# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'K. C. Kumara Swamy' _publ_contact_author_address ; School of Chemistry University of Hyderabad Gachibowli Hyderabad A.P. 500046 INDIA ; _publ_contact_author_email KCKSSC@UOHYD.ERNET.IN _publ_section_title ; Structurally Diverse Penta- and Hexa-coordinate Phosphorus Compounds from the Reaction of Diethyl- or Diisopropyl- Azodicarboxylates with Phosphorus(III) Compounds ; loop_ _publ_author_name 'K. C. Kumara Swamy' 'K. V. P. Pavan Kumar' 'N. Satish Kumar' # Attachment 'B514839A_cif.txt' data_compd12a _database_code_depnum_ccdc_archive 'CCDC 280917' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H43 N4 O6 P' _chemical_formula_weight 610.67 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 P_21/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 9.4608(12) _cell_length_b 17.042(2) _cell_length_c 20.513(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.124(2) _cell_angle_gamma 90.00 _cell_volume 3274.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NEEDLES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type 'EMPIRICAL, SADABS' _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31071 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5771 _reflns_number_gt 4227 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0941P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5771 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 P P 0.44958(5) 0.38324(3) 0.20759(3) 0.03697(17) Uani 1 1 d . . . O2 O 0.49185(14) 0.37617(8) 0.28542(6) 0.0412(3) Uani 1 1 d . . . O3 O 0.62132(14) 0.41040(8) 0.19795(7) 0.0407(3) Uani 1 1 d . . . O1 O 0.45570(14) 0.30544(7) 0.16611(7) 0.0410(3) Uani 1 1 d . . . N3 N 0.27254(18) 0.36134(10) 0.21894(9) 0.0473(4) Uani 1 1 d . . . O6 O 0.19329(16) 0.43594(9) 0.10633(8) 0.0552(4) Uani 1 1 d . . . C1 C 0.5750(2) 0.26047(11) 0.15295(10) 0.0402(5) Uani 1 1 d . . . N2 N 0.51128(19) 0.52137(10) 0.15860(9) 0.0485(5) Uani 1 1 d . . . C13 C 0.6283(2) 0.36322(12) 0.32157(9) 0.0379(5) Uani 1 1 d . . . C27 C 0.6251(2) 0.48310(12) 0.17546(10) 0.0431(5) Uani 1 1 d . . . N1 N 0.39983(17) 0.46785(9) 0.16927(8) 0.0419(4) Uani 1 1 d . . . C6 C 0.6467(2) 0.21877(11) 0.20585(10) 0.0421(5) Uani 1 1 d . . . C12 C 0.6896(2) 0.42000(12) 0.36587(10) 0.0426(5) Uani 1 1 d . . . O5 O 0.22562(18) 0.56058(9) 0.13938(10) 0.0741(5) Uani 1 1 d . . . C7 C 0.6085(2) 0.22504(11) 0.27456(10) 0.0455(5) Uani 1 1 d . . . H7A H 0.6286 0.1752 0.2968 0.055 Uiso 1 1 calc R . . H7B H 0.5067 0.2346 0.2716 0.055 Uiso 1 1 calc R . . C11 C 0.8238(2) 0.40127(13) 0.39875(10) 0.0504(5) Uani 1 1 d . . . H11 H 0.8706 0.4384 0.4273 0.060 Uiso 1 1 calc R . . C2 C 0.6031(2) 0.25281(12) 0.08828(11) 0.0467(5) Uani 1 1 d . . . N4 N 0.1998(2) 0.41640(13) 0.24942(10) 0.0609(5) Uani 1 1 d . . . O4 O 0.75614(16) 0.50968(9) 0.17405(8) 0.0620(5) Uani 1 1 d . . . C9 C 0.8206(2) 0.27461(13) 0.35111(10) 0.0479(5) Uani 1 1 d . . . H9 H 0.8626 0.2258 0.3475 0.057 Uiso 1 1 calc R . . C8 C 0.6878(2) 0.28948(11) 0.31577(9) 0.0399(5) Uani 1 1 d . . . C14 C 0.5198(3) 0.29435(13) 0.02831(11) 0.0528(6) Uani 1 1 d . . . C20 C 0.6136(3) 0.49605(13) 0.38182(11) 0.0527(6) Uani 1 1 d . . . C10 C 0.8921(2) 0.33075(14) 0.39158(11) 0.0528(6) Uani 1 1 d . . . C3 C 0.7149(3) 0.20153(14) 0.08013(12) 0.0585(6) Uani 1 1 d . . . H3 H 0.7403 0.1959 0.0382 0.070 Uiso 1 1 calc R . . C24 C 0.2643(2) 0.49449(13) 0.13915(11) 0.0492(5) Uani 1 1 d . . . C32 C 0.0731(3) 0.38434(18) 0.25160(15) 0.0733(8) Uani 1 1 d . . . H32 H -0.0002 0.4087 0.2698 0.088 Uiso 1 1 calc R . . C5 C 0.7535(2) 0.16792(12) 0.19313(12) 0.0528(6) Uani 1 1 d . . . H5 H 0.8023 0.1390 0.2277 0.063 Uiso 1 1 calc R . . C15 C 0.5361(3) 0.38346(14) 0.03407(13) 0.0660(7) Uani 1 1 d . . . H15A H 0.5010 0.4073 -0.0075 0.099 Uiso 1 1 calc R . . H15B H 0.6350 0.3965 0.0461 0.099 Uiso 1 1 calc R . . H15C H 0.4824 0.4025 0.0672 0.099 Uiso 1 1 calc R . . C4 C 0.7896(3) 0.15879(14) 0.13110(13) 0.0602(6) Uani 1 1 d . . . C22 C 0.4684(3) 0.47727(18) 0.40236(15) 0.0815(8) Uani 1 1 d . . . H22A H 0.4800 0.4388 0.4369 0.122 Uiso 1 1 calc R . . H22B H 0.4059 0.4571 0.3652 0.122 Uiso 1 1 calc R . . H22C H 0.4280 0.5242 0.4179 0.122 Uiso 1 1 calc R . . C30 C 0.1905(3) 0.29714(15) 0.20383(14) 0.0638(7) Uani 1 1 d . . . H30 H 0.2171 0.2518 0.1834 0.077 Uiso 1 1 calc R . . C23 C 0.7003(3) 0.54054(16) 0.43917(14) 0.0803(9) Uani 1 1 d . . . H23A H 0.7914 0.5549 0.4273 0.121 Uiso 1 1 calc R . . H23B H 0.7142 0.5075 0.4774 0.121 Uiso 1 1 calc R . . H23C H 0.6495 0.5870 0.4486 0.121 Uiso 1 1 calc R . . C31 C 0.0626(3) 0.31091(19) 0.22383(16) 0.0803(9) Uani 1 1 d . . . H31 H -0.0160 0.2776 0.2197 0.096 Uiso 1 1 calc R . . C28 C 0.7641(4) 0.59105(19) 0.1523(2) 0.1145(14) Uani 1 1 d . . . H28A H 0.7643 0.5920 0.1050 0.137 Uiso 1 1 calc R . . H28B H 0.6801 0.6191 0.1617 0.137 Uiso 1 1 calc R . . C16 C 0.3608(3) 0.27321(16) 0.02177(14) 0.0732(8) Uani 1 1 d . . . H16A H 0.3494 0.2176 0.0156 0.110 Uiso 1 1 calc R . . H16B H 0.3098 0.3002 -0.0154 0.110 Uiso 1 1 calc R . . H16C H 0.3236 0.2886 0.0610 0.110 Uiso 1 1 calc R . . C21 C 0.5937(4) 0.55164(16) 0.32225(14) 0.0847(9) Uani 1 1 d . . . H21A H 0.5590 0.6014 0.3352 0.127 Uiso 1 1 calc R . . H21B H 0.5261 0.5294 0.2879 0.127 Uiso 1 1 calc R . . H21C H 0.6836 0.5589 0.3064 0.127 Uiso 1 1 calc R . . C18 C 0.9067(3) 0.1025(2) 0.11776(17) 0.0963(11) Uani 1 1 d . . . H18A H 0.9962 0.1299 0.1221 0.144 Uiso 1 1 calc R . . H18B H 0.8849 0.0820 0.0739 0.144 Uiso 1 1 calc R . . H18C H 0.9129 0.0602 0.1489 0.144 Uiso 1 1 calc R . . C29 C 0.8807(7) 0.6274(3) 0.1819(3) 0.197(3) Uani 1 1 d . . . H29A H 0.9025 0.6090 0.2264 0.295 Uiso 1 1 calc R . . H29B H 0.8640 0.6830 0.1820 0.295 Uiso 1 1 calc R . . H29C H 0.9596 0.6164 0.1585 0.295 Uiso 1 1 calc R . . C25 C 0.0442(3) 0.44981(17) 0.08287(15) 0.0776(8) Uani 1 1 d . . . H25A H 0.0332 0.4966 0.0557 0.093 Uiso 1 1 calc R . . H25B H -0.0084 0.4571 0.1197 0.093 Uiso 1 1 calc R . . C19 C 1.0397(3) 0.31564(19) 0.42879(16) 0.0861(9) Uani 1 1 d . . . H19A H 1.0457 0.2624 0.4442 0.129 Uiso 1 1 calc R . . H19B H 1.0570 0.3507 0.4657 0.129 Uiso 1 1 calc R . . H19C H 1.1100 0.3243 0.4001 0.129 Uiso 1 1 calc R . . C26 C -0.0106(3) 0.37971(19) 0.04361(19) 0.1033(12) Uani 1 1 d . . . H26A H 0.0385 0.3748 0.0059 0.155 Uiso 1 1 calc R . . H26B H -0.1111 0.3857 0.0293 0.155 Uiso 1 1 calc R . . H26C H 0.0055 0.3335 0.0704 0.155 Uiso 1 1 calc R . . C17 C 0.5751(4) 0.2716(2) -0.03610(14) 0.0943(10) Uani 1 1 d . . . H17A H 0.5580 0.2168 -0.0447 0.141 Uiso 1 1 calc R . . H17B H 0.6757 0.2820 -0.0320 0.141 Uiso 1 1 calc R . . H17C H 0.5261 0.3020 -0.0718 0.141 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 P 0.0343(3) 0.0354(3) 0.0412(3) 0.0024(2) 0.0052(2) 0.0011(2) O2 0.0371(7) 0.0452(8) 0.0413(8) 0.0035(6) 0.0060(6) 0.0049(6) O3 0.0380(8) 0.0381(8) 0.0463(8) 0.0038(6) 0.0070(6) -0.0016(6) O1 0.0375(7) 0.0374(7) 0.0479(8) -0.0013(6) 0.0050(6) -0.0007(6) N3 0.0394(10) 0.0507(11) 0.0523(11) 0.0045(8) 0.0081(8) 0.0011(8) O6 0.0493(9) 0.0513(9) 0.0604(10) -0.0030(7) -0.0078(7) 0.0030(7) C1 0.0363(10) 0.0321(10) 0.0519(13) -0.0045(9) 0.0054(9) -0.0021(8) N2 0.0491(11) 0.0388(10) 0.0565(11) 0.0063(8) 0.0034(9) -0.0038(8) C13 0.0357(10) 0.0424(11) 0.0362(11) 0.0066(8) 0.0071(8) 0.0043(8) C27 0.0462(12) 0.0377(11) 0.0452(12) 0.0005(9) 0.0057(9) -0.0063(9) N1 0.0381(9) 0.0373(9) 0.0492(10) 0.0040(7) 0.0023(8) -0.0001(7) C6 0.0409(11) 0.0312(10) 0.0530(13) -0.0054(9) 0.0025(9) -0.0063(8) C12 0.0473(12) 0.0453(12) 0.0362(11) 0.0020(9) 0.0099(9) 0.0028(9) O5 0.0660(11) 0.0447(10) 0.1037(15) -0.0021(9) -0.0159(10) 0.0138(8) C7 0.0488(12) 0.0325(11) 0.0547(13) 0.0085(9) 0.0061(10) 0.0012(9) C11 0.0526(13) 0.0550(14) 0.0415(12) -0.0031(10) -0.0008(10) 0.0016(11) C2 0.0471(12) 0.0434(12) 0.0488(13) -0.0108(10) 0.0038(10) -0.0030(10) N4 0.0439(11) 0.0734(13) 0.0679(13) -0.0014(11) 0.0171(10) 0.0072(10) O4 0.0488(9) 0.0533(10) 0.0832(12) 0.0136(8) 0.0066(8) -0.0151(7) C9 0.0508(13) 0.0473(12) 0.0458(12) 0.0057(10) 0.0073(10) 0.0130(10) C8 0.0450(11) 0.0390(11) 0.0368(11) 0.0064(8) 0.0093(9) 0.0024(9) C14 0.0602(14) 0.0536(14) 0.0441(13) -0.0074(10) 0.0058(11) 0.0037(11) C20 0.0663(15) 0.0474(13) 0.0446(12) -0.0057(10) 0.0083(11) 0.0101(11) C10 0.0496(13) 0.0617(15) 0.0451(13) 0.0008(11) -0.0007(10) 0.0095(11) C3 0.0540(14) 0.0669(16) 0.0547(14) -0.0171(12) 0.0082(11) 0.0035(12) C24 0.0499(12) 0.0402(13) 0.0553(14) 0.0001(10) -0.0003(10) 0.0055(10) C32 0.0459(15) 0.096(2) 0.082(2) 0.0112(16) 0.0238(13) 0.0061(14) C5 0.0465(13) 0.0414(12) 0.0666(16) -0.0079(11) -0.0055(11) 0.0056(10) C15 0.0824(18) 0.0607(16) 0.0546(15) 0.0051(12) 0.0084(13) -0.0055(13) C4 0.0470(13) 0.0610(15) 0.0708(17) -0.0210(13) 0.0018(12) 0.0114(11) C22 0.0727(18) 0.090(2) 0.086(2) -0.0230(16) 0.0267(16) 0.0161(16) C30 0.0496(14) 0.0563(15) 0.0861(19) 0.0073(13) 0.0115(13) -0.0138(12) C23 0.096(2) 0.0691(18) 0.0728(18) -0.0291(14) 0.0021(16) 0.0114(16) C31 0.0471(15) 0.092(2) 0.105(2) 0.0157(18) 0.0207(15) -0.0180(14) C28 0.078(2) 0.086(2) 0.170(4) 0.067(2) -0.014(2) -0.0361(18) C16 0.0697(18) 0.0724(18) 0.0693(17) 0.0027(14) -0.0187(14) -0.0093(14) C21 0.131(3) 0.0524(16) 0.0696(18) 0.0021(13) 0.0112(18) 0.0313(16) C18 0.076(2) 0.119(3) 0.092(2) -0.030(2) 0.0031(17) 0.0461(19) C29 0.269(7) 0.098(3) 0.209(6) 0.007(3) -0.014(5) -0.100(4) C25 0.0520(15) 0.087(2) 0.085(2) 0.0043(16) -0.0185(14) 0.0055(14) C19 0.0672(18) 0.094(2) 0.086(2) -0.0085(17) -0.0279(15) 0.0231(16) C26 0.076(2) 0.097(2) 0.123(3) -0.005(2) -0.034(2) -0.0167(18) C17 0.126(3) 0.107(2) 0.0498(16) -0.0108(16) 0.0115(16) 0.037(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O1 1.5809(14) . ? P O2 1.5948(14) . ? P N1 1.6775(17) . ? P O3 1.7274(14) . ? P N3 1.7633(18) . ? O2 C13 1.412(2) . ? O3 C27 1.324(2) . ? O1 C1 1.421(2) . ? N3 C30 1.352(3) . ? N3 N4 1.366(3) . ? O6 C24 1.331(3) . ? O6 C25 1.444(3) . ? C1 C6 1.391(3) . ? C1 C2 1.396(3) . ? N2 C27 1.264(3) . ? N2 N1 1.434(2) . ? C13 C8 1.389(3) . ? C13 C12 1.396(3) . ? C27 O4 1.324(2) . ? N1 C24 1.417(3) . ? C6 C5 1.384(3) . ? C6 C7 1.508(3) . ? C12 C11 1.389(3) . ? C12 C20 1.539(3) . ? O5 C24 1.184(2) . ? C7 C8 1.518(3) . ? C11 C10 1.382(3) . ? C2 C3 1.400(3) . ? C2 C14 1.537(3) . ? N4 C32 1.324(3) . ? O4 C28 1.462(3) . ? C9 C10 1.380(3) . ? C9 C8 1.382(3) . ? C14 C15 1.529(3) . ? C14 C16 1.534(3) . ? C14 C17 1.538(4) . ? C20 C22 1.527(4) . ? C20 C23 1.536(3) . ? C20 C21 1.537(4) . ? C10 C19 1.516(3) . ? C3 C4 1.384(3) . ? C32 C31 1.373(4) . ? C5 C4 1.372(3) . ? C4 C18 1.519(3) . ? C30 C31 1.351(4) . ? C28 C29 1.334(5) . ? C25 C26 1.492(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 O1 P O2 116.90(7) . . ? O1 P N1 119.86(8) . . ? O2 P N1 123.24(8) . . ? O1 P O3 93.24(7) . . ? O2 P O3 91.60(7) . . ? N1 P O3 85.54(7) . . ? O1 P N3 90.07(8) . . ? O2 P N3 87.72(8) . . ? N1 P N3 92.00(8) . . ? O3 P N3 176.56(8) . . ? C13 O2 P 128.24(12) . . ? C27 O3 P 111.25(12) . . ? C1 O1 P 130.16(12) . . ? C30 N3 N4 110.52(19) . . ? C30 N3 P 131.79(17) . . ? N4 N3 P 117.67(15) . . ? C24 O6 C25 116.43(19) . . ? C6 C1 C2 123.79(19) . . ? C6 C1 O1 116.11(18) . . ? C2 C1 O1 119.63(18) . . ? C27 N2 N1 104.24(16) . . ? C8 C13 C12 123.14(18) . . ? C8 C13 O2 116.61(18) . . ? C12 C13 O2 119.88(17) . . ? N2 C27 O3 120.95(18) . . ? N2 C27 O4 125.54(19) . . ? O3 C27 O4 113.50(18) . . ? C24 N1 N2 111.67(16) . . ? C24 N1 P 131.02(14) . . ? N2 N1 P 117.04(12) . . ? C5 C6 C1 117.5(2) . . ? C5 C6 C7 119.92(19) . . ? C1 C6 C7 122.56(18) . . ? C11 C12 C13 115.09(19) . . ? C11 C12 C20 120.84(19) . . ? C13 C12 C20 123.96(19) . . ? C6 C7 C8 114.01(16) . . ? C10 C11 C12 123.9(2) . . ? C1 C2 C3 114.9(2) . . ? C1 C2 C14 124.92(19) . . ? C3 C2 C14 120.2(2) . . ? C32 N4 N3 104.4(2) . . ? C27 O4 C28 114.8(2) . . ? C10 C9 C8 121.4(2) . . ? C9 C8 C13 118.05(19) . . ? C9 C8 C7 120.04(18) . . ? C13 C8 C7 121.85(18) . . ? C15 C14 C16 109.1(2) . . ? C15 C14 C2 111.15(18) . . ? C16 C14 C2 110.35(19) . . ? C15 C14 C17 105.9(2) . . ? C16 C14 C17 108.3(2) . . ? C2 C14 C17 111.9(2) . . ? C22 C20 C23 107.2(2) . . ? C22 C20 C21 109.6(2) . . ? C23 C20 C21 107.3(2) . . ? C22 C20 C12 110.3(2) . . ? C23 C20 C12 111.34(19) . . ? C21 C20 C12 111.00(19) . . ? C9 C10 C11 118.1(2) . . ? C9 C10 C19 121.6(2) . . ? C11 C10 C19 120.3(2) . . ? C4 C3 C2 123.5(2) . . ? O5 C24 O6 125.5(2) . . ? O5 C24 N1 124.3(2) . . ? O6 C24 N1 109.95(18) . . ? N4 C32 C31 112.0(2) . . ? C4 C5 C6 122.0(2) . . ? C5 C4 C3 118.3(2) . . ? C5 C4 C18 121.5(2) . . ? C3 C4 C18 120.2(2) . . ? C31 C30 N3 107.4(3) . . ? C30 C31 C32 105.6(2) . . ? C29 C28 O4 112.1(3) . . ? O6 C25 C26 107.3(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.559 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.050 #===END data_compd13b _database_code_depnum_ccdc_archive 'CCDC 280918' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H55 N4 O6 P' _chemical_formula_weight 730.86 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 17.235(3) _cell_length_b 18.659(4) _cell_length_c 13.113(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4217.