# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'K. C. Kumara Swamy' _publ_contact_author_email kckssc@uohyd.ernet.in loop_ _publ_author_name V.Srinivas K.V.Sajna K.C.K.Swamy data_compound-6 _database_code_depnum_ccdc_archive 'CCDC 804470' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 N O3 P, C H Cl3' _chemical_formula_sum 'C20 H25 Cl3 N O3 P' _chemical_formula_weight 464.73 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0813(12) _cell_length_b 10.0455(12) _cell_length_c 22.053(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.363(2) _cell_angle_gamma 90.00 _cell_volume 2209.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6315 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.03 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.508 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8964 _exptl_absorpt_correction_T_max 0.9323 _exptl_absorpt_process_details 'SADABS, Sheldrick(1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 20578 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3871 _reflns_number_gt 3463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+5.1375P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3871 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1651 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P -0.00073(9) 1.00827(12) 0.16590(4) 0.0375(3) Uani 1 1 d . . . O1 O 0.0478(2) 1.1190(3) 0.21433(11) 0.0377(6) Uani 1 1 d . . . O2 O 0.0196(3) 0.8741(3) 0.20233(12) 0.0440(7) Uani 1 1 d . . . O3 O -0.1420(3) 1.0290(4) 0.14108(13) 0.0651(11) Uani 1 1 d . . . N1 N 0.2393(3) 0.9840(4) -0.00617(14) 0.0442(9) Uani 1 1 d . . . H1D H 0.2321 0.9538 -0.0383 0.053 Uiso 1 1 d R . . C1 C 0.1673(4) 1.0975(4) 0.25917(17) 0.0369(9) Uani 1 1 d . . . H1A H 0.1753 1.1702 0.2898 0.044 Uiso 1 1 calc R . . H1B H 0.2476 1.1000 0.2382 0.044 Uiso 1 1 calc R . . C2 C 0.1622(4) 0.9654(4) 0.29163(17) 0.0351(8) Uani 1 1 d . . . C3 C 0.1444(4) 0.8557(4) 0.24390(19) 0.0410(10) Uani 1 1 d . . . H3A H 0.2208 0.8567 0.2203 0.049 Uiso 1 1 calc R . . H3B H 0.1433 0.7683 0.2645 0.049 Uiso 1 1 calc R . . C4 C 0.2968(4) 0.9444(6) 0.3327(2) 0.0573(12) Uani 1 1 d . . . H4A H 0.3692 0.9443 0.3075 0.086 Uiso 1 1 calc R . . H4B H 0.2956 0.8589 0.3541 0.086 Uiso 1 1 calc R . . H4C H 0.3115 1.0165 0.3629 0.086 Uiso 1 1 calc R . . C5 C 0.0480(4) 0.9643(5) 0.33007(18) 0.0460(10) Uani 1 1 d . . . H5A H 0.0643 1.0325 0.3620 0.069 Uiso 1 1 calc R . . H5B H 0.0433 0.8766 0.3491 0.069 Uiso 1 1 calc R . . H5C H -0.0369 0.9829 0.3037 0.069 Uiso 1 1 calc R . . C6 C 0.1111(3) 1.0107(4) 0.10959(15) 0.0283(7) Uani 1 1 d . . . C7 C 0.1755(3) 1.1265(4) 0.10448(17) 0.0319(8) Uani 1 1 d . . . H7 H 0.1655 1.1880 0.1362 0.038 Uiso 1 1 calc R . . C8 C 0.2575(4) 1.1772(4) 0.06036(18) 0.0362(9) Uani 1 1 d . . . C9 C 0.3087(4) 1.3068(4) 0.0703(2) 0.0529(11) Uani 1 1 d . . . H9 H 0.3009 1.3504 0.1078 0.064 Uiso 1 1 calc R . . C10 C 0.3707(5) 1.3725(5) 0.0265(3) 0.0667(16) Uani 1 1 d . . . H10 H 0.4043 1.4603 0.0339 0.080 Uiso 1 1 calc R . . C11 C 0.3828(5) 1.3089(6) -0.0276(3) 0.0673(15) Uani 1 1 d . . . H11 H 0.4239 1.3537 -0.0580 0.081 Uiso 1 1 calc R . . C12 C 0.3372(4) 1.1837(6) -0.0381(2) 0.0589(13) Uani 1 1 d . . . H12 H 0.3460 1.1425 -0.0761 0.071 Uiso 1 1 calc R . . C13 C 0.2771(4) 1.1123(4) 0.00547(18) 0.0404(9) Uani 1 1 d . . . C14 C 0.2447(4) 0.8876(4) 0.04181(19) 0.0410(9) Uani 1 1 d . . . H14 H 0.3231 0.9107 0.0733 0.049 Uiso 1 1 calc R . . C15 C 0.2687(5) 0.7466(5) 0.0186(2) 0.0559(12) Uani 1 1 d . . . H15A H 0.3358 0.7507 -0.0100 0.067 Uiso 1 1 calc R . . H15B H 0.3058 0.6900 0.0538 0.067 Uiso 1 1 calc R . . C16 C 0.1445(5) 0.6857(5) -0.0129(2) 0.0579(13) Uani 1 1 d . . . H16A H 0.1650 0.5974 -0.0291 0.069 Uiso 1 1 calc R . . H16B H 0.1065 0.7424 -0.0478 0.069 Uiso 1 1 calc R . . C17 C 0.0436(4) 0.6703(4) 0.03057(19) 0.0456(10) Uani 1 1 d . . . H17A H -0.0451 0.6494 0.0069 0.055 Uiso 1 1 calc R . . H17B H 0.0702 0.5947 0.0585 0.055 Uiso 1 1 calc R . . C18 C 0.0325(4) 0.7933(4) 0.06757(18) 0.0399(9) Uani 1 1 d . . . H18 H -0.0432 0.8023 0.0883 0.048 Uiso 1 1 calc R . . C19 C 0.1222(3) 0.8902(4) 0.07301(15) 0.0286(7) Uani 1 1 d . . . Cl2 Cl 0.48208(11) 0.60061(11) 0.33549(5) 0.0498(3) Uani 1 1 d . . . Cl3 Cl 0.45430(14) 0.33136(12) 0.29303(7) 0.0693(4) Uani 1 1 d . . . Cl4 Cl 0.34208(11) 0.54773(15) 0.21458(5) 0.0630(4) Uani 1 1 d . . . C20 C 0.3771(4) 0.4885(4) 0.2908(2) 0.0453(10) Uani 1 1 d . . . H20 H 0.2910 0.4807 0.3080 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.0265(5) 0.0613(7) 0.0266(5) -0.0080(4) 0.0107(4) -0.0071(4) O1 0.0356(14) 0.0467(16) 0.0319(13) -0.0046(12) 0.0080(11) 0.0116(12) O2 0.0472(16) 0.0572(18) 0.0309(13) -0.0140(13) 0.0167(12) -0.0267(14) O3 0.0315(15) 0.135(3) 0.0308(15) -0.0069(18) 0.0110(12) -0.0068(18) N1 0.047(2) 0.064(2) 0.0237(16) -0.0036(15) 0.0118(14) -0.0171(17) C1 0.036(2) 0.039(2) 0.036(2) -0.0127(17) 0.0047(16) -0.0009(16) C2 0.0273(19) 0.045(2) 0.0335(19) -0.0031(17) 0.0067(15) 0.0034(16) C3 0.048(2) 0.034(2) 0.047(2) -0.0016(18) 0.0286(19) -0.0038(17) C4 0.038(2) 0.081(3) 0.051(3) 0.006(3) 0.001(2) 0.009(2) C5 0.044(2) 0.067(3) 0.029(2) -0.0032(19) 0.0119(17) 0.006(2) C6 0.0224(17) 0.040(2) 0.0236(17) -0.0016(15) 0.0062(13) -0.0023(14) C7 0.0314(19) 0.0304(19) 0.0344(19) -0.0025(15) 0.0059(15) 0.0040(15) C8 0.0290(19) 0.036(2) 0.043(2) 0.0118(17) 0.0034(16) 0.0005(15) C9 0.050(3) 0.038(2) 0.072(3) 0.008(2) 0.011(2) -0.0031(19) C10 0.044(3) 0.046(3) 0.109(5) 0.028(3) 0.007(3) -0.012(2) C11 0.055(3) 0.084(4) 0.062(3) 0.027(3) 0.010(2) -0.025(3) C12 0.045(2) 0.087(4) 0.045(2) 0.016(2) 0.009(2) -0.027(2) C13 0.0302(19) 0.055(3) 0.036(2) 0.0086(19) 0.0032(16) -0.0097(18) C14 0.034(2) 0.047(2) 0.044(2) -0.0080(19) 0.0090(17) -0.0029(17) C15 0.053(3) 0.061(3) 0.057(3) -0.005(2) 0.020(2) 0.010(2) C16 0.079(3) 0.050(3) 0.049(3) -0.022(2) 0.027(2) -0.016(2) C17 0.053(3) 0.039(2) 0.044(2) -0.0051(19) 0.0065(19) -0.0076(19) C18 0.044(2) 0.038(2) 0.040(2) -0.0007(17) 0.0122(17) -0.0036(17) C19 0.0260(17) 0.0370(19) 0.0231(16) 0.0009(15) 0.0046(13) -0.0047(15) Cl2 0.0456(6) 0.0474(6) 0.0551(6) -0.0108(5) 0.0033(5) -0.0103(5) Cl3 0.0734(8) 0.0395(6) 0.1071(11) -0.0143(6) 0.0534(8) -0.0087(5) Cl4 0.0446(6) 0.0926(10) 0.0520(7) -0.0221(6) 0.0077(5) -0.0021(6) C20 0.032(2) 0.050(2) 0.058(3) -0.021(2) 0.0189(19) -0.0091(18) _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 1.465(3) . ? P O2 1.567(3) . ? P O1 1.570(3) . ? P C6 1.795(3) . ? O1 C1 1.459(4) . ? O2 C3 1.457(5) . ? N1 C13 1.357(5) . ? N1 C14 1.430(5) . ? N1 H1D 0.7651 . ? C1 C2 1.512(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.516(5) . ? C2 C5 1.526(5) . ? C2 C4 1.533(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.344(5) . ? C6 C19 1.468(5) . ? C7 C8 1.457(5) . ? C7 H7 0.9500 . ? C8 C9 1.405(6) . ? C8 C13 1.414(6) . ? C9 C10 1.390(7) . ? C9 H9 0.9500 . ? C10 C11 1.375(8) . ? C10 H10 0.9500 . ? C11 C12 1.348(8) . ? C11 H11 0.9500 . ? C12 C13 1.406(6) . ? C12 H12 0.9500 . ? C14 C19 1.498(5) . ? C14 C15 1.537(6) . ? C14 H14 1.0000 . ? C15 C16 1.474(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.503(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.494(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.323(5) . ? C18 H18 0.9500 . ? Cl2 C20 1.748(4) . ? Cl3 C20 1.758(4) . ? Cl4 C20 1.769(5) . ? C20 H20 1.0000 . ? 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 O2 111.16(19) . . ? O3 P O1 110.09(18) . . ? O2 P O1 104.84(14) . . ? O3 P C6 114.47(16) . . ? O2 P C6 108.55(16) . . ? O1 P C6 107.21(15) . . ? C1 O1 P 120.0(2) . . ? C3 O2 P 117.9(2) . . ? C13 N1 C14 121.6(3) . . ? C13 N1 H1D 122.6 . . ? C14 N1 H1D 113.9 . . ? O1 C1 C2 111.7(3) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C3 108.5(3) . . ? C1 C2 C5 110.5(3) . . ? C3 C2 C5 110.9(3) . . ? C1 C2 C4 108.3(3) . . ? C3 C2 C4 108.4(3) . . ? C5 C2 C4 110.2(3) . . ? O2 C3 C2 110.4(3) . . ? O2 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O2 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C19 126.2(3) . . ? C7 C6 P 115.4(3) . . ? C19 C6 P 118.3(3) . . ? C6 C7 C8 133.3(3) . . ? C6 C7 H7 113.3 . . ? C8 C7 H7 113.3 . . ? C9 C8 C13 117.8(4) . . ? C9 C8 C7 116.8(4) . . ? C13 C8 C7 125.0(4) . . ? C10 C9 C8 121.6(5) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C12 C11 C10 120.8(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 121.9(5) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? N1 C13 C12 119.5(4) . . ? N1 C13 C8 122.0(3) . . ? C12 C13 C8 118.5(4) . . ? N1 C14 C19 112.5(3) . . ? N1 C14 C15 111.7(3) . . ? C19 C14 C15 110.4(3) . . ? N1 C14 H14 107.3 . . ? C19 C14 H14 107.3 . . ? C15 C14 H14 107.3 . . ? C16 C15 C14 112.0(4) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 110.5(4) . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 112.0(3) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 123.7(4) . . ? C19 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? C18 C19 C6 123.5(3) . . ? C18 C19 C14 122.9(3) . . ? C6 C19 C14 113.6(3) . . ? Cl2 C20 Cl3 109.4(2) . . ? Cl2 C20 Cl4 109.9(2) . . ? Cl3 C20 Cl4 110.8(2) . . ? Cl2 C20 H20 108.9 . . ? Cl3 C20 H20 108.9 . . ? Cl4 C20 H20 108.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D O3 0.77 2.32 2.997(4) 147.8 3_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.729 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.080 #===END data_compound-7 _database_code_depnum_ccdc_archive 'CCDC 804471' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H23 Cl N O5 P' _chemical_formula_sum 'C20 H23 Cl N O5 P' _chemical_formula_weight 423.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.733(4) _cell_length_b 9.887(3) _cell_length_c 19.893(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.33(4) _cell_angle_gamma 90.00 _cell_volume 1992.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1072 _cell_measurement_theta_min 2.8266 _cell_measurement_theta_max 29.3787 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9361 _exptl_absorpt_correction_T_max 0.9530 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 7946 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.1256 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3507 _reflns_number_gt 1637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _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^)+(0.0998P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3507 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1376 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1616 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.61130(15) 1.10499(14) 0.63327(9) 0.0781(5) Uani 1 1 d . . . P1 P 0.00953(13) 0.79396(12) 0.57699(7) 0.0454(4) Uani 1 1 d . . . O1 O -0.1243(3) 0.7655(4) 0.5294(2) 0.0779(12) Uani 1 1 d . . . O2 O 0.0315(4) 0.7480(3) 0.65579(19) 0.0549(9) Uani 1 1 d . . . O3 O 0.0387(3) 0.9490(3) 0.58329(16) 0.0467(9) Uani 1 1 d . . . O4 O 0.2540(3) 0.6297(3) 0.43358(17) 0.0520(9) Uani 1 1 d . . . O5 O 0.0808(4) 0.7549(3) 0.3786(2) 0.0601(10) Uani 1 1 d . . . N1 N 0.3546(4) 0.5972(3) 0.5027(2) 0.0474(11) Uani 1 1 d . . . C1 C 0.1481(6) 0.7979(5) 0.7116(3) 0.0597(15) Uani 1 1 d . . . H1A H 0.2269 0.7665 0.7027 0.072 Uiso 1 1 d R . . H1B H 0.1495 0.7622 0.7572 0.072 Uiso 1 1 d R . . C2 C 0.1482(5) 0.9510(4) 0.7141(3) 0.0452(12) Uani 1 1 d . . . C3 C 0.1457(5) 1.0033(4) 0.6425(3) 0.0492(13) Uani 1 1 d . . . H3A H 0.1381 1.1011 0.6422 0.059 Uiso 1 1 calc R . . H3B H 0.2288 0.9811 0.6358 0.059 Uiso 1 1 calc R . . C4 C 0.2763(6) 0.9980(6) 0.7693(3) 0.092(2) Uani 1 1 d . . . H4A H 0.3497 0.9670 0.7561 0.138 Uiso 1 1 calc R . . H4B H 0.2826 0.9617 0.8150 0.138 Uiso 1 1 calc R . . H4C H 0.2774 1.0950 0.7715 0.138 Uiso 1 1 calc R . . C5 C 0.0294(5) 1.0031(5) 0.7331(3) 0.0680(16) Uani 1 1 d . . . H5A H 0.0312 1.1002 0.7347 0.082 Uiso 1 1 d R . . H5B H 0.0333 0.9683 0.7788 0.082 Uiso 1 1 d R . . H5C H -0.0508 0.9735 0.6976 0.082 Uiso 1 1 d R . . C6 C 0.1402(4) 0.7173(4) 0.5501(2) 0.0338(11) Uani 1 1 d . . . C7 C 0.1942(4) 0.8072(4) 0.5023(2) 0.0408(12) Uani 1 1 d . . . H7 H 0.1473 0.8938 0.4935 0.049 Uiso 1 1 calc R . . C8 C 0.3411(4) 0.8320(4) 0.5351(2) 0.0401(12) Uani 1 1 d . . . C9 C 0.4008(5) 0.9520(4) 0.5631(3) 0.0461(13) Uani 1 1 d . . . H9 H 0.3504 1.0296 0.5606 0.055 Uiso 1 1 calc R . . C10 C 0.5376(5) 0.9562(5) 0.5953(3) 0.0529(14) Uani 1 1 d . . . C11 C 0.6138(5) 0.8433(5) 0.5954(3) 0.0582(14) Uani 1 1 d . . . H11 H 0.7051 0.8481 0.6162 0.070 Uiso 1 1 calc R . . C12 C 0.5559(5) 0.7242(5) 0.5649(3) 0.0542(14) Uani 1 1 d . . . H12 H 0.6071 0.6487 0.5641 0.065 Uiso 1 1 calc R . . C13 C 0.4188(5) 0.7193(4) 0.5351(3) 0.0434(12) Uani 1 1 d . . . C14 C 0.1679(5) 0.7317(5) 0.4322(3) 0.0475(13) Uani 1 1 d . . . C15 C 0.2847(4) 0.5193(4) 0.5427(3) 0.0434(12) Uani 1 1 d . . . H15 H 0.2432 0.4420 0.5128 0.052 Uiso 1 1 calc R . . C16 C 0.3924(5) 0.4617(5) 0.6087(3) 0.0566(14) Uani 1 1 d . . . H16A H 0.4589 0.4157 0.5940 0.068 Uiso 1 1 calc R . . H16B H 0.4350 0.5352 0.6403 0.068 Uiso 1 1 calc R . . C17 C 0.3329(5) 0.3628(5) 0.6485(3) 0.0642(15) Uani 1 1 d . . . H17A H 0.3009 0.2835 0.6191 0.077 Uiso 1 1 calc R . . H17B H 0.4007 0.3338 0.6918 0.077 Uiso 1 1 calc R . . C18 C 0.2197(5) 