# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Brase, Stefan' _publ_contact_author_email braese@ioc.uka.de _publ_section_title ; Asymmetric Total Synthesis of (+)-Fumimycin via 1,2-Addition to Ketimines ; loop_ _publ_author_name P.J.Gross F.U.Furche M.Nieger S.Brase # Attachment 'ChemCommun-Gross.cif' data_sb158_hy_compound_6 _database_code_depnum_ccdc_archive 'CCDC 786071' #TrackingRef 'ChemCommun-Gross.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-ethyl 2-(6-(tert.butyldimethylsiloxyl)benzo[d][1,3]dioxol-5-yl)- 2-(diphenylphosphorylimino)acetate ; _chemical_name_common ; (Z)-ethyl 2-(6-(tert.butyldimethylsiloxyl)benzo(d)(1,3)dioxol- 5-yl)-2-(diphenylphosphorylimino)acetate ; _chemical_melting_point ? _chemical_formula_moiety 'C29 H34 N O6 P Si' _chemical_formula_sum 'C29 H34 N O6 P Si' _chemical_formula_weight 551.63 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' Si Si 0.0817 0.0704 '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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.199(1) _cell_length_b 16.574(2) _cell_length_c 17.054(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2882.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 17355 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.5 _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 20 sec./deg., 2 deg., 6 sets, 306 frames, scaling using SADABS ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41766 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6611 _reflns_number_gt 6192 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.8345P] 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 0.00(6) _refine_ls_number_reflns 6611 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0682 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 O1 O 0.56147(10) 0.46662(6) 0.48884(6) 0.0192(2) Uani 1 1 d . . . C2 C 0.69116(16) 0.44399(10) 0.46353(10) 0.0212(3) Uani 1 1 d . . . H2A H 0.7508 0.4399 0.5092 0.025 Uiso 1 1 calc R . . H2B H 0.6887 0.3910 0.4367 0.025 Uiso 1 1 calc R . . O3 O 0.73602(11) 0.50529(7) 0.41081(7) 0.0241(3) Uani 1 1 d . . . C3A C 0.62674(14) 0.54941(9) 0.39144(9) 0.0167(3) Uani 1 1 d . . . C4 C 0.61524(14) 0.61109(8) 0.33994(9) 0.0164(3) Uani 1 1 d . . . H4 H 0.6886 0.6292 0.3104 0.020 Uiso 1 1 calc R . . C5 C 0.49053(14) 0.64809(8) 0.33120(8) 0.0129(3) Uani 1 1 d . . . C6 C 0.38355(13) 0.61946(8) 0.37459(8) 0.0132(3) Uani 1 1 d . . . C7 C 0.39997(15) 0.55766(8) 0.43071(8) 0.0148(3) Uani 1 1 d . . . H7 H 0.3291 0.5399 0.4624 0.018 Uiso 1 1 calc R . . C7A C 0.52203(15) 0.52450(8) 0.43748(8) 0.0153(3) Uani 1 1 d . . . C8 C 0.48375(14) 0.71875(8) 0.27955(8) 0.0128(3) Uani 1 1 d . . . N9 N 0.58966(12) 0.74810(7) 0.25122(7) 0.0145(2) Uani 1 1 d . . . P1 P 0.60292(4) 0.83044(2) 0.19476(2) 0.01280(8) Uani 1 1 d . . . O10 O 0.48410(10) 0.86739(6) 0.16029(6) 0.0173(2) Uani 1 1 d . . . C11 C 0.68825(14) 0.89983(9) 0.25824(8) 0.0143(3) Uani 1 1 d . . . C12 C 0.63143(16) 0.97499(9) 0.27019(9) 0.0201(3) Uani 1 1 d . . . H12 H 0.5503 0.9878 0.2458 0.024 Uiso 1 1 calc R . . C13 C 0.69294(19) 1.03149(10) 0.31775(10) 0.0259(4) Uani 1 1 d . . . H13 H 0.6537 1.0828 0.3260 0.031 Uiso 1 1 calc R . . C14 C 0.81131(18) 1.01310(10) 0.35311(10) 0.0243(3) Uani 1 1 d . . . H14 H 0.8534 1.0518 0.3856 0.029 Uiso 1 1 calc R . . C15 C 0.86842(16) 0.93828(10) 0.34118(9) 0.0216(3) Uani 1 1 d . . . H15 H 0.9497 0.9257 0.3655 0.026 Uiso 1 1 calc R . . C16 C 0.80737(15) 0.88178(9) 0.29392(9) 0.0190(3) Uani 1 1 d . . . H16 H 0.8469 0.8305 0.2858 0.023 Uiso 1 1 calc R . . C17 C 0.71712(14) 0.79833(9) 0.12059(9) 0.0151(3) Uani 1 1 d . . . C18 C 0.81925(17) 0.74475(11) 0.13512(9) 0.0254(4) Uani 1 1 d . . . H18 H 0.8289 0.7215 0.1857 0.030 Uiso 1 1 calc R . . C19 C 0.90645(19) 0.72527(12) 0.07645(10) 0.0331(4) Uani 1 1 d . . . H19 H 0.9776 0.6899 0.0871 0.040 Uiso 1 1 calc R . . C20 C 0.89078(18) 0.75711(11) 0.00188(10) 0.0297(4) Uani 1 1 d . . . H20 H 0.9501 0.7429 -0.0388 0.036 Uiso 1 1 calc R . . C21 C 0.78837(18) 0.80969(10) -0.01310(10) 0.0260(4) Uani 1 1 d . . . H21 H 0.7771 0.8312 -0.0643 0.031 Uiso 1 1 calc R . . C22 C 0.70232(15) 0.83109(9) 0.04600(9) 0.0186(3) Uani 1 1 d . . . H22 H 0.6333 0.8681 0.0357 0.022 Uiso 1 1 calc R . . O23 O 0.28514(10) 0.73171(7) 0.20538(6) 0.0202(2) Uani 1 1 d . . . C23 C 0.35231(14) 0.75617(9) 0.25750(8) 0.0152(3) Uani 1 1 d . . . O24 O 0.33102(10) 0.82235(6) 0.30004(6) 0.0185(2) Uani 1 1 d . . . C25 C 0.22765(17) 0.87527(10) 0.27166(10) 0.0262(4) Uani 1 1 d . . . H25A H 0.1410 0.8492 0.2780 0.031 Uiso 1 1 calc R . . H25B H 0.2410 0.8876 0.2154 0.031 Uiso 1 1 calc R . . C26 C 0.2343(2) 0.95113(11) 0.31946(15) 0.0412(5) Uani 1 1 d . . . H26A H 0.1658 0.9885 0.3020 0.062 Uiso 1 1 calc R . . H26B H 0.3205 0.9763 0.3126 0.062 Uiso 1 1 calc R . . H26C H 0.2209 0.9381 0.3749 0.062 Uiso 1 1 calc R . . O6 O 0.26473(10) 0.65343(6) 0.36337(6) 0.0165(2) Uani 1 1 d . . . Si6 Si 0.10923(4) 0.62485(2) 0.38116(2) 0.01421(8) Uani 1 1 d . . . C61 C 0.01729(16) 0.65572(11) 0.29203(9) 0.0240(3) Uani 1 1 d . . . H61A H 0.0260 0.7141 0.2845 0.036 Uiso 1 1 calc R . . H61B H -0.0755 0.6419 0.2983 0.036 Uiso 1 1 calc R . . H61C H 0.0529 0.6275 0.2463 0.036 Uiso 1 1 calc R . . C62 C 0.09173(16) 0.51413(9) 0.39464(10) 0.0248(3) Uani 1 1 d . . . H62A H 0.1401 0.4973 0.4415 0.037 Uiso 1 1 calc R . . H62B H 0.1270 0.4861 0.3486 0.037 Uiso 1 1 calc R . . H62C H -0.0012 0.5005 0.4009 0.037 Uiso 1 1 calc R . . C63 C 0.05577(14) 0.68391(9) 0.46925(9) 0.0167(3) Uani 1 1 d . . . C64 C 0.14679(16) 0.66685(11) 0.53874(9) 0.0235(3) Uani 1 1 d . . . H64A H 0.1443 0.6092 0.5513 0.035 Uiso 1 1 calc R . . H64B H 0.1177 0.6981 0.5844 0.035 Uiso 1 1 calc R . . H64C H 0.2366 0.6824 0.5250 0.035 Uiso 1 1 calc R . . C65 C -0.08458(15) 0.66057(11) 0.49232(10) 0.0269(4) Uani 1 1 d . . . H65A H -0.0880 0.6028 0.5043 0.040 Uiso 1 1 calc R . . H65B H -0.1442 0.6725 0.4487 0.040 Uiso 1 1 calc R . . H65C H -0.1112 0.6915 0.5386 0.040 Uiso 1 1 calc R . . C66 C 0.06069(17) 0.77422(9) 0.45005(10) 0.0236(3) Uani 1 1 d . . . H66A H 0.0023 0.7856 0.4058 0.035 Uiso 1 1 calc R . . H66B H 0.1506 0.7894 0.4362 0.035 Uiso 1 1 calc R . . H66C H 0.0323 0.8053 0.4959 0.035 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 O1 0.0198(5) 0.0181(5) 0.0197(5) 0.0053(4) -0.0048(4) 0.0009(4) C2 0.0185(7) 0.0197(7) 0.0254(8) 0.0041(6) -0.0061(6) 0.0016(6) O3 0.0137(5) 0.0202(5) 0.0384(7) 0.0101(5) -0.0030(5) 0.0029(4) C3A 0.0120(6) 0.0150(6) 0.0232(7) -0.0015(6) -0.0043(6) 0.0010(5) C4 0.0121(6) 0.0158(7) 0.0213(7) 0.0005(5) 0.0002(6) -0.0017(5) C5 0.0142(7) 0.0114(6) 0.0132(6) -0.0011(5) 0.0000(5) -0.0004(5) C6 0.0125(6) 0.0148(6) 0.0122(6) -0.0028(5) -0.0004(5) 0.0003(5) C7 0.0155(6) 0.0148(6) 0.0142(6) 0.0004(5) 0.0015(6) -0.0011(6) C7A 0.0199(7) 0.0119(6) 0.0143(6) -0.0013(5) -0.0037(6) -0.0014(5) C8 0.0152(6) 0.0129(6) 0.0103(6) -0.0033(5) -0.0006(5) 0.0007(5) N9 0.0159(6) 0.0144(5) 0.0131(5) 0.0008(4) -0.0003(5) -0.0002(5) P1 0.01359(16) 0.01319(16) 0.01161(15) 0.00154(13) 0.00053(14) -0.00003(14) O10 0.0162(5) 0.0189(5) 0.0169(5) 0.0025(4) -0.0002(4) 0.0014(4) C11 0.0164(7) 0.0150(7) 0.0116(6) 0.0019(5) 0.0022(5) -0.0023(5) C12 0.0254(8) 0.0177(7) 0.0173(7) 0.0013(6) -0.0037(6) 0.0031(6) C13 0.0387(9) 0.0139(7) 0.0251(8) -0.0017(6) -0.0046(7) 0.0031(7) C14 0.0329(9) 0.0189(8) 0.0211(8) -0.0006(6) -0.0034(7) -0.0065(7) C15 0.0188(8) 0.0248(8) 0.0213(7) 0.0013(6) -0.0017(6) -0.0028(6) C16 0.0169(7) 0.0193(7) 0.0207(7) 0.0004(6) 0.0003(6) 0.0012(6) C17 0.0154(7) 0.0156(6) 0.0143(6) -0.0020(5) 0.0014(5) -0.0011(5) C18 0.0303(9) 0.0296(9) 0.0164(8) 0.0006(6) 0.0003(7) 0.0113(7) C19 0.0314(9) 0.0401(10) 0.0279(9) -0.0011(7) 0.0041(8) 0.0200(9) C20 0.0330(9) 0.0335(9) 0.0225(8) -0.0034(6) 0.0112(8) 0.0072(8) C21 0.0369(10) 0.0261(9) 0.0149(7) 0.0011(6) 0.0061(7) 0.0018(7) C22 0.0214(7) 0.0166(7) 0.0176(7) 0.0009(6) 0.0006(6) 0.0004(6) O23 0.0193(5) 0.0240(5) 0.0174(5) 0.0028(4) -0.0037(4) -0.0007(4) C23 0.0155(7) 0.0162(7) 0.0139(7) 0.0028(5) 0.0032(5) -0.0002(5) O24 0.0208(5) 0.0166(5) 0.0181(5) 0.0004(4) 0.0026(4) 0.0061(4) C25 0.0242(8) 0.0242(8) 0.0302(9) 0.0074(7) 0.0051(7) 0.0122(7) C26 0.0286(10) 0.0204(8) 0.0747(16) -0.0004(9) 0.0106(10) 0.0060(7) O6 0.0114(5) 0.0186(5) 0.0195(5) 0.0048(4) 0.0026(4) 0.0029(4) Si6 0.01173(17) 0.01648(18) 0.01443(18) -0.00043(14) 0.00065(15) 0.00126(16) C61 0.0182(7) 0.0357(9) 0.0181(8) 0.0002(7) -0.0035(6) 0.0021(7) C62 0.0200(7) 0.0175(7) 0.0369(9) -0.0008(6) 0.0027(7) -0.0015(6) C63 0.0154(7) 0.0189(7) 0.0158(7) -0.0020(6) 0.0012(5) 0.0021(6) C64 0.0269(8) 0.0279(8) 0.0156(7) 0.0003(6) -0.0008(6) 0.0046(7) C65 0.0186(7) 0.0349(9) 0.0271(8) -0.0044(7) 0.0089(6) -0.0003(7) C66 0.0267(8) 0.0201(8) 0.0240(8) -0.0039(6) -0.0010(6) 0.0055(6) _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 O1 C7A 1.3598(17) . ? O1 C2 1.4410(19) . ? C2 O3 1.4318(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3 C3A 1.3733(17) . ? C3A C4 1.353(2) . ? C3A C7A 1.388(2) . ? C4 C5 1.420(2) . ? C4 H4 0.9500 . ? C5 C6 1.4012(19) . ? C5 C8 1.4670(19) . ? C6 O6 1.3499(17) . ? C6 C7 1.4116(19) . ? C7 C7A 1.366(2) . ? C7 H7 0.9500 . ? C8 N9 1.2794(19) . ? C8 C23 1.524(2) . ? N9 P1 1.6757(12) . ? P1 O10 1.4796(11) . ? P1 C17 1.7999(15) . ? P1 C11 1.8034(15) . ? C11 C12 1.389(2) . ? C11 C16 1.391(2) . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.391(2) . ? C17 C22 1.391(2) . ? C18 C19 1.377(2) . ? C18 H18 0.9500 . ? C19 C20 1.386(2) . ? C19 H19 0.9500 . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? O23 C23 1.1931(18) . ? C23 O24 1.3328(18) . ? O24 C25 1.4543(18) . ? C25 C26 1.500(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O6 Si6 1.6828(11) . ? Si6 C61 1.8578(16) . ? Si6 C62 1.8580(16) . ? Si6 C63 1.8741(15) . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63 C64 1.532(2) . ? C63 C66 1.533(2) . ? C63 C65 1.534(2) . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 H65C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 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 C7A O1 C2 105.20(12) . . ? O3 C2 O1 107.26(12) . . ? O3 C2 H2A 110.3 . . ? O1 C2 H2A 110.3 . . ? O3 C2 H2B 110.3 . . ? O1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C3A O3 C2 105.64(11) . . ? C4 C3A O3 128.97(14) . . ? C4 C3A C7A 121.68(13) . . ? O3 C3A C7A 109.26(13) . . ? C3A C4 C5 118.18(13) . . ? C3A C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 119.72(13) . . ? C6 C5 C8 123.42(13) . . ? C4 C5 C8 116.75(13) . . ? O6 C6 C5 118.88(12) . . ? O6 C6 C7 120.34(13) . . ? C5 C6 C7 120.76(13) . . ? C7A C7 C6 117.22(13) . . ? C7A C7 H7 121.4 . . ? C6 C7 H7 121.4 . . ? O1 C7A C7 127.45(13) . . ? O1 C7A C3A 110.28(13) . . ? C7 C7A C3A 122.25(13) . . ? N9 C8 C5 119.37(13) . . ? N9 C8 C23 119.65(12) . . ? C5 C8 C23 120.96(12) . . ? C8 N9 P1 126.50(11) . . ? O10 P1 N9 119.95(6) . . ? O10 P1 C17 111.91(7) . . ? N9 P1 C17 102.43(7) . . ? O10 P1 C11 111.71(7) . . ? N9 P1 C11 102.32(6) . . ? C17 P1 C11 107.35(7) . . ? C12 C11 C16 119.55(14) . . ? C12 C11 P1 117.30(11) . . ? C16 C11 P1 123.15(11) . . ? C13 C12 C11 120.13(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.02(15) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.01(15) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.15(15) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.14(14) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C18 C17 C22 119.56(14) . . ? C18 C17 P1 123.24(12) . . ? C22 C17 P1 117.19(11) . . ? C19 C18 C17 120.25(15) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.19(16) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 119.74(15) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.40(15) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C17 119.83(14) . . ? C21 C22 H22 120.1 . . ? C17 C22 H22 120.1 . . ? O23 C23 O24 126.26(14) . . ? O23 C23 C8 123.40(13) . . ? O24 C23 C8 110.12(12) . . ? C23 O24 C25 115.68(12) . . ? O24 C25 C26 106.98(15) . . ? O24 C25 H25A 110.3 . . ? C26 C25 H25A 110.3 . . ? O24 C25 H25B 110.3 . . ? C26 C25 H25B 110.3 . . ? H25A C25 H25B 108.