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NEEDLES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type 'EMPIRICAL, SADABS' _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9888 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26032 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.23 _reflns_number_total 5200 _reflns_number_gt 2460 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.0277P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5200 _refine_ls_number_parameters 339 _refine_ls_number_restraints 388 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.980 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.25458(4) 0.2500 0.56912(5) 0.0574(3) Uani 1 d SU . . O1 O 0.30299(7) 0.17772(7) 0.57410(8) 0.0551(4) Uani 1 d U . . O2 O 0.23990(9) 0.2500 0.69967(12) 0.0584(5) Uani 1 d SU . . C24 C 0.16585(14) 0.2500 0.72376(19) 0.0535(7) Uani 1 d SU . . N2 N 0.11440(12) 0.2500 0.65404(16) 0.0605(6) Uani 1 d SU . . N1 N 0.15763(12) 0.2500 0.56120(16) 0.0695(7) Uani 1 d SU . . O3 O 0.14639(11) 0.2500 0.82059(13) 0.0770(6) Uani 1 d SDU . . C25 C 0.2070(2) 0.2560(7) 0.8985(3) 0.0729(15) Uani 0.50 d PDU A -1 H25 H 0.2532 0.2790 0.8701 0.087 Uiso 0.50 calc PR A -1 C26 C 0.1753(5) 0.2996(4) 0.9857(4) 0.135(3) Uani 0.50 d PDU A -1 H26A H 0.1669 0.3480 0.9636 0.203 Uiso 0.50 calc PR A -1 H26B H 0.2118 0.2993 1.0411 0.203 Uiso 0.50 calc PR A -1 H26C H 0.1270 0.2793 1.0082 0.203 Uiso 0.50 calc PR A -1 C27 C 0.2246(4) 0.1801(4) 0.9279(5) 0.1078(19) Uani 0.50 d PDU A -1 H27A H 0.2460 0.1552 0.8703 0.162 Uiso 0.50 calc PR A -1 H27B H 0.1778 0.1567 0.9493 0.162 Uiso 0.50 calc PR A -1 H27C H 0.2614 0.1797 0.9828 0.162 Uiso 0.50 calc PR A -1 C28 C 0.1098(2) 0.2153(3) 0.4776(3) 0.0649(11) Uani 0.50 d PU B -1 O4 O 0.12492(19) 0.16499(19) 0.4268(2) 0.0886(10) Uani 0.50 d PU B -1 O5 O 0.04853(14) 0.2500 0.47287(18) 0.1097(9) Uani 1 d SDU . . C29 C -0.0094(3) 0.2325(8) 0.3932(4) 0.111(5) Uani 0.50 d PDU B -1 H29 H -0.0083 0.1812 0.3774 0.134 Uiso 0.50 calc PR B -1 C30 C 0.0103(4) 0.2751(10) 0.3022(5) 0.226(11) Uani 0.50 d PDU B -1 H30A H 0.0656 0.2764 0.2940 0.339 Uiso 0.50 calc PR B -1 H30B H -0.0090 0.3230 0.3102 0.339 Uiso 0.50 calc PR B -1 H30C H -0.0128 0.2536 0.2430 0.339 Uiso 0.50 calc PR B -1 C31 C -0.0861(3) 0.2531(15) 0.4403(4) 0.207(4) Uani 0.50 d PDU B -1 H31A H -0.0813 0.2534 0.5132 0.311 Uiso 0.50 calc PR B -1 H31B H -0.1251 0.2191 0.4204 0.311 Uiso 0.50 calc PR B -1 H31C H -0.1008 0.3000 0.4171 0.311 Uiso 0.50 calc PR B -1 N3 N 0.26481(12) 0.2500 0.43615(16) 0.0586(6) Uani 1 d SU . . C32 C 0.3018(3) 0.1955(3) 0.3719(3) 0.0715(12) Uani 0.50 d PU C -1 H32 H 0.3239 0.1532 0.3957 0.086 Uiso 0.50 calc PR C -1 N4 N 0.2989(3) 0.2149(4) 0.2776(6) 0.091(2) Uani 0.50 d PU C -1 C34 C 0.2375(3) 0.2947(3) 0.3730(3) 0.0711(12) Uani 0.50 d PU C -1 H34 H 0.2074 0.3341 0.3906 0.085 Uiso 0.50 calc PR C -1 C33 C 0.2576(4) 0.2777(5) 0.2778(7) 0.082(2) Uani 0.50 d PU C -1 H33 H 0.2455 0.3044 0.2201 0.098 Uiso 0.50 calc PR C -1 C1 C 0.33732(10) 0.14575(11) 0.66112(13) 0.0571(5) Uani 1 d U . . C2 C 0.31266(11) 0.07838(12) 0.69406(15) 0.0649(5) Uani 1 d U . . C3 C 0.35033(13) 0.05205(14) 0.77979(17) 0.0801(7) Uani 1 d U . . H3 H 0.3347 0.0080 0.8058 0.096 Uiso 1 calc R . . C4 C 0.40999(13) 0.08802(14) 0.82861(17) 0.0809(7) Uani 1 d U . . C5 C 0.43489(11) 0.15169(13) 0.78872(15) 0.0696(6) Uani 1 d U . . H5 H 0.4764 0.1753 0.8192 0.084 Uiso 1 calc R . . C6 C 0.39976(10) 0.18174(11) 0.70402(14) 0.0553(5) Uani 1 d U . . C7 C 0.43158(14) 0.2500 0.6582(2) 0.0554(7) Uani 1 d SU . . H7A H 0.4205 0.2500 0.5857 0.067 Uiso 1 calc SR . . H7B H 0.4875 0.2500 0.6662 0.067 Uiso 1 calc SR . . C14 C 0.25011(13) 0.03359(12) 0.64045(18) 0.0759(6) Uani 1 d U . . C15 C 0.27225(17) 0.02218(15) 0.5279(2) 0.1032(9) Uani 1 d U . . H15A H 0.2732 0.0676 0.4935 0.155 Uiso 1 calc R . . H15B H 0.2347 -0.0085 0.4960 0.155 Uiso 1 calc R . . H15C H 0.3226 0.0004 0.5241 0.155 Uiso 1 calc R . . C16 C 0.17135(13) 0.07006(17) 0.6471(2) 0.1195(11) Uani 1 d U . . H16A H 0.1598 0.0808 0.7170 0.179 Uiso 1 calc R . . H16B H 0.1322 0.0387 0.6201 0.179 Uiso 1 calc R . . H16C H 0.1723 0.1137 0.6083 0.179 Uiso 1 calc R . . C17 C 0.2420(2) -0.04098(16) 0.6873(3) 0.1335(12) Uani 1 d U . . H17A H 0.2906 -0.0659 0.6822 0.200 Uiso 1 calc R . . H17B H 0.2027 -0.0673 0.6514 0.200 Uiso 1 calc R . . H17C H 0.2276 -0.0366 0.7577 0.200 Uiso 1 calc R . . C18 C 0.44855(17) 0.05505(19) 0.9212(2) 0.1284(12) Uani 1 d U . . H18A H 0.4487 0.0038 0.9146 0.193 Uiso 1 calc R . . H18B H 0.4204 0.0684 0.9815 0.193 Uiso 1 calc R . . H18C H 0.5010 0.0721 0.9262 0.193 Uiso 1 calc R . . C1S C 0.5050(9) -0.0333(14) 0.5546(15) 0.235(7) Uani 0.50 d PDU D -1 C2S C 0.507(2) 0.0382(14) 0.5656(15) 0.240(9) Uani 0.50 d PDU D -1 H2S H 0.5127 0.0588 0.6297 0.288 Uiso 0.50 calc PR D -1 C3S C 0.4988(15) 0.0804(14) 0.4803(17) 0.256(8) Uani 0.50 d PDU D -1 H3S H 0.5076 0.1296 0.4831 0.307 Uiso 0.50 calc PR D -1 C4S C 0.4786(17) 0.0490(16) 0.3945(14) 0.273(9) Uani 0.50 d PDU D -1 H4S H 0.4639 0.0768 0.3389 0.327 Uiso 0.50 calc PR D -1 C5S C 0.4790(16) -0.0211(17) 0.3865(15) 0.250(9) Uani 0.50 d PDU D -1 H5S H 0.4711 -0.0414 0.3225 0.300 Uiso 0.50 calc PR D -1 C6S C 0.4900(16) -0.0642(15) 0.4646(18) 0.256(8) Uani 0.50 d PDU D -1 H6S H 0.4874 -0.1138 0.4576 0.308 Uiso 0.50 calc PR D -1 C7S C 0.5111(19) -0.0795(16) 0.6371(16) 0.416(15) Uani 0.50 d PDU D -1 H7S1 H 0.5070 -0.1281 0.6139 0.623 Uiso 0.50 calc PR D -1 H7S2 H 0.4702 -0.0697 0.6848 0.623 Uiso 0.50 calc PR D -1 H7S3 H 0.5604 -0.0727 0.6699 0.623 Uiso 0.50 calc PR D -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.0355(4) 0.0948(6) 0.0420(4) 0.000 -0.0021(3) 0.000 O1 0.0425(7) 0.0743(9) 0.0485(7) 0.0013(6) -0.0037(5) -0.0036(6) O2 0.0327(9) 0.1010(15) 0.0416(9) 0.000 -0.0012(7) 0.000 C24 0.0405(14) 0.0704(18) 0.0496(14) 0.000 0.0030(11) 0.000 N2 0.0363(11) 0.0945(18) 0.0508(12) 0.000 -0.0009(10) 0.000 N1 0.0368(11) 0.128(2) 0.0436(12) 0.000 -0.0068(9) 0.000 O3 0.0474(11) 0.1357(19) 0.0479(11) 0.000 0.0045(9) 0.000 C25 0.065(2) 0.105(5) 0.0486(16) -0.006(6) -0.0038(15) 0.008(7) C26 0.169(7) 0.160(6) 0.076(4) -0.039(4) 0.001(4) 0.042(5) C27 0.118(5) 0.113(4) 0.092(5) 0.017(4) -0.017(4) 0.025(4) C28 0.050(2) 0.087(3) 0.058(2) -0.004(2) -0.0052(18) -0.008(2) O4 0.075(2) 0.110(3) 0.081(2) -0.0279(19) -0.0130(17) -0.0118(19) O5 0.0652(16) 0.171(3) 0.0933(17) 0.000 -0.0416(13) 0.000 C29 0.076(3) 0.171(14) 0.087(3) -0.016(4) -0.046(2) 0.014(4) C30 0.162(6) 0.40(3) 0.117(4) 0.078(10) -0.073(4) -0.068(11) C31 0.072(3) 0.410(13) 0.139(5) -0.115(12) -0.045(3) 0.042(12) N3 0.0507(13) 0.0816(16) 0.0435(12) 0.000 -0.0008(10) 0.000 C32 0.089(4) 0.066(3) 0.059(3) -0.001(2) 0.017(2) 0.002(3) N4 0.134(6) 0.085(3) 0.056(3) 0.000(2) 0.023(4) 0.004(4) C34 0.091(4) 0.070(3) 0.052(3) 0.002(2) -0.007(2) 0.010(3) C33 0.123(6) 0.079(4) 0.044(3) 0.007(2) -0.004(4) -0.012(4) C1 0.0439(10) 0.0759(14) 0.0515(10) 0.0043(10) -0.0006(8) -0.0033(9) C2 0.0538(11) 0.0753(14) 0.0656(12) 0.0069(11) 0.0020(10) -0.0090(10) C3 0.0654(14) 0.0919(17) 0.0831(15) 0.0268(13) -0.0019(12) -0.0105(12) C4 0.0569(13) 0.1072(19) 0.0785(15) 0.0313(14) -0.0098(11) -0.0040(13) C5 0.0445(11) 0.0960(17) 0.0684(13) 0.0103(12) -0.0098(10) -0.0038(11) C6 0.0370(9) 0.0717(13) 0.0572(11) 0.0019(9) -0.0001(8) -0.0001(9) C7 0.0330(13) 0.0712(18) 0.0620(16) 0.000 -0.0019(11) 0.000 C14 0.0661(14) 0.0752(15) 0.0864(16) -0.0016(12) -0.0034(11) -0.0170(12) C15 0.113(2) 0.094(2) 0.103(2) -0.0250(15) 0.0000(16) -0.0150(17) C16 0.0558(15) 0.122(2) 0.180(3) -0.047(2) -0.0011(17) -0.0250(15) C17 0.148(3) 0.103(2) 0.150(3) 0.026(2) -0.029(2) -0.055(2) C18 0.094(2) 0.174(3) 0.117(2) 0.077(2) -0.0366(17) -0.016(2) C1S 0.079(8) 0.381(16) 0.245(16) -0.063(13) 0.031(11) 0.058(13) C2S 0.141(17) 0.389(16) 0.190(16) -0.161(12) 0.043(14) 0.016(19) C3S 0.186(15) 0.326(15) 0.257(19) -0.125(13) 0.065(15) -0.054(15) C4S 0.188(18) 0.410(19) 0.220(17) -0.063(16) 0.042(14) -0.085(19) C5S 0.111(10) 0.42(2) 0.218(15) -0.183(15) 0.049(12) -0.065(15) C6S 0.103(11) 0.324(14) 0.342(18) -0.160(15) 0.091(15) 0.015(13) C7S 0.158(18) 0.63(3) 0.46(2) 0.18(2) 0.05(2) 0.11(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O1 1.5873(13) 7_565 ? P O1 1.5873(13) . ? P N1 1.674(2) . ? P O2 1.7306(18) . ? P N3 1.752(2) . ? O1 C1 1.417(2) . ? O2 C24 1.315(3) . ? C24 N2 1.274(3) . ? C24 O3 1.313(3) . ? N2 N1 1.427(3) . ? N1 C28 1.516(4) . ? N1 C28 1.516(4) 7_565 ? O3 C25 1.465(4) 7_565 ? O3 C25 1.465(4) . ? C25 C27 1.498(12) . ? C25 C26 1.506(8) . ? C28 O4 1.180(5) . ? C28 O5 1.241(4) . ? O5 C28 1.241(4) 7_565 ? O5 C29 1.482(5) . ? O5 C29 1.482(5) 7_565 ? C29 C30 1.473(12) . ? C29 C31 1.509(8) . ? N3 C34 1.266(4) 7_565 ? N3 C34 1.266(4) . ? N3 C32 1.466(5) 7_565 ? N3 C32 1.466(5) . ? C32 N4 1.290(8) . ? N4 C33 1.371(7) . ? C34 C33 1.334(10) . ? C1 C6 1.388(3) . ? C1 C2 1.396(3) . ? C2 C3 1.388(3) . ? C2 C14 1.535(3) . ? C3 C4 1.385(3) . ? C4 C5 1.367(3) . ? C4 C18 1.514(3) . ? C5 C6 1.384(3) . ? C6 C7 1.511(2) . ? C7 C6 1.511(2) 7_565 ? C14 C16 1.521(3) . ? C14 C17 1.527(3) . ? C14 C15 1.539(3) . ? C1S C6S 1.339(12) . ? C1S C2S 1.343(12) . ? C1S C7S 1.39(3) . ? C2S C3S 1.376(12) . ? C3S C4S 1.315(12) . ? C4S C5S 1.314(13) . ? C5S C6S 1.316(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P O1 116.36(9) 7_565 . ? O1 P N1 121.82(5) 7_565 . ? O1 P N1 121.82(5) . . ? O1 P O2 92.07(5) 7_565 . ? O1 P O2 92.07(5) . . ? N1 P O2 85.14(9) . . ? O1 P N3 89.32(6) 7_565 . ? O1 P N3 89.32(6) . . ? N1 P N3 92.22(11) . . ? O2 P N3 177.36(10) . . ? C1 O1 P 127.61(12) . . ? C24 O2 P 112.31(15) . . ? N2 C24 O3 121.1(2) . . ? N2 C24 O2 120.2(2) . . ? O3 C24 O2 118.7(2) . . ? C24 N2 N1 104.41(19) . . ? N2 N1 C28 109.5(2) . . ? N2 N1 C28 109.5(2) . 7_565 ? C28 N1 C28 50.5(4) . 7_565 ? N2 N1 P 117.91(15) . . ? C28 N1 P 125.9(2) . . ? C28 N1 P 125.9(2) 7_565 . ? C24 O3 C25 119.5(2) . 7_565 ? C24 O3 C25 119.5(2) . . ? C25 O3 C25 8.7(11) 7_565 . ? O3 C25 C27 104.6(7) . . ? O3 C25 C26 108.2(5) . . ? C27 C25 C26 112.9(6) . . ? O4 C28 O5 125.0(4) . . ? O4 C28 N1 128.9(4) . . ? O5 C28 N1 106.0(3) . . ? C28 O5 C28 62.9(4) 7_565 . ? C28 O5 C29 136.4(4) 7_565 . ? C28 O5 C29 119.6(5) . . ? C28 O5 C29 119.6(5) 7_565 7_565 ? C28 O5 C29 136.4(4) . 7_565 ? C29 O5 C29 25.4(11) . 7_565 ? C30 C29 O5 107.3(7) . . ? C30 C29 C31 113.3(12) . . ? O5 C29 C31 104.2(5) . . ? C34 N3 C34 82.4(4) 7_565 . ? C34 N3 C32 104.1(3) 7_565 7_565 ? C34 N3 C32 47.8(3) . 7_565 ? C34 N3 C32 47.8(3) 7_565 . ? C34 N3 C32 104.1(3) . . ? C32 N3 C32 87.9(4) 7_565 . ? C34 N3 P 127.8(2) 7_565 . ? C34 N3 P 127.8(2) . . ? C32 N3 P 128.0(2) 7_565 . ? C32 N3 P 128.0(2) . . ? N4 C32 N3 109.8(5) . . ? C32 N4 C33 105.0(8) . . ? N3 C34 C33 111.1(5) . . ? C34 C33 N4 109.8(9) . . ? C6 C1 C2 123.13(18) . . ? C6 C1 O1 116.53(17) . . ? C2 C1 O1 120.08(17) . . ? C3 C2 C1 115.28(19) . . ? C3 C2 C14 120.5(2) . . ? C1 C2 C14 124.24(19) . . ? C4 C3 C2 123.4(2) . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C18 121.5(2) . . ? C3 C4 C18 120.0(2) . . ? C4 C5 C6 121.5(2) . . ? C5 C6 C1 117.95(19) . . ? C5 C6 C7 120.12(19) . . ? C1 C6 C7 121.88(18) . . ? C6 C7 C6 114.9(2) . 7_565 ? C16 C14 C17 107.7(2) . . ? C16 C14 C2 110.9(2) . . ? C17 C14 C2 112.1(2) . . ? C16 C14 C15 109.7(2) . . ? C17 C14 C15 106.4(2) . . ? C2 C14 C15 109.90(19) . . ? C6S C1S C2S 121.8(12) . . ? C6S C1S C7S 115.8(17) . . ? C2S C1S C7S 122.1(16) . . ? C1S C2S C3S 118.7(11) . . ? C4S C3S C2S 117.8(13) . . ? C5S C4S C3S 120.7(14) . . ? C4S C5S C6S 123.2(15) . . ? C5S C6S C1S 116.8(13) . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.191 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.036 #===END data_compd14 _database_code_depnum_ccdc_archive 'CCDC 280919' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H58 N3 O7 P' _chemical_formula_weight 807.93 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 p_21/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 16.7166(11) _cell_length_b 15.0867(19) _cell_length_c 19.0574(14) _cell_angle_alpha 90.00 _cell_angle_beta 106.401(13) _cell_angle_gamma 90.00 _cell_volume 4610.