0.1118(5) 0.4502(5) 0.1928(5) 0.0513(17) Uani 1 1 d . . . H8 H 0.1844 0.4651 0.1673 0.062 Uiso 1 1 calc R . . C9 C 0.0870(6) 0.4806(5) 0.2758(4) 0.0526(18) Uani 1 1 d . . . H9 H 0.1428 0.5171 0.3065 0.063 Uiso 1 1 calc R . . C10 C -0.0138(7) 0.4599(5) 0.3141(4) 0.061(2) Uani 1 1 d . . . H10 H -0.0287 0.4818 0.3712 0.073 Uiso 1 1 calc R . . C11 C -0.0939(7) 0.4082(5) 0.2718(4) 0.059(2) Uani 1 1 d . . . H11 H -0.1650 0.3936 0.2996 0.071 Uiso 1 1 calc R . . C12 C -0.0745(5) 0.3760(5) 0.1890(4) 0.0480(17) Uani 1 1 d . . . H12 H -0.1323 0.3391 0.1608 0.058 Uiso 1 1 calc R . . C13 C 0.0383(5) 0.4568(4) -0.0297(3) 0.0376(14) Uani 1 1 d . . . C14 C -0.0585(5) 0.5141(5) -0.0187(4) 0.0469(17) Uani 1 1 d . . . H14 H -0.1134 0.4983 0.0247 0.056 Uiso 1 1 calc R . . C15 C -0.0769(6) 0.5947(5) -0.0705(5) 0.061(2) Uani 1 1 d . . . H15 H -0.1435 0.6335 -0.0626 0.073 Uiso 1 1 calc R . . C16 C 0.0043(6) 0.6167(5) -0.1337(4) 0.0500(18) Uani 1 1 d . . . H16 H -0.0055 0.6716 -0.1690 0.060 Uiso 1 1 calc R . . C17 C 0.0980(6) 0.5590(5) -0.1447(4) 0.0487(17) Uani 1 1 d . . . H17 H 0.1535 0.5737 -0.1881 0.058 Uiso 1 1 calc R . . C18 C 0.1133(5) 0.4793(4) -0.0935(3) 0.0412(16) Uani 1 1 d . . . H18 H 0.1783 0.4392 -0.1034 0.049 Uiso 1 1 calc R . . C19 C 0.1417(5) -0.1003(5) -0.1490(4) 0.0433(16) Uani 1 1 d . . . C20 C 0.2134(6) -0.1714(5) -0.1143(5) 0.056(2) Uani 1 1 d . . . H20 H 0.2049 -0.1897 -0.0554 0.068 Uiso 1 1 calc R . . C21 C 0.2968(6) -0.2151(6) -0.1654(7) 0.070(2) Uani 1 1 d . . . H21 H 0.3444 -0.2638 -0.1416 0.084 Uiso 1 1 calc R . . C22 C 0.3103(6) -0.1894(6) -0.2467(6) 0.068(2) Uani 1 1 d . . . H22 H 0.3680 -0.2200 -0.2807 0.082 Uiso 1 1 calc R . . C23 C 0.2425(5) -0.1189(5) -0.2838(5) 0.0519(19) Uani 1 1 d . . . H23 H 0.2537 -0.1011 -0.3425 0.062 Uiso 1 1 calc R . . C24 C 0.1580(6) -0.0744(4) -0.2342(4) 0.0475(18) Uani 1 1 d . . . H24 H 0.1111 -0.0259 -0.2591 0.057 Uiso 1 1 calc R . . C25 C -0.0994(5) -0.1070(4) -0.1061(4) 0.0399(16) Uani 1 1 d . . . C26 C -0.1218(5) -0.1447(4) -0.1886(4) 0.0410(15) Uani 1 1 d . . . H26 H -0.0631 -0.1430 -0.2317 0.049 Uiso 1 1 calc R . . C27 C -0.2272(5) -0.1839(5) -0.2077(4) 0.0494(18) Uani 1 1 d . . . H27 H -0.2412 -0.2095 -0.2637 0.059 Uiso 1 1 calc R . . C28 C -0.3132(6) -0.1865(5) -0.1456(5) 0.056(2) Uani 1 1 d . . . H28 H -0.3868 -0.2126 -0.1595 0.067 Uiso 1 1 calc R . . C29 C -0.2928(5) -0.1514(5) -0.0635(5) 0.0532(18) Uani 1 1 d . . . H29 H -0.3516 -0.1542 -0.0206 0.064 Uiso 1 1 calc R . . C30 C -0.1875(5) -0.1126(4) -0.0447(4) 0.0447(16) Uani 1 1 d . . . H30 H -0.1738 -0.0887 0.0119 0.054 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 0.0412(9) 0.0442(10) 0.0408(9) 0.0002(8) 0.0044(8) 0.0034(8) P2 0.0478(11) 0.0440(10) 0.0377(9) -0.0033(8) -0.0011(8) 0.0043(9) O1 0.067(3) 0.045(3) 0.046(3) -0.006(2) 0.015(2) -0.020(2) O2 0.091(3) 0.034(2) 0.040(3) -0.005(2) 0.019(2) -0.007(2) C1 0.046(4) 0.040(4) 0.044(4) -0.010(3) -0.006(3) 0.002(3) C2 0.044(4) 0.032(4) 0.037(3) -0.006(3) -0.004(3) 0.002(3) C3 0.043(4) 0.047(4) 0.045(4) -0.009(3) 0.012(3) 0.005(3) C4 0.048(4) 0.036(4) 0.046(4) 0.000(3) 0.001(3) 0.007(3) C5 0.052(4) 0.049(4) 0.039(4) -0.006(3) 0.004(3) -0.007(3) C6 0.076(5) 0.066(5) 0.037(4) 0.003(4) 0.004(4) -0.019(4) C7 0.045(4) 0.032(4) 0.038(3) -0.006(3) 0.007(3) -0.006(3) C8 0.040(4) 0.040(4) 0.074(5) 0.013(4) 0.010(3) 0.001(3) C9 0.048(4) 0.063(5) 0.047(4) -0.020(3) -0.011(4) 0.005(4) C10 0.084(6) 0.062(5) 0.037(4) -0.007(4) 0.009(4) -0.005(5) C11 0.067(5) 0.054(5) 0.057(5) -0.002(4) 0.026(4) -0.003(4) C12 0.038(3) 0.054(5) 0.052(4) -0.019(3) 0.002(3) -0.008(3) C13 0.046(4) 0.035(3) 0.033(3) -0.003(3) -0.004(3) -0.003(3) C14 0.042(4) 0.060(5) 0.039(4) 0.000(3) 0.004(3) 0.001(3) C15 0.056(4) 0.077(5) 0.050(4) -0.022(4) -0.016(4) 0.028(4) C16 0.066(5) 0.049(5) 0.035(4) 0.007(3) -0.008(3) 0.001(4) C17 0.051(4) 0.059(5) 0.036(4) 0.008(3) -0.001(3) -0.006(4) C18 0.043(4) 0.047(4) 0.033(4) 0.002(3) 0.000(3) -0.003(3) C19 0.038(4) 0.035(4) 0.057(5) -0.007(3) 0.001(3) 0.000(3) C20 0.058(5) 0.050(5) 0.061(5) 0.006(4) -0.011(4) -0.009(4) C21 0.043(4) 0.053(5) 0.115(8) -0.007(5) -0.006(5) 0.018(4) C22 0.052(5) 0.060(6) 0.093(7) -0.018(5) 0.028(5) -0.002(4) C23 0.048(4) 0.052(5) 0.056(5) -0.013(4) 0.018(4) -0.003(4) C24 0.057(4) 0.035(4) 0.051(4) 0.000(3) -0.002(3) 0.007(3) C25 0.044(4) 0.033(4) 0.043(4) 0.004(3) 0.008(3) 0.006(3) C26 0.043(4) 0.040(4) 0.040(4) -0.001(3) 0.008(3) 0.006(3) C27 0.044(4) 0.052(5) 0.052(5) -0.010(4) -0.001(4) -0.001(3) C28 0.038(4) 0.050(5) 0.080(6) -0.014(4) 0.011(4) -0.008(3) C29 0.051(4) 0.044(4) 0.064(5) -0.002(4) 0.020(4) -0.001(4) C30 0.055(4) 0.035(4) 0.044(4) 0.001(3) 0.019(3) 0.014(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 P1 C5 1.832(6) . ? P1 C7 