# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Alan H. Cowley' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Zheng Lu.' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Michael Findlater' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_contact_author_email cowley@mail.utexas.edu _publ_contact_author_fax 512-471-6822 _publ_contact_author_phone 512-471-7710 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof. Alan H. Cowley' _publ_contact_letter ; Please consider this CIF submission for publication in ; # 2. TITLE AND AUTHOR LIST _publ_section_title ; A beta-diketiminato hydroxyphosphenium cation: phosphinous acid/secondary phosphine oxide tautomerism revisited ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; data_try1 _database_code_depnum_ccdc_archive 'CCDC 664930' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H43 Br N2 P, C F3 O3 S' _chemical_formula_sum 'C31 H43 Br F3 N2 O3 P S' _chemical_formula_weight 691.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -p2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.568(5) _cell_length_b 12.712(5) _cell_length_c 18.815(5) _cell_angle_alpha 90.000 _cell_angle_beta 110.769(5) _cell_angle_gamma 90.000 _cell_volume 3257.9(19) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8475 _exptl_absorpt_correction_T_max 0.8944 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \f-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13329 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.44 _reflns_number_total 7428 _reflns_number_gt 5108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.9573P] 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 7428 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.003 _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 C1 C 0.2321(2) 0.0674(2) 0.17881(16) 0.0228(6) Uani 1 1 d . . . C2 C 0.3330(2) 0.0705(2) 0.22295(17) 0.0233(6) Uani 1 1 d . . . C3 C 0.3662(2) 0.1013(2) 0.29836(17) 0.0220(6) Uani 1 1 d . . . C4 C 0.1966(2) -0.0028(2) 0.11154(18) 0.0312(7) Uani 1 1 d . . . H4A H 0.1256 -0.0132 0.0971 0.047 Uiso 1 1 calc R . . H4B H 0.2301 -0.0708 0.1240 0.047 Uiso 1 1 calc R . . H4C H 0.2105 0.0294 0.0691 0.047 Uiso 1 1 calc R . . C5 C 0.4043(2) 0.0231(2) 0.18942(19) 0.0318(7) Uani 1 1 d . . . H5A H 0.4700 0.0523 0.2154 0.048 Uiso 1 1 calc R . . H5B H 0.3827 0.0398 0.1351 0.048 Uiso 1 1 calc R . . H5C H 0.4063 -0.0534 0.1961 0.048 Uiso 1 1 calc R . . C6 C 0.4691(2) 0.0823(3) 0.34988(19) 0.0328(8) Uani 1 1 d . . . H6A H 0.5116 0.1381 0.3429 0.049 Uiso 1 1 calc R . . H6B H 0.4914 0.0141 0.3379 0.049 Uiso 1 1 calc R . . H6C H 0.4722 0.0823 0.4028 0.049 Uiso 1 1 calc R . . C7 C 0.0616(2) 0.1295(2) 0.14963(16) 0.0220(6) Uani 1 1 d . . . C8 C 0.0321(2) 0.1813(2) 0.07865(17) 0.0251(7) Uani 1 1 d . . . C9 C -0.0688(2) 0.1834(2) 0.03646(18) 0.0299(7) Uani 1 1 d . . . H9 H -0.0911 0.2163 -0.0120 0.036 Uiso 1 1 calc R . . C10 C -0.1363(2) 0.1393(2) 0.06316(19) 0.0322(8) Uani 1 1 d . . . H10 H -0.2043 0.1424 0.0335 0.039 Uiso 1 1 calc R . . C11 C -0.1052(2) 0.0901(2) 0.13345(19) 0.0327(8) Uani 1 1 d . . . H11 H -0.1526 0.0603 0.1515 0.039 Uiso 1 1 calc R . . C12 C -0.0061(2) 0.0834(2) 0.17825(17) 0.0245(6) Uani 1 1 d . . . C13 C 0.1000(2) 0.2367(2) 0.04482(18) 0.0304(7) Uani 1 1 d . . . H13 H 0.1693 0.2276 0.0802 0.036 Uiso 1 1 calc R . . C14 C 0.0762(3) 0.3550(2) 0.0363(2) 0.0389(8) Uani 1 1 d . . . H14A H 0.0106 0.3654 -0.0020 0.058 Uiso 1 1 calc R . . H14B H 0.1249 0.3914 0.0202 0.058 Uiso 1 1 calc R . . H14C H 0.0779 0.3835 0.0851 0.058 Uiso 1 1 calc R . . C15 C 0.0905(3) 0.1911(3) -0.0331(2) 0.0451(9) Uani 1 1 d . . . H15A H 0.1002 0.1148 -0.0288 0.068 Uiso 1 1 calc R . . H15B H 0.1402 0.2229 -0.0503 0.068 Uiso 1 1 calc R . . H15C H 0.0249 0.2066 -0.0698 0.068 Uiso 1 1 calc R . . C16 C 0.0228(2) 0.0244(2) 0.25315(18) 0.0290(7) Uani 1 1 d . . . H16 H 0.0942 0.0370 0.2816 0.035 Uiso 1 1 calc R . . C17 C -0.0347(3) 0.0660(3) 0.3013(2) 0.0503(10) Uani 1 1 d . . . H17A H -0.0258 0.1423 0.3074 0.075 Uiso 1 1 calc R . . H17B H -0.0106 0.0322 0.3514 0.075 Uiso 1 1 calc R . . H17C H -0.1046 0.0500 0.2759 0.075 Uiso 1 1 calc R . . C18 C 0.0073(3) -0.0937(2) 0.2383(2) 0.0466(10) Uani 1 1 d . . . H18A H -0.0609 -0.1069 0.2056 0.070 Uiso 1 1 calc R . . H18B H 0.0215 -0.1308 0.2867 0.070 Uiso 1 1 calc R . . H18C H 0.0515 -0.1191 0.2131 0.070 Uiso 1 1 calc R . . C19 C 0.3284(2) 0.1542(2) 0.41233(16) 0.0211(6) Uani 1 1 d . . . C20 C 0.3721(2) 0.2464(2) 0.45104(17) 0.0225(6) Uani 1 1 d . . . C21 C 0.3908(2) 0.2505(2) 0.52909(18) 0.0288(7) Uani 1 1 d . . . H21 H 0.4192 0.3124 0.5564 0.035 Uiso 1 1 calc R . . C22 C 0.3695(2) 0.1676(2) 0.56751(19) 0.0302(7) Uani 1 1 d . . . H22 H 0.3818 0.1730 0.6205 0.036 Uiso 1 1 calc R . . C23 C 0.3298(2) 0.0761(2) 0.52853(18) 0.0284(7) Uani 1 1 d . . . H23 H 0.3163 0.0186 0.5555 0.034 Uiso 1 1 calc R . . C24 C 0.3091(2) 0.0669(2) 0.45029(17) 0.0243(6) Uani 1 1 d . . . C25 C 0.4010(2) 0.3392(2) 0.41343(18) 0.0257(7) Uani 1 1 d . . . H25 H 0.3908 0.3193 0.3597 0.031 Uiso 1 1 calc R . . C26 C 0.3331(2) 0.4329(2) 0.4115(2) 0.0370(8) Uani 1 1 d . . . H26A H 0.2645 0.4110 0.3876 0.056 Uiso 1 1 calc R . . H26B H 0.3469 0.4906 0.3823 0.056 Uiso 1 1 calc R . . H26C H 0.3446 0.4566 0.4636 0.056 Uiso 1 1 calc R . . C27 C 0.5089(2) 0.3695(3) 0.4524(2) 0.0343(8) Uani 1 1 d . . . H27A H 0.5217 0.3854 0.5060 0.051 Uiso 1 1 calc R . . H27B H 0.5235 0.4316 0.4274 0.051 Uiso 1 1 calc R . . H27C H 0.5507 0.3109 0.4487 0.051 Uiso 1 1 calc R . . C28 C 0.2732(2) -0.0394(2) 0.41313(18) 0.0293(7) Uani 1 1 d . . . H28 H 0.2540 -0.0318 0.3568 0.035 Uiso 1 1 calc R . . C29 C 0.1839(3) -0.0773(3) 0.4309(2) 0.0457(9) Uani 1 1 d . . . H29A H 0.2036 -0.0927 0.4853 0.068 Uiso 1 1 calc R . . H29B H 0.1574 -0.1412 0.4016 0.068 Uiso 1 1 calc R . . H29C H 0.1334 -0.0224 0.4171 0.068 Uiso 1 1 calc R . . C30 C 0.3556(3) -0.1208(3) 0.4411(2) 0.0462(10) Uani 1 1 d . . . H30A H 0.4118 -0.0976 0.4281 0.069 Uiso 1 1 calc R . . H30B H 0.3321 -0.1887 0.4168 0.069 