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _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 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8091 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1317 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 24.98 _reflns_number_total 8091 _reflns_number_gt 2931 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0941P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8091 _refine_ls_number_parameters 564 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2268 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.2228 _refine_ls_wR_factor_gt 0.1616 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.020 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.75006(9) 0.62957(9) 0.20902(7) 0.0522(4) Uani 1 d . . . O1 O 0.8481(2) 0.6524(2) 0.23151(16) 0.0511(9) Uani 1 d . . . O2 O 0.6927(2) 0.7023(2) 0.15718(16) 0.0528(9) Uani 1 d . . . O3 O 0.7382(2) 0.6807(2) 0.28703(16) 0.0562(9) Uani 1 d . . . O4 O 0.6929(3) 0.6629(3) 0.38569(19) 0.0790(12) Uani 1 d . . . O5 O 0.6127(3) 0.4374(3) 0.1925(3) 0.126(2) Uani 1 d . . . O6 O 0.7416(3) 0.4105(3) 0.1890(2) 0.0791(12) Uani 1 d . . . O7 O 0.7559(2) 0.5709(2) 0.13863(15) 0.0569(9) Uani 1 d . . . N1 N 0.7156(3) 0.5378(3) 0.2412(2) 0.0621(13) Uani 1 d . . . N2 N 0.6893(3) 0.5462(3) 0.3059(2) 0.0716(14) Uani 1 d . . . N3 N 0.6330(3) 0.5636(3) 0.0102(2) 0.0697(14) Uani 1 d . . . C1 C 0.8930(3) 0.7180(3) 0.2801(3) 0.0480(13) Uani 1 d . . . C2 C 0.9549(3) 0.6934(3) 0.3430(3) 0.0495(13) Uani 1 d . . . C3 C 0.9966(3) 0.7634(4) 0.3861(3) 0.0620(15) Uani 1 d . . . H3 H 1.0367 0.7497 0.4295 0.074 Uiso 1 calc R . . C4 C 0.9819(4) 0.8515(4) 0.3679(3) 0.0629(15) Uani 1 d . . . C5 C 0.9245(3) 0.8704(4) 0.3019(3) 0.0591(14) Uani 1 d . . . H5 H 0.9155 0.9293 0.2874 0.071 Uiso 1 calc R . . C6 C 0.8797(3) 0.8050(3) 0.2565(3) 0.0499(13) Uani 1 d . . . C7 C 0.8209(3) 0.8309(3) 0.1830(3) 0.0560(14) Uani 1 d . . . H7A H 0.8185 0.7825 0.1489 0.067 Uiso 1 calc R . . H7B H 0.8439 0.8820 0.1646 0.067 Uiso 1 calc R . . C8 C 0.7328(4) 0.8528(3) 0.1843(2) 0.0550(14) Uani 1 d . . . C9 C 0.7121(4) 0.9393(4) 0.1940(3) 0.0749(18) Uani 1 d . . . H9 H 0.7533 0.9826 0.2019 0.090 Uiso 1 calc R . . C10 C 0.6321(5) 0.9638(5) 0.1923(3) 0.087(2) Uani 1 d . . . C11 C 0.5724(4) 0.8975(5) 0.1795(3) 0.083(2) Uani 1 d . . . H11 H 0.5181 0.9134 0.1779 0.099 Uiso 1 calc R . . C12 C 0.5884(4) 0.8085(4) 0.1690(3) 0.0636(16) Uani 1 d . . . C13 C 0.6717(4) 0.7888(4) 0.1738(2) 0.0564(14) Uani 1 d . . . C14 C 0.9776(4) 0.5970(3) 0.3655(3) 0.0624(15) Uani 1 d . . . C15 C 1.0556(5) 0.5913(5) 0.4308(4) 0.127(3) Uani 1 d . . . H15A H 1.0719 0.5304 0.4398 0.191 Uiso 1 calc R . . H15B H 1.0438 0.6157 0.4733 0.191 Uiso 1 calc R . . H15C H 1.1001 0.6241 0.4204 0.191 Uiso 1 calc R . . C16 C 0.9982(5) 0.5460(4) 0.3026(3) 0.111(3) Uani 1 d . . . H16A H 0.9479 0.5364 0.2639 0.167 Uiso 1 calc R . . H16B H 1.0227 0.4899 0.3203 0.167 Uiso 1 calc R . . H16C H 1.0366 0.5799 0.2844 0.167 Uiso 1 calc R . . C17 C 0.9074(4) 0.5502(4) 0.3867(3) 0.099(2) Uani 1 d . . . H17A H 0.8609 0.5425 0.3440 0.148 Uiso 1 calc R . . H17B H 0.8905 0.5852 0.4221 0.148 Uiso 1 calc R . . H17C H 0.9264 0.4933 0.4073 0.148 Uiso 1 calc R . . C18 C 1.0306(4) 0.9239(4) 0.4177(3) 0.095(2) Uani 1 d . . . H18A H 1.0658 0.9542 0.3935 0.142 Uiso 1 calc R . . H18B H 1.0643 0.8978 0.4622 0.142 Uiso 1 calc R . . H18C H 0.9924 0.9654 0.4289 0.142 Uiso 1 calc R . . C19 C 0.6094(5) 1.0594(4) 0.2038(4) 0.139(3) Uani 1 d . . . H19A H 0.5597 1.0605 0.2195 0.208 Uiso 1 calc R . . H19B H 0.5999 1.0915 0.1586 0.208 Uiso 1 calc R . . H19C H 0.6543 1.0866 0.2404 0.208 Uiso 1 calc R . . C20 C 0.5130(4) 0.7445(5) 0.1514(3) 0.0822(19) Uani 1 d . . . C21A C 0.5327(12) 0.6636(18) 0.2070(12) 0.154(10) Uani 0.50 d P . . H21A H 0.4924 0.6174 0.1896 0.231 Uiso 0.50 calc PR . . H21B H 0.5299 0.6831 0.2542 0.231 Uiso 0.50 calc PR . . H21C H 0.5875 0.6412 0.2109 0.231 Uiso 0.50 calc PR . . C21B C 0.5304(11) 0.6499(14) 0.1471(15) 0.122(8) Uani 0.50 d P . . H21D H 0.4791 0.6172 0.1365 0.183 Uiso 0.50 calc PR . . H21E H 0.5668 0.6304 0.1929 0.183 Uiso 0.50 calc PR . . H21F H 0.5566 0.6401 0.1089 0.183 Uiso 0.50 calc PR . . C22A C 0.4537(12) 0.7727(19) 0.0755(9) 0.149(10) Uani 0.50 d P . . H22A H 0.4858 0.7829 0.0418 0.223 Uiso 0.50 calc PR . . H22B H 0.4249 0.8261 0.0811 0.223 Uiso 0.50 calc PR . . H22C H 0.4138 0.7264 0.0571 0.223 Uiso 0.50 calc PR . . C22B C 0.5075(13) 0.7031(15) 0.0748(11) 0.123(7) Uani 0.50 d P . . H22D H 0.5568 0.6689 0.0778 0.184 Uiso 0.50 calc PR . . H22E H 0.5029 0.7497 0.0395 0.184 Uiso 0.50 calc PR . . H22F H 0.4594 0.6655 0.0600 0.184 Uiso 0.50 calc PR . . C23A C 0.4639(12) 0.7581(12) 0.2090(10) 0.105(6) Uani 0.50 d P . . H23A H 0.4190 0.7161 0.2003 0.158 Uiso 0.50 calc PR . . H23B H 0.4417 0.8172 0.2048 0.158 Uiso 0.50 calc PR . . H23C H 0.5007 0.7495 0.2572 0.158 Uiso 0.50 calc PR . . C23B C 0.4302(11) 0.7855(18) 0.1470(17) 0.187(12) Uani 0.50 d P . . H23D H 0.4125 0.8210 0.1035 0.281 Uiso 0.50 calc PR . . H23E H 0.4350 0.8222 0.1891 0.281 Uiso 0.50 calc PR . . H23F H 0.3899 0.7397 0.1454 0.281 Uiso 0.50 calc PR . . C24 C 0.6837(5) 0.4575(4) 0.2035(3) 0.0737(18) Uani 1 d . . . C28 C 0.7058(4) 0.6256(4) 0.3265(3) 0.0644(15) Uani 1 d . . . C29 C 0.6570(5) 0.6054(5) 0.4309(3) 0.096(2) Uani 1 d . . . H29 H 0.6172 0.5639 0.3999 0.115 Uiso 1 calc R . . C30 C 0.6132(6) 0.6661(6) 0.4694(5) 0.163(4) Uani 1 d . . . H30A H 0.6528 0.7061 0.4998 0.245 Uiso 1 calc R . . H30B H 0.5869 0.6320 0.4991 0.245 Uiso 1 calc R . . H30C H 0.5718 0.6993 0.4341 0.245 Uiso 1 calc R . . C31 C 0.7264(6) 0.5555(7) 0.4833(4) 0.177(4) Uani 1 d . . . H31A H 0.7590 0.5252 0.4566 0.265 Uiso 1 calc R . . H31B H 0.7033 0.5131 0.5097 0.265 Uiso 1 calc R . . H31C H 0.7613 0.5963 0.5172 0.265 Uiso 1 calc R . . C32 C 0.7735(4) 0.6023(3) 0.0759(2) 0.0523(14) Uani 1 d . . . C33 C 0.8508(3) 0.6311(4) 0.0770(3) 0.0603(14) Uani 1 d . . . H33 H 0.8932 0.6321 0.1208 0.072 Uiso 1 calc R . . C34 C 0.8665(4) 0.6592(4) 0.0125(3) 0.0709(17) Uani 1 d . . . H34 H 0.9195 0.6795 0.0141 0.085 Uiso 1 calc R . . C35 C 0.8067(4) 0.6578(4) -0.0523(3) 0.0690(17) Uani 1 d . . . H35 H 0.8181 0.6784 -0.0944 0.083 Uiso 1 calc R . . C36 C 0.7269(4) 0.6249(4) -0.0554(3) 0.0594(15) Uani 1 d . . . C37 C 0.6622(4) 0.6192(4) -0.1207(3) 0.0805(18) Uani 1 d . . . H37 H 0.6707 0.6387 -0.1644 0.097 Uiso 1 calc R . . C38 C 0.5883(5) 0.5858(4) -0.1201(3) 0.094(2) Uani 1 d . . . H38 H 0.5457 0.5802 -0.1635 0.113 Uiso 1 calc R . . C39 C 0.5757(4) 0.5591(4) -0.0530(3) 0.0849(19) Uani 1 d . . . H39 H 0.5236 0.5369 -0.0536 0.102 Uiso 1 calc R . . C40 C 0.7084(4) 0.5960(3) 0.0092(3) 0.0567(14) Uani 1 d . . . C41 C 0.1067(6) 0.6448(7) 0.1481(5) 0.140(3) Uani 1 d D . . H41 H 0.0700 0.6161 0.1692 0.168 Uiso 1 calc R . . C42 C 0.1665(7) 0.6014(9) 0.1229(5) 0.178(5) Uani 1 d D . . H42 H 0.1647 0.5401 0.1273 0.214 Uiso 1 calc R . . C44 C 0.2125(10) 0.7195(13) 0.1000(10) 0.283(12) Uani 1 d D . . H44 H 0.2531 0.7474 0.0832 0.339 Uiso 1 calc R . . C45 C 0.1686(8) 0.7878(9) 0.1189(7) 0.209(8) Uani 1 d D . . H45 H 0.1764 0.8489 0.1189 0.251 Uiso 1 calc R . . C43 C 0.2270(9) 0.6291(12) 0.0932(9) 0.301(13) Uani 1 d D . . H43 H 0.2650 0.5986 0.0747 0.362 Uiso 1 calc R . . C46 C 0.1081(8) 0.7360(8) 0.1382(8) 0.217(8) Uani 1 d D . . C47 C 0.0558(11) 0.7831(10) 0.1648(8) 0.276(9) Uani 1 d . . . H47A H 0.0082 0.7999 0.1256 0.414 Uiso 1 calc R . . H47B H 0.0836 0.8354 0.1884 0.414 Uiso 1 calc R . . H47C H 0.0380 0.7480 0.1997 0.414 Uiso 1 calc R . . C25 C 0.7074(7) 0.3355(5) 0.1377(7) 0.154(4) Uani 1 d . . . H25 H 0.6464 0.3321 0.1250 0.185 Uiso 1 calc R . . C26 C 0.7344(14) 0.3402(8) 0.0798(7) 0.353(14) Uani 1 d . . . H26A H 0.7924 0.3245 0.0929 0.529 Uiso 1 calc R . . H26B H 0.7274 0.3995 0.0609 0.529 Uiso 1 calc R . . H26C H 0.7033 0.2999 0.0432 0.529 Uiso 1 calc R . . C27 C 0.7417(19) 0.2675(8) 0.1701(6) 0.57(3) Uani 1 d . . . H27A H 0.7123 0.2159 0.1468 0.849 Uiso 1 calc R . . H27B H 0.7406 0.2694 0.2202 0.849 Uiso 1 calc R . . H27C H 0.7984 0.2650 0.1683 0.849 Uiso 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 P 0.0616(10) 0.0582(9) 0.0385(7) -0.0029(7) 0.0169(7) -0.0084(8) O1 0.055(2) 0.054(2) 0.0457(18) -0.0022(16) 0.0158(17) -0.0061(18) O2 0.056(2) 0.062(2) 0.0416(18) 0.0013(17) 0.0152(17) -0.0010(19) O3 0.069(2) 0.063(2) 0.0424(19) -0.0076(17) 0.0256(18) -0.0098(19) O4 0.105(3) 0.093(3) 0.050(2) -0.014(2) 0.039(2) -0.022(2) O5 0.094(4) 0.126(4) 0.168(5) -0.066(4) 0.053(4) -0.047(4) O6 0.087(3) 0.067(3) 0.093(3) -0.023(2) 0.042(3) -0.020(2) O7 0.080(3) 0.057(2) 0.0375(18) -0.0053(16) 0.0227(18) -0.0079(19) N1 0.089(4) 0.060(3) 0.044(2) -0.010(2) 0.029(2) -0.024(3) N2 0.089(4) 0.083(4) 0.048(3) -0.010(3) 0.028(3) -0.029(3) N3 0.080(4) 0.082(3) 0.046(3) -0.011(2) 0.015(3) -0.022(3) C1 0.050(3) 0.047(3) 0.050(3) -0.002(3) 0.019(3) -0.003(3) C2 0.044(3) 0.061(4) 0.045(3) 0.006(3) 0.014(3) 0.004(3) C3 0.059(4) 0.073(4) 0.051(3) -0.002(3) 0.011(3) 0.000(3) C4 0.061(4) 0.059(4) 0.069(4) -0.010(3) 0.019(3) -0.012(3) C5 0.060(4) 0.053(3) 0.068(4) 0.003(3) 0.024(3) -0.004(3) C6 0.048(3) 0.055(3) 0.051(3) 0.004(3) 0.020(3) -0.004(3) C7 0.066(4) 0.054(3) 0.051(3) 0.009(3) 0.022(3) -0.002(3) C8 0.067(4) 0.052(4) 0.045(3) 0.004(3) 0.013(3) 0.010(3) C9 0.085(5) 0.059(4) 0.073(4) 0.002(3) 0.009(4) 0.007(4) C10 0.090(6) 0.088(5) 0.077(4) -0.003(4) 0.014(4) 0.033(5) C11 0.069(5) 0.110(6) 0.070(4) 0.002(4) 0.020(4) 0.031(5) C12 0.062(4) 0.086(5) 0.046(3) 0.000(3) 0.020(3) 0.014(4) C13 0.064(4) 0.063(4) 0.044(3) -0.005(3) 0.017(3) 0.007(3) C14 0.061(4) 0.060(4) 0.061(3) 0.010(3) 0.010(3) 0.004(3) C15 0.116(6) 0.102(6) 0.129(6) 0.032(5) -0.023(5) 0.023(5) C16 0.163(7) 0.086(5) 0.090(5) 0.016(4) 0.043(5) 0.052(5) C17 0.104(6) 0.080(5) 0.116(5) 0.045(4) 0.038(5) 0.006(4) C18 0.089(5) 0.087(5) 0.096(5) -0.024(4) 0.008(4) -0.019(4) C19 0.143(7) 0.093(6) 0.172(8) -0.015(5) 0.031(6) 0.057(5) C20 0.062(5) 0.116(6) 0.069(4) -0.002(4) 0.018(4) -0.005(5) C21A 0.085(13) 0.23(3) 0.161(19) 0.08(2) 0.049(15) -0.042(16) C21B 0.054(10) 0.129(16) 0.19(2) -0.069(19) 0.043(16) -0.036(11) C22A 0.066(13) 0.28(3) 0.083(12) 0.052(17) -0.010(11) -0.065(15) C22B 0.096(16) 0.159(19) 0.098(14) -0.027(14) 0.002(12) -0.043(13) C23A 0.113(16) 0.111(12) 0.121(13) -0.013(12) 0.079(12) -0.016(13) C23B 0.044(12) 0.26(3) 0.24(3) -0.06(3) 0.021(18) 0.005(15) C24 0.077(5) 0.082(5) 0.069(4) -0.010(3) 0.033(4) -0.026(4) C28 0.078(4) 0.080(4) 0.040(3) -0.011(3) 0.023(3) -0.016(4) C29 0.133(6) 0.113(6) 0.062(4) -0.007(4) 0.061(5) -0.034(5) C30 0.230(11) 0.172(8) 0.143(7) -0.017(6) 0.143(8) -0.021(8) C31 0.183(10) 0.257(12) 0.105(7) 0.070(7) 0.064(7) 0.024(9) C32 0.072(4) 0.053(3) 0.038(3) 0.000(2) 0.025(3) 0.004(3) C33 0.058(4) 0.081(4) 0.046(3) 0.001(3) 0.020(3) 0.006(3) C34 0.066(4) 0.089(4) 0.065(4) -0.003(3) 0.031(4) 0.000(3) C35 0.071(5) 0.091(5) 0.055(4) 0.008(3) 0.034(3) 0.001(4) C36 0.072(4) 0.070(4) 0.039(3) -0.002(3) 0.021(3) 0.004(3) C37 0.087(5) 0.109(5) 0.050(4) 0.007(3) 0.026(4) -0.002(4) C38 0.111(6) 0.123(6) 0.044(4) -0.001(4) 0.015(4) -0.018(5) C39 0.089(5) 0.100(5) 0.069(4) -0.013(4) 0.028(4) -0.027(4) C40 0.068(4) 0.061(4) 0.043(3) -0.002(3) 0.020(3) 0.002(3) C41 0.125(8) 0.141(9) 0.181(9) 0.004(7) 0.086(7) 0.010(7) C42 0.119(9) 0.281(15) 0.120(8) 0.041(9) 0.009(7) -0.036(11) C44 0.125(14) 0.50(3) 0.214(16) -0.04(2) 0.027(11) 0.110(18) C45 0.129(11) 0.242(15) 0.242(14) 0.127(13) 0.028(10) -0.071(11) C43 0.105(10) 0.62(4) 0.173(12) -0.08(2) 0.023(9) 0.087(19) C46 0.208(16) 0.156(12) 0.217(15) -0.045(11) -0.052(12) 0.062(12) C47 0.36(2) 0.217(16) 0.278(17) -0.041(13) 0.127(17) 0.046(15) C25 0.206(10) 0.067(5) 0.250(13) -0.067(7) 0.161(10) -0.039(6) C26 0.77(4) 0.163(12) 0.188(12) -0.095(10) 0.24(2) -0.146(17) C27 1.38(8) 0.099(9) 0.105(9) -0.042(8) 0.03(2) 0.00(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O2 1.602(3) . ? P O1 1.610(3) . ? P O7 1.633(3) . ? P N1 1.681(4) . ? P O3 1.735(3) . ? O1 C1 1.417(5) . ? O2 C13 1.410(6) . ? O3 C28 1.335(6) . ? O4 C28 1.332(6) . ? O4 C29 1.464(6) . ? O5 C24 1.184(7) . ? O6 C24 1.292(7) . ? O6 C25 1.500(9) . ? O7 C32 1.392(5) . ? N1 N2 1.426(5) . ? N1 C24 1.433(7) . ? N2 C28 1.266(6) . ? N3 C39 1.312(7) . ? N3 C40 1.357(6) . ? C1 C6 1.384(6) . ? C1 C2 1.395(6) . ? C2 C3 1.397(6) . ? C2 C14 1.533(7) . ? C3 C4 1.379(7) . ? C4 C5 1.379(7) . ? C4 C18 1.523(7) . ? C5 C6 1.384(6) . ? C6 C7 1.518(6) . ? C7 C8 1.517(7) . ? C8 C9 1.376(7) . ? C8 C13 1.378(7) . ? C9 C10 1.378(8) . ? C10 C11 1.386(8) . ? C10 C19 1.523(8) . ? C11 C12 1.395(8) . ? C12 C13 1.401(7) . ? C12 C20 1.548(8) . ? C14 C17 1.518(7) . ? C14 C15 1.530(8) . ? C14 C16 1.544(7) . ? C20 C21B 1.46(2) . ? C20 C23B 1.498(19) . ? C20 C23A 1.558(16) . ? C20 C22A 1.564(16) . ? C20 C22B 1.567(18) . ? C20 C21A 1.59(2) . ? C29 C30 1.488(9) . ? C29 C31 1.503(10) . ? C32 C33 1.358(7) . ? C32 C40 1.424(7) . ? C33 C34 1.394(7) . ? C34 C35 1.352(7) . ? C35 C36 1.409(7) . ? C36 C37 1.402(7) . ? C36 C40 1.419(6) . ? C37 C38 1.337(8) . ? C38 C39 1.414(7) . ? C41 C46 1.390(8) . ? C41 C42 1.389(8) . ? C42 C43 1.357(9) . ? C44 C45 1.371(9) . ? C44 C43 1.397(10) . ? C45 C46 1.408(9) . ? C46 C47 1.332(14) . ? C25 C27 1.250(16) . ? C25 C26 1.306(13) . ? 