1.833(6) . ? P1 C13 1.856(6) . ? P2 C19 1.830(6) . ? P2 C25 1.842(6) . ? P2 C2 1.865(6) . ? O1 C3 1.397(7) . ? O1 C4 1.430(7) . ? O2 C6 1.375(7) . ? O2 C1 1.402(7) . ? C1 C2 1.534(8) . ? C1 C4 1.540(8) . ? C2 C3 1.537(8) . ? C4 C5 1.537(7) . ? C5 C6 1.538(8) . ? C7 C12 1.393(8) . ? C7 C8 1.424(8) . ? C8 C9 1.381(8) . ? C9 C10 1.337(9) . ? C10 C11 1.345(9) . ? C11 C12 1.375(8) . ? C13 C18 1.350(7) . ? C13 C14 1.386(8) . ? C14 C15 1.400(9) . ? C15 C16 1.388(9) . ? C16 C17 1.362(8) . ? C17 C18 1.378(8) . ? C19 C24 1.378(8) . ? C19 C20 1.402(9) . ? C20 C21 1.388(10) . ? C21 C22 1.315(10) . ? C22 C23 1.386(10) . ? C23 C24 1.389(8) . ? C25 C30 1.394(7) . ? C25 C26 1.404(8) . ? C26 C27 1.367(8) . ? C27 C28 1.382(9) . ? C28 C29 1.380(9) . ? C29 C30 1.364(8) . ? 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 C5 P1 C7 101.5(3) . . ? C5 P1 C13 101.9(3) . . ? C7 P1 C13 100.7(3) . . ? C19 P2 C25 102.5(3) . . ? C19 P2 C2 101.4(3) . . ? C25 P2 C2 98.2(3) . . ? C3 O1 C4 109.2(4) . . ? C6 O2 C1 110.6(5) . . ? O2 C1 C2 114.2(5) . . ? O2 C1 C4 107.6(5) . . ? C2 C1 C4 104.4(5) . . ? C1 C2 C3 101.4(4) . . ? C1 C2 P2 113.5(4) . . ? C3 C2 P2 114.1(4) . . ? O1 C3 C2 106.6(5) . . ? O1 C4 C5 114.2(5) . . ? O1 C4 C1 107.2(4) . . ? C5 C4 C1 103.9(5) . . ? C4 C5 C6 101.5(5) . . ? C4 C5 P1 114.0(4) . . ? C6 C5 P1 112.6(4) . . ? O2 C6 C5 107.1(5) . . ? C12 C7 C8 116.2(5) . . ? C12 C7 P1 127.2(5) . . ? C8 C7 P1 116.4(5) . . ? C9 C8 C7 119.8(6) . . ? C10 C9 C8 121.7(6) . . ? C9 C10 C11 120.0(7) . . ? C10 C11 C12 121.1(7) . . ? C11 C12 C7 121.2(6) . . ? C18 C13 C14 118.1(6) . . ? C18 C13 P1 117.6(5) . . ? C14 C13 P1 124.3(5) . . ? C13 C14 C15 121.3(6) . . ? C16 C15 C14 118.6(6) . . ? C17 C16 C15 119.6(6) . . ? C16 C17 C18 120.6(6) . . ? C13 C18 C17 121.8(6) . . ? C24 C19 C20 118.2(6) . . ? C24 C19 P2 127.3(5) . . ? C20 C19 P2 114.5(5) . . ? C21 C20 C19 120.3(7) . . ? C22 C21 C20 120.4(8) . . ? C21 C22 C23 121.5(7) . . ? C22 C23 C24 119.3(7) . . ? C19 C24 C23 120.3(6) . . ? C30 C25 C26 117.5(6) . . ? C30 C25 P2 117.2(5) . . ? C26 C25 P2 125.2(4) . . ? C27 C26 C25 120.8(6) . . ? C26 C27 C28 120.0(6) . . ? C29 C28 C27 120.4(6) . . ? C30 C29 C28 119.3(6) . . ? C29 C30 C25 121.9(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O2 C1 C2 102.1(6) . . . . ? C6 O2 C1 C4 -13.2(7) . . . . ? O2 C1 C2 C3 -93.2(6) . . . . ? C4 C1 C2 C3 23.9(6) . . . . ? O2 