# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Dr. Dmitry B. Krivolapov' _publ_contact_author_address ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; _publ_contact_author_email ; calder@iopc.knc.ru ; _publ_contact_author_phone '+7 843 2727573' _publ_contact_author_fax '+7 843 2732253' loop_ _publ_author_name _publ_author_address A.Zagidullin ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; Y.Ganushevich ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; V.Miluykov ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; D.Krivolapov ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; O.Kataeva ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; O.Sinyashin ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; E.Hey-Hawkins ;Institut f\"ur Anorganische Chemie, Universit\"at Leipzig, Johannisallee 29, 04103 Leipzig, Germany ; #========================================================================== data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 865361' #TrackingRef 'mil7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C37 H33 N O2 P2), 3(C7 H8)' _chemical_formula_sum 'C47.50 H45 N O2 P2' _chemical_formula_weight 723.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3080(9) _cell_length_b 11.3298(9) _cell_length_c 15.5036(8) _cell_angle_alpha 76.884(3) _cell_angle_beta 88.093(2) _cell_angle_gamma 85.182(2) _cell_volume 1927.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9907 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 766 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9454 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 82675 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7370 _reflns_number_gt 5944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_cell_refinement 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_data_reduction 'SAINT NT v6.0 (Bruker AXS, 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0744P)^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 7370 _refine_ls_number_parameters 470 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.63422(3) 0.22816(3) 0.19572(3) 0.01820(12) Uani 1 1 d . . . O1 O 0.73747(9) 0.24509(10) 0.13507(8) 0.0250(3) Uani 1 1 d . . . P2 P 0.62158(3) 0.04479(4) 0.27863(3) 0.01875(12) Uani 1 1 d . . . O2 O 0.64732(10) 0.03262(10) 0.37364(7) 0.0257(3) Uani 1 1 d . . . C3 C 0.46672(13) 0.04391(13) 0.25249(10) 0.0178(3) Uani 1 1 d . . . C4 C 0.41026(13) 0.14494(13) 0.20263(10) 0.0173(3) Uani 1 1 d . . . C5 C 0.47628(13) 0.26046(13) 0.16740(10) 0.0176(3) Uani 1 1 d . . . C6 C 0.46887(13) 0.35270(14) 0.23284(10) 0.0186(3) Uani 1 1 d . . . H6 H 0.4569 0.4383 0.1975 0.022 Uiso 1 1 calc R . . N7 N 0.59500(11) 0.32512(11) 0.25888(9) 0.0193(3) Uani 1 1 d . . . C8 C 0.71080(15) -0.06313(14) 0.22772(11) 0.0252(4) Uani 1 1 d . . . H8 H 0.7954 -0.0448 0.2305 0.030 Uiso 1 1 calc R . . C9 C 0.68366(18) -0.05026(17) 0.13000(12) 0.0349(4) Uani 1 1 d . . . H9A H 0.7340 -0.1108 0.1066 0.052 Uiso 1 1 calc R . . H9B H 0.6996 0.0315 0.0968 0.052 Uiso 1 1 calc R . . H9C H 0.6000 -0.0631 0.1240 0.052 Uiso 1 1 calc R . . C10 C 0.70139(17) -0.19362(15) 0.28156(13) 0.0347(4) Uani 1 1 d . . . H10A H 0.6201 -0.2164 0.2789 0.052 Uiso 1 1 calc R . . H10B H 0.7216 -0.1986 0.3433 0.052 Uiso 1 1 calc R . . H10C H 0.7565 -0.2492 0.2568 0.052 Uiso 1 1 calc R . . C11 C 0.41305(13) -0.07272(14) 0.29048(11) 0.0188(3) Uani 1 1 d . . . C12 C 0.36087(14) -0.13565(14) 0.23566(12) 0.0232(4) Uani 1 1 d . . . H12 H 0.3519 -0.0999 0.1744 0.028 Uiso 1 1 calc R . . C13 C 0.32225(15) -0.24995(15) 0.27052(12) 0.0285(4) Uani 1 1 d . . . H13 H 0.2873 -0.2924 0.2329 0.034 Uiso 1 1 calc R . . C14 C 0.33423(16) -0.30244(15) 0.35959(12) 0.0304(4) Uani 1 1 d . . . H14 H 0.3087 -0.3813 0.3830 0.036 Uiso 1 1 calc R . . C15 C 0.38348(15) -0.24013(15) 0.41472(12) 0.0278(4) Uani 1 1 d . . . H15 H 0.3906 -0.2758 0.4762 0.033 Uiso 1 1 calc R . . C16 C 0.42255(14) -0.12557(15) 0.38051(11) 0.0234(4) Uani 1 1 d . . . H16 H 0.4560 -0.0830 0.4188 0.028 Uiso 1 1 calc R . . C17 C 0.28059(13) 0.15089(13) 0.18348(11) 0.0191(3) Uani 1 1 d . . . C18 C 0.24002(15) 0.16464(15) 0.09748(12) 0.0256(4) Uani 1 1 d . . . H18 H 0.2955 0.1684 0.0497 0.031 Uiso 1 1 calc R . . C19 C 0.11944(16) 0.17292(16) 0.08111(13) 0.0334(4) Uani 1 1 d . . . H19 H 0.0928 0.1820 0.0223 0.040 Uiso 1 1 calc R . . C20 C 0.03795(15) 0.16806(16) 0.14986(14) 0.0355(5) Uani 1 1 d . . . H20 H -0.0447 0.1761 0.1384 0.043 Uiso 1 1 calc R . . C21 C 0.07710(15) 0.15151(16) 0.23514(13) 0.0319(4) Uani 1 1 d . . . H21 H 0.0211 0.1461 0.2826 0.038 Uiso 1 1 calc R . . C22 C 0.19789(14) 0.14265(14) 0.25264(12) 0.0246(4) Uani 1 1 d . . . H22 H 0.2239 0.1310 0.3118 0.029 Uiso 1 1 calc R . . C23 C 0.44961(13) 0.31827(13) 0.07107(10) 0.0186(3) Uani 1 1 d . . . C24 C 0.36226(14) 0.41290(14) 0.04696(11) 0.0235(4) Uani 1 1 d . . . H24 H 0.3248 0.4501 0.0909 0.028 Uiso 1 1 calc R . . C25 C 0.32945(16) 0.45343(15) -0.04072(12) 0.0288(4) Uani 1 1 d . . . H25 H 0.2693 0.5179 -0.0565 0.035 Uiso 1 1 calc R . . C26 C 0.38344(16) 0.40089(16) -0.10515(12) 0.0293(4) Uani 1 1 d . . . H26 H 0.3589 0.4272 -0.1649 0.035 Uiso 1 1 calc R . . C27 C 0.47341(16) 0.30984(16) -0.08254(11) 0.0286(4) Uani 1 1 d . . . H27 H 0.5125 0.2751 -0.1272 0.034 Uiso 1 1 calc R . . C28 C 0.50675(15) 0.26896(15) 0.00484(11) 0.0247(4) Uani 1 1 d . . . H28 H 0.5692 0.2067 0.0198 0.030 Uiso 1 1 calc R . . C29 C 0.38002(14) 0.33255(14) 0.30800(11) 0.0193(3) Uani 1 1 d . . . C30 C 0.27275(14) 0.40324(14) 0.29973(11) 0.0232(4) Uani 1 1 d . . . H30 H 0.2583 0.4657 0.2480 0.028 Uiso 1 1 calc R . . C31 C 0.18682(15) 0.38396(15) 0.36573(12) 0.0282(4) Uani 1 1 d . . . H31 H 0.1137 0.4327 0.3591 0.034 Uiso 1 1 calc R . . C32 C 0.20753(16) 0.29328(16) 0.44173(12) 0.0289(4) Uani 1 1 d . . . H32 H 0.1481 0.2792 0.4869 0.035 Uiso 1 1 calc R . . C33 C 0.31461(15) 0.22336(15) 0.45172(11) 0.0266(4) Uani 1 1 d . . . H33 H 0.3287 0.1615 0.5039 0.032 Uiso 1 1 calc R . . C34 C 0.40144(14) 0.24327(14) 0.38584(11) 0.0217(4) Uani 1 1 d . . . H34 H 0.4755 0.1963 0.3935 0.026 Uiso 1 1 calc R . . C35 C 0.65720(14) 0.37234(14) 0.31886(11) 0.0205(3) Uani 1 1 d . . . C36 C 0.77062(15) 0.32091(16) 0.34381(12) 0.0277(4) Uani 1 1 d . . . H36 H 0.8041 0.2537 0.3217 0.033 Uiso 1 1 calc R . . C37 C 0.83441(16) 0.36810(17) 0.40099(12) 0.0335(4) Uani 1 1 d . . . H37 H 0.9120 0.3334 0.4176 0.040 Uiso 1 1 calc R . . C38 C 0.78670(17) 0.46460(17) 0.43407(12) 0.0347(4) Uani 1 1 d . . . H38 H 0.8313 0.4967 0.4730 0.042 Uiso 1 1 calc R . . C39 C 0.67343(17) 0.51490(16) 0.41043(12) 0.0312(4) Uani 1 1 d . . . H39 H 0.6400 0.5810 0.4339 0.037 Uiso 1 1 calc R . . C40 C 0.60809(15) 0.46944(14) 0.35259(11) 0.0252(4) Uani 1 1 d . . . H40 H 0.5305 0.5045 0.3362 0.030 Uiso 1 1 calc R . . C41A C -0.0377(3) 0.0707(2) 0.55844(18) 0.0643(8) Uani 0.50 1 d P A 1 C42A C -0.1167(2) 0.0445(3) 0.5004(2) 0.0657(8) Uani 0.50 1 d P . 1 H42A H -0.1973 0.0756 0.5009 0.079 Uiso 0.50 1 calc PR . 1 C43A C 0.0802(2) 0.0249(2) 0.5568(2) 0.0654(8) Uani 0.50 1 d P . 1 H43A H 0.1351 0.0426 0.5963 0.078 Uiso 0.50 1 calc PR . 1 C44A C -0.0676(4) 0.1395(4) 0.6132(3) 0.0507(11) Uani 0.50 1 d P A 1 H44A H -0.0846 0.2235 0.5801 0.076 Uiso 0.50 1 calc PR A 1 H44B H -0.0023 0.1360 0.6540 0.076 Uiso 0.50 1 calc PR A 1 H44C H -0.1385 0.1110 0.6470 0.076 Uiso 0.50 1 calc PR A 1 C41B C -0.0377(3) 0.0707(2) 0.55844(18) 0.0643(8) Uani 0.50 1 d P B 2 H41B H -0.0637 0.1195 0.5989 0.077 Uiso 0.50 1 calc PR B 2 C42B C -0.1167(2) 0.0445(3) 0.5004(2) 0.0657(8) Uani 0.50 1 d P . 2 H42B H -0.1973 0.0756 0.5009 0.079 Uiso 0.50 1 calc PR . 2 C43B C 0.0802(2) 0.0249(2) 0.5568(2) 0.0654(8) Uani 0.50 1 d P . 2 H43B H 0.1351 0.0426 0.5963 0.078 Uiso 0.50 1 calc PR . 2 C45A C -0.0786(2) 0.2720(3) -0.11020(19) 0.0381(6) Uiso 0.7354(19) 1 d PD C 1 C46A C -0.0023(3) 0.2955(3) -0.1851(2) 0.0429(7) Uiso 0.7354(19) 1 d PD C 1 H46A H 0.0169 0.2345 -0.2175 0.052 Uiso 0.7354(19) 1 calc PR C 1 C47A C 0.0447(3) 0.4075(3) -0.2113(2) 0.0567(8) Uiso 0.7354(19) 1 d PD C 1 H47A H 0.0994 0.4199 -0.2598 0.068 Uiso 0.7354(19) 1 calc PR C 1 C48A C 0.0162(3) 0.4974(3) -0.1713(2) 0.0492(8) Uiso 0.7354(19) 1 d PD C 1 H48A H 0.0473 0.5743 -0.1921 0.059 Uiso 0.7354(19) 1 calc PR C 1 C49A C -0.0610(3) 0.4772(3) -0.0974(2) 0.0459(7) Uiso 0.7354(19) 1 d PD C 1 H49A H -0.0824 0.5403 -0.0673 0.055 Uiso 0.7354(19) 1 calc PR C 1 C50A C -0.1049(3) 0.3660(3) -0.0694(2) 0.0362(7) Uiso 0.7354(19) 1 d PD C 1 H50A H -0.1562 0.3534 -0.0189 0.043 Uiso 0.7354(19) 1 calc PR C 1 C51A C -0.1252(3) 0.1502(3) -0.0789(2) 0.0510(8) Uiso 0.7354(19) 1 d PD C 1 H51A H -0.0737 0.1005 -0.0326 0.076 Uiso 0.7354(19) 1 calc PR C 1 H51B H -0.1268 0.1103 -0.1286 0.076 Uiso 0.7354(19) 1 calc PR C 1 H51C H -0.2058 0.1598 -0.0548 0.076 Uiso 0.7354(19) 1 calc PR C 1 C45B C -0.0410(6) 0.3970(6) -0.1427(5) 0.0381(6) Uiso 0.2646(19) 1 d PD C 2 C46B C -0.1102(8) 0.3233(8) -0.0749(6) 0.0429(7) Uiso 0.2646(19) 1 d PD C 2 H46B H -0.1437 0.3592 -0.0290 0.052 Uiso 0.2646(19) 1 calc PR C 2 C47B C -0.1307(9) 0.2091(9) -0.0717(6) 0.0567(8) Uiso 0.2646(19) 1 d PD C 2 H47B H -0.1792 0.1641 -0.0271 0.068 Uiso 0.2646(19) 1 calc PR C 2 C48B C -0.0751(7) 0.1591(8) -0.1396(6) 0.0492(8) Uiso 0.2646(19) 1 d PD C 2 H48B H -0.0799 0.0753 -0.1381 0.059 Uiso 0.2646(19) 1 calc PR C 2 C49B C -0.0157(7) 0.2277(7) -0.2062(6) 0.0459(7) Uiso 0.2646(19) 1 d PD C 2 H49B H 0.0140 0.1904 -0.2525 0.055 Uiso 0.2646(19) 1 calc PR C 2 C50B C 0.0073(7) 0.3541(8) -0.2138(5) 0.0362(7) Uiso 0.2646(19) 1 d PD C 2 H50B H 0.0499 0.4011 -0.2615 0.043 Uiso 0.2646(19) 1 calc PR C 2 C51B C -0.0126(9) 0.5212(8) -0.1374(7) 0.0510(8) Uiso 0.2646(19) 1 d PD C 2 H51D H 0.0707 0.5320 -0.1543 0.076 Uiso 0.2646(19) 1 calc PR C 2 H51E H -0.0263 0.5314 -0.0767 0.076 Uiso 0.2646(19) 1 calc PR C 2 H51F H -0.0636 0.5819 -0.1779 0.076 Uiso 0.2646(19) 1 calc PR C 2 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 0.0163(2) 0.0178(2) 0.0196(3) -0.00216(17) -0.00120(16) -0.00137(15) O1 0.0200(6) 0.0257(6) 0.0276(7) -0.0029(5) 0.0030(5) -0.0023(5) P2 0.0164(2) 0.0179(2) 0.0206(3) -0.00161(17) -0.00251(16) -0.00019(15) O2 