Uiso 1 1 calc R . . H30C H 0.3757 -0.1282 0.4964 0.069 Uiso 1 1 calc R . . C31 C 0.3207(3) -0.2685(3) 0.2566(2) 0.0411(9) Uani 1 1 d . . . N1 N 0.16634(17) 0.12499(17) 0.19758(13) 0.0198(5) Uani 1 1 d . . . N2 N 0.30326(17) 0.14827(16) 0.32928(13) 0.0192(5) Uani 1 1 d . . . O1 O 0.17571(19) -0.2936(3) 0.13437(16) 0.0627(8) Uani 1 1 d . . . O2 O 0.3084(2) -0.42031(18) 0.16634(15) 0.0505(7) Uani 1 1 d . . . O3 O 0.3302(2) -0.24490(19) 0.12514(15) 0.0507(7) Uani 1 1 d . . . F1 F 0.2972(2) -0.16770(16) 0.26197(14) 0.0744(8) Uani 1 1 d . . . F2 F 0.4168(2) -0.2741(2) 0.28974(17) 0.0886(9) Uani 1 1 d . . . F3 F 0.2812(2) -0.32403(18) 0.29926(13) 0.0650(7) Uani 1 1 d . . . P1 P 0.19784(5) 0.21017(5) 0.27493(4) 0.02043(18) Uani 1 1 d . . . S1 S 0.27882(7) -0.31267(7) 0.15935(5) 0.0346(2) Uani 1 1 d . . . Br1 Br 0.25086(2) 0.34565(2) 0.221466(18) 0.03070(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0283(17) 0.0222(14) 0.0191(16) 0.0034(12) 0.0097(13) 0.0018(12) C2 0.0273(16) 0.0214(14) 0.0231(16) 0.0023(12) 0.0113(13) 0.0034(12) C3 0.0210(15) 0.0188(14) 0.0262(16) 0.0001(12) 0.0085(13) -0.0014(11) C4 0.0348(18) 0.0275(16) 0.0262(18) -0.0041(13) 0.0044(15) 0.0061(13) C5 0.0350(19) 0.0368(18) 0.0279(18) -0.0030(14) 0.0166(15) 0.0074(14) C6 0.0246(17) 0.0423(19) 0.0288(18) -0.0035(14) 0.0063(14) 0.0056(14) C7 0.0215(15) 0.0231(14) 0.0189(15) -0.0052(12) 0.0040(12) 0.0002(11) C8 0.0324(17) 0.0218(14) 0.0189(15) -0.0041(12) 0.0063(13) 0.0012(12) C9 0.0330(19) 0.0275(16) 0.0241(17) -0.0035(13) 0.0040(14) 0.0021(13) C10 0.0233(17) 0.0313(17) 0.0347(19) -0.0060(14) 0.0012(15) 0.0010(13) C11 0.0261(18) 0.0325(17) 0.037(2) -0.0063(14) 0.0079(15) -0.0052(13) C12 0.0248(16) 0.0233(15) 0.0233(16) -0.0030(12) 0.0061(13) -0.0017(12) C13 0.0322(18) 0.0359(17) 0.0217(17) 0.0042(13) 0.0080(14) 0.0047(13) C14 0.039(2) 0.0371(19) 0.037(2) 0.0125(15) 0.0092(17) 0.0033(15) C15 0.050(2) 0.060(2) 0.0245(19) 0.0043(17) 0.0129(17) 0.0140(18) C16 0.0297(18) 0.0297(16) 0.0259(17) -0.0004(13) 0.0078(14) -0.0058(13) C17 0.053(3) 0.066(3) 0.037(2) 0.0039(19) 0.021(2) 0.007(2) C18 0.057(2) 0.0300(19) 0.042(2) 0.0022(16) 0.0040(19) -0.0113(16) C19 0.0202(15) 0.0235(15) 0.0176(15) -0.0007(11) 0.0044(12) 0.0016(11) C20 0.0209(15) 0.0227(15) 0.0224(16) -0.0019(12) 0.0056(13) 0.0016(11) C21 0.0299(18) 0.0262(16) 0.0287(18) -0.0067(13) 0.0085(14) -0.0003(12) C22 0.0279(17) 0.0411(18) 0.0220(17) -0.0031(14) 0.0093(14) 0.0011(14) C23 0.0286(17) 0.0329(17) 0.0243(17) 0.0055(13) 0.0103(14) -0.0002(13) C24 0.0206(15) 0.0254(15) 0.0247(17) 0.0006(12) 0.0055(13) -0.0002(11) C25 0.0290(17) 0.0223(15) 0.0237(16) -0.0045(12) 0.0066(14) -0.0047(12) C26 0.038(2) 0.0269(17) 0.042(2) 0.0008(15) 0.0083(17) 0.0020(14) C27 0.0346(19) 0.0298(17) 0.038(2) -0.0049(14) 0.0122(16) -0.0078(13) C28 0.0373(19) 0.0251(16) 0.0215(17) 0.0040(12) 0.0056(14) -0.0030(13) C29 0.054(2) 0.043(2) 0.035(2) 0.0036(16) 0.0103(18) -0.0216(17) C30 0.063(3) 0.0288(18) 0.035(2) -0.0018(15) 0.0022(19) 0.0103(17) C31 0.054(2) 0.0305(18) 0.035(2) 0.0008(15) 0.0108(19) 0.0051(16) N1 0.0226(13) 0.0199(12) 0.0157(12) 0.0021(9) 0.0052(10) 0.0010(9) N2 0.0204(12) 0.0201(12) 0.0174(12) 0.0001(9) 0.0069(10) -0.0014(9) O1 0.0340(16) 0.103(2) 0.0471(18) 0.0243(16) 0.0100(13) 0.0099(15) O2 0.075(2) 0.0311(13) 0.0533(18) -0.0082(11) 0.0328(16) -0.0012(12) O3 0.071(2) 0.0421(14) 0.0563(18) 0.0002(12) 0.0445(16) -0.0067(13) F1 0.151(3) 0.0337(12) 0.0538(16) -0.0021(10) 0.0552(18) 0.0113(14) F2 0.0617(18) 0.101(2) 0.073(2) -0.0238(16) -0.0135(15) -0.0065(15) F3 0.113(2) 0.0529(13) 0.0339(13) 0.0053(10) 0.0325(14) -0.0116(14) P1 0.0223(4) 0.0200(4) 0.0184(4) -0.0011(3) 0.0065(3) 0.0007(3) S1 0.0400(5) 0.0369(5) 0.0303(5) 0.0000(4) 0.0167(4) 0.0011(4) Br1 0.0410(2) 0.02254(17) 0.02593(18) 0.00362(12) 0.00857(14) -0.00374(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 C1 N1 1.349(4) . ? C1 C2 1.409(4) . ? C1 C4 1.483(4) . ? C2 C3 1.384(4) . ? C2 C5 1.518(4) . ? C3 N2 1.383(4) . ? C3 C6 1.489(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.407(4) . ? C7 C8 1.412(4) . ? C7 N1 1.473(4) . ? C8 C9 1.401(4) . ? C8 C13 1.525(4) . ? C9 C10 1.372(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.392(4) . ? C11 H11 0.9500 . ? C12 C16 1.518(4) . ? C13 C15 1.536(5) . ? C13 C14 1.538(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.529(5) . ? C16 C18 1.529(4) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.401(4) . ? C19 C20 1.407(4) . ? C19 N2 1.475(4) . ? C20 C21 1.396(4) . ? C20 C25 1.510(4) . ? C21 C22 1.375(5) . ? C21 H21 0.9500 . ? C22 C23 1.387(4) . ? C22 H22 0.9500 . ? C23 C24 1.399(4) . ? C23 H23 0.9500 . ? C24 C28 1.526(4) . ? C25 C27 1.529(4) . ? C25 C26 1.541(4) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.532(5) . ? C28 C30 1.529(4) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 F2 1.317(4) . ? C31 F1 1.339(4) . ? C31 F3 1.341(4) . ? C31 S1 1.802(4) . ? N1 P1 1.740(2) . ? N2 P1 1.706(2) . ? O1 S1 1.427(3) . ? O2 S1 1.426(3) . ? O3 S1 1.435(3) . ? P1 Br1 2.2640(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.3(3) . . ? N1 C1 C4 119.0(3) . . ? C2 C1 C4 119.7(3) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 C5 119.8(3) . . ? C1 C2 C5 117.9(3) . . ? N2 C3 C2 120.7(3) . . ? N2 C3 C6 117.5(3) . . ? C2 C3 C6 121.8(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 122.4(3) . . ? C12 C7 N1 117.6(3) . . ? C8 C7 N1 119.9(3) . . ? C9 C8 C7 116.8(3) . . ? C9 C8 C13 117.4(3) . . ? C7 C8 C13 125.8(3) . . ? C10 C9 C8 121.9(3) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 121.6(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C7 117.3(3) . . ? C11 C12 C16 118.6(3) . . ? C7 C12 C16 124.0(3) . . ? C8 C13 C15 111.8(3) . . ? C8 C13 C14 109.9(3) . . ? C15 C13 C14 109.2(3) . . ? C8 C13 H13 108.6 . . ? C15 C13 H13 108.6 . . ? C14 C13 H13 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 110.5(3) . . ? C12 C16 C18 109.9(3) . . ? C17 C16 C18 111.8(3) . . ? C12 C16 H16 108.2 . . ? C17 C16 H16 108.2 . . ? C18 C16 H16 108.