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C6 O6 Si6 134.68(9) . . ? O6 Si6 C61 104.52(7) . . ? O6 Si6 C62 113.01(6) . . ? C61 Si6 C62 108.95(8) . . ? O6 Si6 C63 105.77(6) . . ? C61 Si6 C63 111.41(7) . . ? C62 Si6 C63 112.88(7) . . ? Si6 C61 H61A 109.5 . . ? Si6 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? Si6 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? Si6 C62 H62A 109.5 . . ? Si6 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? Si6 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 C66 109.00(13) . . ? C64 C63 C65 108.69(13) . . ? C66 C63 C65 109.36(13) . . ? C64 C63 Si6 110.33(10) . . ? C66 C63 Si6 109.22(11) . . ? C65 C63 Si6 110.21(11) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C63 C65 H65A 109.5 . . ? C63 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C63 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C63 C66 H66A 109.5 . . ? C63 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C63 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A O1 C2 O3 15.43(15) . . . . ? O1 C2 O3 C3A -14.21(16) . . . . ? C2 O3 C3A C4 -175.76(15) . . . . ? C2 O3 C3A C7A 7.68(16) . . . . ? O3 C3A C4 C5 -178.99(14) . . . . ? C7A C3A C4 C5 -2.8(2) . . . . ? C3A C4 C5 C6 -0.9(2) . . . . ? C3A C4 C5 C8 175.37(13) . . . . ? C4 C5 C6 O6 -177.58(12) . . . . ? C8 C5 C6 O6 6.4(2) . . . . ? C4 C5 C6 C7 4.1(2) . . . . ? C8 C5 C6 C7 -171.92(13) . . . . ? O6 C6 C7 C7A 178.26(12) . . . . ? C5 C6 C7 C7A -3.5(2) . . . . ? C2 O1 C7A C7 170.99(14) . . . . ? C2 O1 C7A C3A -10.89(15) . . . . ? C6 C7 C7A O1 177.65(13) . . . . ? C6 C7 C7A C3A -0.3(2) . . . . ? C4 C3A C7A O1 -174.72(13) . . . . ? O3 C3A C7A O1 2.13(17) . . . . ? C4 C3A C7A C7 3.5(2) . . . . ? O3 C3A C7A C7 -179.63(13) . . . . ? C6 C5 C8 N9 169.64(13) . . . . ? C4 C5 C8 N9 -6.52(19) . . . . ? C6 C5 C8 C23 -12.0(2) . . . . ? C4 C5 C8 C23 171.83(12) . . . . ? C5 C8 N9 P1 -177.08(10) . . . . ? C23 C8 N9 P1 4.55(19) . . . . ? C8 N9 P1 O10 -12.09(15) . . . . ? C8 N9 P1 C17 -136.70(13) . . . . ? C8 N9 P1 C11 112.16(13) . . . . ? O10 P1 C11 C12 3.21(14) . . . . ? N9 P1 C11 C12 -126.35(12) . . . . ? C17 P1 C11 C12 126.25(12) . . . . ? O10 P1 C11 C16 -175.73(12) . . . . ? N9 P1 C11 C16 54.70(13) . . . . ? C17 P1 C11 C16 -52.69(14) . . . . ? C16 C11 C12 C13 -0.3(2) . . . . ? P1 C11 C12 C13 -179.30(12) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 0.2(2) . . . . ? P1 C11 C16 C15 179.15(12) . . . . ? O10 P1 C17 C18 -163.42(13) . . . . ? N9 P1 C17 C18 -33.66(15) . . . . ? C11 P1 C17 C18 73.66(15) . . . . ? O10 P1 C17 C22 18.17(14) . . . . ? N9 P1 C17 C22 147.93(11) . . . . ? C11 P1 C17 C22 -104.75(12) . . . . ? C22 C17 C18 C19 1.1(3) . . . . ? P1 C17 C18 C19 -177.29(14) . . . . ? C17 C18 C19 C20 -1.9(3) . . . . ? C18 C19 C20 C21 1.1(3) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C17 -1.3(3) . . . . ? C18 C17 C22 C21 0.5(2) . . . . ? P1 C17 C22 C21 178.99(12) . . . . ? N9 C8 C23 O23 94.76(18) . . . . ? C5 C8 C23 O23 -83.58(18) . . . . ? N9 C8 C23 O24 -80.12(16) . . . . ? C5 C8 C23 O24 101.53(14) . . . . ? O23 C23 O24 C25 -10.1(2) . . . . ? C8 C23 O24 C25 164.65(12) . . . . ? C23 O24 C25 C26 -171.16(14) . . . . ? C5 C6 O6 Si6 159.94(10) . . . . ? C7 C6 O6 Si6 -21.8(2) . . . . ? C6 O6 Si6 C61 -137.53(13) . . . . ? C6 O6 Si6 C62 -19.21(15) . . . . ? C6 O6 Si6 C63 104.76(13) . . . . ? O6 Si6 C63 C64 -58.30(12) . . . . ? C61 Si6 C63 C64 -171.29(11) . . . . ? C62 Si6 C63 C64 65.75(13) . . . . ? O6 Si6 C63 C66 61.50(11) . . . . ? C61 Si6 C63 C66 -51.50(13) . . . . ? C62 Si6 C63 C66 -174.45(11) . . . . ? O6 Si6 C63 C65 -178.34(10) . . . . ? C61 Si6 C63 C65 68.67(13) . . . . ? C62 Si6 C63 C65 -54.29(13) . . . . ? 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 C2 H2B O10 0.99 2.45 3.0440(19) 118.2 3_645 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.297 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.042 #============================================================================== data_sb162_hy_compound_9 _database_code_depnum_ccdc_archive 'CCDC 786072' #TrackingRef 'ChemCommun-Gross.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-ethyl-2-(diphenylphosphorylimino)-2-(6-hydroxybenzo[d][1,3]dioxol- 5-yl)acetate ; _chemical_name_common ; (Z)-ethyl-2-(diphenylphosphorylimino)-2-(6- hydroxybenzo(d)(1,3)dioxol-5-yl)acetate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 N O6 P' _chemical_formula_sum 'C23 H20 N O6 P' _chemical_formula_weight 437.37 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 8.475(1) _cell_length_b 11.476(1) _cell_length_c 11.734(1) _cell_angle_alpha 103.66(1) _cell_angle_beta 107.51(1) _cell_angle_gamma 94.34(1) _cell_volume 1044.23(18) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5535 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 40 sec./deg., 2 deg., 5 sets, 182 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10736 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4749 _reflns_number_gt 4163 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.4262P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4749 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 O1 O 0.42482(13) 0.79863(8) 0.12288(8) 0.0208(2) Uani 1 1 d . . . C2 C 0.37140(18) 0.91377(11) 0.11348(12) 0.0200(3) Uani 1 1 d . . . H2A H 0.4676 0.9737 0.1223 0.024 Uiso 1 1 calc R . . H2B H 0.2851 0.9039 0.0318 0.024 Uiso 1 1 calc R . . O3 O 0.30365(13) 0.95403(8) 0.21193(9) 0.0228(2) Uani 1 1 d . . . C3A C 0.34210(17) 0.87707(11) 0.28660(12) 0.0175(3) Uani 1 1 d . . . C4 C 0.31848(16) 0.88359(11) 0.39710(12) 0.0172(3) Uani 1 1 d . . . H4 H 0.2686 0.9472 0.4335 0.021 Uiso 1 1 calc R . . C5 C 0.37121(16) 0.79139(11) 0.45691(11) 0.0155(2) Uani 1 1 d . . . C6 C 0.44327(16) 0.69711(11) 0.39891(12) 0.0165(2) Uani 1 1 d . . . O6 O 0.49502(13) 0.60765(8) 0.45034(9) 0.0210(2) Uani 1 1 d D . . H6 H 0.484(2) 0.6232(16) 0.5215(14) 0.031 Uiso 1 1 d D . . C7 C 0.46489(17) 0.69247(11) 0.28399(12) 0.0189(3) Uani 1 1 d . . . H7 H 0.5122 0.6290 0.2445 0.023 Uiso 1 1 calc R . . C7A C 0.41440(16) 0.78387(11) 0.23168(12) 0.0168(3) Uani 1 1 d . . . C8 C 0.35398(15) 0.79536(11) 0.57632(11) 0.0149(2) Uani 1 1 d . . . N9 N 0.41667(14) 0.72026(9) 0.63857(10) 0.0165(2) Uani 1 1 d . . . P1 P 0.42320(4) 0.72836(3) 0.78490(3) 0.01468(9) Uani 1 1 d . . . O10 O 0.36834(12) 0.83596(8) 0.85108(8) 0.0191(2) Uani 1 1 d . . . C11 C 0.30557(16) 0.58506(11) 0.77055(12) 0.0160(2) Uani 1 1 d . . . C12 C 0.32457(17) 0.54839(11) 0.87880(12) 0.0186(3) Uani 1 1 d . . . H12 H 0.4003 0.5973 0.9560 0.022 Uiso 1 1 calc R . . C13 C 0.23276(18) 0.44041(12) 0.87355(13) 0.0232(3) Uani 1 1 d . . . H13 H 0.2459 0.4154 0.9470 0.028 Uiso 1 1 calc R . . C14 C 0.12188(19) 0.36921(12) 0.76072(14) 0.0258(3) Uani 1 1 d . . . H14 H 0.0592 0.2955 0.7573 0.031 Uiso 1 1 calc R . . C15 C 0.10213(19) 0.40510(13) 0.65313(14) 0.0260(3) Uani 1 1 d . . . H15 H 0.0256 0.3563 0.5762 0.031 Uiso 1 1 calc R . . C16 C 0.19460(18) 0.51285(12) 0.65782(13) 0.0217(3) Uani 1 1 d . . . H16 H 0.1819 0.5371 0.5839 0.026 Uiso 1 1 calc R . . C17 C 0.64105(16) 0.72165(11) 0.85717(12) 0.0176(3) Uani 1 1 d . . . C18 C 0.71725(18) 0.63036(12) 0.80365(13) 0.0222(3) Uani 1 1 d . . . H18 H 0.6532 0.5693 0.7303 0.027 Uiso 1 1 calc R . . C19 C 0.88666(19) 0.62881(14) 0.85763(15) 0.0282(3) Uani 1 1 d . . . H19 H 0.9387 0.5665 0.8215 0.034 Uiso 1 1 calc R . . C20 C 0.98012(19) 0.71837(14) 0.96452(15) 0.0305(3) Uani 1 1 d . . . H20 H 1.0962 0.7173 1.0012 0.037 Uiso 1 1 calc R . . C21 C 0.90510(19) 0.80923(13) 1.01799(14) 0.0280(3) Uani 1 1 d . . . H21 H 0.9699 0.8705 1.0909 0.034 Uiso 1 1 calc R . . C22 C 0.73502(18) 0.81100(12) 0.96506(13) 0.0221(3) Uani 1 1 d . . . H22 H 0.6831 0.8728 1.0022 0.027 Uiso 1 1 calc R . . C23 C 0.25288(16) 0.88765(11) 0.62499(11) 0.0161(2) Uani 1 1 d . . . O23 O 0.29607(13) 0.99567(8) 0.66225(9) 0.0222(2) Uani 1 1 d . . . O24 O 0.10741(11) 0.82667(8) 0.61523(9) 0.0199(2) Uani 1 1 d . . . C24 C -0.00083(19) 0.89378(13) 0.67270(14) 0.0272(3) Uani 1 1 d . . . H24A H -0.0026 0.9746 0.6566 0.033 Uiso 1 1 calc R . . H24B H 0.0396 0.9051 0.7636 0.033 Uiso 1 1 calc R . . C25 C -0.1720(2) 0.81955(15) 0.61551(18) 0.0369(4) Uani 1 1 d . . . H25A H -0.2500 0.8615 0.6508 0.055 Uiso 1 1 calc R . . H25B H -0.1683 0.7401 0.6327 0.055 Uiso 1 1 calc R . . H25C H -0.2097 0.8084 0.5255 0.055 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 O1 0.0315(5) 0.0179(4) 0.0167(5) 0.0061(3) 0.0116(4) 0.0052(4) C2 0.0277(7) 0.0168(6) 0.0170(6) 0.0052(5) 0.0092(5) 0.0028(5) O3 0.0343(6) 0.0225(5) 0.0184(5) 0.0109(4) 0.0127(4) 0.0114(4) C3A 0.0186(6) 0.0166(6) 0.0179(6) 0.0066(5) 0.0052(5) 0.0027(5) C4 0.0178(6) 0.0171(6) 0.0182(6) 0.0050(5) 0.0073(5) 0.0050(5) C5 0.0145(6) 0.0163(6) 0.0163(6) 0.0049(5) 0.0058(5) 0.0021(4) C6 0.0160(6) 0.0153(6) 0.0182(6) 0.0055(5) 0.0051(5) 0.0023(4) O6 0.0305(5) 0.0189(4) 0.0196(5) 0.0090(4) 0.0126(4) 0.0107(4) C7 0.0225(7) 0.0166(6) 0.0192(6) 0.0034(5) 0.0098(5) 0.0050(5) C7A 0.0180(6) 0.0167(6) 0.0148(6) 0.0026(5) 0.0059(5) -0.0006(5) C8 0.0128(6) 0.0152(5) 0.0159(6) 0.0032(4) 0.0045(5) 0.0007(4) N9 0.0180(5) 0.0173(5) 0.0162(5) 0.0062(4) 0.0072(4) 0.0039(4) P1 0.01643(17) 0.01474(16) 0.01405(16) 0.00519(12) 0.00564(12) 0.00290(12) O10 0.0233(5) 0.0171(4) 0.0183(5) 0.0049(3) 0.0083(4) 0.0048(4) C11 0.0157(6) 0.0153(5) 0.0182(6) 0.0050(5) 0.0070(5) 0.0036(4) C12 0.0206(7) 0.0183(6) 0.0173(6) 0.0048(5) 0.0068(5) 0.0031(5) C13 0.0267(7) 0.0224(6) 0.0245(7) 0.0109(5) 0.0109(6) 0.0036(5) C14 0.0259(7) 0.0182(6) 0.0337(8) 0.0070(6) 0.0114(6) -0.0004(5) C15 0.0248(7) 0.0222(7) 0.0244(7) 0.0003(5) 0.0049(6) -0.0030(5) C16 0.0223(7) 0.0233(6) 0.0184(6) 0.0055(5) 0.0056(5) 0.0018(5) C17 0.0172(6) 0.0181(6) 0.0187(6) 0.0084(5) 0.0056(5) 0.0014(5) C18 0.0207(7) 0.0230(6) 0.0216(7) 0.0055(5) 0.0056(5) 0.0036(5) C19 0.0225(7) 0.0305(7) 0.0334(8) 0.0091(6) 0.0100(6) 0.0094(6) C20 0.0169(7) 0.0342(8) 0.0377(9) 0.0126(7) 0.0034(6) 0.0025(6) C21 0.0224(7) 0.0243(7) 0.0291(8) 0.0049(6) 0.0005(6) -0.0035(5) C22 0.0233(7) 0.0190(6) 0.0234(7) 0.0068(5) 0.0062(6) 0.0026(5) C23 0.0168(6) 0.0187(6) 0.0137(6) 0.0055(5) 0.0049(5) 0.0044(5) O23 0.0271(5) 0.0156(4) 0.0255(5) 0.0047(4) 0.0114(4) 0.0031(4) O24 0.0149(5) 0.0196(4) 0.0237(5) 0.0001(4) 0.0085(4) 0.0029(3) C24 0.0221(7) 0.0286(7) 0.0305(8) -0.0001(6) 0.0132(6) 0.0089(6) C25 0.0263(8) 0.0293(8) 0.0601(11) 0.0054(7) 0.0262(8) 0.0046(6) _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 O1 C7A 1.3542(15) . ? O1 C2 1.4466(15) . ? C2 O3 1.4369(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3 C3A 1.3751(15) . ? C3A C4 1.3563(18) . ? C3A C7A 1.3950(18) . ? C4 C5 1.4302(17) . ? C4 H4 0.9500 . ? C5 C6 1.4175(18) . ? C5 C8 1.4425(17) . ? C6 O6 1.3461(15) . ? C6 C7 1.4039(18) . ? O6 H6 0.846(14) . ? C7 C7A 1.3689(18) . ? C7 H7 0.9500 . ? C8 N9 1.3006(16) . ? C8 C23 1.5258(17) . ? N9 P1 1.6812(11) . ? P1 O10 1.4816(10) . ? P1 C17 1.8011(14) . ? P1 C11 1.8019(13) . ? C11 C16 1.3916(19) . ? C11 C12 1.3987(17) . ? C12 C13 1.3906(18) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.3933(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.3945(19) . ? C17 C22 1.3946(19) . ? C18 C19 1.387(2) . ? C18 H18 0.9500 . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 C22 1.391(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 O23 1.2005(16) . ? C23 O24 1.3302(16) . ? O24 C24 1.4572(16) . ? C24 C25 1.496(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C7A O1 C2 106.41(10) . . ? O3 C2 O1 106.95(9) . . ? O3 C2 H2A 110.3 . . ? O1 C2 H2A 110.3 . . ? O3 C2 H2B 110.3 . . ? O1 C2 H2B 110.3 . . ? H2A C2 H2B 108.6 . . ? C3A O3 C2 106.19(10) . . ? C4 C3A O3 128.86(12) . . ? C4 C3A C7A 121.80(12) . . ? O3 C3A C7A 109.35(11) . . ? C3A C4 C5 117.72(12) . . ? C3A C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? C6 C5 C4 119.48(11) . . ? C6 C5 C8 120.19(11) . . ? C4 C5 C8 120.33(11) . . ? O6 C6 C7 116.31(11) . . ? O6 C6 C5 122.29(11) . . ? C7 C6 C5 121.40(11) . . ? C6 O6 H6 108.0(12) . . ? C7A C7 C6 116.71(12) . . ? C7A C7 H7 121.6 . . ? C6 C7 H7 121.6 . . ? O1 C7A C7 126.96(12) . . ? O1 C7A C3A 110.15(11) . . ? C7 C7A C3A 122.89(12) . . ? N9 C8 C5 121.52(11) . . ? N9 C8 C23 120.89(11) . . ? C5 C8 C23 117.55(11) . . ? C8 N9 P1 124.87(9) . . ? O10 P1 N9 116.98(5) . . ? O10 P1 C17 112.38(6) . . ? N9 P1 C17 101.10(6) . . ? O10 P1 C11 114.39(6) . . ? N9 P1 C11 103.46(6) . . ? C17 P1 C11 107.18(6) . . ? C16 C11 C12 119.62(12) . . ? C16 C11 P1 122.64(10) . . ? C12 C11 P1 117.71(10) . . ? C13 C12 C11 120.06(12) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.90(12) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.37(12) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.94(13) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 120.12(12) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C22 119.99(13) . . ? C18 C17 P1 120.46(10) . . ? C22 C17 P1 119.52(10) . . ? C19 C18 C17 119.92(13) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.95(14) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 120.36(14) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.10(14) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 119.68(13) . . ? C21 C22 H22 120.2 . . ? C17 C22 H22 120.2 . . ? O23 C23 O24 126.65(12) . . ? O23 C23 C8 125.88(12) . . ? O24 C23 C8 107.45(10) . . ? C23 O24 C24 117.30(10) . . ? O24 C24 C25 106.37(12) . . ? O24 C24 H24A 110.5 . . ? C25 C24 H24A 110.5 . . ? O24 C24 H24B 110.5 . . ? C25 C24 H24B 110.5 . . ? H24A C24 H24B 108.6 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A O1 C2 O3 -9.44(13) . . . . ? O1 C2 O3 C3A 9.58(13) . . . . ? C2 O3 C3A C4 173.63(13) . . . . ? C2 O3 C3A C7A -6.25(14) . . . . ? O3 C3A C4 C5 -179.56(12) . . . . ? C7A C3A C4 C5 0.31(19) . . . . ? C3A C4 C5 C6 -0.76(18) . . . . ? C3A C4 C5 C8 178.17(12) . . . . ? C4 C5 C6 O6 -179.86(12) . . . . ? C8 C5 C6 O6 1.21(19) . . . . ? C4 C5 C6 C7 0.32(19) . . . . ? C8 C5 C6 C7 -178.61(12) . . . . ? O6 C6 C7 C7A -179.26(12) . . . . ? C5 C6 C7 C7A 0.57(19) . . . . ? C2 O1 C7A C7 -174.48(13) . . . . ? C2 O1 C7A C3A 5.74(14) . . . . ? C6 C7 C7A O1 179.20(12) . . . . ? C6 C7 C7A C3A -1.05(19) . . . . ? C4 C3A C7A O1 -179.59(12) . . . . ? O3 C3A C7A O1 0.31(15) . . . . ? C4 C3A C7A C7 0.6(2) . . . . ? O3 C3A C7A C7 -179.48(12) . . . . ? C6 C5 C8 N9 6.23(18) . . . . ? C4 C5 C8 N9 -172.69(12) . . . . ? C6 C5 C8 C23 -171.26(11) . . . . ? C4 C5 C8 C23 9.82(17) . . . . ? C5 C8 N9 P1 172.31(9) . . . . ? C23 C8 N9 P1 -10.28(17) . . . . ? C8 N9 P1 O10 -6.24(13) . . . . ? C8 N9 P1 C17 -128.61(11) . . . . ? C8 N9 P1 C11 120.51(11) . . . . ? O10 P1 C11 C16 109.30(12) . . . . ? N9 P1 C11 C16 -19.07(13) . . . . ? C17 P1 C11 C16 -125.40(12) . . . . ? O10 P1 C11 C12 -68.71(12) . . . . ? N9 P1 C11 C12 162.92(10) . . . . ? C17 P1 C11 C12 56.59(12) . . . . ? C16 C11 C12 C13 -0.1(2) . . . . ? P1 C11 C12 C13 177.99(10) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? C12 C11 C16 C15 0.5(2) . . . . ? P1 C11 C16 C15 -177.51(11) . . . . ? C14 C15 C16 C11 -0.6(2) . . . . ? O10 P1 C17 C18 -176.31(10) . . . . ? N9 P1 C17 C18 -50.80(11) . . . . ? C11 P1 C17 C18 57.19(12) . . . . ? O10 P1 C17 C22 1.49(12) . . . . ? N9 P1 C17 C22 127.00(10) . . . . ? C11 P1 C17 C22 -125.01(10) . . . . ? C22 C17 C18 C19 -0.2(2) . . . . ? P1 C17 C18 C19 177.57(11) . . . . ? C17 C18 C19 C20 -0.2(2) . . . . ? C18 C19 C20 C21 0.2(2) . . . . ? C19 C20 C21 C22 0.3(2) . . . . ? C20 C21 C22 C17 -0.7(2) . . . . ? C18 C17 C22 C21 0.71(19) . . . . ? P1 C17 C22 C21 -177.10(10) . . . . ? N9 C8 C23 O23 110.83(15) . . . . ? C5 C8 C23 O23 -71.67(17) . . . . ? N9 C8 C23 O24 -70.83(14) . . . . ? C5 C8 C23 O24 106.67(12) . . . . ? O23 C23 O24 C24 -10.32(19) . . . . ? C8 C23 O24 C24 171.36(11) . . . . ? C23 O24 C24 C25 162.18(12) . . . . ? 