0.0245(6) 0.0278(6) 0.0233(7) -0.0019(5) -0.0069(5) -0.0013(5) C3 0.0172(7) 0.0195(8) 0.0170(9) -0.0051(6) -0.0009(6) -0.0013(6) C4 0.0192(8) 0.0196(8) 0.0138(9) -0.0049(6) 0.0000(6) -0.0025(6) C5 0.0164(7) 0.0178(7) 0.0180(9) -0.0029(6) -0.0004(6) -0.0011(6) C6 0.0190(8) 0.0173(7) 0.0189(9) -0.0022(6) -0.0031(6) -0.0016(6) N7 0.0172(6) 0.0198(7) 0.0211(8) -0.0044(6) -0.0020(5) -0.0021(5) C8 0.0219(8) 0.0235(8) 0.0284(10) -0.0036(7) 0.0021(7) 0.0021(7) C9 0.0437(11) 0.0285(9) 0.0327(12) -0.0097(8) 0.0050(9) 0.0015(8) C10 0.0365(10) 0.0219(9) 0.0415(12) -0.0031(8) 0.0054(9) 0.0077(8) C11 0.0149(7) 0.0179(8) 0.0229(9) -0.0042(6) -0.0002(6) 0.0011(6) C12 0.0230(8) 0.0230(8) 0.0228(10) -0.0035(7) -0.0012(7) -0.0012(7) C13 0.0301(9) 0.0237(9) 0.0339(11) -0.0092(8) 0.0008(8) -0.0070(7) C14 0.0345(10) 0.0198(8) 0.0352(12) -0.0019(8) 0.0068(8) -0.0074(7) C15 0.0308(9) 0.0253(9) 0.0238(10) 0.0019(7) 0.0012(7) -0.0033(7) C16 0.0226(8) 0.0245(8) 0.0228(10) -0.0040(7) -0.0022(7) -0.0021(7) C17 0.0183(8) 0.0136(7) 0.0245(10) -0.0027(6) -0.0026(7) -0.0002(6) C18 0.0241(8) 0.0261(9) 0.0253(10) -0.0017(7) -0.0040(7) -0.0042(7) C19 0.0296(10) 0.0334(10) 0.0349(12) -0.0001(8) -0.0138(8) -0.0058(8) C20 0.0183(8) 0.0317(10) 0.0548(14) -0.0053(9) -0.0104(9) -0.0002(7) C21 0.0203(8) 0.0294(9) 0.0454(13) -0.0083(8) 0.0065(8) -0.0022(7) C22 0.0235(8) 0.0210(8) 0.0288(10) -0.0049(7) 0.0001(7) -0.0015(7) C23 0.0196(8) 0.0171(7) 0.0184(9) -0.0015(6) -0.0006(6) -0.0051(6) C24 0.0270(9) 0.0223(8) 0.0199(10) -0.0027(7) -0.0014(7) -0.0007(7) C25 0.0337(10) 0.0224(9) 0.0267(11) 0.0018(7) -0.0079(8) 0.0009(7) C26 0.0414(10) 0.0283(9) 0.0163(10) 0.0024(7) -0.0049(8) -0.0104(8) C27 0.0358(10) 0.0320(9) 0.0193(10) -0.0072(7) 0.0041(8) -0.0068(8) C28 0.0274(9) 0.0235(8) 0.0223(10) -0.0035(7) 0.0005(7) -0.0009(7) C29 0.0220(8) 0.0187(8) 0.0193(9) -0.0076(6) -0.0012(6) -0.0035(6) C30 0.0257(8) 0.0198(8) 0.0238(10) -0.0046(7) -0.0016(7) -0.0013(7) C31 0.0242(9) 0.0283(9) 0.0333(11) -0.0112(8) 0.0021(8) 0.0013(7) C32 0.0297(9) 0.0339(10) 0.0248(10) -0.0101(8) 0.0087(7) -0.0066(7) C33 0.0331(9) 0.0281(9) 0.0183(10) -0.0041(7) 0.0001(7) -0.0036(7) C34 0.0229(8) 0.0230(8) 0.0194(9) -0.0048(7) -0.0023(7) -0.0019(6) C35 0.0238(8) 0.0198(8) 0.0170(9) 0.0000(6) -0.0016(7) -0.0076(6) C36 0.0249(9) 0.0299(9) 0.0285(11) -0.0055(8) -0.0031(7) -0.0048(7) C37 0.0280(9) 0.0402(11) 0.0320(11) -0.0038(8) -0.0075(8) -0.0111(8) C38 0.0439(11) 0.0385(10) 0.0241(11) -0.0047(8) -0.0063(8) -0.0213(9) C39 0.0491(11) 0.0227(9) 0.0227(10) -0.0040(7) 0.0010(8) -0.0124(8) C40 0.0308(9) 0.0213(8) 0.0226(10) -0.0017(7) -0.0024(7) -0.0044(7) C41A 0.0733(18) 0.0521(15) 0.0566(17) 0.0201(13) -0.0210(14) -0.0240(13) C42A 0.0481(14) 0.0604(16) 0.073(2) 0.0278(14) -0.0287(13) -0.0229(12) C43A 0.0540(15) 0.0594(16) 0.0691(19) 0.0274(14) -0.0372(14) -0.0269(13) C44A 0.051(3) 0.051(3) 0.048(3) -0.012(2) 0.000(2) 0.007(2) C41B 0.0733(18) 0.0521(15) 0.0566(17) 0.0201(13) -0.0210(14) -0.0240(13) C42B 0.0481(14) 0.0604(16) 0.073(2) 0.0278(14) -0.0287(13) -0.0229(12) C43B 0.0540(15) 0.0594(16) 0.0691(19) 0.0274(14) -0.0372(14) -0.0269(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4720(11) . ? P1 N7 1.6552(13) . ? P1 C5 1.8401(15) . ? P1 P2 2.1943(6) . ? P2 O2 1.4842(12) . ? P2 C3 1.8119(15) . ? P2 C8 1.8203(16) . ? C3 C4 1.351(2) . ? C3 C11 1.490(2) . ? C4 C17 1.499(2) . ? C4 C5 1.543(2) . ? C5 C23 1.518(2) . ? C5 C6 1.609(2) . ? C6 N7 1.4837(19) . ? C6 C29 1.503(2) . ? C6 H6 1.0000 . ? N7 C35 1.406(2) . ? C8 C9 1.528(3) . ? C8 C10 1.534(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.392(2) . ? C11 C12 1.399(2) . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.391(2) . ? C17 C18 1.395(2) . ? C18 C19 1.387(2) . ? C18 H18 0.9500 . ? C19 C20 1.380(3) . ? C19 H19 0.9500 . ? C20 C21 1.375(3) . ? C20 H20 0.9500 . ? C21 C22 1.392(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.389(2) . ? C23 C28 1.393(2) . ? C24 C25 1.385(2) . ? C24 H24 0.9500 . ? C25 C26 1.376(3) . ? C25 H25 0.9500 . ? C26 C27 1.380(3) . ? C26 H26 0.9500 . ? C27 C28 1.383(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.389(2) . ? C29 C34 1.401(2) . ? C30 C31 1.381(2) . ? C30 H30 0.9500 . ? C31 C32 1.388(3) . ? C31 H31 0.9500 . ? C32 C33 1.383(2) . ? C32 H32 0.9500 . ? C33 C34 1.387(2) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C40 1.390(2) . ? C35 C36 1.393(2) . ? C36 C37 1.384(2) . ? C36 H36 0.9500 . ? C37 C38 1.373(3) . ? C37 H37 0.9500 . ? C38 C39 1.383(3) . ? C38 H38 0.9500 . ? C39 C40 1.390(2) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41A C44A 1.296(5) . ? C41A C42A 1.384(4) . ? C41A C43A 1.390(4) . ? C42A C43A 1.347(4) 2_556 ? C42A H42A 0.9500 . ? C43A C42A 1.347(4) 2_556 ? C43A H43A 0.9500 . ? C44A H44A 0.9800 . ? C44A H44B 0.9800 . ? C44A H44C 0.9800 . ? C45A C50A 1.365(4) . ? C45A C46A 1.413(4) . ? C45A C51A 1.489(4) . ? C46A C47A 1.386(5) . ? C46A H46A 0.9500 . ? C47A C48A 1.321(5) . ? C47A H47A 0.9500 . ? C48A C49A 1.406(4) . ? C48A H48A 0.9500 . ? C49A C50A 1.365(4) . ? C49A H49A 0.9500 . ? C50A H50A 0.9500 . ? C51A H51A 0.9800 . ? C51A H51B 0.9800 . ? C51A H51C 0.9800 . ? C45B C50B 1.382(9) . ? C45B C46B 1.440(10) . ? C45B C51B 1.490(10) . ? C46B C47B 1.323(12) . ? C46B H46B 0.9500 . ? C47B C48B 1.411(11) . ? C47B H47B 0.9500 . ? C48B C49B 1.342(10) . ? C48B H48B 0.9500 . ? C49B C50B 1.455(10) . ? C49B H49B 0.9500 . ? C50B H50B 0.9500 . ? C51B H51D 0.9800 . ? C51B H51E 0.9800 . ? C51B H51F 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 O1 P1 N7 121.34(7) . . ? O1 P1 C5 127.62(7) . . ? N7 P1 C5 80.44(7) . . ? O1 P1 P2 116.20(5) . . ? N7 P1 P2 106.98(5) . . ? C5 P1 P2 97.44(5) . . ? O2 P2 C3 115.69(7) . . ? O2 P2 C8 113.66(7) . . ? C3 P2 C8 109.65(7) . . ? O2 P2 P1 114.68(5) . . ? C3 P2 P1 92.46(5) . . ? C8 P2 P1 108.73(6) . . ? C4 C3 C11 125.91(14) . . ? C4 C3 P2 119.43(12) . . ? C11 C3 P2 114.66(11) . . ? C3 C4 C17 121.36(14) . . ? C3 C4 C5 120.77(13) . . ? C17 C4 C5 117.80(12) . . ? C23 C5 C4 112.59(12) . . ? C23 C5 C6 115.36(12) . . ? C4 C5 C6 113.90(12) . . ? C23 C5 P1 116.14(10) . . ? C4 C5 P1 109.38(10) . . ? C6 C5 P1 87.06(9) . . ? N7 C6 C29 115.33(13) . . ? N7 C6 C5 93.89(11) . . ? C29 C6 C5 117.80(12) . . ? N7 C6 H6 109.6 . . ? C29 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C35 N7 C6 128.32(13) . . ? C35 N7 P1 133.12(11) . . ? C6 N7 P1 98.56(9) . . ? C9 C8 C10 112.00(15) . . ? C9 C8 P2 113.37(11) . . ? C10 C8 P2 110.79(12) . . ? C9 C8 H8 106.7 . . ? C10 C8 H8 106.7 . . ? P2 C8 H8 106.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.86(15) . . ? C16 C11 C3 120.16(14) . . ? C12 C11 C3 120.78(15) . . ? C13 C12 C11 120.21(16) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.40(16) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.91(16) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.19(17) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.41(16) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C17 C18 118.72(14) . . ? C22 C17 C4 119.67(14) . . ? C18 C17 C4 121.61(14) . . ? C19 C18 C17 120.56(16) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.28(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.59(16) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.76(17) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C17 120.04(16) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C24 C23 C28 118.58(15) . . ? C24 C23 C5 121.80(14) . . ? C28 C23 C5 119.39(14) . . ? C25 C24 C23 120.45(16) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 120.41(16) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 119.70(16) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 120.21(16) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.56(16) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? C30 C29 C34 118.89(15) . . ? C30 C29 C6 119.18(14) . . ? C34 C29 C6 121.93(14) . . ? C31 C30 C29 120.88(15) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 119.88(16) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C33 C32 C31 120.01(16) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.20(16) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C29 120.10(15) . . ? C33 C34 H34 120.0 . . ? C29 C34 H34 120.0 . . ? C40 C35 C36 119.83(15) . . ? C40 C35 N7 121.28(15) . . ? C36 C35 N7 118.88(14) . . ? C37 C36 C35 119.73(17) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C38 C37 C36 120.71(17) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C39 119.75(17) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C38 C39 C40 120.48(17) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C35 C40 C39 119.48(16) . . ? C35 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C44A C41A C42A 122.9(4) . . ? C44A C41A C43A 117.8(3) . . ? C42A C41A C43A 119.2(3) . . ? C43A C42A C41A 120.5(3) 2_556 . ? C43A C42A H42A 119.8 2_556 . ? C41A C42A H42A 119.8 . . ? C42A C43A C41A 120.3(2) 2_556 . ? C42A C43A H43A 119.9 2_556 . ? C41A C43A H43A 119.9 . . ? C50A C45A C46A 116.1(3) . . ? C50A C45A C51A 123.3(3) . . ? C46A C45A C51A 120.6(3) . . ? C47A C46A C45A 120.1(3) . . ? C47A C46A H46A 119.9 . . ? C45A C46A H46A 119.9 . . ? C48A C47A C46A 122.4(3) . . ? C48A C47A H47A 118.8 . . ? C46A C47A H47A 118.8 . . ? C47A C48A C49A 118.7(3) . . ? C47A C48A H48A 120.6 . . ? C49A C48A H48A 120.6 . . ? C50A C49A C48A 119.3(3) . . ? C50A C49A H49A 120.3 . . ? C48A C49A H49A 120.3 . . ? C45A C50A C49A 123.3(3) . . ? C45A C50A H50A 118.3 . . ? C49A C50A H50A 118.3 . . ? C50B C45B C46B 121.8(7) . . ? C50B C45B C51B 116.5(7) . . ? C46B C45B C51B 121.7(8) . . ? C47B C46B C45B 124.8(9) . . ? C47B C46B H46B 117.6 . . ? C45B C46B H46B 117.6 . . ? C46B C47B C48B 115.1(9) . . ? C46B C47B H47B 122.5 . . ? C48B C47B H47B 122.5 . . ? C49B C48B C47B 121.2(8) . . ? C49B C48B H48B 119.4 . . ? C47B C48B H48B 119.4 . . ? C48B C49B C50B 125.7(8) . . ? C48B C49B H49B 117.2 . . ? C50B C49B H49B 117.2 . . ? C45B C50B C49B 111.2(8) . . ? C45B C50B H50B 124.4 . . ? C49B C50B H50B 124.4 . . ? C45B C51B H51D 109.5 . . ? C45B C51B H51E 109.5 . . ? H51D C51B H51E 109.5 . . ? C45B C51B H51F 109.5 . . ? H51D C51B H51F 109.5 . . ? H51E C51B H51F 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 O1 P1 P2 O2 107.51(8) . . . . ? N7 P1 P2 O2 -31.63(7) . . . . ? C5 P1 P2 O2 -113.86(7) . . . . ? O1 P1 P2 C3 -132.67(7) . . . . ? N7 P1 P2 C3 88.18(7) . . . . ? C5 P1 P2 C3 5.95(7) . . . . ? O1 P1 P2 C8 -20.96(8) . . . . ? N7 P1 P2 C8 -160.11(8) . . . . ? C5 P1 P2 C8 117.66(8) . . . . ? O2 P2 C3 C4 114.48(13) . . . . ? C8 P2 C3 C4 -115.39(13) . . . . ? P1 P2 C3 C4 -4.50(13) . . . . ? O2 P2 C3 C11 -65.06(13) . . . . ? C8 P2 C3 C11 65.07(13) . . . . ? P1 P2 C3 C11 175.96(11) . . . . ? C11 C3 C4 C17 2.9(2) . . . . ? P2 C3 C4 C17 -176.57(11) . . . . ? C11 C3 C4 C5 179.83(13) . . . . ? P2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 C23 135.84(15) . . . . ? C17 C4 C5 C23 -47.13(18) . . . . ? C3 C4 C5 C6 -90.39(17) . . . . ? C17 C4 C5 C6 86.63(16) . . . . ? C3 C4 C5 P1 5.14(18) . . . . ? C17 C4 C5 P1 -177.84(11) . . . . ? O1 P1 C5 C23 -3.96(15) . . . . ? N7 P1 C5 C23 118.46(12) . . . . ? P2 P1 C5 C23 -135.48(10) . . . . ? O1 P1 C5 C4 124.81(11) . . . . ? N7 P1 C5 C4 -112.77(11) . . . . ? P2 P1 C5 C4 -6.71(10) . . . . ? O1 P1 C5 C6 -120.86(9) . . . . ? N7 P1 C5 C6 1.55(8) . . . . ? P2 P1 C5 C6 107.62(8) . . . . ? C23 C5 C6 N7 -119.35(13) . . . . ? C4 C5 C6 N7 108.20(13) . . . . ? P1 C5 C6 N7 -1.71(9) . . . . ? C23 C5 C6 C29 119.28(14) . . . . ? C4 C5 C6 C29 -13.16(19) . . . . ? P1 C5 C6 C29 -123.08(12) . . . . ? C29 C6 N7 C35 -55.6(2) . . . . ? C5 C6 N7 C35 -178.95(14) . . . . ? C29 C6 N7 P1 125.24(11) . . . . ? C5 C6 N7 P1 1.92(10) . . . . ? O1 P1 N7 C35 -52.28(17) . . . . ? C5 P1 N7 C35 179.24(16) . . . . ? P2 P1 N7 C35 84.31(15) . . . . ? O1 P1 N7 C6 126.78(9) . . . . ? C5 P1 N7 C6 -1.70(9) . . . . ? P2 P1 N7 C6 -96.63(8) . . . . ? O2 P2 C8 C9 179.88(12) . . . . ? C3 P2 C8 C9 48.67(15) . . . . ? P1 P2 C8 C9 -51.07(14) . . . . ? O2 P2 C8 C10 52.97(15) . . . . ? C3 P2 C8 C10 -78.24(14) . . . . ? P1 P2 C8 C10 -177.98(11) . . . . ? C4 C3 C11 C16 -127.49(18) . . . . ? P2 C3 C11 C16 52.02(17) . . . . ? C4 C3 C11 C12 57.6(2) . . . . ? P2 C3 C11 C12 -122.85(14) . . . . ? C16 C11 C12 C13 -1.6(2) . . . . ? C3 C11 C12 C13 173.33(14) . . . . ? C11 C12 C13 C14 0.4(2) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? C12 C11 C16 C15 1.6(2) . . . . ? C3 C11 C16 C15 -173.40(14) . . . . ? C3 C4 C17 C22 64.0(2) . . . . ? C5 C4 C17 C22 -113.02(16) . . . . ? C3 C4 C17 C18 -116.06(18) . . . . ? C5 C4 C17 C18 66.94(19) . . . . ? C22 C17 C18 C19 1.6(2) . . . . ? C4 C17 C18 C19 -178.40(15) . . . . ? C17 C18 C19 C20 0.2(3) . . . . ? C18 C19 C20 C21 -1.8(3) . . . . ? C19 C20 C21 C22 1.6(3) . . . . ? C20 C21 C22 C17 0.2(3) . . . . ? C18 C17 C22 C21 -1.8(2) . . . . ? C4 C17 C22 C21 178.20(14) . . . . ? C4 C5 C23 C24 95.45(17) . . . . ? C6 C5 C23 C24 -37.60(19) . . . . ? P1 C5 C23 C24 -137.36(13) . . . . ? C4 C5 C23 C28 -79.00(17) . . . . ? C6 C5 C23 C28 147.95(14) . . . . ? P1 C5 C23 C28 48.20(18) . . . . ? C28 C23 C24 C25 2.8(2) . . . . ? C5 C23 C24 C25 -171.71(14) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C27 -2.0(3) . . . . ? C25 C26 C27 C28 2.0(3) . . . . ? C26 C27 C28 C23 0.5(3) . . . . ? C24 C23 C28 C27 -2.8(2) . . . . ? C5 C23 C28 C27 171.79(14) . . . . ? N7 C6 C29 C30 150.41(14) . . . . ? C5 C6 C29 C30 -100.06(17) . . . . ? N7 C6 C29 C34 -30.5(2) . . . . ? C5 C6 C29 C34 79.02(19) . . . . ? C34 C29 C30 C31 -1.9(2) . . . . ? C6 C29 C30 C31 177.21(14) . . . . ? C29 C30 C31 C32 0.3(2) . . . . ? C30 C31 C32 C33 0.8(3) . . . . ? C31 C32 C33 C34 -0.2(3) . . . . ? C32 C33 C34 C29 -1.4(2) . . . . ? C30 C29 C34 C33 2.4(2) . . . . ? C6 C29 C34 C33 -176.64(14) . . . . ? C6 N7 C35 C40 -10.1(2) . . . . ? P1 N7 C35 C40 168.72(12) . . . . ? C6 N7 C35 C36 170.55(14) . . . . ? P1 N7 C35 C36 -10.6(2) . . . . ? C40 C35 C36 C37 -1.0(2) . . . . ? N7 C35 C36 C37 178.37(15) . . . . ? C35 C36 C37 C38 0.5(3) . . . . ? C36 C37 C38 C39 0.4(3) . . . . ? C37 C38 C39 C40 -0.8(3) . . . . ? C36 C35 C40 C39 0.6(2) . . . . ? N7 C35 C40 C39 -178.79(15) . . . . ? C38 C39 C40 C35 0.3(3) . . . . ? C44A C41A C42A C43A 178.2(3) . . . 2_556 ? C43A C41A C42A C43A 0.2(4) . . . 2_556 ? C44A C41A C43A C42A -178.3(3) . . . 2_556 ? C42A C41A C43A C42A -0.2(4) . . . 2_556 ? C50A C45A C46A C47A 2.2(4) . . . . ? C51A C45A C46A C47A -177.2(3) . . . . ? C45A C46A C47A C48A -3.5(5) . . . . ? C46A C47A C48A C49A 2.5(5) . . . . ? C47A C48A C49A C50A -0.4(5) . . . . ? C46A C45A C50A C49A -0.2(4) . . . . ? C51A C45A C50A C49A 179.1(3) . . . . ? C48A C49A C50A C45A -0.7(5) . . . . ? C50B C45B C46B C47B 2.6(14) . . . . ? C51B C45B C46B C47B -174.4(9) . . . . ? C45B C46B C47B C48B 2.3(14) . . . . ? C46B C47B C48B C49B -6.0(13) . . . . ? C47B C48B C49B C50B 5.2(14) . . . . ? C46B C45B C50B C49B -3.4(11) . . . . ? C51B C45B C50B C49B 173.6(7) . . . . ? C48B C49B C50B C45B -0.3(12) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.502 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.044 #========================================================================== data_shelxl _database_code_depnum_ccdc_archive 'CCDC 865362' #TrackingRef 'mil10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H37 N O2 P2' _chemical_formula_sum 'C35 H37 N O2 P2' _chemical_formula_weight 565.60 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.231(3) _cell_length_b 14.736(4) _cell_length_c 20.826(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.290(4) _cell_angle_gamma 90.00 _cell_volume 3067.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6681 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9466 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_device 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27222 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7279 _reflns_number_gt 4762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_cell_refinement 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_data_reduction 'SAINT NT v6.0 (Bruker AXS, 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0607P)^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 7279 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.74676(4) 0.62318(3) 0.10348(2) 0.03643(12) Uani 1 1 d . . . P2 P 0.73633(4) 0.75312(3) 0.15644(2) 0.03708(13) Uani 1 1 d . . . N3 N 0.80995(13) 0.83375(9) 0.12199(7) 0.0397(3) Uani 1 1 d . . . C2 C 1.10066(17) 0.63248(10) 0.24394(8) 0.0390(4) Uani 1 1 d . . . C3 C 0.96743(16) 0.65420(10) 0.20078(7) 0.0336(4) Uani 1 1 d . . . C4 C 0.94383(16) 0.82860(11) 0.16685(8) 0.0359(4) Uani 1 1 d . . . H4A H 0.9596 0.8836 0.1938 0.043 Uiso 1 1 calc R . . O1 O 0.74429(12) 0.63296(8) 0.03244(5) 0.0492(3) Uani 1 1 d . . . C6 C 1.05821(17) 0.81427(11) 0.13316(8) 0.0396(4) Uani 1 1 d . . . O2 O 0.60945(12) 0.76913(9) 0.17670(6) 0.0528(3) Uani 1 1 d . . . C8 C 0.96523(16) 0.50367(11) 0.14627(8) 0.0381(4) Uani 1 1 d . . . C9 C 0.90634(16) 0.59400(10) 0.15578(8) 0.0353(4) Uani 1 1 d . . . C10 C 0.91455(17) 0.76915(11) 0.28174(8) 0.0390(4) Uani 1 1 d . . . C11 C 0.62568(18) 0.54265(12) 0.12175(9) 0.0472(4) Uani 1 1 d . . . H11A H 0.6466 0.4835 0.1049 0.057 Uiso 1 1 calc R . . C12 C 0.9701(2) 0.43450(12) 0.19115(10) 0.0524(5) Uani 1 1 d . . . H12A H 0.9331 0.4433 0.2278 0.063 Uiso 1 1 calc R . . C13 C 0.90381(15) 0.74624(10) 0.20985(8) 0.0332(4) Uani 1 1 d . . . C14 C 1.04446(19) 0.76324(12) 0.07595(9) 0.0484(5) Uani 1 1 d . . . H14A H 0.9624 0.7370 0.0575 0.058 Uiso 1 1 calc R . . C15 C 1.18190(18) 0.85235(12) 0.15989(10) 0.0513(5) Uani 1 1 d . . . H15A H 1.1927 0.8868 0.1981 0.062 Uiso 1 1 calc R . . C16 C 1.2346(3) 0.58649(15) 0.34763(12) 0.0813(8) Uani 1 1 d . . . H16A H 1.2410 0.5676 0.3908 0.098 Uiso 1 1 calc R . . C17 C 1.21582(19) 0.63883(13) 0.21991(11) 0.0565(5) Uani 1 1 d . . . H17A H 1.2106 0.6552 0.1763 0.068 Uiso 1 1 calc R . . C18 C 1.1108(2) 0.60554(12) 0.30848(9) 0.0563(5) Uani 1 1 d . . . H18A H 1.0342 0.6002 0.3255 0.068 Uiso 1 1 calc R . . C19 C 1.0459(2) 0.82116(13) 0.38544(10) 0.0621(6) Uani 1 1 d . . . H19A H 1.1242 0.8465 0.4097 0.075 Uiso 1 1 calc R . . C20 C 0.75352(18) 0.91098(12) 0.07961(9) 0.0461(4) Uani 1 1 d . . . C21 C 1.0829(2) 0.33839(13) 0.12915(11) 0.0643(6) Uani 1 1 d . . . H21A H 1.1230 0.2832 0.1235 0.077 Uiso 1 1 calc R . . C22 C 0.7123(3) 0.98485(15) 0.12204(13) 0.0987(9) Uani 1 1 d . . . H22A H 0.6455 0.9617 0.1438 0.148 Uiso 1 1 calc R . . H22B H 0.6766 1.0355 0.0949 0.148 Uiso 1 1 calc R . . H22C H 0.7889 1.0042 0.1543 0.148 Uiso 1 1 calc R . . C23 C 1.2890(2) 0.83949(15) 0.13021(12) 0.0668(6) Uani 1 1 d . . . H23A H 1.3716 0.8650 0.1487 0.080 Uiso 1 1 calc R . . C24 C 1.0304(2) 0.80870(12) 0.31835(9) 0.0498(5) Uani 1 1 d . . . H24A H 1.0979 0.8269 0.2975 0.060 Uiso 1 1 calc R . . C25 C 1.3474(3) 0.59528(17) 0.32326(17) 0.0929(10) Uani 1 1 d . . . H25A H 1.4308 0.5836 0.3500 0.111 Uiso 1 1 calc R . . C26 C 1.3383(2) 0.62118(16) 0.25981(16) 0.0810(8) Uani 1 1 d . . . H26A H 1.4155 0.6270 0.2433 0.097 Uiso 1 1 calc R . . C27 C 1.1526(2) 0.75132(14) 0.04630(11) 0.0632(6) Uani 1 1 d . . . H27A H 1.1426 0.7175 0.0078 0.076 Uiso 1 1 calc R . . C28 C 0.48544(19) 0.56837(15) 0.08513(12) 0.0716(6) Uani 1 1 d . . . H28A H 0.4232 0.5227 0.0923 0.107 Uiso 1 1 calc R . . H28B H 0.4837 0.5729 0.0390 0.107 Uiso 1 1 calc R . . H28C H 0.4610 0.6257 0.1010 0.107 Uiso 1 1 calc R . . C29 C 1.2745(2) 0.78934(16) 0.07363(13) 0.0730(7) Uani 1 1 d . . . H29A H 1.3469 0.7811 0.0538 0.088 Uiso 1 1 calc R . . C30 C 0.9457(3) 0.79604(15) 0.41583(10) 0.0690(7) Uani 1 1 d . . . H30A H 0.9558 0.8048 0.4608 0.083 Uiso 1 1 calc R . . C31 C 1.0188(2) 0.48830(13) 0.09156(9) 0.0571(5) Uani 1 1 d . . . H31A H 1.0148 0.5335 0.0600 0.068 Uiso 1 1 calc R . . C32 C 1.0783(2) 0.40568(14) 0.08359(11) 0.0685(6) Uani 1 1 d . . . H32A H 1.1152 0.3960 0.0470 0.082 Uiso 1 1 calc R . . C33 C 0.6357(2) 0.53183(15) 0.19568(10) 0.0634(6) Uani 1 1 d . . . H33A H 0.5700 0.4888 0.2032 0.095 Uiso 1 1 calc R . . H33B H 0.6199 0.5894 0.2143 0.095 Uiso 1 1 calc R . . H33C H 0.7234 0.5105 0.2160 0.095 Uiso 1 1 calc R . . C34 C 1.0290(2) 0.35206(13) 0.18274(11) 0.0614(6) Uani 1 1 d . . . H34A H 1.0317 0.3061 0.2136 0.074 Uiso 1 1 calc R . . C35 C 0.6345(2) 