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 O2 P O1 113.91(17) . . ? O2 P O7 91.66(17) . . ? O1 P O7 92.38(18) . . ? O2 P N1 125.6(2) . . ? O1 P N1 120.5(2) . . ? O7 P N1 87.71(18) . . ? O2 P O3 91.74(17) . . ? O1 P O3 91.77(17) . . ? O7 P O3 173.06(18) . . ? N1 P O3 85.39(18) . . ? C1 O1 P 129.4(3) . . ? C13 O2 P 129.7(3) . . ? C28 O3 P 111.6(3) . . ? C28 O4 C29 116.1(5) . . ? C24 O6 C25 112.5(6) . . ? C32 O7 P 126.7(3) . . ? N2 N1 C24 110.3(4) . . ? N2 N1 P 117.6(3) . . ? C24 N1 P 129.1(3) . . ? C28 N2 N1 105.0(4) . . ? C39 N3 C40 116.5(5) . . ? C6 C1 C2 122.9(5) . . ? C6 C1 O1 116.3(4) . . ? C2 C1 O1 120.2(4) . . ? C1 C2 C3 115.5(5) . . ? C1 C2 C14 123.9(5) . . ? C3 C2 C14 120.6(4) . . ? C4 C3 C2 123.9(5) . . ? C3 C4 C5 117.2(5) . . ? C3 C4 C18 120.6(5) . . ? C5 C4 C18 122.2(5) . . ? C4 C5 C6 122.5(5) . . ? C1 C6 C5 117.6(5) . . ? C1 C6 C7 123.1(5) . . ? C5 C6 C7 119.2(5) . . ? C6 C7 C8 114.8(4) . . ? C9 C8 C13 118.7(6) . . ? C9 C8 C7 119.4(5) . . ? C13 C8 C7 121.9(5) . . ? C10 C9 C8 122.0(6) . . ? C9 C10 C11 117.2(6) . . ? C9 C10 C19 122.0(7) . . ? C11 C10 C19 120.8(7) . . ? C10 C11 C12 124.2(6) . . ? C11 C12 C13 115.0(6) . . ? C11 C12 C20 117.0(6) . . ? C13 C12 C20 127.9(6) . . ? C8 C13 C12 122.9(5) . . ? C8 C13 O2 117.4(5) . . ? C12 C13 O2 119.1(5) . . ? C17 C14 C15 107.6(5) . . ? C17 C14 C2 111.5(5) . . ? C15 C14 C2 111.6(5) . . ? C17 C14 C16 109.4(5) . . ? C15 C14 C16 106.1(5) . . ? C2 C14 C16 110.4(4) . . ? C21B C20 C23B 126.5(13) . . ? C21B C20 C12 117.3(8) . . ? C23B C20 C12 115.9(11) . . ? C21B C20 C23A 108.7(12) . . ? C23B C20 C23A 47.3(11) . . ? C12 C20 C23A 108.9(8) . . ? C21B C20 C22A 107.3(14) . . ? C23B C20 C22A 60.0(12) . . ? C12 C20 C22A 107.2(8) . . ? C23A C20 C22A 107.0(12) . . ? C21B C20 C22B 61.3(11) . . ? C23B C20 C22B 107.5(13) . . ? C12 C20 C22B 106.3(8) . . ? C23A C20 C22B 143.6(11) . . ? C22A C20 C22B 52.5(10) . . ? C21B C20 C21A 44.1(10) . . ? C23B C20 C21A 111.6(15) . . ? C12 C20 C21A 109.5(9) . . ? C23A C20 C21A 71.5(11) . . ? C22A C20 C21A 141.6(13) . . ? C22B C20 C21A 105.3(14) . . ? O5 C24 O6 126.6(6) . . ? O5 C24 N1 121.2(7) . . ? O6 C24 N1 112.1(6) . . ? N2 C28 O4 126.2(5) . . ? N2 C28 O3 120.1(5) . . ? O4 C28 O3 113.8(5) . . ? O4 C29 C30 105.5(6) . . ? O4 C29 C31 108.7(6) . . ? C30 C29 C31 112.0(6) . . ? C33 C32 O7 121.8(5) . . ? C33 C32 C40 121.3(4) . . ? O7 C32 C40 116.8(5) . . ? C32 C33 C34 120.0(5) . . ? C35 C34 C33 121.7(5) . . ? C34 C35 C36 119.5(5) . . ? C37 C36 C35 122.8(5) . . ? C37 C36 C40 116.7(5) . . ? C35 C36 C40 120.4(5) . . ? C38 C37 C36 119.8(6) . . ? C37 C38 C39 119.3(6) . . ? N3 C39 C38 124.0(6) . . ? N3 C40 C36 123.6(5) . . ? N3 C40 C32 119.3(5) . . ? C36 C40 C32 117.1(5) . . ? C46 C41 C42 112.3(10) . . ? C43 C42 C41 133.9(13) . . ? C45 C44 C43 151.4(17) . . ? C44 C45 C46 97.4(13) . . ? C42 C43 C44 95.3(14) . . ? C47 C46 C41 116.1(13) . . ? C47 C46 C45 113.6(13) . . ? C41 C46 C45 128.7(12) . . ? C27 C25 C26 104.0(14) . . ? C27 C25 O6 105.0(12) . . ? C26 C25 O6 110.5(8) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.366 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.051 #===END data_compd15 _database_code_depnum_ccdc_archive 'CCDC 280920' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H50 N3 O6 P S' _chemical_formula_weight 647.79 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P_21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9655(9) _cell_length_b 22.0001(17) _cell_length_c 13.9870(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.2570(10) _cell_angle_gamma 90.00 _cell_volume 3671.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NEEDLES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type 'EMPIRICAL, SADABS' _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34926 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6468 _reflns_number_gt 5040 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0642P)^2^+1.0733P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6468 _refine_ls_number_parameters 411 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 P P 0.18329(4) 0.17382(2) 0.91226(3) 0.03535(13) Uani 1 1 d . . . S S -0.02786(4) 0.20703(2) 0.75727(4) 0.04802(15) Uani 1 1 d . . . O3 O 0.31072(10) 0.18566(5) 0.96183(9) 0.0397(3) Uani 1 1 d . . . O1 O 0.19240(10) 0.14405(5) 0.80742(8) 0.0405(3) Uani 1 1 d . . . N1 N 0.19922(12) 0.09707(6) 0.95769(11) 0.0388(3) Uani 1 1 d . . . O6 O 0.04166(11) 0.06465(6) 0.88186(10) 0.0511(3) Uani 1 1 d . . . N2 N 0.30804(12) 0.08492(7) 1.00009(12) 0.0435(4) Uani 1 1 d . . . O2 O 0.18858(9) 0.24484(5) 0.86863(9) 0.0389(3) Uani 1 1 d . . . N3 N 0.08099(12) 0.18872(7) 0.97810(11) 0.0417(4) Uani 1 1 d . . . H H 0.0504 0.2235 0.9660 0.050 Uiso 1 1 calc R . . O4 O 0.46435(10) 0.14631(6) 1.03359(10) 0.0505(3) Uani 1 1 d . . . C23 C 0.14206(16) 0.04697(8) 0.92170(14) 0.0445(4) Uani 1 1 d . . . C17 C 0.10901(15) 0.29022(8) 0.85866(12) 0.0377(4) Uani 1 1 d . . . C6 C 0.08395(16) 0.19744(8) 0.68194(13) 0.0429(4) Uani 1 1 d . . . O5 O 0.17320(13) -0.00475(6) 0.92809(13) 0.0700(5) Uani 1 1 d . . . C27 C 0.36047(15) 0.13472(8) 0.99961(13) 0.0406(4) Uani 1 1 d . . . C1 C 0.18180(16) 0.16786(8) 0.71503(13) 0.0406(4) Uani 1 1 d . . . C12 C 0.00580(15) 0.27912(8) 0.80780(13) 0.0414(4) Uani 1 1 d . . . C16 C 0.13532(16) 0.34868(8) 0.89496(13) 0.0412(4) Uani 1 1 d . . . C15 C 0.05177(17) 0.39278(9) 0.88026(14) 0.0494(5) Uani 1 1 d . . . H15 H 0.0671 0.4317 0.9034 0.059 Uiso 1 1 calc R . . C2 C 0.26718(16) 0.15534(9) 0.65434(13) 0.0452(4) Uani 1 1 d . . . C13 C -0.07387(16) 0.32493(9) 0.79657(15) 0.0488(5) Uani 1 1 d . . . H13 H -0.1428 0.3169 0.7638 0.059 Uiso 1 1 calc R . . C14 C -0.05187(18) 0.38216(9) 0.83356(15) 0.0523(5) Uani 1 1 d . . . C3 C 0.24811(18) 0.17629(10) 0.56020(15) 0.0540(5) Uani 1 1 d . . . H3 H 0.3028 0.1688 0.5178 0.065 Uiso 1 1 calc R . . C5 C 0.07074(18) 0.21746(9) 0.58767(14) 0.0513(5) Uani 1 1 d . . . H5 H 0.0055 0.2378 0.5661 0.062 Uiso 1 1 calc R . . C31 C 0.02944(17) 0.15487(10) 1.05471(15) 0.0506(5) Uani 1 1 d . . . H31 H 0.0267 0.1117 1.0377 0.061 Uiso 1 1 calc R . . C28 C 0.53661(16) 0.09358(9) 1.05815(15) 0.0491(5) Uani 1 1 d . . . H28 H 0.4942 0.0628 1.0908 0.059 Uiso 1 1 calc R . . C7 C 0.37652(18) 0.12226(10) 0.68751(15) 0.0540(5) Uani 1 1 d . . . C32 C 0.0971(3) 0.16201(15) 1.14876(18) 0.0883(9) Uani 1 1 d . . . H32A H 0.1705 0.1452 1.1438 0.132 Uiso 1 1 calc R . . H32B H 0.0607 0.1410 1.1980 0.132 Uiso 1 1 calc R . . H32C H 0.1035 0.2044 1.1647 0.132 Uiso 1 1 calc R . . C18 C 0.24880(18) 0.36403(9) 0.94747(16) 0.0545(5) Uani 1 1 d . . . C30 C 0.5766(2) 0.06770(11) 0.96850(17) 0.0664(6) Uani 1 1 d . . . H30A H 0.5135 0.0552 0.9268 0.100 Uiso 1 1 calc R . . H30B H 0.6238 0.0332 0.9839 0.100 Uiso 1 1 calc R . . H30C H 0.6185 0.0980 0.9369 0.100 Uiso 1 1 calc R . . C20 C 0.2616(2) 0.32903(11) 1.04292(17) 0.0684(7) Uani 1 1 d . . . H20A H 0.2002 0.3388 1.0806 0.103 Uiso 1 1 calc R . . H20B H 0.3309 0.3403 1.0774 0.103 Uiso 1 1 calc R . . H20C H 0.2618 0.2861 1.0303 0.103 Uiso 1 1 calc R . . C9 C 0.3537(2) 0.06147(10) 0.73625(18) 0.0659(6) Uani 1 1 d . . . H9A H 0.2993 0.0388 0.6969 0.099 Uiso 1 1 calc R . . H9B H 0.3256 0.0690 0.7977 0.099 Uiso 1 1 calc R . . H9C H 0.4221 0.0386 0.7446 0.099 Uiso 1 1 calc R . . C4 C 0.15281(19) 0.20757(10) 0.52594(14) 0.0552(5) Uani 1 1 d . . . C19 C 0.2583(2) 0.43176(11) 0.9731(2) 0.0851(9) Uani 1 1 d . . . H19A H 0.2491 0.4556 0.9156 0.128 Uiso 1 1 calc R . . H19B H 0.3306 0.4397 1.0050 0.128 Uiso 1 1 calc R . . H19C H 0.2010 0.4423 1.0147 0.128 Uiso 1 1 calc R . . C24 C -0.0284(2) 0.01936(11) 0.83186(19) 0.0665(6) Uani 1 1 d . . . H24 H -0.0226 -0.0192 0.8669 0.080 Uiso 1 1 calc R . . C29 C 0.62995(19) 0.11758(12) 1.12546(17) 0.0654(6) Uani 1 1 d . . . H29A H 0.6696 0.1488 1.0940 0.098 Uiso 1 1 calc R . . H29B H 0.6806 0.0851 1.1441 0.098 Uiso 1 1 calc R . . H29C H 0.5993 0.1342 1.1814 0.098 Uiso 1 1 calc R . . C22 C -0.1377(2) 0.43242(12) 0.8197(2) 0.0826(8) Uani 1 1 d . . . H22A H -0.1119 0.4676 0.8555 0.124 Uiso 1 1 calc R . . H22B H -0.2076 0.4190 0.8419 0.124 Uiso 1 1 calc R . . H22C H -0.1482 0.4426 0.7529 0.124 Uiso 1 1 calc R . . C25 C -0.1455(2) 0.04301(15) 0.8313(2) 0.0978(10) Uani 1 1 d . . . H25A H -0.1649 0.0487 0.8961 0.147 Uiso 1 1 calc R . . H25B H -0.1962 0.0144 0.7995 0.147 Uiso 1 1 calc R . . H25C H -0.1506 0.0812 0.7980 0.147 Uiso 1 1 calc R . . C21 C 0.3447(2) 0.34812(12) 0.8854(2) 0.0753(7) Uani 1 1 d . . . H21A H 0.3459 0.3050 0.8749 0.113 Uiso 1 1 calc R . . H21B H 0.4146 0.3607 0.9175 0.113 Uiso 1 1 calc R . . H21C H 0.3337 0.3687 0.8249 0.113 Uiso 1 1 calc R . . C8 C 0.44727(19) 0.16383(12) 0.75624(17) 0.0666(6) Uani 1 1 d . . . H8A H 0.5155 0.1434 0.7776 0.100 Uiso 1 1 calc R . . H8B H 0.4059 0.1734 0.8105 0.100 Uiso 1 1 calc R . . H8C H 0.4646 0.2006 0.7236 0.100 Uiso 1 1 calc R . . C33 C -0.0881(2) 0.17764(15) 1.0597(2) 0.0949(10) Uani 1 1 d . . . H33A H -0.0867 0.2204 1.0734 0.142 Uiso 1 1 calc R . . H33B H -0.1232 0.1564 1.1094 0.142 Uiso 1 1 calc R . . H33C H -0.1298 0.1707 0.9993 0.142 Uiso 1 1 calc R . . C11 C 0.1403(2) 0.22996(14) 0.42332(16) 0.0814(8) Uani 1 1 d . . . H11A H 0.0720 0.2527 0.4132 0.122 Uiso 1 1 calc R . . H11B H 0.1382 0.1958 0.3805 0.122 Uiso 1 1 calc R . . H11C H 0.2027 0.2555 0.4113 0.122 Uiso 1 1 calc R . . C10 C 0.4467(2) 0.10803(15) 0.60278(19) 0.0883(9) Uani 1 1 d . . . H10A H 0.5145 0.0877 0.6258 0.133 Uiso 1 1 calc R . . H10B H 0.4650 0.1452 0.5716 0.133 Uiso 1 1 calc R . . H10C H 0.4045 0.0823 0.5580 0.133 Uiso 1 1 calc R . . C26 C 0.0108(3) 0.0110(2) 0.7335(2) 0.1240(14) Uani 1 1 d . . . H26A H 0.0055 0.0489 0.6996 0.186 Uiso 1 1 calc R . . H26B H -0.0353 -0.0188 0.6993 0.186 Uiso 1 1 calc R . . H26C H 0.0872 -0.0026 0.7385 0.186 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 P 0.0307(2) 0.0331(2) 0.0420(3) 0.00244(19) 0.00065(19) 0.00402(18) S 0.0363(3) 0.0493(3) 0.0577(3) -0.0040(2) -0.0019(2) -0.0009(2) O3 0.0328(6) 0.0338(6) 0.0517(7) 0.0030(5) -0.0023(5) 0.0043(5) O1 0.0430(7) 0.0372(7) 0.0414(7) 0.0025(5) 0.0032(5) 0.0059(5) N1 0.0317(8) 0.0349(8) 0.0488(9) 0.0049(7) -0.0028(6) 0.0031(6) O6 0.0402(7) 0.0421(7) 0.0690(9) -0.0009(6) -0.0083(6) -0.0042(6) N2 0.0361(8) 0.0381(9) 0.0553(10) 0.0057(7) -0.0029(7) 0.0059(7) O2 0.0335(6) 0.0340(6) 0.0491(7) 0.0056(5) 0.0010(5) 0.0059(5) N3 0.0389(8) 0.0388(8) 0.0481(9) 0.0071(7) 0.0063(7) 0.0082(7) O4 0.0355(7) 0.0411(7) 0.0726(9) -0.0028(7) -0.0122(6) 0.0065(6) C23 0.0422(10) 0.0374(10) 0.0536(11) 0.0026(8) 0.0022(9) 0.0010(8) C17 0.0371(9) 0.0364(9) 0.0395(9) 0.0073(7) 0.0027(8) 0.0081(7) C6 0.0421(10) 0.0408(10) 0.0450(10) -0.0027(8) -0.0027(8) -0.0028(8) O5 0.0663(10) 0.0358(8) 0.1050(13) 0.0000(8) -0.0134(9) 0.0045(7) C27 0.0345(9) 0.0378(10) 0.0490(10) 0.0005(8) -0.0004(8) 0.0074(8) C1 0.0436(10) 0.0388(10) 0.0391(10) -0.0012(8) 0.0002(8) -0.0024(8) C12 0.0376(10) 0.0438(10) 0.0425(10) 0.0039(8) 0.0013(8) 0.0042(8) C16 0.0457(10) 0.0387(10) 0.0391(10) 0.0058(8) 0.0024(8) 0.0048(8) C15 0.0580(13) 0.0397(10) 0.0504(11) 0.0024(9) 0.0024(10) 0.0108(9) C2 0.0472(11) 0.0456(11) 0.0428(10) -0.0019(8) 0.0037(8) -0.0014(9) C13 0.0372(10) 0.0551(12) 0.0536(12) 0.0072(9) -0.0005(9) 0.0099(9) C14 0.0507(12) 0.0491(12) 0.0565(12) 0.0068(10) 0.0015(10) 0.0178(9) C3 0.0533(12) 0.0643(14) 0.0448(11) -0.0022(10) 0.0061(9) -0.0050(10) C5 0.0517(12) 0.0498(12) 0.0501(12) 0.0004(9) -0.0110(9) -0.0012(9) C31 0.0480(11) 0.0503(11) 0.0553(12) 0.0066(9) 0.0164(9) 0.0033(9) C28 0.0373(10) 0.0453(11) 0.0635(13) 0.0057(9) -0.0031(9) 0.0107(8) C7 0.0475(12) 0.0670(14) 0.0485(11) 0.0005(10) 0.0099(9) 0.0099(10) C32 0.102(2) 0.111(2) 0.0515(14) 0.0119(14) 0.0038(14) -0.0013(18) C18 0.0540(12) 0.0415(11) 0.0658(13) -0.0009(10) -0.0106(10) 0.0028(9) C30 0.0637(14) 0.0642(14) 0.0695(15) -0.0080(12) -0.0085(12) 0.0221(12) C20 0.0765(16) 0.0615(14) 0.0627(14) -0.0045(11) -0.0246(12) 0.0133(12) C9 0.0691(15) 0.0539(13) 0.0749(15) -0.0040(12) 0.0063(12) 0.0186(12) C4 0.0605(13) 0.0602(13) 0.0436(11) 0.0027(10) -0.0051(10) -0.0045(11) C19 0.0891(19) 0.0500(14) 0.110(2) -0.0076(14) -0.0338(17) -0.0028(13) C24 0.0630(14) 0.0510(13) 0.0829(17) -0.0018(12) -0.0126(12) -0.0192(11) C29 0.0482(12) 0.0780(16) 0.0677(14) -0.0090(12) -0.0114(11) 0.0167(11) C22 0.0694(16) 0.0682(16) 0.108(2) -0.0011(15) -0.0102(15) 0.0342(14) C25 0.0557(16) 0.111(2) 0.124(3) -0.007(2) -0.0155(16) -0.0260(16) C21 0.0503(14) 0.0735(16) 0.102(2) -0.0017(15) 0.0032(13) -0.0118(12) C8 0.0442(12) 0.0854(17) 0.0695(15) 0.0080(13) 0.0005(11) -0.0035(11) C33 0.0562(16) 0.118(3) 0.115(2) 0.0273(19) 0.0378(16) 0.0147(15) C11 0.0854(18) 0.107(2) 0.0502(13) 0.0163(14) -0.0040(12) 0.0013(16) C10 0.0759(18) 0.126(3) 0.0653(16) 0.0041(16) 0.0227(14) 0.0374(17) C26 0.113(3) 0.155(4) 0.103(3) -0.058(2) -0.001(2) -0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O1 1.6171(13) . ? P N3 1.6190(15) . ? P O3 1.6481(12) . ? P O2 1.6803(12) . ? P N1 1.8092(15) . ? S C12 1.7705(19) . ? S C6 1.776(2) . ? O3 C27 1.358(2) . ? O1 C1 1.391(2) . ? N1 C23 1.373(2) . ? N1 N2 1.416(2) . ? O6 C23 1.344(2) . ? O6 C24 1.448(2) . ? N2 C27 1.263(2) . ? O2 C17 1.379(2) . ? N3 C31 1.477(2) . ? O4 C27 1.322(2) . ? O4 C28 1.472(2) . ? C23 O5 1.199(2) . ? C17 C12 1.400(3) . ? C17 C16 1.410(3) . ? C6 C5 1.388(3) . ? C6 C1 1.389(3) . ? C1 C2 1.403(3) . ? C12 C13 1.388(3) . ? C16 C15 1.397(3) . ? C16 C18 1.533(3) . ? C15 C14 1.378(3) . ? C2 C3 1.398(3) . ? C2 C7 1.538(3) . ? C13 C14 1.379(3) . ? C14 C22 1.512(3) . ? C3 C4 1.386(3) . ? C5 C4 1.372(3) . ? C31 C33 1.500(3) . ? C31 C32 1.501(3) . ? C28 C30 1.488(3) . ? C28 C29 1.502(3) . ? C7 C10 1.535(3) . ? C7 C9 1.535(3) . ? C7 C8 1.535(3) . ? C18 C21 1.530(3) . ? C18 C19 1.535(3) . ? C18 C20 1.539(3) . ? C4 C11 1.514(3) . ? C24 C25 1.494(4) . ? C24 C26 1.498(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 O1 P N3 134.63(8) . . ? O1 P O3 108.84(7) . . ? N3 P O3 116.34(8) . . ? O1 P O2 92.31(6) . . ? N3 P O2 93.94(7) . . ? O3 P O2 86.98(6) . . ? O1 P N1 85.88(7) . . ? N3 P N1 93.07(7) . . ? O3 P N1 85.97(6) . . ? O2 P N1 171.72(7) . . ? C12 S C6 100.61(9) . . ? C27 O3 P 113.49(11) . . ? C1 O1 P 133.01(11) . . ? C23 N1 N2 114.81(14) . . ? C23 N1 P 125.72(12) . . ? N2 N1 P 113.15(11) . . ? C23 O6 C24 117.97(16) . . ? C27 N2 N1 106.01(14) . . ? C17 O2 P 131.71(11) . . ? C31 N3 P 133.22(13) . . ? C27 O4 C28 116.88(14) . . ? O5 C23 O6 124.68(18) . . ? O5 C23 N1 126.24(18) . . ? O6 C23 N1 108.99(15) . . ? O2 C17 C12 120.08(16) . . ? O2 C17 C16 119.33(16) . . ? C12 C17 C16 120.47(16) . . ? C5 C6 C1 119.93(18) . . ? C5 C6 S 119.23(15) . . ? C1 C6 S 120.78(14) . . ? N2 C27 O4 128.28(16) . . ? N2 C27 O3 120.97(16) . . ? O4 C27 O3 110.74(15) . . ? C6 C1 O1 120.16(16) . . ? C6 C1 C2 121.61(17) . . ? O1 C1 C2 117.89(16) . . ? C13 C12 C17 120.22(18) . . ? C13 C12 S 118.11(15) . . ? C17 C12 S 121.66(14) . . ? C15 C16 C17 116.25(17) . . ? C15 C16 C18 121.07(17) . . ? C17 C16 C18 122.67(16) . . ? C14 C15 C16 124.11(19) . . ? C3 C2 C1 115.46(18) . . ? C3 C2 C7 121.06(18) . . ? C1 C2 C7 123.47(17) . . ? C14 C13 C12 120.66(19) . . ? C15 C14 C13 118.21(18) . . ? C15 C14 C22 121.0(2) . . ? C13 C14 C22 120.7(2) . . ? C4 C3 C2 124.2(2) . . ? C4 C5 C6 120.74(19) . . ? N3 C31 C33 107.99(18) . . ? N3 C31 C32 110.84(19) . . ? C33 C31 C32 111.8(2) . . ? O4 C28 C30 108.97(17) . . ? O4 C28 C29 105.41(16) . . ? C30 C28 C29 113.06(18) . . ? C10 C7 C9 106.9(2) . . ? C10 C7 C8 107.3(2) . . ? C9 C7 C8 110.42(19) . . ? C10 C7 C2 111.43(18) . . ? C9 C7 C2 111.77(18) . . ? C8 C7 C2 108.92(18) . . ? C21 C18 C16 110.66(18) . . ? C21 C18 C19 108.0(2) . . ? C16 C18 C19 111.91(18) . . ? C21 C18 C20 110.30(19) . . ? C16 C18 C20 109.46(18) . . ? C19 C18 C20 106.4(2) . . ? C5 C4 C3 118.03(19) . . ? C5 C4 C11 121.3(2) . . ? C3 C4 C11 120.7(2) . . ? O6 C24 C25 105.8(2) . . ? O6 C24 C26 108.6(2) . . ? C25 C24 C26 113.