0.4268(5) 0.6671(3) 0.0564(14) Uani 1 1 d . . . H18A H 0.1776 0.3584 0.6872 0.068 Uiso 1 1 calc R . . H18B H 0.2545 0.4961 0.7029 0.068 Uiso 1 1 calc R . . C19 C 0.1175(5) 0.4895(4) 0.6025(3) 0.0483(13) Uani 1 1 d . . . H19A H 0.0740 0.4181 0.5696 0.058 Uiso 1 1 calc R . . H19B H 0.0511 0.5348 0.6175 0.058 Uiso 1 1 calc R . . C20 C 0.1763(4) 0.5901(4) 0.5640(2) 0.0367(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0925(12) 0.0794(10) 0.0698(11) -0.0146(8) 0.0366(10) -0.0390(8) P1 0.0496(9) 0.0515(8) 0.0452(8) -0.0099(7) 0.0290(7) -0.0004(6) O1 0.037(2) 0.108(3) 0.092(3) -0.044(3) 0.024(2) -0.004(2) O2 0.077(3) 0.0534(19) 0.052(2) -0.0037(18) 0.044(2) -0.0062(18) O3 0.067(2) 0.0505(18) 0.0265(18) -0.0049(16) 0.0208(18) 0.0050(16) O4 0.071(2) 0.057(2) 0.036(2) -0.0038(17) 0.0280(19) 0.0024(19) O5 0.073(3) 0.072(2) 0.038(2) 0.007(2) 0.022(2) 0.000(2) N1 0.060(3) 0.049(2) 0.044(3) 0.000(2) 0.033(2) 0.001(2) C1 0.087(4) 0.063(3) 0.041(3) 0.009(3) 0.037(3) 0.014(3) C2 0.060(3) 0.052(3) 0.031(3) -0.007(2) 0.025(3) -0.003(3) C3 0.066(3) 0.048(3) 0.043(3) -0.004(3) 0.031(3) -0.002(3) C4 0.098(5) 0.121(5) 0.052(4) -0.018(4) 0.017(4) -0.019(4) C5 0.100(4) 0.071(3) 0.050(4) 0.002(3) 0.049(3) 0.018(3) C6 0.046(3) 0.035(2) 0.028(3) -0.004(2) 0.023(2) -0.005(2) C7 0.055(3) 0.039(2) 0.038(3) 0.000(2) 0.027(3) 0.001(2) C8 0.047(3) 0.046(3) 0.037(3) 0.004(2) 0.027(3) -0.003(2) C9 0.068(4) 0.043(3) 0.043(3) 0.003(2) 0.040(3) -0.004(3) C10 0.060(4) 0.067(3) 0.045(3) -0.001(3) 0.035(3) -0.011(3) C11 0.048(3) 0.076(3) 0.056(4) 0.002(3) 0.025(3) -0.012(3) C12 0.055(4) 0.060(3) 0.062(4) 0.005(3) 0.038(3) -0.002(3) C13 0.054(3) 0.045(3) 0.042(3) 0.000(2) 0.031(3) -0.006(2) C14 0.060(4) 0.051(3) 0.040(3) 0.008(3) 0.028(3) -0.002(3) C15 0.052(3) 0.040(2) 0.044(3) 0.000(2) 0.023(3) 0.002(2) C16 0.060(3) 0.052(3) 0.065(4) 0.008(3) 0.031(3) 0.009(3) C17 0.073(4) 0.058(3) 0.062(4) 0.012(3) 0.022(3) 0.002(3) C18 0.077(4) 0.047(3) 0.052(4) 0.012(3) 0.031(3) 0.000(3) C19 0.063(3) 0.040(2) 0.054(3) -0.001(3) 0.036(3) -0.007(2) C20 0.041(3) 0.042(3) 0.030(3) -0.007(2) 0.016(2) -0.005(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 Cl1 C10 1.722(5) . ? P1 O1 1.462(4) . ? P1 O3 1.561(3) . ? P1 O2 1.573(4) . ? P1 C6 1.822(4) . ? O2 C1 1.456(6) . ? O3 C3 1.449(6) . ? O4 C14 1.362(5) . ? O4 N1 1.475(5) . ? O5 C14 1.185(6) . ? N1 C13 1.433(5) . ? N1 C15 1.478(5) . ? C1 C2 1.515(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9699 . ? C2 C3 1.508(6) . ? C2 C4 1.520(7) . ? C2 C5 1.534(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9601 . ? C5 H5B 0.9599 . ? C5 H5C 0.9601 . ? C6 C20 1.318(5) . ? C6 C7 1.549(5) . ? C7 C8 1.513(6) . ? C7 C14 1.522(7) . ? C7 H7 0.9800 . ? C8 C9 1.377(6) . ? C8 C13 1.392(6) . ? C9 C10 1.394(7) . ? C9 H9 0.9300 . ? C10 C11 1.384(7) . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.393(6) . ? C12 H12 0.9300 . ? C15 C20 1.533(5) . ? C15 C16 1.544(7) . ? C15 H15 0.9800 . ? C16 C17 1.524(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.519(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.514(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O3 111.6(2) . . ? O1 P1 O2 112.3(2) . . ? O3 P1 O2 104.11(18) . . ? O1 P1 C6 114.6(2) . . ? O3 P1 C6 106.18(17) . . ? O2 P1 C6 107.21(19) . . ? C1 O2 P1 118.0(3) . . ? C3 O3 P1 120.9(3) . . ? C14 O4 N1 117.5(4) . . ? C13 N1 O4 109.3(3) . . ? C13 N1 C15 116.8(3) . . ? O4 N1 C15 105.6(3) . . ? O2 C1 C2 110.8(4) . . ? O2 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C1 108.2(4) . . ? C3 C2 C4 107.8(4) . . ? C1 C2 C4 108.7(5) . . ? C3 C2 C5 111.2(4) . . ? C1 C2 C5 110.7(4) . . ? C4 C2 C5 110.3(4) . . ? O3 C3 C2 113.7(4) . . ? O3 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? O3 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.4 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.4 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C20 C6 C7 122.1(3) . . ? C20 C6 P1 122.5(3) . . ? C7 C6 P1 115.0(3) . . ? C8 C7 C14 109.0(4) . . ? C8 C7 C6 112.1(4) . . ? C14 C7 C6 106.7(3) . . ? C8 C7 H7 109.7 . . ? C14 C7 H7 109.7 . . ? C6 C7 H7 109.7 . . ? C9 C8 C13 119.4(4) . . ? C9 C8 C7 126.4(4) . . ? C13 C8 C7 114.2(4) . . ? C8 C9 C10 119.3(4) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.6(5) . . ? C11 C10 Cl1 120.2(4) . . ? C9 C10 Cl1 119.2(4) . . ? C12 C11 C10 120.6(5) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 118.5(4) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C8 C13 C12 121.4(4) . . ? C8 C13 N1 118.3(4) . . ? C12 C13 N1 120.2(4) . . ? O5 C14 O4 119.3(5) . . ? O5 C14 C7 125.5(5) . . ? O4 C14 C7 115.2(5) . . ? N1 C15 C20 118.6(3) . . ? N1 C15 C16 106.2(4) . . ? C20 C15 C16 110.9(4) . . ? N1 C15 H15 106.9 . . ? C20 C15 H15 106.9 . . ? C16 C15 H15 106.9 . . ? C17 C16 C15 110.7(4) . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 111.4(4) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 112.0(4) . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 113.0(4) . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C6 C20 C19 126.1(4) . . ? C6 C20 C15 125.1(3) . . ? C19 C20 C15 108.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.649 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.093 #===END data_compound-9 _database_code_depnum_ccdc_archive 'CCDC 804472' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H22 N O5 P' _chemical_formula_weight 471.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1245(12) _cell_length_b 10.1712(12) _cell_length_c 24.0509(19) _cell_angle_alpha 90.00 _cell_angle_beta 114.460(4) _cell_angle_gamma 90.00 _cell_volume 2254.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8632 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.02 _exptl_crystal_description blocks _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9559 _exptl_absorpt_correction_T_max 0.9651 _exptl_absorpt_process_details 'SADABS, Sheldrick(1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 13113 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3950 _reflns_number_gt 3467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.4968P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3950 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.87334(5) 0.72298(4) 0.86234(2) 0.04132(15) Uani 1 1 d . . . O1 O 0.77176(14) 0.83186(12) 0.84528(7) 0.0611(4) Uani 1 1 d . . . O2 O 0.97781(13) 0.73578(12) 0.82801(5) 0.0468(3) Uani 1 1 d . . . O3 O 0.98247(12) 0.71490(11) 0.93213(5) 0.0452(3) Uani 1 1 d . . . O4 O 0.63660(13) 0.33081(12) 0.87632(5) 0.0500(3) Uani 1 1 d . . . O5 O 0.68265(16) 0.46767(15) 0.95270(6) 0.0653(4) Uani 1 1 d . . . N1 N 0.68269(15) 0.28519(13) 0.82896(6) 0.0449(3) Uani 1 1 d . . . C1 C 1.11147(18) 0.78707(15) 0.95868(7) 0.0413(4) Uani 1 1 d . . . C2 C 1.1216(2) 0.87561(17) 1.00381(7) 0.0479(4) Uani 1 1 d . . . H2 H 1.0425 0.8907 1.0131 0.057 Uiso 1 1 calc R . . C3 C 1.2502(2) 0.94112(19) 1.03482(8) 0.0584(5) Uani 1 1 d . . . H3 H 1.2587 1.0017 1.0651 0.070 Uiso 1 1 calc R . . C4 C 1.3657(2) 0.9161(2) 1.02066(8) 0.0631(6) Uani 1 1 d . . . H4 H 1.4527 0.9605 1.0414 0.076 Uiso 1 1 calc R . . C5 C 1.3549(2) 0.8261(2) 0.97606(8) 0.0568(5) Uani 1 1 d . . . H5 H 1.4351 0.8101 0.9676 0.068 Uiso 1 1 calc R . . C6 C 1.22589(19) 0.75848(17) 0.94337(7) 0.0445(4) Uani 1 1 d . . . C7 C 1.21500(18) 0.65835(18) 0.89710(8) 0.0462(4) Uani 1 1 d . . . C8 C 1.3279(2) 0.5712(2) 0.90653(9) 0.0607(5) Uani 1 1 d . . . H8 H 1.4114 0.5757 0.9427 0.073 Uiso 1 1 calc R . . C9 C 1.3188(2) 0.4781(2) 0.86337(11) 0.0729(6) Uani 1 1 d . . . H9 H 1.3955 0.4203 0.8709 0.087 Uiso 1 1 calc R . . C10 C 1.1971(3) 0.4703(2) 0.80944(11) 0.0737(6) Uani 1 1 d . . . H10 H 1.1914 0.4077 0.7804 0.088 Uiso 1 1 calc R . . C11 C 1.0839(2) 0.5552(2) 0.79854(9) 0.0596(5) Uani 1 1 d . . . H11 H 1.0012 0.5506 0.7620 0.072 Uiso 1 1 calc R . . C12 C 1.09326(18) 0.64710(17) 0.84189(7) 0.0447(4) Uani 1 1 d . . . C13 C 0.79974(17) 0.55965(15) 0.85042(7) 0.0377(4) Uani 1 1 d . . . C14 C 0.70148(17) 0.52228(16) 0.79546(7) 0.0397(4) Uani 1 1 d . . . C15 C 0.6389(2) 0.61119(19) 0.74030(8) 0.0550(5) Uani 1 1 d . . . H15A H 0.6880 0.6955 0.7503 0.066 Uiso 1 1 calc R . . H15B H 0.5370 0.6262 0.7305 0.066 Uiso 1 1 calc R . . C16 C 0.6531(2) 0.5555(2) 0.68477(8) 0.0648(6) Uani 1 1 d . . . H16A H 0.7546 0.5544 0.6919 0.078 Uiso 1 1 calc R . . H16B H 0.6017 0.6117 0.6499 0.078 Uiso 1 1 calc R . . C17 C 0.5925(3) 0.4176(2) 0.67070(8) 0.0676(6) Uani 1 1 d . . . H17A H 0.6114 0.3818 0.6373 0.081 Uiso 1 1 calc R . . H17B H 0.4882 0.4202 0.6579 0.081 Uiso 1 1 calc R . . C18 C 0.6607(2) 0.3295(2) 0.72629(8) 0.0607(5) Uani 1 1 d . . . H18A H 0.7639 0.3215 0.7372 0.073 Uiso 1 1 calc R . . H18B H 0.6182 0.2424 0.7166 0.073 Uiso 1 1 calc R . . C19 C 0.63696(18) 0.38529(17) 0.78040(7) 0.0433(4) Uani 1 1 d . . . H19 H 0.5319 0.3955 0.7666 0.052 Uiso 1 1 calc R . . C20 C 0.83580(19) 0.25639(16) 0.85677(7) 0.0415(4) Uani 1 1 d . . . C21 C 0.8872(2) 0.13785(18) 0.84568(8) 0.0542(5) Uani 1 1 d . . . H21 H 0.8241 0.0757 0.8198 0.065 Uiso 1 1 calc R . . C22 C 1.0343(2) 0.1142(2) 0.87394(10) 0.0628(5) Uani 1 1 d . . . H22 H 1.0712 0.0356 0.8665 0.075 Uiso 1 1 calc R . . C23 C 1.1274(2) 0.2053(2) 0.91301(10) 0.0627(5) Uani 1 1 d . . . H23 H 1.2265 0.1881 0.9313 0.075 Uiso 1 1 calc R . . C24 C 1.07476(19) 0.32259(19) 0.92536(8) 0.0512(4) Uani 1 1 d . . . H24 H 1.1372 0.3831 0.9526 0.061 Uiso 1 1 calc R . . C25 C 0.92780(17) 0.34751(16) 0.89642(7) 0.0400(4) Uani 1 1 d . . . C26 C 0.85181(18) 0.46686(15) 0.90575(7) 0.0404(4) Uani 1 1 d . . . H26 H 0.9180 0.5146 0.9420 0.048 Uiso 1 1 calc R . . C27 C 0.71993(19) 0.42505(17) 0.91513(8) 0.0461(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0425(3) 0.0323(2) 0.0466(3) -0.00007(17) 0.0158(2) -0.00115(17) O1 0.0596(8) 0.0357(7) 0.0826(9) 0.0023(6) 0.0242(7) 0.0066(6) O2 0.0479(7) 0.0476(7) 0.0419(6) 0.0055(5) 0.0155(5) -0.0021(5) O3 0.0483(7) 0.0451(7) 0.0433(6) -0.0073(5) 0.0201(5) -0.0119(5) O4 0.0478(7) 0.0548(7) 0.0514(7) 0.0003(6) 0.0246(6) -0.0061(6) O5 0.0765(9) 0.0756(10) 0.0549(8) -0.0031(7) 0.0385(7) 0.0047(8) N1 0.0473(8) 0.0405(8) 0.0453(8) -0.0014(6) 0.0177(7) -0.0042(6) C1 0.0462(9) 0.0352(9) 0.0379(8) 0.0022(6) 0.0128(7) -0.0085(7) C2 0.0623(11) 0.0386(9) 0.0410(9) 0.0005(7) 0.0196(8) -0.0048(8) C3 0.0801(14) 0.0485(11) 0.0410(9) -0.0058(8) 0.0195(9) -0.0198(10) C4 0.0669(13) 0.0690(13) 0.0413(9) -0.0011(9) 0.0103(9) -0.0325(11) C5 0.0508(10) 0.0727(13) 0.0434(10) 0.0035(9) 0.0159(8) -0.0173(10) C6 0.0478(10) 0.0472(10) 0.0359(8) 0.0043(7) 0.0147(7) -0.0077(8) C7 0.0432(9) 0.0523(10) 0.0456(9) 0.0011(8) 0.0209(8) -0.0056(8) C8 0.0470(10) 0.0756(14) 0.0610(11) 0.0004(10) 0.0240(9) 0.0005(10) C9 0.0616(13) 0.0812(15) 0.0870(16) -0.0059(13) 0.0420(13) 0.0113(12) C10 0.0760(15) 0.0825(16) 0.0748(14) -0.0239(12) 0.0434(13) -0.0021(12) C11 0.0559(11) 0.0767(14) 0.0496(10) -0.0115(9) 0.0250(9) -0.0064(10) C12 0.0452(9) 0.0507(10) 0.0426(9) 0.0011(7) 0.0225(8) -0.0056(8) C13 0.0379(8) 0.0332(8) 0.0401(8) 0.0012(6) 0.0143(7) 0.0010(7) C14 0.0367(8) 0.0384(9) 0.0413(8) 0.0033(7) 0.0134(7) 0.0031(7) C15 0.0533(11) 0.0491(10) 0.0473(10) 0.0082(8) 0.0056(8) 0.0027(9) C16 0.0651(13) 0.0785(15) 0.0414(10) 0.0160(9) 0.0125(9) 0.0009(11) C17 0.0802(14) 0.0747(14) 0.0380(9) -0.0015(9) 0.0146(9) 0.0074(12) C18 0.0786(14) 0.0534(11) 0.0449(10) -0.0043(9) 0.0203(10) 0.0050(10) C19 0.0397(9) 0.0430(9) 0.0401(8) -0.0005(7) 0.0094(7) -0.0017(7) C20 0.0490(9) 0.0357(8) 0.0395(8) 0.0047(7) 0.0180(7) 0.0001(7) C21 0.0757(13) 0.0395(10) 0.0508(10) 0.0026(8) 0.0298(10) 0.0041(9) C22 0.0814(15) 0.0501(11) 0.0705(13) 0.0150(10) 0.0451(12) 0.0232(11) C23 0.0548(12) 0.0667(13) 0.0712(13) 0.0251(11) 0.0305(10) 0.0205(10) C24 0.0455(10) 0.0509(10) 0.0523(10) 0.0141(8) 0.0155(8) 0.0024(8) C25 0.0435(9) 0.0365(9) 0.0385(8) 0.0087(7) 0.0156(7) 0.0005(7) C26 0.0448(9) 0.0357(8) 0.0352(8) -0.0004(6) 0.0111(7) -0.0026(7) C27 0.0509(10) 0.0462(10) 0.0400(9) 0.0059(7) 0.0176(8) 0.0046(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4501(13) . ? P1 O3 1.5840(12) . ? P1 O2 1.5940(13) . ? P1 C13 1.7946(16) . ? O2 C12 1.403(2) . ? O3 C1 1.4007(19) . ? O4 C27 1.360(2) . ? O4 N1 1.4732(18) . ? O5 C27 1.195(2) . ? N1 C20 1.441(2) . ? N1 C19 1.472(2) . ? C1 C2 1.381(2) . ? C1 C6 1.384(2) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.371(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.395(2) . ? C5 H5 0.9300 . ? C6 C7 1.479(2) . ? C7 C8 1.389(3) . ? C7 C12 1.393(2) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.373(3) . ? C9 H9 0.9300 . ? C10 C11 1.370(3) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C13 C14 1.339(2) . ? C13 C26 1.536(2) . ? C14 C15 1.511(2) . ? C14 C19 1.518(2) . ? C15 C16 1.511(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.512(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.518(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.527(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9800 . ? C20 C25 1.379(2) . ? C20 C21 1.382(2) . ? C21 C22 1.379(3) . ? C21 H21 0.9300 . ? C22 C23 1.378(3) . ? C22 H22 0.9300 . ? C23 C24 1.388(3) . ? C23 H23 0.9300 . ? C24 C25 1.380(2) . ? C24 H24 0.9300 . ? C25 C26 1.503(2) . ? C26 C27 1.505(2) . ? C26 H26 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O3 116.18(8) . . ? O1 P1 O2 109.64(7) . . ? O3 P1 O2 103.41(6) . . ? O1 P1 C13 117.57(8) . . ? O3 P1 C13 100.52(7) . . ? O2 P1 C13 108.28(7) . . ? C12 O2 P1 119.37(10) . . ? C1 O3 P1 124.44(10) . . ? C27 O4 N1 116.59(12) . . ? C20 N1 C19 115.67(13) . . ? C20 N1 O4 109.23(12) . . ? C19 N1 O4 107.41(12) . . ? C2 C1 C6 123.22(16) . . ? C2 C1 O3 116.87(15) . . ? C6 C1 O3 119.59(14) . . ? C3 C2 C1 119.22(18) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 119.26(18) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.99(18) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 121.34(19) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 115.96(17) . . ? C1 C6 C7 122.36(15) . . ? C5 C6 C7 121.63(17) . . ? C8 C7 C12 116.54(17) . . ? C8 C7 C6 121.12(16) . . ? C12 C7 C6 122.33(16) . . ? C9 C8 C7 121.41(19) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.8(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.59(19) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 122.34(17) . . ? C11 C12 O2 117.91(16) . . ? C7 C12 O2 119.69(15) . . ? C14 C13 C26 121.95(14) . . ? C14 C13 P1 120.67(12) . . ? C26 C13 P1 117.37(11) . . ? C13 C14 C15 124.55(15) . . ? C13 C14 C19 124.52(14) . . ? C15 C14 C19 110.93(14) . . ? C14 C15 C16 113.12(16) . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 111.57(17) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 110.87(16) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 110.88(16) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? N1 C19 C14 118.86(13) . . ? N1 C19 C18 108.07(14) . . ? C14 C19 C18 109.91(15) . . ? N1 C19 H19 106.4 . . ? C14 C19 H19 106.4 . . ? C18 C19 H19 106.4 . . ? C25 C20 C21 121.30(17) . . ? C25 C20 N1 118.24(15) . . ? C21 C20 N1 120.40(16) . . ? C22 C21 C20 118.26(19) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? C23 C22 C21 120.87(18) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 120.64(18) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 118.64(19) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C20 C25 C24 120.26(16) . . ? C20 C25 C26 113.90(14) . . ? C24 C25 C26 125.78(16) . . ? C25 C26 C27 109.57(13) . . ? C25 C26 C13 112.35(13) . . ? C27 C26 C13 107.22(13) . . ? C25 C26 H26 109.2 . . ? C27 C26 H26 109.2 . . ? C13 C26 H26 109.2 . . ? O5 C27 O4 118.30(17) . . ? O5 C27 C26 126.04(17) . . ? O4 C27 C26 115.66(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.248 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.042 #===END data_compound-15 _database_code_depnum_ccdc_archive 'CCDC 804473' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 N O2 P' _chemical_formula_sum 'C26 H26 N O2 P' _chemical_formula_weight 415.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.973(4) _cell_length_b 15.480(6) _cell_length_c 17.629(6) _cell_angle_alpha 90.00 _cell_angle_beta 117.171(16) _cell_angle_gamma 90.00 _cell_volume 2178.5(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2773 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.91 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9824 _exptl_absorpt_process_details 'SADABS, Sheldrick(1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 18647 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3829 _reflns_number_gt 2855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3829 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.28463(7) 0.71937(4) 0.27259(4) 0.01844(17) Uani 1 1 d . . . O1 O 0.42262(19) 0.78214(9) 0.28837(10) 0.0228(4) Uani 1 1 d . . . O2 O 0.54310(19) 0.67461(10) 0.20844(10) 0.0241(4) Uani 1 1 d . . . H2B H 0.5321 0.7192 0.2325 0.036 Uiso 1 1 d R . . N1 N 0.4089(2) 0.44906(11) 0.18732(11) 0.0205(4) Uani 1 1 d . . . H1A H 0.4693 0.4049 0.1925 0.025 Uiso 1 1 d R . . C1 C 0.2927(3) 0.68723(14) 0.37311(14) 0.0200(5) Uani 1 1 d . . . C2 C 0.3816(3) 0.73873(15) 0.44366(15) 0.0253(6) Uani 1 1 d . . . H2 H 0.4342 0.7899 0.4380 0.030 Uiso 1 1 calc R . . C3 C 0.3946(3) 0.71639(17) 0.52254(15) 0.0323(6) Uani 1 1 d . . . H3 H 0.4546 0.7525 0.5706 0.039 Uiso 1 1 calc R . . C4 C 0.3203(3) 0.64183(17) 0.53122(16) 0.0334(7) Uani 1 1 d . . . H4 H 0.3299 0.6262 0.5854 0.040 Uiso 1 1 calc R . . C5 C 0.2320(3) 0.58960(17) 0.46138(17) 0.0344(7) Uani 1 1 d . . . H5 H 0.1812 0.5381 0.4677 0.041 Uiso 1 1 calc R . . C6 C 0.2172(3) 0.61194(16) 0.38237(16) 0.0285(6) Uani 1 1 d . . . H6 H 0.1557 0.5760 0.3344 0.034 Uiso 1 1 calc R . . C7 C 0.0829(3) 0.76654(13) 0.20695(14) 0.0189(5) Uani 1 1 d . . . C8 C -0.0290(3) 0.79034(15) 0.23768(15) 0.0257(6) Uani 1 1 d . . . H8 H -0.0066 0.7755 0.2942 0.031 Uiso 1 1 calc R . . C9 C -0.1724(3) 0.83550(16) 0.18614(16) 0.0308(6) Uani 1 1 d . . . H9 H -0.2480 0.8520 0.2076 0.037 Uiso 1 1 calc R . . C10 C -0.2072(3) 0.85687(15) 0.10359(16) 0.0270(6) Uani 1 1 d . . . H10 H -0.3058 0.8883 0.0686 0.032 Uiso 1 1 calc R . . C11 C -0.0975(3) 0.83230(15) 0.07204(15) 0.0268(6) Uani 1 1 d . . . H11 H -0.1216 0.8462 0.0151 0.032 Uiso 1 1 calc R . . C12 C 0.0465(3) 0.78757(14) 0.12348(14) 0.0230(5) Uani 1 1 d . . . H12 H 0.1216 0.7709 0.1017 0.028 Uiso 1 1 calc R . . C13 C 0.3022(3) 0.62314(13) 0.21998(14) 0.0173(5) Uani 1 1 d . . . C14 C 0.1590(3) 0.58012(14) 0.17288(14) 0.0193(5) Uani 1 1 d . . . H14 H 0.0621 0.6115 0.1651 0.023 Uiso 1 1 calc R . . C15 C 0.1197(3) 0.49601(13) 0.13108(14) 0.0177(5) Uani 1 1 d . . . C16 C -0.0493(3) 0.47546(14) 0.08409(14) 0.0202(5) Uani 1 1 d . . . H16 H -0.1306 0.5189 0.0750 0.024 Uiso 1 1 calc R . . C17 C -0.1025(3) 0.39466(14) 0.05043(14) 0.0231(5) Uani 1 1 d . . . H17 H -0.2185 0.3822 0.0184 0.028 Uiso 1 1 calc R . . C18 C 0.0175(3) 0.33166(14) 0.06435(14) 0.0232(5) Uani 1 1 d . . . H18 H -0.0170 0.2749 0.0430 0.028 Uiso 1 1 calc R . . C19 C 0.1844(3) 0.35000(14) 0.10823(14) 0.0209(5) Uani 1 1 d . . . H19 H 0.2641 0.3061 0.1161 0.025 Uiso 1 1 calc R . . C20 C 0.2401(3) 0.43258(14) 0.14186(14) 0.0189(5) Uani 1 1 d . . . C21 C 0.4787(3) 0.52970(14) 0.17409(15) 0.0218(5) Uani 1 1 d . . . H21 H 0.4087 0.5492 0.1140 0.026 Uiso 1 1 calc R . . C22 C 0.6566(3) 0.51347(15) 0.18732(15) 0.0274(6) Uani 1 1 d . . . H22A H 0.6554 0.4657 0.1497 0.033 Uiso 1 1 calc R . . H22B H 0.6984 0.5659 0.1710 0.033 Uiso 1 1 calc R . . C23 C 0.7747(3) 0.49055(15) 0.27927(16) 0.0296(6) Uani 1 1 d . . . H23A H 0.8899 0.4842 0.2860 0.036 Uiso 1 1 calc R . . H23B H 0.7408 0.4345 0.2937 0.036 Uiso 1 1 calc R . . C24 C 0.7729(3) 0.55989(16) 0.34024(15) 0.0289(6) Uani 1 1 d . . . H24A H 0.8223 0.6137 0.3313 0.035 Uiso 1 1 calc R . . H24B H 0.8426 0.5407 0.3997 0.035 Uiso 1 1 calc R . . C25 C 0.5955(3) 0.57812(15) 0.32677(14) 0.0243(6) Uani 1 1 d . . . H25A H 0.5516 0.5265 0.3431 0.029 Uiso 1 1 calc R . . H25B H 0.5980 0.6265 0.3641 0.029 Uiso 1 1 calc R . . C26 C 0.4792(3) 0.60116(13) 0.23438(14) 0.0189(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0192(3) 0.0172(3) 0.0196(3) -0.0017(3) 0.0095(3) -0.0007(3) O1 0.0220(9) 0.0179(8) 0.0280(9) -0.0029(7) 0.0110(8) -0.0030(7) O2 0.0269(10) 0.0204(9) 0.0306(10) 0.0014(7) 0.0181(8) -0.0025(7) N1 0.0188(11) 0.0168(10) 0.0252(11) -0.0018(8) 0.0095(9) 0.0017(8) C1 0.0174(13) 0.0250(13) 0.0182(13) 0.0001(10) 0.0087(11) 0.0053(10) C2 0.0241(14) 0.0247(13) 0.0230(13) -0.0010(11) 0.0071(11) 0.0073(11) C3 0.0330(16) 0.0379(15) 0.0194(13) -0.0028(12) 0.0062(12) 0.0155(13) C4 0.0389(17) 0.0436(17) 0.0226(14) 0.0100(12) 0.0182(13) 0.0199(13) C5 0.0385(17) 0.0359(15) 0.0368(16) 0.0076(13) 0.0240(14) 0.0046(13) C6 0.0290(15) 0.0338(15) 0.0249(14) -0.0001(11) 0.0142(12) -0.0007(12) C7 0.0215(13) 0.0138(11) 0.0211(12) -0.0044(10) 0.0094(11) -0.0052(10) C8 0.0267(14) 0.0311(14) 0.0221(13) -0.0003(11) 0.0137(12) 0.0047(11) C9 0.0260(15) 0.0370(15) 0.0344(16) -0.0057(12) 0.0180(13) 0.0036(12) C10 0.0199(14) 0.0243(13) 0.0308(15) -0.0004(11) 0.0062(12) 0.0027(11) C11 0.0285(15) 0.0273(14) 0.0208(13) 0.0029(11) 0.0079(12) 0.0002(11) C12 0.0235(14) 0.0245(13) 0.0226(13) -0.0009(11) 0.0120(12) 0.0009(11) C13 0.0194(13) 0.0166(12) 0.0179(12) 0.0022(9) 0.0102(11) 0.0007(10) C14 0.0211(13) 0.0185(12) 0.0216(13) 0.0029(10) 0.0126(11) 0.0042(10) C15 0.0220(13) 0.0169(12) 0.0183(12) 0.0008(9) 0.0127(11) -0.0014(10) C16 0.0197(13) 0.0207(12) 0.0211(13) 0.0003(10) 0.0102(11) 0.0001(10) C17 0.0206(13) 0.0263(14) 0.0203(13) -0.0005(10) 0.0076(11) -0.0045(11) C18 0.0307(15) 0.0198(12) 0.0192(13) -0.0040(10) 0.0114(12) -0.0060(11) C19 0.0221(14) 0.0197(12) 0.0202(13) -0.0023(10) 0.0091(11) 0.0015(10) C20 0.0190(13) 0.0241(13) 0.0142(12) 0.0015(10) 0.0083(10) -0.0008(10) C21 0.0215(13) 0.0249(13) 0.0201(13) 0.0011(10) 0.0105(11) -0.0003(10) C22 0.0280(15) 0.0262(13) 0.0337(15) -0.0040(11) 0.0190(13) 0.0005(11) C23 0.0188(14) 0.0276(14) 0.0397(16) -0.0020(12) 0.0109(13) 0.0029(11) C24 0.0218(14) 0.0316(14) 0.0261(14) -0.0004(11) 0.0047(12) 0.0009(11) C25 0.0238(14) 0.0269(13) 0.0212(13) 0.0009(11) 0.0094(11) -0.0012(11) C26 0.0184(13) 0.0171(12) 0.0212(13) 0.0025(10) 0.0089(11) -0.0015(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4967(16) . ? P1 C7 1.799(2) . ? P1 C13 1.799(2) . ? P1 C1 1.810(2) . ? O2 C26 1.439(2) . ? O2 H2B 0.8400 . ? N1 C20 1.376(3) . ? N1 C21 1.462(3) . ? N1 H1A 0.8513 . ? C1 C2 1.383(3) . ? C1 C6 1.395(3) . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 C4 1.376(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.391(3) . ? C7 C12 1.392(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.382(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.345(3) . ? C13 C26 1.528(3) . ? C14 C15 1.458(3) . ? C14 H14 0.9500 . ? C15 C16 1.393(3) . ? C15 C20 1.407(3) . ? C16 C17 1.373(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.365(3) . ? C18 H18 0.9500 . ? C19 C20 1.402(3) . ? C19 H19 0.9500 . ? C21 C22 1.525(3) . ? C21 C26 1.533(3) . ? C21 H21 1.0000 . ? C22 C23 1.519(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.524(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.525(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.522(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C7 111.10(10) . . ? O1 P1 C13 111.93(10) . . ? C7 P1 C13 107.68(10) . . ? O1 P1 C1 109.67(10) . . ? C7 P1 C1 108.67(10) . . ? C13 P1 C1 107.66(10) . . ? C26 O2 H2B 109.5 . . ? C20 N1 C21 120.21(18) . . ? C20 N1 H1A 113.1 . . ? C21 N1 H1A 113.9 . . ? C2 C1 C6 119.2(2) . . ? C2 C1 P1 118.10(18) . . ? C6 C1 P1 122.68(17) . . ? C1 C2 C3 120.6(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.9(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 C7 C12 119.1(2) . . ? C8 C7 P1 123.38(18) . . ? C12 C7 P1 117.16(17) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 120.6(2) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C26 128.3(2) . . ? C14 C13 P1 116.39(17) . . ? C26 C13 P1 115.33(15) . . ? C13 C14 C15 134.2(2) . . ? C13 C14 H14 112.9 . . ? C15 C14 H14 112.9 . . ? C16 C15 C20 118.8(2) . . ? C16 C15 C14 116.8(2) . . ? C20 C15 C14 124.1(2) . . ? C17 C16 C15 122.3(2) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 118.3(2) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C19 C18 C17 121.0(2) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 121.1(2) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? N1 C20 C19 120.0(2) . . ? N1 C20 C15 121.5(2) . . ? C19 C20 C15 118.4(2) . . ? N1 C21 C22 109.25(18) . . ? N1 C21 C26 111.79(17) . . ? C22 C21 C26 109.97(19) . . ? N1 C21 H21 108.6 . . ? C22 C21 H21 108.6 . . ? C26 C21 H21 108.6 . . ? C23 C22 C21 111.89(19) . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C22 C23 C24 111.2(2) . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C25 111.5(2) . . ? C23 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? C23 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C24 111.53(19) . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? C24 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? O2 C26 C25 110.32(18) . . ? O2 C26 C13 107.83(17) . . ? C25 C26 C13 112.51(18) . . ? O2 C26 C21 103.01(17) . . ? C25 C26 C21 110.88(18) . . ? C13 C26 C21 111.84(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2B O1 0.84 1.94 2.705(2) 150.8 1 N1 H1A O1 0.85 2.09 2.925(2) 166.8 2_645 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.336 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.053 #===END data_compound-16 _database_code_depnum_ccdc_archive 'CCDC 804474' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C20 H20 N O5 P), C H2 Cl2 ' _chemical_formula_sum 'C41 H42 Cl2 N2 O10 P2 ' _chemical_formula_weight 855.