0.87496(16) 0.03019(11) 0.0778(7) Uani 1 1 d . . . H35A H 0.5682 0.8532 0.0528 0.117 Uiso 1 1 calc R . . H35B H 0.6627 0.8261 0.0058 0.117 Uiso 1 1 calc R . . H35C H 0.5970 0.9227 0.0006 0.117 Uiso 1 1 calc R . . C37 C 0.8559(2) 0.94882(15) 0.04322(11) 0.0712(6) Uani 1 1 d . . . H37A H 0.9335 0.9689 0.0744 0.107 Uiso 1 1 calc R . . H37B H 0.8175 0.9990 0.0163 0.107 Uiso 1 1 calc R . . H37C H 0.8811 0.9023 0.0159 0.107 Uiso 1 1 calc R . . C38 C 0.8149(2) 0.74448(13) 0.31343(9) 0.0527(5) Uani 1 1 d . . . H38A H 0.7365 0.7185 0.2897 0.063 Uiso 1 1 calc R . . C40 C 0.8306(3) 0.75811(15) 0.38063(10) 0.0693(6) Uani 1 1 d . . . H40A H 0.7627 0.7414 0.4017 0.083 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 0.0380(2) 0.0390(2) 0.0312(2) -0.00169(18) 0.00482(18) 0.00125(18) P2 0.0326(2) 0.0438(2) 0.0338(3) -0.00190(19) 0.00489(18) 0.00332(18) N3 0.0356(8) 0.0400(7) 0.0408(8) 0.0017(6) 0.0019(6) 0.0031(6) C2 0.0406(9) 0.0329(8) 0.0400(10) -0.0058(7) 0.0010(8) 0.0059(7) C3 0.0357(8) 0.0376(8) 0.0288(9) -0.0009(7) 0.0096(7) 0.0025(7) C4 0.0348(9) 0.0349(8) 0.0362(9) -0.0033(7) 0.0031(7) 0.0020(7) O1 0.0558(8) 0.0602(8) 0.0296(7) -0.0013(6) 0.0049(6) 0.0033(6) C6 0.0388(9) 0.0367(8) 0.0439(10) 0.0036(8) 0.0099(8) 0.0005(7) O2 0.0379(7) 0.0660(8) 0.0562(8) -0.0042(6) 0.0139(6) 0.0078(6) C8 0.0385(9) 0.0391(9) 0.0351(9) -0.0050(7) 0.0047(7) 0.0032(7) C9 0.0388(9) 0.0383(8) 0.0299(9) 0.0004(7) 0.0096(7) 0.0034(7) C10 0.0456(10) 0.0378(9) 0.0313(9) -0.0039(7) 0.0030(8) 0.0092(7) C11 0.0472(10) 0.0407(9) 0.0509(11) 0.0017(8) 0.0045(9) -0.0037(8) C12 0.0604(12) 0.0469(10) 0.0536(12) 0.0060(9) 0.0205(10) 0.0082(9) C13 0.0316(8) 0.0374(8) 0.0305(9) -0.0029(7) 0.0062(7) 0.0024(7) C14 0.0457(10) 0.0520(11) 0.0501(12) -0.0017(9) 0.0162(9) -0.0034(8) C15 0.0420(10) 0.0475(10) 0.0628(13) 0.0009(9) 0.0078(9) -0.0029(8) C16 0.106(2) 0.0622(14) 0.0567(15) -0.0052(11) -0.0256(14) 0.0291(14) C17 0.0434(11) 0.0515(11) 0.0735(14) -0.0010(10) 0.0098(10) 0.0097(9) C18 0.0659(13) 0.0518(11) 0.0462(12) 0.0007(9) 0.0005(10) 0.0143(10) C19 0.0823(15) 0.0503(11) 0.0421(12) -0.0097(9) -0.0128(11) 0.0113(11) C20 0.0494(11) 0.0455(10) 0.0397(10) 0.0046(8) 0.0014(8) 0.0077(8) C21 0.0705(14) 0.0473(11) 0.0720(15) -0.0092(11) 0.0084(12) 0.0203(10) C22 0.151(3) 0.0634(15) 0.0826(18) 0.0054(13) 0.0257(18) 0.0526(16) C23 0.0377(11) 0.0671(13) 0.0965(18) 0.0030(13) 0.0166(12) -0.0062(10) C24 0.0567(12) 0.0446(10) 0.0421(11) -0.0059(8) -0.0028(9) 0.0056(9) C25 0.0670(17) 0.0647(15) 0.120(3) -0.0197(15) -0.0397(17) 0.0272(13) C26 0.0417(12) 0.0689(15) 0.124(2) -0.0081(15) -0.0022(14) 0.0158(11) C27 0.0672(14) 0.0679(13) 0.0637(14) -0.0042(11) 0.0342(12) 0.0011(11) C28 0.0465(12) 0.0682(14) 0.0918(17) 0.0149(12) -0.0035(11) -0.0142(10) C29 0.0550(14) 0.0762(15) 0.0999(19) 0.0026(14) 0.0438(14) 0.0011(12) C30 0.107(2) 0.0654(14) 0.0303(11) -0.0065(10) 0.0060(13) 0.0205(13) C31 0.0786(14) 0.0546(11) 0.0408(11) 0.0016(9) 0.0189(10) 0.0198(10) C32 0.0866(16) 0.0691(14) 0.0545(13) -0.0070(11) 0.0254(12) 0.0295(12) C33 0.0590(13) 0.0702(13) 0.0644(14) 0.0149(11) 0.0206(11) -0.0086(11) C34 0.0686(14) 0.0448(11) 0.0711(15) 0.0081(10) 0.0158(12) 0.0102(10) C35 0.0604(14) 0.0858(16) 0.0719(16) 0.0234(13) -0.0202(12) -0.0059(12) C37 0.0681(14) 0.0686(14) 0.0707(15) 0.0270(12) 0.0007(12) -0.0048(11) C38 0.0585(12) 0.0643(12) 0.0365(11) -0.0062(9) 0.0128(9) 0.0037(10) C40 0.0919(18) 0.0808(15) 0.0398(12) -0.0002(11) 0.0241(12) 0.0102(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4813(12) . ? P1 C9 1.8111(17) . ? P1 C11 1.8133(18) . ? P1 P2 2.2237(8) . ? P2 O2 1.4669(13) . ? P2 N3 1.6504(14) . ? P2 C13 1.8362(16) . ? P2 C4 2.3654(17) . ? N3 C20 1.480(2) . ? N3 C4 1.487(2) . ? C2 C17 1.378(3) . ? C2 C18 1.384(2) . ? C2 C3 1.499(2) . ? C3 C9 1.344(2) . ? C3 C13 1.533(2) . ? C4 C6 1.502(2) . ? C4 C13 1.612(2) . ? C4 H4A 0.9800 . ? C6 C15 1.388(2) . ? C6 C14 1.391(2) . ? C8 C12 1.377(2) . ? C8 C31 1.384(2) . ? C8 C9 1.492(2) . ? C10 C38 1.376(3) . ? C10 C24 1.393(2) . ? C10 C13 1.516(2) . ? C11 C28 1.523(3) . ? C11 C33 1.530(3) . ? C11 H11A 0.9800 . ? C12 C34 1.384(3) . ? C12 H12A 0.9300 . ? C14 C27 1.388(3) . ? C14 H14A 0.9300 . ? C15 C23 1.381(3) . ? C15 H15A 0.9300 . ? C16 C25 1.362(4) . ? C16 C18 1.381(3) . ? C16 H16A 0.9300 . ? C17 C26 1.373(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C30 1.366(3) . ? C19 C24 1.384(2) . ? C19 H19A 0.9300 . ? C20 C35 1.514(3) . ? C20 C22 1.517(3) . ? C20 C37 1.523(3) . ? C21 C34 1.361(3) . ? C21 C32 1.366(3) . ? C21 H21A 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C29 1.372(3) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C26 1.359(4) . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C27 C29 1.375(3) . ? C27 H27A 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9300 . ? C30 C40 1.367(3) . ? C30 H30A 0.9300 . ? C31 C32 1.387(3) . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 C40 1.389(3) . ? C38 H38A 0.9300 . ? C40 H40A 0.9300 . ? 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 C9 116.45(7) . . ? O1 P1 C11 113.96(8) . . ? C9 P1 C11 106.68(8) . . ? O1 P1 P2 114.79(5) . . ? C9 P1 P2 92.20(5) . . ? C11 P1 P2 110.63(7) . . ? O2 P2 N3 121.53(7) . . ? O2 P2 C13 127.12(8) . . ? N3 P2 C13 81.36(7) . . ? O2 P2 P1 114.83(6) . . ? N3 P2 P1 109.25(6) . . ? C13 P2 P1 96.65(5) . . ? O2 P2 C4 136.88(7) . . ? N3 P2 C4 38.52(6) . . ? C13 P2 C4 42.85(6) . . ? P1 P2 C4 108.27(5) . . ? C20 N3 C4 127.18(13) . . ? C20 N3 P2 131.05(11) . . ? C4 N3 P2 97.74(10) . . ? C17 C2 C18 118.62(17) . . ? C17 C2 C3 120.43(16) . . ? C18 C2 C3 120.94(16) . . ? C9 C3 C2 120.38(14) . . ? C9 C3 C13 121.54(14) . . ? C2 C3 C13 118.08(13) . . ? N3 C4 C6 114.76(13) . . ? N3 C4 C13 94.50(12) . . ? C6 C4 C13 117.97(13) . . ? N3 C4 P2 43.74(7) . . ? C6 C4 P2 131.64(11) . . ? C13 C4 P2 50.78(7) . . ? N3 C4 H4A 109.6 . . ? C6 C4 H4A 109.6 . . ? C13 C4 H4A 109.6 . . ? P2 C4 H4A 118.4 . . ? C15 C6 C14 118.66(17) . . ? C15 C6 C4 119.37(16) . . ? C14 C6 C4 121.98(15) . . ? C12 C8 C31 118.32(16) . . ? C12 C8 C9 121.86(15) . . ? C31 C8 C9 119.82(15) . . ? C3 C9 C8 122.72(15) . . ? C3 C9 P1 119.24(12) . . ? C8 C9 P1 118.03(11) . . ? C38 C10 C24 118.59(17) . . ? C38 C10 C13 120.64(16) . . ? C24 C10 C13 120.55(16) . . ? C28 C11 C33 112.60(17) . . ? C28 C11 P1 110.18(13) . . ? C33 C11 P1 112.15(13) . . ? C28 C11 H11A 107.2 . . ? C33 C11 H11A 107.2 . . ? P1 C11 H11A 107.2 . . ? C8 C12 C34 121.19(19) . . ? C8 C12 H12A 119.4 . . ? C34 C12 H12A 119.4 . . ? C10 C13 C3 112.04(12) . . ? C10 C13 C4 114.04(13) . . ? C3 C13 C4 115.65(13) . . ? C10 C13 P2 116.62(11) . . ? C3 C13 P2 109.88(10) . . ? C4 C13 P2 86.36(9) . . ? C27 C14 C6 120.31(18) . . ? C27 C14 H14A 119.8 . . ? C6 C14 H14A 119.8 . . ? C23 C15 C6 120.51(19) . . ? C23 C15 H15A 119.7 . . ? C6 C15 H15A 119.7 . . ? C25 C16 C18 120.3(2) . . ? C25 C16 H16A 119.9 . . ? C18 C16 H16A 119.9 . . ? C26 C17 C2 120.5(2) . . ? C26 C17 H17A 119.7 . . ? C2 C17 H17A 119.7 . . ? C16 C18 C2 120.1(2) . . ? C16 C18 H18A 120.0 . . ? C2 C18 H18A 120.0 . . ? C30 C19 C24 119.7(2) . . ? C30 C19 H19A 120.1 . . ? C24 C19 H19A 120.1 . . ? N3 C20 C35 106.93(15) . . ? N3 C20 C22 109.01(15) . . ? C35 C20 C22 111.38(19) . . ? N3 C20 C37 110.86(15) . . ? C35 C20 C37 109.21(17) . . ? C22 C20 C37 109.44(19) . . ? C34 C21 C32 120.11(18) . . ? C34 C21 H21A 119.9 . . ? C32 C21 H21A 119.9 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C29 C23 C15 120.5(2) . . ? C29 C23 H23A 119.8 . . ? C15 C23 H23A 119.8 . . ? C19 C24 C10 120.6(2) . . ? C19 C24 H24A 119.7 . . ? C10 C24 H24A 119.7 . . ? C26 C25 C16 120.0(2) . . ? C26 C25 H25A 120.0 . . ? C16 C25 H25A 120.0 . . ? C25 C26 C17 120.4(2) . . ? C25 C26 H26A 119.8 . . ? C17 C26 H26A 119.8 . . ? C29 C27 C14 120.2(2) . . ? C29 C27 H27A 119.9 . . ? C14 C27 H27A 119.9 . . ? C11 C28 H28A 109.5 . . ? C11 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C11 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C23 C29 C27 119.8(2) . . ? C23 C29 H29A 120.1 . . ? C27 C29 H29A 120.1 . . ? C19 C30 C40 120.6(2) . . ? C19 C30 H30A 119.7 . . ? C40 C30 H30A 119.7 . . ? C8 C31 C32 120.20(18) . . ? C8 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C21 C32 C31 120.35(19) . . ? C21 C32 H32A 119.8 . . ? C31 C32 H32A 119.8 . . ? C11 C33 H33A 109.5 . . ? C11 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C11 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C21 C34 C12 119.81(19) . . ? C21 C34 H34A 120.1 . . ? C12 C34 H34A 120.1 . . ? C20 C35 H35A 109.5 . . ? C20 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C20 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C20 C37 H37A 109.5 . . ? C20 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C20 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C10 C38 C40 120.5(2) . . ? C10 C38 H38A 119.8 . . ? C40 C38 H38A 119.8 . . ? C30 C40 C38 120.0(2) . . ? C30 C40 H40A 120.0 . . ? C38 C40 H40A 120.0 . . ? 