C1 C2 P2 29.6(6) . . . . ? C4 C1 C2 P2 146.7(4) . . . . ? C19 P2 C2 C1 175.8(4) . . . . ? C25 P2 C2 C1 71.2(4) . . . . ? C19 P2 C2 C3 -68.7(5) . . . . ? C25 P2 C2 C3 -173.3(4) . . . . ? C4 O1 C3 C2 30.8(6) . . . . ? C1 C2 C3 O1 -33.8(6) . . . . ? P2 C2 C3 O1 -156.2(4) . . . . ? C3 O1 C4 C5 100.0(5) . . . . ? C3 O1 C4 C1 -14.5(6) . . . . ? O2 C1 C4 O1 114.1(5) . . . . ? C2 C1 C4 O1 -7.5(6) . . . . ? O2 C1 C4 C5 -7.1(6) . . . . ? C2 C1 C4 C5 -128.7(5) . . . . ? O1 C4 C5 C6 -94.6(6) . . . . ? C1 C4 C5 C6 21.8(6) . . . . ? O1 C4 C5 P1 26.7(6) . . . . ? C1 C4 C5 P1 143.1(4) . . . . ? C7 P1 C5 C4 170.6(4) . . . . ? C13 P1 C5 C4 66.9(5) . . . . ? C7 P1 C5 C6 -74.6(5) . . . . ? C13 P1 C5 C6 -178.2(4) . . . . ? C1 O2 C6 C5 28.3(7) . . . . ? C4 C5 C6 O2 -30.8(7) . . . . ? P1 C5 C6 O2 -153.1(4) . . . . ? C5 P1 C7 C12 -4.4(6) . . . . ? C13 P1 C7 C12 100.2(6) . . . . ? C5 P1 C7 C8 169.0(5) . . . . ? C13 P1 C7 C8 -86.4(5) . . . . ? C12 C7 C8 C9 -1.6(9) . . . . ? P1 C7 C8 C9 -175.7(5) . . . . ? C7 C8 C9 C10 0.9(10) . . . . ? C8 C9 C10 C11 0.1(11) . . . . ? C9 C10 C11 C12 -0.3(11) . . . . ? C10 C11 C12 C7 -0.6(11) . . . . ? C8 C7 C12 C11 1.4(9) . . . . ? P1 C7 C12 C11 174.8(5) . . . . ? C5 P1 C13 C18 -115.0(5) . . . . ? C7 P1 C13 C18 140.6(5) . . . . ? C5 P1 C13 C14 66.4(5) . . . . ? C7 P1 C13 C14 -38.0(5) . . . . ? C18 C13 C14 C15 -1.8(9) . . . . ? P1 C13 C14 C15 176.8(5) . . . . ? C13 C14 C15 C16 -0.1(9) . . . . ? C14 C15 C16 C17 1.1(9) . . . . ? C15 C16 C17 C18 -0.3(9) . . . . ? C14 C13 C18 C17 2.6(9) . . . . ? P1 C13 C18 C17 -176.1(5) . . . . ? C16 C17 C18 C13 -1.6(9) . . . . ? C25 P2 C19 C24 77.4(6) . . . . ? C2 P2 C19 C24 -23.7(6) . . . . ? C25 P2 C19 C20 -104.2(5) . . . . ? C2 P2 C19 C20 154.7(5) . . . . ? C24 C19 C20 C21 -1.1(10) . . . . ? P2 C19 C20 C21 -179.7(6) . . . . ? C19 C20 C21 C22 0.9(11) . . . . ? C20 C21 C22 C23 -0.1(12) . . . . ? C21 C22 C23 C24 -0.2(11) . . . . ? C20 C19 C24 C23 0.8(9) . . . . ? P2 C19 C24 C23 179.2(5) . . . . ? C22 C23 C24 C19 -0.1(10) . . . . ? C19 P2 C25 C30 157.3(5) . . . . ? C2 P2 C25 C30 -99.0(5) . . . . ? C19 P2 C25 C26 -23.0(6) . . . . ? C2 P2 C25 C26 80.7(5) . . . . ? C30 C25 C26 C27 1.0(9) . . . . ? P2 C25 C26 C27 -178.7(5) . . . . ? C25 C26 C27 C28 0.2(10) . . . . ? C26 C27 C28 C29 -1.3(10) . . . . ? C27 C28 C29 C30 1.1(10) . . . . ? C28 C29 C30 C25 0.2(10) . . . . ? C26 C25 C30 C29 -1.2(9) . . . . ? P2 C25 C30 C29 178.