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 O6 H6 N9 0.846(14) 1.818(16) 2.5794(14) 149.0(17) . C2 H2A O10 0.99 2.40 3.3484(16) 160.4 2_676 C2 H2B O10 0.99 2.41 2.9880(16) 116.7 1_554 C15 H15 O24 0.95 2.57 3.4797(18) 159.9 2_566 C18 H18 O6 0.95 2.48 3.4300(18) 173.2 2_666 C25 H25A O3 0.98 2.50 3.3779(19) 148.8 2_576 C4 H4 O23 0.95 2.54 3.1421(16) 121.2 . C16 H16 N9 0.95 2.60 3.0151(17) 106.9 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.402 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.047 #============================================================================== data_sb186_hy_compound_10 _database_code_depnum_ccdc_archive 'CCDC 786073' #TrackingRef 'ChemCommun-Gross.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(7-methyl-6-oxo-6,7-dihydro-[1,3]dioxolo[4,5-f]benzofuran-7-yl)- P,P-diphenylphosphinic amide ; _chemical_name_common ; N-(7-methyl-6-oxo-6,7-dihydro-(1,3)dioxolo(4,5-f)benzofuran-7- yl)-P,P-diphenylphosphinic amide ; _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N O5 P' _chemical_formula_sum 'C22 H18 N O5 P' _chemical_formula_weight 407.34 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 5.894(1) _cell_length_b 10.203(2) _cell_length_c 16.399(3) _cell_angle_alpha 97.76(2) _cell_angle_beta 96.88(2) _cell_angle_gamma 99.17(2) _cell_volume 954.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 108 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 70 sec./deg., 2 deg., 7 setsm 343 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18403 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4384 _reflns_number_gt 3199 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. on phenyl group (C18 - C23) is disordered (s.o.f.= 0.534(5). Use of restraint (geometry) and constraints (displacement parameter) for the refinement of the disorder. ; _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^)+(0.0782P)^2^+1.3213P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4384 _refine_ls_number_parameters 259 _refine_ls_number_restraints 82 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1583 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.101 _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 O1 O 0.8888(4) 0.8404(2) 0.54663(15) 0.0367(5) Uani 1 1 d . . . C2 C 0.7543(5) 0.8905(3) 0.4841(2) 0.0371(7) Uani 1 1 d . . . H2A H 0.8265 0.8847 0.4326 0.045 Uiso 1 1 calc R . . H2B H 0.7475 0.9860 0.5029 0.045 Uiso 1 1 calc R . . O3 O 0.5241(4) 0.8122(2) 0.46805(13) 0.0336(5) Uani 1 1 d . . . C3A C 0.5189(5) 0.7256(3) 0.52530(16) 0.0227(5) Uani 1 1 d . . . C4 C 0.3318(4) 0.6319(3) 0.53451(16) 0.0219(5) Uani 1 1 d . . . H4 H 0.1844 0.6185 0.5010 0.026 Uiso 1 1 calc R . . C4A C 0.3814(4) 0.5592(2) 0.59795(16) 0.0203(5) Uani 1 1 d . . . O5 O 0.2207(3) 0.45429(19) 0.61607(12) 0.0232(4) Uani 1 1 d . . . C6 C 0.3270(5) 0.4039(3) 0.68170(19) 0.0282(6) Uani 1 1 d . . . O6 O 0.2328(4) 0.3067(3) 0.70518(16) 0.0439(6) Uani 1 1 d . . . C7 C 0.5720(5) 0.4855(3) 0.71214(16) 0.0239(6) Uani 1 1 d . . . C7A C 0.5921(5) 0.5775(3) 0.64862(16) 0.0220(5) Uani 1 1 d . . . C8A C 0.7363(5) 0.7424(3) 0.57330(18) 0.0255(6) Uani 1 1 d . . . C8 C 0.7822(5) 0.6709(3) 0.63564(18) 0.0252(6) Uani 1 1 d . . . H8 H 0.9311 0.6830 0.6679 0.030 Uiso 1 1 calc R . . C9 C 0.7474(5) 0.3914(3) 0.71389(18) 0.0261(6) Uani 1 1 d . . . H9A H 0.9042 0.4441 0.7308 0.039 Uiso 1 1 calc R . . H9B H 0.7373 0.3395 0.6584 0.039 Uiso 1 1 calc R . . H9C H 0.7137 0.3299 0.7537 0.039 Uiso 1 1 calc R . . N10 N 0.5877(7) 0.5556(3) 0.79789(16) 0.0516(9) Uani 1 1 d D . . H10 H 0.572(8) 0.495(3) 0.829(2) 0.062 Uiso 1 1 d D . . P11 P 0.44163(16) 0.67755(8) 0.82370(5) 0.0346(2) Uani 1 1 d . A . O11 O 0.1921(5) 0.6461(2) 0.79101(16) 0.0491(7) Uani 1 1 d . . . C12 C 0.5806(5) 0.8259(3) 0.78958(18) 0.0308(7) Uani 1 1 d D . . C13 C 0.8149(6) 0.8746(4) 0.8157(2) 0.0540(11) Uani 1 1 d D . . H13 H 0.8999 0.8317 0.8539 0.065 Uiso 1 1 calc R . . C14 C 0.9251(7) 0.9842(5) 0.7869(3) 0.0690(14) Uani 1 1 d D . . H14 H 1.0859 1.0168 0.8050 0.083 Uiso 1 1 calc R . . C15 C 0.8033(7) 1.0467(4) 0.7319(3) 0.0632(14) Uani 1 1 d D . . H15 H 0.8805 1.1220 0.7116 0.076 Uiso 1 1 calc R . . C16 C 0.5689(7) 1.0008(3) 0.7060(3) 0.0544(10) Uani 1 1 d D . . H16 H 0.4847 1.0453 0.6687 0.065 Uiso 1 1 calc R . . C17 C 0.4565(5) 0.8896(3) 0.7346(2) 0.0350(7) Uani 1 1 d D . . H17 H 0.2955 0.8573 0.7165 0.042 Uiso 1 1 calc R . . C18 C 0.5036(6) 0.7074(4) 0.93588(19) 0.0452(9) Uani 1 1 d D . . C19 C 0.6960(11) 0.6733(7) 0.9805(4) 0.0389(11) Uiso 0.534(5) 1 d PD A 1 H19 H 0.8007 0.6292 0.9520 0.047 Uiso 0.534(5) 1 calc PR A 1 C20 C 0.7345(12) 0.7039(8) 1.0666(4) 0.0514(14) Uiso 0.534(5) 1 d PD A 1 H20 H 0.8687 0.6845 1.0975 0.062 Uiso 0.534(5) 1 calc PR A 1 C21 C 0.5721(7) 0.7640(4) 1.1075(2) 0.0573(11) Uani 1 1 d D . . H21 H 0.6080 0.7958 1.1656 0.069 Uiso 0.534(5) 1 calc PR A 1 H21' H 0.5778 0.7755 1.1663 0.069 Uiso 0.466(5) 1 calc PR A 2 C22 C 0.3708(11) 0.7776(8) 1.0677(4) 0.0522(14) Uiso 0.534(5) 1 d PD A 1 H22 H 0.2555 0.8081 1.0975 0.063 Uiso 0.534(5) 1 calc PR A 1 C23 C 0.3306(10) 0.7468(7) 0.9819(3) 0.0431(11) Uiso 0.534(5) 1 d PD A 1 H23 H 0.1834 0.7522 0.9532 0.052 Uiso 0.534(5) 1 calc PR A 1 C19' C 0.6490(13) 0.6442(8) 0.9828(4) 0.0389(11) Uiso 0.466(5) 1 d PD A 2 H19' H 0.7313 0.5821 0.9561 0.047 Uiso 0.466(5) 1 calc PR A 2 C20' C 0.6757(16) 0.6706(8) 1.0687(4) 0.0514(14) Uiso 0.466(5) 1 d PD A 2 H20' H 0.7684 0.6222 1.1006 0.062 Uiso 0.466(5) 1 calc PR A 2 C22' C 0.4534(15) 0.8456(8) 1.0598(4) 0.0522(14) Uiso 0.466(5) 1 d PD A 2 H22' H 0.3891 0.9159 1.0873 0.063 Uiso 0.466(5) 1 calc PR A 2 C23' C 0.4303(13) 0.8237(7) 0.9728(4) 0.0431(11) Uiso 0.466(5) 1 d PD A 2 H23' H 0.3685 0.8837 0.9405 0.052 Uiso 0.466(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0252(11) 0.0294(11) 0.0527(14) 0.0105(10) 0.0045(10) -0.0059(9) C2 0.0327(16) 0.0275(15) 0.050(2) 0.0114(14) 0.0083(14) -0.0039(12) O3 0.0316(11) 0.0325(11) 0.0353(12) 0.0133(9) 0.0041(9) -0.0042(9) C3A 0.0264(13) 0.0204(13) 0.0217(13) 0.0025(10) 0.0055(10) 0.0042(10) C4 0.0195(12) 0.0235(13) 0.0208(13) -0.0007(10) 0.0020(10) 0.0027(10) C4A 0.0194(12) 0.0171(12) 0.0228(13) -0.0029(10) 0.0066(10) 0.0009(9) O5 0.0199(9) 0.0243(10) 0.0264(10) 0.0066(8) 0.0072(7) 0.0021(7) C6 0.0236(13) 0.0340(15) 0.0339(15) 0.0125(12) 0.0139(12) 0.0127(12) O6 0.0247(11) 0.0548(15) 0.0654(16) 0.0390(13) 0.0188(11) 0.0121(10) C7 0.0280(14) 0.0225(13) 0.0215(13) -0.0020(10) 0.0033(10) 0.0104(11) C7A 0.0232(13) 0.0176(12) 0.0231(13) -0.0033(10) 0.0011(10) 0.0050(10) C8A 0.0220(13) 0.0186(12) 0.0338(15) -0.0016(11) 0.0084(11) -0.0009(10) C8 0.0219(13) 0.0178(12) 0.0328(15) -0.0027(11) -0.0006(11) 0.0031(10) C9 0.0235(13) 0.0197(13) 0.0348(15) 0.0007(11) 0.0053(11) 0.0058(10) N10 0.108(3) 0.0380(16) 0.0168(13) 0.0007(11) -0.0001(14) 0.0462(18) P11 0.0592(6) 0.0248(4) 0.0204(4) -0.0044(3) -0.0005(3) 0.0203(4) O11 0.0612(16) 0.0263(12) 0.0465(14) 0.0027(10) -0.0146(12) -0.0122(11) C12 0.0311(15) 0.0313(15) 0.0288(15) -0.0100(12) 0.0054(12) 0.0133(12) C13 0.0271(17) 0.081(3) 0.050(2) -0.010(2) 0.0057(15) 0.0165(18) C14 0.0283(19) 0.072(3) 0.096(4) -0.027(3) 0.024(2) 0.0009(19) C15 0.060(3) 0.0298(18) 0.103(4) -0.009(2) 0.054(3) 0.0029(17) C16 0.067(3) 0.0272(17) 0.078(3) 0.0096(18) 0.027(2) 0.0217(17) C17 0.0359(16) 0.0230(14) 0.0452(19) 0.0002(13) 0.0033(14) 0.0095(12) C18 0.064(2) 0.047(2) 0.0228(15) -0.0075(14) 0.0017(15) 0.0214(17) C21 0.089(3) 0.045(2) 0.0287(18) -0.0077(15) 0.0189(19) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8A 1.387(3) . ? O1 C2 1.420(4) . ? C2 O3 1.435(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O3 C3A 1.373(3) . ? C3A C4 1.377(4) . ? C3A C8A 1.394(4) . ? C4 C4A 1.387(4) . ? C4 H4 0.9500 . ? C4A C7A 1.380(4) . ? C4A O5 1.400(3) . ? O5 C6 1.381(3) . ? C6 O6 1.191(4) . ? C6 C7 1.536(4) . ? C7 N10 1.474(4) . ? C7 C7A 1.496(4) . ? C7 C9 1.519(4) . ? C7A C8 1.407(4) . ? C8A C8 1.360(4) . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N10 P11 1.660(3) . ? N10 H10 0.85(2) . ? P11 O11 1.472(3) . ? P11 C12 1.794(3) . ? P11 C18 1.806(3) . ? C12 C13 1.386(4) . ? C12 C17 1.387(4) . ? C13 C14 1.371(5) . ? C13 H13 0.9500 . ? C14 C15 1.372(5) . ? C14 H14 0.9500 . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 C17 1.387(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19' 1.377(6) . ? C18 C19 1.392(6) . ? C18 C23' 1.412(6) . ? C18 C23 1.416(6) . ? C19 C20 1.388(6) . ? C19 H19 0.9500 . ? C20 C21 1.404(6) . ? C20 H20 0.9500 . ? C21 C22 1.321(6) . ? C21 C20' 1.342(6) . ? C21 C22' 1.423(6) . ? C21 H21 0.9500 . ? C21 H21' 0.9500 . ? C22 C23 1.382(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C19' C20' 1.383(7) . ? C19' H19' 0.9500 . ? C20' H20' 0.9500 . ? C22' C23' 1.400(7) . ? C22' H22' 0.9500 . ? C23' H23' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8A O1 C2 105.8(2) . . ? O1 C2 O3 109.0(2) . . ? O1 C2 H2A 109.9 . . ? O3 C2 H2A 109.9 . . ? O1 C2 H2B 109.9 . . ? O3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C3A O3 C2 105.5(2) . . ? O3 C3A C4 126.5(2) . . ? O3 C3A C8A 110.2(2) . . ? C4 C3A C8A 123.3(3) . . ? C3A C4 C4A 112.8(2) . . ? C3A C4 H4 123.6 . . ? C4A C4 H4 123.6 . . ? C7A C4A C4 125.1(2) . . ? C7A C4A O5 112.1(2) . . ? C4 C4A O5 122.8(2) . . ? C6 O5 C4A 107.5(2) . . ? O6 C6 O5 120.9(3) . . ? O6 C6 C7 128.7(3) . . ? O5 C6 C7 110.4(2) . . ? N10 C7 C7A 114.0(2) . . ? N10 C7 C9 106.8(2) . . ? C7A C7 C9 114.9(2) . . ? N10 C7 C6 110.7(3) . . ? C7A C7 C6 100.7(2) . . ? C9 C7 C6 109.7(2) . . ? C4A C7A C8 120.6(3) . . ? C4A C7A C7 108.9(2) . . ? C8 C7A C7 130.5(2) . . ? C8 C8A O1 127.5(3) . . ? C8 C8A C3A 123.3(3) . . ? O1 C8A C3A 109.2(2) . . ? C8A C8 C7A 114.8(2) . . ? C8A C8 H8 122.6 . . ? C7A C8 H8 122.6 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 N10 P11 123.4(2) . . ? C7 N10 H10 107(3) . . ? P11 N10 H10 112(3) . . ? O11 P11 N10 114.55(17) . . ? O11 P11 C12 111.19(14) . . ? N10 P11 C12 107.48(17) . . ? O11 P11 C18 114.01(17) . . ? N10 P11 C18 102.66(14) . . ? C12 P11 C18 106.23(16) . . ? C13 C12 C17 119.6(3) . . ? C13 C12 P11 120.1(3) . . ? C17 C12 P11 120.2(2) . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.1(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.3(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.0(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 119.5(3) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? C19' C18 C19 15.9(5) . . ? C19' C18 C23' 119.9(5) . . ? C19 C18 C23' 115.0(5) . . ? C19' C18 C23 110.1(5) . . ? C19 C18 C23 116.8(4) . . ? C23' C18 C23 38.9(4) . . ? C19' C18 P11 125.2(3) . . ? C19 C18 P11 123.7(3) . . ? C23' C18 P11 113.6(3) . . ? C23 C18 P11 118.6(3) . . ? C20 C19 C18 119.9(5) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 119.0(5) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20' 115.0(5) . . ? C22 C21 C20 121.9(5) . . ? C20' C21 C20 18.8(6) . . ? C22 C21 C22' 34.4(4) . . ? C20' C21 C22' 119.3(5) . . ? C20 C21 C22' 113.8(5) . . ? C22 C21 H21 119.0 . . ? C20' C21 H21 122.7 . . ? C20 C21 H21 119.0 . . ? C22' C21 H21 115.8 . . ? C22 C21 H21' 113.5 . . ? C20' C21 H21' 120.4 . . ? C20 C21 H21' 122.5 . . ? C22' C21 H21' 120.4 . . ? H21 C21 H21' 15.3 . . ? C21 C22 C23 118.9(5) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? C22 C23 C18 121.6(5) . . ? C22 C23 H23 119.2 . . ? C18 C23 H23 119.2 . . ? C18 C19' C20' 120.3(6) . . ? C18 C19' H19' 119.9 . . ? C20' C19' H19' 119.9 . . ? C21 C20' C19' 120.7(6) . . ? C21 C20' H20' 119.7 . . ? C19' C20' H20' 119.7 . . ? C23' C22' C21 120.9(6) . . ? C23' C22' H22' 119.6 . . ? C21 C22' H22' 119.6 . . ? C22' C23' C18 116.4(5) . . ? C22' C23' H23' 121.8 . . ? C18 C23' H23' 121.