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 O1 P1 P2 O2 108.95(8) . . . . ? C9 P1 P2 O2 -130.48(8) . . . . ? C11 P1 P2 O2 -21.73(9) . . . . ? O1 P1 P2 N3 -31.59(8) . . . . ? C9 P1 P2 N3 88.99(7) . . . . ? C11 P1 P2 N3 -162.26(8) . . . . ? O1 P1 P2 C13 -114.72(8) . . . . ? C9 P1 P2 C13 5.85(7) . . . . ? C11 P1 P2 C13 114.60(8) . . . . ? O1 P1 P2 C4 -72.35(7) . . . . ? C9 P1 P2 C4 48.23(7) . . . . ? C11 P1 P2 C4 156.98(7) . . . . ? O2 P2 N3 C20 -30.79(18) . . . . ? C13 P2 N3 C20 -159.32(16) . . . . ? P1 P2 N3 C20 106.61(14) . . . . ? C4 P2 N3 C20 -158.0(2) . . . . ? O2 P2 N3 C4 127.18(10) . . . . ? C13 P2 N3 C4 -1.35(9) . . . . ? P1 P2 N3 C4 -95.42(9) . . . . ? C17 C2 C3 C9 77.7(2) . . . . ? C18 C2 C3 C9 -102.11(19) . . . . ? C17 C2 C3 C13 -102.49(18) . . . . ? C18 C2 C3 C13 77.6(2) . . . . ? C20 N3 C4 C6 -75.61(19) . . . . ? P2 N3 C4 C6 125.19(12) . . . . ? C20 N3 C4 C13 160.72(15) . . . . ? P2 N3 C4 C13 1.52(11) . . . . ? C20 N3 C4 P2 159.20(19) . . . . ? O2 P2 C4 N3 -83.50(13) . . . . ? C13 P2 C4 N3 178.04(14) . . . . ? P1 P2 C4 N3 98.21(9) . . . . ? O2 P2 C4 C6 -166.70(13) . . . . ? N3 P2 C4 C6 -83.20(16) . . . . ? C13 P2 C4 C6 94.84(16) . . . . ? P1 P2 C4 C6 15.01(15) . . . . ? O2 P2 C4 C13 98.45(12) . . . . ? N3 P2 C4 C13 -178.04(14) . . . . ? P1 P2 C4 C13 -79.83(9) . . . . ? N3 C4 C6 C15 147.23(15) . . . . ? C13 C4 C6 C15 -102.72(18) . . . . ? P2 C4 C6 C15 -163.65(13) . . . . ? N3 C4 C6 C14 -33.2(2) . . . . ? C13 C4 C6 C14 76.8(2) . . . . ? P2 C4 C6 C14 15.9(2) . . . . ? C2 C3 C9 C8 0.3(2) . . . . ? C13 C3 C9 C8 -179.44(14) . . . . ? C2 C3 C9 P1 -178.95(12) . . . . ? C13 C3 C9 P1 1.3(2) . . . . ? C12 C8 C9 C3 72.6(2) . . . . ? C31 C8 C9 C3 -106.4(2) . . . . ? C12 C8 C9 P1 -108.16(17) . . . . ? C31 C8 C9 P1 72.84(19) . . . . ? O1 P1 C9 C3 114.27(13) . . . . ? C11 P1 C9 C3 -117.23(14) . . . . ? P2 P1 C9 C3 -4.92(13) . . . . ? O1 P1 C9 C8 -65.03(14) . . . . ? C11 P1 C9 C8 63.47(14) . . . . ? P2 P1 C9 C8 175.78(12) . . . . ? O1 P1 C11 C28 -56.09(16) . . . . ? C9 P1 C11 C28 173.98(14) . . . . ? P2 P1 C11 C28 75.02(15) . . . . ? O1 P1 C11 C33 177.63(13) . . . . ? C9 P1 C11 C33 47.70(15) . . . . ? P2 P1 C11 C33 -51.26(14) . . . . ? C31 C8 C12 C34 1.2(3) . . . . ? C9 C8 C12 C34 -177.85(17) . . . . ? C38 C10 C13 C3 -90.83(18) . . . . ? C24 C10 C13 C3 83.74(18) . . . . ? C38 C10 C13 C4 135.39(16) . . . . ? C24 C10 C13 C4 -50.04(19) . . . . ? C38 C10 C13 P2 37.00(19) . . . . ? C24 C10 C13 P2 -148.43(13) . . . . ? C9 C3 C13 C10 135.61(16) . . . . ? C2 C3 C13 C10 -44.14(19) . . . . ? C9 C3 C13 C4 -91.40(18) . . . . ? C2 C3 C13 C4 88.85(17) . . . . ? C9 C3 C13 P2 4.28(19) . . . . ? C2 C3 C13 P2 -175.48(12) . . . . ? N3 C4 C13 C10 -118.96(13) . . . . ? C6 C4 C13 C10 119.88(15) . . . . ? P2 C4 C13 C10 -117.60(13) . . . . ? N3 C4 C13 C3 108.98(14) . . . . ? C6 C4 C13 C3 -12.2(2) . . . . ? P2 C4 C13 C3 110.34(13) . . . . ? N3 C4 C13 P2 -1.36(10) . . . . ? C6 C4 C13 P2 -122.52(13) . . . . ? O2 P2 C13 C10 -6.88(16) . . . . ? N3 P2 C13 C10 116.37(12) . . . . ? P1 P2 C13 C10 -135.08(11) . . . . ? C4 P2 C13 C10 115.14(15) . . . . ? O2 P2 C13 C3 121.99(11) . . . . ? N3 P2 C13 C3 -114.76(12) . . . . ? P1 P2 C13 C3 -6.21(11) . . . . ? C4 P2 C13 C3 -115.99(14) . . . . ? O2 P2 C13 C4 -122.02(10) . . . . ? N3 P2 C13 C4 1.23(9) . . . . ? P1 P2 C13 C4 109.78(8) . . . . ? C15 C6 C14 C27 -0.3(3) . . . . ? C4 C6 C14 C27 -179.85(16) . . . . ? C14 C6 C15 C23 -0.2(3) . . . . ? C4 C6 C15 C23 179.39(17) . . . . ? C18 C2 C17 C26 -1.8(3) . . . . ? C3 C2 C17 C26 178.36(17) . . . . ? C25 C16 C18 C2 0.9(3) . . . . ? C17 C2 C18 C16 0.6(3) . . . . ? C3 C2 C18 C16 -179.50(17) . . . . ? C4 N3 C20 C35 164.35(17) . . . . ? P2 N3 C20 C35 -43.5(2) . . . . ? C4 N3 C20 C22 -75.1(2) . . . . ? P2 N3 C20 C22 77.1(2) . . . . ? C4 N3 C20 C37 45.4(2) . . . . ? P2 N3 C20 C37 -162.41(14) . . . . ? C6 C15 C23 C29 0.4(3) . . . . ? C30 C19 C24 C10 -1.3(3) . . . . ? C38 C10 C24 C19 1.3(3) . . . . ? C13 C10 C24 C19 -173.35(15) . . . . ? C18 C16 C25 C26 -1.3(4) . . . . ? C16 C25 C26 C17 0.1(4) . . . . ? C2 C17 C26 C25 1.4(3) . . . . ? C6 C14 C27 C29 0.5(3) . . . . ? C15 C23 C29 C27 -0.2(4) . . . . ? C14 C27 C29 C23 -0.3(3) . . . . ? C24 C19 C30 C40 0.5(3) . . . . ? C12 C8 C31 C32 -1.5(3) . . . . ? C9 C8 C31 C32 177.55(19) . . . . ? C34 C21 C32 C31 0.0(4) . . . . ? C8 C31 C32 C21 0.9(3) . . . . ? C32 C21 C34 C12 -0.4(3) . . . . ? C8 C12 C34 C21 -0.2(3) . . . . ? C24 C10 C38 C40 -0.6(3) . . . . ? C13 C10 C38 C40 174.06(17) . . . . ? C19 C30 C40 C38 0.3(3) . . . . ? C10 C38 C40 C30 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.349 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.041 #========================================================================== data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 865363' #TrackingRef 'mil21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C48 H44 O P4), (C48 H44 O1 P4)' _chemical_formula_sum 'C48 H44 O1.50 P4' _chemical_formula_weight 768.71 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 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 10.7260(10) _cell_length_b 19.139(2) _cell_length_c 19.555(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.130(6) _cell_angle_gamma 90.00 _cell_volume 3991.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 1228 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 18.33 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_device 'Bruker Kappa APEX II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30279 _diffrn_reflns_av_R_equivalents 0.2130 _diffrn_reflns_av_sigmaI/netI 0.3764 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7607 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_cell_refinement 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_data_reduction 'SAINT NT v6.0 (Bruker AXS, 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0120P)^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 7607 _refine_ls_number_parameters 486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2242 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 0.696 _refine_ls_restrained_S_all 0.696 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.13335(12) 0.79525(6) 0.21316(7) 0.0300(4) Uani 1 1 d . . . P2 P 0.02904(14) 0.89348(7) 0.19609(7) 0.0349(4) Uani 1 1 d . . . O2 O 0.0736(7) 0.9528(4) 0.1662(4) 0.073(2) Uiso 0.50 1 d P . . C3 C -0.0112(4) 0.8985(2) 0.2833(2) 0.0251(12) Uani 1 1 d . . . C4 C 0.0462(4) 0.8564(2) 0.3301(2) 0.0254(13) Uani 1 1 d . . . C5 C 0.1398(4) 0.8007(2) 0.3094(2) 0.0237(12) Uani 1 1 d . . . P6 P 0.30292(12) 0.83089(6) 0.34895(7) 0.0294(4) Uani 1 1 d . . . P7 P 0.38714(13) 0.76865(6) 0.27277(7) 0.0298(4) Uani 1 1 d . . . O7 O 0.3568(3) 0.69365(13) 0.26968(14) 0.0350(9) Uani 1 1 d . . . C8 C 0.3037(4) 0.8219(2) 0.2024(2) 0.0242(12) Uani 1 1 d . . . C9 C 0.3274(4) 0.8960(2) 0.2266(2) 0.0233(12) Uani 1 1 d . . . C10 C 0.3229(4) 0.9067(2) 0.2952(2) 0.0241(12) Uani 1 1 d . . . C11 C -0.1129(5) 0.8610(3) 0.1419(3) 0.0506(16) Uani 1 1 d . . . H11A H -0.1386 0.8143 0.1586 0.061 Uiso 1 1 calc R . . C12 C -0.2212(5) 0.9118(3) 0.1387(3) 0.092(2) Uani 1 1 d . . . H12A H -0.2910 0.8938 0.1072 0.138 Uiso 1 1 calc R . . H12B H -0.1945 0.9571 0.1221 0.138 Uiso 1 1 calc R . . H12C H -0.2483 0.9173 0.1847 0.138 Uiso 1 1 calc R . . C13 C -0.0720(5) 0.8550(3) 0.0691(2) 0.071(2) Uani 1 1 d . . . H13A H -0.1442 0.8418 0.0367 0.106 Uiso 1 1 calc R . . H13B H -0.0065 0.8193 0.0687 0.106 Uiso 1 1 calc R . . H13C H -0.0391 0.9001 0.0554 0.106 Uiso 1 1 calc R . . C14 C -0.1050(4) 0.9541(2) 0.2976(2) 0.0289(13) Uani 1 1 d . . . C15 C -0.1990(4) 0.9393(2) 0.3390(2) 0.0393(14) Uani 1 1 d . . . H15A H -0.2025 0.8948 0.3602 0.047 Uiso 1 1 calc R . . C16 C -0.2880(5) 0.9901(3) 0.3494(3) 0.0469(16) Uani 1 1 d . . . H16A H -0.3533 0.9799 0.3770 0.056 Uiso 1 1 calc R . . C17 C -0.2815(5) 1.0545(3) 0.3199(3) 0.0481(16) Uani 1 1 d . . . H17A H -0.3419 1.0892 0.3275 0.058 Uiso 1 1 calc R . . C18 C -0.1893(5) 1.0691(2) 0.2799(3) 0.0462(16) Uani 1 1 d . . . H18A H -0.1856 1.1140 0.2594 0.055 Uiso 1 1 calc R . . C19 C -0.1005(5) 1.0191(2) 0.2686(2) 0.0368(14) Uani 1 1 d . . . H19A H -0.0361 1.0299 0.2406 0.044 Uiso 1 1 calc R . . C20 C 0.0411(4) 0.8658(2) 0.4060(2) 0.0277(13) Uani 1 1 d . . . C21 C -0.0177(4) 0.8182(2) 0.4455(3) 0.0405(15) Uani 1 1 d . . . H21A H -0.0536 0.7769 0.4250 0.049 Uiso 1 1 calc R . . C22 C -0.0238(5) 0.8311(3) 0.5144(3) 0.0518(17) Uani 1 1 d . . . H22A H -0.0684 0.7998 0.5406 0.062 Uiso 1 1 calc R . . C23 C 0.0331(5) 0.8882(3) 0.5456(3) 0.0542(17) Uani 1 1 d . . . H23A H 0.0318 0.8952 0.5936 0.065 Uiso 1 1 calc R . . C24 C 0.0920(5) 0.9350(3) 0.5075(3) 0.0525(17) Uani 1 1 d . . . H24A H 0.1310 0.9752 0.5288 0.063 Uiso 1 1 calc R . . C25 C 0.0948(4) 0.9241(2) 0.4382(3) 0.0395(15) Uani 1 1 d . . . H25A H 0.1348 0.9575 0.4119 0.047 Uiso 1 1 calc R . . C26 C 0.1042(5) 0.7304(2) 0.3385(2) 0.0271(13) Uani 1 1 d . . . C27 C -0.0113(5) 0.7023(2) 0.3167(3) 0.0395(14) Uani 1 1 d . . . H27A H -0.0640 0.7262 0.2822 0.047 Uiso 1 1 calc R . . C28 C -0.0530(5) 0.6412(3) 0.3427(3) 0.0454(16) Uani 1 1 d . . . H28A H -0.1327 0.6227 0.3260 0.054 Uiso 1 1 calc R . . C29 C 0.0224(6) 0.6069(3) 0.3935(3) 0.0550(19) Uani 1 1 d . . . H29A H -0.0057 0.5649 0.4127 0.066 Uiso 1 1 calc R . . C30 C 0.1392(5) 0.6337(3) 0.4167(3) 0.0518(17) Uani 1 1 d . . . H30A H 0.1918 0.6101 0.4515 0.062 Uiso 1 1 calc R . . C31 C 0.1782(5) 0.6949(2) 0.3889(2) 0.0378(14) Uani 1 1 d . . . H31A H 0.2584 0.7131 0.4048 0.045 Uiso 1 1 calc R . . C32 C 0.5568(4) 0.7842(2) 0.2796(2) 0.0324(13) Uani 1 1 d . . . H32A H 0.5738 0.8317 0.2615 0.039 Uiso 1 1 calc R . . C33 C 0.6162(4) 0.7284(2) 0.2372(2) 0.0564(17) Uani 1 1 d . . . H33A H 0.7075 0.7346 0.2420 0.085 Uiso 1 1 calc R . . H33B H 0.5834 0.7331 0.1887 0.085 Uiso 1 1 calc R . . H33C H 0.5959 0.6819 0.2537 0.085 Uiso 1 1 calc R . . C34 C 0.6094(4) 0.7790(2) 0.3554(2) 0.0472(15) Uani 1 1 d . . . H34A H 0.7012 0.7806 0.3591 0.071 Uiso 1 1 calc R . . H34B H 0.5825 0.7349 0.3746 0.071 Uiso 1 1 calc R . . H34C H 0.5782 0.8182 0.3809 0.071 Uiso 1 1 calc R . . C35 C 0.3460(4) 0.7969(2) 0.1353(2) 0.0275(12) Uani 1 1 d . . . C36 C 0.4529(4) 0.8231(2) 0.1103(2) 0.0344(14) Uani 1 1 d . . . H36A H 0.4953 0.8615 0.1331 0.041 Uiso 1 1 calc R . . C37 C 0.4990(5) 0.7950(3) 0.0537(2) 0.0431(15) Uani 1 1 d . . . H37A H 0.5717 0.8147 0.0376 0.052 Uiso 1 1 calc R . . C38 C 0.4417(5) 0.7390(3) 0.0199(3) 0.0509(16) Uani 1 1 d . . . H38A H 0.4742 0.7192 -0.0191 0.061 Uiso 1 1 calc R . . C39 C 0.3352(5) 0.7120(3) 0.0441(2) 0.0464(15) Uani 1 1 d . . . H39A H 0.2937 0.6733 0.0214 0.056 Uiso 1 1 calc R . . C40 C 0.2886(4) 0.7406(2) 0.1006(2) 0.0347(14) Uani 1 1 d . . . H40A H 0.2152 0.7212 0.1161 0.042 Uiso 1 1 calc R . . C41 C 0.3578(5) 0.9509(2) 0.1782(2) 0.0310(13) Uani 1 1 d . . . C42 C 0.4595(5) 0.9958(2) 0.1978(2) 0.0449(16) Uani 1 1 d . . . H42A H 0.5051 0.9908 0.2419 0.054 Uiso 1 1 calc R . . C43 C 0.4941(5) 1.0475(3) 0.1532(3) 0.0587(19) Uani 1 1 d . . . H43A H 0.5612 1.0784 0.1675 0.070 Uiso 1 1 calc R . . C44 C 0.4315(7) 1.0535(3) 0.0894(3) 0.082(2) Uani 1 1 d . . . H44A H 0.4562 1.0883 0.0590 0.098 Uiso 1 1 calc R . . C45 C 0.3321(6) 1.0097(3) 0.0680(3) 0.070(2) Uani 1 1 d . . . H45A H 0.2889 1.0143 0.0233 0.084 Uiso 1 1 calc R . . C46 C 0.2965(5) 0.9589(3) 