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 23.992(9) _cell_length_b 14.574(6) _cell_length_c 11.636(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.284(6) _cell_angle_gamma 90.00 _cell_volume 4065(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8099 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.90 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9372 _exptl_absorpt_correction_T_max 0.9594 _exptl_absorpt_process_details 'SADABS, Sheldrick(1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 33205 _diffrn_reflns_av_R_equivalents 0.1048 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7050 _reflns_number_gt 4534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7050 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.38906(4) 0.67100(6) 0.45522(8) 0.0164(2) Uani 1 1 d . . . O1 O 0.41533(10) 0.59608(17) 0.3941(2) 0.0234(6) Uani 1 1 d . . . O2 O 0.37406(10) 0.75259(17) 0.37223(19) 0.0190(6) Uani 1 1 d . . . O3 O 0.42995(9) 0.71119(16) 0.5520(2) 0.0182(6) Uani 1 1 d . . . O4 O 0.22192(10) 0.56494(18) 0.6259(2) 0.0232(6) Uani 1 1 d . . . O5 O 0.24474(11) 0.41520(19) 0.7762(2) 0.0287(7) Uani 1 1 d . . . H5D H 0.2217 0.3872 0.7328 0.043 Uiso 1 1 calc R . . N1 N 0.28251(11) 0.4608(2) 0.7104(2) 0.0187(7) Uani 1 1 d . . . C1 C 0.36802(15) 0.8468(2) 0.4135(3) 0.0202(8) Uani 1 1 d . . . H1A H 0.3312 0.8534 0.4481 0.024 Uiso 1 1 calc R . . H1B H 0.3690 0.8893 0.3473 0.024 Uiso 1 1 calc R . . C2 C 0.41356(15) 0.8735(3) 0.5020(3) 0.0207(9) Uani 1 1 d . . . C3 C 0.41709(15) 0.8017(3) 0.5972(3) 0.0199(8) Uani 1 1 d . . . H3A H 0.4464 0.8197 0.6552 0.024 Uiso 1 1 calc R . . H3B H 0.3811 0.7992 0.6358 0.024 Uiso 1 1 calc R . . C4 C 0.46987(15) 0.8808(3) 0.4450(3) 0.0257(9) Uani 1 1 d . . . H4A H 0.4682 0.9302 0.3878 0.039 Uiso 1 1 calc R . . H4B H 0.4782 0.8227 0.4070 0.039 Uiso 1 1 calc R . . H4C H 0.4992 0.8943 0.5036 0.039 Uiso 1 1 calc R . . C5 C 0.39780(17) 0.9642(3) 0.5552(4) 0.0315(10) Uani 1 1 d . . . H5A H 0.3628 0.9570 0.5949 0.047 Uiso 1 1 calc R . . H5B H 0.3930 1.0106 0.4947 0.047 Uiso 1 1 calc R . . H5C H 0.4274 0.9835 0.6104 0.047 Uiso 1 1 calc R . . C6 C 0.32562(14) 0.6391(2) 0.5246(3) 0.0153(8) Uani 1 1 d . . . C7 C 0.32386(14) 0.5667(2) 0.5965(3) 0.0145(8) Uani 1 1 d . . . C8 C 0.36679(14) 0.5037(2) 0.6454(3) 0.0147(8) Uani 1 1 d . . . C9 C 0.42406(14) 0.4970(2) 0.6413(3) 0.0175(8) Uani 1 1 d . . . H9 H 0.4440 0.5387 0.5956 0.021 Uiso 1 1 calc R . . C10 C 0.45262(15) 0.4291(3) 0.7039(3) 0.0200(8) Uani 1 1 d . . . H10 H 0.4920 0.4243 0.7001 0.024 Uiso 1 1 calc R . . C11 C 0.42388(15) 0.3686(3) 0.7717(3) 0.0201(8) Uani 1 1 d . . . H11 H 0.4438 0.3220 0.8131 0.024 Uiso 1 1 calc R . . C12 C 0.36649(15) 0.3748(3) 0.7804(3) 0.0206(9) Uani 1 1 d . . . H12 H 0.3468 0.3346 0.8286 0.025 Uiso 1 1 calc R . . C13 C 0.33919(14) 0.4418(2) 0.7158(3) 0.0167(8) Uani 1 1 d . . . C14 C 0.26891(14) 0.5352(2) 0.6442(3) 0.0157(8) Uani 1 1 d . . . C15 C 0.27737(14) 0.7022(2) 0.5029(3) 0.0158(8) Uani 1 1 d . . . C16 C 0.24901(14) 0.7071(3) 0.3961(3) 0.0199(9) Uani 1 1 d . . . H16 H 0.2570 0.6644 0.3373 0.024 Uiso 1 1 calc R . . C17 C 0.20921(16) 0.7744(3) 0.3764(3) 0.0255(9) Uani 1 1 d . . . H17 H 0.1895 0.7772 0.3040 0.031 Uiso 1 1 calc R . . C18 C 0.19772(16) 0.8375(3) 0.4605(3) 0.0289(10) Uani 1 1 d . . . H18 H 0.1713 0.8849 0.4451 0.035 Uiso 1 1 calc R . . C19 C 0.22498(16) 0.8314(3) 0.5681(3) 0.0259(9) Uani 1 1 d . . . H19 H 0.2164 0.8734 0.6272 0.031 Uiso 1 1 calc R . . C20 C 0.26446(15) 0.7642(3) 0.5886(3) 0.0218(9) Uani 1 1 d . . . H20 H 0.2831 0.7602 0.6620 0.026 Uiso 1 1 calc R . . P2 P 0.15661(4) 0.31910(7) 0.50911(8) 0.0184(2) Uani 1 1 d . . . O6 O 0.17642(10) 0.32888(18) 0.6298(2) 0.0252(6) Uani 1 1 d . . . O7 O 0.15400(10) 0.21560(17) 0.4734(2) 0.0194(6) Uani 1 1 d . . . O8 O 0.09544(10) 0.35559(17) 0.4908(2) 0.0206(6) Uani 1 1 d . . . O9 O 0.28146(10) 0.49106(18) 0.2764(2) 0.0232(6) Uani 1 1 d . . . O10 O 0.39349(10) 0.43068(19) 0.3228(2) 0.0276(7) Uani 1 1 d . . . H10B H 0.4050 0.4814 0.3485 0.041 Uiso 1 1 calc R . . N2 N 0.34651(11) 0.4049(2) 0.3792(2) 0.0183(7) Uani 1 1 d . . . C21 C 0.12002(15) 0.1896(3) 0.3709(3) 0.0216(9) Uani 1 1 d . . . H21A H 0.1212 0.1222 0.3612 0.026 Uiso 1 1 calc R . . H21B H 0.1358 0.2180 0.3021 0.026 Uiso 1 1 calc R . . C22 C 0.05979(15) 0.2204(3) 0.3805(3) 0.0197(9) Uani 1 1 d . . . C23 C 0.05888(15) 0.3240(3) 0.3944(3) 0.0228(9) Uani 1 1 d . . . H23A H 0.0708 0.3529 0.3225 0.027 Uiso 1 1 calc R . . H23B H 0.0202 0.3440 0.4072 0.027 Uiso 1 1 calc R . . C24 C 0.03262(15) 0.1726(3) 0.4800(3) 0.0216(9) Uani 1 1 d . . . H24A H 0.0543 0.1850 0.5516 0.032 Uiso 1 1 calc R . . H24B H 0.0316 0.1063 0.4660 0.032 Uiso 1 1 calc R . . H24C H -0.0055 0.1956 0.4868 0.032 Uiso 1 1 calc R . . C25 C 0.02814(16) 0.1970(3) 0.2670(3) 0.0279(10) Uani 1 1 d . . . H25A H -0.0094 0.2236 0.2672 0.042 Uiso 1 1 calc R . . H25B H 0.0253 0.1303 0.2588 0.042 Uiso 1 1 calc R . . H25C H 0.0482 0.2224 0.2025 0.042 Uiso 1 1 calc R . . C26 C 0.19997(14) 0.3806(2) 0.4102(3) 0.0148(8) Uani 1 1 d . . . C27 C 0.25537(14) 0.3678(2) 0.4115(3) 0.0163(8) Uani 1 1 d . . . C28 C 0.29335(14) 0.3042(2) 0.4755(3) 0.0165(8) Uani 1 1 d . . . C29 C 0.28557(15) 0.2279(3) 0.5433(3) 0.0203(9) Uani 1 1 d . . . H29 H 0.2490 0.2074 0.5583 0.024 Uiso 1 1 calc R . . C30 C 0.33159(15) 0.1814(3) 0.5892(3) 0.0209(9) Uani 1 1 d . . . H30 H 0.3263 0.1286 0.6354 0.025 Uiso 1 1 calc R . . C31 C 0.38513(15) 0.2109(3) 0.5689(3) 0.0201(9) Uani 1 1 d . . . H31 H 0.4160 0.1788 0.6032 0.024 Uiso 1 1 calc R . . C32 C 0.39461(15) 0.2858(3) 0.4998(3) 0.0191(8) Uani 1 1 d . . . H32 H 0.4313 0.3058 0.4849 0.023 Uiso 1 1 calc R . . C33 C 0.34837(14) 0.3299(2) 0.4535(3) 0.0166(8) Uani 1 1 d . . . C34 C 0.29352(15) 0.4301(3) 0.3447(3) 0.0185(8) Uani 1 1 d . . . C35 C 0.16999(14) 0.4457(2) 0.3304(3) 0.0174(8) Uani 1 1 d . . . C36 C 0.16171(15) 0.4223(3) 0.2147(3) 0.0202(9) Uani 1 1 d . . . H36 H 0.1772 0.3673 0.1862 0.024 Uiso 1 1 calc R . . C37 C 0.13079(15) 0.4797(3) 0.1412(3) 0.0221(9) Uani 1 1 d . . . H37 H 0.1257 0.4640 0.0622 0.027 Uiso 1 1 calc R . . C38 C 0.10730(15) 0.5594(3) 0.1818(3) 0.0253(9) Uani 1 1 d . . . H38 H 0.0856 0.5978 0.1316 0.030 Uiso 1 1 calc R . . C39 C 0.11582(15) 0.5825(3) 0.2967(3) 0.0237(9) Uani 1 1 d . . . H39 H 0.1003 0.6375 0.3251 0.028 Uiso 1 1 calc R . . C40 C 0.14686(15) 0.5259(3) 0.3706(3) 0.0204(8) Uani 1 1 d . . . H40 H 0.1523 0.5423 0.4492 0.025 Uiso 1 1 calc R . . Cl1 Cl 0.94075(4) 0.07009(8) 0.69049(9) 0.0386(3) Uani 1 1 d . . . Cl2 Cl 0.89859(4) 0.17091(7) 0.88547(9) 0.0325(3) Uani 1 1 d . . . C41 C 0.89966(18) 0.0650(3) 0.8132(4) 0.0355(11) Uani 1 1 d . . . H41A H 0.8611 0.0473 0.7894 0.043 Uiso 1 1 calc R . . H41B H 0.9148 0.0172 0.8663 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0228(5) 0.0131(5) 0.0134(5) 0.0008(4) 0.0028(4) -0.0005(4) O1 0.0297(15) 0.0197(15) 0.0214(14) -0.0025(12) 0.0071(12) -0.0006(11) O2 0.0286(14) 0.0148(14) 0.0138(13) 0.0011(11) 0.0022(11) -0.0012(11) O3 0.0231(13) 0.0133(14) 0.0179(13) 0.0018(11) -0.0023(11) -0.0015(11) O4 0.0221(15) 0.0260(16) 0.0218(15) 0.0067(12) 0.0028(11) 0.0000(12) O5 0.0327(16) 0.0324(18) 0.0213(15) 0.0028(13) 0.0028(12) -0.0095(13) N1 0.0192(16) 0.0203(18) 0.0169(16) 0.0077(14) 0.0040(13) -0.0015(13) C1 0.030(2) 0.012(2) 0.019(2) 0.0015(16) 0.0014(17) 0.0000(16) C2 0.025(2) 0.016(2) 0.022(2) 0.0032(17) 0.0027(17) -0.0034(16) C3 0.028(2) 0.017(2) 0.0144(19) -0.0030(16) -0.0012(16) -0.0032(16) C4 0.034(2) 0.020(2) 0.023(2) 0.0042(18) -0.0009(18) -0.0054(18) C5 0.044(3) 0.019(2) 0.032(2) -0.0070(19) 0.003(2) -0.0045(19) C6 0.0207(19) 0.017(2) 0.0082(17) -0.0019(15) -0.0003(14) 0.0006(15) C7 0.0227(19) 0.011(2) 0.0094(17) -0.0043(15) 0.0008(15) -0.0005(15) C8 0.024(2) 0.012(2) 0.0080(17) -0.0007(14) -0.0018(15) -0.0008(15) C9 0.027(2) 0.013(2) 0.0120(18) 0.0003(15) 0.0035(16) -0.0017(16) C10 0.0204(19) 0.021(2) 0.018(2) -0.0027(17) -0.0032(16) 0.0012(16) C11 0.031(2) 0.015(2) 0.0140(19) -0.0001(16) -0.0022(16) 0.0034(17) C12 0.035(2) 0.012(2) 0.0147(19) 0.0041(16) -0.0002(17) -0.0028(17) C13 0.026(2) 0.016(2) 0.0082(17) -0.0027(15) -0.0012(15) -0.0026(16) C14 0.021(2) 0.015(2) 0.0109(18) -0.0029(15) 0.0030(15) -0.0006(16) C15 0.0185(18) 0.015(2) 0.0142(18) 0.0041(15) 0.0013(15) -0.0015(15) C16 0.027(2) 0.022(2) 0.0107(18) -0.0020(16) -0.0005(16) 0.0012(17) C17 0.030(2) 0.029(2) 0.017(2) 0.0042(18) -0.0055(17) 0.0054(18) C18 0.032(2) 0.028(3) 0.026(2) 0.0043(19) -0.0032(18) 0.0144(19) C19 0.032(2) 0.029(3) 0.017(2) -0.0029(18) 0.0020(17) 0.0064(18) C20 0.027(2) 0.026(2) 0.0127(19) -0.0020(17) 0.0029(16) 0.0041(17) P2 0.0227(5) 0.0191(6) 0.0135(5) 0.0013(4) 0.0038(4) -0.0019(4) O6 0.0307(15) 0.0349(17) 0.0099(13) 0.0003(12) 0.0012(11) -0.0064(13) O7 0.0241(14) 0.0169(15) 0.0171(13) 0.0033(11) 0.0010(11) -0.0008(11) O8 0.0243(14) 0.0214(15) 0.0164(13) -0.0008(11) 0.0040(11) -0.0025(11) O9 0.0296(15) 0.0205(16) 0.0196(14) 0.0063(12) 0.0024(12) -0.0011(12) O10 0.0313(15) 0.0244(17) 0.0275(16) -0.0026(13) 0.0071(13) -0.0061(12) N2 0.0178(16) 0.0201(18) 0.0170(16) 0.0012(14) 0.0032(13) -0.0029(13) C21 0.032(2) 0.023(2) 0.0094(18) -0.0023(16) 0.0010(16) -0.0046(17) C22 0.029(2) 0.019(2) 0.0110(18) -0.0033(16) 0.0024(16) -0.0037(17) C23 0.0206(19) 0.025(2) 0.023(2) 0.0008(18) -0.0009(16) -0.0040(17) C24 0.025(2) 0.021(2) 0.019(2) -0.0008(17) 0.0033(16) -0.0017(17) C25 0.034(2) 0.032(3) 0.018(2) 0.0008(18) -0.0001(17) -0.0030(19) C26 0.025(2) 0.011(2) 0.0088(17) 0.0016(15) -0.0004(15) -0.0022(15) C27 0.025(2) 0.011(2) 0.0126(18) 0.0000(15) 0.0014(15) -0.0003(15) C28 0.025(2) 0.012(2) 0.0125(18) -0.0019(15) 0.0012(15) 0.0015(15) C29 0.023(2) 0.020(2) 0.018(2) -0.0007(17) 0.0006(16) -0.0032(16) C30 0.032(2) 0.017(2) 0.0140(19) 0.0008(16) 0.0010(16) 0.0047(17) C31 0.028(2) 0.016(2) 0.0155(19) -0.0040(16) -0.0046(16) 0.0080(16) C32 0.020(2) 0.021(2) 0.0157(19) -0.0068(17) 0.0019(16) -0.0015(16) C33 0.024(2) 0.018(2) 0.0069(17) -0.0042(15) 0.0012(15) -0.0008(16) C34 0.031(2) 0.014(2) 0.0112(18) -0.0026(16) 0.0054(16) -0.0024(16) C35 0.0212(19) 0.017(2) 0.0139(19) 0.0008(16) 0.0011(15) -0.0043(16) C36 0.027(2) 0.019(2) 0.0146(19) -0.0037(16) 0.0036(16) -0.0047(17) C37 0.032(2) 0.024(2) 0.0110(19) 0.0040(17) -0.0017(16) -0.0043(18) C38 0.025(2) 0.030(3) 0.019(2) 0.0081(18) -0.0056(17) 0.0005(18) C39 0.027(2) 0.019(2) 0.024(2) 0.0016(18) 0.0000(17) 0.0052(17) C40 0.027(2) 0.022(2) 0.0124(18) -0.0004(17) 0.0006(16) 0.0006(17) Cl1 0.0394(6) 0.0421(7) 0.0351(6) -0.0023(5) 0.0125(5) -0.0035(5) Cl2 0.0306(6) 0.0342(7) 0.0328(6) -0.0005(5) 0.0045(5) -0.0044(5) C41 0.038(2) 0.028(3) 0.042(3) 0.000(2) 0.018(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.460(3) . ? P1 O2 1.565(3) . ? P1 O3 1.576(3) . ? P1 C6 1.812(3) . ? O2 C1 1.463(4) . ? O3 C3 1.458(4) . ? O4 C14 1.218(4) . ? O5 N1 1.380(4) . ? O5 H5D 0.8400 . ? N1 C14 1.362(5) . ? N1 C13 1.387(4) . ? C1 C2 1.522(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.513(5) . ? C2 C3 1.523(5) . ? C2 C4 1.533(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.348(5) . ? C6 C15 1.493(5) . ? C7 C8 1.477(5) . ? C7 C14 1.522(5) . ? C8 C9 1.380(5) . ? C8 C13 1.402(5) . ? C9 C10 1.392(5) . ? C9 H9 0.9500 . ? C10 C11 1.386(5) . ? C10 H10 0.9500 . ? C11 C12 1.387(5) . ? C11 H11 0.9500 . ? C12 C13 1.382(5) . ? C12 H12 0.9500 . ? C15 C20 1.389(5) . ? C15 C16 1.394(5) . ? C16 C17 1.382(5) . ? C16 H16 0.9500 . ? C17 C18 1.378(5) . ? C17 H17 0.9500 . ? C18 C19 1.392(5) . ? C18 H18 0.9500 . ? C19 C20 1.376(5) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? P2 O6 1.472(3) . ? P2 O7 1.565(3) . ? P2 O8 1.568(3) . ? P2 C26 1.818(3) . ? O7 C21 1.467(4) . ? O8 C23 1.470(4) . ? O9 C34 1.219(4) . ? O10 N2 1.379(3) . ? O10 H10B 0.8400 . ? N2 C34 1.368(5) . ? N2 C33 1.393(5) . ? C21 C22 1.521(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.518(5) . ? C22 C24 1.521(5) . ? C22 C25 1.535(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.342(5) . ? C26 C35 1.492(5) . ? C27 C28 1.479(5) . ? C27 C34 1.525(5) . ? C28 C29 1.381(5) . ? C28 C33 1.405(5) . ? C29 C30 1.384(5) . ? C29 H29 0.9500 . ? C30 C31 1.384(5) . ? C30 H30 0.9500 . ? C31 C32 1.381(5) . ? C31 H31 0.9500 . ? C32 C33 1.374(5) . ? C32 H32 0.9500 . ? C35 C40 1.383(5) . ? C35 C36 1.396(5) . ? C36 C37 1.389(5) . ? C36 H36 0.9500 . ? C37 C38 1.382(5) . ? C37 H37 0.9500 . ? C38 C39 1.386(5) . ? C38 H38 0.9500 . ? C39 C40 1.386(5) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? Cl1 C41 1.769(4) . ? Cl2 C41 1.759(4) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 111.17(14) . . ? O1 P1 O3 110.93(15) . . ? O2 P1 O3 106.24(14) . . ? O1 P1 C6 114.31(16) . . ? O2 P1 C6 107.07(15) . . ? O3 P1 C6 106.69(14) . . ? C1 O2 P1 122.3(2) . . ? C3 O3 P1 117.4(2) . . ? N1 O5 H5D 109.5 . . ? C14 N1 O5 123.3(3) . . ? C14 N1 C13 113.4(3) . . ? O5 N1 C13 122.9(3) . . ? O2 C1 C2 112.6(3) . . ? O2 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O2 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C5 C2 C1 108.4(3) . . ? C5 C2 C3 108.0(3) . . ? C1 C2 C3 109.5(3) . . ? C5 C2 C4 110.8(3) . . ? C1 C2 C4 110.2(3) . . ? C3 C2 C4 109.8(3) . . ? O3 C3 C2 111.4(3) . . ? O3 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? O3 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C15 123.0(3) . . ? C7 C6 P1 121.7(3) . . ? C15 C6 P1 115.2(2) . . ? C6 C7 C8 133.4(3) . . ? C6 C7 C14 120.8(3) . . ? C8 C7 C14 105.8(3) . . ? C9 C8 C13 118.0(3) . . ? C9 C8 C7 135.3(3) . . ? C13 C8 C7 106.7(3) . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 117.2(3) . . ? C13 C12 H12 121.4 . . ? C11 C12 H12 121.4 . . ? C12 C13 N1 127.5(3) . . ? C12 C13 C8 123.2(3) . . ? N1 C13 C8 109.3(3) . . ? O4 C14 N1 125.5(3) . . ? O4 C14 C7 129.7(3) . . ? N1 C14 C7 104.8(3) . . ? C20 C15 C16 119.5(3) . . ? C20 C15 C6 118.3(3) . . ? C16 C15 C6 122.0(3) . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.8(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.7(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.8(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 120.7(4) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? O6 P2 O7 110.79(15) . . ? O6 P2 O8 111.23(14) . . ? O7 P2 O8 105.28(14) . . ? O6 P2 C26 112.65(16) . . ? O7 P2 C26 108.96(15) . . ? O8 P2 C26 107.63(15) . . ? C21 O7 P2 118.7(2) . . ? C23 O8 P2 121.6(2) . . ? N2 O10 H10B 109.5 . . ? C34 N2 O10 123.7(3) . . ? C34 N2 C33 113.5(3) . . ? O10 N2 C33 120.2(3) . . ? O7 C21 C22 111.3(3) . . ? O7 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? O7 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C24 111.5(3) . . ? C23 C22 C21 108.6(3) . . ? C24 C22 C21 111.0(3) . . ? C23 C22 C25 107.7(3) . . ? C24 C22 C25 110.0(3) . . ? C21 C22 C25 108.1(3) . . ? O8 C23 C22 112.5(3) . . ? O8 C23 H23A 109.1 . . ? C22 C23 H23A 109.1 . . ? O8 C23 H23B 109.1 . . ? C22 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C35 123.3(3) . . ? C27 C26 P2 121.0(3) . . ? C35 C26 P2 115.7(2) . . ? C26 C27 C28 133.1(3) . . ? C26 C27 C34 121.7(3) . . ? C28 C27 C34 105.0(3) . . ? C29 C28 C33 117.9(3) . . ? C29 C28 C27 134.2(3) . . ? C33 C28 C27 107.8(3) . . ? C28 C29 C30 119.4(3) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C31 C30 C29 120.9(3) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C32 C31 C30 121.4(3) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? C33 C32 C31 116.7(3) . . ? C33 C32 H32 121.6 . . ? C31 C32 H32 121.6 . . ? C32 C33 N2 128.0(3) . . ? C32 C33 C28 123.6(3) . . ? N2 C33 C28 108.4(3) . . ? O9 C34 N2 125.5(3) . . ? O9 C34 C27 129.4(3) . . ? N2 C34 C27 105.1(3) . . ? C40 C35 C36 119.3(3) . . ? C40 C35 C26 121.1(3) . . ? C36 C35 C26 119.4(3) . . ? C37 C36 C35 119.9(4) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C38 C37 C36 120.7(4) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C37 C38 C39 119.2(4) . . ? C37 C38 H38 120.4 . . ? C39 C38 H38 120.4 . . ? C38 C39 C40 120.6(4) . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C35 C40 C39 120.4(3) . . ? C35 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? Cl2 C41 Cl1 111.6(2) . . ? Cl2 C41 H41A 109.3 . . ? Cl1 C41 H41A 109.3 . . ? Cl2 C41 H41B 109.3 . . ? Cl1 C41 H41B 109.3 . . ? H41A C41 H41B 108.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5D O6 0.84 1.80 2.635(4) 174.9 1 O10 H10B O1 0.84 1.77 2.596(4) 168.3 1 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.711 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.097 #===END data_compound-22 _database_code_depnum_ccdc_archive 'CCDC 804475' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H48 Cl2 O14 P2' _chemical_formula_weight 897.63 _chemical_absolute_configuration rm 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.3587(9) _cell_length_b 18.5030(13) _cell_length_c 20.2698(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4260.1(5) _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 needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9544 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 17654 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 24.99 _reflns_number_total 7420 _reflns_number_gt 5765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _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^)+(0.0785P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_ls_number_reflns 7420 _refine_ls_number_parameters 540 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.78662(8) 0.90526(5) 0.12326(4) 0.0320(2) Uani 1 1 d . . . P2 P 0.90941(8) 0.97360(5) -0.07201(4) 0.0339(2) Uani 1 1 d . . . O1 O 0.6653(2) 0.87897(14) 0.11912(11) 0.0479(6) Uani 1 1 d . . . O2 O 0.8155(2) 0.94430(11) 0.19147(9) 0.0374(6) Uani 1 1 d . . . O3 O 0.8833(2) 0.84392(12) 0.11928(10) 0.0426(6) Uani 1 1 d . . . O4 O 0.9310(2) 1.05133(13) -0.07404(11) 0.0508(7) Uani 1 1 d . . . O5 O 0.8640(2) 0.94204(13) -0.14015(9) 0.0405(6) Uani 1 1 d . . . O6 O 1.0205(2) 0.92511(14) -0.05615(10) 0.0456(6) Uani 1 1 d . . . O7 O 0.8049(3) 1.23405(15) 0.15092(14) 0.0745(9) Uani 1 1 d . . . O8 O 0.7382(2) 1.14524(14) 0.21340(11) 0.0524(7) Uani 1 1 d . . . O9 O 0.6197(3) 1.20432(18) 0.00668(14) 0.0811(11) Uani 1 1 d . . . O10 O 0.5312(3) 1.20869(16) 0.10509(14) 0.0705(8) Uani 1 1 d . . . O11 O 0.4069(3) 1.0527(2) 0.01472(14) 0.0819(10) Uani 1 1 d . . . O12 O 0.3577(3) 1.06404(15) -0.09080(12) 0.0611(8) Uani 1 1 d . . . O13 O 0.4017(2) 0.90369(16) -0.12488(12) 0.0585(7) Uani 1 1 d . . . O14 O 0.5308(2) 0.96773(14) -0.18300(10) 0.0489(6) Uani 1 1 d . . . C1 C 0.8109(4) 0.89452(19) 0.24782(15) 0.0472(9) Uani 1 1 d . . . H1A H 0.7324 0.8742 0.2512 0.057 Uiso 1 1 calc R . . H1B H 0.8268 0.9211 0.2881 0.057 Uiso 1 1 calc R . . C2 C 0.9005(4) 0.83323(19) 0.24075(16) 0.0478(10) Uani 1 1 d . . . C3 C 0.8802(4) 0.79353(19) 0.17517(15) 0.0516(10) Uani 1 1 d . . . H3A H 0.9406 0.7570 0.1694 0.062 Uiso 1 1 calc R . . H3B H 0.8045 0.7694 0.1763 0.062 Uiso 1 1 calc R . . C4 C 1.0253(4) 0.8630(2) 0.2441(2) 0.0656(13) Uani 1 1 d . . . H4A H 1.0376 0.8963 0.2084 0.098 Uiso 1 1 calc R . . H4B H 1.0806 0.8240 0.2408 0.098 Uiso 1 1 calc R . . H4C H 1.0364 0.8876 0.2854 0.098 Uiso 1 1 calc R . . C5 C 0.8786(5) 0.7793(2) 0.29664(19) 0.0781(16) Uani 1 1 d . . . H5A H 0.9364 0.7415 0.2947 0.117 Uiso 1 1 calc R . . H5B H 0.8014 0.7588 0.2920 0.117 Uiso 1 1 calc R . . H5C H 0.8842 0.8037 0.3383 0.117 Uiso 1 1 calc R . . C6 C 0.8264(3) 0.97200(16) 0.06175(13) 0.0297(7) Uani 1 1 d . . . C7 C 0.7295(3) 1.03075(16) 0.05230(13) 0.0284(7) Uani 1 1 d . . . C8 C 0.6482(3) 1.06058(17) 0.10759(15) 0.0352(8) Uani 1 1 d . . . H8A H 0.6636 1.0396 0.1506 0.042 Uiso 1 1 calc R . . H8B H 0.5651 1.0579 0.0969 0.042 Uiso 1 1 calc R . . C9 C 0.7016(3) 1.13731(17) 0.09864(15) 0.0381(8) Uani 1 1 d . . . C10 C 0.7945(3) 1.10477(17) 0.04937(14) 0.0349(7) Uani 1 1 d . . . H10 H 0.7921 1.1272 0.0056 0.042 Uiso 1 1 calc R . . C11 C 0.9176(3) 1.08797(18) 0.07239(14) 0.0358(7) Uani 1 1 d . . . C12 C 1.0100(4) 1.1368(2) 0.08226(15) 0.0480(10) Uani 1 1 d . . . H12 H 0.9970 1.1863 0.0793 0.058 Uiso 1 1 calc R . . C13 C 1.1196(4) 1.1105(2) 0.09632(17) 0.0555(11) Uani 1 1 d . . . H13 H 1.1809 1.1426 0.1046 0.067 Uiso 1 1 calc R . . C14 C 1.1409(3) 1.0364(3) 0.09835(17) 0.0565(11) Uani 1 1 d . . . H14 H 1.2166 1.0195 0.1065 0.068 Uiso 1 1 calc R . . C15 C 1.0500(3) 0.9877(2) 0.08832(15) 0.0425(9) Uani 1 1 d . . . H15 H 1.0640 0.9382 0.0899 0.051 Uiso 1 1 calc R . . C16 C 0.9381(3) 1.01376(17) 0.07596(13) 0.0321(7) Uani 1 1 d . . . C17 C 0.9538(3) 0.9427(2) -0.19193(16) 0.0494(10) Uani 1 1 d . . . H17A H 0.9790 0.9920 -0.1997 0.059 Uiso 1 1 calc R . . H17B H 0.9199 0.9244 -0.2326 0.059 Uiso 1 1 calc R . . C18 C 1.0605(3) 0.8967(3) -0.17329(18) 0.0573(11) Uani 1 1 d . . . C19 C 1.1110(3) 0.9226(3) -0.10833(18) 0.0603(12) Uani 1 1 d . . . H19A H 1.1739 0.8903 -0.0948 0.072 Uiso 1 1 calc R . . H19B H 1.1444 0.9704 -0.1142 0.072 Uiso 1 1 calc R . . C20 C 1.1553(4) 0.9077(4) -0.2272(2) 0.0890(17) Uani 1 1 d . . . H20A H 1.2224 0.8780 -0.2175 0.134 Uiso 1 1 calc R . . H20B H 1.1788 0.9575 -0.2281 0.134 Uiso 1 1 calc R . . H20C H 1.1235 0.8944 -0.2693 0.134 Uiso 1 1 calc R . . C21 C 1.0277(5) 0.8181(3) -0.1698(2) 0.0737(13) Uani 1 1 d . . . H21A H 0.9626 0.8121 -0.1401 0.111 Uiso 1 1 calc R . . H21B H 1.0938 0.7907 -0.1540 0.111 Uiso 1 1 calc R . . H21C H 1.0059 0.8013 -0.2129 0.111 Uiso 1 1 calc R . . C22 C 0.7977(3) 0.94552(16) -0.01299(13) 0.0299(7) Uani 1 1 d . . . C23 C 0.6867(3) 0.99445(16) -0.01112(13) 0.0288(7) Uani 1 1 d . . . C24 C 0.6374(3) 1.03457(19) -0.07269(16) 0.0364(7) Uani 1 1 d . . . H24A H 0.6818 1.0254 -0.1127 0.044 Uiso 1 1 calc R . . H24B H 0.6267 1.0860 -0.0659 0.044 Uiso 1 1 calc R . . C25 C 0.5204(3) 0.99018(18) -0.06801(15) 0.0351(8) Uani 1 1 d . . . C26 C 0.5775(3) 0.94336(18) -0.01137(14) 0.0330(7) Uani 1 1 d . . . H26 H 0.5328 0.9443 0.0300 0.040 Uiso 1 1 calc R . . C27 C 0.6269(3) 0.87031(17) -0.02786(14) 0.0313(7) Uani 1 1 d . . . C28 C 0.5674(3) 0.80562(19) -0.03794(16) 0.0449(9) Uani 1 1 d . . . H28 H 0.4857 0.8052 -0.0410 0.054 Uiso 1 1 calc R . . C29 C 0.6299(4) 0.7422(2) -0.0433(2) 0.0565(11) Uani 1 1 d . . . H29 H 0.5896 0.6991 -0.0503 0.068 Uiso 1 1 calc R . . C30 C 0.7509(4) 0.7412(2) -0.03865(18) 0.0521(10) Uani 1 1 d . . . H30 H 0.7914 0.6976 -0.0416 0.063 Uiso 1 1 calc R . . C31 C 0.8121(3) 0.80522(18) -0.02952(16) 0.0411(8) Uani 1 1 d . . . H31 H 0.8938 0.8050 -0.0269 0.049 Uiso 1 1 calc R . . C32 C 0.7506(3) 0.86903(17) -0.02443(14) 0.0316(7) Uani 1 1 d . . . C33 C 0.6156(4) 1.18762(19) 0.06367(19) 0.0507(10) Uani 1 1 d . . . C34 C 0.4396(5) 1.2536(3) 0.0778(3) 0.0966(18) Uani 1 1 d . . . H34A H 0.4740 1.2961 0.0587 0.145 Uiso 1 1 calc R . . H34B H 0.3860 1.2674 0.1122 0.145 Uiso 1 1 calc R . . H34C H 0.3978 1.2272 0.0445 0.145 Uiso 1 1 calc R . . C35 C 0.7534(3) 1.17802(19) 0.15696(17) 0.0438(9) Uani 1 1 d . . . C36 C 0.7815(5) 1.1846(3) 0.27140(19) 0.0718(14) Uani 1 1 d . . . H36A H 0.8658 1.1877 0.2696 0.108 Uiso 1 1 calc R . . H36B H 0.7582 1.1595 0.3108 0.108 Uiso 1 1 calc R . . H36C H 0.7486 1.2324 0.2717 0.108 Uiso 1 1 calc R . . C37 C 0.4223(3) 1.0379(2) -0.04211(17) 0.0436(9) Uani 1 1 d . . . C38 C 0.2638(5) 1.1141(2) -0.0718(3) 0.0826(15) Uani 1 1 d . . . H38A H 0.2126 1.0910 -0.0406 0.124 Uiso 1 1 calc R . . H38B H 0.2195 1.1276 -0.1102 0.124 Uiso 1 1 calc R . . H38C H 0.2977 1.1564 -0.0521 0.124 Uiso 1 1 calc R . . C39 C 0.4769(3) 0.94868(19) -0.12782(16) 0.0375(8) Uani 1 1 d . . . C40 C 0.4824(4) 0.9380(3) -0.24388(18) 0.0663(13) Uani 1 1 d . . . H40A H 0.4736 0.8867 -0.2394 0.099 Uiso 1 1 calc R . . H40B H 0.5349 0.9484 -0.2798 0.099 Uiso 1 1 calc R . . H40C H 0.4071 0.9595 -0.2525 0.099 Uiso 1 1 calc R . . Cl1 Cl 0.6516(8) 0.4092(3) 0.3401(3) 0.437(5) Uani 1 1 d . . . Cl2 Cl 0.5511(4) 0.35822(19) 0.2280(2) 0.2412(17) Uani 1 1 d . . . C43 C 0.5761(10) 0.3623(6) 0.3245(9) 0.304(12) Uani 1 1 d . . . H43A H 0.5021 0.3735 0.3460 0.364 Uiso 1 1 calc R . . H43B H 0.6019 0.3153 0.3400 0.364 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0385(5) 0.0321(4) 0.0254(4) 0.0030(3) -0.0004(4) -0.0025(4) P2 0.0334(5) 0.0405(5) 0.0279(4) -0.0035(4) 0.0033(3) -0.0071(4) O1 0.0497(15) 0.0572(15) 0.0369(12) 0.0097(11) -0.0002(11) -0.0168(13) O2 0.0515(15) 0.0334(12) 0.0273(10) 0.0021(9) -0.0047(10) 0.0020(11) O3 0.0611(16) 0.0338(13) 0.0329(11) 0.0035(10) 0.0036(11) 0.0055(12) O4 0.0670(18) 0.0450(15) 0.0403(12) -0.0044(11) 0.0152(13) -0.0176(13) O5 0.0342(13) 0.0566(15) 0.0307(12) -0.0053(10) 0.0058(9) -0.0059(12) O6 0.0325(14) 0.0666(18) 0.0377(12) -0.0025(11) 0.0013(10) 0.0022(12) O7 0.123(3) 0.0411(16) 0.0597(16) -0.0033(13) 0.0049(18) -0.0297(19) O8 0.0647(18) 0.0564(16) 0.0360(13) -0.0024(11) 0.0017(12) -0.0207(14) O9 0.101(3) 0.089(2) 0.0532(17) 0.0218(16) 0.0009(17) 0.042(2) O10 0.081(2) 0.0640(19) 0.0668(17) 0.0072(15) 0.0125(16) 0.0335(17) O11 0.074(2) 0.119(3) 0.0531(17) -0.0138(17) -0.0026(15) 0.043(2) O12 0.0613(18) 0.0740(19) 0.0482(15) 0.0112(13) -0.0050(13) 0.0257(16) O13 0.0536(17) 0.0760(19) 0.0461(13) 0.0099(13) -0.0129(13) -0.0295(16) O14 0.0496(15) 0.0649(17) 0.0321(12) -0.0042(12) 0.0020(11) -0.0165(14) C1 0.068(3) 0.048(2) 0.0254(15) 0.0069(15) -0.0014(17) 0.002(2) C2 0.069(3) 0.038(2) 0.0363(18) 0.0088(15) -0.0086(18) 0.005(2) C3 0.086(3) 0.0290(19) 0.0393(19) 0.0042(15) -0.0055(19) 0.007(2) C4 0.074(3) 0.060(3) 0.063(3) -0.001(2) -0.022(2) 0.014(2) C5 0.134(5) 0.055(3) 0.045(2) 0.021(2) -0.008(3) 0.013(3) C6 0.0336(17) 0.0353(17) 0.0202(14) -0.0009(13) -0.0008(12) -0.0022(15) C7 0.0352(18) 0.0272(16) 0.0229(13) -0.0006(12) -0.0003(12) 0.0024(15) C8 0.042(2) 0.0337(18) 0.0299(16) 0.0016(13) 0.0081(14) -0.0032(16) C9 0.052(2) 0.0333(18) 0.0290(15) 0.0001(13) 0.0013(15) 0.0014(17) C10 0.043(2) 0.0314(18) 0.0300(15) 0.0012(13) 0.0054(14) -0.0080(17) C11 0.0423(19) 0.0405(19) 0.0244(14) -0.0041(14) 0.0044(14) -0.0096(17) C12 0.064(3) 0.046(2) 0.0335(18) -0.0062(15) 0.0042(18) -0.022(2) C13 0.053(3) 0.068(3) 0.046(2) -0.0132(19) -0.0008(18) -0.030(2) C14 0.038(2) 0.089(3) 0.0428(19) -0.002(2) 0.0004(16) -0.017(2) C15 0.038(2) 0.056(2) 0.0332(17) -0.0022(15) -0.0012(14) -0.0072(18) C16 0.0354(18) 0.0400(19) 0.0209(13) 0.0004(13) -0.0005(13) -0.0080(15) C17 0.050(2) 0.067(3) 0.0311(17) -0.0079(17) 0.0107(16) -0.014(2) C18 0.043(2) 0.078(3) 0.052(2) -0.017(2) 0.0159(18) -0.004(2) C19 0.031(2) 0.092(3) 0.058(2) -0.019(2) 0.0093(17) -0.006(2) C20 0.055(3) 0.139(5) 0.073(3) -0.035(3) 0.029(2) -0.008(3) C21 0.069(3) 0.072(3) 0.080(3) -0.021(2) 0.009(2) 0.009(3) C22 0.0357(19) 0.0333(17) 0.0207(14) 0.0000(12) -0.0041(13) -0.0060(16) C23 0.0322(18) 0.0298(16) 0.0245(14) 0.0035(12) -0.0008(12) -0.0035(15) C24 0.0391(19) 0.0383(18) 0.0316(15) 0.0068(14) -0.0033(14) -0.0026(16) C25 0.0325(18) 0.042(2) 0.0312(15) 0.0036(15) -0.0023(14) -0.0007(16) C26 0.0293(18) 0.0400(19) 0.0295(16) 0.0067(14) 0.0008(13) -0.0023(16) C27 0.0346(19) 0.0350(19) 0.0244(15) 0.0016(13) -0.0007(13) -0.0075(15) C28 0.041(2) 0.044(2) 0.050(2) -0.0019(17) -0.0051(16) -0.0113(19) C29 0.063(3) 0.038(2) 0.068(3) -0.0059(18) -0.004(2) -0.017(2) C30 