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.78 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.594 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.056 data_ddppg _database_code_depnum_ccdc_archive 'CCDC 230134' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 O2 P2' _chemical_formula_weight 482.46 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3120(4) _cell_length_b 10.1516(4) _cell_length_c 26.5195(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2506.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 'all obs. reflections in the data set' _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.35 _exptl_crystal_description needle-like _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius kappa CCD area detector' _diffrn_measurement_method 'phi & omega scan to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13050 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4394 _reflns_number_gt 3404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+1.2748P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(14) _refine_ls_number_reflns 4394 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.16161(11) 0.41354(10) 0.21284(4) 0.0294(3) Uani 1 1 d . . . P2 P -0.24689(12) 0.57640(10) 0.40698(4) 0.0314(3) Uani 1 1 d . . . O1 O 0.1398(3) 0.5516(3) 0.35351(10) 0.0447(8) Uani 1 1 d . . . O2 O -0.0869(3) 0.4097(3) 0.28441(10) 0.0354(7) Uani 1 1 d . . . C1 C 0.2131(4) 0.4913(4) 0.31249(15) 0.0378(11) Uani 1 1 d . . . H1A H 0.2131 0.3943 0.3162 0.045 Uiso 1 1 calc R . . H1B H 0.3139 0.5223 0.3109 0.045 Uiso 1 1 calc R . . C2 C 0.1311(4) 0.5322(4) 0.26481(14) 0.0286(9) Uani 1 1 d . . . H2 H 0.1629 0.6220 0.2540 0.034 Uiso 1 1 calc R . . C3 C -0.0229(4) 0.5390(4) 0.28440(16) 0.0321(10) Uani 1 1 d . . . H3 H -0.0822 0.6044 0.2654 0.039 Uiso 1 1 calc R . . C4 C -0.0070(4) 0.5762(4) 0.34015(14) 0.0301(9) Uani 1 1 d . . . H4 H -0.0314 0.6712 0.3454 0.036 Uiso 1 1 calc R . . C5 C -0.1146(4) 0.4879(4) 0.36773(15) 0.0317(10) Uani 1 1 d . . . H5 H -0.0613 0.4232 0.3891 0.038 Uiso 1 1 calc R . . C6 C -0.1891(4) 0.4148(5) 0.32454(15) 0.0391(10) Uani 1 1 d . . . H6A H -0.2166 0.3248 0.3352 0.047 Uiso 1 1 calc R . . H6B H -0.2766 0.4625 0.3138 0.047 Uiso 1 1 calc R . . C7 C 0.0917(4) 0.5009(3) 0.15721(15) 0.0259(9) Uani 1 1 d . . . C8 C 0.1236(5) 0.4446(4) 