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.045 #===END data_compd16 _database_code_depnum_ccdc_archive 'CCDC 280921' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 Cl N2 O6 P S' _chemical_formula_weight 625.14 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M p_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4788(7) _cell_length_b 10.8660(7) _cell_length_c 16.3413(11) _cell_angle_alpha 92.5670(10) _cell_angle_beta 103.1120(10) _cell_angle_gamma 111.9970(10) _cell_volume 1662.80(19) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'THICK NEEDLES' _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type 'EMPIRICAL, SADABS' _exptl_absorpt_correction_T_min 0.9240 _exptl_absorpt_correction_T_max 0.9484 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16112 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0469 _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 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5836 _reflns_number_gt 4167 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0637P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5836 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.008 _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 P P 0.57776(6) 0.66016(6) 0.27176(3) 0.04043(16) Uani 1 1 d . . . S S 0.51147(6) 0.54219(6) 0.38032(3) 0.04812(17) Uani 1 1 d . . . Cl Cl 0.77385(6) 0.61959(7) 0.30976(4) 0.06001(19) Uani 1 1 d . . . O1 O 0.42690(14) 0.68551(13) 0.25266(9) 0.0420(3) Uani 1 1 d . . . O2 O 0.49516(15) 0.51286(14) 0.20788(8) 0.0450(4) Uani 1 1 d . . . O3 O 0.62829(15) 0.73530(14) 0.19100(8) 0.0441(4) Uani 1 1 d . . . O6 O 0.77955(16) 0.97193(16) 0.45234(9) 0.0566(4) Uani 1 1 d . . . O5 O 0.58201(17) 0.78908(15) 0.44863(9) 0.0538(4) Uani 1 1 d . . . N1 N 0.67511(18) 0.81836(17) 0.33604(10) 0.0441(4) Uani 1 1 d . . . O4 O 0.79385(17) 0.90904(16) 0.15910(10) 0.0584(4) Uani 1 1 d . . . C17 C 0.4885(2) 0.3954(2) 0.23855(13) 0.0442(5) Uani 1 1 d . . . N2 N 0.76959(19) 0.91020(18) 0.29633(11) 0.0500(5) Uani 1 1 d . . . C23 C 0.6734(2) 0.8555(2) 0.41569(13) 0.0439(5) Uani 1 1 d . . . C12 C 0.4949(2) 0.3924(2) 0.32410(13) 0.0454(5) Uani 1 1 d . . . C1 C 0.3125(2) 0.6054(2) 0.27930(13) 0.0423(5) Uani 1 1 d . . . C16 C 0.4785(2) 0.2854(2) 0.18682(14) 0.0446(5) Uani 1 1 d . . . C2 C 0.1759(2) 0.5982(2) 0.24122(14) 0.0461(5) Uani 1 1 d . . . C15 C 0.4848(2) 0.1776(2) 0.22922(15) 0.0524(6) Uani 1 1 d . . . H10 H 0.4782 0.1016 0.1971 0.063 Uiso 1 1 calc R . . C27 C 0.7344(2) 0.8568(2) 0.21937(14) 0.0461(5) Uani 1 1 d . . . C6 C 0.3353(2) 0.5345(2) 0.34536(13) 0.0457(5) Uani 1 1 d . . . C18 C 0.4646(3) 0.2825(2) 0.09127(14) 0.0508(6) Uani 1 1 d . . . C3 C 0.0692(3) 0.5223(2) 0.27770(16) 0.0588(6) Uani 1 1 d . . . H3 H -0.0228 0.5167 0.2548 0.071 Uiso 1 1 calc R . . C13 C 0.5030(2) 0.2846(2) 0.36388(15) 0.0533(6) Uani 1 1 d . . . H8 H 0.5102 0.2856 0.4217 0.064 Uiso 1 1 calc R . . C7 C 0.1441(2) 0.6648(2) 0.16271(15) 0.0524(6) Uani 1 1 d . . . C5 C 0.2259(3) 0.4586(2) 0.37905(16) 0.0609(7) Uani 1 1 d . . . H5 H 0.2434 0.4112 0.4233 0.073 Uiso 1 1 calc R . . C4 C 0.0916(3) 0.4541(3) 0.34631(18) 0.0659(7) Uani 1 1 d . . . C14 C 0.5001(3) 0.1762(2) 0.31581(15) 0.0536(6) Uani 1 1 d . . . C19 C 0.4438(3) 0.1460(3) 0.04847(16) 0.0752(8) Uani 1 1 d . . . H20A H 0.4344 0.1481 -0.0112 0.113 Uiso 1 1 calc R . . H20B H 0.3591 0.0783 0.0568 0.113 Uiso 1 1 calc R . . H20C H 0.5247 0.1257 0.0730 0.113 Uiso 1 1 calc R . . C28 C 0.9012(3) 1.0467(3) 0.18154(17) 0.0678(7) Uani 1 1 d . . . H26 H 0.9518 1.0621 0.2418 0.081 Uiso 1 1 calc R . . C24 C 0.7843(3) 1.0184(3) 0.53881(15) 0.0664(7) Uani 1 1 d . . . H23 H 0.6866 0.9958 0.5433 0.080 Uiso 1 1 calc R . . C21 C 0.3338(3) 0.3109(3) 0.04855(15) 0.0678(7) Uani 1 1 d . . . H22A H 0.3432 0.3962 0.0741 0.102 Uiso 1 1 calc R . . H22B H 0.2491 0.2418 0.0558 0.102 Uiso 1 1 calc R . . H22C H 0.3274 0.3123 -0.0109 0.102 Uiso 1 1 calc R . . C8 C 0.1841(3) 0.6059(3) 0.09047(17) 0.0823(9) Uani 1 1 d . . . H14A H 0.1636 0.6462 0.0407 0.123 Uiso 1 1 calc R . . H14B H 0.1297 0.5107 0.0783 0.123 Uiso 1 1 calc R . . H14C H 0.2840 0.6237 0.1070 0.123 Uiso 1 1 calc R . . C30 C 0.8311(4) 1.1401(3) 0.1660(3) 0.1220(14) Uani 1 1 d . . . H28A H 0.7939 1.1347 0.1060 0.183 Uiso 1 1 calc R . . H28B H 0.8989 1.2297 0.1889 0.183 Uiso 1 1 calc R . . H28C H 0.7545 1.1172 0.1930 0.183 Uiso 1 1 calc R . . C26 C 0.8611(4) 1.1680(3) 0.5512(2) 0.1235(15) Uani 1 1 d . . . H25A H 0.9552 1.1908 0.5439 0.185 Uiso 1 1 calc R . . H25B H 0.8676 1.2043 0.6073 0.185 Uiso 1 1 calc R . . H25C H 0.8095 1.2047 0.5101 0.185 Uiso 1 1 calc R . . C20 C 0.6000(3) 0.3873(3) 0.07719(18) 0.0758(8) Uani 1 1 d . . . H21A H 0.6112 0.4749 0.0998 0.114 Uiso 1 1 calc R . . H21B H 0.5931 0.3835 0.0175 0.114 Uiso 1 1 calc R . . H21C H 0.6809 0.3696 0.1054 0.114 Uiso 1 1 calc R . . C9 C 0.2298(3) 0.8162(3) 0.1816(2) 0.0807(9) Uani 1 1 d . . . H15A H 0.3298 0.8346 0.1989 0.121 Uiso 1 1 calc R . . H15B H 0.2036 0.8534 0.2264 0.121 Uiso 1 1 calc R . . H15C H 0.2099 0.8560 0.1316 0.121 Uiso 1 1 calc R . . C22 C 0.5175(3) 0.0591(3) 0.35594(18) 0.0773(8) Uani 1 1 d . . . H18A H 0.5489 0.0826 0.4166 0.116 Uiso 1 1 calc R . . H18B H 0.5869 0.0370 0.3362 0.116 Uiso 1 1 calc R . . H18C H 0.4277 -0.0169 0.3406 0.116 Uiso 1 1 calc R . . C29 C 1.0023(4) 1.0552(4) 0.1291(3) 0.1428(18) Uani 1 1 d . . . H27A H 0.9537 1.0431 0.0701 0.214 Uiso 1 1 calc R . . H27B H 1.0383 0.9864 0.1392 0.214 Uiso 1 1 calc R . . H27C H 1.0803 1.1415 0.1440 0.214 Uiso 1 1 calc R . . C11 C -0.0321(3) 0.3751(3) 0.3824(2) 0.1044(12) Uani 1 1 d . . . H17A H -0.0219 0.2952 0.3996 0.157 Uiso 1 1 calc R . . H17B H -0.1205 0.3511 0.3397 0.157 Uiso 1 1 calc R . . H17C H -0.0319 0.4292 0.4306 0.157 Uiso 1 1 calc R . . C10 C -0.0131(3) 0.6400(3) 0.13196(19) 0.0859(9) Uani 1 1 d . . . H16A H -0.0277 0.6837 0.0830 0.129 Uiso 1 1 calc R . . H16B H -0.0418 0.6753 0.1763 0.129 Uiso 1 1 calc R . . H16C H -0.0691 0.5453 0.1172 0.129 Uiso 1 1 calc R . . C25 C 0.8542(4) 0.9514(4) 0.60045(18) 0.1052(12) Uani 1 1 d . . . H24A H 0.8033 0.8560 0.5867 0.158 Uiso 1 1 calc R . . H24B H 0.8534 0.9798 0.6568 0.158 Uiso 1 1 calc R . . H24C H 0.9509 0.9754 0.5977 0.158 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 P 0.0411(3) 0.0460(3) 0.0344(3) 0.0047(2) 0.0106(2) 0.0171(3) S 0.0602(4) 0.0529(4) 0.0363(3) 0.0078(3) 0.0141(3) 0.0268(3) Cl 0.0514(4) 0.0776(4) 0.0603(4) 0.0111(3) 0.0148(3) 0.0354(3) O1 0.0380(8) 0.0436(8) 0.0447(8) 0.0109(7) 0.0133(6) 0.0144(7) O2 0.0580(9) 0.0422(8) 0.0338(8) 0.0064(6) 0.0105(7) 0.0193(7) O3 0.0443(8) 0.0482(9) 0.0358(8) 0.0036(7) 0.0119(7) 0.0134(7) O6 0.0511(10) 0.0600(10) 0.0402(9) -0.0055(8) 0.0098(7) 0.0044(8) O5 0.0557(10) 0.0549(10) 0.0453(9) 0.0017(8) 0.0205(8) 0.0122(8) N1 0.0431(10) 0.0468(11) 0.0368(10) 0.0029(8) 0.0136(8) 0.0100(9) O4 0.0597(10) 0.0594(10) 0.0483(9) 0.0088(8) 0.0254(8) 0.0084(8) C17 0.0462(13) 0.0438(13) 0.0440(13) 0.0090(10) 0.0117(10) 0.0190(11) N2 0.0449(11) 0.0553(12) 0.0422(11) 0.0056(9) 0.0142(9) 0.0100(9) C23 0.0416(12) 0.0485(13) 0.0378(12) 0.0027(10) 0.0076(10) 0.0159(11) C12 0.0569(14) 0.0472(13) 0.0392(12) 0.0093(10) 0.0160(10) 0.0261(11) C1 0.0439(12) 0.0409(12) 0.0425(12) 0.0018(10) 0.0172(10) 0.0142(10) C16 0.0440(12) 0.0442(13) 0.0462(13) 0.0064(10) 0.0133(10) 0.0172(10) C2 0.0444(13) 0.0438(13) 0.0512(13) -0.0004(10) 0.0188(11) 0.0157(11) C15 0.0583(15) 0.0470(14) 0.0580(15) 0.0071(11) 0.0199(12) 0.0249(12) C27 0.0410(12) 0.0536(14) 0.0412(13) 0.0067(11) 0.0125(10) 0.0151(11) C6 0.0521(13) 0.0476(13) 0.0420(12) 0.0049(10) 0.0206(11) 0.0200(11) C18 0.0619(15) 0.0483(14) 0.0426(13) 0.0038(10) 0.0182(11) 0.0198(12) C3 0.0477(14) 0.0607(16) 0.0718(17) 0.0033(13) 0.0273(13) 0.0198(12) C13 0.0617(15) 0.0616(16) 0.0458(13) 0.0163(12) 0.0181(12) 0.0311(13) C7 0.0408(12) 0.0625(15) 0.0528(14) 0.0061(12) 0.0105(11) 0.0203(12) C5 0.0786(19) 0.0555(16) 0.0618(16) 0.0162(12) 0.0380(15) 0.0289(14) C4 0.0673(18) 0.0607(17) 0.0796(19) 0.0139(14) 0.0452(15) 0.0207(14) C14 0.0622(15) 0.0538(15) 0.0556(15) 0.0164(12) 0.0191(12) 0.0317(12) C19 0.107(2) 0.0650(17) 0.0557(16) 0.0007(13) 0.0205(16) 0.0380(17) C28 0.0529(15) 0.0755(19) 0.0591(16) 0.0190(14) 0.0162(13) 0.0062(14) C24 0.0649(16) 0.0723(18) 0.0418(14) -0.0095(13) 0.0149(12) 0.0064(14) C21 0.0809(19) 0.0774(18) 0.0456(14) 0.0079(13) 0.0111(13) 0.0352(16) C8 0.0739(19) 0.126(3) 0.0519(16) 0.0036(17) 0.0142(14) 0.0479(19) C30 0.126(3) 0.070(2) 0.162(4) 0.011(2) 0.029(3) 0.035(2) C26 0.151(4) 0.079(2) 0.077(2) -0.0262(18) 0.039(2) -0.024(2) C20 0.083(2) 0.0780(19) 0.0664(17) 0.0078(15) 0.0424(16) 0.0192(16) C9 0.0768(19) 0.0700(19) 0.094(2) 0.0262(16) 0.0096(17) 0.0333(16) C22 0.107(2) 0.0740(19) 0.0741(19) 0.0296(15) 0.0308(17) 0.0555(18) C29 0.126(3) 0.112(3) 0.214(5) 0.046(3) 0.120(4) 0.026(3) C11 0.093(2) 0.110(3) 0.134(3) 0.046(2) 0.082(2) 0.033(2) C10 0.0526(16) 0.123(3) 0.084(2) 0.0179(19) 0.0128(15) 0.0395(17) C25 0.094(2) 0.160(3) 0.0480(17) 0.011(2) -0.0030(16) 0.047(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O3 1.6668(14) . ? P O1 1.6681(14) . ? P O2 1.6743(14) . ? P N1 1.7713(17) . ? P Cl 2.2194(8) . ? P S 2.3170(8) . ? S C12 1.762(2) . ? S C6 1.773(2) . ? O1 C1 1.369(2) . ? O2 C17 1.376(2) . ? O3 C27 1.344(2) . ? O6 C23 1.331(2) . ? O6 C24 1.462(3) . ? O5 C23 1.216(2) . ? N1 C23 1.352(3) . ? N1 N2 1.416(2) . ? O4 C27 1.320(3) . ? O4 C28 1.463(3) . ? C17 C12 1.387(3) . ? C17 C16 1.389(3) . ? N2 C27 1.272(3) . ? C12 C13 1.385(3) . ? C1 C6 1.383(3) . ? C1 C2 1.396(3) . ? C16 C15 1.402(3) . ? C16 C18 1.533(3) . ? C2 C3 1.393(3) . ? C2 C7 1.533(3) . ? C15 C14 1.389(3) . ? C6 C5 1.385(3) . ? C18 C20 1.524(3) . ? C18 C19 1.528(3) . ? C18 C21 1.537(3) . ? C3 C4 1.395(4) . ? C13 C14 1.373(3) . ? C7 C10 1.523(3) . ? C7 C9 1.527(3) . ? C7 C8 1.528(3) . ? C5 C4 1.369(4) . ? C4 C11 1.524(3) . ? C14 C22 1.509(3) . ? C28 C30 1.459(4) . ? C28 C29 1.488(4) . ? C24 C25 1.486(4) . ? C24 C26 1.500(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 O3 P O1 93.70(7) . . ? O3 P O2 89.91(7) . . ? O1 P O2 91.03(7) . . ? O3 P N1 87.14(7) . . ? O1 P N1 91.83(8) . . ? O2 P N1 176.02(8) . . ? O3 P Cl 92.18(6) . . ? O1 P Cl 174.03(6) . . ? O2 P Cl 90.00(6) . . ? N1 P Cl 87.44(6) . . ? O3 P S 175.59(6) . . ? O1 P S 89.24(5) . . ? O2 P S 86.75(5) . . ? N1 P S 96.06(6) . . ? Cl P S 84.95(3) . . ? C12 S C6 101.13(10) . . ? C12 S P 91.01(7) . . ? C6 S P 91.32(7) . . ? C1 O1 P 121.18(13) . . ? C17 O2 P 120.90(12) . . ? C27 O3 P 110.69(13) . . ? C23 O6 C24 115.86(18) . . ? C23 N1 N2 119.54(17) . . ? C23 N1 P 128.31(15) . . ? N2 N1 P 112.06(13) . . ? C27 O4 C28 116.32(18) . . ? O2 C17 C12 116.93(19) . . ? O2 C17 C16 121.73(19) . . ? C12 C17 C16 121.3(2) . . ? C27 N2 N1 105.86(17) . . ? O5 C23 O6 124.57(19) . . ? O5 C23 N1 122.5(2) . . ? O6 C23 N1 112.90(19) . . ? C13 C12 C17 122.1(2) . . ? C13 C12 S 122.53(17) . . ? C17 C12 S 115.04(16) . . ? O1 C1 C6 118.82(19) . . ? O1 C1 C2 120.20(19) . . ? C6 C1 C2 121.0(2) . . ? C17 C16 C15 114.7(2) . . ? C17 C16 C18 122.89(19) . . ? C15 C16 C18 122.4(2) . . ? C3 C2 C1 115.4(2) . . ? C3 C2 C7 122.1(2) . . ? C1 C2 C7 122.45(19) . . ? C14 C15 C16 124.7(2) . . ? N2 C27 O4 126.3(2) . . ? N2 C27 O3 121.5(2) . . ? O4 C27 O3 112.20(18) . . ? C1 C6 C5 121.8(2) . . ? C1 C6 S 115.43(16) . . ? C5 C6 S 122.73(19) . . ? C20 C18 C19 108.1(2) . . ? C20 C18 C16 109.2(2) . . ? C19 C18 C16 112.10(19) . . ? C20 C18 C21 110.5(2) . . ? C19 C18 C21 107.2(2) . . ? C16 C18 C21 109.68(18) . . ? C2 C3 C4 124.3(2) . . ? C14 C13 C12 118.3(2) . . ? C10 C7 C9 107.9(2) . . ? C10 C7 C8 107.5(2) . . ? C9 C7 C8 109.5(2) . . ? C10 C7 C2 112.5(2) . . ? C9 C7 C2 110.66(19) . . ? C8 C7 C2 108.7(2) . . ? C4 C5 C6 119.1(2) . . ? C5 C4 C3 118.4(2) . . ? C5 C4 C11 121.4(3) . . ? C3 C4 C11 120.2(3) . . ? C13 C14 C15 118.7(2) . . ? C13 C14 C22 121.1(2) . . ? C15 C14 C22 120.2(2) . . ? C30 C28 O4 109.4(2) . . ? C30 C28 C29 114.1(3) . . ? O4 C28 C29 105.1(2) . . ? O6 C24 C25 110.1(2) . . ? O6 C24 C26 105.8(2) . . ? C25 C24 C26 113.8(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.321 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.043 #===END data_compd17 _database_code_depnum_ccdc_archive 'CCDC 280922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H50 N3 O6 P S' _chemical_formula_weight 707.