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 122.1(3) . . ? C24 C19 N2 118.7(2) . . ? C20 C19 N2 119.2(2) . . ? C21 C20 C19 117.3(3) . . ? C21 C20 C25 118.7(3) . . ? C19 C20 C25 123.9(3) . . ? C22 C21 C20 121.9(3) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 121.4(3) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C24 C19 117.6(3) . . ? C23 C24 C28 117.8(3) . . ? C19 C24 C28 124.5(3) . . ? C20 C25 C27 112.5(3) . . ? C20 C25 C26 109.3(3) . . ? C27 C25 C26 111.1(2) . . ? C20 C25 H25 108.0 . . ? C27 C25 H25 108.0 . . ? C26 C25 H25 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C24 111.0(3) . . ? C29 C28 C30 109.6(3) . . ? C24 C28 C30 110.0(3) . . ? C29 C28 H28 108.7 . . ? C24 C28 H28 108.7 . . ? C30 C28 H28 108.7 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? F2 C31 F1 105.9(3) . . ? F2 C31 F3 107.3(3) . . ? F1 C31 F3 106.5(3) . . ? F2 C31 S1 112.5(3) . . ? F1 C31 S1 111.8(3) . . ? F3 C31 S1 112.4(3) . . ? C1 N1 C7 122.6(2) . . ? C1 N1 P1 123.8(2) . . ? C7 N1 P1 113.37(18) . . ? C3 N2 C19 121.0(2) . . ? C3 N2 P1 122.5(2) . . ? C19 N2 P1 116.36(18) . . ? N2 P1 N1 97.40(11) . . ? N2 P1 Br1 103.93(9) . . ? N1 P1 Br1 97.59(9) . . ? O1 S1 O2 116.17(18) . . ? O1 S1 O3 113.99(17) . . ? O2 S1 O3 115.40(16) . . ? O1 S1 C31 102.65(18) . . ? O2 S1 C31 102.88(16) . . ? O3 S1 C31 103.08(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 22.3(4) . . . . ? C4 C1 C2 C3 -155.9(3) . . . . ? N1 C1 C2 C5 -166.9(3) . . . . ? C4 C1 C2 C5 14.9(4) . . . . ? C1 C2 C3 N2 -11.8(4) . . . . ? C5 C2 C3 N2 177.6(3) . . . . ? C1 C2 C3 C6 166.0(3) . . . . ? C5 C2 C3 C6 -4.6(4) . . . . ? C12 C7 C8 C9 -1.2(4) . . . . ? N1 C7 C8 C9 -179.4(2) . . . . ? C12 C7 C8 C13 177.5(3) . . . . ? N1 C7 C8 C13 -0.7(4) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? C13 C8 C9 C10 -177.5(3) . . . . ? C8 C9 C10 C11 -0.5(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C10 C11 C12 C16 -177.5(3) . . . . ? C8 C7 C12 C11 0.2(4) . . . . ? N1 C7 C12 C11 178.5(2) . . . . ? C8 C7 C12 C16 178.2(3) . . . . ? N1 C7 C12 C16 -3.5(4) . . . . ? C9 C8 C13 C15 -58.9(4) . . . . ? C7 C8 C13 C15 122.4(3) . . . . ? C9 C8 C13 C14 62.5(4) . . . . ? C7 C8 C13 C14 -116.2(3) . . . . ? C11 C12 C16 C17 -52.7(4) . . . . ? C7 C12 C16 C17 129.4(3) . . . . ? C11 C12 C16 C18 71.1(4) . . . . ? C7 C12 C16 C18 -106.8(3) . . . . ? C24 C19 C20 C21 -3.6(4) . . . . ? N2 C19 C20 C21 177.3(3) . . . . ? C24 C19 C20 C25 175.4(3) . . . . ? N2 C19 C20 C25 -3.7(4) . . . . ? C19 C20 C21 C22 1.2(4) . . . . ? C25 C20 C21 C22 -177.8(3) . . . . ? C20 C21 C22 C23 1.2(5) . . . . ? C21 C22 C23 C24 -1.3(5) . . . . ? C22 C23 C24 C19 -1.0(4) . . . . ? C22 C23 C24 C28 175.2(3) . . . . ? C20 C19 C24 C23 3.6(4) . . . . ? N2 C19 C24 C23 -177.4(3) . . . . ? C20 C19 C24 C28 -172.4(3) . . . . ? N2 C19 C24 C28 6.7(4) . . . . ? C21 C20 C25 C27 53.6(4) . . . . ? C19 C20 C25 C27 -125.4(3) . . . . ? C21 C20 C25 C26 -70.3(3) . . . . ? C19 C20 C25 C26 110.8(3) . . . . ? C23 C24 C28 C29 53.8(4) . . . . ? C19 C24 C28 C29 -130.2(3) . . . . ? C23 C24 C28 C30 -67.7(4) . . . . ? C19 C24 C28 C30 108.3(3) . . . . ? C2 C1 N1 C7 175.4(3) . . . . ? C4 C1 N1 C7 -6.4(4) . . . . ? C2 C1 N1 P1 1.7(4) . . . . ? C4 C1 N1 P1 179.9(2) . . . . ? C12 C7 N1 C1 112.3(3) . . . . ? C8 C7 N1 C1 -69.4(3) . . . . ? C12 C7 N1 P1 -73.4(3) . . . . ? C8 C7 N1 P1 104.9(3) . . . . ? C2 C3 N2 C19 162.6(3) . . . . ? C6 C3 N2 C19 -15.4(4) . . . . ? C2 C3 N2 P1 -22.2(4) . . . . ? C6 C3 N2 P1 159.8(2) . . . . ? C24 C19 N2 C3 -83.0(3) . . . . ? C20 C19 N2 C3 96.1(3) . . . . ? C24 C19 N2 P1 101.5(3) . . . . ? C20 C19 N2 P1 -79.4(3) . . . . ? C3 N2 P1 N1 36.6(2) . . . . ? C19 N2 P1 N1 -148.03(19) . . . . ? C3 N2 P1 Br1 -63.2(2) . . . . ? C19 N2 P1 Br1 112.22(18) . . . . ? C1 N1 P1 N2 -26.6(2) . . . . ? C7 N1 P1 N2 159.20(19) . . . . ? C1 N1 P1 Br1 78.6(2) . . . . ? C7 N1 P1 Br1 -95.60(18) . . . . ? F2 C31 S1 O1 -176.6(3) . . . . ? F1 C31 S1 O1 -57.6(3) . . . . ? F3 C31 S1 O1 62.1(3) . . . . ? F2 C31 S1 O2 62.4(3) . . . . ? F1 C31 S1 O2 -178.6(3) . . . . ? F3 C31 S1 O2 -58.9(3) . . . . ? F2 C31 S1 O3 -57.9(3) . . . . ? F1 C31 S1 O3 61.1(3) . . . . ? F3 C31 S1 O3 -179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.541 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.141 # Attachment 'Lu2.revised.cif' data_try2 _database_code_depnum_ccdc_archive 'CCDC 664931' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H44 N2 O P, C F3 O3 S' _chemical_formula_sum 'C31 H44 F3 N2 O4 P S' _chemical_formula_weight 628.71 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M p_21_21_21 _symmetry_space_group_name_Hall p_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.9393(18) _cell_length_b 12.215(2) _cell_length_c 30.199(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3297.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16044 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5512 _reflns_number_gt 4716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0936P)^2^+0.1427P] 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 SHELXL _refine_ls_extinction_coef 0.038(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(9) _refine_ls_number_reflns 5512 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4151(3) 0.5215(3) 0.11702(10) 0.0377(7) Uani 1 1 d . . . C2 C 0.4282(3) 0.5029(2) 0.16230(10) 0.0349(7) Uani 1 1 d . . . C3 C 0.4918(3) 0.4055(2) 0.17880(9) 0.0309(6) Uani 1 1 d . . . C4 C 0.3241(5) 0.6172(3) 0.10067(12) 0.0696(12) Uani 1 1 d . . . H4A H 0.3267 0.6191 0.0689 0.104 Uiso 1 1 calc R . . H4B H 0.3652 0.6840 0.1122 0.104 Uiso 1 1 calc R . . H4C H 0.2225 0.6095 0.1105 0.104 Uiso 1 1 calc R . . C5 C 0.3655(4) 0.5851(3) 0.19428(10) 0.0443(7) Uani 1 1 d . . . H5A H 0.3824 0.5604 0.2240 0.066 Uiso 1 1 calc R . . H5B H 0.2600 0.5931 0.1893 0.066 Uiso 1 1 calc R . . H5C H 0.4140 0.6544 0.1900 0.066 Uiso 1 1 calc R . . C6 C 0.4692(3) 0.3768(3) 0.22629(9) 0.0404(7) Uani 1 1 d . . . H6A H 0.5197 0.3093 0.2327 0.061 Uiso 1 1 calc R . . H6B H 0.3642 