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A O1 C2 O3 -5.5(3) . . . . ? O1 C2 O3 C3A 5.0(3) . . . . ? C2 O3 C3A C4 179.1(3) . . . . ? C2 O3 C3A C8A -2.6(3) . . . . ? O3 C3A C4 C4A 179.8(2) . . . . ? C8A C3A C4 C4A 1.7(4) . . . . ? C3A C4 C4A C7A 1.1(4) . . . . ? C3A C4 C4A O5 -177.0(2) . . . . ? C7A C4A O5 C6 1.2(3) . . . . ? C4 C4A O5 C6 179.6(2) . . . . ? C4A O5 C6 O6 -174.3(3) . . . . ? C4A O5 C6 C7 2.9(3) . . . . ? O6 C6 C7 N10 -67.7(4) . . . . ? O5 C6 C7 N10 115.4(2) . . . . ? O6 C6 C7 C7A 171.4(3) . . . . ? O5 C6 C7 C7A -5.5(3) . . . . ? O6 C6 C7 C9 49.9(4) . . . . ? O5 C6 C7 C9 -127.0(2) . . . . ? C4 C4A C7A C8 -3.5(4) . . . . ? O5 C4A C7A C8 174.8(2) . . . . ? C4 C4A C7A C7 176.8(2) . . . . ? O5 C4A C7A C7 -4.9(3) . . . . ? N10 C7 C7A C4A -112.4(3) . . . . ? C9 C7 C7A C4A 123.8(2) . . . . ? C6 C7 C7A C4A 6.1(3) . . . . ? N10 C7 C7A C8 67.8(4) . . . . ? C9 C7 C7A C8 -55.9(4) . . . . ? C6 C7 C7A C8 -173.7(3) . . . . ? C2 O1 C8A C8 -176.2(3) . . . . ? C2 O1 C8A C3A 3.9(3) . . . . ? O3 C3A C8A C8 179.3(3) . . . . ? C4 C3A C8A C8 -2.3(4) . . . . ? O3 C3A C8A O1 -0.8(3) . . . . ? C4 C3A C8A O1 177.6(2) . . . . ? O1 C8A C8 C7A -179.9(2) . . . . ? C3A C8A C8 C7A -0.1(4) . . . . ? C4A C7A C8 C8A 2.8(4) . . . . ? C7 C7A C8 C8A -177.5(3) . . . . ? C7A C7 N10 P11 46.9(4) . . . . ? C9 C7 N10 P11 174.9(3) . . . . ? C6 C7 N10 P11 -65.8(4) . . . . ? C7 N10 P11 O11 49.2(4) . . . . ? C7 N10 P11 C12 -74.9(3) . . . . ? C7 N10 P11 C18 173.3(3) . . . . ? O11 P11 C12 C13 178.1(2) . . . . ? N10 P11 C12 C13 -55.8(3) . . . . ? C18 P11 C12 C13 53.6(3) . . . . ? O11 P11 C12 C17 -4.3(3) . . . . ? N10 P11 C12 C17 121.9(2) . . . . ? C18 P11 C12 C17 -128.8(2) . . . . ? C17 C12 C13 C14 -0.7(5) . . . . ? P11 C12 C13 C14 176.9(3) . . . . ? C12 C13 C14 C15 0.2(6) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C14 C15 C16 C17 -1.0(6) . . . . ? C15 C16 C17 C12 0.5(5) . . . . ? C13 C12 C17 C16 0.4(5) . . . . ? P11 C12 C17 C16 -177.3(2) . . . . ? O11 P11 C18 C19' 127.5(5) . . . . ? N10 P11 C18 C19' 3.0(6) . . . . ? C12 P11 C18 C19' -109.7(6) . . . . ? O11 P11 C18 C19 146.6(5) . . . . ? N10 P11 C18 C19 22.1(5) . . . . ? C12 P11 C18 C19 -90.6(5) . . . . ? O11 P11 C18 C23' -65.7(5) . . . . ? N10 P11 C18 C23' 169.8(4) . . . . ? C12 P11 C18 C23' 57.1(4) . . . . ? O11 P11 C18 C23 -22.5(5) . . . . ? N10 P11 C18 C23 -147.0(4) . . . . ? C12 P11 C18 C23 100.3(4) . . . . ? C19' C18 C19 C20 -81.1(16) . . . . ? C23' C18 C19 C20 30.7(9) . . . . ? C23 C18 C19 C20 -12.8(9) . . . . ? P11 C18 C19 C20 177.9(5) . . . . ? C18 C19 C20 C21 2.7(11) . . . . ? C19 C20 C21 C22 8.3(10) . . . . ? C19 C20 C21 C20' 81.7(15) . . . . ? C19 C20 C21 C22' -29.7(9) . . . . ? C20' C21 C22 C23 -27.9(10) . . . . ? C20 C21 C22 C23 -7.9(11) . . . . ? C22' C21 C22 C23 78.0(9) . . . . ? C21 C22 C23 C18 -3.1(11) . . . . ? C19' C18 C23 C22 29.0(9) . . . . ? C19 C18 C23 C22 13.3(9) . . . . ? C23' C18 C23 C22 -84.0(8) . . . . ? P11 C18 C23 C22 -176.8(6) . . . . ? C19 C18 C19' C20' 93.0(18) . . . . ? C23' C18 C19' C20' 16.8(11) . . . . ? C23 C18 C19' C20' -25.0(10) . . . . ? P11 C18 C19' C20' -177.1(6) . . . . ? C22 C21 C20' C19' 32.1(11) . . . . ? C20 C21 C20' C19' -84.1(16) . . . . ? C22' C21 C20' C19' -6.4(12) . . . . ? C18 C19' C20' C21 -4.1(13) . . . . ? C22 C21 C22' C23' -87.9(10) . . . . ? C20' C21 C22' C23' 4.3(11) . . . . ? C20 C21 C22' C23' 24.4(10) . . . . ? C21 C22' C23' C18 7.8(12) . . . . ? C19' C18 C23' C22' -18.2(10) . . . . ? C19 C18 C23' C22' -35.2(9) . . . . ? C23 C18 C23' C22' 67.2(7) . . . . ? P11 C18 C23' C22' 174.2(6) . . . . ? 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 C8 H8 O11 0.95 2.50 3.359(4) 151.2 1_655 C9 H9A O11 0.98 2.46 3.372(4) 155.3 1_655 C9 H9B O3 0.98 2.58 3.450(4) 147.4 2_666 C15 H15 O6 0.95 2.59 3.475(4) 154.3 1_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.665 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.070 #============================================================================== data_sb185_hy_compound_10-iPrOH _database_code_depnum_ccdc_archive 'CCDC 786074' #TrackingRef 'ChemCommun-Gross.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(7-methyl-6-oxo-6,7-dihydro-[1,3]-dioxolo[4,5-f]benzofuran-7-yl)- P,P'diphenylphosphinic amide ; _chemical_name_common ; N-(7-methyl-6-oxo-6,7-dihydro-(1,3)-dioxolo(4,5-f)benzofuran- 7-yl)-P,P'diphenylphosphinic amide ; _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N O5 P, 0.25 (C3 H8 O)' _chemical_formula_sum 'C22.75 H20 N O5.25 P' _chemical_formula_weight 422.37 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 10.237(1) _cell_length_b 16.524(1) _cell_length_c 23.793(2) _cell_angle_alpha 96.01(1) _cell_angle_beta 100.12(1) _cell_angle_gamma 97.69(1) _cell_volume 3892.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 273 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 100 sec./deg., 1 deg., 5 sets, 709 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66291 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 17770 _reflns_number_gt 11346 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+3.2394P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 17770 _refine_ls_number_parameters 1100 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.020 _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 O1A O 0.15963(19) 0.47870(11) 0.03058(8) 0.0254(4) Uani 1 1 d . . . C2A C 0.1052(3) 0.53508(18) 0.06601(12) 0.0270(6) Uani 1 1 d . . . H2A1 H 0.0140 0.5108 0.0699 0.032 Uiso 1 1 calc R . . H2A2 H 0.0990 0.5866 0.0486 0.032 Uiso 1 1 calc R . . O3A O 0.1930(2) 0.55216(11) 0.12161(8) 0.0267(4) Uani 1 1 d . . . C3AA C 0.2750(3) 0.49272(15) 0.12258(11) 0.0185(6) Uani 1 1 d . . . C4A C 0.3669(3) 0.47869(15) 0.16862(11) 0.0188(6) Uani 1 1 d . . . H4A H 0.3816 0.5097 0.2057 0.023 Uiso 1 1 calc R . . C4AA C 0.4358(3) 0.41480(15) 0.15542(10) 0.0170(5) Uani 1 1 d . . . O5A O 0.53564(18) 0.39053(11) 0.19540(7) 0.0188(4) Uani 1 1 d . . . C6A C 0.5792(3) 0.32368(15) 0.16896(11) 0.0175(5) Uani 1 1 d . . . O6A O 0.67002(19) 0.29418(11) 0.19218(8) 0.0235(4) Uani 1 1 d . . . C7A C 0.5016(3) 0.30194(15) 0.10572(10) 0.0165(5) Uani 1 1 d . . . C7AA C 0.4153(3) 0.36868(15) 0.10186(10) 0.0156(5) Uani 1 1 d . . . C8A C 0.3237(3) 0.38544(15) 0.05541(11) 0.0186(6) Uani 1 1 d . . . H8A H 0.3104 0.3556 0.0180 0.022 Uiso 1 1 calc R . . C8AA C 0.2545(3) 0.44826(15) 0.06794(11) 0.0188(6) Uani 1 1 d . . . C9A C 0.6046(3) 0.30540(16) 0.06673(11) 0.0195(6) Uani 1 1 d . . . H9A1 H 0.6653 0.2655 0.0759 0.029 Uiso 1 1 calc R . . H9A2 H 0.6566 0.3609 0.0727 0.029 Uiso 1 1 calc R . . H9A3 H 0.5584 0.2920 0.0264 0.029 Uiso 1 1 calc R . . N10A N 0.4263(2) 0.21752(13) 0.09480(9) 0.0187(5) Uani 1 1 d D . . H10A H 0.405(3) 0.2003(16) 0.0581(8) 0.022 Uiso 1 1 d D . . P11A P 0.30678(7) 0.19182(4) 0.13178(3) 0.01708(15) Uani 1 1 d . . . O11A O 0.35143(19) 0.22219(11) 0.19378(7) 0.0219(4) Uani 1 1 d . . . C12A C 0.2694(3) 0.08149(16) 0.11631(11) 0.0201(6) Uani 1 1 d . . . C13A C 0.2473(4) 0.03840(18) 0.16168(13) 0.0368(8) Uani 1 1 d . . . H13A H 0.2512 0.0677 0.1986 0.044 Uiso 1 1 calc R . . C14A C 0.2197(4) -0.04643(19) 0.15378(14) 0.0433(9) Uani 1 1 d . . . H14A H 0.2044 -0.0750 0.1852 0.052 Uiso 1 1 calc R . . C15A C 0.2141(3) -0.08972(18) 0.10109(14) 0.0353(8) Uani 1 1 d . . . H15A H 0.1962 -0.1482 0.0959 0.042 Uiso 1 1 calc R . . C16A C 0.2348(4) -0.04808(19) 0.05545(14) 0.0411(8) Uani 1 1 d . . . H16A H 0.2294 -0.0780 0.0186 0.049 Uiso 1 1 calc R . . C17A C 0.2633(3) 0.03720(18) 0.06286(13) 0.0347(8) Uani 1 1 d . . . H17A H 0.2788 0.0654 0.0312 0.042 Uiso 1 1 calc R . . C18A C 0.1576(3) 0.23244(15) 0.10280(11) 0.0180(6) Uani 1 1 d . . . C19A C 0.1067(3) 0.28621(16) 0.13877(11) 0.0226(6) Uani 1 1 d . . . H19A H 0.1458 0.2976 0.1786 0.027 Uiso 1 1 calc R . . C20A C -0.0014(3) 0.32350(18) 0.11670(12) 0.0272(6) Uani 1 1 d . . . H20A H -0.0357 0.3605 0.1416 0.033 Uiso 1 1 calc R . . C21A C -0.0599(3) 0.30748(17) 0.05886(12) 0.0251(6) Uani 1 1 d . . . H21A H -0.1329 0.3340 0.0439 0.030 Uiso 1 1 calc R . . C22A C -0.0113(3) 0.25269(17) 0.02320(12) 0.0252(6) Uani 1 1 d . . . H22A H -0.0521 0.2406 -0.0164 0.030 Uiso 1 1 calc R . . C23A C 0.0966(3) 0.21496(17) 0.04448(11) 0.0235(6) Uani 1 1 d . . . H23A H 0.1293 0.1772 0.0195 0.028 Uiso 1 1 calc R . . O1B O 0.1542(2) 0.44141(12) 0.27675(8) 0.0292(5) Uani 1 1 d . . . C2B C 0.1149(3) 0.50976(19) 0.30677(12) 0.0341(7) Uani 1 1 d . . . H2B1 H 0.0166 0.5002 0.3049 0.041 Uiso 1 1 calc R . . H2B2 H 0.1379 0.5600 0.2890 0.041 Uiso 1 1 calc R . . O3B O 0.1836(2) 0.52042(12) 0.36555(8) 0.0302(5) Uani 1 1 d . . . C3BA C 0.2741(3) 0.46566(16) 0.36790(11) 0.0214(6) Uani 1 1 d . . . C4B C 0.3692(3) 0.45782(15) 0.41462(11) 0.0198(6) Uani 1 1 d . . . H4B H 0.3828 0.4915 0.4507 0.024 Uiso 1 1 calc R . . C4BA C 0.4428(3) 0.39611(15) 0.40372(10) 0.0168(5) Uani 1 1 d . . . O5B O 0.55072(18) 0.38083(11) 0.44415(7) 0.0194(4) Uani 1 1 d . . . C6B C 0.6047(3) 0.31799(16) 0.41908(11) 0.0182(6) Uani 1 1 d . . . O6B O 0.70410(19) 0.29637(11) 0.44294(8) 0.0227(4) Uani 1 1 d . . . C7B C 0.5183(3) 0.28297(15) 0.35922(10) 0.0176(5) Uani 1 1 d . . . C7BA C 0.4222(3) 0.34434(15) 0.35241(10) 0.0179(5) Uani 1 1 d . . . C8B C 0.3287(3) 0.35566(15) 0.30479(11) 0.0184(6) Uani 1 1 d . . . H8B H 0.3165 0.3229 0.2684 0.022 Uiso 1 1 calc R . . C8BA C 0.2561(3) 0.41756(16) 0.31464(11) 0.0204(6) Uani 1 1 d . . . C9B C 0.6051(3) 0.27800(17) 0.31362(11) 0.0223(6) Uani 1 1 d . . . H9B1 H 0.6726 0.2426 0.3241 0.033 Uiso 1 1 calc R . . H9B2 H 0.6501 0.3333 0.3111 0.033 Uiso 1 1 calc R . . H9B3 H 0.5484 0.2549 0.2763 0.033 Uiso 1 1 calc R . . N10B N 0.4507(2) 0.19851(13) 0.36147(9) 0.0196(5) Uani 1 1 d D . . H10B H 0.510(2) 0.1641(15) 0.3619(12) 0.023 Uiso 1 1 d D . . P11B P 0.32546(7) 0.17294(4) 0.39501(3) 0.01692(15) Uani 1 1 d . . . O11B O 0.34628(19) 0.20300(11) 0.45760(7) 0.0215(4) Uani 1 1 d . . . C12B C 0.2986(3) 0.06191(16) 0.37957(11) 0.0199(6) Uani 1 1 d . . . C13B C 0.3305(3) 0.01991(17) 0.33131(11) 0.0244(6) Uani 1 1 d . . . H13B H 0.3696 0.0500 0.3049 0.029 Uiso 1 1 calc R . . C14B C 0.3058(3) -0.06584(18) 0.32132(12) 0.0306(7) Uani 1 1 d . . . H14B H 0.3296 -0.0942 0.2887 0.037 Uiso 1 1 calc R . . C15B C 0.2463(3) -0.10951(18) 0.35924(13) 0.0309(7) Uani 1 1 d . . . H15B H 0.2289 -0.1680 0.3525 0.037 Uiso 1 1 calc R . . C16B C 0.2122(3) -0.06843(18) 0.40692(13) 0.0301(7) Uani 1 1 d . . . H16B H 0.1697 -0.0987 0.4323 0.036 Uiso 1 1 calc R . . C17B C 0.2400(3) 0.01703(17) 0.41777(12) 0.0257(6) Uani 1 1 d . . . H17B H 0.2191 0.0450 0.4512 0.031 Uiso 1 1 calc R . . C18B C 0.1807(3) 0.20661(16) 0.35563(11) 0.0187(6) Uani 1 1 d . . . C19B C 0.1370(3) 0.18069(17) 0.29646(11) 0.0239(6) Uani 1 1 d . . . H19B H 0.1851 0.1453 0.2768 0.029 Uiso 1 1 calc R . . C20B C 0.0252(3) 0.20601(18) 0.26652(12) 0.0276(7) Uani 1 1 d . . . H20B H -0.0031 0.1884 0.2264 0.033 Uiso 1 1 calc R . . C21B C -0.0457(3) 0.25705(18) 0.29494(12) 0.0281(7) Uani 1 1 d . . . H21B H -0.1229 0.2744 0.2742 0.034 Uiso 1 1 calc R . . C22B C -0.0047(3) 0.28297(18) 0.35332(13) 0.0295(7) Uani 1 1 d . . . H22B H -0.0536 0.3182 0.3727 0.035 Uiso 1 1 calc R . . C23B C 0.1084(3) 0.25734(16) 0.38376(12) 0.0232(6) Uani 1 1 d . . . H23B H 0.1360 0.2747 0.4239 0.028 Uiso 1 1 calc R . . O1C O 0.8397(2) 0.52609(12) 0.46957(8) 0.0272(5) Uani 1 1 d . . . C2C C 0.8981(3) 0.47268(18) 0.43336(12) 0.0272(6) Uani 1 1 d . . . H2C1 H 0.9048 0.4201 0.4493 0.033 Uiso 1 1 calc R . . H2C2 H 0.9895 0.4987 0.4309 0.033 Uiso 1 1 calc R . . O3C O 0.8133(2) 0.45790(12) 0.37731(8) 0.0294(5) Uani 1 1 d . . . C3CA C 0.7293(3) 0.51610(16) 0.37731(11) 0.0210(6) Uani 1 1 d . . . C4C C 0.6393(3) 0.53177(15) 0.33116(11) 0.0203(6) Uani 1 1 d . . . H4C H 0.6275 0.5029 0.2935 0.024 Uiso 1 1 calc R . . C4CA C 0.5674(3) 0.59398(15) 0.34509(10) 0.0167(5) Uani 1 1 d . . . O5C O 0.47070(18) 0.62082(11) 0.30501(7) 0.0198(4) Uani 1 1 d . . . C6C C 0.4240(3) 0.68488(15) 0.33273(10) 0.0170(5) Uani 1 1 d . . . O6C O 0.33322(19) 0.71481(11) 0.30907(8) 0.0232(4) Uani 1 1 d . . . C7C C 0.4955(3) 0.70246(15) 0.39657(10) 0.0168(5) Uani 1 1 d . . . C7CA C 0.5835(3) 0.63674(15) 0.39959(10) 0.0161(5) Uani 1 1 d . . . C8C C 0.6732(3) 0.61801(15) 0.44584(11) 0.0180(6) Uani 1 1 d . . . H8C H 0.6835 0.6455 0.4838 0.022 Uiso 1 1 calc R . . C8CA C 0.7450(3) 0.55733(16) 0.43263(11) 0.0194(6) Uani 1 1 d . . . C9C C 0.3888(3) 0.69479(16) 0.43368(11) 0.0217(6) Uani 1 1 d . . . H9C1 H 0.4322 0.7047 0.4744 0.033 Uiso 1 1 calc R . . H9C2 H 0.3366 0.6393 0.4249 0.033 Uiso 1 1 calc R . . H9C3 H 0.3289 0.7355 0.4256 0.033 Uiso 1 1 calc R . . N10C N 0.5686(2) 0.78726(13) 0.41213(9) 0.0180(5) Uani 1 1 d D . . H10C H 0.587(3) 0.7997(16) 0.4495(7) 