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p_21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.274(2) _cell_length_b 17.798(3) _cell_length_c 24.057(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.367(15) _cell_angle_gamma 90.00 _cell_volume 3946.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9670 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6872 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0885 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 24.98 _reflns_number_total 6872 _reflns_number_gt 2968 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0856P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6872 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1382 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.08504(12) 0.14292(6) 0.14830(5) 0.0409(3) Uani 1 d . . . P P -0.13986(12) 0.12323(6) 0.20426(5) 0.0360(3) Uani 1 d . . . O1 O -0.2290(3) 0.15534(16) 0.14326(12) 0.0393(7) Uani 1 d . . . O2 O -0.1419(3) 0.03666(16) 0.17769(11) 0.0391(7) Uani 1 d . . . O3 O -0.1000(3) 0.21491(15) 0.22166(12) 0.0387(7) Uani 1 d . . . N1 N 0.0001(4) 0.10150(19) 0.25934(14) 0.0373(9) Uani 1 d . . . N2 N 0.0895(4) 0.1641(2) 0.27807(15) 0.0432(9) Uani 1 d . . . C12 C 0.0518(4) 0.0520(2) 0.11971(17) 0.0364(10) Uani 1 d . . . O5 O -0.0718(4) -0.01408(19) 0.28665(13) 0.0597(10) Uani 1 d . . . O6 O 0.1163(4) 0.0453(2) 0.33477(14) 0.0660(11) Uani 1 d . . . O4 O 0.0736(3) 0.29193(18) 0.26057(14) 0.0578(9) Uani 1 d . . . C2 C -0.2695(5) 0.2490(2) 0.07115(18) 0.0390(10) Uani 1 d . . . C8 C -0.0976(5) -0.0605(2) 0.11286(18) 0.0415(11) Uani 1 d . . . C6 C -0.0254(4) 0.2010(2) 0.10080(17) 0.0360(10) Uani 1 d . . . C33 C 0.0081(5) 0.0386(3) 0.29330(19) 0.0428(11) Uani 1 d . . . C11 C 0.1385(5) 0.0242(3) 0.08125(18) 0.0454(12) Uani 1 d . . . H11 H 0.2155 0.0527 0.0712 0.054 Uiso 1 calc R . . C5 C 0.0338(5) 0.2460(3) 0.06202(19) 0.0482(12) Uani 1 d . . . H5 H 0.1332 0.2454 0.0597 0.058 Uiso 1 calc R . . C1 C -0.1741(5) 0.2027(2) 0.10615(16) 0.0360(10) Uani 1 d . . . C10 C 0.1110(5) -0.0453(3) 0.05799(19) 0.0494(12) Uani 1 d . . . C23 C -0.3021(5) 0.1140(2) 0.23993(18) 0.0389(10) Uani 1 d . . . C24 C -0.2958(6) 0.1368(3) 0.2955(2) 0.0564(14) Uani 1 d . . . H24 H -0.2087 0.1542 0.3139 0.068 Uiso 1 calc R . . C7 C -0.0631(4) 0.0105(2) 0.13720(17) 0.0355(10) Uani 1 d . . . C29 C 0.0237(5) 0.2213(3) 0.25568(19) 0.0417(11) Uani 1 d . . . C18 C -0.2313(5) -0.1062(3) 0.1248(2) 0.0538(13) Uani 1 d . . . C26 C -0.5483(6) 0.1088(3) 0.2968(3) 0.0697(17) Uani 1 d . . . H26 H -0.6302 0.1074 0.3159 0.084 Uiso 1 calc R . . C13 C -0.4342(5) 0.2504(3) 0.0750(2) 0.0483(12) Uani 1 d . . . C9 C -0.0066(5) -0.0857(3) 0.07356(19) 0.0476(12) Uani 1 d . . . H9 H -0.0264 -0.1323 0.0570 0.057 Uiso 1 calc R . . C19 C -0.2322(7) -0.1226(3) 0.1861(2) 0.084(2) Uani 1 d . . . H19A H -0.1471 -0.1509 0.1994 0.127 Uiso 1 calc R . . H19B H -0.3171 -0.1513 0.1917 0.127 Uiso 1 calc R . . H19C H -0.2330 -0.0763 0.2065 0.127 Uiso 1 calc R . . C14 C -0.4990(5) 0.1723(3) 0.0607(2) 0.0611(14) Uani 1 d . . . H14A H -0.4866 0.1600 0.0227 0.092 Uiso 1 calc R . . H14B H -0.6005 0.1726 0.0653 0.092 Uiso 1 calc R . . H14C H -0.4504 0.1355 0.0853 0.092 Uiso 1 calc R . . C3 C -0.2041(5) 0.2921(3) 0.03246(18) 0.0454(11) Uani 1 d . . . H3 H -0.2636 0.3233 0.0088 0.054 Uiso 1 calc R . . C30 C 0.2183(6) 0.3029(3) 0.2911(3) 0.0732(17) Uani 1 d . . . H30 H 0.2903 0.2703 0.2765 0.088 Uiso 1 calc R . . C15 C -0.5116(6) 0.3069(3) 0.0328(2) 0.0741(17) Uani 1 d . . . H15A H -0.4673 0.3555 0.0384 0.111 Uiso 1 calc R . . H15B H -0.6123 0.3102 0.0385 0.111 Uiso 1 calc R . . H15C H -0.5033 0.2902 -0.0046 0.111 Uiso 1 calc R . . C16 C -0.4661(6) 0.2742(3) 0.1340(2) 0.0652(15) Uani 1 d . . . H16A H -0.4162 0.2412 0.1613 0.098 Uiso 1 calc R . . H16B H -0.5686 0.2714 0.1364 0.098 Uiso 1 calc R . . H16C H -0.4334 0.3248 0.1411 0.098 Uiso 1 calc R . . C28 C -0.4334(5) 0.0884(3) 0.2139(2) 0.0497(12) Uani 1 d . . . H28 H -0.4392 0.0723 0.1769 0.060 Uiso 1 calc R . . C27 C -0.5566(5) 0.0860(3) 0.2417(3) 0.0632(15) Uani 1 d . . . H27 H -0.6442 0.0692 0.2234 0.076 Uiso 1 calc R . . C34 C 0.1206(6) -0.0077(3) 0.3806(2) 0.0623(16) Uani 1 d . . . H34 H 0.0474 -0.0470 0.3723 0.075 Uiso 1 calc R . . C4 C -0.0559(5) 0.2920(3) 0.02667(19) 0.0478(12) Uani 1 d . . . C17 C 0.0035(6) 0.3430(3) -0.0156(2) 0.0746(18) Uani 1 d . . . H17A H 0.1051 0.3332 -0.0163 0.112 Uiso 1 calc R . . H17B H -0.0100 0.3945 -0.0054 0.112 Uiso 1 calc R . . H17C H -0.0469 0.3337 -0.0520 0.112 Uiso 1 calc R . . C22 C 0.2043(6) -0.0785(3) 0.0165(2) 0.0665(16) Uani 1 d . . . H22A H 0.1969 -0.1323 0.0170 0.100 Uiso 1 calc R . . H22B H 0.3035 -0.0639 0.0264 0.100 Uiso 1 calc R . . H22C H 0.1717 -0.0603 -0.0204 0.100 Uiso 1 calc R . . C25 C -0.4179(6) 0.1337(3) 0.3234(2) 0.0688(16) Uani 1 d . . . H25 H -0.4120 0.1487 0.3607 0.083 Uiso 1 calc R . . C20 C -0.3693(6) -0.0606(3) 0.1017(3) 0.085(2) Uani 1 d . . . H20A H -0.3622 -0.0103 0.1161 0.128 Uiso 1 calc R . . H20B H -0.4541 -0.0844 0.1131 0.128 Uiso 1 calc R . . H20C H -0.3763 -0.0592 0.0616 0.128 Uiso 1 calc R . . C21 C -0.2419(7) -0.1825(3) 0.0937(3) 0.0808(19) Uani 1 d . . . H21A H -0.2467 -0.1738 0.0541 0.121 Uiso 1 calc R . . H21B H -0.3277 -0.2085 0.1019 0.121 Uiso 1 calc R . . H21C H -0.1580 -0.2123 0.1057 0.121 Uiso 1 calc R . . C35 C 0.0909(11) 0.0360(5) 0.4309(3) 0.156(4) Uani 1 d . . . H35A H 0.1567 0.0777 0.4359 0.233 Uiso 1 calc R . . H35B H 0.1040 0.0042 0.4633 0.233 Uiso 1 calc R . . H35C H -0.0071 0.0543 0.4259 0.233 Uiso 1 calc R . . C31 C 0.2113(9) 0.2891(5) 0.3542(4) 0.148(4) Uani 1 d . . . H31A H 0.1401 0.3218 0.3674 0.222 Uiso 1 calc R . . H31B H 0.3045 0.2991 0.3744 0.222 Uiso 1 calc R . . H31C H 0.1848 0.2378 0.3600 0.222 Uiso 1 calc R . . C32 C 0.2534(10) 0.3833(5) 0.2838(4) 0.186(6) Uani 1 d . . . H32A H 0.1763 0.4138 0.2949 0.280 Uiso 1 calc R . . H32B H 0.2646 0.3928 0.2452 0.280 Uiso 1 calc R . . H32C H 0.3421 0.3953 0.3065 0.280 Uiso 1 calc R . . C36 C 0.2703(8) -0.0411(5) 0.3876(4) 0.155(4) Uani 1 d . . . H36A H 0.2849 -0.0700 0.3551 0.232 Uiso 1 calc R . . H36B H 0.2806 -0.0730 0.4200 0.232 Uiso 1 calc R . . H36C H 0.3409 -0.0015 0.3923 0.232 Uiso 1 calc R . . N3 N 0.8022(10) 0.4845(5) 0.0727(3) 0.143(3) Uani 1 d . . . C37 C 0.8314(8) 0.4557(4) 0.1141(4) 0.095(2) Uani 1 d . . . C38 C 0.8660(8) 0.4171(4) 0.1666(3) 0.098(2) Uani 1 d . . . H38A H 0.8977 0.3670 0.1596 0.146 Uiso 1 calc R . . H38B H 0.7815 0.4151 0.1862 0.146 Uiso 1 calc R . . H38C H 0.9421 0.4436 0.1888 0.146 Uiso 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 S 0.0373(6) 0.0411(7) 0.0434(7) 0.0015(5) 0.0014(5) -0.0007(5) P 0.0336(6) 0.0375(7) 0.0364(6) -0.0013(5) 0.0014(5) -0.0014(5) O1 0.0309(16) 0.0469(18) 0.0391(17) 0.0060(14) 0.0000(13) -0.0033(13) O2 0.0418(17) 0.0383(17) 0.0375(17) -0.0078(14) 0.0066(14) -0.0046(14) O3 0.0338(16) 0.0345(17) 0.0470(18) -0.0065(14) 0.0008(14) -0.0030(13) N1 0.036(2) 0.037(2) 0.037(2) -0.0013(17) -0.0010(16) -0.0075(16) N2 0.044(2) 0.039(2) 0.045(2) -0.0015(18) -0.0035(18) -0.0080(18) C12 0.038(2) 0.034(2) 0.036(2) -0.0028(19) -0.001(2) 0.002(2) O5 0.070(2) 0.056(2) 0.049(2) 0.0122(17) -0.0100(18) -0.0234(19) O6 0.066(2) 0.070(2) 0.056(2) 0.0259(19) -0.0196(18) -0.025(2) O4 0.055(2) 0.041(2) 0.074(2) -0.0079(17) -0.0073(18) -0.0092(17) C2 0.039(3) 0.037(3) 0.040(2) -0.003(2) 0.003(2) 0.001(2) C8 0.041(3) 0.043(3) 0.038(3) -0.002(2) -0.006(2) 0.004(2) C6 0.034(2) 0.036(2) 0.039(2) 0.002(2) 0.0062(19) -0.0070(19) C33 0.035(3) 0.051(3) 0.042(3) 0.000(2) 0.000(2) -0.008(2) C11 0.040(3) 0.053(3) 0.044(3) 0.008(2) 0.008(2) 0.007(2) C5 0.037(3) 0.053(3) 0.056(3) 0.000(2) 0.008(2) -0.004(2) C1 0.046(3) 0.032(2) 0.030(2) -0.0006(19) 0.003(2) -0.008(2) C10 0.055(3) 0.054(3) 0.038(3) 0.001(2) 0.002(2) 0.019(3) C23 0.037(3) 0.037(3) 0.043(3) -0.001(2) 0.007(2) -0.003(2) C24 0.057(3) 0.061(3) 0.052(3) -0.013(3) 0.013(3) -0.009(3) C7 0.037(2) 0.039(2) 0.030(2) 0.0019(19) 0.0000(19) 0.004(2) C29 0.037(3) 0.042(3) 0.045(3) -0.010(2) 0.001(2) -0.007(2) C18 0.058(3) 0.048(3) 0.054(3) -0.013(2) -0.002(3) -0.008(2) C26 0.054(4) 0.065(4) 0.098(5) 0.022(3) 0.043(3) 0.006(3) C13 0.043(3) 0.045(3) 0.058(3) 0.004(2) 0.005(2) 0.003(2) C9 0.054(3) 0.040(3) 0.045(3) -0.003(2) -0.008(2) 0.010(2) C19 0.107(5) 0.084(5) 0.062(4) -0.003(3) 0.009(4) -0.048(4) C14 0.043(3) 0.063(4) 0.076(4) -0.001(3) -0.003(3) -0.005(3) C3 0.051(3) 0.041(3) 0.043(3) 0.005(2) -0.001(2) 0.003(2) C30 0.061(4) 0.068(4) 0.085(4) -0.014(3) -0.018(3) -0.019(3) C15 0.054(3) 0.082(4) 0.084(4) 0.028(3) -0.003(3) 0.014(3) C16 0.064(4) 0.057(3) 0.078(4) -0.005(3) 0.022(3) 0.010(3) C28 0.040(3) 0.061(3) 0.047(3) 0.005(2) 0.002(2) -0.007(2) C27 0.031(3) 0.076(4) 0.082(4) 0.017(3) 0.006(3) -0.003(3) C34 0.074(4) 0.067(4) 0.041(3) 0.022(3) -0.013(3) -0.021(3) C4 0.047(3) 0.049(3) 0.048(3) 0.009(2) 0.010(2) 0.001(2) C17 0.078(4) 0.075(4) 0.074(4) 0.032(3) 0.023(3) 0.000(3) C22 0.077(4) 0.077(4) 0.044(3) -0.009(3) 0.002(3) 0.022(3) C25 0.073(4) 0.071(4) 0.068(4) -0.011(3) 0.034(3) -0.002(3) C20 0.052(4) 0.080(5) 0.121(6) -0.021(4) -0.004(4) -0.012(3) C21 0.098(5) 0.051(4) 0.091(5) -0.020(3) 0.003(4) -0.021(3) C35 0.244(12) 0.152(9) 0.078(5) -0.013(6) 0.049(6) -0.040(8) C31 0.138(8) 0.115(7) 0.175(10) -0.041(7) -0.053(7) -0.002(6) C32 0.177(9) 0.111(7) 0.238(11) 0.078(7) -0.128(8) -0.098(7) C36 0.107(6) 0.166(9) 0.192(10) 0.112(8) 0.018(6) 0.037(6) N3 0.194(8) 0.125(7) 0.099(5) -0.009(5) -0.027(6) -0.004(6) C37 0.101(6) 0.081(5) 0.102(6) -0.031(5) 0.005(5) -0.008(4) C38 0.102(5) 0.099(6) 0.091(5) -0.007(5) 0.012(4) -0.013(4) _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 S C12 1.773(4) . ? S C6 1.779(4) . ? S P 2.6284(17) . ? P O2 1.667(3) . ? P O1 1.701(3) . ? P O3 1.715(3) . ? P N1 1.791(4) . ? P C23 1.820(4) . ? O1 C1 1.367(5) . ? O2 C7 1.363(5) . ? O3 C29 1.338(5) . ? N1 C33 1.383(5) . ? N1 N2 1.432(5) . ? N2 C29 1.275(5) . ? C12 C11 1.382(6) . ? C12 C7 1.398(6) . ? O5 C33 1.195(5) . ? O6 C33 1.340(5) . ? O6 C34 1.448(5) . ? O4 C29 1.340(5) . ? O4 C30 1.470(6) . ? C2 C3 1.396(6) . ? C2 C1 1.416(6) . ? C2 C13 1.540(6) . ? C8 C9 1.409(6) . ? C8 C7 1.414(6) . ? C8 C18 1.536(6) . ? C6 C5 1.388(6) . ? C6 C1 1.399(6) . ? C11 C10 1.369(6) . ? C5 C4 1.388(6) . ? C10 C9 1.392(7) . ? C10 C22 1.513(6) . ? C23 C28 1.384(6) . ? C23 C24 1.391(6) . ? C24 C25 1.381(7) . ? C18 C19 1.505(7) . ? C18 C21 1.549(7) . ? C18 C20 1.565(7) . ? C26 C25 1.377(8) . ? C26 C27 1.381(8) . ? C13 C14 1.538(7) . ? C13 C16 1.543(7) . ? C13 C15 1.548(6) . ? C3 C4 1.397(6) . ? C30 C32 1.481(8) . ? C30 C31 1.547(10) . ? C28 C27 1.387(6) . ? C34 C35 1.489(9) . ? C34 C36 1.502(8) . ? C4 C17 1.513(6) . ? N3 C37 1.127(9) . ? C37 C38 1.441(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 C12 S C6 102.6(2) . . ? C12 S P 87.89(15) . . ? C6 S P 88.49(14) . . ? O2 P O1 89.76(15) . . ? O2 P O3 164.98(15) . . ? O1 P O3 87.81(14) . . ? O2 P N1 93.47(16) . . ? O1 P N1 162.45(16) . . ? O3 P N1 84.61(15) . . ? O2 P C23 97.06(17) . . ? O1 P C23 95.11(17) . . ? O3 P C23 97.92(17) . . ? N1 P C23 101.59(18) . . ? O2 P S 84.42(11) . . ? O1 P S 81.40(10) . . ? O3 P S 80.57(10) . . ? N1 P S 81.76(12) . . ? C23 P S 176.22(15) . . ? C1 O1 P 126.2(3) . . ? C7 O2 P 127.3(3) . . ? C29 O3 P 112.2(3) . . ? C33 N1 N2 116.9(3) . . ? C33 N1 P 126.8(3) . . ? N2 N1 P 114.3(3) . . ? C29 N2 N1 104.8(3) . . ? C11 C12 C7 122.1(4) . . ? C11 C12 S 119.8(3) . . ? C7 C12 S 118.1(3) . . ? C33 O6 C34 117.6(4) . . ? C29 O4 C30 117.1(4) . . ? C3 C2 C1 115.3(4) . . ? C3 C2 C13 122.5(4) . . ? C1 C2 C13 122.2(4) . . ? C9 C8 C7 116.0(4) . . ? C9 C8 C18 120.8(4) . . ? C7 C8 C18 123.1(4) . . ? C5 C6 C1 121.1(4) . . ? C5 C6 S 121.7(3) . . ? C1 C6 S 117.2(3) . . ? O5 C33 O6 124.9(4) . . ? O5 C33 N1 124.3(4) . . ? O6 C33 N1 110.8(4) . . ? C10 C11 C12 120.0(4) . . ? C4 C5 C6 119.8(4) . . ? O1 C1 C6 119.2(4) . . ? O1 C1 C2 119.6(4) . . ? C6 C1 C2 121.1(4) . . ? C11 C10 C9 118.2(4) . . ? C11 C10 C22 121.9(5) . . ? C9 C10 C22 119.9(5) . . ? C28 C23 C24 118.2(4) . . ? C28 C23 P 123.3(3) . . ? C24 C23 P 118.5(3) . . ? C25 C24 C23 120.5(5) . . ? O2 C7 C12 121.4(4) . . ? O2 C7 C8 119.1(4) . . ? C12 C7 C8 119.5(4) . . ? N2 C29 O3 121.9(4) . . ? N2 C29 O4 124.6(4) . . ? O3 C29 O4 113.4(4) . . ? C19 C18 C8 112.3(4) . . ? C19 C18 C21 107.3(5) . . ? C8 C18 C21 112.5(4) . . ? C19 C18 C20 110.9(5) . . ? C8 C18 C20 107.7(4) . . ? C21 C18 C20 106.0(4) . . ? C25 C26 C27 119.6(5) . . ? C14 C13 C2 109.8(4) . . ? C14 C13 C16 110.1(4) . . ? C2 C13 C16 110.6(4) . . ? C14 C13 C15 107.5(4) . . ? C2 C13 C15 111.3(4) . . ? C16 C13 C15 107.6(4) . . ? C10 C9 C8 124.1(4) . . ? C2 C3 C4 124.8(4) . . ? O4 C30 C32 105.7(5) . . ? O4 C30 C31 109.5(5) . . ? C32 C30 C31 107.7(7) . . ? C23 C28 C27 121.5(5) . . ? C26 C27 C28 119.6(5) . . ? O6 C34 C35 106.6(5) . . ? O6 C34 C36 106.9(5) . . ? C35 C34 C36 111.5(7) . . ? C5 C4 C3 118.0(4) . . ? C5 C4 C17 121.8(4) . . ? C3 C4 C17 120.1(4) . . ? C26 C25 C24 120.8(5) . . ? N3 C37 C38 178.4(9) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.626 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.063 #===END data_compd18 _database_code_depnum_ccdc_archive 'CCDC 280923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 N4 O6 P S' _chemical_formula_weight 656.76 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M p_21/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 19.6085(11) _cell_length_b 19.8928(11) _cell_length_c 19.3009(11) _cell_angle_alpha 90.00 _cell_angle_beta 111.8530(10) _cell_angle_gamma 90.00 _cell_volume 6987.