0.060(3) 0.034(2) 0.063(2) -0.0029(17) -0.007(2) 0.003(2) C31 0.043(2) 0.038(2) 0.0424(18) -0.0048(15) 0.0017(16) 0.0029(18) C32 0.039(2) 0.0319(18) 0.0243(14) 0.0019(13) -0.0008(13) -0.0033(15) C33 0.065(3) 0.034(2) 0.053(2) -0.0002(17) 0.002(2) 0.0015(19) C34 0.098(4) 0.092(4) 0.100(4) 0.004(3) 0.002(3) 0.050(4) C35 0.056(2) 0.034(2) 0.0409(19) -0.0054(16) 0.0078(16) -0.0031(19) C36 0.081(3) 0.091(3) 0.044(2) -0.015(2) -0.003(2) -0.035(3) C37 0.036(2) 0.054(2) 0.0413(19) 0.0037(17) 0.0008(15) -0.0031(19) C38 0.085(4) 0.071(3) 0.092(3) 0.009(3) -0.009(3) 0.040(3) C39 0.0307(19) 0.042(2) 0.0394(18) 0.0058(15) -0.0017(15) 0.0006(17) C40 0.066(3) 0.093(3) 0.040(2) -0.010(2) -0.0014(19) -0.021(3) Cl1 0.612(13) 0.320(6) 0.378(7) 0.090(5) -0.237(8) -0.188(8) Cl2 0.269(4) 0.188(3) 0.267(4) -0.012(3) 0.078(3) 0.009(3) C43 0.133(9) 0.176(11) 0.60(4) -0.206(17) -0.047(14) -0.022(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.464(3) . ? P1 O3 1.581(2) . ? P1 O2 1.594(2) . ? P1 C6 1.812(3) . ? P2 O4 1.459(3) . ? P2 O6 1.581(3) . ? P2 O5 1.586(2) . ? P2 C22 1.820(3) . ? O2 C1 1.468(4) . ? O3 C3 1.468(4) . ? O5 C17 1.464(4) . ? O6 C19 1.476(4) . ? O7 C35 1.197(4) . ? O8 C35 1.306(4) . ? O8 C36 1.468(4) . ? O9 C33 1.197(4) . ? O10 C33 1.332(5) . ? O10 C34 1.442(5) . ? O11 C37 1.197(4) . ? O12 C37 1.322(4) . ? O12 C38 1.464(5) . ? O13 C39 1.194(4) . ? O14 C39 1.323(4) . ? O14 C40 1.458(4) . ? C1 C2 1.531(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.522(6) . ? C2 C5 1.531(5) . ? C2 C3 1.536(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C16 1.512(4) . ? C6 C7 1.559(4) . ? C6 C22 1.625(4) . ? C7 C23 1.530(4) . ? C7 C8 1.553(4) . ? C7 C10 1.557(4) . ? C8 C9 1.554(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C35 1.520(5) . ? C9 C33 1.524(5) . ? C9 C10 1.573(5) . ? C10 C11 1.507(5) . ? C10 H10 0.9800 . ? C11 C16 1.394(5) . ? C11 C12 1.398(5) . ? C12 C13 1.367(6) . ? C12 H12 0.9300 . ? C13 C14 1.394(6) . ? C13 H13 0.9300 . ? C14 C15 1.385(5) . ? C14 H14 0.9300 . ? C15 C16 1.382(5) . ? C15 H15 0.9300 . ? C17 C18 1.529(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C21 1.503(6) . ? C18 C19 1.514(5) . ? C18 C20 1.547(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C32 1.531(4) . ? C22 C23 1.553(5) . ? C23 C24 1.556(4) . ? C23 C26 1.559(4) . ? C24 C25 1.565(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C37 1.515(5) . ? C25 C39 1.518(5) . ? C25 C26 1.578(4) . ? C26 C27 1.501(5) . ? C26 H26 0.9800 . ? C27 C28 1.390(5) . ? C27 C32 1.407(5) . ? C28 C29 1.375(5) . ? C28 H28 0.9300 . ? C29 C30 1.378(6) . ? C29 H29 0.9300 . ? C30 C31 1.386(5) . ? C30 H30 0.9300 . ? C31 C32 1.375(5) . ? C31 H31 0.9300 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? Cl1 C43 1.260(9) . ? Cl2 C43 1.976(17) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O3 114.34(15) . . ? O1 P1 O2 113.20(14) . . ? O3 P1 O2 103.11(12) . . ? O1 P1 C6 114.96(14) . . ? O3 P1 C6 106.30(13) . . ? O2 P1 C6 103.69(13) . . ? O4 P2 O6 115.53(16) . . ? O4 P2 O5 113.13(14) . . ? O6 P2 O5 103.17(13) . . ? O4 P2 C22 114.64(14) . . ? O6 P2 C22 105.12(13) . . ? O5 P2 C22 103.91(13) . . ? C1 O2 P1 112.53(19) . . ? C3 O3 P1 113.6(2) . . ? C17 O5 P2 113.2(2) . . ? C19 O6 P2 115.4(2) . . ? C35 O8 C36 115.3(3) . . ? C33 O10 C34 116.5(3) . . ? C37 O12 C38 116.1(3) . . ? C39 O14 C40 116.1(3) . . ? O2 C1 C2 111.6(3) . . ? O2 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O2 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C4 C2 C1 110.3(3) . . ? C4 C2 C5 110.8(4) . . ? C1 C2 C5 107.8(3) . . ? C4 C2 C3 110.6(3) . . ? C1 C2 C3 109.6(3) . . ? C5 C2 C3 107.7(3) . . ? O3 C3 C2 111.1(3) . . ? O3 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? O3 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C16 C6 C7 105.0(2) . . ? C16 C6 C22 120.0(2) . . ? C7 C6 C22 87.4(2) . . ? C16 C6 P1 115.2(2) . . ? C7 C6 P1 112.5(2) . . ? C22 C6 P1 112.7(2) . . ? C23 C7 C8 125.0(3) . . ? C23 C7 C10 120.3(2) . . ? C8 C7 C10 89.8(2) . . ? C23 C7 C6 91.3(2) . . ? C8 C7 C6 125.4(2) . . ? C10 C7 C6 106.4(2) . . ? C7 C8 C9 90.5(2) . . ? C7 C8 H8A 113.6 . . ? C9 C8 H8A 113.6 . . ? C7 C8 H8B 113.6 . . ? C9 C8 H8B 113.6 . . ? H8A C8 H8B 110.8 . . ? C35 C9 C33 107.9(3) . . ? C35 C9 C8 120.8(3) . . ? C33 C9 C8 111.2(3) . . ? C35 C9 C10 115.1(3) . . ? C33 C9 C10 111.6(3) . . ? C8 C9 C10 89.2(2) . . ? C11 C10 C7 104.3(3) . . ? C11 C10 C9 120.3(3) . . ? C7 C10 C9 89.7(2) . . ? C11 C10 H10 113.2 . . ? C7 C10 H10 113.2 . . ? C9 C10 H10 113.2 . . ? C16 C11 C12 120.2(3) . . ? C16 C11 C10 111.9(3) . . ? C12 C11 C10 127.4(3) . . ? C13 C12 C11 119.0(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 120.9(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 120.4(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.0(4) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 C6 128.8(3) . . ? C11 C16 C6 110.7(3) . . ? O5 C17 C18 111.8(3) . . ? O5 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? O5 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C21 C18 C19 111.0(4) . . ? C21 C18 C17 110.7(4) . . ? C19 C18 C17 109.9(3) . . ? C21 C18 C20 109.5(4) . . ? C19 C18 C20 108.0(3) . . ? C17 C18 C20 107.7(4) . . ? O6 C19 C18 111.7(3) . . ? O6 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? O6 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C32 C22 C23 105.0(3) . . ? C32 C22 C6 119.4(2) . . ? C23 C22 C6 88.0(2) . . ? C32 C22 P2 114.1(2) . . ? C23 C22 P2 114.6(2) . . ? C6 C22 P2 112.7(2) . . ? C7 C23 C22 91.0(2) . . ? C7 C23 C24 125.4(3) . . ? C22 C23 C24 123.4(2) . . ? C7 C23 C26 121.5(2) . . ? C22 C23 C26 107.0(2) . . ? C24 C23 C26 90.0(2) . . ? C23 C24 C25 90.4(2) . . ? C23 C24 H24A 113.6 . . ? C25 C24 H24A 113.6 . . ? C23 C24 H24B 113.6 . . ? C25 C24 H24B 113.6 . . ? H24A C24 H24B 110.8 . . ? C37 C25 C39 109.4(3) . . ? C37 C25 C24 109.8(3) . . ? C39 C25 C24 119.6(3) . . ? C37 C25 C26 111.7(3) . . ? C39 C25 C26 115.9(3) . . ? C24 C25 C26 89.0(2) . . ? C27 C26 C23 104.4(3) . . ? C27 C26 C25 119.1(3) . . ? C23 C26 C25 89.8(2) . . ? C27 C26 H26 113.5 . . ? C23 C26 H26 113.5 . . ? C25 C26 H26 113.5 . . ? C28 C27 C32 118.6(3) . . ? C28 C27 C26 128.8(3) . . ? C32 C27 C26 112.2(3) . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 121.4(4) . . ? C28 C29 H29 119.3 . . ? C30 C29 H29 119.3 . . ? C29 C30 C31 119.8(4) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C32 C31 C30 119.3(3) . . ? C32 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C31 C32 C27 121.2(3) . . ? C31 C32 C22 128.9(3) . . ? C27 C32 C22 109.9(3) . . ? O9 C33 O10 124.1(4) . . ? O9 C33 C9 125.6(4) . . ? O10 C33 C9 110.3(3) . . ? O10 C34 H34A 109.5 . . ? O10 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O10 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O7 C35 O8 123.8(3) . . ? O7 C35 C9 122.6(3) . . ? O8 C35 C9 113.6(3) . . ? O8 C36 H36A 109.5 . . ? O8 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O8 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O11 C37 O12 123.6(4) . . ? O11 C37 C25 125.1(3) . . ? O12 C37 C25 111.3(3) . . ? O12 C38 H38A 109.5 . . ? O12 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O12 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O13 C39 O14 124.0(3) . . ? O13 C39 C25 123.1(3) . . ? O14 C39 C25 113.0(3) . . ? O14 C40 H40A 109.5 . . ? O14 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O14 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? Cl1 C43 Cl2 111.9(12) . . ? Cl1 C43 H43A 109.2 . . ? Cl2 C43 H43A 109.2 . . ? Cl1 C43 H43B 109.2 . . ? Cl2 C43 H43B 109.2 . . ? H43A C43 H43B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.048 #===END data_compound-24 _database_code_depnum_ccdc_archive 'CCDC 804476' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H43 O7 P' _chemical_formula_weight 642.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1399(11) _cell_length_b 11.3816(10) _cell_length_c 24.2961(17) _cell_angle_alpha 90.00 _cell_angle_beta 114.555(4) _cell_angle_gamma 90.00 _cell_volume 3304.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5767 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9764 _exptl_absorpt_process_details 'SADABS, Sheldrick(1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 30995 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5831 _reflns_number_gt 4990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+6.6323P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5831 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2002 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.25994(7) 0.82304(8) 0.67966(4) 0.0266(3) Uani 1 1 d . . . O1 O 0.3092(2) 0.7205(2) 0.66477(11) 0.0334(6) Uani 1 1 d . . . O2 O 0.16280(19) 0.7954(2) 0.70057(10) 0.0273(6) Uani 1 1 d . . . O3 O 0.21134(19) 0.9186(2) 0.62725(11) 0.0280(6) Uani 1 1 d . . . O4 O 0.7745(3) 0.8408(3) 0.89544(18) 0.0718(11) Uani 1 1 d . . . O5 O 0.7237(2) 1.0143(3) 0.91471(14) 0.0515(8) Uani 1 1 d . . . O6 O 0.4414(3) 0.7784(3) 0.87137(15) 0.0609(9) Uani 1 1 d . . . O7 O 0.5710(3) 0.8764(3) 0.94706(14) 0.0575(9) Uani 1 1 d . . . C1 C 0.0792(3) 0.7084(3) 0.67450(15) 0.0247(7) Uani 1 1 d . . . C2 C 0.0827(3) 0.6044(3) 0.70560(16) 0.0275(8) Uani 1 1 d . . . C3 C -0.0035(3) 0.5256(3) 0.67568(17) 0.0337(9) Uani 1 1 d . . . H3 H -0.0029 0.4541 0.6944 0.040 Uiso 1 1 calc R . . C4 C -0.0910(3) 0.5472(3) 0.61928(17) 0.0328(9) Uani 1 1 d . . . C5 C -0.0926(3) 0.6540(3) 0.59287(16) 0.0304(8) Uani 1 1 d . . . H5 H -0.1518 0.6719 0.5562 0.036 Uiso 1 1 calc R . . C6 C -0.0080(3) 0.7362(3) 0.61959(16) 0.0264(8) Uani 1 1 d . . . C7 C -0.0141(3) 0.8538(3) 0.58964(16) 0.0289(8) Uani 1 1 d . . . H7A H 0.0208 0.9125 0.6208 0.035 Uiso 1 1 calc R . . H7B H -0.0921 0.8753 0.5677 0.035 Uiso 1 1 calc R . . C8 C 0.0419(3) 0.8563(3) 0.54630(16) 0.0265(8) Uani 1 1 d . . . C9 C -0.0175(3) 0.8270(3) 0.48658(16) 0.0297(8) Uani 1 1 d . . . H9 H -0.0912 0.8020 0.4734 0.036 Uiso 1 1 calc R . . C10 C 0.0302(3) 0.8338(3) 0.44588(16) 0.0317(8) Uani 1 1 d . . . C11 C 0.1389(3) 0.8758(3) 0.46614(16) 0.0306(8) Uani 1 1 d . . . H11 H 0.1702 0.8828 0.4383 0.037 Uiso 1 1 calc R . . C12 C 0.2031(3) 0.9078(3) 0.52537(16) 0.0275(8) Uani 1 1 d . . . C13 C 0.1529(3) 0.8918(3) 0.56553(15) 0.0257(8) Uani 1 1 d . . . C14 C 0.1714(3) 0.5781(4) 0.76997(17) 0.0368(9) Uani 1 1 d . . . C15 C 0.1337(4) 0.4782(4) 0.79880(18) 0.0416(10) Uani 1 1 d . . . H15A H 0.1261 0.4076 0.7758 0.062 Uiso 1 1 calc R . . H15B H 0.0630 0.4978 0.7992 0.062 Uiso 1 1 calc R . . H15C H 0.1883 0.4663 0.8395 0.062 Uiso 1 1 calc R . . C16 C 0.1853(4) 0.6872(4) 0.81107(19) 0.0536(12) Uani 1 1 d . . . H16A H 0.2326 0.6673 0.8522 0.080 Uiso 1 1 calc R . . H16B H 0.1132 0.7112 0.8083 0.080 Uiso 1 1 calc R . . H16C H 0.2185 0.7503 0.7981 0.080 Uiso 1 1 calc R . . C17 C 0.2826(4) 0.5480(6) 0.7684(2) 0.0667(16) Uani 1 1 d . . . H17A H 0.2750 0.4770 0.7457 0.100 Uiso 1 1 calc R . . H17B H 0.3382 0.5370 0.8089 0.100 Uiso 1 1 calc R . . H17C H 0.3050 0.6110 0.7495 0.100 Uiso 1 1 calc R . . C18 C -0.1851(4) 0.4598(4) 0.5916(2) 0.0456(11) Uani 1 1 d . . . H18A H -0.2363 0.4872 0.5525 0.068 Uiso 1 1 calc R . . H18B H -0.2238 0.4513 0.6173 0.068 Uiso 1 1 calc R . . H18C H -0.1550 0.3851 0.5874 0.068 Uiso 1 1 calc R . . C19 C -0.0356(4) 0.7994(4) 0.38072(17) 0.0464(11) Uani 1 1 d . . . H19A H -0.0367 0.7154 0.3772 0.070 Uiso 1 1 calc R . . H19B H -0.0012 0.8328 0.3564 0.070 Uiso 1 1 calc R . . H19C H -0.1108 0.8282 0.3671 0.070 Uiso 1 1 calc R . . C20 C 0.3213(3) 0.9599(4) 0.54351(18) 0.0347(9) Uani 1 1 d . . . C21 C 0.3410(4) 0.9979(5) 0.4889(2) 0.0593(14) Uani 1 1 d . . . H21A H 0.4111 1.0386 0.5022 0.089 Uiso 1 1 calc R . . H21B H 0.2816 1.0492 0.4642 0.089 Uiso 1 1 calc R . . H21C H 0.3426 0.9300 0.4659 0.089 Uiso 1 1 calc R . . C22 C 0.3376(4) 1.0722(5) 0.5811(3) 0.0613(14) Uani 1 1 d . . . H22A H 0.3269 1.0549 0.6170 0.092 Uiso 1 1 calc R . . H22B H 0.2841 1.1302 0.5576 0.092 Uiso 1 1 calc R . . H22C H 0.4119 1.1018 0.5922 0.092 Uiso 1 1 calc R . . C23 C 0.4086(4) 0.8704(5) 0.5788(2) 0.0549(12) Uani 1 1 d . . . H23A H 0.3974 0.8000 0.5552 0.082 Uiso 1 1 calc R . . H23B H 0.4023 0.8527 0.6159 0.082 Uiso 1 1 calc R . . H23C H 0.4817 0.9015 0.5877 0.082 Uiso 1 1 calc R . . C24 C 0.3501(3) 0.9147(3) 0.73816(16) 0.0299(8) Uani 1 1 d . . . C25 C 0.3176(3) 1.0141(3) 0.76663(15) 0.0276(8) Uani 1 1 d . . . C26 C 0.2153(3) 1.0628(3) 0.75531(17) 0.0323(8) Uani 1 1 d . . . H26 H 0.1509 1.0343 0.7240 0.039 Uiso 1 1 calc R . . C27 C 0.2091(3) 1.1541(3) 0.79076(18) 0.0389(10) Uani 1 1 d . . . H27 H 0.1400 1.1874 0.7832 0.047 Uiso 1 1 calc R . . C28 C 0.3039(4) 1.1971(4) 0.83734(19) 0.0437(10) Uani 1 1 d . . . H28 H 0.2980 1.2588 0.8609 0.052 Uiso 1 1 calc R . . C29 C 0.4071(3) 1.1496(3) 0.84929(18) 0.0389(10) Uani 1 1 d . . . H29 H 0.4711 1.1801 0.8801 0.047 Uiso 1 1 calc R . . C30 C 0.4146(3) 1.0564(3) 0.81508(16) 0.0311(8) Uani 1 1 d . . . C31 C 0.5130(3) 0.9940(3) 0.81364(16) 0.0335(9) Uani 1 1 d . . . H31 H 0.5624 1.0479 0.8048 0.040 Uiso 1 1 calc R . . C32 C 0.5807(3) 0.8853(4) 0.85368(17) 0.0358(9) Uani 1 1 d . . . C33 C 0.5525(3) 0.8152(4) 0.79338(17) 0.0364(9) Uani 1 1 d . . . H33A H 0.6111 0.8165 0.7789 0.044 Uiso 1 1 calc R . . H33B