0.3687 0.2321 0.061 Uiso 1 1 calc R . . H6C H 0.5091 0.4340 0.2446 0.061 Uiso 1 1 calc R . . C7 C 0.4452(3) 0.4632(3) 0.03919(10) 0.0428(8) Uani 1 1 d . . . C8 C 0.3315(3) 0.3951(3) 0.02311(11) 0.0488(9) Uani 1 1 d . . . C9 C 0.3005(4) 0.4013(4) -0.02283(12) 0.0594(11) Uani 1 1 d . . . H9 H 0.2254 0.3578 -0.0348 0.071 Uiso 1 1 calc R . . C10 C 0.3792(5) 0.4701(4) -0.04981(12) 0.0662(11) Uani 1 1 d . . . H10 H 0.3587 0.4715 -0.0800 0.079 Uiso 1 1 calc R . . C11 C 0.4888(5) 0.5377(3) -0.03267(12) 0.0618(10) Uani 1 1 d . . . H11 H 0.5403 0.5844 -0.0516 0.074 Uiso 1 1 calc R . . C12 C 0.5241(4) 0.5375(3) 0.01230(10) 0.0491(9) Uani 1 1 d . . . C13 C 0.6463(3) 0.2398(2) 0.16997(8) 0.0281(6) Uani 1 1 d . . . C14 C 0.5874(3) 0.1355(2) 0.15971(9) 0.0354(7) Uani 1 1 d . . . C15 C 0.6687(4) 0.0451(2) 0.17418(10) 0.0407(7) Uani 1 1 d . . . H15 H 0.6330 -0.0247 0.1680 0.049 Uiso 1 1 calc R . . C16 C 0.8003(4) 0.0562(3) 0.19725(10) 0.0428(8) Uani 1 1 d . . . H16 H 0.8529 -0.0058 0.2061 0.051 Uiso 1 1 calc R . . C17 C 0.8540(3) 0.1580(2) 0.20726(10) 0.0379(7) Uani 1 1 d . . . H17 H 0.9422 0.1639 0.2234 0.045 Uiso 1 1 calc R . . C18 C 0.7810(3) 0.2529(2) 0.19400(9) 0.0313(6) Uani 1 1 d . . . C19 C 0.2391(4) 0.3194(3) 0.05189(11) 0.0550(10) Uani 1 1 d . . . H19 H 0.2838 0.3194 0.0815 0.066 Uiso 1 1 calc R . . C20 C 0.0775(4) 0.3609(6) 0.05638(15) 0.1005(19) Uani 1 1 d . . . H20A H 0.0216 0.3116 0.0748 0.151 Uiso 1 1 calc R . . H20B H 0.0320 0.3646 0.0276 0.151 Uiso 1 1 calc R . . H20C H 0.0779 0.4325 0.0695 0.151 Uiso 1 1 calc R . . C21 C 0.2404(5) 0.2021(4) 0.03512(14) 0.0740(12) Uani 1 1 d . . . H21A H 0.3418 0.1769 0.0328 0.111 Uiso 1 1 calc R . . H21B H 0.1937 0.1990 0.0065 0.111 Uiso 1 1 calc R . . H21C H 0.1865 0.1562 0.0554 0.111 Uiso 1 1 calc R . . C22 C 0.6463(5) 0.6130(3) 0.02968(11) 0.0562(9) Uani 1 1 d . . . H22 H 0.6485 0.6062 0.0620 0.067 Uiso 1 1 calc R . . C23 C 0.6138(7) 0.7332(3) 0.01841(14) 0.0923(16) Uani 1 1 d . . . H23A H 0.6928 0.7785 0.0298 0.138 Uiso 1 1 calc R . . H23B H 0.5206 0.7546 0.0316 0.138 Uiso 1 1 calc R . . H23C H 0.6078 0.7416 -0.0131 0.138 Uiso 1 1 calc R . . C24 C 0.7981(4) 0.5794(3) 0.01224(12) 0.0612(10) Uani 1 1 d . . . H24A H 0.8731 0.6281 0.0236 0.092 Uiso 1 1 calc R . . H24B H 0.7977 0.5827 -0.0195 0.092 Uiso 1 1 calc R . . H24C H 0.8198 0.5059 0.0216 0.092 Uiso 1 1 calc R . . C25 C 0.4399(3) 0.1215(3) 0.13624(12) 0.0476(8) Uani 1 1 d . . . H25 H 0.4317 0.1803 0.1143 0.057 Uiso 1 1 calc R . . C26 C 0.4292(5) 0.0113(3) 0.11101(17) 0.0798(14) Uani 1 1 d . . . H26A H 0.3339 0.0064 0.0965 0.120 Uiso 1 1 calc R . . H26B H 0.4394 -0.0481 0.1316 0.120 Uiso 1 1 calc R . . H26C H 0.5076 0.0074 0.0893 0.120 Uiso 1 1 calc R . . C27 C 0.3104(4) 0.1334(4) 0.16784(17) 0.0843(14) Uani 1 1 d . . . H27A H 0.2181 0.1247 0.1520 0.126 Uiso 1 1 calc R . . H27B H 0.3133 0.2047 0.1812 0.126 Uiso 1 1 calc R . . H27C H 0.3173 0.0784 0.1905 0.126 Uiso 1 1 calc R . . C28 C 0.8442(3) 0.3633(2) 0.20683(10) 0.0387(7) Uani 1 1 d . . . H28 H 0.7776 0.4204 0.1954 0.046 Uiso 1 1 calc R . . C29 C 1.0004(4) 0.3804(3) 0.18688(14) 0.0605(10) Uani 1 1 d . . . H29A H 1.0375 0.4511 0.1953 0.091 Uiso 1 1 calc R . . H29B H 0.9944 0.3759 0.1552 0.091 Uiso 1 1 calc R . . H29C H 1.0669 0.3247 0.1977 0.091 Uiso 1 1 calc R . . C30 C 0.8536(4) 0.3751(3) 0.25747(11) 0.0559(9) Uani 1 1 d . . . H30A H 0.8932 0.4459 0.2648 0.084 Uiso 1 1 calc R . . H30B H 0.9179 0.3193 0.2692 0.084 Uiso 1 1 calc R . . H30C H 0.7554 0.3675 0.2700 0.084 Uiso 1 1 calc R . . N1 N 0.4809(3) 0.4553(2) 0.08652(7) 0.0353(6) Uani 1 1 d . . . N2 N 0.5701(2) 0.33715(18) 0.15275(7) 0.0289(5) Uani 1 1 d . . . O1 O 0.7668(2) 0.44237(16) 0.10533(7) 0.0358(5) Uani 1 1 d . . . H1 H 0.7504 0.4843 0.1260 0.054 Uiso 1 1 calc R . . P1 P 0.62650(8) 0.36510(6) 0.09824(2) 0.0316(2) Uani 1 1 d . . . S1 S 0.7521(2) 0.7184(2) 0.16729(9) 0.0385(6) Uani 0.50 1 d P A 1 C31 C 0.925(2) 0.7508(12) 0.1427(4) 0.056(4) Uani 0.50 1 d P A 1 O4 O 0.6462(5) 0.7674(4) 0.1400(2) 0.0664(15) Uani 0.50 1 d P A 1 F3 F 1.0466(4) 0.7113(4) 0.16156(14) 0.0605(11) Uani 0.50 1 d P A 1 S1' S 0.8153(3) 0.6951(2) 0.17402(9) 0.0510(7) Uani 0.50 1 d P A 2 F3' F 0.7767(7) 0.8226(4) 0.10813(17) 0.0889(16) Uani 0.50 1 d P A 2 O4' O 0.9541(8) 0.6437(5) 0.1923(2) 0.091(2) Uani 0.50 1 d P A 2 C31' C 0.8967(17) 0.7700(12) 0.1287(3) 0.045(3) Uani 0.50 1 d P A 2 F1 F 0.9437(3) 0.7136(2) 0.09878(7) 0.0788(7) Uani 1 1 d . . . F2 F 0.9652(3) 0.8562(2) 0.13993(7) 0.0816(8) Uani 1 1 d . . . O3 O 0.7649(3) 0.7657(2) 0.20703(9) 0.0756(9) Uani 1 1 d . . . O2 O 0.7388(4) 0.6074(2) 0.15976(11) 0.0860(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0363(15) 0.0424(18) 0.0346(17) -0.0037(13) -0.0075(13) 0.0180(14) C2 0.0304(14) 0.0400(16) 0.0344(17) -0.0055(13) -0.0019(13) 0.0064(13) C3 0.0248(12) 0.0388(16) 0.0291(15) -0.0078(12) 0.0015(12) -0.0045(12) C4 0.089(3) 0.077(3) 0.0424(19) -0.0037(19) -0.0131(19) 0.053(2) C5 0.0480(17) 0.0463(18) 0.0385(17) -0.0056(14) 0.0035(15) 0.0070(16) C6 0.0455(16) 0.0404(17) 0.0352(16) 0.0031(13) 0.0138(13) 0.0015(15) C7 0.0479(18) 0.0521(19) 0.0283(16) -0.0042(14) -0.0118(14) 0.0166(17) C8 0.0423(16) 0.066(2) 0.0376(18) -0.0050(16) -0.0088(14) 0.0197(17) C9 0.053(2) 0.083(3) 0.042(2) -0.0131(19) -0.0200(17) 0.017(2) C10 0.078(3) 0.087(3) 0.0341(19) -0.0012(19) -0.020(2) 0.026(3) C11 0.083(2) 0.064(2) 0.038(2) 0.0054(17) -0.017(2) 0.015(2) C12 0.066(2) 0.050(2) 0.0312(18) 0.0040(14) -0.0106(16) 0.0188(18) C13 0.0323(13) 0.0297(14) 0.0222(13) 0.0024(11) 0.0060(12) 0.0027(12) C14 0.0426(15) 0.0317(15) 0.0319(15) -0.0043(13) 0.0070(12) -0.0026(14) C15 0.0533(19) 0.0300(15) 0.0387(18) -0.0020(13) 0.0083(15) -0.0014(14) C16 0.0563(19) 0.0334(17) 0.0388(18) 0.0064(14) 0.0042(15) 0.0118(15) C17 0.0395(15) 0.0423(18) 0.0318(15) 0.0018(13) -0.0030(13) 0.0101(14) C18 0.0415(16) 0.0299(15) 0.0226(14) 0.0027(12) 0.0020(12) -0.0004(13) C19 0.0362(17) 0.091(3) 0.0379(19) -0.0154(18) -0.0066(14) 0.0026(19) C20 0.045(2) 0.182(6) 0.075(3) -0.023(4) 