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2800 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type 'empirical, sadabs' _exptl_absorpt_correction_T_min 0.9464 _exptl_absorpt_correction_T_max 0.9638 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66529 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 12295 _reflns_number_gt 8825 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0909P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12295 _refine_ls_number_parameters 835 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.005 _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 S2 S 1.00314(3) 0.28363(3) 0.21643(3) 0.03853(15) Uani 1 1 d . . . P2 P 0.97835(3) 0.40067(3) 0.17966(3) 0.03968(16) Uani 1 1 d . . . O9 O 0.92679(8) 0.36756(8) 0.09397(8) 0.0419(4) Uani 1 1 d . . . O7 O 0.90440(9) 0.39221(7) 0.20294(9) 0.0465(4) Uani 1 1 d . . . O8 O 1.02937(9) 0.42174(7) 0.26676(9) 0.0449(4) Uani 1 1 d . . . O10 O 0.93326(9) 0.29577(8) 0.00838(9) 0.0483(4) Uani 1 1 d . . . C45 C 1.05747(12) 0.30853(11) 0.30864(12) 0.0365(5) Uani 1 1 d . . . N5 N 1.05282(11) 0.39292(9) 0.14963(11) 0.0428(5) Uani 1 1 d . . . N6 N 1.03900(11) 0.34786(10) 0.08855(11) 0.0438(5) Uani 1 1 d . . . C50 C 1.06196(12) 0.37668(11) 0.32308(13) 0.0383(5) Uani 1 1 d . . . C34 C 0.87253(13) 0.33211(11) 0.20695(12) 0.0396(5) Uani 1 1 d . . . N7 N 0.95800(12) 0.48371(10) 0.15373(12) 0.0497(5) Uani 1 1 d . . . C46 C 1.09444(12) 0.26135(11) 0.36174(13) 0.0405(5) Uani 1 1 d . . . H46 H 1.0909 0.2159 0.3498 0.049 Uiso 1 1 calc R . . C49 C 1.10022(13) 0.40000(11) 0.39639(13) 0.0417(5) Uani 1 1 d . . . C39 C 0.91344(12) 0.27326(11) 0.21600(12) 0.0385(5) Uani 1 1 d . . . C60 C 0.97008(13) 0.33739(11) 0.06316(13) 0.0409(5) Uani 1 1 d . . . C47 C 1.13663(13) 0.28262(12) 0.43269(13) 0.0435(6) Uani 1 1 d . . . C48 C 1.13741(13) 0.35132(12) 0.44822(14) 0.0465(6) Uani 1 1 d . . . H48 H 1.1647 0.3654 0.4966 0.056 Uiso 1 1 calc R . . C35 C 0.80005(13) 0.32932(12) 0.20474(13) 0.0448(6) Uani 1 1 d . . . O12 O 1.15013(11) 0.42182(11) 0.12319(12) 0.0747(6) Uani 1 1 d . . . C61 C 0.97780(14) 0.24878(13) -0.01619(14) 0.0516(6) Uani 1 1 d . . . H61 H 1.0200 0.2725 -0.0200 0.062 Uiso 1 1 calc R . . C36 C 0.77386(14) 0.26555(14) 0.21047(14) 0.0505(6) Uani 1 1 d . . . H36 H 0.7261 0.2622 0.2093 0.061 Uiso 1 1 calc R . . C51 C 1.09645(14) 0.47364(12) 0.41876(14) 0.0513(6) Uani 1 1 d . . . C38 C 0.88481(13) 0.21067(12) 0.22097(13) 0.0445(6) Uani 1 1 d . . . H38 H 0.9132 0.1721 0.2263 0.053 Uiso 1 1 calc R . . C37 C 0.81371(14) 0.20632(13) 0.21789(14) 0.0498(6) Uani 1 1 d . . . C56 C 1.11423(15) 0.43272(13) 0.16825(16) 0.0550(7) Uani 1 1 d . . . O11 O 1.13197(13) 0.47323(12) 0.21742(13) 0.0923(8) Uani 1 1 d . . . C54 C 1.01572(16) 0.49017(15) 0.40386(17) 0.0660(8) Uani 1 1 d . . . H54A H 1.0115 0.5366 0.4151 0.099 Uiso 1 1 calc R . . H54B H 0.9987 0.4624 0.4348 0.099 Uiso 1 1 calc R . . H54C H 0.9865 0.4818 0.3523 0.099 Uiso 1 1 calc R . . C40 C 0.75533(15) 0.39326(14) 0.20136(16) 0.0595(7) Uani 1 1 d . . . C55 C 1.17945(15) 0.23335(14) 0.49261(16) 0.0641(8) Uani 1 1 d . . . H55A H 1.1500 0.2196 0.5203 0.096 Uiso 1 1 calc R . . H55B H 1.2236 0.2544 0.5257 0.096 Uiso 1 1 calc R . . H55C H 1.1919 0.1947 0.4699 0.096 Uiso 1 1 calc R . . C52 C 1.14003(19) 0.48467(15) 0.50211(16) 0.0746(9) Uani 1 1 d . . . H52A H 1.1911 0.4757 0.5131 0.112 Uiso 1 1 calc R . . H52B H 1.1221 0.4549 0.5306 0.112 Uiso 1 1 calc R . . H52C H 1.1343 0.5304 0.5149 0.112 Uiso 1 1 calc R . . C66 C 0.95962(19) 0.51297(15) 0.08955(18) 0.0745(9) Uani 1 1 d . . . H66 H 0.9696 0.4918 0.0514 0.089 Uiso 1 1 calc R . . C62 C 0.92892(18) 0.2246(2) -0.09134(18) 0.0903(11) Uani 1 1 d . . . H62A H 0.8879 0.2009 -0.0873 0.135 Uiso 1 1 calc R . . H62B H 0.9559 0.1949 -0.1110 0.135 Uiso 1 1 calc R . . H62C H 0.9114 0.2623 -0.1242 0.135 Uiso 1 1 calc R . . C53 C 1.12670(18) 0.52166(13) 0.37537(18) 0.0706(9) Uani 1 1 d . . . H53A H 1.0998 0.5160 0.3228 0.106 Uiso 1 1 calc R . . H53B H 1.1777 0.5120 0.3867 0.106 Uiso 1 1 calc R . . H53C H 1.1216 0.5672 0.3893 0.106 Uiso 1 1 calc R . . N8 N 0.9319(2) 0.59184(12) 0.15576(19) 0.1001(11) Uani 1 1 d . . . C42 C 0.79385(18) 0.43291(17) 0.27428(19) 0.0810(10) Uani 1 1 d . . . H42A H 0.7952 0.4061 0.3161 0.121 Uiso 1 1 calc R . . H42B H 0.7672 0.4737 0.2731 0.121 Uiso 1 1 calc R . . H42C H 0.8431 0.4437 0.2790 0.121 Uiso 1 1 calc R . . C43 C 0.67708(16) 0.37642(18) 0.1957(2) 0.0885(11) Uani 1 1 d . . . H43A H 0.6524 0.3513 0.1508 0.133 Uiso 1 1 calc R . . H43B H 0.6507 0.4173 0.1945 0.133 Uiso 1 1 calc R . . H43C H 0.6792 0.3501 0.2381 0.133 Uiso 1 1 calc R . . C44 C 0.77933(18) 0.13938(15) 0.2235(2) 0.0789(9) Uani 1 1 d . . . H44A H 0.7372 0.1468 0.2365 0.118 Uiso 1 1 calc R . . H44B H 0.8145 0.1124 0.2613 0.118 Uiso 1 1 calc R . . H44C H 0.7645 0.1166 0.1764 0.118 Uiso 1 1 calc R . . C65 C 0.9439(2) 0.57801(16) 0.0932(2) 0.0951(12) Uani 1 1 d . . . H65 H 0.9415 0.6097 0.0569 0.114 Uiso 1 1 calc R . . C41 C 0.74965(19) 0.43682(16) 0.13432(19) 0.0834(10) Uani 1 1 d . . . H41A H 0.7978 0.4440 0.1337 0.125 Uiso 1 1 calc R . . H41B H 0.7280 0.4793 0.1379 0.125 Uiso 1 1 calc R . . H41C H 0.7196 0.4145 0.0892 0.125 Uiso 1 1 calc R . . C64 C 0.9410(2) 0.53429(14) 0.1902(2) 0.0857(11) Uani 1 1 d . . . H64 H 0.9362 0.5288 0.2360 0.103 Uiso 1 1 calc R . . C63 C 1.0041(2) 0.19313(15) 0.03980(19) 0.0794(10) Uani 1 1 d . . . H63A H 1.0345 0.2114 0.0873 0.119 Uiso 1 1 calc R . . H63B H 1.0319 0.1615 0.0235 0.119 Uiso 1 1 calc R . . H63C H 0.9626 0.1708 0.0445 0.119 Uiso 1 1 calc R . . C59 C 1.2027(3) 0.5190(4) 0.0978(4) 0.219(4) Uani 1 1 d . . . H59A H 1.2004 0.5102 0.0480 0.328 Uiso 1 1 calc R . . H59B H 1.2405 0.5515 0.1211 0.328 Uiso 1 1 calc R . . H59C H 1.1562 0.5364 0.0957 0.328 Uiso 1 1 calc R . . C57 C 1.2182(2) 0.4603(2) 0.1386(3) 0.0981(14) Uani 1 1 d . . . H57 H 1.2435 0.4689 0.1921 0.118 Uiso 1 1 calc R . . C58 C 1.2630(3) 0.4161(4) 0.1085(6) 0.301(6) Uani 1 1 d . . . H58A H 1.2389 0.4122 0.0554 0.451 Uiso 1 1 calc R . . H58B H 1.2680 0.3724 0.1308 0.451 Uiso 1 1 calc R . . H58C H 1.3108 0.4356 0.1202 0.451 Uiso 1 1 calc R . . S1 S 0.43913(3) 0.30729(3) 0.27019(3) 0.04107(16) Uani 1 1 d . . . P1 P 0.48322(3) 0.19289(3) 0.29745(3) 0.03884(16) Uani 1 1 d . . . O1 O 0.43322(9) 0.18799(8) 0.34897(9) 0.0438(4) Uani 1 1 d . . . O2 O 0.55395(9) 0.22827(8) 0.36618(9) 0.0445(4) Uani 1 1 d . . . O3 O 0.53383(9) 0.20495(8) 0.24233(9) 0.0472(4) Uani 1 1 d . . . O4 O 0.55249(10) 0.16136(9) 0.14512(10) 0.0568(5) Uani 1 1 d . . . N1 N 0.41194(11) 0.16647(10) 0.21278(11) 0.0436(5) Uani 1 1 d . . . C17 C 0.57847(13) 0.29209(11) 0.36305(13) 0.0397(5) Uani 1 1 d . . . O6 O 0.31046(9) 0.19939(10) 0.23084(10) 0.0632(5) Uani 1 1 d . . . N2 N 0.44105(11) 0.14541(11) 0.15861(11) 0.0484(5) Uani 1 1 d . . . N3 N 0.51599(11) 0.11132(10) 0.32300(11) 0.0478(5) Uani 1 1 d . . . O5 O 0.29953(10) 0.15514(11) 0.12067(11) 0.0700(6) Uani 1 1 d . . . C6 C 0.40530(12) 0.30495(12) 0.34331(13) 0.0408(5) Uani 1 1 d . . . C23 C 0.33710(14) 0.17204(12) 0.18314(14) 0.0462(6) Uani 1 1 d . . . C1 C 0.41167(12) 0.24312(11) 0.37905(13) 0.0411(5) Uani 1 1 d . . . C12 C 0.52830(12) 0.33875(11) 0.31873(13) 0.0400(5) Uani 1 1 d . . . C27 C 0.50637(14) 0.16897(12) 0.18013(14) 0.0438(6) Uani 1 1 d . . . C13 C 0.54718(14) 0.40515(12) 0.31365(14) 0.0477(6) Uani 1 1 d . . . H13 H 0.5129 0.4351 0.2827 0.057 Uiso 1 1 calc R . . C16 C 0.65061(13) 0.31118(12) 0.40555(13) 0.0446(6) Uani 1 1 d . . . C5 C 0.37696(13) 0.36045(13) 0.36554(14) 0.0478(6) Uani 1 1 d . . . H5 H 0.3731 0.4012 0.3407 0.057 Uiso 1 1 calc R . . C3 C 0.36511(14) 0.29453(13) 0.46313(15) 0.0503(6) Uani 1 1 d . . . H3 H 0.3519 0.2919 0.5046 0.060 Uiso 1 1 calc R . . C2 C 0.39460(13) 0.23736(12) 0.44319(13) 0.0451(6) Uani 1 1 d . . . C15 C 0.66700(14) 0.37879(13) 0.39981(14) 0.0506(6) Uani 1 1 d . . . H15 H 0.7144 0.3933 0.4279 0.061 Uiso 1 1 calc R . . C4 C 0.35421(14) 0.35525(13) 0.42495(15) 0.0515(6) Uani 1 1 d . . . C14 C 0.61795(15) 0.42616(13) 0.35535(15) 0.0504(6) Uani 1 1 d . . . C28 C 0.53153(16) 0.11296(14) 0.08403(16) 0.0607(7) Uani 1 1 d . . . H28 H 0.4781 0.1138 0.0579 0.073 Uiso 1 1 calc R . . C18 C 0.71013(13) 0.26224(14) 0.45192(15) 0.0538(7) Uani 1 1 d . . . C7 C 0.40862(15) 0.17232(13) 0.48907(14) 0.0528(7) Uani 1 1 d . . . C22 C 0.64159(17) 0.49720(14) 0.35204(19) 0.0731(9) Uani 1 1 d . . . H22A H 0.6491 0.5042 0.3062 0.110 Uiso 1 1 calc R . . H22B H 0.6866 0.5057 0.3935 0.110 Uiso 1 1 calc R . . H22C H 0.6042 0.5273 0.3543 0.110 Uiso 1 1 calc R . . C10 C 0.39555(19) 0.18265(16) 0.56218(17) 0.0736(9) Uani 1 1 d . . . H10A H 0.4268 0.2181 0.5906 0.110 Uiso 1 1 calc R . . H10B H 0.4067 0.1418 0.5907 0.110 Uiso 1 1 calc R . . H10C H 0.3451 0.1945 0.5509 0.110 Uiso 1 1 calc R . . C33 C 0.47802(18) 0.05855(14) 0.33795(17) 0.0656(8) Uani 1 1 d . . . H33 H 0.4306 0.0606 0.3380 0.079 Uiso 1 1 calc R . . C8 C 0.48925(16) 0.15109(16) 0.51061(17) 0.0695(8) Uani 1 1 d . . . H8A H 0.4994 0.1440 0.4662 0.104 Uiso 1 1 calc R . . H8B H 0.4979 0.1102 0.5390 0.104 Uiso 1 1 calc R . . H8C H 0.5208 0.1858 0.5401 0.104 Uiso 1 1 calc R . . C21 C 0.68337(17) 0.21615(18) 0.50066(19) 0.0842(10) Uani 1 1 d . . . H21A H 0.6453 0.1871 0.4692 0.126 Uiso 1 1 calc R . . H21B H 0.6644 0.2431 0.5307 0.126 Uiso 1 1 calc R . . H21C H 0.7237 0.1895 0.5325 0.126 Uiso 1 1 calc R . . N4 N 0.58477(19) 0.02021(15) 0.3448(2) 0.1102(12) Uani 1 1 d . . . C24 C 0.23055(14) 0.20291(17) 0.20793(17) 0.0670(8) Uani 1 1 d . . . H24 H 0.2091 0.2116 0.1541 0.080 Uiso 1 1 calc R . . C19 C 0.77821(16) 0.29828(16) 0.50537(18) 0.0762(9) Uani 1 1 d . . . H19A H 0.8137 0.2656 0.5337 0.114 Uiso 1 1 calc R . . H19B H 0.7646 0.3262 0.5387 0.114 Uiso 1 1 calc R . . H19C H 0.7991 0.3256 0.4773 0.114 Uiso 1 1 calc R . . C9 C 0.35665(18) 0.11672(15) 0.44478(18) 0.0719(8) Uani 1 1 d . . . H9A H 0.3068 0.1292 0.4361 0.108 Uiso 1 1 calc R . . H9B H 0.3683 0.0755 0.4726 0.108 Uiso 1 1 calc R . . H9C H 0.3622 0.1106 0.3978 0.108 Uiso 1 1 calc R . . C32 C 0.5201(2) 0.00492(15) 0.35219(19) 0.0769(9) Uani 1 1 d . . . H32 H 0.5077 -0.0370 0.3653 0.092 Uiso 1 1 calc R . . C11 C 0.31970(18) 0.41390(15) 0.44944(19) 0.0758(9) Uani 1 1 d . . . H11A H 0.3253 0.4079 0.5006 0.114 Uiso 1 1 calc R . . H11B H 0.2684 0.4163 0.4187 0.114 Uiso 1 1 calc R . . H11C H 0.3435 0.4548 0.4445 0.114 Uiso 1 1 calc R . . C29 C 0.56745(19) 0.13470(19) 0.03181(18) 0.0860(10) Uani 1 1 d . . . H29A H 0.5506 0.1789 0.0133 0.129 Uiso 1 1 calc R . . H29B H 0.5551 0.1038 -0.0092 0.129 Uiso 1 1 calc R . . H29C H 0.6198 0.1354 0.0578 0.129 Uiso 1 1 calc R . . C26 C 0.2151(2) 0.2608(3) 0.2471(3) 0.1286(18) Uani 1 1 d . . . H26A H 0.2359 0.2530 0.2999 0.193 Uiso 1 1 calc R . . H26B H 0.1629 0.2666 0.2315 0.193 Uiso 1 1 calc R . . H26C H 0.2364 0.3005 0.2353 0.193 Uiso 1 1 calc R . . C31 C 0.58032(18) 0.08364(17) 0.3270(2) 0.0898(11) Uani 1 1 d . . . H31 H 0.6172 0.1072 0.3180 0.108 Uiso 1 1 calc R . . C20 C 0.73278(17) 0.22037(17) 0.39779(19) 0.0786(10) Uani 1 1 d . . . H20A H 0.7700 0.1887 0.4253 0.118 Uiso 1 1 calc R . . H20B H 0.7518 0.2494 0.3696 0.118 Uiso 1 1 calc R . . H20C H 0.6908 0.1966 0.3644 0.118 Uiso 1 1 calc R . . C25 C 0.2020(2) 0.1376(3) 0.2231(3) 0.150(2) Uani 1 1 d . . . H25A H 0.2199 0.1018 0.2011 0.225 Uiso 1 1 calc R . . H25B H 0.1492 0.1381 0.2020 0.225 Uiso 1 1 calc R . . H25C H 0.2183 0.1308 0.2761 0.225 Uiso 1 1 calc R . . C30 C 0.5546(2) 0.04435(16) 0.1165(2) 