H 0.5249 0.7362 0.7934 0.044 Uiso 1 1 calc R . . C34 C 0.4626(3) 0.9056(4) 0.76491(16) 0.0336(9) Uani 1 1 d . . . C35 C 0.7049(3) 0.9100(4) 0.89077(18) 0.0410(10) Uani 1 1 d . . . C36 C 0.8413(4) 1.0462(5) 0.9454(2) 0.0604(15) Uani 1 1 d . . . H36A H 0.8776 0.9955 0.9796 0.091 Uiso 1 1 calc R . . H36B H 0.8475 1.1262 0.9589 0.091 Uiso 1 1 calc R . . H36C H 0.8763 1.0380 0.9179 0.091 Uiso 1 1 calc R . . C37 C 0.5219(3) 0.8387(4) 0.89042(18) 0.0380(9) Uani 1 1 d . . . C38 C 0.5173(5) 0.8392(5) 0.9850(2) 0.0696(16) Uani 1 1 d . . . H38A H 0.4399 0.8619 0.9668 0.104 Uiso 1 1 calc R . . H38B H 0.5534 0.8757 1.0241 0.104 Uiso 1 1 calc R . . H38C H 0.5227 0.7554 0.9896 0.104 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0211(5) 0.0282(5) 0.0254(5) -0.0043(4) 0.0044(4) 0.0000(4) O1 0.0287(13) 0.0340(15) 0.0342(14) -0.0025(12) 0.0097(11) 0.0034(11) O2 0.0265(13) 0.0262(13) 0.0253(12) -0.0044(10) 0.0070(10) 0.0000(10) O3 0.0216(12) 0.0292(13) 0.0286(13) -0.0069(11) 0.0058(10) -0.0034(10) O4 0.0372(18) 0.074(3) 0.081(3) -0.008(2) 0.0017(17) 0.0095(18) O5 0.0325(16) 0.0499(19) 0.0538(19) 0.0131(16) -0.0004(14) -0.0086(14) O6 0.0406(18) 0.079(2) 0.056(2) 0.0075(18) 0.0133(16) -0.0157(18) O7 0.078(2) 0.053(2) 0.0494(19) -0.0043(16) 0.0337(18) -0.0169(17) C1 0.0226(17) 0.0284(19) 0.0247(18) -0.0059(14) 0.0115(15) -0.0007(14) C2 0.0289(18) 0.030(2) 0.0268(18) 0.0007(15) 0.0146(16) 0.0045(15) C3 0.041(2) 0.030(2) 0.034(2) 0.0052(16) 0.0205(18) -0.0001(17) C4 0.032(2) 0.034(2) 0.031(2) -0.0047(16) 0.0118(17) -0.0067(16) C5 0.0234(18) 0.037(2) 0.0263(19) -0.0009(16) 0.0061(15) -0.0011(15) C6 0.0229(17) 0.0292(19) 0.0282(19) 0.0005(15) 0.0119(15) 0.0034(15) C7 0.0217(17) 0.0294(19) 0.0296(19) 0.0003(15) 0.0046(15) 0.0030(15) C8 0.0238(17) 0.0189(17) 0.0326(19) 0.0057(14) 0.0076(15) 0.0040(14) C9 0.0250(18) 0.0248(19) 0.0288(19) 0.0057(15) 0.0006(15) -0.0014(15) C10 0.034(2) 0.0265(19) 0.0271(19) 0.0066(15) 0.0058(16) -0.0005(16) C11 0.032(2) 0.030(2) 0.0300(19) 0.0056(16) 0.0126(16) 0.0029(16) C12 0.0244(18) 0.0236(18) 0.0324(19) 0.0040(15) 0.0096(15) 0.0048(14) C13 0.0233(17) 0.0207(17) 0.0260(18) -0.0013(14) 0.0032(15) 0.0021(14) C14 0.031(2) 0.052(3) 0.030(2) 0.0101(18) 0.0141(17) 0.0037(18) C15 0.051(3) 0.038(2) 0.033(2) 0.0075(18) 0.0150(19) 0.0045(19) C16 0.063(3) 0.063(3) 0.030(2) 0.003(2) 0.014(2) -0.016(2) C17 0.048(3) 0.100(4) 0.055(3) 0.038(3) 0.025(2) 0.032(3) C18 0.048(3) 0.039(2) 0.045(2) 0.0011(19) 0.015(2) -0.014(2) C19 0.048(3) 0.056(3) 0.027(2) 0.0054(19) 0.0069(19) -0.010(2) C20 0.0252(19) 0.041(2) 0.037(2) 0.0010(18) 0.0128(17) -0.0022(17) C21 0.037(2) 0.075(4) 0.064(3) 0.016(3) 0.018(2) -0.006(2) C22 0.048(3) 0.056(3) 0.089(4) -0.017(3) 0.037(3) -0.020(2) C23 0.035(2) 0.072(3) 0.057(3) 0.005(3) 0.018(2) 0.008(2) C24 0.0243(18) 0.032(2) 0.0267(19) -0.0022(15) 0.0041(15) -0.0007(15) C25 0.0273(18) 0.0253(18) 0.0239(17) 0.0004(14) 0.0042(15) -0.0019(15) C26 0.0262(19) 0.030(2) 0.032(2) 0.0016(16) 0.0025(16) -0.0006(15) C27 0.037(2) 0.031(2) 0.042(2) 0.0011(18) 0.0093(19) 0.0071(17) C28 0.052(3) 0.030(2) 0.043(2) -0.0081(18) 0.013(2) 0.0049(19) C29 0.041(2) 0.030(2) 0.032(2) -0.0080(17) 0.0013(18) -0.0044(17) C30 0.0278(19) 0.031(2) 0.0272(19) 0.0037(16) 0.0039(15) -0.0016(15) C31 0.0255(19) 0.037(2) 0.0289(19) 0.0051(16) 0.0017(16) -0.0026(16) C32 0.0283(19) 0.040(2) 0.031(2) 0.0038(17) 0.0048(16) 0.0015(17) C33 0.0243(18) 0.040(2) 0.038(2) 0.0006(18) 0.0057(16) 0.0034(17) C34 0.0272(19) 0.042(2) 0.0274(19) 0.0002(17) 0.0066(16) -0.0011(17) C35 0.030(2) 0.048(3) 0.034(2) 0.0035(19) 0.0020(18) 0.017(2) C36 0.032(2) 0.078(4) 0.046(3) 0.024(2) -0.009(2) -0.019(2) C37 0.031(2) 0.038(2) 0.037(2) 0.0061(18) 0.0056(18) 0.0061(18) C38 0.102(4) 0.066(4) 0.058(3) 0.001(3) 0.050(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.452(3) . ? P1 O2 1.589(3) . ? P1 O3 1.592(3) . ? P1 C24 1.764(4) . ? O2 C1 1.418(4) . ? O3 C13 1.405(4) . ? O4 C35 1.175(5) . ? O5 C35 1.300(5) . ? O5 C36 1.454(5) . ? O6 C37 1.183(5) . ? O7 C37 1.325(5) . ? O7 C38 1.439(6) . ? C1 C6 1.386(5) . ? C1 C2 1.395(5) . ? C2 C3 1.390(5) . ? C2 C14 1.542(5) . ? C3 C4 1.397(5) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 C18 1.510(5) . ? C5 C6 1.391(5) . ? C5 H5 0.9300 . ? C6 C7 1.510(5) . ? C7 C8 1.514(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.373(5) . ? C8 C13 1.393(5) . ? C9 C10 1.376(5) . ? C9 H9 0.9300 . ? C10 C11 1.388(5) . ? C10 C19 1.506(5) . ? C11 C12 1.381(5) . ? C11 H11 0.9300 . ? C12 C13 1.398(5) . ? C12 C20 1.546(5) . ? C14 C17 1.516(6) . ? C14 C15 1.522(6) . ? C14 C16 1.555(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C23 1.507(6) . ? C20 C21 1.516(6) . ? C20 C22 1.534(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C34 1.349(5) . ? C24 C25 1.479(5) . ? C25 C26 1.372(5) . ? C25 C30 1.412(5) . ? C26 C27 1.373(5) . ? C26 H26 0.9300 . ? C27 C28 1.378(6) . ? C27 H27 0.9300 . ? C28 C29 1.374(6) . ? C28 H28 0.9300 . ? C29 C30 1.376(5) . ? C29 H29 0.9300 . ? C30 C31 1.489(5) . ? C31 C34 1.483(5) . ? C31 C32 1.596(5) . ? C31 H31 0.9800 . ? C32 C37 1.499(6) . ? C32 C35 1.527(5) . ? C32 C33 1.572(6) . ? C33 C34 1.501(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 114.88(15) . . ? O1 P1 O3 114.97(14) . . ? O2 P1 O3 106.40(13) . . ? O1 P1 C24 117.17(16) . . ? O2 P1 C24 102.65(15) . . ? O3 P1 C24 98.78(15) . . ? C1 O2 P1 124.9(2) . . ? C13 O3 P1 124.4(2) . . ? C35 O5 C36 114.9(4) . . ? C37 O7 C38 114.5(4) . . ? C6 C1 C2 122.9(3) . . ? C6 C1 O2 116.6(3) . . ? C2 C1 O2 120.4(3) . . ? C3 C2 C1 115.3(3) . . ? C3 C2 C14 120.9(3) . . ? C1 C2 C14 123.7(3) . . ? C2 C3 C4 124.0(4) . . ? C2 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? C5 C4 C3 117.5(3) . . ? C5 C4 C18 121.7(3) . . ? C3 C4 C18 120.6(4) . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 118.4(3) . . ? C1 C6 C7 121.6(3) . . ? C5 C6 C7 120.0(3) . . ? C6 C7 C8 114.1(3) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 118.7(3) . . ? C9 C8 C7 120.2(3) . . ? C13 C8 C7 121.0(3) . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C11 118.3(3) . . ? C9 C10 C19 120.4(3) . . ? C11 C10 C19 121.3(4) . . ? C12 C11 C10 123.6(3) . . ? C12 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? C11 C12 C13 115.6(3) . . ? C11 C12 C20 120.3(3) . . ? C13 C12 C20 124.1(3) . . ? C8 C13 C12 122.3(3) . . ? C8 C13 O3 116.9(3) . . ? C12 C13 O3 120.6(3) . . ? C17 C14 C15 110.1(4) . . ? C17 C14 C2 110.4(3) . . ? C15 C14 C2 111.0(3) . . ? C17 C14 C16 109.9(4) . . ? C15 C14 C16 105.9(3) . . ? C2 C14 C16 109.5(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C23 C20 C21 108.9(4) . . ? C23 C20 C22 109.9(4) . . ? C21 C20 C22 104.5(4) . . ? C23 C20 C12 109.9(3) . . ? C21 C20 C12 112.1(3) . . ? C22 C20 C12 111.4(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C34 C24 C25 107.7(3) . . ? C34 C24 P1 125.3(3) . . ? C25 C24 P1 127.0(3) . . ? C26 C25 C30 119.9(3) . . ? C26 C25 C24 131.6(3) . . ? C30 C25 C24 108.4(3) . . ? C25 C26 C27 119.2(3) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C26 C27 C28 121.0(4) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 120.6(4) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 119.2(4) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C25 120.0(4) . . ? C29 C30 C31 131.5(3) . . ? C25 C30 C31 108.0(3) . . ? C34 C31 C30 103.8(3) . . ? C34 C31 C32 85.0(3) . . ? C30 C31 C32 128.7(3) . . ? C34 C31 H31 111.5 . . ? C30 C31 H31 111.5 . . ? C32 C31 H31 111.5 . . ? C37 C32 C35 113.7(3) . . ? C37 C32 C33 113.3(3) . . ? C35 C32 C33 115.1(3) . . ? C37 C32 C31 110.0(3) . . ? C35 C32 C31 113.9(3) . . ? C33 C32 C31 88.2(3) . . ? C34 C33 C32 85.2(3) . . ? C34 C33 H33A 114.4 . . ? C32 C33 H33A 114.4 . . ? C34 C33 H33B 114.4 . . ? C32 C33 H33B 114.4 . . ? H33A C33 H33B 111.6 . . ? C24 C34 C31 111.7(3) . . ? C24 C34 C33 140.3(4) . . ? C31 C34 C33 95.3(3) . . ? O4 C35 O5 125.0(4) . . ? O4 C35 C32 122.1(4) . . ? O5 C35 C32 112.9(3) . . ? O5 C36 H36A 109.5 . . ? O5 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O5 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O6 C37 O7 124.4(4) . . ? O6 C37 C32 124.8(4) . . ? O7 C37 C32 110.8(3) . . ? O7 C38 H38A 109.5 . . ? O7 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O7 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.772 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.071 #===END data_compound-30 _database_code_depnum_ccdc_archive 'CCDC 804477' #TrackingRef '- kckCIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H47 O7 P, 2(C2 H3 N)' _chemical_formula_sum 'C48 H53 N2 O7 P' _chemical_formula_weight 800.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7058(15) _cell_length_b 14.241(2) _cell_length_c 16.630(2) _cell_angle_alpha 69.432(14) _cell_angle_beta 84.421(13) _cell_angle_gamma 76.489(14) _cell_volume 2092.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2014 _cell_measurement_theta_min 2.9185 _cell_measurement_theta_max 29.0189 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _d_diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 14140 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7245 _reflns_number_gt 4389 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _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^)+(0.0273P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7245 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_restrained_S_all 0.854 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.13189(6) 0.38822(5) 0.25263(4) 0.01275(14) Uani 1 1 d . . . O1 O 0.29921(13) 0.36983(11) 0.26348(9) 0.0127(3) Uani 1 1 d . . . O2 O 0.05067(13) 0.45929(11) 0.30529(8) 0.0115(3) Uani 1 1 d . . . O3 O 0.08157(14) 0.29381(11) 0.27100(9) 0.0160(4) Uani 1 1 d . . . O4 O -0.02681(15) 0.89342(12) 0.13674(10) 0.0221(4) Uani 1 1 d . . . O5 O -0.16501(14) 0.78284(12) 0.15089(10) 0.0203(4) Uani 1 1 d . . . O6 O -0.12976(15) 0.89360(12) -0.04328(10) 0.0205(4) Uani 1 1 d . . . O7 O 0.05877(14) 0.79710(11) -0.08813(9) 0.0176(4) Uani 1 1 d . . . C1 C 0.3786(2) 0.29141(17) 0.33247(14) 0.0134(5) Uani 1 1 d . . . C2 C 0.4741(2) 0.20818(17) 0.31775(14) 0.0155(5) Uani 1 1 d . . . C3 C 0.5518(2) 0.13858(17) 0.38917(15) 0.0182(5) Uani 1 1 d . . . H3 H 0.6168 0.0805 0.3824 0.022 Uiso 1 1 calc R . . C4 C 0.5389(2) 0.14987(17) 0.46968(15) 0.0185(5) Uani 1 1 d . . . C5 C 0.4456(2) 0.23499(18) 0.47938(14) 0.0176(5) Uani 1 1 d . . . H5 H 0.4362 0.2441 0.5337 0.021 Uiso 1 1 calc R . . C6 C 0.3650(2) 0.30753(17) 0.41122(14) 0.0137(5) Uani 1 1 d . . . C7 C 0.2700(2) 0.40300(17) 0.42242(14) 0.0143(5) Uani 1 1 d . . . H7A H 0.2660 0.4602 0.3670 0.017 Uiso 1 1 calc R . . H7B H 0.3131 0.4216 0.4647 0.017 Uiso 1 1 calc R . . C8 C 0.1198(2) 0.39201(16) 0.45214(13) 0.0117(5) Uani 1 1 d . . . C9 C 0.0876(2) 0.35530(17) 0.53902(14) 0.0152(5) Uani 1 1 d . . . H9 H 0.1611 0.3347 0.5794 0.018 Uiso 1 1 calc R . . C10 C -0.0495(2) 0.34781(17) 0.56864(14) 0.0142(5) Uani 1 1 d . . . C11 C -0.1545(2) 0.38032(17) 0.50814(14) 0.0143(5) Uani 1 1 d . . . H11 H -0.2486 0.3760 0.5282 0.017 Uiso 1 1 calc R . . C12 C -0.1310(2) 0.41922(17) 0.41899(14) 0.0136(5) Uani 1 1 d . . . C13 C 0.0113(2) 0.42047(16) 0.39384(13) 0.0120(5) Uani 1 1 d . . . C14 C 0.5022(2) 0.19364(17) 0.22951(14) 0.0156(5) Uani 1 1 d . . . C15 C 0.5593(2) 0.28406(18) 0.16579(14) 0.0215(6) Uani 1 1 d . . . H15A H 0.4880 0.3478 0.1579 0.032 Uiso 1 1 calc R . . H15B H 0.5804 0.2732 0.1105 0.032 Uiso 1 1 calc R . . H15C H 0.6460 0.2891 0.1882 0.032 Uiso 1 1 calc R . . C16 C 0.3680(2) 0.18315(19) 0.19435(15) 0.0239(6) Uani 1 1 d . . . H16A H 0.3270 0.1298 0.2380 0.036 Uiso 1 1 calc R . . H16B H 0.3926 0.1642 0.1427 0.036 Uiso 1 1 calc R . . H16C H 0.2990 0.2487 0.1799 0.036 Uiso 1 1 calc R . . C17 C 0.6153(2) 0.09533(18) 0.23479(15) 0.0245(6) Uani 1 1 d . . . H17A H 0.7030 0.0982 0.2576 0.037 Uiso 1 1 calc R . . H17B H 0.6340 0.0903 0.1773 0.037 Uiso 1 1 calc R . . H17C H 0.5807 0.0351 0.2728 0.037 Uiso 1 1 calc R . . C18 C 0.6314(2) 0.07312(19) 0.54261(16) 0.0298(6) Uani 1 1 d . . . H18A H 0.7221 0.0933 0.5398 0.045 Uiso 1 1 calc R . . H18B H 0.6482 0.0048 0.5377 0.045 Uiso 1 1 calc R . . H18C H 0.5836 0.0717 0.5976 0.045 Uiso 1 1 calc R . . C19 C -0.0822(2) 0.30831(18) 0.66349(14) 0.0205(6) Uani 1 1 d . . . H19A H -0.1849 0.3244 0.6731 0.031 Uiso 1 1 calc R . . H19B H -0.0361 0.3410 0.6930 0.031 Uiso 1 1 calc R . . H19C H -0.0469 0.2338 0.6860 0.031 Uiso 1 1 calc R . . C20 C -0.2561(2) 0.45745(18) 0.35703(14) 0.0153(5) Uani 1 1 d . . . C21 C -0.3992(2) 0.47635(19) 0.40379(14) 0.0208(6) Uani 1 1 d . . . H21A H -0.4133 0.4117 0.4472 0.031 Uiso 1 1 calc R . . H21B H -0.4759 0.5028 0.3622 0.031 Uiso 1 1 calc R . . H21C H -0.3996 0.5266 0.4318 0.031 Uiso 1 1 calc R . . C22 C -0.2478(2) 0.56008(18) 0.28647(14) 0.0206(6) Uani 1 1 d . . . H22A H -0.3350 0.5864 0.2532 0.031 Uiso 1 1 calc R . . H22B H -0.1664 0.5499 0.2484 0.031 Uiso 1 1 calc R . . H22C H -0.2368 0.6096 0.3128 0.031 Uiso 1 1 calc R . . C23 C -0.2589(2) 0.37560(19) 0.31703(15) 0.0244(6) Uani 1 1 d . . . H23A H -0.2744 0.3127 0.3624 0.037 Uiso 1 1 calc R . . H23B H -0.1682 0.3608 0.2876 0.037 Uiso 1 1 calc R . . H23C H -0.3358 0.4011 0.2757 0.037 Uiso 1 1 calc R . . C24 C 0.1185(2) 