0.001(2) 0.018(3) C21 0.070(2) 0.096(3) 0.055(2) -0.022(2) 0.002(2) -0.022(3) C22 0.092(3) 0.047(2) 0.0298(17) 0.0098(14) -0.0145(18) 0.002(2) C23 0.166(5) 0.051(2) 0.060(3) 0.0195(19) -0.035(3) 0.005(3) C24 0.079(3) 0.067(2) 0.037(2) 0.0054(17) -0.0012(18) -0.018(2) C25 0.0494(17) 0.0349(17) 0.059(2) -0.0021(15) -0.0065(16) -0.0052(15) C26 0.081(3) 0.063(3) 0.096(4) -0.027(2) -0.030(3) -0.011(2) C27 0.0420(19) 0.097(3) 0.114(4) -0.019(3) 0.000(2) -0.011(2) C28 0.0431(15) 0.0324(15) 0.0406(16) 0.0021(14) -0.0166(14) -0.0006(15) C29 0.0396(16) 0.058(2) 0.084(3) 0.015(2) -0.0144(19) -0.0074(18) C30 0.068(2) 0.049(2) 0.050(2) -0.0134(17) -0.0274(17) 0.0111(19) N1 0.0382(13) 0.0431(14) 0.0246(13) -0.0037(10) -0.0046(10) 0.0088(12) N2 0.0296(11) 0.0304(12) 0.0266(12) -0.0018(9) -0.0003(9) 0.0017(10) O1 0.0342(10) 0.0401(11) 0.0331(11) 0.0061(9) 0.0060(9) 0.0024(9) P1 0.0381(4) 0.0332(4) 0.0236(4) -0.0013(3) -0.0009(3) 0.0087(3) S1 0.0341(12) 0.0314(12) 0.0499(13) -0.0066(9) -0.0005(10) 0.0045(9) C31 0.118(11) 0.039(6) 0.010(6) 0.003(4) 0.002(6) -0.003(5) O4 0.049(3) 0.044(3) 0.106(4) 0.006(3) -0.021(3) 0.014(2) F3 0.0385(19) 0.086(3) 0.057(3) -0.010(2) 0.006(2) 0.018(2) S1' 0.0724(19) 0.0393(14) 0.0412(12) -0.0072(10) 0.0046(15) -0.0148(14) F3' 0.111(4) 0.083(3) 0.073(3) 0.023(3) -0.027(3) -0.011(3) O4' 0.108(5) 0.061(4) 0.105(5) 0.010(4) -0.051(4) 0.012(4) C31' 0.074(7) 0.051(7) 0.011(6) -0.001(5) 0.017(6) -0.017(6) F1 0.0978(16) 0.0935(17) 0.0451(13) -0.0233(13) 0.0189(12) -0.0117(15) F2 0.1140(18) 0.0694(16) 0.0614(14) -0.0052(12) 0.0169(13) -0.0446(15) O3 0.088(2) 0.0691(18) 0.0696(19) -0.0237(14) 0.0407(16) -0.0163(16) O2 0.106(2) 0.0453(15) 0.107(2) -0.0271(15) 0.042(2) -0.0258(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.360(4) . ? C1 C2 1.391(4) . ? C1 C4 1.507(4) . ? C2 C3 1.410(4) . ? C2 C5 1.501(4) . ? C3 N2 1.344(3) . ? C3 C6 1.490(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.400(5) . ? C7 C12 1.407(5) . ? C7 N1 1.468(4) . ? C8 C9 1.417(5) . ? C8 C19 1.514(5) . ? C9 C10 1.366(6) . ? C9 H9 0.9300 . ? C10 C11 1.382(6) . ? C10 H10 0.9300 . ? C11 C12 1.394(5) . ? C11 H11 0.9300 . ? C12 C22 1.523(5) . ? C13 C14 1.412(4) . ? C13 C18 1.415(4) . ? C13 N2 1.466(3) . ? C14 C15 1.393(4) . ? C14 C25 1.507(4) . ? C15 C16 1.373(5) . ? C15 H15 0.9300 . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C17 C18 1.390(4) . ? C17 H17 0.9300 . ? C18 C28 1.512(4) . ? C19 C21 1.520(6) . ? C19 C20 1.538(5) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C24 1.512(6) . ? C22 C23 1.534(5) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C27 1.507(5) . ? C25 C26 1.549(5) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.535(5) . ? C28 C30 1.538(4) . ? C28 H28 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? N1 P1 1.741(2) . ? N2 P1 1.755(2) . ? O1 P1 1.584(2) . ? O1 H1 0.8200 . ? S1 O3 1.337(4) . ? S1 O2 1.380(4) . ? S1 O4 1.391(5) . ? S1 C31 1.762(19) . ? C31 F3 1.316(17) . ? C31 F2 1.338(16) . ? C31 F1 1.413(13) . ? S1' O2 1.343(4) . ? S1' O3 1.393(4) . ? S1' O4' 1.496(6) . ? S1' C31' 1.800(11) . ? F3' C31' 1.396(15) . ? C31' F1 1.211(14) . ? C31' F2 1.264(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.2(3) . . ? N1 C1 C4 118.2(3) . . ? C2 C1 C4 119.6(3) . . ? C1 C2 C3 121.2(3) . . ? C1 C2 C5 119.5(3) . . ? C3 C2 C5 119.2(3) . . ? N2 C3 C2 121.9(3) . . ? N2 C3 C6 119.2(3) . . ? C2 C3 C6 118.9(2) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 123.1(3) . . ? C8 C7 N1 117.2(3) . . ? C12 C7 N1 119.7(3) . . ? C7 C8 C9 116.7(3) . . ? C7 C8 C19 124.0(3) . . ? C9 C8 C19 119.2(3) . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 121.6(4) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C7 116.7(4) . . ? C11 C12 C22 119.8(3) . . ? C7 C12 C22 123.5(3) . . ? C14 C13 C18 122.2(2) . . ? C14 C13 N2 118.7(2) . . ? C18 C13 N2 119.0(2) . . ? C15 C14 C13 116.8(3) . . ? C15 C14 C25 121.0(3) . . ? C13 C14 C25 122.2(3) . . ? C16 C15 C14 121.9(3) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 122.0(3) . . ? C16 C17 H17 119.0 . . ? C18 C17 H17 119.0 . . ? C17 C18 C13 116.9(3) . . ? C17 C18 C28 119.6(3) . . ? C13 C18 C28 123.4(2) . . ? C8 C19 C21 112.4(3) . . ? C8 C19 C20 111.2(4) . . ? C21 C19 C20 110.3(4) . . ? C8 C19 H19 107.6 . . ? C21 C19 H19 107.6 . . ? C20 C19 H19 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C24 C22 C12 111.0(3) . . ? C24 C22 C23 110.7(4) . . ? C12 C22 C23 111.6(3) . . ? C24 C22 H22 107.8 . . ? C12 C22 H22 107.8 . . ? C23 C22 H22 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C14 C25 C27 111.3(3) . . ? C14 C25 C26 112.6(3) . . ? C27 C25 C26 110.3(3) . . ? C14 C25 H25 107.4 . . ? C27 C25 H25 107.4 . . ? C26 C25 H25 107.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 C29 111.1(3) . . ? C18 C28 C30 111.0(3) . . ? C29 C28 C30 109.1(3) . . ? C18 C28 H28 108.5 . . ? C29 C28 H28 108.5 . . ? C30 C28 H28 108.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 N1 C7 121.7(2) . . ? C1 N1 P1 124.2(2) . . ? C7 N1 P1 113.74(18) . . ? C3 N2 C13 122.6(2) . . ? C3 N2 P1 125.3(2) . . ? C13 N2 P1 110.91(17) . . ? P1 O1 H1 109.5 . . ? O1 P1 N1 104.03(11) . . ? O1 P1 N2 102.51(11) . . ? N1 P1 N2 95.68(11) . . ? O3 S1 O2 125.5(3) . . ? O3 S1 O4 113.8(3) . . ? O2 S1 O4 105.5(3) . . ? O3 S1 C31 101.8(5) . . ? O2 S1 C31 103.1(5) . . ? O4 S1 C31 104.6(5) . . ? F3 C31 F2 99.2(12) . . ? F3 C31 F1 101.1(12) . . ? F2 C31 F1 102.7(8) . . ? F3 C31 S1 117.4(7) . . ? F2 C31 S1 118.5(12) . . ? F1 C31 S1 115.2(11) . . ? O2 S1' O3 124.0(3) . . ? O2 S1' O4' 101.8(3) . . ? O3 S1' O4' 105.3(4) . . ? O2 S1' C31' 111.6(5) . . ? O3 S1' C31' 111.1(5) . . ? O4' S1' C31' 99.2(6) . . ? F1 C31' F2 120.4(11) . . ? F1 C31' F3' 101.4(8) . . ? F2 C31' F3' 96.2(10) . . ? F1 C31' S1' 114.7(10) . . ? F2 C31' S1' 114.5(8) . . ? F3' C31' S1' 105.2(9) . . ? C31' F1 C31 22.5(9) . . ? C31' F2 C31 24.1(7) . . ? S1 O3 S1' 28.08(11) . . ? S1' O2 S1 28.21(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -9.5(5) . . . . ? C4 C1 C2 C3 169.9(3) . . . . ? N1 