0.022 Uiso 1 1 d D . . P11C P 0.68847(7) 0.82400(4) 0.37906(3) 0.01816(16) Uani 1 1 d . . . O11C O 0.64508(19) 0.80748(11) 0.31561(8) 0.0234(4) Uani 1 1 d . . . C12C C 0.7214(3) 0.93098(16) 0.40899(12) 0.0244(6) Uani 1 1 d . . . C13C C 0.6196(3) 0.97050(17) 0.42511(12) 0.0267(6) Uani 1 1 d . . . H13C H 0.5341 0.9395 0.4244 0.032 Uiso 1 1 calc R . . C14C C 0.6419(3) 1.05463(18) 0.44214(13) 0.0347(8) Uani 1 1 d . . . H14C H 0.5718 1.0810 0.4534 0.042 Uiso 1 1 calc R . . C15C C 0.7639(4) 1.0998(2) 0.44289(16) 0.0475(10) Uani 1 1 d . . . H15C H 0.7780 1.1577 0.4539 0.057 Uiso 1 1 calc R . . C16C C 0.8674(4) 1.0615(2) 0.42763(18) 0.0510(10) Uani 1 1 d . . . H16C H 0.9524 1.0930 0.4282 0.061 Uiso 1 1 calc R . . C17C C 0.8464(3) 0.97727(18) 0.41167(15) 0.0390(8) Uani 1 1 d . . . H17C H 0.9182 0.9508 0.4024 0.047 Uiso 1 1 calc R . . C18C C 0.8383(3) 0.78025(15) 0.40128(11) 0.0190(6) Uani 1 1 d . . . C19C C 0.8924(3) 0.73605(17) 0.36008(12) 0.0251(6) Uani 1 1 d . . . H19C H 0.8563 0.7344 0.3203 0.030 Uiso 1 1 calc R . . C20C C 0.9982(3) 0.69476(18) 0.37707(13) 0.0294(7) Uani 1 1 d . . . H20C H 1.0358 0.6656 0.3489 0.035 Uiso 1 1 calc R . . C21C C 1.0497(3) 0.69571(17) 0.43504(13) 0.0276(7) Uani 1 1 d . . . H21C H 1.1209 0.6659 0.4466 0.033 Uiso 1 1 calc R . . C22C C 0.9979(3) 0.73979(17) 0.47589(12) 0.0258(6) Uani 1 1 d . . . H22C H 1.0344 0.7411 0.5156 0.031 Uiso 1 1 calc R . . C23C C 0.8930(3) 0.78213(17) 0.45948(11) 0.0227(6) Uani 1 1 d . . . H23C H 0.8580 0.8126 0.4879 0.027 Uiso 1 1 calc R . . O1D O 0.8414(2) 0.56582(12) 0.22405(8) 0.0299(5) Uani 1 1 d . . . C2D C 0.8802(3) 0.49736(18) 0.19365(12) 0.0310(7) Uani 1 1 d . . . H2D1 H 0.8632 0.4479 0.2131 0.037 Uiso 1 1 calc R . . H2D2 H 0.9775 0.5085 0.1932 0.037 Uiso 1 1 calc R . . O3D O 0.8053(2) 0.48295(12) 0.13614(8) 0.0305(5) Uani 1 1 d . . . C3DA C 0.7190(3) 0.53964(16) 0.13338(11) 0.0211(6) Uani 1 1 d . . . C4D C 0.6228(3) 0.54705(15) 0.08664(11) 0.0193(6) Uani 1 1 d . . . H4D H 0.6071 0.5120 0.0510 0.023 Uiso 1 1 calc R . . C4DA C 0.5516(3) 0.61055(15) 0.09680(10) 0.0166(5) Uani 1 1 d . . . O5D O 0.44377(18) 0.62601(10) 0.05679(7) 0.0184(4) Uani 1 1 d . . . C6D C 0.3972(3) 0.69377(16) 0.08004(11) 0.0179(6) Uani 1 1 d . . . O6D O 0.29902(19) 0.71653(11) 0.05622(8) 0.0228(4) Uani 1 1 d . . . C7D C 0.4873(3) 0.72987(15) 0.13895(10) 0.0167(5) Uani 1 1 d . . . C7DA C 0.5762(3) 0.66473(15) 0.14743(10) 0.0167(5) Uani 1 1 d . . . C8D C 0.6711(3) 0.65401(15) 0.19454(11) 0.0187(6) Uani 1 1 d . . . H8D H 0.6867 0.6885 0.2303 0.022 Uiso 1 1 calc R . . C8DA C 0.7402(3) 0.59015(16) 0.18550(11) 0.0193(6) Uani 1 1 d . . . C9D C 0.4009(3) 0.73986(17) 0.18449(11) 0.0215(6) Uani 1 1 d . . . H9D1 H 0.4589 0.7597 0.2221 0.032 Uiso 1 1 calc R . . H9D2 H 0.3476 0.6866 0.1862 0.032 Uiso 1 1 calc R . . H9D3 H 0.3407 0.7797 0.1745 0.032 Uiso 1 1 calc R . . N10D N 0.5588(2) 0.81161(13) 0.13347(9) 0.0177(5) Uani 1 1 d D . . H10D H 0.565(3) 0.8496(14) 0.1632(9) 0.021 Uiso 1 1 d D . . P11D P 0.68255(7) 0.82443(4) 0.09755(3) 0.01685(15) Uani 1 1 d . . . O11D O 0.64811(19) 0.77872(11) 0.03832(7) 0.0230(4) Uani 1 1 d . . . C12D C 0.7187(3) 0.93448(16) 0.10062(11) 0.0220(6) Uani 1 1 d . . . C13D C 0.8494(3) 0.97406(17) 0.10756(12) 0.0277(7) Uani 1 1 d . . . H13D H 0.9210 0.9427 0.1115 0.033 Uiso 1 1 calc R . . C14D C 0.8779(3) 1.05859(19) 0.10895(13) 0.0353(8) Uani 1 1 d . . . H14D H 0.9684 1.0848 0.1143 0.042 Uiso 1 1 calc R . . C15D C 0.7773(4) 1.1035(2) 0.10277(18) 0.0532(10) Uani 1 1 d . . . H15D H 0.7969 1.1616 0.1041 0.064 Uiso 1 1 calc R . . C16D C 0.6465(4) 1.0657(2) 0.0945(2) 0.0814(17) Uani 1 1 d . . . H16D H 0.5757 1.0976 0.0899 0.098 Uiso 1 1 calc R . . C17D C 0.6172(4) 0.9808(2) 0.09282(19) 0.0572(12) Uani 1 1 d . . . H17D H 0.5263 0.9548 0.0862 0.069 Uiso 1 1 calc R . . C18D C 0.8308(3) 0.79541(16) 0.13843(11) 0.0183(6) Uani 1 1 d . . . C19D C 0.8729(3) 0.82797(17) 0.19642(11) 0.0228(6) Uani 1 1 d . . . H19D H 0.8240 0.8655 0.2136 0.027 Uiso 1 1 calc R . . C20D C 0.9849(3) 0.80603(18) 0.22889(12) 0.0267(6) Uani 1 1 d . . . H20D H 1.0131 0.8287 0.2682 0.032 Uiso 1 1 calc R . . C21D C 1.0565(3) 0.75106(18) 0.20441(13) 0.0288(7) Uani 1 1 d . . . H21D H 1.1336 0.7359 0.2268 0.035 Uiso 1 1 calc R . . C22D C 1.0148(3) 0.71837(18) 0.14705(13) 0.0296(7) Uani 1 1 d . . . H22D H 1.0634 0.6805 0.1301 0.035 Uiso 1 1 calc R . . C23D C 0.9021(3) 0.74050(16) 0.11402(12) 0.0237(6) Uani 1 1 d . . . H23D H 0.8741 0.7178 0.0747 0.028 Uiso 1 1 calc R . . O1E O 0.5900(3) 0.92323(13) 0.24152(9) 0.0449(6) Uani 1 1 d DU . . H1E H 0.602(4) 0.890(2) 0.2650(14) 0.067 Uiso 1 1 d D . . C1E C 0.6475(5) 1.0052(2) 0.26740(15) 0.0583(12) Uani 1 1 d DU . . H1E1 H 0.6274 1.0148 0.3070 0.070 Uiso 1 1 calc R . . C2E C 0.7944(5) 1.0218(3) 0.27039(19) 0.0916(18) Uani 1 1 d DU . . H2E1 H 0.8378 0.9830 0.2930 0.137 Uiso 1 1 calc R . . H2E2 H 0.8293 1.0783 0.2888 0.137 Uiso 1 1 calc R . . H2E3 H 0.8136 1.0151 0.2314 0.137 Uiso 1 1 calc R . . C3E C 0.5983(7) 1.0660(3) 0.2338(3) 0.128(2) Uani 1 1 d DU . . H3E1 H 0.5004 1.0600 0.2294 0.192 Uiso 1 1 calc R . . H3E2 H 0.6226 1.0584 0.1958 0.192 Uiso 1 1 calc R . . H3E3 H 0.6385 1.1212 0.2534 0.192 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 O1A 0.0288(12) 0.0269(10) 0.0202(10) 0.0023(8) -0.0017(8) 0.0121(9) C2A 0.0279(17) 0.0273(15) 0.0243(15) 0.0012(12) -0.0022(13) 0.0097(13) O3A 0.0312(12) 0.0255(10) 0.0219(10) -0.0025(8) -0.0021(9) 0.0133(9) C3AA 0.0210(15) 0.0150(13) 0.0196(13) 0.0019(10) 0.0035(11) 0.0038(11) C4A 0.0216(15) 0.0193(13) 0.0144(12) 0.0004(10) 0.0025(11) 0.0015(11) C4AA 0.0188(15) 0.0186(13) 0.0133(12) 0.0033(10) 0.0015(11) 0.0023(11) O5A 0.0225(10) 0.0223(9) 0.0107(8) 0.0022(7) -0.0013(7) 0.0063(8) C6A 0.0194(15) 0.0189(13) 0.0156(12) 0.0040(10) 0.0055(11) 0.0035(11) O6A 0.0228(11) 0.0314(11) 0.0173(9) 0.0068(8) 0.0010(8) 0.0091(9) C7A 0.0171(14) 0.0180(13) 0.0144(12) 0.0016(10) 0.0028(11) 0.0032(10) C7AA 0.0174(14) 0.0165(12) 0.0128(12) 0.0029(10) 0.0031(10) 0.0013(10) C8A 0.0222(15) 0.0187(13) 0.0139(12) 0.0034(10) 0.0024(11) -0.0003(11) C8AA 0.0187(15) 0.0182(13) 0.0175(13) 0.0044(10) -0.0016(11) 0.0012(11) C9A 0.0196(15) 0.0247(14) 0.0152(13) 0.0043(10) 0.0046(11) 0.0036(11) N10A 0.0201(13) 0.0183(11) 0.0172(11) 0.0003(9) 0.0040(10) 0.0028(9) P11A 0.0191(4) 0.0172(3) 0.0152(3) 0.0023(3) 0.0032(3) 0.0041(3) O11A 0.0244(11) 0.0245(10) 0.0162(9) 0.0014(7) 0.0012(8) 0.0056(8) C12A 0.0191(15) 0.0196(13) 0.0210(13) 0.0036(10) 0.0012(11) 0.0036(11) C13A 0.061(2) 0.0274(16) 0.0250(16) 0.0066(12) 0.0132(15) 0.0075(15) C14A 0.067(3) 0.0262(17) 0.0385(19) 0.0156(14) 0.0118(18) 0.0037(16) C15A 0.038(2) 0.0171(14) 0.046(2) 0.0049(13) -0.0047(15) 0.0006(13) C16A 0.054(2) 0.0279(17) 0.0350(18) -0.0086(14) 0.0000(16) 0.0037(16) C17A 0.052(2) 0.0264(16) 0.0245(15) 0.0022(12) 0.0082(15) 0.0028(15) C18A 0.0202(15) 0.0160(13) 0.0182(13) 0.0036(10) 0.0046(11) 0.0017(11) C19A 0.0249(16) 0.0249(14) 0.0182(13) 0.0012(11) 0.0046(12) 0.0054(12) C20A 0.0289(17) 0.0293(16) 0.0261(15) 0.0045(12) 0.0076(13) 0.0106(13) C21A 0.0180(15) 0.0319(16) 0.0281(15) 0.0135(12) 0.0040(12) 0.0064(12) C22A 0.0218(16) 0.0337(16) 0.0186(14) 0.0063(12) 0.0004(12) 0.0010(13) C23A 0.0256(16) 0.0255(15) 0.0188(14) 0.0001(11) 0.0039(12) 0.0047(12) O1B 0.0349(13) 0.0298(11) 0.0204(10) 0.0001(8) -0.0078(9) 0.0163(9) C2B 0.043(2) 0.0339(17) 0.0243(15) -0.0001(13) -0.0043(14) 0.0192(15) O3B 0.0350(13) 0.0315(11) 0.0218(10) -0.0032(8) -0.0069(9) 0.0183(9) C3BA 0.0233(16) 0.0164(13) 0.0238(14) 0.0014(11) 0.0025(12) 0.0041(11) C4B 0.0250(16) 0.0176(13) 0.0158(13) 0.0009(10) 0.0006(11) 0.0048(11) C4BA 0.0172(14) 0.0195(13) 0.0131(12) 0.0067(10) -0.0008(10) 0.0021(11) O5B 0.0226(11) 0.0221(10) 0.0131(9) 0.0027(7) 0.0002(8) 0.0060(8) C6B 0.0197(15) 0.0200(13) 0.0159(13) 0.0064(10) 0.0044(11) 0.0022(11) O6B 0.0224(11) 0.0278(10) 0.0189(9) 0.0060(8) 0.0011(8) 0.0091(8) C7B 0.0189(15) 0.0203(13) 0.0134(12) 0.0037(10) 0.0023(11) 0.0028(11) C7BA 0.0200(15) 0.0183(13) 0.0145(12) 0.0020(10) 0.0024(11) 0.0013(11) C8B 0.0212(15) 0.0192(13) 0.0141(12) 0.0017(10) 0.0022(11) 0.0030(11) C8BA 0.0224(15) 0.0222(14) 0.0152(13) 0.0059(10) -0.0034(11) 0.0047(11) C9B 0.0226(16) 0.0273(15) 0.0184(13) 0.0033(11) 0.0071(11) 0.0044(12) N10B 0.0220(13) 0.0175(11) 0.0210(11) 0.0033(9) 0.0055(10) 0.0072(9) P11B 0.0187(4) 0.0180(3) 0.0140(3) 0.0018(3) 0.0025(3) 0.0037(3) O11B 0.0262(11) 0.0230(10) 0.0143(9) 0.0001(7) 0.0007(8) 0.0055(8) C12B 0.0171(14) 0.0222(14) 0.0191(13) 0.0029(10) -0.0004(11) 0.0038(11) C13B 0.0268(16) 0.0250(15) 0.0214(14) 0.0029(11) 0.0029(12) 0.0062(12) C14B 0.0354(19) 0.0292(16) 0.0243(15) -0.0048(12) -0.0014(13) 0.0109(14) C15B 0.0297(18) 0.0199(14) 0.0374(17) -0.0002(12) -0.0067(14) 0.0042(12) C16B 0.0261(17) 0.0264(15) 0.0364(17) 0.0116(13) 0.0000(14) 0.0015(13) C17B 0.0262(17) 0.0271(15) 0.0226(14) 0.0021(11) 0.0029(12) 0.0029(12) C18B 0.0190(15) 0.0205(13) 0.0172(13) 0.0041(10) 0.0040(11) 0.0031(11) C19B 0.0247(16) 0.0305(15) 0.0173(13) 0.0022(11) 0.0038(12) 0.0083(12) C20B 0.0295(17) 0.0351(17) 0.0162(13) 0.0058(12) -0.0018(12) 0.0044(13) C21B 0.0209(16) 0.0339(17) 0.0304(16) 0.0129(13) 0.0015(13) 0.0049(13) C22B 0.0298(18) 0.0327(16) 0.0297(16) 0.0053(13) 0.0086(13) 0.0127(13) C23B 0.0251(16) 0.0244(14) 0.0211(14) 0.0026(11) 0.0056(12) 0.0059(12) O1C 0.0293(12) 0.0285(11) 0.0220(10) 0.0008(8) -0.0052(9) 0.0138(9) C2C 0.0264(17) 0.0285(15) 0.0248(15) 0.0022(12) -0.0040(13) 0.0103(13) O3C 0.0328(12) 0.0281(11) 0.0264(11) -0.0020(8) -0.0022(9) 0.0162(9) C3CA 0.0246(16) 0.0164(13) 0.0221(14) 0.0000(10) 0.0050(12) 0.0051(11) C4C 0.0248(16) 0.0184(13) 0.0167(13) -0.0013(10) 0.0039(11) 0.0031(11) C4CA 0.0175(14) 0.0189(13) 0.0122(12) 0.0036(10) -0.0005(10) 0.0014(11) O5C 0.0251(11) 0.0214(9) 0.0121(9) 0.0010(7) -0.0009(8) 0.0075(8) C6C 0.0188(15) 0.0175(13) 0.0144(12) 0.0025(10) 0.0037(11) 0.0014(11) O6C 0.0231(11) 0.0291(11) 0.0174(9) 0.0045(8) -0.0005(8) 0.0086(9) C7C 0.0184(14) 0.0193(13) 0.0118(12) 0.0023(10) 0.0021(10) 0.0009(11) C7CA 0.0170(14) 0.0172(13) 0.0141(12) 0.0032(10) 0.0026(10) 0.0016(10) C8C 0.0202(15) 0.0185(13) 0.0134(12) 0.0015(10) 0.0006(11) 0.0001(11) C8CA 0.0195(15) 0.0210(13) 0.0157(13) 0.0042(10) -0.0023(11) 0.0023(11) C9C 0.0228(16) 0.0258(14) 0.0180(13) 0.0041(11) 0.0063(11) 0.0048(12) N10C 0.0208(13) 0.0178(11) 0.0145(11) 0.0011(9) 0.0014(9) 0.0029(9) P11C 0.0196(4) 0.0168(3) 0.0175(3) 0.0026(3) 0.0020(3) 0.0024(3) O11C 0.0251(11) 0.0252(10) 0.0204(10) 0.0069(8) 0.0032(8) 0.0034(8) C12C 0.0276(17) 0.0167(13) 0.0263(15) 0.0028(11) -0.0026(12) 0.0042(12) C13C 0.0291(17) 0.0225(15) 0.0239(15) 0.0009(11) -0.0058(12) 0.0039(12) C14C 0.0360(19) 0.0273(16) 0.0357(18) -0.0042(13) -0.0087(14) 0.0135(14) C15C 0.044(2) 0.0198(16) 0.067(3) -0.0040(16) -0.0145(19) 0.0042(15) C16C 0.036(2) 0.0256(18) 0.083(3) 0.0006(18) -0.002(2) -0.0036(15) C17C 0.0295(19) 0.0243(16) 0.060(2) 0.0025(15) 0.0035(16) 0.0030(14) C18C 0.0179(15) 0.0163(13) 0.0215(13) 0.0017(10) 0.0026(11) 0.0002(11) C19C 0.0258(16) 0.0299(15) 0.0206(14) 0.0025(11) 0.0084(12) 0.0036(12) C20C 0.0274(17) 0.0313(16) 0.0331(17) 0.0010(13) 0.0138(14) 0.0101(13) C21C 0.0168(15) 0.0271(15) 0.0412(18) 0.0077(13) 0.0082(13) 0.0053(12) C22C 0.0193(16) 0.0309(16) 0.0255(15) 0.0058(12) -0.0005(12) 0.0030(12) C23C 0.0198(15) 0.0263(14) 0.0215(14) -0.0004(11) 0.0034(12) 0.0046(12) O1D 0.0355(13) 0.0311(11) 0.0208(10) -0.0011(8) -0.0078(9) 0.0179(9) C2D 0.0359(19) 0.0330(16) 0.0213(15) -0.0008(12) -0.0070(13) 0.0155(14) O3D 0.0366(13) 0.0297(11) 0.0235(11) -0.0037(8) -0.0044(9) 0.0181(9) C3DA 0.0260(16) 0.0174(13) 0.0195(13) 0.0033(10) 0.0026(12) 0.0040(11) C4D 0.0257(16) 0.0164(13) 0.0143(12) 0.0007(10) 0.0022(11) 0.0021(11) C4DA 0.0187(14) 0.0170(13) 0.0136(12) 0.0049(10) 0.0010(11) 0.0016(10) O5D 0.0210(10) 0.0198(9) 0.0132(9) 0.0026(7) -0.0013(8) 0.0048(8) C6D 0.0204(15) 0.0200(13) 0.0146(12) 0.0067(10) 0.0044(11) 0.0035(11) O6D 0.0206(11) 0.0297(11) 0.0180(9) 0.0048(8) -0.0003(8) 0.0081(8) C7D 0.0186(14) 0.0186(13) 0.0116(12) 0.0030(10) 0.0005(10) 0.0004(11) C7DA 0.0183(14) 0.0171(13) 0.0143(12) 0.0033(10) 0.0020(11) 0.0015(10) C8D 0.0229(15) 0.0189(13) 0.0129(12) 0.0014(10) 0.0011(11) 0.0020(11) C8DA 0.0207(15) 0.0204(13) 0.0150(13) 0.0049(10) -0.0021(11) 0.0024(11) C9D 0.0219(15) 0.0266(14) 0.0167(13) 0.0024(11) 0.0055(11) 0.0042(12) N10D 0.0208(13) 0.0159(11) 0.0164(11) 0.0013(8) 0.0030(9) 0.0040(9) P11D 0.0182(4) 0.0187(3) 0.0134(3) 0.0030(3) 0.0021(3) 0.0026(3) O11D 0.0230(11) 0.0301(11) 0.0145(9) 0.0006(8) 0.0028(8) 0.0016(8) C12D 0.0243(16) 0.0237(14) 0.0175(13) 0.0068(11) 0.0007(11) 0.0031(12) C13D 0.0276(17) 0.0279(15) 0.0296(16) 0.0083(12) 0.0076(13) 0.0051(13) C14D 0.0321(19) 0.0316(17) 0.0397(18) 0.0132(14) 0.0029(15) -0.0057(14) C15D 0.046(2) 0.0265(18) 0.092(3) 0.0275(19) 0.015(2) 0.0041(16) C16D 0.037(2) 0.036(2) 0.180(5) 0.046(3) 0.018(3) 0.0167(18) C17D 0.025(2) 0.035(2) 0.114(4) 0.033(2) 0.003(2) 0.0067(15) C18D 0.0169(14) 0.0205(13) 0.0170(13) 0.0042(10) 0.0027(11) -0.0002(11) C19D 0.0236(16) 0.0255(14) 0.0205(14) 0.0038(11) 0.0052(12) 0.0067(12) C20D 0.0221(16) 0.0371(17) 0.0198(14) 0.0069(12) 0.0028(12) -0.0001(13) C21D 0.0193(16) 0.0363(17) 0.0324(16) 0.0158(13) 0.0012(13) 0.0059(13) C22D 0.0253(17) 0.0325(16) 0.0352(17) 0.0084(13) 0.0093(14) 0.0122(13) C23D 0.0251(16) 0.0248(14) 0.0216(14) 0.0013(11) 0.0061(12) 0.0051(12) O1E 0.0848(19) 0.0269(12) 0.0228(11) 0.0054(9) 0.0088(12) 0.0085(12) C1E 0.122(4) 0.0270(18) 0.0341(19) 0.0053(14) 0.037(2) 0.013(2) C2E 0.130(4) 0.066(3) 0.072(3) -0.026(2) 0.063(3) -0.041(3) C3E 0.202(7) 0.100(4) 0.090(4) 0.015(3) 0.031(4) 0.045(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C8AA 1.381(3) . ? O1A C2A 1.424(3) . ? C2A O3A 1.440(3) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? O3A C3AA 1.375(3) . ? C3AA C4A 1.374(4) . ? C3AA C8AA 1.392(3) . ? C4A C4AA 1.385(4) . ? C4A H4A 0.9500 . ? C4AA C7AA 1.382(3) . ? C4AA O5A 1.399(3) . ? O5A C6A 1.379(3) . ? C6A O6A 1.185(3) . ? C6A C7A 1.554(3) . ? C7A N10A 1.474(3) . ? C7A C7AA 1.503(4) . ? C7A C9A 1.521(3) . ? C7AA C8A 1.395(4) . ? C8A C8AA 1.369(4) . ? C8A H8A 0.9500 . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? N10A P11A 1.664(2) . ? N10A H10A 0.870(17) . ? P11A O11A 1.4778(18) . ? P11A C12A 1.797(3) . ? P11A C18A 1.806(3) . ? C12A C17A 1.386(4) . ? C12A C13A 1.388(4) . ? C13A C14A 1.378(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.365(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.377(4) . ? C15A H15A 0.9500 . ? C16A C17A 1.386(4) . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? C18A C19A 1.383(4) . ? C18A C23A 1.401(4) . ? C19A C20A 1.388(4) . ? C19A H19A 0.9500 . ? C20A C21A 1.384(4) . ? C20A H20A 0.9500 . ? C21A C22A 1.377(4) . ? C21A H21A 0.9500 . ? C22A C23A 1.385(4) . ? C22A H22A 0.9500 . ? C23A H23A 0.9500 . ? O1B C8BA 1.382(3) . ? O1B C2B 1.414(3) . ? C2B O3B 1.432(3) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? O3B C3BA 1.377(3) . ? C3BA C4B 1.373(4) . ? C3BA C8BA 1.393(4) . ? C4B C4BA 1.376(4) . ? C4B H4B 0.9500 . ? C4BA C7BA 1.382(3) . ? C4BA O5B 1.401(3) . ? O5B C6B 1.371(3) . ? C6B O6B 1.192(3) . ? C6B C7B 1.547(3) . ? C7B N10B 1.483(3) . ? C7B C7BA 1.506(4) . ? C7B C9B 1.521(3) . ? C7BA C8B 1.395(4) . ? C8B C8BA 1.366(4) . ? C8B H8B 0.9500 . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? N10B P11B 1.656(2) . ? N10B H10B 0.883(17) . ? P11B O11B 1.4883(18) . ? P11B C18B 1.796(3) . ? P11B C12B 1.807(3) . ? C12B C13B 1.391(4) . ? C12B C17B 1.396(4) . ? C13B C14B 1.393(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.385(4) . ? C14B H14B 0.9500 . ? C15B C16B 1.382(4) . ? C15B H15B 0.9500 . ? C16B C17B 1.390(4) . ? C16B H16B 0.9500 . ? C17B H17B 0.9500 . ? C18B C23B 1.386(4) . ? C18B C19B 1.402(4) . ? C19B C20B 1.377(4) . ? C19B H19B 0.9500 . ? C20B C21B 1.383(4) . ? C20B H20B 0.9500 . ? C21B C22B 1.383(4) . ? C21B H21B 0.9500 . ? C22B C23B 1.395(4) . ? C22B H22B 0.9500 . ? C23B H23B 0.9500 . ? O1C C8CA 1.381(3) . ? O1C C2C 1.429(3) . ? C2C O3C 1.435(3) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? O3C C3CA 1.374(3) . ? C3CA C4C 1.374(4) . ? C3CA C8CA 1.389(3) . ? C4C C4CA 1.388(4) . ? C4C H4C 0.9500 . ? C4CA C7CA 1.382(3) . ? C4CA O5C 1.400(3) . ? O5C C6C 1.372(3) . ? C6C O6C 1.193(3) . ? C6C C7C 1.545(3) . ? C7C N10C 1.475(3) . ? C7C C7CA 1.501(4) . ? C7C C9C 1.521(3) . ? C7CA C8C 1.393(4) . ? C8C C8CA 1.363(4) . ? C8C H8C 0.9500 . ? C9C H9C1 0.9800 . ? C9C H9C2 0.9800 . ? C9C H9C3 0.9800 . ? N10C P11C 1.653(2) . ? N10C H10C 0.873(17) . ? P11C O11C 1.4822(19) . ? P11C C12C 1.799(3) . ? P11C C18C 1.802(3) . ? C12C C17C 1.388(4) . ? C12C C13C 1.389(4) . ? C13C C14C 1.383(4) . ? C13C H13C 0.9500 . ? C14C C15C 1.363(5) . ? C14C H14C 0.9500 . ? C15C C16C 1.387(5) . ? C15C H15C 0.9500 . ? C16C C17C 1.381(4) . ? C16C H16C 0.9500 . ? C17C H17C 0.9500 . ? C18C C23C 1.395(4) . ? C18C C19C 1.396(4) . ? C19C C20C 1.379(4) . ? C19C H19C 0.9500 . ? C20C C21C 1.385(4) . ? C20C H20C 0.9500 . ? C21C C22C 1.376(4) . ? C21C H21C 0.9500 . ? C22C C23C 1.380(4) . ? C22C H22C 0.9500 . ? C23C H23C 0.9500 . ? O1D C8DA 1.390(3) . ? O1D C2D 1.418(3) . ? C2D O3D 1.426(3) . ? C2D H2D1 0.9900 . ? C2D H2D2 0.9900 . ? O3D C3DA 1.369(3) . ? C3DA C4D 1.378(4) . ? C3DA C8DA 1.386(3) . ? C4D C4DA 1.380(4) . ? C4D H4D 0.9500 . ? C4DA C7DA 1.387(3) . ? C4DA O5D 1.395(3) . ? O5D C6D 1.376(3) . ? C6D O6D 1.191(3) . ? C6D C7D 1.547(3) . ? C7D N10D 1.478(3) . ? C7D C7DA 1.507(4) . ? C7D C9D 1.524(3) . ? C7DA C8D 1.392(4) . ? C8D C8DA 1.366(4) . ? C8D H8D 0.9500 . ? C9D H9D1 0.9800 . ? C9D H9D2 0.9800 . ? C9D H9D3 0.9800 . ? N10D P11D 1.651(2) . ? N10D H10D 0.882(17) . ? P11D O11D 1.4873(18) . ? P11D C12D 1.798(3) . ? P11D C18D 1.804(3) . ? C12D C17D 1.369(4) . ? C12D C13D 1.383(4) . ? C13D C14D 1.384(4) . ? C13D H13D 0.9500 . ? C14D C15D 1.344(5) . ? C14D H14D 0.9500 . ? C15D C16D 1.371(5) . ? C15D H15D 0.9500 . ? C16D C17D 1.389(5) . ? C16D H16D 0.9500 . ? C17D H17D 0.9500 . ? C18D C23D 1.382(4) . ? C18D C19D 1.397(4) . ? C19D C20D 1.379(4) . ? C19D H19D 0.9500 . ? C20D C21D 1.385(4) . ? C20D H20D 0.9500 . ? C21D C22D 1.384(4) . ? C21D H21D 0.9500 . ? C22D C23D 1.392(4) . ? C22D H22D 0.9500 . ? C23D H23D 0.9500 . ? O1E C1E 1.430(4) . ? O1E H1E 0.829(18) . ? C1E C3E 1.437(5) . ? C1E C2E 1.481(5) . ? C1E H1E1 1.0000 . ? C2E H2E1 0.9800 . ? C2E H2E2 0.9800 . ? C2E H2E3 0.9800 . ? C3E H3E1 0.9800 . ? C3E H3E2 0.9800 . ? C3E H3E3 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 C8AA O1A C2A 105.3(2) . . ? O1A C2A O3A 107.9(2) . . ? O1A C2A H2A1 110.1 . . ? O3A C2A H2A1 110.1 . . ? O1A C2A H2A2 110.1 . . ? O3A C2A H2A2 110.1 . . ? H2A1 C2A H2A2 108.4 . . ? C3AA O3A C2A 105.55(19) . . ? C4A C3AA O3A 127.1(2) . . ? C4A C3AA C8AA 123.6(2) . . ? O3A C3AA C8AA 109.2(2) . . ? C3AA C4A C4AA 113.2(2) . . ? C3AA C4A H4A 123.4 . . ? C4AA C4A H4A 123.4 . . ? C7AA C4AA C4A 124.3(2) . . ? C7AA C4AA O5A 112.6(2) . . ? C4A C4AA O5A 123.1(2) . . ? C6A O5A C4AA 108.05(19) . . ? O6A C6A O5A 121.9(2) . . ? O6A C6A C7A 128.1(2) . . ? O5A C6A C7A 109.8(2) . . ? N10A C7A C7AA 114.6(2) . . ? N10A C7A C9A 107.1(2) . . ? C7AA C7A C9A 114.6(2) . . ? N10A C7A C6A 111.76(19) . . ? C7AA C7A C6A 100.93(19) . . ? C9A C7A C6A 107.7(2) . . ? C4AA C7AA C8A 121.4(2) . . ? C4AA C7AA C7A 108.5(2) . . ? C8A C7AA C7A 130.1(2) . . ? C8AA C8A C7AA 114.8(2) . . ? C8AA C8A H8A 122.6 . . ? C7AA C8A H8A 122.6 . . ? C8A C8AA O1A 127.4(2) . . ? C8A C8AA C3AA 122.6(2) . . ? O1A C8AA C3AA 109.9(2) . . ? C7A C9A H9A1 109.5 . . ? C7A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C7A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C7A N10A P11A 119.69(17) . . ? C7A N10A H10A 111.1(18) . . ? P11A N10A H10A 114.6(18) . . ? O11A P11A N10A 111.45(11) . . ? O11A P11A C12A 113.67(11) . . ? N10A P11A C12A 104.13(12) . . ? O11A P11A C18A 110.46(11) . . ? N10A P11A C18A 109.36(12) . . ? C12A P11A C18A 107.49(12) . . ? C17A C12A C13A 118.5(3) . . ? C17A C12A P11A 124.6(2) . . ? C13A C12A P11A 117.0(2) . . ? C14A C13A C12A 120.8(3) . . ? C14A C13A H13A 119.6 . . ? C12A C13A H13A 119.6 . . ? C15A C14A C13A 120.5(3) . . ? C15A C14A H14A 119.8 . . ? C13A C14A H14A 119.8 . . ? C14A C15A C16A 119.6(3) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C15A C16A C17A 120.5(3) . . ? C15A C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? C12A C17A C16A 120.1(3) . . ? C12A C17A H17A 119.9 . . ? C16A C17A H17A 119.9 . . ? C19A C18A C23A 119.1(3) . . ? C19A C18A P11A 118.7(2) . . ? C23A C18A P11A 122.0(2) . . ? C18A C19A C20A 120.0(3) . . ? C18A C19A H19A 120.0 . . ? C20A C19A H19A 120.0 . . ? C21A C20A C19A 120.8(3) . . ? C21A C20A H20A 119.6 . . ? C19A C20A H20A 119.6 . . ? C22A C21A C20A 119.3(3) . . ? C22A C21A H21A 120.4 . . ? C20A C21A H21A 120.4 . . ? C21A C22A C23A 120.7(3) . . ? C21A C22A H22A 119.7 . . ? C23A C22A H22A 119.7 . . ? C22A C23A C18A 120.0(3) . . ? C22A C23A H23A 120.0 . . ? C18A C23A H23A 120.0 . . ? C8BA O1B C2B 106.2(2) . . ? O1B C2B O3B 108.7(2) . . ? O1B C2B H2B1 109.9 . . ? O3B C2B H2B1 109.9 . . ? O1B C2B H2B2 109.9 . . ? O3B C2B H2B2 109.9 . . ? H2B1 C2B H2B2 108.3 . . ? C3BA O3B C2B 105.6(2) . . ? C4B C3BA O3B 126.8(2) . . ? C4B C3BA C8BA 123.5(3) . . ? O3B C3BA C8BA 109.7(2) . . ? C3BA C4B C4BA 112.9(2) . . ? C3BA C4B H4B 123.5 . . ? C4BA C4B H4B 123.5 . . ? C4B C4BA C7BA 124.8(2) . . ? C4B C4BA O5B 122.5(2) . . ? C7BA C4BA O5B 112.6(2) . . ? C6B O5B C4BA 107.66(19) . . ? O6B C6B O5B 121.5(2) . . ? O6B C6B C7B 128.2(2) . . ? O5B C6B C7B 110.3(2) . . ? N10B C7B C7BA 113.0(2) . . ? N10B C7B C9B 108.0(2) . . ? C7BA C7B C9B 114.8(2) . . ? N10B C7B C6B 109.22(19) . . ? C7BA C7B C6B 100.6(2) . . ? C9B C7B C6B 111.0(2) . . ? C4BA C7BA C8B 121.1(2) . . ? C4BA C7BA C7B 108.2(2) . . ? C8B C7BA C7B 130.7(2) . . ? C8BA C8B C7BA 114.6(2) . . ? C8BA C8B H8B 122.7 . . ? C7BA C8B H8B 122.7 . . ? C8B C8BA O1B 127.9(2) . . ? C8B C8BA C3BA 122.8(3) . . ? O1B C8BA C3BA 109.3(2) . . ? C7B C9B H9B1 109.5 . . ? C7B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C7B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C7B N10B P11B 126.74(17) . . ? C7B N10B H10B 109.4(18) . . ? P11B N10B H10B 115.3(18) . . ? O11B P11B N10B 117.35(11) . . ? O11B P11B C18B 111.21(12) . . ? N10B P11B C18B 106.35(12) . . ? O11B P11B C12B 113.11(11) . . ? N10B P11B C12B 101.52(12) . . ? C18B P11B C12B 106.32(12) . . ? C13B C12B C17B 119.1(2) . . ? C13B C12B P11B 123.3(2) . . ? C17B C12B P11B 117.6(2) . . ? C12B C13B C14B 120.6(3) . . ? C12B C13B H13B 119.7 . . ? C14B C13B H13B 119.7 . . ? C15B C14B C13B 119.6(3) . . ? C15B C14B H14B 120.2 . . ? C13B C14B H14B 120.2 . . ? C16B C15B C14B 120.3(3) . . ? C16B C15B H15B 119.8 . . ? C14B C15B H15B 119.8 . . ? C15B C16B C17B 120.2(3) . . ? C15B C16B H16B 119.9 . . ? C17B C16B H16B 119.9 . . ? C16B C17B C12B 120.1(3) . . ? C16B C17B H17B 119.9 . . ? C12B C17B H17B 119.9 . . ? C23B C18B C19B 118.9(3) . . ? C23B C18B P11B 120.2(2) . . ? C19B C18B P11B 120.8(2) . . ? C20B C19B C18B 120.7(3) . . ? C20B C19B H19B 119.7 . . ? C18B C19B H19B 119.7 . . ? C19B C20B C21B 119.9(3) . . ? C19B C20B H20B 120.0 . . ? C21B C20B H20B 120.0 . . ? C22B C21B C20B 120.3(3) . . ? C22B C21B H21B 119.8 . . ? C20B C21B H21B 119.8 . . ? C21B C22B C23B 119.9(3) . . ? C21B C22B H22B 120.1 . . ? C23B C22B H22B 120.1 . . ? C18B C23B C22B 120.3(3) . . ? C18B C23B H23B 119.9 . . ? C22B C23B H23B 119.9 . . ? C8CA O1C C2C 105.4(2) . . ? O1C C2C O3C 107.8(2) . . ? O1C C2C H2C1 110.1 . . ? O3C C2C H2C1 110.1 . . ? O1C C2C H2C2 110.1 . . ? O3C C2C H2C2 110.1 . . ? H2C1 C2C H2C2 108.5 . . ? C3CA O3C C2C 105.5(2) . . ? O3C C3CA C4C 126.9(2) . . ? O3C C3CA C8CA 109.6(2) . . ? C4C C3CA C8CA 123.4(3) . . ? C3CA C4C C4CA 113.3(2) . . ? C3CA C4C H4C 123.4 . . ? C4CA C4C H4C 123.4 . . ? C7CA C4CA C4C 124.1(2) . . ? C7CA C4CA O5C 112.5(2) . . ? C4C C4CA O5C 123.4(2) . . ? C6C O5C C4CA 107.93(19) . . ? O6C C6C O5C 121.2(2) . . ? O6C C6C C7C 128.4(2) . . ? O5C C6C C7C 110.1(2) . . ? N10C C7C C7CA 114.5(2) . . ? N10C C7C C9C 106.1(2) . . ? C7CA C7C C9C 114.6(2) . . ? N10C C7C C6C 112.43(19) . . ? C7CA C7C C6C 101.1(2) . . ? C9C C7C C6C 108.2(2) . . ? C4CA C7CA C8C 121.2(2) . . ? C4CA C7CA C7C 108.3(2) . . ? C8C C7CA C7C 130.4(2) . . ? C8CA C8C C7CA 115.2(2) . . ? C8CA C8C H8C 122.4 . . ? C7CA C8C H8C 122.4 . . ? C8C C8CA O1C 127.7(2) . . ? C8C C8CA C3CA 122.7(2) . . ? O1C C8CA C3CA 109.6(2) . . ? C7C C9C H9C1 109.5 . . ? C7C C9C H9C2 109.5 . . ? H9C1 C9C H9C2 109.5 . . ? C7C C9C H9C3 109.5 . . ? H9C1 C9C H9C3 109.5 . . ? H9C2 C9C H9C3 109.5 . . ? C7C N10C P11C 122.32(17) . . ? C7C N10C H10C 109.8(18) . . ? P11C N10C H10C 114.4(18) . . ? O11C P11C N10C 111.44(11) . . ? O11C P11C C12C 115.43(12) . . ? N10C P11C C12C 101.69(12) . . ? O11C P11C C18C 110.14(12) . . ? N10C P11C C18C 110.15(12) . . ? C12C P11C C18C 107.62(13) . . ? C17C C12C C13C 118.7(3) . . ? C17C C12C P11C 120.3(2) . . ? C13C C12C P11C 120.8(2) . . ? C14C C13C C12C 120.5(3) . . ? C14C C13C H13C 119.8 . . ? C12C C13C H13C 119.8 . . ? C15C C14C C13C 120.3(3) . . ? C15C C14C H14C 119.9 . . ? C13C C14C H14C 119.9 . . ? C14C C15C C16C 120.2(3) . . ? C14C C15C H15C 119.9 . . ? C16C C15C H15C 119.9 . . ? C17C C16C C15C 119.7(3) . . ? C17C C16C H16C 120.1 . . ? C15C C16C H16C 120.1 . . ? C16C C17C C12C 120.6(3) . . ? C16C C17C H17C 119.7 . . ? C12C C17C H17C 119.7 . . ? C23C C18C C19C 119.1(3) . . ? C23C C18C P11C 121.0(2) . . ? C19C C18C P11C 119.6(2) . . ? C20C C19C C18C 120.1(3) . . ? C20C C19C H19C 120.0 . . ? C18C C19C H19C 120.0 . . ? C19C C20C C21C 120.2(3) . . ? C19C C20C H20C 119.9 . . ? C21C C20C H20C 119.9 . . ? C22C C21C C20C 120.0(3) . . ? C22C C21C H21C 120.0 . . ? C20C C21C H21C 120.0 . . ? C21C C22C C23C 120.4(3) . . ? C21C C22C H22C 119.8 . . ? C23C C22C H22C 119.8 . . ? C22C C23C C18C 120.2(3) . . ? C22C C23C H23C 119.9 . . ? C18C C23C H23C 119.9 . . ? C8DA O1D C2D 105.5(2) . . ? O1D C2D O3D 109.3(2) . . ? O1D C2D H2D1 109.8 . . ? O3D C2D H2D1 109.8 . . ? O1D C2D H2D2 109.8 . . ? O3D C2D H2D2 109.8 . . ? H2D1 C2D H2D2 108.3 . . ? C3DA O3D C2D 105.6(2) . . ? O3D C3DA C4D 