0.47810(16) 0.14413(13) 0.0126(5) Uani 1 1 d . . . H24 H 0.1862 0.4457 0.1073 0.015 Uiso 1 1 calc R . . C25 C -0.0279(2) 0.50545(17) 0.10698(13) 0.0126(5) Uani 1 1 d . . . C26 C -0.0725(2) 0.61204(17) 0.07402(13) 0.0129(5) Uani 1 1 d . . . C27 C 0.0403(2) 0.65739(17) 0.08857(13) 0.0115(5) Uani 1 1 d . . . C28 C 0.0421(2) 0.77052(17) 0.06134(13) 0.0130(5) Uani 1 1 d . . . C29 C 0.1930(2) 0.78716(17) 0.05969(13) 0.0131(5) Uani 1 1 d . . . C30 C 0.2191(2) 0.88462(18) 0.01551(14) 0.0179(5) Uani 1 1 d . . . H30 H 0.1444 0.9381 -0.0146 0.021 Uiso 1 1 calc R . . C31 C 0.3521(2) 0.90492(18) 0.01476(14) 0.0191(6) Uani 1 1 d . . . H31 H 0.3687 0.9715 -0.0163 0.023 Uiso 1 1 calc R . . C32 C 0.4611(2) 0.82712(18) 0.05976(15) 0.0203(6) Uani 1 1 d . . . H32 H 0.5525 0.8403 0.0602 0.024 Uiso 1 1 calc R . . C33 C 0.4355(2) 0.73016(18) 0.10401(14) 0.0175(5) Uani 1 1 d . . . H33 H 0.5103 0.6772 0.1349 0.021 Uiso 1 1 calc R . . C34 C 0.3024(2) 0.70853(17) 0.10427(13) 0.0136(5) Uani 1 1 d . . . C35 C 0.2834(2) 0.60033(17) 0.15138(14) 0.0158(5) Uani 1 1 d . . . H35A H 0.3642 0.5515 0.1371 0.019 Uiso 1 1 calc R . . H35B H 0.2842 0.5864 0.2140 0.019 Uiso 1 1 calc R . . C36 C 0.1484(2) 0.58252(17) 0.12923(13) 0.0116(5) Uani 1 1 d . . . C37 C -0.1107(2) 0.44139(18) 0.10093(13) 0.0165(5) Uani 1 1 d . . . H37 H -0.0792 0.3689 0.1231 0.020 Uiso 1 1 calc R . . C38 C -0.2418(2) 0.48625(18) 0.06142(13) 0.0171(5) Uani 1 1 d . . . H38 H -0.3009 0.4437 0.0571 0.021 Uiso 1 1 calc R . . C39 C -0.2869(2) 0.59173(18) 0.02845(14) 0.0182(5) Uani 1 1 d . . . H39 H -0.3764 0.6205 0.0017 0.022 Uiso 1 1 calc R . . C40 C -0.2035(2) 0.65666(18) 0.03375(13) 0.0159(5) Uani 1 1 d . . . H40 H -0.2347 0.7291 0.0107 0.019 Uiso 1 1 calc R . . C41 C -0.0522(2) 0.82342(18) 0.12066(14) 0.0149(5) Uani 1 1 d . . . C42 C -0.2613(2) 0.83286(19) 0.20364(15) 0.0241(6) Uani 1 1 d . . . H42A H -0.2109 0.8283 0.2536 0.036 Uiso 1 1 calc R . . H42B H -0.3413 0.7988 0.2230 0.036 Uiso 1 1 calc R . . H42C H -0.2964 0.9052 0.1698 0.036 Uiso 1 1 calc R . . C43 C -0.0217(2) 0.82890(17) -0.02881(14) 0.0144(5) Uani 1 1 d . . . C44 C 0.0137(2) 0.85340(18) -0.17633(14) 0.0218(6) Uani 1 1 d . . . H44A H -0.0844 0.8498 -0.1818 0.033 Uiso 1 1 calc R . . H44B H 0.0754 0.8230 -0.2150 0.033 Uiso 1 1 calc R . . H44C H 0.0198 0.9253 -0.1915 0.033 Uiso 1 1 calc R . . N1 N 0.0418(3) 0.0378(2) 0.62294(16) 0.0602(8) Uani 1 1 d . . . C45 C 0.0635(3) 0.1458(2) 0.46222(16) 0.0371(7) Uani 1 1 d . . . H45A H -0.0094 0.2094 0.4483 0.056 Uiso 1 1 calc R . . H45B H 0.0509 0.1061 0.4269 0.056 Uiso 1 1 calc R . . H45C H 0.1575 0.1625 0.4506 0.056 Uiso 1 1 calc R . . C46 C 0.0511(3) 0.0856(2) 0.55257(18) 0.0338(7) Uani 1 1 d . . . N2 N 0.4426(2) 0.75597(19) 0.32481(15) 0.0411(6) Uani 1 1 d . . . C47 C 0.2586(2) 0.9111(2) 0.23127(16) 0.0316(7) Uani 1 1 d . . . H47A H 0.1919 0.9399 0.2691 0.047 Uiso 1 1 calc R . . H47B H 0.2066 0.8883 0.1965 0.047 Uiso 1 1 calc R . . H47C H 0.3077 0.9636 0.1935 0.047 Uiso 1 1 calc R . . C48 C 0.3624(2) 0.8235(2) 0.28331(16) 0.0252(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0137(3) 0.0124(4) 0.0104(3) -0.0033(3) 0.0010(2) -0.0009(3) O1 0.0102(8) 0.0130(9) 0.0123(8) -0.0032(7) -0.0002(6) 0.0007(7) O2 0.0131(8) 0.0107(9) 0.0083(8) -0.0022(7) 0.0026(6) -0.0006(6) O3 0.0175(8) 0.0131(9) 0.0175(9) -0.0040(7) 0.0000(7) -0.0055(7) O4 0.0251(9) 0.0198(11) 0.0258(10) -0.0137(8) 0.0018(7) -0.0047(8) O5 0.0178(9) 0.0177(10) 0.0264(10) -0.0114(8) 0.0077(7) -0.0030(7) O6 0.0190(9) 0.0160(10) 0.0206(9) -0.0036(8) -0.0054(7) 0.0053(7) O7 0.0209(9) 0.0180(10) 0.0117(9) -0.0042(7) -0.0024(7) -0.0007(7) C1 0.0115(12) 0.0127(14) 0.0131(12) -0.0004(10) -0.0010(9) -0.0029(10) C2 0.0123(12) 0.0142(14) 0.0203(13) -0.0046(11) 0.0001(10) -0.0055(10) C3 0.0123(12) 0.0140(14) 0.0272(14) -0.0079(12) -0.0018(10) 0.0015(10) C4 0.0178(13) 0.0128(14) 0.0217(14) -0.0023(11) -0.0036(10) -0.0014(10) C5 0.0150(13) 0.0224(15) 0.0163(13) -0.0068(11) 0.0014(10) -0.0058(11) C6 0.0066(12) 0.0150(14) 0.0209(13) -0.0069(11) 0.0010(9) -0.0046(10) C7 0.0125(13) 0.0155(14) 0.0155(13) -0.0055(11) -0.0009(9) -0.0037(10) C8 0.0120(12) 0.0076(13) 0.0162(13) -0.0064(10) 0.0014(10) -0.0008(9) C9 0.0157(13) 0.0157(14) 0.0157(13) -0.0071(11) -0.0053(10) -0.0015(10) C10 0.0212(13) 0.0094(13) 0.0119(12) -0.0034(10) -0.0001(10) -0.0034(10) C11 0.0127(12) 0.0149(14) 0.0171(13) -0.0080(11) 0.0040(10) -0.0041(10) C12 0.0147(13) 0.0119(13) 0.0170(13) -0.0080(11) 0.0024(10) -0.0045(10) C13 0.0172(13) 0.0094(13) 0.0100(12) -0.0040(10) 0.0047(9) -0.0049(10) C14 0.0141(13) 0.0140(14) 0.0182(13) -0.0061(11) 0.0015(10) -0.0018(10) C15 0.0216(13) 0.0216(15) 0.0190(14) -0.0057(12) 0.0024(10) -0.0032(11) C16 0.0227(14) 0.0275(16) 0.0267(15) -0.0172(13) 0.0004(11) -0.0033(11) C17 0.0248(14) 0.0194(16) 0.0256(15) -0.0085(12) 0.0032(11) 0.0021(11) C18 0.0350(16) 0.0199(16) 0.0283(15) -0.0046(13) -0.0103(12) 0.0044(12) C19 0.0216(13) 0.0236(16) 0.0144(13) -0.0044(11) 0.0024(10) -0.0057(11) C20 0.0116(12) 0.0227(15) 0.0133(12) -0.0075(11) 0.0025(9) -0.0057(10) C21 0.0137(13) 0.0304(16) 0.0187(13) -0.0107(12) 0.0014(10) -0.0021(11) C22 0.0132(13) 0.0259(16) 0.0181(13) -0.0034(12) -0.0031(10) -0.0008(11) C23 0.0232(14) 0.0314(17) 0.0252(15) -0.0158(13) -0.0012(11) -0.0086(12) C24 0.0163(13) 0.0106(13) 0.0085(12) -0.0022(10) 0.0030(9) -0.0012(10) C25 0.0137(13) 0.0141(14) 0.0099(12) -0.0053(10) 0.0006(9) -0.0009(10) C26 0.0134(13) 0.0150(14) 0.0096(12) -0.0055(10) 0.0033(9) -0.0012(10) C27 0.0141(12) 0.0121(13) 0.0094(12) -0.0050(10) 0.0033(9) -0.0039(10) C28 0.0128(13) 0.0115(13) 0.0134(12) -0.0039(10) -0.0023(9) 0.0003(10) C29 0.0146(13) 0.0143(14) 0.0113(12) -0.0047(10) -0.0008(9) -0.0041(10) C30 0.0205(14) 0.0161(14) 0.0155(13) -0.0054(11) -0.0024(10) 0.0001(10) C31 0.0233(14) 0.0144(15) 0.0208(14) -0.0049(11) 0.0013(11) -0.0084(11) C32 0.0181(13) 0.0194(15) 0.0254(14) -0.0080(12) -0.0013(11) -0.0067(11) C33 0.0171(14) 0.0166(14) 0.0176(13) -0.0063(11) -0.0045(10) 0.0010(10) C34 0.0145(13) 0.0161(14) 0.0113(12) -0.0060(11) 0.0026(9) -0.0044(10) C35 0.0148(13) 0.0160(14) 0.0132(12) -0.0033(11) -0.0002(9) 0.0004(10) C36 0.0131(13) 0.0130(14) 0.0075(12) -0.0035(10) 0.0020(9) -0.0017(10) C37 0.0238(14) 0.0145(14) 0.0115(12) -0.0052(11) 0.0025(10) -0.0045(11) C38 0.0205(14) 0.0215(15) 0.0127(13) -0.0072(11) 0.0024(10) -0.0095(11) C39 0.0173(13) 0.0248(16) 0.0123(12) -0.0070(11) -0.0006(10) -0.0032(11) C40 0.0209(14) 0.0126(14) 0.0116(12) -0.0024(10) 0.0009(10) -0.0022(11) C41 0.0148(13) 0.0124(14) 0.0137(13) -0.0011(10) -0.0053(10) 0.0011(10) C42 0.0215(14) 0.0257(16) 0.0231(14) -0.0116(12) 0.0065(11) 0.0015(11) C43 0.0175(13) 0.0118(14) 0.0157(13) -0.0045(11) 0.0015(10) -0.0074(11) C44 0.0280(14) 0.0239(16) 0.0127(13) -0.0035(11) -0.0027(10) -0.0072(11) N1 0.0764(19) 0.053(2) 0.0329(17) 0.0028(15) 0.0045(14) -0.0098(15) C45 0.0576(18) 0.0180(17) 0.0273(16) -0.0012(13) 0.0011(13) -0.0031(13) C46 0.0395(17) 0.0242(17) 0.0336(18) -0.0073(14) 0.0009(13) -0.0036(13) N2 0.0340(14) 0.0471(18) 0.0368(15) -0.0161(14) -0.0025(11) 0.0050(13) C47 0.0329(15) 0.0295(18) 0.0295(16) -0.0078(14) -0.0050(12) -0.0031(13) C48 0.0224(15) 0.0313(18) 0.0247(15) -0.0134(13) 0.0032(12) -0.0063(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O3 1.4590(14) . ? P1 O2 1.5901(14) . ? P1 O1 1.6011(14) . ? P1 C24 1.804(2) . ? O1 C1 1.424(2) . ? O2 C13 1.427(2) . ? O4 C41 1.200(2) . ? O5 C41 1.330(2) . ? O5 C42 1.456(2) . ? O6 C43 1.203(2) . ? O7 C43 1.337(2) . ? O7 C44 1.456(2) . ? C1 C6 1.396(3) . ? C1 C2 1.404(3) . ? C2 C3 1.400(3) . ? C2 C14 1.543(3) . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(3) . ? C4 C18 1.514(3) . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 C7 1.514(3) . ? C7 C8 1.519(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.384(3) . ? C8 C13 1.391(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C10 C19 1.506(3) . ? C11 C12 1.405(3) . ? C11 H11 0.9500 . ? C12 C13 1.406(3) . ? C12 C20 1.540(3) . ? C14 C15 1.532(3) . ? C14 C16 1.537(3) . ? C14 C17 1.545(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C22 1.533(3) . ? C20 C23 1.538(3) . ? C20 C21 1.540(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C36 1.512(3) . ? C24 C25 1.515(3) . ? C24 H24 1.0000 . ? C25 C37 1.382(3) . ? C25 C26 1.395(3) . ? C26 C40 1.399(3) . ? C26 C27 1.472(3) . ? C27 C36 1.343(3) . ? C27 C28 1.517(3) . ? C28 C29 1.534(3) . ? C28 C43 1.545(3) . ? C28 C41 1.550(3) . ? C29 C30 1.394(3) . ? C29 C34 1.395(3) . ? C30 C31 1.385(3) . ? C30 H30 0.9500 . ? C31 C32 1.389(3) . ? C31 H31 0.9500 . ? C32 C33 1.386(3) . ? C32 H32 0.9500 . ? C33 C34 1.396(3) . ? C33 H33 0.9500 . ? C34 C35 1.510(3) . ? C35 C36 1.493(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C37 C38 1.395(3) . ? C37 H37 0.9500 . ? C38 C39 1.382(3) . ? C38 H38 0.9500 . ? C39 C40 1.392(3) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? N1 C46 1.135(3) . ? C45 C46 1.455(4) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? N2 C48 1.139(3) . ? C47 C48 1.464(3) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 P1 O2 114.07(8) . . ? O3 P1 O1 113.72(8) . . ? O2 P1 O1 109.43(7) . . ? O3 P1 C24 118.16(9) . . ? O2 P1 C24 101.44(9) . . ? O1 P1 C24 98.33(9) . . ? C1 O1 P1 124.72(13) . . ? C13 O2 P1 123.45(13) . . ? C41 O5 C42 114.56(17) . . ? C43 O7 C44 114.94(17) . . ? C6 C1 C2 123.2(2) . . ? C6 C1 O1 116.36(19) . . ? C2 C1 O1 120.20(19) . . ? C3 C2 C1 115.3(2) . . ? C3 C2 C14 120.1(2) . . ? C1 C2 C14 124.5(2) . . ? C4 C3 C2 123.6(2) . . ? C4 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 C18 121.5(2) . . ? C3 C4 C18 120.1(2) . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 120.13(19) . . ? C1 C6 C7 121.6(2) . . ? C6 C7 C8 114.37(17) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 118.52(18) . . ? C9 C8 C7 119.98(18) . . ? C13 C8 C7 121.48(19) . . ? C8 C9 C10 121.61(19) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 117.6(2) . . ? C11 C10 C19 121.64(18) . . ? C9 C10 C19 120.69(19) . . ? C10 C11 C12 124.29(19) . . ? C10 C11 H11 117.9 . . ? C12 C11 H11 117.9 . . ? C11 C12 C13 114.72(19) . . ? C11 C12 C20 120.31(17) . . ? C13 C12 C20 124.97(19) . . ? C8 C13 C12 123.09(19) . . ? C8 C13 O2 115.88(17) . . ? C12 C13 O2 120.87(18) . . ? C15 C14 C16 110.17(19) . . ? C15 C14 C2 109.80(17) . . ? C16 C14 C2 111.71(16) . . ? C15 C14 C17 106.85(17) . . ? C16 C14 C17 106.52(17) . . ? C2 C14 C17 111.64(18) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C20 C23 110.34(18) . . ? C22 C20 C21 105.90(19) . . ? C23 C20 C21 107.45(17) . . ? C22 C20 C12 111.88(16) . . ? C23 C20 C12 109.41(18) . . ? C21 C20 C12 111.74(17) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C36 C24 C25 102.31(17) . . ? C36 C24 P1 117.32(14) . . ? C25 C24 P1 113.58(14) . . ? C36 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? P1 C24 H24 107.7 . . ? C37 C25 C26 121.45(19) . . ? C37 C25 C24 129.2(2) . . ? C26 C25 C24 109.29(17) . . ? C25 C26 C40 120.23(18) . . ? C25 C26 C27 107.97(18) . . ? C40 C26 C27 131.8(2) . . ? C36 C27 C26 109.79(19) . . ? C36 C27 C28 122.93(18) . . ? C26 C27 C28 127.27(18) . . ? C27 C28 C29 111.55(18) . . ? C27 C28 C43 110.52(17) . . ? C29 C28 C43 108.80(17) . . ? C27 C28 C41 112.24(17) . . ? C29 C28 C41 108.76(17) . . ? C43 C28 C41 104.69(17) . . ? C30 C29 C34 119.54(19) . . ? C30 C29 C28 118.81(19) . . ? C34 C29 C28 121.59(19) . . ? C31 C30 C29 121.2(2) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C32 119.4(2) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C33 C32 C31 119.6(2) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C32 C33 C34 121.5(2) . . ? C32 C33 H33 119.3 . . ? C34 C33 H33 119.3 . . ? C29 C34 C33 118.8(2) . . ? C29 C34 C35 122.60(18) . . ? C33 C34 C35 118.6(2) . . ? C36 C35 C34 112.51(18) . . ? C36 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? C36 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.8 . . ? C27 C36 C35 124.5(2) . . ? C27 C36 C24 110.62(18) . . ? C35 C36 C24 124.79(19) . . ? C25 C37 C38 118.1(2) . . ? C25 C37 H37 120.9 . . ? C38 C37 H37 120.9 . . ? C39 C38 C37 120.93(19) . . ? C39 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 C39 C40 121.2(2) . . ? C38 C39 H39 119.4 . . ? C40 C39 H39 119.4 . . ? C39 C40 C26 118.1(2) . . ? C39 C40 H40 121.0 . . ? C26 C40 H40 121.0 . . ? O4 C41 O5 124.1(2) . . ? O4 C41 C28 123.81(19) . . ? O5 C41 C28 112.12(18) . . ? O5 C42 H42A 109.5 . . ? O5 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O5 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O6 C43 O7 124.8(2) . . ? O6 C43 C28 124.4(2) . . ? O7 C43 C28 110.75(18) . . ? O7 C44 H44A 109.5 . . ? O7 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O7 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 H45A 109.5 . . ? C46 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C46 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? N1 C46 C45 179.4(4) . . ? C48 C47 H47A 109.5 . . ? C48 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C48 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? N2 C48 C47 179.0(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.305 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.050 #===END