0.1129(3) 0.0439(15) Uani 1 1 d . . . H46A H 0.2282 0.9289 0.0983 0.053 Uiso 1 1 calc R . . C47 C 0.3225(4) 0.9759(2) 0.3289(2) 0.0264(13) Uani 1 1 d . . . C48 C 0.3895(4) 0.9866(2) 0.3923(2) 0.0347(14) Uani 1 1 d . . . H48A H 0.4403 0.9500 0.4128 0.042 Uiso 1 1 calc R . . C49 C 0.3842(5) 1.0498(3) 0.4266(3) 0.0470(16) Uani 1 1 d . . . H49A H 0.4331 1.0567 0.4695 0.056 Uiso 1 1 calc R . . C50 C 0.3089(5) 1.1018(3) 0.3987(3) 0.0540(18) Uani 1 1 d . . . H50A H 0.3047 1.1452 0.4221 0.065 Uiso 1 1 calc R . . C51 C 0.2387(5) 1.0914(2) 0.3363(3) 0.0465(16) Uani 1 1 d . . . H51A H 0.1846 1.1273 0.3174 0.056 Uiso 1 1 calc R . . C52 C 0.2460(4) 1.0304(2) 0.3017(2) 0.0342(14) Uani 1 1 d . . . H52A H 0.1983 1.0246 0.2582 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0284(9) 0.0279(7) 0.0333(9) -0.0017(7) 0.0022(7) -0.0019(7) P2 0.0336(10) 0.0344(8) 0.0364(10) 0.0025(7) 0.0026(8) 0.0057(7) C3 0.020(3) 0.028(3) 0.027(3) 0.000(2) -0.003(3) 0.001(3) C4 0.016(3) 0.021(3) 0.039(3) -0.005(2) 0.004(3) -0.002(2) C5 0.016(3) 0.021(3) 0.034(3) 0.003(2) 0.000(2) -0.001(2) P6 0.0273(9) 0.0279(8) 0.0326(9) 0.0000(7) 0.0020(7) 0.0024(7) P7 0.0261(9) 0.0265(7) 0.0366(9) -0.0005(7) 0.0023(7) 0.0016(7) O7 0.032(2) 0.0273(19) 0.045(2) -0.0033(17) 0.0013(19) 0.0015(16) C8 0.017(3) 0.029(3) 0.026(3) -0.002(2) -0.003(2) 0.000(2) C9 0.013(3) 0.024(3) 0.033(3) 0.000(2) 0.000(3) -0.006(2) C10 0.011(3) 0.029(3) 0.031(3) 0.001(2) -0.004(2) -0.001(2) C11 0.031(4) 0.068(4) 0.048(4) -0.021(3) -0.020(3) 0.032(3) C12 0.054(5) 0.126(6) 0.092(6) -0.033(5) -0.012(4) -0.003(4) C13 0.056(5) 0.092(5) 0.060(5) -0.021(4) -0.009(4) 0.007(4) C14 0.025(3) 0.031(3) 0.030(3) -0.003(3) 0.000(3) 0.004(3) C15 0.034(4) 0.038(3) 0.044(4) 0.009(3) -0.006(3) 0.005(3) C16 0.030(4) 0.054(4) 0.057(4) -0.004(3) 0.006(3) 0.013(3) C17 0.036(4) 0.040(4) 0.066(5) -0.003(3) -0.005(4) 0.007(3) C18 0.040(4) 0.030(3) 0.068(4) 0.002(3) -0.001(4) 0.005(3) C19 0.032(4) 0.030(3) 0.047(4) 0.000(3) -0.002(3) 0.002(3) C20 0.016(3) 0.033(3) 0.033(3) 0.002(3) 0.003(3) 0.013(3) C21 0.043(4) 0.042(3) 0.038(4) 0.001(3) 0.009(3) 0.014(3) C22 0.055(5) 0.046(4) 0.056(4) 0.008(3) 0.016(4) 0.020(3) C23 0.046(5) 0.078(5) 0.038(4) 0.000(4) 0.006(3) 0.023(4) C24 0.036(4) 0.063(4) 0.056(4) -0.020(4) -0.007(3) 0.012(3) C25 0.030(4) 0.044(3) 0.045(4) -0.009(3) 0.004(3) 0.012(3) C26 0.019(3) 0.030(3) 0.033(3) -0.004(3) 0.006(3) 0.004(3) C27 0.036(4) 0.031(3) 0.051(4) -0.001(3) 0.004(3) 0.003(3) C28 0.046(4) 0.040(4) 0.051(4) -0.006(3) 0.012(4) -0.015(3) C29 0.092(6) 0.028(3) 0.049(4) 0.003(3) 0.024(4) -0.007(4) C30 0.054(5) 0.047(4) 0.052(4) 0.011(3) -0.002(4) -0.001(3) C31 0.030(4) 0.040(3) 0.043(4) 0.006(3) 0.001(3) -0.005(3) C32 0.014(3) 0.037(3) 0.047(4) 0.004(3) 0.005(3) -0.008(2) C33 0.028(4) 0.077(4) 0.064(4) -0.006(4) 0.004(3) 0.015(3) C34 0.025(3) 0.063(4) 0.052(4) -0.007(3) -0.004(3) -0.003(3) C35 0.027(3) 0.024(3) 0.029(3) -0.002(2) -0.006(3) -0.002(3) C36 0.037(4) 0.034(3) 0.032(3) -0.010(3) 0.003(3) -0.007(3) C37 0.041(4) 0.050(3) 0.040(4) -0.007(3) 0.012(3) -0.007(3) C38 0.053(4) 0.062(4) 0.038(4) -0.015(3) 0.009(3) 0.006(3) C39 0.046(4) 0.047(4) 0.045(4) -0.014(3) 0.002(3) -0.012(3) C40 0.025(3) 0.039(3) 0.041(4) -0.009(3) 0.007(3) -0.003(3) C41 0.033(4) 0.032(3) 0.026(3) -0.004(3) -0.008(3) -0.001(3) C42 0.053(4) 0.049(4) 0.031(3) -0.002(3) 0.002(3) -0.012(3) C43 0.081(5) 0.050(4) 0.047(4) -0.004(3) 0.020(4) -0.034(4) C44 0.143(8) 0.052(4) 0.051(5) 0.018(4) 0.011(5) -0.024(5) C45 0.102(6) 0.058(4) 0.046(4) 0.019(4) -0.008(4) -0.011(4) C46 0.050(4) 0.041(3) 0.039(4) 0.000(3) -0.001(3) -0.008(3) C47 0.024(4) 0.028(3) 0.028(3) 0.000(2) 0.004(3) -0.006(3) C48 0.032(4) 0.034(3) 0.036(4) -0.010(3) -0.007(3) 0.005(3) C49 0.048(4) 0.047(4) 0.041(4) -0.015(3) -0.016(3) -0.001(3) C50 0.066(5) 0.037(3) 0.060(5) -0.024(3) 0.015(4) -0.008(3) C51 0.049(4) 0.027(3) 0.064(5) 0.006(3) 0.010(4) 0.003(3) C52 0.030(4) 0.029(3) 0.043(4) -0.005(3) 0.003(3) -0.003(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 1.878(4) . ? P1 C8 1.930(4) . ? P1 P2 2.1949(18) . ? P2 O2 1.385(7) . ? P2 C3 1.805(4) . ? P2 C11 1.866(5) . ? C3 C4 1.322(6) . ? C3 C14 1.511(5) . ? C4 C20 1.502(6) . ? C4 C5 1.547(5) . ? C5 C26 1.526(5) . ? C5 P6 1.925(4) . ? P6 C10 1.817(4) . ? P6 P7 2.1776(16) . ? P7 O7 1.472(3) . ? P7 C32 1.834(4) . ? P7 C8 1.864(4) . ? C8 C9 1.508(5) . ? C8 C35 1.511(5) . ? C9 C10 1.364(5) . ? C9 C41 1.473(6) . ? C10 C47 1.480(5) . ? C11 C12 1.511(6) . ? C11 C13 1.539(6) . ? C11 H11A 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.370(5) . ? C14 C15 1.388(5) . ? C15 C16 1.392(5) . ? C15 H15A 0.9500 . ? C16 C17 1.366(6) . ? C16 H16A 0.9500 . ? C17 C18 1.354(6) . ? C17 H17A 0.9500 . ? C18 C19 1.385(5) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C25 1.377(6) . ? C20 C21 1.387(5) . ? C21 C22 1.380(6) . ? C21 H21A 0.9500 . ? C22 C23 1.362(7) . ? C22 H22A 0.9500 . ? C23 C24 1.364(6) . ? C23 H23A 0.9500 . ? C24 C25 1.375(6) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.375(6) . ? C26 C31 1.376(6) . ? C27 C28 1.370(6) . ? C27 H27A 0.9500 . ? C28 C29 1.379(7) . ? C28 H28A 0.9500 . ? C29 C30 1.384(7) . ? C29 H29A 0.9500 . ? C30 C31 1.375(6) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 C33 1.531(5) . ? C32 C34 1.532(6) . ? C32 H32A 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C40 1.383(5) . ? C35 C36 1.387(5) . ? C36 C37 1.369(5) . ? C36 H36A 0.9500 . ? C37 C38 1.371(6) . ? C37 H37A 0.9500 . ? C38 C39 1.382(6) . ? C38 H38A 0.9500 . ? C39 C40 1.373(5) . ? C39 H39A 0.9500 . ? C40 H40A 0.9500 . ? C41 C46 1.381(6) . ? C41 C42 1.409(6) . ? C42 C43 1.395(6) . ? C42 H42A 0.9500 . ? C43 C44 1.357(7) . ? C43 H43A 0.9500 . ? C44 C45 1.385(7) . ? C44 H44A 0.9500 . ? C45 C46 1.391(6) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 C48 1.380(6) . ? C47 C52 1.397(6) . ? C48 C49 1.387(6) . ? C48 H48A 0.9500 . ? C49 C50 1.359(6) . ? C49 H49A 0.9500 . ? C50 C51 1.378(6) . ? C50 H50A 0.9500 . ? C51 C52 1.357(5) . ? C51 H51A 0.9500 . ? C52 H52A 0.9500 . ? 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 C8 99.3(2) . . ? C5 P1 P2 93.91(14) . . ? C8 P1 P2 103.29(14) . . ? O2 P2 C3 118.9(3) . . ? O2 P2 C11 109.3(4) . . ? C3 P2 C11 106.9(2) . . ? O2 P2 P1 124.9(3) . . ? C3 P2 P1 94.10(16) . . ? C11 P2 P1 99.93(17) . . ? C4 C3 C14 124.9(4) . . ? C4 C3 P2 118.7(3) . . ? C14 C3 P2 116.3(3) . . ? C3 C4 C20 123.2(4) . . ? C3 C4 C5 120.4(4) . . ? C20 C4 C5 115.8(4) . . ? C26 C5 C4 108.3(3) . . ? C26 C5 P1 110.0(3) . . ? C4 C5 P1 110.2(3) . . ? C26 C5 P6 111.5(3) . . ? C4 C5 P6 106.0(3) . . ? P1 C5 P6 110.7(2) . . ? C10 P6 C5 99.5(2) . . ? C10 P6 P7 87.61(14) . . ? C5 P6 P7 89.21(13) . . ? O7 P7 C32 111.98(19) . . ? O7 P7 C8 114.61(19) . . ? C32 P7 C8 111.1(2) . . ? O7 P7 P6 117.10(13) . . ? C32 P7 P6 110.02(16) . . ? C8 P7 P6 90.26(14) . . ? C9 C8 C35 121.0(4) . . ? C9 C8 P7 103.3(3) . . ? C35 C8 P7 107.6(3) . . ? C9 C8 P1 110.1(3) . . ? C35 C8 P1 112.8(3) . . ? P7 C8 P1 99.21(19) . . ? C10 C9 C41 123.9(4) . . ? C10 C9 C8 115.3(4) . . ? C41 C9 C8 120.7(4) . . ? C9 C10 C47 125.1(4) . . ? C9 C10 P6 117.9(3) . . ? C47 C10 P6 116.8(3) . . ? C12 C11 C13 107.6(5) . . ? C12 C11 P2 112.7(4) . . ? C13 C11 P2 104.7(4) . . ? C12 C11 H11A 110.5 . . ? C13 C11 H11A 110.5 . . ? P2 C11 H11A 110.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 119.1(4) . . ? C19 C14 C3 120.6(4) . . ? C15 C14 C3 120.3(4) . . ? C14 C15 C16 119.6(4) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C19 120.4(5) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C14 C19 C18 120.4(5) . . ? C14 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C25 C20 C21 118.0(5) . . ? C25 C20 C4 119.4(4) . . ? C21 C20 C4 122.5(5) . . ? C22 C21 C20 119.9(5) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C23 C22 C21 121.0(5) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 119.5(5) . . ? C22 C23 H23A 120.2 . . ? C24 C23 H23A 120.2 . . ? C23 C24 C25 119.9(6) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C24 C25 C20 121.4(5) . . ? C24 C25 H25A 119.3 . . ? C20 C25 H25A 119.3 . . ? C27 C26 C31 117.5(5) . . ? C27 C26 C5 118.7(5) . . ? C31 C26 C5 123.7(5) . . ? C28 C27 C26 122.5(5) . . ? C28 C27 H27A 118.8 . . ? C26 C27 H27A 118.8 . . ? C27 C28 C29 118.9(5) . . ? C27 C28 H28A 120.5 . . ? C29 C28 H28A 120.5 . . ? C28 C29 C30 120.0(5) . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C31 C30 C29 119.3(5) . . ? C31 C30 H30A 120.4 . . ? C29 C30 H30A 120.4 . . ? C30 C31 C26 121.8(5) . . ? C30 C31 H31A 119.1 . . ? C26 C31 H31A 119.1 . . ? C33 C32 C34 110.4(4) . . ? C33 C32 P7 108.4(3) . . ? C34 C32 P7 108.7(3) . . ? C33 C32 H32A 109.8 . . ? C34 C32 H32A 109.8 . . ? P7 C32 H32A 109.8 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C40 C35 C36 116.8(4) . . ? C40 C35 C8 120.9(4) . . ? C36 C35 C8 121.8(4) . . ? C37 C36 C35 121.7(4) . . ? C37 C36 H36A 119.2 . . ? C35 C36 H36A 119.2 . . ? C36 C37 C38 121.0(5) . . ? C36 C37 H37A 119.5 . . ? C38 C37 H37A 119.5 . . ? C37 C38 C39 118.1(5) . . ? C37 C38 H38A 121.0 . . ? C39 C38 H38A 121.0 . . ? C40 C39 C38 120.8(5) . . ? C40 C39 H39A 119.6 . . ? C38 C39 H39A 119.6 . . ? C39 C40 C35 121.6(5) . . ? C39 C40 H40A 119.2 . . ? C35 C40 H40A 119.2 . . ? C46 C41 C42 117.5(5) . . ? C46 C41 C9 123.8(5) . . ? C42 C41 C9 118.6(5) . . ? C43 C42 C41 120.9(5) . . ? C43 C42 H42A 119.6 . . ? C41 C42 H42A 119.6 . . ? C44 C43 C42 119.7(6) . . ? C44 C43 H43A 120.1 . . ? C42 C43 H43A 120.1 . . ? C43 C44 C45 121.1(6) . . ? C43 C44 H44A 119.5 . . ? C45 C44 H44A 119.5 . . ? C44 C45 C46 119.1(6) . . ? C44 C45 H45A 120.4 . . ? C46 C45 H45A 120.4 . . ? C41 C46 C45 121.7(5) . . ? C41 C46 H46A 119.2 . . ? C45 C46 H46A 119.2 . . ? C48 C47 C52 117.5(4) . . ? C48 C47 C10 120.4(4) . . ? C52 C47 C10 121.8(5) . . ? C47 C48 C49 121.3(5) . . ? C47 C48 H48A 119.4 . . ? C49 C48 H48A 119.4 . . ? C50 C49 C48 119.9(5) . . ? C50 C49 H49A 120.1 . . ? C48 C49 H49A 120.1 . . ? C49 C50 C51 119.6(5) . . ? C49 C50 H50A 120.2 . . ? C51 C50 H50A 120.2 . . ? C52 C51 C50 120.8(5) . . ? C52 C51 H51A 119.6 . . ? C50 C51 H51A 119.6 . . ? C51 C52 C47 120.9(5) . . ? C51 C52 H52A 119.5 . . ? C47 