126.5(2) . . ? O3D C3DA C8DA 110.3(2) . . ? C4D C3DA C8DA 123.2(3) . . ? C3DA C4D C4DA 113.1(2) . . ? C3DA C4D H4D 123.4 . . ? C4DA C4D H4D 123.4 . . ? C4D C4DA C7DA 124.6(2) . . ? C4D C4DA O5D 122.9(2) . . ? C7DA C4DA O5D 112.5(2) . . ? C6D O5D C4DA 107.94(19) . . ? O6D C6D O5D 121.5(2) . . ? O6D C6D C7D 128.3(2) . . ? O5D C6D C7D 110.1(2) . . ? N10D C7D C7DA 114.4(2) . . ? N10D C7D C9D 109.0(2) . . ? C7DA C7D C9D 114.0(2) . . ? N10D C7D C6D 108.46(19) . . ? C7DA C7D C6D 100.6(2) . . ? C9D C7D C6D 109.9(2) . . ? C4DA C7DA C8D 120.8(2) . . ? C4DA C7DA C7D 108.1(2) . . ? C8D C7DA C7D 131.1(2) . . ? C8DA C8D C7DA 115.0(2) . . ? C8DA C8D H8D 122.5 . . ? C7DA C8D H8D 122.5 . . ? C8D C8DA C3DA 123.1(3) . . ? C8D C8DA O1D 127.7(2) . . ? C3DA C8DA O1D 109.2(2) . . ? C7D C9D H9D1 109.5 . . ? C7D C9D H9D2 109.5 . . ? H9D1 C9D H9D2 109.5 . . ? C7D C9D H9D3 109.5 . . ? H9D1 C9D H9D3 109.5 . . ? H9D2 C9D H9D3 109.5 . . ? C7D N10D P11D 123.26(17) . . ? C7D N10D H10D 114.8(17) . . ? P11D N10D H10D 114.6(18) . . ? O11D P11D N10D 113.02(11) . . ? O11D P11D C12D 114.61(11) . . ? N10D P11D C12D 103.11(12) . . ? O11D P11D C18D 111.21(12) . . ? N10D P11D C18D 109.11(11) . . ? C12D P11D C18D 105.18(12) . . ? C17D C12D C13D 118.2(3) . . ? C17D C12D P11D 120.9(2) . . ? C13D C12D P11D 120.8(2) . . ? C12D C13D C14D 121.2(3) . . ? C12D C13D H13D 119.4 . . ? C14D C13D H13D 119.4 . . ? C15D C14D C13D 120.0(3) . . ? C15D C14D H14D 120.0 . . ? C13D C14D H14D 120.0 . . ? C14D C15D C16D 120.1(3) . . ? C14D C15D H15D 120.0 . . ? C16D C15D H15D 120.0 . . ? C15D C16D C17D 120.3(4) . . ? C15D C16D H16D 119.9 . . ? C17D C16D H16D 119.9 . . ? C12D C17D C16D 120.3(3) . . ? C12D C17D H17D 119.9 . . ? C16D C17D H17D 119.9 . . ? C23D C18D C19D 119.3(3) . . ? C23D C18D P11D 121.5(2) . . ? C19D C18D P11D 119.2(2) . . ? C20D C19D C18D 120.4(3) . . ? C20D C19D H19D 119.8 . . ? C18D C19D H19D 119.8 . . ? C19D C20D C21D 120.3(3) . . ? C19D C20D H20D 119.9 . . ? C21D C20D H20D 119.9 . . ? C22D C21D C20D 119.5(3) . . ? C22D C21D H21D 120.3 . . ? C20D C21D H21D 120.3 . . ? C21D C22D C23D 120.5(3) . . ? C21D C22D H22D 119.8 . . ? C23D C22D H22D 119.8 . . ? C18D C23D C22D 120.0(3) . . ? C18D C23D H23D 120.0 . . ? C22D C23D H23D 120.0 . . ? C1E O1E H1E 111(3) . . ? O1E C1E C3E 112.0(4) . . ? O1E C1E C2E 112.5(3) . . ? C3E C1E C2E 103.3(4) . . ? O1E C1E H1E1 109.6 . . ? C3E C1E H1E1 109.6 . . ? C2E C1E H1E1 109.6 . . ? C1E C2E H2E1 109.5 . . ? C1E C2E H2E2 109.5 . . ? H2E1 C2E H2E2 109.5 . . ? C1E C2E H2E3 109.5 . . ? H2E1 C2E H2E3 109.5 . . ? H2E2 C2E H2E3 109.5 . . ? C1E C3E H3E1 109.5 . . ? C1E C3E H3E2 109.5 . . ? H3E1 C3E H3E2 109.5 . . ? C1E C3E H3E3 109.5 . . ? H3E1 C3E H3E3 109.5 . . ? H3E2 C3E H3E3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8AA O1A C2A O3A 14.4(3) . . . . ? O1A C2A O3A C3AA -14.2(3) . . . . ? C2A O3A C3AA C4A -173.3(3) . . . . ? C2A O3A C3AA C8AA 8.4(3) . . . . ? O3A C3AA C4A C4AA -179.0(2) . . . . ? C8AA C3AA C4A C4AA -0.9(4) . . . . ? C3AA C4A C4AA C7AA -0.4(4) . . . . ? C3AA C4A C4AA O5A 178.9(2) . . . . ? C7AA C4AA O5A C6A -2.9(3) . . . . ? C4A C4AA O5A C6A 177.6(2) . . . . ? C4AA O5A C6A O6A 175.0(2) . . . . ? C4AA O5A C6A C7A 0.2(3) . . . . ? O6A C6A C7A N10A 65.6(3) . . . . ? O5A C6A C7A N10A -120.0(2) . . . . ? O6A C6A C7A C7AA -172.2(3) . . . . ? O5A C6A C7A C7AA 2.2(2) . . . . ? O6A C6A C7A C9A -51.8(3) . . . . ? O5A C6A C7A C9A 122.6(2) . . . . ? C4A C4AA C7AA C8A 2.0(4) . . . . ? O5A C4AA C7AA C8A -177.4(2) . . . . ? C4A C4AA C7AA C7A -176.1(2) . . . . ? O5A C4AA C7AA C7A 4.4(3) . . . . ? N10A C7A C7AA C4AA 116.4(2) . . . . ? C9A C7A C7AA C4AA -119.2(2) . . . . ? C6A C7A C7AA C4AA -3.8(2) . . . . ? N10A C7A C7AA C8A -61.6(3) . . . . ? C9A C7A C7AA C8A 62.8(3) . . . . ? C6A C7A C7AA C8A 178.2(2) . . . . ? C4AA C7AA C8A C8AA -2.1(4) . . . . ? C7A C7AA C8A C8AA 175.6(2) . . . . ? C7AA C8A C8AA O1A 179.1(2) . . . . ? C7AA C8A C8AA C3AA 0.8(4) . . . . ? C2A O1A C8AA C8A 172.2(3) . . . . ? C2A O1A C8AA C3AA -9.4(3) . . . . ? C4A C3AA C8AA C8A 0.7(4) . . . . ? O3A C3AA C8AA C8A 179.1(2) . . . . ? C4A C3AA C8AA O1A -177.8(2) . . . . ? O3A C3AA C8AA O1A 0.6(3) . . . . ? C7AA C7A N10A P11A -53.0(3) . . . . ? C9A C7A N10A P11A 178.68(18) . . . . ? C6A C7A N10A P11A 61.0(3) . . . . ? C7A N10A P11A O11A -45.1(2) . . . . ? C7A N10A P11A C12A -168.04(19) . . . . ? C7A N10A P11A C18A 77.3(2) . . . . ? O11A P11A C12A C17A -160.7(3) . . . . ? N10A P11A C12A C17A -39.2(3) . . . . ? C18A P11A C12A C17A 76.7(3) . . . . ? O11A P11A C12A C13A 18.3(3) . . . . ? N10A P11A C12A C13A 139.8(2) . . . . ? C18A P11A C12A C13A -104.2(3) . . . . ? C17A C12A C13A C14A -0.1(5) . . . . ? P11A C12A C13A C14A -179.2(3) . . . . ? C12A C13A C14A C15A 0.3(6) . . . . ? C13A C14A C15A C16A -0.8(6) . . . . ? C14A C15A C16A C17A 1.1(5) . . . . ? C13A C12A C17A C16A 0.5(5) . . . . ? P11A C12A C17A C16A 179.4(3) . . . . ? C15A C16A C17A C12A -1.0(5) . . . . ? O11A P11A C18A C19A 2.0(2) . . . . ? N10A P11A C18A C19A -121.1(2) . . . . ? C12A P11A C18A C19A 126.5(2) . . . . ? O11A P11A C18A C23A 178.2(2) . . . . ? N10A P11A C18A C23A 55.2(2) . . . . ? C12A P11A C18A C23A -57.3(2) . . . . ? C23A C18A C19A C20A -1.4(4) . . . . ? P11A C18A C19A C20A 174.9(2) . . . . ? C18A C19A C20A C21A 0.2(4) . . . . ? C19A C20A C21A C22A 1.2(4) . . . . ? C20A C21A C22A C23A -1.2(4) . . . . ? C21A C22A C23A C18A -0.1(4) . . . . ? C19A C18A C23A C22A 1.4(4) . . . . ? P11A C18A C23A C22A -174.8(2) . . . . ? C8BA O1B C2B O3B -6.9(3) . . . . ? O1B C2B O3B C3BA 7.3(3) . . . . ? C2B O3B C3BA C4B 174.9(3) . . . . ? C2B O3B C3BA C8BA -4.9(3) . . . . ? O3B C3BA C4B C4BA 178.7(2) . . . . ? C8BA C3BA C4B C4BA -1.5(4) . . . . ? C3BA C4B C4BA C7BA -2.4(4) . . . . ? C3BA C4B C4BA O5B 175.9(2) . . . . ? C4B C4BA O5B C6B -177.7(2) . . . . ? C7BA C4BA O5B C6B 0.7(3) . . . . ? C4BA O5B C6B O6B 174.9(2) . . . . ? C4BA O5B C6B C7B -5.7(2) . . . . ? O6B C6B C7B N10B 68.3(3) . . . . ? O5B C6B C7B N10B -111.1(2) . . . . ? O6B C6B C7B C7BA -172.7(3) . . . . ? O5B C6B C7B C7BA 7.9(2) . . . . ? O6B C6B C7B C9B -50.8(3) . . . . ? O5B C6B C7B C9B 129.8(2) . . . . ? C4B C4BA C7BA C8B 5.2(4) . . . . ? O5B C4BA C7BA C8B -173.2(2) . . . . ? C4B C4BA C7BA C7B -177.0(2) . . . . ? O5B C4BA C7BA C7B 4.6(3) . . . . ? N10B C7B C7BA C4BA 109.1(2) . . . . ? C9B C7B C7BA C4BA -126.4(2) . . . . ? C6B C7B C7BA C4BA -7.2(2) . . . . ? N10B C7B C7BA C8B -73.5(3) . . . . ? C9B C7B C7BA C8B 51.1(4) . . . . ? C6B C7B C7BA C8B 170.2(3) . . . . ? C4BA C7BA C8B C8BA -3.8(4) . . . . ? C7B C7BA C8B C8BA 179.0(3) . . . . ? C7BA C8B C8BA O1B -177.7(2) . . . . ? C7BA C8B C8BA C3BA 0.1(4) . . . . ? C2B O1B C8BA C8B -178.0(3) . . . . ? C2B O1B C8BA C3BA 3.9(3) . . . . ? C4B C3BA C8BA C8B 2.7(4) . . . . ? O3B C3BA C8BA C8B -177.5(2) . . . . ? C4B C3BA C8BA O1B -179.2(2) . . . . ? O3B C3BA C8BA O1B 0.7(3) . . . . ? C7BA C7B N10B P11B -39.8(3) . . . . ? C9B C7B N10B P11B -167.93(19) . . . . ? C6B C7B N10B P11B 71.2(3) . . . . ? C7B N10B P11B O11B -55.6(3) . . . . ? C7B N10B P11B C18B 69.6(2) . . . . ? C7B N10B P11B C12B -179.4(2) . . . . ? O11B P11B C12B C13B -152.9(2) . . . . ? N10B P11B C12B C13B -26.2(3) . . . . ? C18B P11B C12B C13B 84.8(3) . . . . ? O11B P11B C12B C17B 28.6(3) . . . . ? N10B P11B C12B C17B 155.2(2) . . . . ? C18B P11B C12B C17B -93.7(2) . . . . ? C17B C12B C13B C14B -0.6(4) . . . . ? P11B C12B C13B C14B -179.2(2) . . . . ? C12B C13B C14B C15B 1.3(4) . . . . ? C13B C14B C15B C16B -0.3(5) . . . . ? C14B C15B C16B C17B -1.3(5) . . . . ? C15B C16B C17B C12B 2.0(4) . . . . ? C13B C12B C17B C16B -1.1(4) . . . . ? P11B C12B C17B C16B 177.6(2) . . . . ? O11B P11B C18B C23B 2.8(3) . . . . ? N10B P11B C18B C23B -126.0(2) . . . . ? C12B P11B C18B C23B 126.4(2) . . . . ? O11B P11B C18B C19B -175.7(2) . . . . ? N10B P11B C18B C19B 55.5(2) . . . . ? C12B P11B C18B C19B -52.1(2) . . . . ? C23B C18B C19B C20B 0.9(4) . . . . ? P11B C18B C19B C20B 179.4(2) . . . . ? C18B C19B C20B C21B -0.5(4) . . . . ? C19B C20B C21B C22B 0.1(4) . . . . ? C20B C21B C22B C23B -0.2(4) . . . . ? C19B C18B C23B C22B -0.9(4) . . . . ? P11B C18B C23B C22B -179.5(2) . . . . ? C21B C22B C23B C18B 0.6(4) . . . . ? C8CA O1C C2C O3C -14.2(3) . . . . ? O1C C2C O3C C3CA 14.2(3) . . . . ? C2C O3C C3CA C4C 173.0(3) . . . . ? C2C O3C C3CA C8CA -8.6(3) . . . . ? O3C C3CA C4C C4CA 179.3(2) . . . . ? C8CA C3CA C4C C4CA 1.1(4) . . . . ? C3CA C4C C4CA C7CA 0.2(4) . . . . ? C3CA C4C C4CA O5C 179.7(2) . . . . ? C7CA C4CA O5C C6C 2.1(3) . . . . ? C4C C4CA O5C C6C -177.5(2) . . . . ? C4CA O5C C6C O6C -174.3(2) . . . . ? C4CA O5C C6C C7C 0.1(3) . . . . ? O6C C6C C7C N10C -65.5(3) . . . . ? O5C C6C C7C N10C 120.6(2) . . . . ? O6C C6C C7C C7CA 172.0(3) . . . . ? O5C C6C C7C C7CA -1.9(2) . . . . ? O6C C6C C7C C9C 51.2(3) . . . . ? O5C C6C C7C C9C -122.6(2) . . . . ? C4C C4CA C7CA C8C -1.8(4) . . . . ? O5C C4CA C7CA C8C 178.6(2) . . . . ? C4C C4CA C7CA C7C 176.2(2) . . . . ? O5C C4CA C7CA C7C -3.3(3) . . . . ? N10C C7C C7CA C4CA -118.0(2) . . . . ? C9C C7C C7CA C4CA 119.1(2) . . . . ? C6C C7C C7CA C4CA 3.0(2) . . . . ? N10C C7C C7CA C8C 59.7(3) . . . . ? C9C C7C C7CA C8C -63.2(4) . . . . ? C6C C7C C7CA C8C -179.2(2) . . . . ? C4CA C7CA C8C C8CA 2.0(4) . . . . ? C7C C7CA C8C C8CA -175.5(2) . . . . ? C7CA C8C C8CA O1C -179.7(2) . . . . ? C7CA C8C C8CA C3CA -0.8(4) . . . . ? C2C O1C C8CA C8C -172.0(3) . . . . ? C2C O1C C8CA C3CA 9.0(3) . . . . ? O3C C3CA C8CA C8C -179.2(2) . . . . ? C4C C3CA C8CA C8C -0.8(4) . . . . ? O3C C3CA C8CA O1C -0.2(3) . . . . ? C4C C3CA C8CA O1C 178.2(2) . . . . ? C7CA C7C N10C P11C 56.3(3) . . . . ? C9C C7C N10C P11C -176.30(18) . . . . ? C6C C7C N10C P11C -58.3(3) . . . . ? C7C N10C P11C O11C 48.9(2) . . . . ? C7C N10C P11C C12C 172.4(2) . . . . ? C7C N10C P11C C18C -73.7(2) . . . . ? O11C P11C C12C C17C -85.3(3) . . . . ? N10C P11C C12C C17C 153.9(2) . . . . ? C18C P11C C12C C17C 38.1(3) . . . . ? O11C P11C C12C C13C 89.0(2) . . . . ? N10C P11C C12C C13C -31.7(3) . . . . ? C18C P11C C12C C13C -147.5(2) . . . . ? C17C C12C C13C C14C 1.5(4) . . . . ? P11C C12C C13C C14C -172.9(2) . . . . ? C12C C13C C14C C15C 0.5(5) . . . . ? C13C C14C C15C C16C -1.2(5) . . . . ? C14C C15C C16C C17C 0.0(6) . . . . ? C15C C16C C17C C12C 2.1(6) . . . . ? C13C C12C C17C C16C -2.8(5) . . . . ? P11C C12C C17C C16C 171.7(3) . . . . ? O11C P11C C18C C23C -175.0(2) . . . . ? N10C P11C C18C C23C -51.7(2) . . . . ? C12C P11C C18C C23C 58.4(2) . . . . ? O11C P11C C18C C19C -2.0(2) . . . . ? N10C P11C C18C C19C 121.3(2) . . . . ? C12C P11C C18C C19C -128.6(2) . . . . ? C23C C18C C19C C20C 0.2(4) . . . . ? P11C C18C C19C C20C -172.9(2) . . . . ? C18C C19C C20C C21C 1.1(4) . . . . ? C19C C20C C21C C22C -1.8(4) . . . . ? C20C C21C C22C C23C 1.0(4) . . . . ? C21C C22C C23C C18C 0.3(4) . . . . ? C19C C18C C23C C22C -0.9(4) . . . . ? P11C C18C C23C C22C 172.1(2) . . . . ? C8DA O1D C2D O3D 2.2(3) . . . . ? O1D C2D O3D C3DA -2.7(3) . . . . ? C2D O3D C3DA C4D -177.3(3) . . . . ? C2D O3D C3DA C8DA 2.1(3) . . . . ? O3D C3DA C4D C4DA -179.7(2) . . . . ? C8DA C3DA C4D C4DA 1.0(4) . . . . ? C3DA C4D C4DA C7DA 2.9(4) . . . . ? C3DA C4D C4DA O5D -175.8(2) . . . . ? C4D C4DA O5D C6D -179.1(2) . . . . ? C7DA C4DA O5D C6D 2.0(3) . . . . ? C4DA O5D C6D O6D -174.5(2) . . . . ? C4DA O5D C6D C7D 3.9(2) . . . . ? O6D C6D C7D N10D -68.9(3) . . . . ? O5D C6D C7D N10D 112.8(2) . . . . ? O6D C6D C7D C7DA 170.7(3) . . . . ? O5D C6D C7D C7DA -7.6(2) . . . . ? O6D C6D C7D C9D 50.2(3) . . . . ? O5D C6D C7D C9D -128.1(2) . . . . ? C4D C4DA C7DA C8D -5.2(4) . . . . ? O5D C4DA C7DA C8D 173.6(2) . . . . ? C4D C4DA C7DA C7D 174.0(2) . . . . ? O5D C4DA C7DA C7D -7.2(3) . . . . ? N10D C7D C7DA C4DA -107.5(2) . . . . ? C9D C7D C7DA C4DA 126.1(2) . . . . ? C6D C7D C7DA C4DA 8.5(2) . . . . ? N10D C7D C7DA C8D 71.6(3) . . . . ? C9D C7D C7DA C8D -54.8(4) . . . . ? C6D C7D C7DA C8D -172.4(3) . . . . ? C4DA C7DA C8D C8DA 3.2(4) . . . . ? C7D C7DA C8D C8DA -175.8(2) . . . . ? C7DA C8D C8DA C3DA 0.4(4) . . . . ? C7DA C8D C8DA O1D 178.9(2) . . . . ? O3D C3DA C8DA C8D 177.9(2) . . . . ? C4D C3DA C8DA C8D -2.7(4) . . . . ? O3D C3DA C8DA O1D -0.9(3) . . . . ? C4D C3DA C8DA O1D 178.6(2) . . . . ? C2D O1D C8DA C8D -179.5(3) . . . . ? C2D O1D C8DA C3DA -0.8(3) . . . . ? C7DA C7D N10D P11D 39.4(3) . . . . ? C9D C7D N10D P11D 168.36(18) . . . . ? C6D C7D N10D P11D -72.0(3) . . . . ? C7D N10D P11D O11D 50.9(2) . . . . ? C7D N10D P11D C12D 175.2(2) . . . . ? C7D N10D P11D C18D -73.4(2) . . . . ? O11D P11D C12D C17D 81.1(3) . . . . ? N10D P11D C12D C17D -42.1(3) . . . . ? C18D P11D C12D C17D -156.4(3) . . . . ? O11D P11D C12D C13D -95.1(2) . . . . ? N10D P11D C12D C13D 141.7(2) . . . . ? C18D P11D C12D C13D 27.4(2) . . . . ? C17D C12D C13D C14D 2.6(4) . . . . ? P11D C12D C13D C14D 178.8(2) . . . . ? C12D C13D C14D C15D -0.8(5) . . . . ? C13D C14D C15D C16D -0.7(6) . . . . ? C14D C15D C16D C17D 0.4(7) . . . . ? C13D C12D C17D C16D -2.8(6) . . . . ? P11D C12D C17D C16D -179.1(4) . . . . ? C15D C16D C17D C12D 1.4(8) . . . . ? O11D P11D C18D C23D 3.1(2) . . . . ? N10D P11D C18D C23D 128.4(2) . . . . ? C12D P11D C18D C23D -121.5(2) . . . . ? O11D P11D C18D C19D -175.62(19) . . . . ? N10D P11D C18D C19D -50.3(2) . . . . ? C12D P11D C18D C19D 59.8(2) . . . . ? C23D C18D C19D C20D 0.5(4) . . . . ? P11D C18D C19D C20D 179.2(2) . . . . ? C18D C19D C20D C21D -0.4(4) . . . . ? C19D C20D C21D C22D 0.1(4) . . . . ? C20D C21D C22D C23D 0.2(4) . . . . ? C19D C18D C23D C22D -0.2(4) . . . . ? P11D C18D C23D C22D -178.9(2) . . . . ? C21D C22D C23D C18D -0.1(4) . . . . ? 