0.11060(16) 0.0378(11) Uani 1 1 d . . . H8 H 0.1835 0.3690 0.1092 0.045 Uiso 1 1 calc R . . C9 C 0.0695(5) 0.4973(5) 0.06637(17) 0.0446(12) Uani 1 1 d . . . H9 H 0.0937 0.4592 0.0348 0.054 Uiso 1 1 calc R . . C10 C -0.0205(5) 0.6063(4) 0.06849(16) 0.0399(11) Uani 1 1 d . . . H10 H -0.0599 0.6418 0.0384 0.048 Uiso 1 1 calc R . . C11 C -0.0522(5) 0.6621(4) 0.11380(17) 0.0347(10) Uani 1 1 d . . . H11 H -0.1141 0.7365 0.1151 0.042 Uiso 1 1 calc R . . C12 C 0.0049(4) 0.6116(4) 0.15844(16) 0.0308(9) Uani 1 1 d . . . H12 H -0.0157 0.6532 0.1897 0.037 Uiso 1 1 calc R . . C13 C 0.3566(4) 0.4347(4) 0.20465(13) 0.0285(9) Uani 1 1 d . . . C14 C 0.4431(5) 0.3312(4) 0.21851(19) 0.0453(12) Uani 1 1 d . . . H14 H 0.4014 0.2531 0.2317 0.054 Uiso 1 1 calc R . . C15 C 0.5906(6) 0.3403(5) 0.2134(2) 0.0621(15) Uani 1 1 d . . . H15 H 0.6493 0.2682 0.2233 0.075 Uiso 1 1 calc R . . C16 C 0.6537(5) 0.4525(5) 0.19420(18) 0.0529(13) Uani 1 1 d . . . H16 H 0.7551 0.4584 0.1909 0.064 Uiso 1 1 calc R . . C17 C 0.5674(5) 0.5556(5) 0.18001(17) 0.0446(12) Uani 1 1 d . . . H17 H 0.6095 0.6336 0.1668 0.054 Uiso 1 1 calc R . . C18 C 0.4201(5) 0.5472(4) 0.18466(16) 0.0372(11) Uani 1 1 d . . . H18 H 0.3617 0.6188 0.1741 0.045 Uiso 1 1 calc R . . C19 C -0.1521(5) 0.5944(4) 0.46759(15) 0.0318(9) Uani 1 1 d . . . C20 C -0.0039(5) 0.6040(4) 0.47232(17) 0.0406(11) Uani 1 1 d . . . H20 H 0.0556 0.5927 0.4436 0.049 Uiso 1 1 calc R . . C21 C 0.0569(5) 0.6300(4) 0.51871(17) 0.0427(12) Uani 1 1 d . . . H21 H 0.1582 0.6383 0.5216 0.051 Uiso 1 1 calc R . . C22 C -0.0277(6) 0.6437(4) 0.56057(18) 0.0459(13) Uani 1 1 d . . . H22 H 0.0152 0.6596 0.5925 0.055 Uiso 1 1 calc R . . C23 C -0.1735(6) 0.6346(4) 0.55667(18) 0.0469(12) Uani 1 1 d . . . H23 H -0.2319 0.6448 0.5858 0.056 Uiso 1 1 calc R . . C24 C -0.2360(5) 0.6106(4) 0.51050(16) 0.0401(10) Uani 1 1 d . . . H24 H -0.3376 0.6051 0.5080 0.048 Uiso 1 1 calc R . . C25 C -0.3725(4) 0.4419(4) 0.42204(13) 0.0276(9) Uani 1 1 d . . . C26 C -0.3284(5) 0.3154(4) 0.43532(16) 0.0394(11) Uani 1 1 d . . . H26 H -0.2288 0.2957 0.4376 0.047 Uiso 1 1 calc R . . C27 C -0.4277(5) 0.2189(4) 0.44512(17) 0.0455(12) Uani 1 1 d . . . H27 H -0.3959 0.1325 0.4532 0.055 Uiso 1 1 calc R . . C28 C -0.5713(5) 0.2451(5) 0.44351(17) 0.0473(12) Uani 1 1 d . . . H28 H -0.6385 0.1769 0.4503 0.057 Uiso 1 1 calc R . . C29 C -0.6198(5) 0.3712(4) 0.43198(17) 