C1 C2 C5 174.1(3) . . . . ? C4 C1 C2 C5 -6.5(5) . . . . ? C1 C2 C3 N2 14.1(4) . . . . ? C5 C2 C3 N2 -169.5(3) . . . . ? C1 C2 C3 C6 -164.8(3) . . . . ? C5 C2 C3 C6 11.7(4) . . . . ? C12 C7 C8 C9 1.9(5) . . . . ? N1 C7 C8 C9 -178.4(3) . . . . ? C12 C7 C8 C19 -176.3(3) . . . . ? N1 C7 C8 C19 3.4(5) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C19 C8 C9 C10 178.7(3) . . . . ? C8 C9 C10 C11 -1.6(6) . . . . ? C9 C10 C11 C12 0.6(6) . . . . ? C10 C11 C12 C7 1.5(5) . . . . ? C10 C11 C12 C22 179.7(3) . . . . ? C8 C7 C12 C11 -2.8(5) . . . . ? N1 C7 C12 C11 177.5(3) . . . . ? C8 C7 C12 C22 179.0(3) . . . . ? N1 C7 C12 C22 -0.7(5) . . . . ? C18 C13 C14 C15 -0.4(4) . . . . ? N2 C13 C14 C15 175.8(2) . . . . ? C18 C13 C14 C25 176.7(3) . . . . ? N2 C13 C14 C25 -7.2(4) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C25 C14 C15 C16 -177.2(3) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C15 C16 C17 C18 -1.3(5) . . . . ? C16 C17 C18 C13 0.8(4) . . . . ? C16 C17 C18 C28 178.8(3) . . . . ? C14 C13 C18 C17 0.0(4) . . . . ? N2 C13 C18 C17 -176.1(2) . . . . ? C14 C13 C18 C28 -177.8(3) . . . . ? N2 C13 C18 C28 6.0(4) . . . . ? C7 C8 C19 C21 -126.6(4) . . . . ? C9 C8 C19 C21 55.2(4) . . . . ? C7 C8 C19 C20 109.1(4) . . . . ? C9 C8 C19 C20 -69.0(4) . . . . ? C11 C12 C22 C24 -67.2(4) . . . . ? C7 C12 C22 C24 110.9(4) . . . . ? C11 C12 C22 C23 56.7(5) . . . . ? C7 C12 C22 C23 -125.2(4) . . . . ? C15 C14 C25 C27 96.6(4) . . . . ? C13 C14 C25 C27 -80.3(4) . . . . ? C15 C14 C25 C26 -27.9(4) . . . . ? C13 C14 C25 C26 155.2(3) . . . . ? C17 C18 C28 C29 62.1(3) . . . . ? C13 C18 C28 C29 -120.0(3) . . . . ? C17 C18 C28 C30 -59.6(4) . . . . ? C13 C18 C28 C30 118.3(3) . . . . ? C2 C1 N1 C7 168.8(3) . . . . ? C4 C1 N1 C7 -10.5(5) . . . . ? C2 C1 N1 P1 -18.2(4) . . . . ? C4 C1 N1 P1 162.4(3) . . . . ? C8 C7 N1 C1 -92.6(4) . . . . ? C12 C7 N1 C1 87.2(4) . . . . ? C8 C7 N1 P1 93.8(3) . . . . ? C12 C7 N1 P1 -86.5(3) . . . . ? C2 C3 N2 C13 175.4(2) . . . . ? C6 C3 N2 C13 -5.7(4) . . . . ? C2 C3 N2 P1 9.1(4) . . . . ? C6 C3 N2 P1 -172.0(2) . . . . ? C14 C13 N2 C3 108.6(3) . . . . ? C18 C13 N2 C3 -75.1(3) . . . . ? C14 C13 N2 P1 -83.4(3) . . . . ? C18 C13 N2 P1 92.9(2) . . . . ? C1 N1 P1 O1 -72.6(3) . . . . ? C7 N1 P1 O1 100.8(2) . . . . ? C1 N1 P1 N2 31.8(3) . . . . ? C7 N1 P1 N2 -154.7(2) . . . . ? C3 N2 P1 O1 78.2(2) . . . . ? C13 N2 P1 O1 -89.39(18) . . . . ? C3 N2 P1 N1 -27.5(2) . . . . ? C13 N2 P1 N1 164.86(18) . . . . ? O3 S1 C31 F3 63.1(11) . . . . ? O2 S1 C31 F3 -68.1(11) . . . . ? O4 S1 C31 F3 -178.2(9) . . . . ? O3 S1 C31 F2 -56.1(9) . . . . ? O2 S1 C31 F2 172.8(7) . . . . ? O4 S1 C31 F2 62.7(9) . . . . ? O3 S1 C31 F1 -178.1(8) . . . . ? O2 S1 C31 F1 50.7(9) . . . . ? O4 S1 C31 F1 -59.4(10) . . . . ? O2 S1' C31' F1 -37.5(11) . . . . ? O3 S1' C31' F1 179.7(8) . . . . ? O4' S1' C31' F1 69.2(10) . . . . ? O2 S1' C31' F2 177.3(8) . . . . ? O3 S1' C31' F2 34.4(12) . . . . ? O4' S1' C31' F2 -76.0(10) . . . . ? O2 S1' C31' F3' 73.0(9) . . . . ? O3 S1' C31' F3' -69.8(9) . . . . ? O4' S1' C31' F3' 179.7(7) . . . . ? F2 C31' F1 C31 91(4) . . . . ? F3' C31' F1 C31 -165(4) . . . . ? S1' C31' F1 C31 -52(3) . . . . ? F3 C31 F1 C31' -159(4) . . . . ? F2 C31 F1 C31' -57(3) . . . . ? S1 C31 F1 C31' 74(3) . . . . ? F1 C31' F2 C31 -99(4) . . . . ? F3' C31' F2 C31 154(4) . . . . ? S1' C31' F2 C31 44(3) . . . . ? F3 C31 F2 C31' 152(4) . . . . ? F1 C31 F2 C31' 48(2) . . . . ? S1 C31 F2 C31' -80(3) . . . . ? O2 S1 O3 S1' 60.9(4) . . . . ? O4 S1 O3 S1' -166.7(6) . . . . ? C31 S1 O3 S1' -54.8(6) . . . . ? O2 S1' O3 S1 -61.9(5) . . . . ? O4' S1' O3 S1 -178.0(6) . . . . ? C31' S1' O3 S1 75.5(6) . . . . ? O3 S1' O2 S1 58.3(4) . . . . ? O4' S1' O2 S1 176.1(6) . . . . ? C31' S1' O2 S1 -78.9(7) . . . . ? O3 S1 O2 S1' -64.5(5) . . . . ? O4 S1 O2 S1' 160.0(6) . . . . ? C31 S1 O2 S1' 50.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.82 1.82 2.613(3) 162.3 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.502 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.148 # Attachment 'Lu3.cif' data_new _database_code_depnum_ccdc_archive 'CCDC 664932' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H44 N2 O P, Br' _chemical_formula_sum 'C30 H44 Br N2 O P' _chemical_formula_weight 559.55 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pbca _symmetry_space_group_name_Hall -p_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.119(3) _cell_length_b 14.615(3) _cell_length_c 25.530(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6014(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 1.444 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21481 _diffrn_reflns_av_R_equivalents 0.3074 _diffrn_reflns_av_sigmaI/netI 0.3018 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6888 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.1054P)^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 SHELXL _refine_ls_extinction_coef 0.0139(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6888 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2696 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.2915 _refine_ls_wR_factor_gt 0.1908 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C26 C 0.0104(6) 1.4675(6) 0.1109(3) 0.062(3) Uani 1 1 d . . . H26A H 0.0592 1.4643 0.1324 0.093 Uiso 1 1 calc R . . H26B H -0.0347 1.4922 0.1310 0.093 Uiso 1 1 calc R . . H26C H 0.0210 1.5063 0.0813 0.093 Uiso 1 1 calc R . . C27 C -0.0904(5) 1.3737(6) 0.0586(4) 0.061(3) Uani 1 1 d . . . H27A H -0.0813 1.4124 0.0288 0.091 Uiso 1 1 calc R . . H27B H -0.1354 1.3978 0.0791 0.091 Uiso 1 1 calc R . . H27C H -0.1041 1.3131 0.0470 0.091 Uiso 1 1 calc R . . C1 C 0.0185(5) 1.0607(5) 0.1977(3) 0.045(2) Uani 1 1 d . . . C2 C 0.0588(5) 1.1440(5) 0.2060(3) 0.046(2) Uani 1 1 d . . . C3 C 0.0811(5) 1.1998(5) 0.1649(4) 0.045(2) Uani 1 1 d . . . C4 C 0.0124(5) 0.9910(6) 0.2412(3) 0.056(2) Uani 1 1 d . . . H4A H -0.0330 1.0064 0.2638 0.084 Uiso 1 1 calc R . . H4B H 0.0631 0.9908 0.2609 0.084 Uiso 1 1 calc R . . H4C