C52 H52A 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 P1 P2 O2 116.2(4) . . . . ? C8 P1 P2 O2 15.7(4) . . . . ? C5 P1 P2 C3 -13.7(2) . . . . ? C8 P1 P2 C3 -114.2(2) . . . . ? C5 P1 P2 C11 -121.7(2) . . . . ? C8 P1 P2 C11 137.9(2) . . . . ? O2 P2 C3 C4 -121.7(5) . . . . ? C11 P2 C3 C4 114.0(4) . . . . ? P1 P2 C3 C4 12.3(4) . . . . ? O2 P2 C3 C14 55.3(5) . . . . ? C11 P2 C3 C14 -68.9(4) . . . . ? P1 P2 C3 C14 -170.6(3) . . . . ? C14 C3 C4 C20 -10.1(8) . . . . ? P2 C3 C4 C20 166.7(4) . . . . ? C14 C3 C4 C5 179.4(4) . . . . ? P2 C3 C4 C5 -3.8(6) . . . . ? C3 C4 C5 C26 -129.6(5) . . . . ? C20 C4 C5 C26 59.3(5) . . . . ? C3 C4 C5 P1 -9.2(5) . . . . ? C20 C4 C5 P1 179.6(3) . . . . ? C3 C4 C5 P6 110.6(4) . . . . ? C20 C4 C5 P6 -60.5(4) . . . . ? C8 P1 C5 C26 -122.4(3) . . . . ? P2 P1 C5 C26 133.5(3) . . . . ? C8 P1 C5 C4 118.3(3) . . . . ? P2 P1 C5 C4 14.2(3) . . . . ? C8 P1 C5 P6 1.4(2) . . . . ? P2 P1 C5 P6 -102.79(19) . . . . ? C26 C5 P6 C10 172.3(3) . . . . ? C4 C5 P6 C10 -70.0(3) . . . . ? P1 C5 P6 C10 49.5(2) . . . . ? C26 C5 P6 P7 84.9(3) . . . . ? C4 C5 P6 P7 -157.5(3) . . . . ? P1 C5 P6 P7 -37.95(19) . . . . ? C10 P6 P7 O7 -156.1(2) . . . . ? C5 P6 P7 O7 -56.5(2) . . . . ? C10 P6 P7 C32 74.6(2) . . . . ? C5 P6 P7 C32 174.1(2) . . . . ? C10 P6 P7 C8 -38.0(2) . . . . ? C5 P6 P7 C8 61.50(19) . . . . ? O7 P7 C8 C9 167.4(2) . . . . ? C32 P7 C8 C9 -64.5(3) . . . . ? P6 P7 C8 C9 47.1(2) . . . . ? O7 P7 C8 C35 -63.6(3) . . . . ? C32 P7 C8 C35 64.6(3) . . . . ? P6 P7 C8 C35 176.2(3) . . . . ? O7 P7 C8 P1 54.0(2) . . . . ? C32 P7 C8 P1 -177.9(2) . . . . ? P6 P7 C8 P1 -66.25(16) . . . . ? C5 P1 C8 C9 -63.8(3) . . . . ? P2 P1 C8 C9 32.5(3) . . . . ? C5 P1 C8 C35 157.8(3) . . . . ? P2 P1 C8 C35 -105.9(3) . . . . ? C5 P1 C8 P7 44.2(2) . . . . ? P2 P1 C8 P7 140.46(14) . . . . ? C35 C8 C9 C10 -159.8(4) . . . . ? P7 C8 C9 C10 -39.5(4) . . . . ? P1 C8 C9 C10 65.7(5) . . . . ? C35 C8 C9 C41 18.0(7) . . . . ? P7 C8 C9 C41 138.3(4) . . . . ? P1 C8 C9 C41 -116.5(4) . . . . ? C41 C9 C10 C47 12.7(7) . . . . ? C8 C9 C10 C47 -169.6(4) . . . . ? C41 C9 C10 P6 -172.5(4) . . . . ? C8 C9 C10 P6 5.2(5) . . . . ? C5 P6 C10 C9 -63.3(4) . . . . ? P7 P6 C10 C9 25.5(4) . . . . ? C5 P6 C10 C47 111.9(4) . . . . ? P7 P6 C10 C47 -159.3(4) . . . . ? O2 P2 C11 C12 -64.5(5) . . . . ? C3 P2 C11 C12 65.4(5) . . . . ? P1 P2 C11 C12 162.8(4) . . . . ? O2 P2 C11 C13 52.2(5) . . . . ? C3 P2 C11 C13 -177.9(3) . . . . ? P1 P2 C11 C13 -80.5(3) . . . . ? C4 C3 C14 C19 136.9(5) . . . . ? P2 C3 C14 C19 -40.0(6) . . . . ? C4 C3 C14 C15 -44.7(7) . . . . ? P2 C3 C14 C15 138.4(4) . . . . ? C19 C14 C15 C16 1.2(8) . . . . ? C3 C14 C15 C16 -177.3(5) . . . . ? C14 C15 C16 C17 -1.2(8) . . . . ? C15 C16 C17 C18 0.7(8) . . . . ? C16 C17 C18 C19 -0.2(9) . . . . ? C15 C14 C19 C18 -0.7(8) . . . . ? C3 C14 C19 C18 177.7(5) . . . . ? C17 C18 C19 C14 0.2(8) . . . . ? C3 C4 C20 C25 -65.2(7) . . . . ? C5 C4 C20 C25 105.7(5) . . . . ? C3 C4 C20 C21 113.8(5) . . . . ? C5 C4 C20 C21 -75.3(6) . . . . ? C25 C20 C21 C22 1.7(7) . . . . ? C4 C20 C21 C22 -177.3(5) . . . . ? C20 C21 C22 C23 -3.7(8) . . . . ? C21 C22 C23 C24 3.2(9) . . . . ? C22 C23 C24 C25 -0.8(8) . . . . ? C23 C24 C25 C20 -1.1(8) . . . . ? C21 C20 C25 C24 0.6(7) . . . . ? C4 C20 C25 C24 179.7(4) . . . . ? C4 C5 C26 C27 62.2(5) . . . . ? P1 C5 C26 C27 -58.3(4) . . . . ? P6 C5 C26 C27 178.4(3) . . . . ? C4 C5 C26 C31 -113.8(5) . . . . ? P1 C5 C26 C31 125.7(4) . . . . ? P6 C5 C26 C31 2.4(5) . . . . ? C31 C26 C27 C28 -0.4(7) . . . . ? C5 C26 C27 C28 -176.7(4) . . . . ? C26 C27 C28 C29 1.0(7) . . . . ? C27 C28 C29 C30 -1.0(8) . . . . ? C28 C29 C30 C31 0.5(8) . . . . ? C29 C30 C31 C26 0.1(8) . . . . ? C27 C26 C31 C30 -0.1(7) . . . . ? C5 C26 C31 C30 175.9(4) . . . . ? O7 P7 C32 C33 35.5(4) . . . . ? C8 P7 C32 C33 -94.0(3) . . . . ? P6 P7 C32 C33 167.6(3) . . . . ? O7 P7 C32 C34 -84.4(3) . . . . ? C8 P7 C32 C34 146.0(3) . . . . ? P6 P7 C32 C34 47.7(3) . . . . ? C9 C8 C35 C40 -156.4(4) . . . . ? P7 C8 C35 C40 85.4(5) . . . . ? P1 C8 C35 C40 -23.0(5) . . . . ? C9 C8 C35 C36 31.8(7) . . . . ? P7 C8 C35 C36 -86.4(5) . . . . ? P1 C8 C35 C36 165.3(4) . . . . ? C40 C35 C36 C37 0.5(7) . . . . ? C8 C35 C36 C37 172.6(4) . . . . ? C35 C36 C37 C38 -0.9(8) . . . . ? C36 C37 C38 C39 0.7(8) . . . . ? C37 C38 C39 C40 -0.2(8) . . . . ? C38 C39 C40 C35 -0.2(8) . . . . ? C36 C35 C40 C39 0.0(7) . . . . ? C8 C35 C40 C39 -172.2(4) . . . . ? C10 C9 C41 C46 -138.8(5) . . . . ? C8 C9 C41 C46 43.6(7) . . . . ? C10 C9 C41 C42 44.7(7) . . . . ? C8 C9 C41 C42 -132.9(5) . . . . ? C46 C41 C42 C43 1.7(7) . . . . ? C9 C41 C42 C43 178.4(4) . . . . ? C41 C42 C43 C44 -1.9(8) . . . . ? C42 C43 C44 C45 1.0(10) . . . . ? C43 C44 C45 C46 0.0(10) . . . . ? C42 C41 C46 C45 -0.7(8) . . . . ? C9 C41 C46 C45 -177.2(5) . . . . ? C44 C45 C46 C41 -0.2(9) . . . . ? C9 C10 C47 C48 -140.6(5) . . . . ? P6 C10 C47 C48 44.6(6) . . . . ? C9 C10 C47 C52 45.8(7) . . . . ? P6 C10 C47 C52 -129.0(4) . . . . ? C52 C47 C48 C49 -2.1(7) . . . . ? C10 C47 C48 C49 -176.0(4) . . . . ? C47 C48 C49 C50 2.0(7) . . . . ? C48 C49 C50 C51 -0.2(8) . . . . ? C49 C50 C51 C52 -1.5(8) . . . . ? C50 C51 C52 C47 1.4(7) . . . . ? C48 C47 C52 C51 0.3(7) . . . . ? C10 C47 C52 C51 174.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.417 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.055 data_m85_fin _database_code_depnum_ccdc_archive 'CCDC 865460' #TrackingRef 'm85_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'Dipolar cycloaddition reactions of 1-alkyl-1,2-diphospholes ' _chemical_name_common ? _chemical_formula_moiety 'C37 H32 P2' _chemical_formula_sum 'C37 H32 P2' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 538.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.185(2) _cell_length_b 10.300(2) _cell_length_c 15.865(4) _cell_angle_alpha 72.942(2) _cell_angle_beta 82.792(2) _cell_angle_gamma 67.620(2) _cell_volume 1471.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4405 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.85 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9422 _exptl_absorpt_correction_T_max 0.9502 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type SmartApexII _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14791 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5684 _reflns_number_gt 4529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.9375P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5684 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1397 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.93965(6) 0.09310(6) 0.37091(4) 0.03950(18) Uani 1 1 d . . . P2 P 0.91261(6) 0.26617(6) 0.43197(4) 0.03935(18) Uani 1 1 d . . . C1 C 1.0656(2) 0.1311(2) 0.27783(14) 0.0381(5) Uani 1 1 d . . . C2 C 0.9055(2) 0.2183(2) 0.25542(14) 0.0361(5) Uani 1 1 d . . . C3 C 0.8462(2) 0.3771(2) 0.25628(14) 0.0371(5) Uani 1 1 d . . . C4 C 0.8421(2) 0.4122(2) 0.33246(14) 0.0372(5) Uani 1 1 d . . . C5 C 0.7512(3) 0.2633(3) 0.50187(16) 0.0489(6) Uani 1 1 d . . . C6 C 0.7090(4) 0.3786(4) 0.5527(2) 0.0664(8) Uani 1 1 d . . . C7 C 0.6260(3) 0.2732(5) 0.4548(2) 0.0691(9) Uani 1 1 d . . . C8 C 0.7907(2) 0.5621(2) 0.34417(14) 0.0405(5) Uani 1 1 d . . . C13 C 0.6542(3) 0.6605(3) 0.32009(16) 0.0464(6) Uani 1 1 d . . . C9 C 0.8742(3) 0.6037(3) 0.38582(18) 0.0534(6) Uani 1 1 d . . . C12 C 0.6029(3) 0.7945(3) 0.33824(18) 0.0595(7) Uani 1 1 d . . . C10 C 0.8224(4) 0.7387(3) 0.4035(2) 0.0646(8) Uani 1 1 d . . . C11 C 0.6878(4) 0.8327(3) 0.3809(2) 0.0658(8) Uani 1 1 d . . . C14 C 0.7985(3) 0.4941(3) 0.17218(14) 0.0442(5) Uani 1 1 d . . . C15 C 0.8603(4) 0.5987(3) 0.1428(2) 0.0623(8) Uani 1 1 d . . . C19 C 0.6854(3) 0.5070(3) 0.12412(18) 0.0594(7) Uani 1 1 d . . . C17 C 0.7008(6) 0.7219(5) 0.0208(2) 0.1005(16) Uani 1 1 d . . . C16 C 0.8101(5) 0.7126(4) 0.0672(3) 0.0908(14) Uani 1 1 d . . . C18 C 0.6392(5) 0.6215(4) 0.0490(2) 0.0826(12) Uani 1 1 d . . . C20 C 0.8418(2) 0.1799(2) 0.18975(15) 0.0414(5) Uani 1 1 d . . . C25 C 0.8991(3) 0.1875(3) 0.10480(17) 0.0540(6) Uani 1 1 d . . . C21 C 0.7241(3) 0.1412(3) 0.21106(19) 0.0570(7) Uani 1 1 d . . . C24 C 0.8377(4) 0.1556(4) 0.0442(2) 0.0694(9) Uani 1 1 d . . . C23 C 0.7218(4) 0.1162(4) 0.0668(2) 0.0791(10) Uani 1 1 d . . . C22 C 0.6635(4) 0.1092(4) 0.1497(2) 0.0783(10) Uani 1 1 d . . . C26 C 1.1575(2) 0.2137(2) 0.28167(16) 0.0412(5) Uani 1 1 d . . . C27 C 1.1727(3) 0.3198(3) 0.20806(18) 0.0480(6) Uani 1 1 d . . . C31 C 1.2387(3) 0.1769(3) 0.3552(2) 0.0537(6) Uani 1 1 d . . . C30 C 1.3302(3) 0.2474(4) 0.3552(2) 0.0704(9) Uani 1 1 d . . . C28 C 1.2668(3) 0.3888(3) 0.2076(2) 0.0626(7) Uani 1 1 d . . . C29 C 1.3435(3) 0.3527(4) 0.2819(3) 0.0714(9) Uani 1 1 d . . . C32 C 1.1435(2) -0.0008(2) 0.24193(15) 0.0403(5) Uani 1 1 d . . . C33 C 1.2760(3) -0.0187(3) 0.20077(17) 0.0475(6) Uani 1 1 d . . . C37 C 1.0889(3) -0.1088(3) 0.24924(18) 0.0518(6) Uani 1 1 d . . . C35 C 1.2939(3) -0.2437(3) 0.17671(19) 0.0595(7) Uani 1 1 d . . . C36 C 1.1627(3) -0.2281(3) 0.2170(2) 0.0572(7) Uani 1 1 d . . . C34 C 1.3505(3) -0.1392(3) 0.16862(19) 0.0560(7) Uani 1 1 d . . . H5 H 0.782(3) 0.168(3) 0.5493(18) 0.053(7) Uiso 1 1 d . . . H33 H 1.307(3) 0.051(3) 0.1925(17) 0.046(7) Uiso 1 1 d . . . H27 H 1.120(3) 0.346(3) 0.1562(17) 0.044(7) Uiso 1 1 d . . . H28 H 1.286(3) 0.462(3) 0.157(2) 0.063(8) Uiso 1 1 d . . . H29 H 1.408(4) 0.395(4) 0.281(2) 0.089(11) Uiso 1 1 d . . . H36 H 1.124(3) -0.298(3) 0.2264(19) 0.059(8) Uiso 1 1 d . . . H34 H 1.440(3) -0.147(3) 0.1418(19) 0.057(8) Uiso 1 1 d . . . H37 H 1.001(3) -0.101(3) 0.2762(19) 0.056(8) Uiso 1 1 d . . . H35 H 1.343(4) -0.325(4) 0.154(2) 0.083(10) Uiso 1 1 d . . . H12 H 0.499(3) 0.860(3) 0.3248(19) 0.062(8) Uiso 1 1 d . . . H13 H 0.593(3) 0.631(3) 0.2966(17) 0.045(7) Uiso 1 1 d . . . H9 H 0.962(3) 0.538(3) 0.4004(19) 0.062(8) Uiso 1 1 d . . . H11 H 0.661(3) 0.926(3) 0.394(2) 0.069(9) Uiso 1 1 d . . . H10 H 0.887(4) 0.760(3) 0.437(2) 0.082(10) Uiso 1 1 d . . . H19 H 0.634(3) 0.434(3) 0.145(2) 0.064(8) Uiso 1 1 d . . . H15 H 0.938(3) 0.595(3) 0.171(2) 0.068(10) Uiso 1 1 d . . . H17 H 0.665(5) 0.799(5) -0.030(3) 0.121(14) Uiso 1 1 d . . . H16 H 0.851(4) 0.773(5) 0.057(3) 0.100(14) Uiso 1 1 d . . . H18 H 0.565(4) 0.621(4) 0.018(3) 0.102(13) Uiso 1 1 d . . . H21 H 0.687(3) 0.137(3) 0.266(2) 0.056(8) Uiso 1 1 d . . . H25 H 0.982(3) 0.213(3) 0.0903(19) 0.059(8) Uiso 1 1 d . . . H24 H 0.882(4) 0.160(4) -0.006(2) 0.078(10) Uiso 1 1 d . . . H23 H 0.681(4) 0.092(4) 0.028(2) 0.088(11) Uiso 1 1 d . . . H22 H 0.567(5) 0.082(4) 0.174(3) 0.117(14) Uiso 1 1 d . . . H31 H 1.229(3) 0.110(3) 0.403(2) 0.067(9) Uiso 1 1 d . . . H30 H 1.383(5) 0.217(5) 0.415(3) 0.123(14) Uiso 1 1 d . . . H62 H 0.780(4) 0.374(4) 0.580(3) 0.087(12) Uiso 1 1 d . . . H61 H 0.672(4) 0.478(4) 0.510(3) 0.099(12) Uiso 1 1 d . . . H63 H 0.644(4) 0.364(4) 0.596(2) 0.080(10) Uiso 1 1 d . . . H73 H 0.546(3) 0.268(3) 0.500(2) 0.071(9) Uiso 1 1 d . . . H72 H 0.589(4) 0.370(4) 0.403(3) 0.092(11) Uiso 1 1 d . . . H71 H 0.642(5) 0.190(5) 0.432(3) 0.131(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0416(3) 0.0387(3) 0.0350(3) -0.0070(2) -0.0037(2) -0.0123(3) P2 0.0375(3) 0.0447(3) 0.0332(3) -0.0097(2) -0.0060(2) -0.0109(2) C1 0.0362(11) 0.0387(11) 0.0385(11) -0.0121(9) -0.0040(9) -0.0103(9) C2 0.0339(11) 0.0387(11) 0.0348(11) -0.0098(9) -0.0022(8) -0.0116(9) C3 0.0332(11) 0.0379(11) 0.0369(11) -0.0066(9) -0.0035(9) -0.0107(9) C4 0.0341(11) 0.0395(12) 0.0368(11) -0.0088(9) -0.0028(9) -0.0123(9) C5 0.0467(13) 0.0557(15) 0.0381(12) -0.0087(11) 0.0011(10) -0.0154(12) C6 0.066(2) 0.083(2) 0.0497(17) -0.0285(16) 0.0093(15) -0.0210(18) C7 0.0466(16) 0.102(3) 0.0651(19) -0.0286(19) 0.0069(14) -0.0314(17) C8 0.0469(13) 0.0423(12) 0.0327(11) -0.0092(9) 0.0017(9) -0.0180(10) C13 0.0521(14) 0.0441(13) 0.0411(12) -0.0131(10) -0.0046(11) -0.0129(11) C9 0.0570(16) 0.0545(16) 0.0554(15) -0.0148(12) -0.0084(13) -0.0251(13) C12 0.0690(18) 0.0467(15) 0.0495(15) -0.0115(12) -0.0008(13) -0.0077(13) C10 0.086(2) 0.0605(18) 0.0621(17) -0.0214(14) -0.0079(16) -0.0364(17) C11 0.101(2) 0.0455(15) 0.0562(16) -0.0200(13) 0.0011(16) -0.0278(16) C14 0.0473(13) 0.0410(12) 0.0330(11) -0.0098(9) 0.0024(9) -0.0047(10) C15 0.0653(18) 0.0464(15) 0.0590(17) -0.0061(13) 0.0143(14) -0.0133(13) C19 0.0627(17) 0.0547(16) 0.0453(14) -0.0150(12) -0.0142(12) 0.0009(14) C17 0.123(4) 0.075(3) 0.0394(17) 0.0072(17) 0.001(2) 0.016(2) C16 0.111(3) 0.0520(19) 0.075(2) 0.0022(17) 0.040(2) -0.019(2) C18 0.095(3) 0.072(2) 0.0452(17) -0.0109(16) -0.0232(17) 0.011(2) C20 0.0437(12) 0.0382(12) 0.0395(12) -0.0100(9) -0.0096(9) -0.0094(10) C25 0.0505(15) 0.0649(17) 0.0440(14) -0.0200(12) -0.0031(11) -0.0134(13) C21 0.0577(16) 0.0708(18) 0.0492(15) -0.0098(13) -0.0092(13) -0.0327(14) C24 0.072(2) 0.086(2) 0.0477(16) -0.0312(15) -0.0123(15) -0.0121(17) C23 0.097(3) 0.080(2) 0.072(2) -0.0280(17) -0.0344(19) -0.029(2) C22 0.084(2) 0.093(2) 0.075(2) -0.0128(18) -0.0260(18) -0.050(2) C26 0.0336(11) 0.0430(12) 0.0498(13) -0.0197(10) 0.0001(9) -0.0118(9) C27 0.0449(13) 0.0467(14) 0.0546(15) -0.0182(11) 0.0008(11) -0.0159(11) C31 0.0451(14) 0.0621(17) 0.0561(16) -0.0171(13) -0.0061(12) -0.0194(13) C30 0.0527(16) 0.093(2) 0.081(2) -0.0353(19) -0.0106(15) -0.0315(16) C28 0.0604(17) 0.0538(16) 0.081(2) -0.0221(15) 0.0098(15) -0.0292(14) C29 0.0574(18) 0.081(2) 0.098(3) -0.039(2) 0.0044(17) -0.0392(17) C32 0.0396(12) 0.0393(12) 0.0381(11) -0.0104(9) -0.0050(9) -0.0088(9) C33 0.0453(13) 0.0479(14) 0.0487(14) -0.0175(11) 0.0001(11) -0.0131(11) C37 0.0507(15) 0.0483(14) 0.0565(15) -0.0187(12) -0.0015(12) -0.0144(12) C35 0.0701(18) 0.0495(15) 0.0548(15) -0.0242(13) -0.0036(13) -0.0089(14) C36 0.0673(18) 0.0443(15) 0.0637(17) -0.0201(13) -0.0037(14) -0.0193(13) C34 0.0498(15) 0.0594(17) 0.0562(16) -0.0254(13) 0.0045(12) -0.0111(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.884(2) . ? P1 C2 1.890(2) . ? P1 P2 2.1829(9) . ? P2 C4 1.827(2) . ? P2 C5 1.869(3) . ? C1 C26 1.501(3) . ? C1 C32 1.523(3) . ? C1 C2 1.561(3) . ? C2 C20 1.506(3) . ? C2 C3 1.516(3) . ? C3 C4 1.351(3) . ? C3 C14 1.497(3) . ? C4 C8 1.491(3) . ? C5 C7 1.513(4) . ? C5 C6 1.527(4) . ? C8 C9 1.388(3) . ? C8 C13 1.392(3) . ? C13 C12 1.381(4) . ? C9 C10 1.388(4) . ? C12 C11 1.386(4) . ? C10 C11 1.362(5) . ? C14 C15 1.386(4) . ? C14 C19 1.404(4) . ? C15 C16 1.395(5) . ? C19 C18 1.388(4) . ? C17 C18 1.348(7) . ? C17 C16 1.368(7) . ? C20 C21 1.377(4) . ? C20 C25 1.392(4) . ? C25 C24 1.384(4) . ? C21 C22 1.388(4) . ? C24 C23 1.364(5) . ? C23 C22 1.367(5) . ? C26 C27 1.384(4) . ? C26 C31 1.390(4) . ? C27 C28 1.391(4) . ? C31 C30 1.382(4) . ? C30 C29 1.371(5) . ? C28 C29 1.376(5) . ? C32 C37 1.393(4) . ? C32 C33 1.393(3) . ? C33 C34 1.390(4) . ? C37 C36 1.381(4) . ? C35 C34 1.371(4) . ? C35 C36 1.379(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C2 48.86(9) . . ? C1 P1 P2 99.94(7) . . ? C2 P1 P2 94.48(7) . . ? C4 P2 C5 103.89(11) . . ? C4 P2 P1 93.92(8) . . ? C5 P2 P1 99.80(9) . . ? C26 C1 C32 113.27(18) . . ? C26 C1 C2 118.52(18) . . ? C32 C1 C2 118.20(18) . . ? C26 C1 P1 121.41(16) . . ? C32 C1 P1 111.80(16) . . ? C2 C1 P1 65.79(11) . . ? C20 C2 C3 116.14(18) . . ? C20 C2 C1 118.05(18) . . ? C3 C2 C1 117.25(18) . . ? C20 C2 P1 118.80(16) . . ? C3 C2 P1 111.40(14) . . ? C1 C2 P1 65.35(11) . . ? C4 C3 C14 120.4(2) . . ? C4 C3 C2 119.65(19) . . ? C14 C3 C2 119.89(18) . . ? C3 C4 C8 126.4(2) . . ? C3 C4 P2 118.88(17) . . ? C8 C4 P2 114.66(15) . . ? C7 C5 C6 111.6(3) . . ? C7 C5 P2 115.81(19) . . ? C6 C5 P2 110.1(2) . . ? C9 C8 C13 118.0(2) . . ? C9 C8 C4 120.6(2) . . ? C13 C8 C4 121.2(2) . . ? C12 C13 C8 120.9(3) . . ? C8 C9 C10 120.9(3) . . ? C13 C12 C11 120.0(3) . . ? C11 C10 C9 120.4(3) . . ? C10 C11 C12 119.9(3) . . ? C15 C14 C19 118.1(3) . . ? C15 C14 C3 120.1(2) . . ? C19 C14 C3 121.6(2) . . ? C14 C15 C16 120.1(4) . . ? C18 C19 C14 120.0(4) . . ? C18 C17 C16 119.8(3) . . ? C17 C16 C15 120.7(4) . . ? C17 C18 C19 121.3(4) . . ? C21 C20 C25 118.6(2) . . ? C21 C20 C2 121.2(2) . . ? C25 C20 C2 120.2(2) . . ? C24 C25 C20 119.8(3) . . ? C20 C21 C22 121.1(3) . . ? C23 C24 C25 120.8(3) . . ? C24 C23 C22 120.2(3) . . ? C23 C22 C21 119.5(3) . . ? C27 C26 C31 118.6(2) . . ? C27 C26 C1 119.9(2) . . ? C31 C26 C1 121.2(2) . . ? C26 C27 C28 120.9(3) . . ? C30 C31 C26 120.5(3) . . ? C29 C30 C31 120.2(3) . . ? C29 C28 C27 119.4(3) . . ? C30 C29 C28 120.5(3) . . ? C37 C32 C33 117.0(2) . . ? C37 C32 C1 122.7(2) . . ? C33 C32 C1 120.2(2) . . ? C34 C33 C32 121.5(3) . . ? C36 C37 C32 121.4(3) . . ? C34 C35 C36 119.4(3) . . ? C35 C36 C37 120.5(3) . . ? C35 C34 C33 120.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 P1 P2 C4 59.57(10) . . . . ? C2 P1 P2 C4 10.59(10) . . . . ? C1 P1 P2 C5 164.41(10) . . . . ? C2 P1 P2 C5 115.42(11) . . . . ? C2 P1 C1 C26 109.8(2) . . . . ? P2 P1 C1 C26 22.54(18) . . . . ? C2 P1 C1 C32 -112.22(19) . . . . ? P2 P1 C1 C32 160.52(14) . . . . ? P2 P1 C1 C2 -87.26(11) . . . . ? C26 C1 C2 C20 135.2(2) . . . . ? C32 C1 C2 C20 -8.1(3) . . . . ? P1 C1 C2 C20 -110.86(19) . . . . ? C26 C1 C2 C3 -11.5(3) . . . . ? C32 C1 C2 C3 -154.81(19) . . . . ? P1 C1 C2 C3 102.43(17) . . . . ? C26 C1 C2 P1 -113.95(19) . . . . ? C32 C1 C2 P1 102.77(19) . . . . ? C1 P1 C2 C20 109.8(2) . . . . ? P2 P1 C2 C20 -150.94(16) . . . . ? C1 P1 C2 C3 -111.18(19) . . . . ? P2 P1 C2 C3 -11.89(14) . . . . ? P2 P1 C2 C1 99.29(11) . . . . ? C20 C2 C3 C4 148.8(2) . . . . ? C1 C2 C3 C4 -63.9(3) . . . . ? P1 C2 C3 C4 8.6(3) . . . . ? C20 C2 C3 C14 -33.8(3) . . . . ? C1 C2 C3 C14 113.5(2) . . . . ? P1 C2 C3 C14 -174.06(16) . . . . ? C14 C3 C4 C8 1.1(3) . . . . ? C2 C3 C4 C8 178.4(2) . . . . ? C14 C3 C4 P2 -175.87(16) . . . . ? C2 C3 C4 P2 1.5(3) . . . . ? C5 P2 C4 C3 -109.95(19) . . . . ? P1 P2 C4 C3 -8.83(18) . . . . ? C5 P2 C4 C8 72.77(18) . . . . ? P1 P2 C4 C8 173.89(15) . . . . ? C4 P2 C5 C7 44.5(3) . . . . ? P1 P2 C5 C7 -52.1(2) . . . . ? C4 P2 C5 C6 -83.2(2) . . . . ? P1 P2 C5 C6 -179.8(2) . . . . ? C3 C4 C8 C9 -128.5(3) . . . . ? P2 C4 C8 C9 48.5(3) . . . . ? C3 C4 C8 C13 56.5(3) . . . . ? P2 C4 C8 C13 -126.4(2) . . . . ? C9 C8 C13 C12 -0.9(4) . . . . ? C4 C8 C13 C12 174.2(2) . . . . ? C13 C8 C9 C10 0.5(4) . . . . ? C4 C8 C9 C10 -174.6(2) . . . . ? C8 C13 C12 C11 0.1(4) . . . . ? C8 C9 C10 C11 0.5(5) . . . . ? C9 C10 C11 C12 -1.3(5) . . . . ? C13 C12 C11 C10 1.0(4) . . . . ? C4 C3 C14 C15 56.4(3) . . . . ? C2 C3 C14 C15 -121.0(2) . . . . ? C4 C3 C14 C19 -119.5(3) . . . . ? C2 C3 C14 C19 63.1(3) . . . . ? C19 C14 C15 C16 -0.1(4) . . . . ? C3 C14 C15 C16 -176.2(3) . . . . ? C15 C14 C19 C18 0.6(4) . . . . ? C3 C14 C19 C18 176.5(2) . . . . ? C18 C17 C16 C15 1.2(6) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C16 C17 C18 C19 -0.7(6) . . . . ? C14 C19 C18 C17 -0.1(5) . . . . ? C3 C2 C20 C21 -88.9(3) . . . . ? C1 C2 C20 C21 124.0(2) . . . . ? P1 C2 C20 C21 48.3(3) . . . . ? C3 C2 C20 C25 89.0(3) . . . . ? C1 C2 C20 C25 -58.0(3) . . . . ? P1 C2 C20 C25 -133.8(2) . . . . ? C21 C20 C25 C24 -0.4(4) . . . . ? C2 C20 C25 C24 -178.4(2) . . . . ? C25 C20 C21 C22 0.4(4) . . . . ? C2 C20 C21 C22 178.4(3) . . . . ? C20 C25 C24 C23 -0.2(5) . . . . ? C25 C24 C23 C22 0.7(5) . . . . ? C24 C23 C22 C21 -0.6(6) . . . . ? C20 C21 C22 C23 0.0(5) . . . . ? C32 C1 C26 C27 85.8(3) . . . . ? C2 C1 C26 C27 -59.2(3) . . . . ? P1 C1 C26 C27 -136.82(19) . . . . ? C32 C1 C26 C31 -88.1(3) . . . . ? C2 C1 C26 C31 126.9(2) . . . . ? P1 C1 C26 C31 49.3(3) . . . . ? C31 C26 C27 C28 -0.3(4) . . . . ? C1 C26 C27 C28 -174.4(2) . . . . ? C27 C26 C31 C30 1.5(4) . . . . ? C1 C26 C31 C30 175.4(2) . . . . ? C26 C31 C30 C29 -1.2(5) . . . . ? C26 C27 C28 C29 -1.2(4) . . . . ? C31 C30 C29 C28 -0.4(5) . . . . ? C27 C28 C29 C30 1.6(5) . . . . ? C26 C1 C32 C37 166.5(2) . . . . ? C2 C1 C32 C37 -48.4(3) . . . . ? P1 C1 C32 C37 25.0(3) . . . . ? C26 C1 C32 C33 -12.5(3) . . . . ? C2 C1 C32 C33 132.6(2) . . . . ? P1 C1 C32 C33 -154.08(19) . . . . ? C37 C32 C33 C34 -0.2(4) . . . . ? C1 C32 C33 C34 179.0(2) . . . . ? C33 C32 C37 C36 -0.1(4) . . . . ? C1 C32 C37 C36 -179.2(2) . . . . ? C34 C35 C36 C37 -0.2(4) . . . . ? C32 C37 C36 C35 0.2(4) . . . . ? C36 C35 C34 C33 -0.1(4) . . . . ? C32 C33 C34 C35 0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.329 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.041