0.0452(12) Uani 1 1 d . . . H29 H -0.7197 0.3904 0.4319 0.054 Uiso 1 1 calc R . . C30 C -0.5207(5) 0.4682(4) 0.42065(15) 0.0356(11) Uani 1 1 d . . . H30 H -0.5531 0.5539 0.4118 0.043 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 0.0324(6) 0.0244(5) 0.0313(6) 0.0031(5) 0.0003(5) -0.0005(5) P2 0.0300(6) 0.0323(5) 0.0320(6) 0.0035(5) 0.0030(5) -0.0002(5) O1 0.0266(18) 0.074(2) 0.0334(17) -0.0058(15) 0.0018(14) 0.0007(15) O2 0.0323(15) 0.0369(15) 0.0371(16) -0.0046(14) 0.0091(14) -0.0046(13) C1 0.030(3) 0.050(3) 0.033(3) 0.004(2) 0.002(2) 0.003(2) C2 0.025(2) 0.028(2) 0.032(2) 0.0027(17) 0.0011(19) -0.0012(16) C3 0.031(2) 0.034(2) 0.032(2) 0.0076(19) 0.004(2) 0.0020(17) C4 0.025(2) 0.036(2) 0.030(2) 0.0022(19) 0.0017(18) 0.0004(19) C5 0.028(2) 0.035(2) 0.032(2) 0.0009(18) 0.0055(19) 0.0006(17) C6 0.031(2) 0.041(2) 0.045(3) -0.004(2) 0.008(2) -0.005(2) C7 0.022(2) 0.026(2) 0.029(2) 0.0015(17) 0.0011(18) -0.0052(17) C8 0.031(3) 0.043(2) 0.039(2) -0.003(2) 0.005(2) 0.0091(19) C9 0.040(3) 0.063(3) 0.031(3) -0.007(2) -0.003(2) 0.006(2) C10 0.036(3) 0.050(3) 0.034(3) 0.010(2) -0.009(2) -0.003(2) C11 0.033(3) 0.030(2) 0.041(3) 0.0090(19) -0.007(2) 0.0009(19) C12 0.032(2) 0.030(2) 0.031(2) 0.0030(18) -0.0016(19) -0.0026(18) C13 0.031(2) 0.033(2) 0.021(2) -0.0009(17) -0.0034(18) 0.0055(19) C14 0.044(3) 0.040(2) 0.052(3) 0.007(2) 0.000(3) 0.008(2) C15 0.047(4) 0.060(3) 0.079(4) 0.004(3) -0.003(3) 0.024(3) C16 0.027(3) 0.089(4) 0.042(3) -0.010(3) -0.004(2) -0.001(3) C17 0.039(3) 0.051(3) 0.044(3) 0.000(2) -0.001(2) -0.006(2) C18 0.040(3) 0.037(3) 0.035(2) 0.002(2) 0.003(2) 0.0027(19) C19 0.036(2) 0.0269(19) 0.033(2) -0.0005(18) -0.001(2) -0.002(2) C20 0.041(3) 0.039(2) 0.042(3) 0.005(2) 0.005(2) 0.001(2) C21 0.037(3) 0.045(3) 0.046(3) 0.012(2) -0.013(2) -0.007(2) C22 0.068(4) 0.034(2) 0.035(3) 0.000(2) -0.017(3) -0.013(2) C23 0.043(3) 0.054(3) 0.043(3) -0.003(2) 0.001(3) -0.003(2) C24 0.039(3) 0.039(2) 0.042(3) 0.000(2) 0.000(2) -0.005(2) C25 0.033(2) 0.030(2) 0.020(2) -0.0013(16) 0.0024(17) -0.0049(17) C26 0.043(3) 0.042(2) 0.034(3) 0.001(2) 0.008(2) 0.000(2) C27 0.051(3) 0.041(3) 0.045(3) 0.000(2) 0.006(2) -0.010(2) C28 0.048(3) 0.050(3) 0.044(3) -0.003(2) 0.004(2) -0.019(2) C29 0.034(3) 0.059(3) 0.043(3) -0.013(2) -0.002(2) -0.012(2) C30 0.044(3) 0.036(2) 0.027(2) -0.0006(18) -0.003(2) -0.002(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 