H 0.0034 0.9314 0.2264 0.084 Uiso 1 1 calc R . . C5 C 0.0794(6) 1.1737(6) 0.2625(3) 0.064(3) Uani 1 1 d . . . H5A H 0.1385 1.1728 0.2675 0.096 Uiso 1 1 calc R . . H5B H 0.0537 1.1323 0.2868 0.096 Uiso 1 1 calc R . . H5C H 0.0589 1.2345 0.2684 0.096 Uiso 1 1 calc R . . C6 C 0.1399(6) 1.2799(5) 0.1758(4) 0.061(3) Uani 1 1 d . . . H6A H 0.1632 1.3013 0.1434 0.092 Uiso 1 1 calc R . . H6B H 0.1838 1.2600 0.1985 0.092 Uiso 1 1 calc R . . H6C H 0.1097 1.3287 0.1922 0.092 Uiso 1 1 calc R . . C7 C -0.0572(5) 0.9515(5) 0.1429(3) 0.041(2) Uani 1 1 d . . . C8 C -0.1383(5) 0.9427(5) 0.1628(3) 0.043(2) Uani 1 1 d . . . C9 C -0.1779(6) 0.8586(6) 0.1550(3) 0.056(2) Uani 1 1 d . . . H9 H -0.2307 0.8491 0.1687 0.068 Uiso 1 1 calc R . . C10 C -0.1398(6) 0.7897(6) 0.1273(4) 0.058(3) Uani 1 1 d . . . H10 H -0.1679 0.7352 0.1212 0.070 Uiso 1 1 calc R . . C11 C -0.0599(6) 0.8006(6) 0.1084(4) 0.057(3) Uani 1 1 d . . . H11 H -0.0345 0.7526 0.0907 0.068 Uiso 1 1 calc R . . C12 C -0.0175(5) 0.8812(5) 0.1154(3) 0.044(2) Uani 1 1 d . . . C13 C -0.1854(5) 1.0180(6) 0.1907(3) 0.050(2) Uani 1 1 d . . . H13 H -0.1479 1.0703 0.1949 0.060 Uiso 1 1 calc R . . C14 C -0.2572(5) 1.0479(7) 0.1558(4) 0.062(3) Uani 1 1 d . . . H14A H -0.2366 1.0618 0.1214 0.094 Uiso 1 1 calc R . . H14B H -0.2829 1.1013 0.1704 0.094 Uiso 1 1 calc R . . H14C H -0.2972 0.9994 0.1535 0.094 Uiso 1 1 calc R . . C15 C -0.2178(6) 0.9907(6) 0.2456(3) 0.060(3) Uani 1 1 d . . . H15A H -0.2550 0.9397 0.2423 0.090 Uiso 1 1 calc R . . H15B H -0.2466 1.0415 0.2609 0.090 Uiso 1 1 calc R . . H15C H -0.1719 0.9739 0.2675 0.090 Uiso 1 1 calc R . . C16 C 0.0701(5) 0.8902(6) 0.0938(3) 0.058(2) Uani 1 1 d . . . H16 H 0.0760 0.9530 0.0809 0.070 Uiso 1 1 calc R . . C17 C 0.0867(7) 0.8268(7) 0.0474(4) 0.076(3) Uani 1 1 d . . . H17A H 0.1397 0.8413 0.0323 0.115 Uiso 1 1 calc R . . H17B H 0.0441 0.8349 0.0215 0.115 Uiso 1 1 calc R . . H17C H 0.0868 0.7644 0.0591 0.115 Uiso 1 1 calc R . . C18 C 0.1336(6) 0.8774(8) 0.1352(4) 0.088(4) Uani 1 1 d . . . H18A H 0.1249 0.9214 0.1625 0.132 Uiso 1 1 calc R . . H18B H 0.1878 0.8857 0.1204 0.132 Uiso 1 1 calc R . . H18C H 0.1290 0.8168 0.1494 0.132 Uiso 1 1 calc R . . C19 C 0.0894(5) 1.2396(5) 0.0711(3) 0.0371(19) Uani 1 1 d . . . C20 C 0.0585(6) 1.3274(6) 0.0611(3) 0.049(2) Uani 1 1 d . . . C21 C 0.0940(6) 1.3757(6) 0.0198(3) 0.058(2) Uani 1 1 d . . . H21 H 0.0735 1.4331 0.0110 0.070 Uiso 1 1 calc R . . C22 C 0.1590(7) 1.3395(7) -0.0080(4) 0.065(3) Uani 1 1 d . . . H22 H 0.1833 1.3742 -0.0344 0.078 Uiso 1 1 calc R . . C23 C 0.1893(6) 1.2531(6) 0.0020(4) 0.060(3) Uani 1 1 d . . . H23 H 0.2332 1.2301 -0.0176 0.071 Uiso 1 1 calc R . . C24 C 0.1542(6) 1.2002(6) 0.0416(4) 0.055(3) Uani 1 1 d . . . C25 C -0.0125(5) 1.3706(5) 0.0917(3) 0.048(2) Uani 1 1 d . . . H25 H -0.0236 1.3323 0.1224 0.057 Uiso 1 1 calc R . . C28 C 0.1874(6) 1.1036(6) 0.0528(4) 0.064(3) Uani 1 1 d . . . H28 H 0.1502 1.0748 0.0783 0.077 Uiso 1 1 calc R . . C29 C 0.1860(7) 1.0451(7) 0.0025(4) 0.088(4) Uani 1 1 d . . . H29A H 0.1298 1.0386 -0.0095 0.132 Uiso 1 1 calc R . . H29B H 0.2088 0.9858 0.0098 0.132 Uiso 1 1 calc R . . H29C H 0.2184 1.0746 -0.0242 0.132 Uiso 1 1 calc R . . C30 C 0.2763(6) 1.1069(8) 0.0774(5) 0.101(4) Uani 1 1 d . . . H30A H 0.3139 1.1356 0.0533 0.152 Uiso 1 1 calc R . . H30B H 0.2949 1.0458 0.0846 0.152 Uiso 1 1 calc R . . H30C H 0.2747 1.1414 0.1094 0.152 Uiso 1 1 calc R . . N1 N -0.0144(4) 1.0385(4) 0.1503(2) 0.0374(16) Uani 1 1 d . . . N2 N 0.0556(4) 1.1860(4) 0.1153(3) 0.0422(17) Uani 1 1 d . . . O1 O -0.1053(3) 1.1717(3) 0.1120(2) 0.0461(14) Uani 1 1 d . . . H1 H -0.1472 1.1426 0.1047 0.069 Uiso 1 1 calc R . . P1 P -0.02586(13) 1.11336(14) 0.09733(8) 0.0389(6) Uani 1 1 d . . . Br1 Br 0.12489(6) 0.77098(6) 0.28282(4) 0.0675(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C26 0.089(7) 0.041(5) 0.056(6) 0.002(4) -0.001(5) 0.007(5) C27 0.062(6) 0.044(5) 0.077(7) 0.008(5) -0.010(5) 0.002(5) C1 0.040(5) 0.036(5) 0.060(6) 0.007(4) 0.009(4) 0.006(4) C2 0.049(5) 0.038(5) 0.050(6) 0.000(4) -0.009(4) 0.009(4) C3 0.032(5) 0.039(5) 0.065(7) -0.006(5) 0.002(4) 0.006(4) C4 0.067(6) 0.047(5) 0.055(6) 0.012(5) -0.014(5) -0.002(5) C5 0.079(7) 0.055(6) 0.058(6) -0.004(5) -0.016(5) 0.010(5) C6 0.070(7) 0.047(6) 0.067(7) 0.004(5) -0.013(5) -0.011(5) C7 0.051(5) 0.036(5) 0.036(5) 0.012(4) -0.008(4) -0.003(4) C8 0.038(5) 0.040(5) 0.050(5) 0.009(4) 0.000(4) 0.002(4) C9 0.061(6) 0.062(6) 0.046(6) 0.012(5) -0.001(5) -0.013(5) C10 0.081(8) 0.036(5) 0.057(6) 0.002(4) -0.007(6) -0.018(5) C11 0.072(7) 0.039(5) 0.058(6) 0.004(4) 0.003(5) 0.007(5) C12 0.061(6) 0.029(5) 0.041(5) 0.002(4) -0.005(4) 0.001(4) C13 0.037(5) 0.056(6) 0.056(6) 0.013(5) 0.005(4) 0.009(4) C14 0.036(5) 0.084(7) 0.068(7) 0.013(5) 0.004(5) 0.015(5) C15 0.068(6) 0.062(6) 0.050(6) 0.010(5) 0.014(5) 0.009(5) C16 0.051(6) 0.055(6) 0.069(7) 0.000(5) 0.016(5) 0.009(5) C17 0.079(7) 0.078(7) 0.073(7) -0.008(6) 0.015(6) 0.022(6) C18 0.059(7) 0.119(10) 0.085(8) -0.012(7) 0.005(6) 0.028(7) C19 0.042(5) 0.038(5) 0.032(5) 0.002(4) 0.002(4) -0.011(4) C20 0.077(6) 0.039(5) 0.031(5) -0.005(4) -0.005(5) -0.014(5) C21 0.075(7) 0.044(5) 0.056(6) 0.014(5) -0.008(6) -0.012(5) C22 0.079(7) 0.062(7) 0.053(6) 0.008(5) -0.004(6) -0.034(6) C23 0.065(6) 0.062(6) 0.052(6) -0.008(5) 0.017(5) -0.033(5) C24 0.053(6) 0.056(6) 0.057(6) -0.009(5) 0.008(5) -0.015(5) C25 0.067(6) 0.039(5) 0.037(5) 0.001(4) -0.008(4) 0.002(4) C28 0.060(6) 0.051(6) 0.081(7) 0.004(5) 0.020(5) -0.001(5) C29 0.096(9) 0.070(7) 0.099(9) -0.019(7) 0.039(7) 0.009(6) C30 0.046(7) 0.090(9) 0.168(12) -0.001(8) -0.007(7) 0.009(6) N1 0.040(4) 0.031(3) 0.041(4) 0.004(3) -0.003(3) 0.000(3) N2 0.051(4) 0.037(4) 0.039(4) -0.003(3) 0.000(3) -0.005(3) O1 0.039(3) 0.040(3) 0.059(4) 0.006(3) -0.010(3) -0.008(3) P1 0.0447(13) 0.0320(11) 0.0399(13) 0.0028(10) -0.0038(10) -0.0035(10) Br1 0.0668(7) 0.0588(7) 0.0770(8) 0.0178(5) -0.0160(6) -0.0199(5) _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 C26 C25 