0.0909(11) Uani 1 1 d . . . H30A H 0.6069 0.0434 0.1425 0.136 Uiso 1 1 calc R . . H30B H 0.5408 0.0116 0.0771 0.136 Uiso 1 1 calc R . . H30C H 0.5309 0.0340 0.1507 0.136 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 S2 0.0458(3) 0.0321(3) 0.0402(3) -0.0037(2) 0.0190(3) 0.0006(2) P2 0.0497(4) 0.0303(3) 0.0447(4) 0.0014(3) 0.0242(3) 0.0029(3) O9 0.0422(9) 0.0430(9) 0.0432(9) 0.0026(7) 0.0193(8) 0.0053(7) O7 0.0587(10) 0.0317(8) 0.0616(11) -0.0009(7) 0.0370(9) 0.0035(7) O8 0.0638(11) 0.0285(8) 0.0440(9) -0.0017(7) 0.0217(8) -0.0003(7) O10 0.0427(9) 0.0575(11) 0.0437(10) -0.0111(8) 0.0151(8) -0.0025(8) C45 0.0365(12) 0.0346(12) 0.0398(13) -0.0040(10) 0.0159(10) -0.0003(10) N5 0.0484(12) 0.0400(11) 0.0459(12) -0.0078(9) 0.0245(10) -0.0068(9) N6 0.0446(12) 0.0473(12) 0.0443(11) -0.0085(9) 0.0223(10) -0.0062(9) C50 0.0408(13) 0.0351(12) 0.0437(13) -0.0019(10) 0.0213(11) -0.0020(10) C34 0.0492(14) 0.0381(13) 0.0350(12) -0.0026(10) 0.0195(11) -0.0002(11) N7 0.0665(14) 0.0340(11) 0.0556(13) 0.0079(9) 0.0310(11) 0.0049(10) C46 0.0382(13) 0.0336(12) 0.0519(15) -0.0012(11) 0.0192(11) -0.0004(10) C49 0.0447(14) 0.0393(13) 0.0451(14) -0.0069(11) 0.0211(11) -0.0068(11) C39 0.0439(13) 0.0377(12) 0.0345(12) -0.0026(10) 0.0152(10) -0.0025(10) C60 0.0461(15) 0.0411(13) 0.0397(13) 0.0040(11) 0.0206(11) 0.0005(11) C47 0.0370(13) 0.0458(14) 0.0468(14) 0.0032(11) 0.0143(11) -0.0026(10) C48 0.0427(14) 0.0503(15) 0.0455(14) -0.0060(11) 0.0154(12) -0.0094(11) C35 0.0464(14) 0.0503(15) 0.0382(13) -0.0034(11) 0.0165(11) 0.0030(11) O12 0.0605(12) 0.0837(14) 0.0961(16) -0.0397(12) 0.0481(12) -0.0330(11) C61 0.0486(15) 0.0651(17) 0.0480(15) -0.0163(13) 0.0260(12) -0.0081(13) C36 0.0413(14) 0.0640(17) 0.0465(15) -0.0038(12) 0.0168(12) -0.0078(13) C51 0.0609(16) 0.0417(14) 0.0546(16) -0.0131(12) 0.0253(13) -0.0075(12) C38 0.0505(15) 0.0377(13) 0.0411(14) -0.0020(10) 0.0123(11) -0.0043(11) C37 0.0539(16) 0.0477(15) 0.0469(15) -0.0036(11) 0.0177(13) -0.0114(12) C56 0.0567(16) 0.0530(16) 0.0618(17) -0.0139(14) 0.0296(14) -0.0092(13) O11 0.1050(18) 0.0948(17) 0.1010(17) -0.0540(14) 0.0662(15) -0.0556(14) C54 0.076(2) 0.0574(17) 0.072(2) -0.0193(15) 0.0369(17) 0.0045(15) C40 0.0549(17) 0.0586(17) 0.0671(19) -0.0086(14) 0.0253(14) 0.0109(13) C55 0.0548(17) 0.0583(17) 0.0634(18) 0.0062(14) 0.0040(14) 0.0008(14) C52 0.093(2) 0.0588(18) 0.065(2) -0.0247(15) 0.0219(18) -0.0085(17) C66 0.109(3) 0.0548(18) 0.077(2) 0.0230(15) 0.055(2) 0.0178(17) C62 0.072(2) 0.139(3) 0.061(2) -0.043(2) 0.0259(17) -0.006(2) C53 0.093(2) 0.0396(15) 0.088(2) -0.0128(14) 0.0434(19) -0.0148(15) N8 0.170(3) 0.0382(15) 0.112(2) 0.0211(15) 0.077(2) 0.0262(17) C42 0.075(2) 0.082(2) 0.092(2) -0.0351(19) 0.0385(19) 0.0054(17) C43 0.0528(19) 0.095(3) 0.115(3) -0.017(2) 0.0285(19) 0.0133(18) C44 0.075(2) 0.0597(19) 0.103(3) 0.0006(18) 0.035(2) -0.0222(16) C65 0.138(3) 0.051(2) 0.118(3) 0.042(2) 0.073(3) 0.023(2) C41 0.085(2) 0.066(2) 0.093(2) 0.0125(18) 0.025(2) 0.0317(18) C64 0.150(3) 0.0394(16) 0.088(2) 0.0094(16) 0.068(2) 0.0233(18) C63 0.106(3) 0.0609(19) 0.080(2) -0.0038(17) 0.044(2) 0.0190(18) C59 0.154(6) 0.217(8) 0.265(9) 0.055(7) 0.055(6) -0.092(5) C57 0.089(3) 0.103(3) 0.135(3) -0.056(3) 0.080(3) -0.057(2) C58 0.174(6) 0.249(8) 0.599(16) -0.279(10) 0.282(9) -0.148(6) S1 0.0418(3) 0.0424(3) 0.0389(3) 0.0030(3) 0.0150(3) 0.0054(3) P1 0.0387(3) 0.0371(3) 0.0407(3) 0.0002(3) 0.0148(3) 0.0056(3) O1 0.0511(10) 0.0395(9) 0.0463(10) 0.0036(7) 0.0244(8) 0.0050(7) O2 0.0432(9) 0.0421(9) 0.0423(9) 0.0067(7) 0.0090(7) 0.0023(7) O3 0.0476(10) 0.0488(10) 0.0499(10) -0.0042(8) 0.0236(8) 0.0004(8) O4 0.0623(12) 0.0613(11) 0.0603(11) -0.0086(9) 0.0386(10) 0.0000(9) N1 0.0410(11) 0.0458(11) 0.0458(12) -0.0048(9) 0.0182(9) 0.0025(9) C17 0.0437(14) 0.0400(13) 0.0396(13) 0.0005(10) 0.0201(11) 0.0000(10) O6 0.0403(10) 0.0939(15) 0.0554(12) -0.0154(10) 0.0176(9) 0.0069(10) N2 0.0516(13) 0.0530(13) 0.0458(12) -0.0033(10) 0.0240(10) 0.0023(10) N3 0.0481(12) 0.0402(11) 0.0518(13) 0.0014(9) 0.0149(10) 0.0074(10) O5 0.0521(11) 0.0953(16) 0.0525(12) -0.0119(11) 0.0079(10) 0.0152(10) C6 0.0362(13) 0.0461(14) 0.0412(13) 0.0004(11) 0.0155(11) 0.0025(10) C23 0.0517(16) 0.0452(14) 0.0437(15) -0.0007(11) 0.0201(13) 0.0062(12) C1 0.0367(12) 0.0413(13) 0.0467(14) 0.0008(11) 0.0172(11) 0.0019(10) C12 0.0414(13) 0.0423(13) 0.0407(13) -0.0005(10) 0.0203(11) 0.0010(10) C27 0.0497(15) 0.0408(13) 0.0469(14) 0.0004(11) 0.0249(12) 0.0026(11) C13 0.0571(16) 0.0421(14) 0.0519(15) 0.0031(11) 0.0297(13) 0.0077(12) C16 0.0428(14) 0.0537(15) 0.0412(14) -0.0037(11) 0.0202(11) 0.0008(11) C5 0.0452(14) 0.0414(14) 0.0597(16) 0.0005(12) 0.0228(13) 0.0042(11) C3 0.0477(15) 0.0590(17) 0.0524(16) -0.0064(13) 0.0280(13) -0.0058(12) C2 0.0400(13) 0.0523(15) 0.0461(14) -0.0004(11) 0.0196(11) -0.0009(11) C15 0.0447(14) 0.0560(16) 0.0557(16) -0.0096(13) 0.0238(13) -0.0084(12) C4 0.0472(15) 0.0503(15) 0.0643(17) -0.0081(13) 0.0291(13) -0.0009(12) C14 0.0567(16) 0.0456(15) 0.0569(16) -0.0035(12) 0.0304(14) -0.0026(12) C28 0.0649(18) 0.0705(19) 0.0553(17) -0.0144(14) 0.0321(15) -0.0008(15) C18 0.0405(14) 0.0642(17) 0.0518(16) 0.0010(13) 0.0116(12) 0.0042(12) C7 0.0554(16) 0.0574(16) 0.0520(16) 0.0075(13) 0.0272(13) -0.0014(13) C22 0.078(2) 0.0476(17) 0.097(2) -0.0091(16) 0.0363(19) -0.0116(15) C10 0.092(2) 0.077(2) 0.0626(19) 0.0097(16) 0.0420(18) -0.0030(18) C33 0.078(2) 0.0455(16) 0.083(2) 0.0105(14) 0.0414(18) 0.0068(15) C8 0.068(2) 0.079(2) 0.0627(19) 0.0232(16) 0.0267(16) 0.0142(16) C21 0.065(2) 0.096(3) 0.077(2) 0.0356(19) 0.0092(18) 0.0071(18) N4 0.094(2) 0.0597(19) 0.156(3) 0.0113(19) 0.023(2) 0.0363(17) C24 0.0362(15) 0.107(3) 0.0563(18) -0.0008(16) 0.0157(13) 0.0077(15) C19 0.0545(18) 0.086(2) 0.072(2) -0.0123(17) 0.0050(16) 0.0010(16) C9 0.087(2) 0.0596(18) 0.077(2) 0.0006(15) 0.0396(18) -0.0128(16) C32 0.102(3) 0.0413(17) 0.089(2) 0.0142(15) 0.037(2) 0.0142(17) C11 0.088(2) 0.0627(19) 0.101(2) -0.0092(17) 0.062(2) 0.0104(17) C29 0.098(3) 0.111(3) 0.071(2) -0.001(2) 0.056(2) 0.001(2) C26 0.063(2) 0.157(4) 0.169(5) -0.046(4) 0.047(3) 0.019(3) C31 0.0567(19) 0.057(2) 0.153(4) 0.008(2) 0.036(2) 0.0188(16) C20 0.0561(18) 0.083(2) 0.088(2) -0.0229(18) 0.0175(17) 0.0137(16) C25 0.078(3) 0.146(4) 0.226(6) 0.058(4) 0.056(4) -0.016(3) C30 0.132(3) 0.060(2) 0.100(3) -0.0052(19) 0.066(3) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S2 C39 1.768(2) . ? S2 C45 1.771(2) . ? S2 P2 2.4299(8) . ? P2 O8 1.6586(17) . ? P2 O7 1.6786(16) . ? P2 O9 1.7165(17) . ? P2 N7 1.729(2) . ? P2 N5 1.7670(19) . ? O9 C60 1.345(3) . ? O7 C34 1.364(3) . ? O8 C50 1.370(3) . ? O10 C60 1.325(3) . ? O10 C61 1.473(3) . ? C45 C46 1.380(3) . ? C45 C50 1.380(3) . ? N5 C56 1.373(3) . ? N5 N6 1.424(3) . ? N6 C60 1.272(3) . ? C50 C49 1.411(3) . ? C34 C39 1.393(3) . ? C34 C35 1.407(3) . ? N7 C64 1.340(3) . ? N7 C66 1.380(3) . ? C46 C47 1.377(3) . ? C49 C48 1.388(3) . ? C49 C51 1.537(3) . ? C39 C38 1.384(3) . ? C47 C48 1.398(3) . ? C47 C55 1.510(3) . ? C35 C36 1.388(3) . ? C35 C40 1.533(3) . ? O12 C56 1.325(3) . ? O12 C57 1.470(3) . ? C61 C62 1.490(4) . ? C61 C63 1.498(4) . ? C36 C37 1.391(4) . ? C51 C53 1.528(4) . ? C51 C52 1.531(4) . ? C51 C54 1.536(4) . ? C38 C37 1.376(3) . ? C37 C44 1.514(4) . ? C56 O11 1.194(3) . ? C40 C41 1.526(4) . ? C40 C43 1.534(4) . ? C40 C42 1.543(4) . ? C66 C65 1.338(4) . ? N8 C64 1.303(4) . ? N8 C65 1.341(4) . ? C59 C57 1.380(7) . ? C57 C58 1.503(6) . ? S1 C12 1.763(2) . ? S1 C6 1.769(2) . ? S1 P1 2.4217(8) . ? P1 O1 1.6388(16) . ? P1 O2 1.6760(17) . ? P1 O3 1.7205(17) . ? P1 N3 1.747(2) . ? P1 N1 1.789(2) . ? O1 C1 1.379(3) . ? O2 C17 1.367(3) . ? O3 C27 1.328(3) . ? O4 C27 1.324(3) . ? O4 C28 1.458(3) . ? N1 C23 1.367(3) . ? N1 N2 1.428(3) . ? C17 C12 1.391(3) . ? C17 C16 1.398(3) . ? O6 C23 1.332(3) . ? O6 C24 1.463(3) . ? N2 C27 1.279(3) . ? N3 C31 1.352(4) . ? N3 C33 1.378(3) . ? O5 C23 1.203(3) . ? C6 C5 1.375(3) . ? C6 C1 1.393(3) . ? C1 C2 1.402(3) . ? C12 C13 1.385(3) . ? C13 C14 1.384(4) . ? C16 C15 1.397(3) . ? C16 C18 1.527(3) . ? C5 C4 1.380(3) . ? C3 C4 1.389(4) . ? C3 C2 1.394(3) . ? C2 C7 1.534(4) . ? C15 C14 1.391(4) . ? C4 C11 1.510(4) . ? C14 C22 1.496(4) . ? C28 C29 1.493(4) . ? C28 C30 1.500(4) . ? C18 C20 1.526(4) . ? C18 C19 1.528(4) . ? C18 C21 1.539(4) . ? C7 C9 1.531(4) . ? C7 C8 1.537(4) . ? C7 C10 1.539(4) . ? C33 C32 1.314(4) . ? N4 C31 1.302(4) . ? N4 C32 1.363(4) . ? C24 C26 1.469(5) . ? C24 C25 1.487(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C39 S2 C45 105.23(10) . . ? C39 S2 P2 91.14(8) . . ? C45 S2 P2 90.32(7) . . ? O8 P2 O7 90.53(9) . . ? O8 P2 O9 172.02(8) . . ? O7 P2 O9 87.81(8) . . ? O8 P2 N7 92.24(9) . . ? O7 P2 N7 92.53(9) . . ? O9 P2 N7 95.63(9) . . ? O8 P2 N5 95.41(9) . . ? O7 P2 N5 168.74(9) . . ? O9 P2 N5 84.99(8) . . ? N7 P2 N5 96.79(10) . . ? O8 P2 S2 88.08(6) . . ? O7 P2 S2 85.67(6) . . ? O9 P2 S2 84.02(6) . . ? N7 P2 S2 178.17(8) . . ? N5 P2 S2 84.97(7) . . ? C60 O9 P2 110.78(14) . . ? C34 O7 P2 124.23(14) . . ? C50 O8 P2 124.49(14) . . ? C60 O10 C61 116.18(18) . . ? C46 C45 C50 122.8(2) . . ? C46 C45 S2 120.63(17) . . ? C50 C45 S2 116.55(17) . . ? C56 N5 N6 117.25(19) . . ? C56 N5 P2 127.99(17) . . ? N6 N5 P2 113.61(14) . . ? C60 N6 N5 105.63(19) . . ? O8 C50 C45 120.4(2) . . ? O8 C50 C49 119.85(19) . . ? C45 C50 C49 119.7(2) . . ? O7 C34 C39 119.3(2) . . ? O7 C34 C35 120.8(2) . . ? C39 C34 C35 119.9(2) . . ? C64 N7 C66 104.4(2) . . ? C64 N7 P2 129.9(2) . . ? C66 N7 P2 125.66(19) . . ? C47 C46 C45 119.0(2) . . ? C48 C49 C50 115.7(2) . . ? C48 C49 C51 122.0(2) . . ? C50 C49 C51 122.1(2) . . ? C38 C39 C34 122.4(2) . . ? C38 C39 S2 122.22(18) . . ? C34 C39 S2 115.34(17) . . ? N6 C60 O10 126.5(2) . . ? N6 C60 O9 120.8(2) . . ? O10 C60 O9 112.7(2) . . ? C46 C47 C48 117.9(2) . . ? C46 C47 C55 121.3(2) . . ? C48 C47 C55 120.8(2) . . ? C49 C48 C47 124.5(2) . . ? C36 C35 C34 115.7(2) . . ? C36 C35 C40 122.6(2) . . ? C34 C35 C40 121.6(2) . . ? C56 O12 C57 116.5(2) . . ? O10 C61 C62 106.0(2) . . ? O10 C61 C63 108.8(2) . . ? C62 C61 C63 112.8(3) . . ? C35 C36 C37 124.9(2) . . ? C53 C51 C52 107.9(2) . . ? C53 C51 C54 110.3(2) . . ? C52 C51 C54 107.4(2) . . ? C53 C51 C49 111.9(2) . . ? C52 C51 C49 111.4(2) . . ? C54 C51 C49 107.8(2) . . ? C37 C38 C39 119.0(2) . . ? C38 C37 C36 118.2(2) . . ? C38 C37 C44 121.5(3) . . ? C36 C37 C44 120.3(2) . . ? O11 C56 O12 124.3(3) . . ? O11 C56 N5 124.4(2) . . ? O12 C56 N5 111.3(2) . . ? C41 C40 C35 111.6(2) . . ? C41 C40 C43 107.9(3) . . ? C35 C40 C43 111.3(2) . . ? C41 C40 C42 109.8(3) . . ? C35 C40 C42 107.9(2) . . ? C43 C40 C42 108.3(2) . . ? C65 C66 N7 106.1(3) . . ? C64 N8 C65 104.1(3) . . ? C66 C65 N8 111.5(3) . . ? N8 C64 N7 113.9(3) . . ? C59 C57 O12 109.5(4) . . ? C59 C57 C58 108.1(6) . . ? O12 C57 C58 103.6(3) . . ? C12 S1 C6 100.24(11) . . ? C12 S1 P1 90.85(8) . . ? C6 S1 P1 90.66(8) . . ? O1 P1 O2 92.90(9) . . ? O1 P1 O3 175.27(8) . . ? O2 P1 O3 86.16(8) . . ? O1 P1 N3 90.79(9) . . ? O2 P1 N3 93.31(9) . . ? O3 P1 N3 93.89(9) . . ? O1 P1 N1 95.53(9) . . ? O2 P1 N1 168.94(9) . . ? O3 P1 N1 84.86(9) . . ? N3 P1 N1 93.73(10) . . ? O1 P1 S1 86.67(6) . . ? O2 P1 S1 84.29(6) . . ? O3 P1 S1 88.62(6) . . ? N3 P1 S1 176.41(8) . . ? N1 P1 S1 89.04(7) . . ? C1 O1 P1 123.68(14) . . ? C17 O2 P1 123.80(14) . . ? C27 O3 P1 110.54(15) . . ? C27 O4 C28 116.6(2) . . ? C23 N1 N2 112.14(19) . . ? C23 N1 P1 135.29(17) . . ? N2 N1 P1 111.46(14) . . ? O2 C17 C12 117.8(2) . . ? O2 C17 C16 121.5(2) . . ? C12 C17 C16 120.6(2) . . ? C23 O6 C24 117.5(2) . . ? C27 N2 N1 106.24(19) . . ? C31 N3 C33 104.1(2) . . ? C31 N3 P1 129.2(2) . . ? C33 N3 P1 126.57(18) . . ? C5 C6 C1 121.8(2) . . ? C5 C6 S1 122.89(19) . . ? C1 C6 S1 115.28(17) . . ? O5 C23 O6 123.7(2) . . ? O5 C23 N1 123.9(2) . . ? O6 C23 N1 112.3(2) . . ? O1 C1 C6 118.6(2) . . ? O1 C1 C2 121.2(2) . . ? C6 C1 C2 120.2(2) . . ? C13 C12 C17 122.2(2) . . ? C13 C12 S1 122.64(19) . . ? C17 C12 S1 115.12(17) . . ? N2 C27 O4 125.7(2) . . ? N2 C27 O3 120.7(2) . . ? O4 C27 O3 113.5(2) . . ? C14 C13 C12 118.9(2) . . ? C15 C16 C17 115.3(2) . . ? C15 C16 C18 120.8(2) . . ? C17 C16 C18 123.8(2) . . ? C6 C5 C4 119.5(2) . . ? C4 C3 C2 124.1(2) . . ? C3 C2 C1 115.9(2) . . ? C3 C2 C7 122.2(2) . . ? C1 C2 C7 121.9(2) . . ? C14 C15 C16 125.1(2) . . ? C5 C4 C3 118.2(2) . . ? C5 C4 C11 121.5(3) . . ? C3 C4 C11 120.3(2) . . ? C13 C14 C15 117.9(2) . . ? C13 C14 C22 121.3(2) . . ? C15 C14 C22 120.8(3) . . ? O4 C28 C29 107.0(2) . . ? O4 C28 C30 108.2(2) . . ? C29 C28 C30 113.6(3) . . ? C20 C18 C16 107.5(2) . . ? C20 C18 C19 108.3(2) . . ? C16 C18 C19 112.4(2) . . ? C20 C18 C21 110.2(3) . . ? C16 C18 C21 112.2(2) . . ? C19 C18 C21 106.1(2) . . ? C9 C7 C2 110.4(2) . . ? C9 C7 C8 110.9(2) . . ? C2 C7 C8 109.5(2) . . ? C9 C7 C10 107.8(2) . . ? C2 C7 C10 111.2(2) . . ? C8 C7 C10 107.1(2) . . ? C32 C33 N3 108.4(3) . . ? C31 N4 C32 105.7(3) . . ? O6 C24 C26 106.5(3) . . ? O6 C24 C25 109.8(3) . . ? C26 C24 C25 114.7(4) . . ? C33 C32 N4 109.5(3) . . ? N4 C31 N3 112.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.662 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.051 #===END