P1 C7 1.840(4) . ? P1 C13 1.841(4) . ? P1 C2 1.853(4) . ? P2 C25 1.841(4) . ? P2 C19 1.843(4) . ? P2 C5 1.846(4) . ? O1 C1 1.422(5) . ? O1 C4 1.435(5) . ? O2 C6 1.428(5) . ? O2 C3 1.441(5) . ? C1 C2 1.535(5) . ? C2 C3 1.527(6) . ? C3 C4 1.533(6) . ? C4 C5 1.530(5) . ? C5 C6 1.531(6) . ? C7 C12 1.385(5) . ? C7 C8 1.394(5) . ? C8 C9 1.384(6) . ? C9 C10 1.389(6) . ? C10 C11 1.361(6) . ? C11 C12 1.396(6) . ? C13 C14 1.374(6) . ? C13 C18 1.391(6) . ? C14 C15 1.384(7) . ? C15 C16 1.380(7) . ? C16 C17 1.372(7) . ? C17 C18 1.380(6) . ? C19 C20 1.389(6) . ? C19 C24 1.390(6) . ? C20 C21 1.380(6) . ? C21 C22 1.368(6) . ? C22 C23 1.365(7) . ? C23 C24 1.377(6) . ? C25 C26 1.394(6) . ? C25 C30 1.406(6) . ? C26 C27 1.371(6) . ? C27 C28 1.364(7) . ? C28 C29 1.392(7) . ? C29 C30 1.383(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 P1 C13 101.42(17) . . ? C7 P1 C2 103.21(17) . . ? C13 P1 C2 99.39(17) . . ? C25 P2 C19 100.87(18) . . ? C25 P2 C5 100.67(18) . . ? C19 P2 C5 102.75(19) . . ? C1 O1 C4 110.1(3) . . ? C6 O2 C3 104.1(3) . . ? O1 C1 C2 105.9(3) . . ? C3 C2 C1 101.5(3) . . ? C3 C2 P1 115.3(3) . . ? C1 C2 P1 111.1(3) . . ? O2 C3 C2 110.3(3) . . ? O2 C3 C4 105.3(3) . . ? C2 C3 C4 104.4(3) . . ? O1 C4 C5 113.8(3) . . ? O1 C4 C3 106.7(3) . . ? C5 C4 C3 104.7(3) . . ? C4 C5 C6 102.9(3) . . ? C4 C5 P2 114.9(3) . . ? C6 C5 P2 110.8(3) . . ? O2 C6 C5 105.8(3) . . ? C12 C7 C8 118.6(4) . . ? C12 C7 P1 125.4(3) . . ? C8 C7 P1 116.0(3) . . ? C9 C8 C7 121.0(4) . . ? C8 C9 C10 119.5(4) . . ? C11 C10 C9 119.9(4) . . ? C10 C11 C12 120.9(4) . . ? C7 C12 C11 120.1(4) . . ? C14 C13 C18 118.7(4) . . ? C14 C13 P1 117.2(3) . . ? C18 C13 P1 124.1(3) . . ? C13 C14 C15 120.4(4) . . ? C16 C15 C14 120.9(4) . . ? C17 C16 C15 118.8(5) . . ? C16 C17 C18 120.7(4) . . ? C17 C18 C13 120.5(4) . . ? C20 C19 C24 118.4(4) . . ? C20 C19 P2 124.2(3) . . ? C24 C19 P2 117.2(3) . . ? C21 C20 C19 120.1(4) . . ? C22 C21 C20 120.4(4) . . ? C23 C22 C21 120.3(4) . . ? C22 C23 C24 120.0(5) . . ? C23 C24 C19 120.8(4) . . ? C26 C25 C30 118.1(4) . . ? C26 C25 P2 123.5(3) . . ? C30 C25 P2 118.5(3) . . ? C27 C26 C25 120.5(4) . . ? C28 C27 C26 121.1(5) . . ? C27 C28 C29 120.3(4) . . ? C30 C29 C28 119.1(4) . . ? C29 C30 C25 121.0(4) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.756 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.057