1.545(11) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C25 1.514(11) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C1 N1 1.361(10) . ? C1 C2 1.397(11) . ? C1 C4 1.510(11) . ? C2 C3 1.379(11) . ? C2 C5 1.542(11) . ? C3 N2 1.345(10) . ? C3 C6 1.532(12) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.399(11) . ? C7 C8 1.409(10) . ? C7 N1 1.459(10) . ? C8 C9 1.399(11) . ? C8 C13 1.515(11) . ? C9 C10 1.376(12) . ? C9 H9 0.9300 . ? C10 C11 1.384(13) . ? C10 H10 0.9300 . ? C11 C12 1.374(11) . ? C11 H11 0.9300 . ? C12 C16 1.522(11) . ? C13 C14 1.525(11) . ? C13 C15 1.547(11) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C18 1.482(12) . ? C16 C17 1.528(12) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.400(11) . ? C19 C24 1.411(12) . ? C19 N2 1.479(10) . ? C20 C21 1.391(11) . ? C20 C25 1.523(12) . ? C21 C22 1.372(13) . ? C21 H21 0.9300 . ? C22 C23 1.377(13) . ? C22 H22 0.9300 . ? C23 C24 1.392(12) . ? C23 H23 0.9300 . ? C24 C28 1.537(12) . ? C25 H25 0.9800 . ? C28 C29 1.543(13) . ? C28 C30 1.566(13) . ? C28 H28 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? N1 P1 1.749(6) . ? N2 P1 1.750(7) . ? O1 P1 1.583(6) . ? O1 H1 0.8200 . ? 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 C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N1 C1 C2 121.6(7) . . ? N1 C1 C4 117.9(7) . . ? C2 C1 C4 120.4(8) . . ? C3 C2 C1 121.4(8) . . ? C3 C2 C5 119.3(8) . . ? C1 C2 C5 119.2(8) . . ? N2 C3 C2 123.3(8) . . ? N2 C3 C6 118.3(8) . . ? C2 C3 C6 118.4(8) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 122.5(7) . . ? C12 C7 N1 119.3(7) . . ? C8 C7 N1 118.2(7) . . ? C9 C8 C7 116.9(8) . . ? C9 C8 C13 118.5(7) . . ? C7 C8 C13 124.6(7) . . ? C10 C9 C8 120.8(8) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.7(8) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 121.1(9) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C7 117.9(8) . . ? C11 C12 C16 119.2(8) . . ? C7 C12 C16 122.9(7) . . ? C8 C13 C14 108.3(7) . . ? C8 C13 C15 114.0(7) . . ? C14 C13 C15 110.3(7) . . ? C8 C13 H13 108.0 . . ? C14 C13 H13 108.0 . . ? C15 C13 H13 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C12 111.7(7) . . ? C18 C16 C17 110.9(8) . . ? C12 C16 C17 113.1(8) . . ? C18 C16 H16 106.9 . . ? C12 C16 H16 106.9 . . ? C17 C16 H16 106.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 122.7(8) . . ? C20 C19 N2 119.6(7) . . ? C24 C19 N2 117.6(7) . . ? C19 C20 C21 117.1(8) . . ? C19 C20 C25 123.6(7) . . ? C21 C20 C25 119.2(8) . . ? C22 C21 C20 120.7(8) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 121.8(9) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C22 C23 C24 120.0(9) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 117.4(9) . . ? C23 C24 C28 120.3(9) . . ? C19 C24 C28 122.3(8) . . ? C20 C25 C27 110.5(7) . . ? C20 C25 C26 111.3(7) . . ? C27 C25 C26 110.4(7) . . ? C20 C25 H25 108.2 . . ? C27 C25 H25 108.2 . . ? C26 C25 H25 108.2 . . ? C24 C28 C29 110.4(8) . . ? C24 C28 C30 111.4(8) . . ? C29 C28 C30 111.4(8) . . ? C24 C28 H28 107.8 . . ? C29 C28 H28 107.8 . . ? C30 C28 H28 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 N1 C7 120.4(6) . . ? C1 N1 P1 125.5(5) . . ? C7 N1 P1 113.3(5) . . ? C3 N2 C19 121.7(7) . . ? C3 N2 P1 124.6(6) . . ? C19 N2 P1 113.4(5) . . ? P1 O1 H1 109.5 . . ? O1 P1 N2 102.6(3) . . ? O1 P1 N1 103.9(3) . . ? N2 P1 N1 95.6(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 N1 C1 C2 C3 -12.5(12) . . . . ? C4 C1 C2 C3 165.6(7) . . . . ? N1 C1 C2 C5 168.0(7) . . . . ? C4 C1 C2 C5 -13.9(11) . . . . ? C1 C2 C3 N2 10.2(12) . . . . ? C5 C2 C3 N2 -170.3(8) . . . . ? C1 C2 C3 C6 -168.0(8) . . . . ? C5 C2 C3 C6 11.5(11) . . . . ? C12 C7 C8 C9 1.4(11) . . . . ? N1 C7 C8 C9 179.8(7) . . . . ? C12 C7 C8 C13 -177.2(7) . . . . ? N1 C7 C8 C13 1.1(11) . . . . ? C7 C8 C9 C10 -2.4(12) . . . . ? C13 C8 C9 C10 176.3(8) . . . . ? C8 C9 C10 C11 2.7(14) . . . . ? C9 C10 C11 C12 -1.9(14) . . . . ? C10 C11 C12 C7 0.8(13) . . . . ? C10 C11 C12 C16 -179.8(8) . . . . ? C8 C7 C12 C11 -0.6(11) . . . . ? N1 C7 C12 C11 -179.0(7) . . . . ? C8 C7 C12 C16 180.0(7) . . . . ? N1 C7 C12 C16 1.6(11) . . . . ? C9 C8 C13 C14 -66.9(10) . . . . ? C7 C8 C13 C14 111.7(8) . . . . ? C9 C8 C13 C15 56.3(10) . . . . ? C7 C8 C13 C15 -125.1(8) . . . . ? C11 C12 C16 C18 -100.5(10) . . . . ? C7 C12 C16 C18 78.9(11) . . . . ? C11 C12 C16 C17 25.4(11) . . . . ? C7 C12 C16 C17 -155.2(8) . . . . ? C24 C19 C20 C21 0.5(12) . . . . ? N2 C19 C20 C21 178.4(7) . . . . ? C24 C19 C20 C25 178.7(8) . . . . ? N2 C19 C20 C25 -3.4(12) . . . . ? C19 C20 C21 C22 -2.8(13) . . . . ? C25 C20 C21 C22 178.9(8) . . . . ? C20 C21 C22 C23 2.8(14) . . . . ? C21 C22 C23 C24 -0.4(14) . . . . ? C22 C23 C24 C19 -1.8(13) . . . . ? C22 C23 C24 C28 179.7(9) . . . . ? C20 C19 C24 C23 1.8(13) . . . . ? N2 C19 C24 C23 -176.2(8) . . . . ? C20 C19 C24 C28 -179.7(8) . . . . ? N2 C19 C24 C28 2.3(12) . . . . ? C19 C20 C25 C27 -107.3(9) . . . . ? C21 C20 C25 C27 71.0(10) . . . . ? C19 C20 C25 C26 129.8(8) . . . . ? C21 C20 C25 C26 -52.0(10) . . . . ? C23 C24 C28 C29 -54.8(12) . . . . ? C19 C24 C28 C29 126.7(9) . . . . ? C23 C24 C28 C30 69.5(12) . . . . ? C19 C24 C28 C30 -108.9(10) . . . . ? C2 C1 N1 C7 -179.2(7) . . . . ? C4 C1 N1 C7 2.7(11) . . . . ? C2 C1 N1 P1 -10.3(11) . . . . ? C4 C1 N1 P1 171.6(6) . . . . ? C12 C7 N1 C1 -105.0(9) . . . . ? C8 C7 N1 C1 76.5(9) . . . . ? C12 C7 N1 P1 84.8(7) . . . . ? C8 C7 N1 P1 -93.6(7) . . . . ? C2 C3 N2 C19 -171.8(7) . . . . ? C6 C3 N2 C19 6.4(11) . . . . ? C2 C3 N2 P1 14.8(11) . . . . ? C6 C3 N2 P1 -167.0(6) . . . . ? C20 C19 N2 C3 -80.9(10) . . . . ? C24 C19 N2 C3 97.1(9) . . . . ? C20 C19 N2 P1 93.2(8) . . . . ? C24 C19 N2 P1 -88.8(8) . . . . ? C3 N2 P1 O1 77.1(7) . . . . ? C19 N2 P1 O1 -96.8(5) . . . . ? C3 N2 P1 N1 -28.5(7) . . . . ? C19 N2 P1 N1 157.6(5) . . . . ? C1 N1 P1 O1 -78.1(7) . . . . ? C7 N1 P1 O1 91.5(5) . . . . ? C1 N1 P1 N2 26.4(7) . . . . ? C7 N1 P1 N2 -164.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.205 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.257