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 O1E H1E O11C 0.829(18) 1.955(19) 2.780(3) 174(4) . N10A H10A O11D 0.870(17) 2.34(2) 3.134(3) 153(2) 2_665 N10C H10C O11B 0.873(17) 2.202(18) 3.050(3) 164(3) 2_666 N10D H10D O1E 0.882(17) 2.072(18) 2.945(3) 170(3) . C9A H9A2 O3D 0.98 2.53 3.425(3) 152.1 . C9A H9A3 O5D 0.98 2.51 3.241(3) 131.1 2_665 C9A H9A3 O11D 0.98 2.45 3.303(3) 144.7 2_665 C8A H8A O11D 0.95 2.59 3.403(3) 143.3 2_665 C8B H8B O11A 0.95 2.41 3.321(3) 160.0 . C9B H9B3 O11A 0.98 2.51 3.454(3) 161.3 . C9C H9C1 O5B 0.98 2.51 3.276(3) 134.8 2_666 C9C H9C2 O3B 0.98 2.47 3.398(3) 157.0 . C15B H15B O6C 0.95 2.55 3.314(4) 138.1 1_545 C15C H15C O6B 0.95 2.53 3.385(4) 149.5 1_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.496 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.069 #============================================================================== data_sb159_hy_compound_11 _database_code_depnum_ccdc_archive 'CCDC 786075' #TrackingRef 'ChemCommun-Gross.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(5-(allyloxy)-6-hydroxy-3-methyl-2-oxo-2,3-dihydrobenzofuran-3-yl)- P,P-diphenylphosphinic amide ; _chemical_name_common ; N-(5-(allyloxy)-6-hydroxy-3-methyl-2-oxo-2,3- dihydrobenzofuran-3-yl)-P,P-diphenylphosphinic amide ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 N O5 P' _chemical_formula_sum 'C24 H22 N O5 P' _chemical_formula_weight 435.40 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 10.509(1) _cell_length_b 13.334(1) _cell_length_c 16.224(1) _cell_angle_alpha 83.82(1) _cell_angle_beta 79.60(1) _cell_angle_gamma 75.14(1) _cell_volume 2156.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10937 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 140 sec./deg., 2 deg., 6 sets, 256 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29641 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9843 _reflns_number_gt 6830 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One allyloxy group is disordered. ; _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^)+(0.1253P)^2^+1.1758P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9843 _refine_ls_number_parameters 568 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2100 _refine_ls_wR_factor_gt 0.1846 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.7181(2) 0.50161(16) 0.49587(12) 0.0211(5) Uani 1 1 d . . . C2 C 0.6536(3) 0.4252(2) 0.52728(18) 0.0195(6) Uani 1 1 d . . . O2 O 0.6031(2) 0.38480(17) 0.48408(13) 0.0265(5) Uani 1 1 d . . . C3 C 0.6581(3) 0.4027(2) 0.62304(17) 0.0180(6) Uani 1 1 d . . . N3 N 0.7007(2) 0.29042(19) 0.64391(15) 0.0185(5) Uani 1 1 d D . . H3 H 0.638(3) 0.259(2) 0.656(2) 0.022 Uiso 1 1 d D . . P3 P 0.85503(7) 0.22029(6) 0.61517(4) 0.01630(18) Uani 1 1 d . . . O3 O 0.9327(2) 0.27804(16) 0.55024(13) 0.0219(5) Uani 1 1 d . . . C3A C 0.7547(3) 0.4645(2) 0.63420(18) 0.0183(6) Uani 1 1 d . . . C4 C 0.8188(3) 0.4710(2) 0.69978(17) 0.0172(6) Uani 1 1 d . . . H4 H 0.8033 0.4322 0.7516 0.021 Uiso 1 1 calc R . . C5 C 0.9062(3) 0.5351(2) 0.68868(17) 0.0176(6) Uani 1 1 d . . . O5 O 0.9708(2) 0.54329(16) 0.75426(12) 0.0204(4) Uani 1 1 d D A . C6 C 0.9289(3) 0.5941(2) 0.61248(18) 0.0183(6) Uani 1 1 d . . . O6 O 1.0156(2) 0.65521(17) 0.60782(13) 0.0229(5) Uani 1 1 d D . . H6 H 1.030(4) 0.679(3) 0.5579(14) 0.034 Uiso 1 1 d D . . C7 C 0.8658(3) 0.5870(2) 0.54594(18) 0.0198(6) Uani 1 1 d . . . H7 H 0.8807 0.6255 0.4938 0.024 Uiso 1 1 calc R . . C7A C 0.7805(3) 0.5217(2) 0.55884(17) 0.0193(6) Uani 1 1 d . . . C8 C 1.1079(3) 0.4837(3) 0.7435(2) 0.0312(8) Uani 1 1 d D . . H8A H 1.1555 0.5042 0.6884 0.037 Uiso 0.784(7) 1 calc PR A 1 H8B H 1.1110 0.4088 0.7446 0.037 Uiso 0.784(7) 1 calc PR A 1 H8C H 1.1635 0.5203 0.7011 0.037 Uiso 0.216(7) 1 calc PR A 2 H8D H 1.1143 0.4147 0.7236 0.037 Uiso 0.216(7) 1 calc PR A 2 C9 C 1.1743(5) 0.5024(4) 0.8114(3) 0.0348(11) Uiso 0.784(7) 1 d PD A 1 H9 H 1.1825 0.5710 0.8153 0.042 Uiso 0.784(7) 1 calc PR A 1 C10 C 1.2224(6) 0.4302(4) 0.8662(3) 0.0535(14) Uiso 0.784(7) 1 d PD A 1 H10A H 1.2158 0.3609 0.8640 0.064 Uiso 0.784(7) 1 calc PR A 1 H10B H 1.2640 0.4470 0.9085 0.064 Uiso 0.784(7) 1 calc PR A 1 C9A C 1.1567(14) 0.4710(13) 0.8257(7) 0.0348(11) Uiso 0.216(7) 1 d PD A 2 H9A H 1.1271 0.4223 0.8670 0.042 Uiso 0.216(7) 1 calc PR A 2 C10A C 1.2371(19) 0.5218(16) 0.8453(12) 0.0535(14) Uiso 0.216(7) 1 d PD A 2 H10C H 1.2688 0.5712 0.8057 0.064 Uiso 0.216(7) 1 calc PR A 2 H10D H 1.2637 0.5093 0.8992 0.064 Uiso 0.216(7) 1 calc PR A 2 C11 C 0.5167(3) 0.4454(2) 0.67052(19) 0.0236(6) Uani 1 1 d . . . H11A H 0.4579 0.4027 0.6613 0.035 Uiso 1 1 calc R . . H11B H 0.4824 0.5173 0.6497 0.035 Uiso 1 1 calc R . . H11C H 0.5199 0.4434 0.7307 0.035 Uiso 1 1 calc R . . C12 C 0.9368(3) 0.1822(2) 0.70605(17) 0.0177(6) Uani 1 1 d . . . C13 C 0.8762(3) 0.1373(3) 0.77921(19) 0.0248(7) Uani 1 1 d . . . H13 H 0.7887 0.1281 0.7824 0.030 Uiso 1 1 calc R . . C14 C 0.9433(3) 0.1059(3) 0.84737(19) 0.0289(7) Uani 1 1 d . . . H14 H 0.9015 0.0754 0.8971 0.035 Uiso 1 1 calc R . . C15 C 1.0703(4) 0.1186(3) 0.8433(2) 0.0299(7) Uani 1 1 d . . . H15 H 1.1159 0.0964 0.8900 0.036 Uiso 1 1 calc R . . C16 C 1.1320(3) 0.1637(3) 0.7712(2) 0.0300(7) Uani 1 1 d . . . H16 H 1.2193 0.1730 0.7688 0.036 Uiso 1 1 calc R . . C17 C 1.0653(3) 0.1955(3) 0.7023(2) 0.0252(7) Uani 1 1 d . . . H17 H 1.1075 0.2261 0.6528 0.030 Uiso 1 1 calc R . . C18 C 0.8334(3) 0.1042(2) 0.57812(17) 0.0182(6) Uani 1 1 d . . . C19 C 0.8912(3) 0.0044(2) 0.60950(18) 0.0204(6) Uani 1 1 d . . . H19 H 0.9377 -0.0044 0.6559 0.025 Uiso 1 1 calc R . . C20 C 0.8808(3) -0.0822(2) 0.57295(19) 0.0240(7) Uani 1 1 d . . . H20 H 0.9203 -0.1500 0.5944 0.029 Uiso 1 1 calc R . . C21 C 0.8134(3) -0.0701(3) 0.5057(2) 0.0257(7) Uani 1 1 d . . . H21 H 0.8058 -0.1295 0.4812 0.031 Uiso 1 1 calc R . . C22 C 0.7564(3) 0.0295(3) 0.47364(19) 0.0259(7) Uani 1 1 d . . . H22 H 0.7111 0.0378 0.4267 0.031 Uiso 1 1 calc R . . C23 C 0.7653(3) 0.1157(2) 0.50963(18) 0.0215(6) Uani 1 1 d . . . H23 H 0.7253 0.1833 0.4880 0.026 Uiso 1 1 calc R . . O1' O 0.7622(2) 0.90877(16) 0.97844(12) 0.0227(5) Uani 1 1 d . . . C2' C 0.8365(3) 0.8157(2) 0.9473(2) 0.0248(7) Uani 1 1 d . . . O2' O 0.9074(3) 0.75243(19) 0.98717(15) 0.0367(6) Uani 1 1 d . . . C3' C 0.8173(3) 0.8110(2) 0.85503(18) 0.0201(6) Uani 1 1 d . . . N3' N 0.7780(3) 0.7166(2) 0.84394(15) 0.0199(5) Uani 1 1 d D . . H3' H 0.843(3) 0.666(2) 0.828(2) 0.024 Uiso 1 1 d D . . P3' P 0.63528(7) 0.69539(6) 0.89363(4) 0.01779(19) Uani 1 1 d . . . O3' O 0.5899(2) 0.74773(16) 0.97435(12) 0.0228(5) Uani 1 1 d . . . C3A' C 0.7117(3) 0.9107(2) 0.84503(17) 0.0181(6) Uani 1 1 d . . . C4' C 0.6446(3) 0.9568(2) 0.77872(17) 0.0176(6) Uani 1 1 d . . . H4' H 0.6599 0.9223 0.7283 0.021 Uiso 1 1 calc R . . C5' C 0.5555(3) 1.0530(2) 0.78664(17) 0.0188(6) Uani 1 1 d . . . O5' O 0.4886(2) 1.10942(17) 0.72447(13) 0.0248(5) Uani 1 1 d D . . C6' C 0.5293(3) 1.1038(2) 0.86305(18) 0.0198(6) Uani 1 1 d . . . O6' O 0.4382(2) 1.19665(17) 0.86673(13) 0.0259(5) Uani 1 1 d D . . H6' H 0.432(4) 1.216(3) 0.9151(15) 0.039 Uiso 1 1 d D . . C7' C 0.5969(3) 1.0578(2) 0.92928(17) 0.0197(6) Uani 1 1 d . . . H7' H 0.5811 1.0904 0.9807 0.024 Uiso 1 1 calc R . . C7A' C 0.6873(3) 0.9635(2) 0.91752(17) 0.0193(6) Uani 1 1 d . . . C8' C 0.4961(3) 1.0579(2) 0.65134(18) 0.0227(6) Uani 1 1 d D . . H8'1 H 0.4461 1.0031 0.6646 0.027 Uiso 1 1 calc R . . H8'2 H 0.5902 1.0247 0.6299 0.027 Uiso 1 1 calc R . . C9' C 0.4377(3) 1.1359(3) 0.5863(2) 0.0269(7) Uani 1 1 d D . . H9' H 0.4421 1.1119 0.5325 0.032 Uiso 1 1 calc R . . C10' C 0.3811(3) 1.2342(3) 0.5969(2) 0.0336(8) Uani 1 1 d D . . H10E H 0.3745 1.2616 0.6496 0.040 Uiso 1 1 calc R . . H10F H 0.3467 1.2782 0.5519 0.040 Uiso 1 1 calc R . . C11' C 0.9511(3) 0.8102(3) 0.7980(2) 0.0269(7) Uani 1 1 d . . . H11D H 1.0148 0.7437 0.8076 0.040 Uiso 1 1 calc R . . H11E H 0.9860 0.8671 0.8110 0.040 Uiso 1 1 calc R . . H11F H 0.9380 0.8191 0.7392 0.040 Uiso 1 1 calc R . . C12' C 0.5109(3) 0.7423(2) 0.82524(18) 0.0201(6) Uani 1 1 d . . . C13' C 0.5393(3) 0.7170(3) 0.74129(19) 0.0271(7) Uani 1 1 d . . . H13' H 0.6256 0.6781 0.7189 0.033 Uiso 1 1 calc R . . C14' C 0.4402(4) 0.7492(3) 0.6909(2) 0.0332(8) Uani 1 1 d . . . H14' H 0.4583 0.7315 0.6341 0.040 Uiso 1 1 calc R . . C15' C 0.3154(4) 0.8071(3) 0.7237(2) 0.0381(9) Uani 1 1 d . . . H15' H 0.2478 0.8282 0.6893 0.046 Uiso 1 1 calc R . . C16' C 0.2878(4) 0.8344(3) 0.8058(3) 0.0403(9) Uani 1 1 d . . . H16' H 0.2026 0.8757 0.8273 0.048 Uiso 1 1 calc R . . C17' C 0.3855(3) 0.8011(3) 0.8567(2) 0.0298(7) Uani 1 1 d . . . H17' H 0.3663 0.8186 0.9136 0.036 Uiso 1 1 calc R . . C18' C 0.6664(3) 0.5558(2) 0.90303(17) 0.0196(6) Uani 1 1 d . . . C19' C 0.7843(3) 0.4952(2) 0.92760(18) 0.0253(7) Uani 1 1 d . . . H19' H 0.8509 0.5275 0.9365 0.030 Uiso 1 1 calc R . . C20' C 0.8050(4) 0.3878(3) 0.9391(2) 0.0338(8) Uani 1 1 d . . . H20' H 0.8853 0.3466 0.9559 0.041 Uiso 1 1 calc R . . C21' C 0.7068(4) 0.3414(3) 0.9257(2) 0.0342(8) Uani 1 1 d . . . H21' H 0.7208 0.2680 0.9332 0.041 Uiso 1 1 calc R . . C22' C 0.5878(4) 0.4010(3) 0.9014(2) 0.0299(7) Uani 1 1 d . . . H22' H 0.5213 0.3683 0.8929 0.036 Uiso 1 1 calc R . . C23' C 0.5673(3) 0.5084(2) 0.88969(19) 0.0243(7) Uani 1 1 d . . . H23' H 0.4870 0.5495 0.8728 0.029 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 O1 0.0253(11) 0.0251(11) 0.0151(10) 0.0041(8) -0.0077(9) -0.0088(9) C2 0.0178(14) 0.0205(14) 0.0209(15) 0.0010(11) -0.0069(12) -0.0042(11) O2 0.0310(12) 0.0295(12) 0.0232(11) -0.0008(9) -0.0126(10) -0.0095(10) C3 0.0187(14) 0.0224(15) 0.0132(13) 0.0008(11) -0.0047(11) -0.0048(12) N3 0.0158(12) 0.0204(13) 0.0209(12) 0.0051(10) -0.0058(10) -0.0080(10) P3 0.0177(4) 0.0197(4) 0.0127(3) 0.0023(3) -0.0028(3) -0.0077(3) O3 0.0242(11) 0.0238(11) 0.0194(10) 0.0044(8) -0.0007(9) -0.0130(9) C3A 0.0183(14) 0.0188(14) 0.0172(14) 0.0016(11) -0.0022(11) -0.0051(11) C4 0.0197(14) 0.0203(14) 0.0114(13) 0.0006(10) -0.0027(11) -0.0051(11) C5 0.0205(14) 0.0221(14) 0.0102(12) -0.0009(10) -0.0053(11) -0.0035(12) O5 0.0207(10) 0.0281(11) 0.0136(10) -0.0017(8) -0.0051(8) -0.0062(9) C6 0.0172(14) 0.0183(14) 0.0194(14) 0.0012(11) -0.0023(11) -0.0060(11) O6 0.0270(11) 0.0264(11) 0.0180(10) 0.0037(8) -0.0043(9) -0.0131(9) C7 0.0224(15) 0.0209(14) 0.0147(13) 0.0044(11) -0.0012(11) -0.0060(12) C7A 0.0213(15) 0.0221(15) 0.0143(13) 0.0008(11) -0.0061(11) -0.0033(12) C8 0.0249(17) 0.040(2) 0.0273(17) -0.0048(14) -0.0099(14) 0.0004(15) C11 0.0207(15) 0.0279(16) 0.0217(15) -0.0010(12) -0.0007(12) -0.0072(13) C12 0.0192(14) 0.0199(14) 0.0140(13) -0.0006(11) -0.0042(11) -0.0041(11) C13 0.0245(16) 0.0334(17) 0.0196(15) 0.0016(12) -0.0050(13) -0.0131(14) C14 0.0363(19) 0.0361(18) 0.0167(15) 0.0047(13) -0.0072(14) -0.0139(15) C15 0.0353(18) 0.0361(19) 0.0197(15) 0.0009(13) -0.0126(14) -0.0065(15) C16 0.0244(16) 0.044(2) 0.0262(17) -0.0033(14) -0.0089(14) -0.0127(15) C17 0.0231(15) 0.0348(18) 0.0199(15) -0.0004(13) -0.0045(13) -0.0106(13) C18 0.0210(14) 0.0218(15) 0.0134(13) -0.0006(11) -0.0004(11) -0.0098(12) C19 0.0205(14) 0.0257(15) 0.0148(13) 0.0024(11) -0.0024(12) -0.0069(12) C20 0.0249(16) 0.0253(16) 0.0203(15) -0.0016(12) 0.0007(12) -0.0066(13) C21 0.0260(16) 0.0291(17) 0.0242(16) -0.0062(13) 0.0009(13) -0.0121(13) C22 0.0253(16) 0.0363(18) 0.0193(15) -0.0021(13) -0.0059(13) -0.0118(14) C23 0.0204(14) 0.0280(16) 0.0176(14) 0.0014(12) -0.0058(12) -0.0079(12) O1' 0.0296(11) 0.0254(11) 0.0158(10) 0.0002(8) -0.0112(9) -0.0067(9) C2' 0.0272(16) 0.0273(16) 0.0230(15) -0.0018(12) -0.0106(13) -0.0074(13) O2' 0.0432(15) 0.0359(14) 0.0310(13) -0.0023(10) -0.0217(11) 0.0011(11) C3' 0.0206(14) 0.0258(15) 0.0155(14) 0.0009(11) -0.0047(12) -0.0080(12) N3' 0.0204(13) 0.0198(12) 0.0190(12) -0.0030(10) -0.0015(10) -0.0045(10) P3' 0.0202(4) 0.0207(4) 0.0132(4) 0.0002(3) -0.0027(3) -0.0067(3) O3' 0.0248(11) 0.0270(11) 0.0153(10) -0.0027(8) 0.0004(9) -0.0058(9) C3A' 0.0178(14) 0.0220(14) 0.0155(13) 0.0006(11) -0.0020(11) -0.0078(11) C4' 0.0187(14) 0.0239(15) 0.0102(12) -0.0016(10) -0.0017(11) -0.0055(12) C5' 0.0188(14) 0.0247(15) 0.0144(13) 0.0026(11) -0.0054(11) -0.0074(12) O5' 0.0319(12) 0.0246(11) 0.0167(10) 0.0003(8) -0.0112(9) -0.0004(9) C6' 0.0204(14) 0.0205(14) 0.0183(14) 0.0005(11) -0.0004(12) -0.0073(12) O6' 0.0311(12) 0.0259(12) 0.0173(11) -0.0025(9) -0.0027(10) -0.0013(10) C7' 0.0238(15) 0.0235(15) 0.0129(13) -0.0015(11) -0.0005(11) -0.0091(12) C7A' 0.0211(14) 0.0268(15) 0.0134(13) 0.0033(11) -0.0069(11) -0.0108(12) C8' 0.0269(16) 0.0263(16) 0.0166(14) 0.0007(12) -0.0063(12) -0.0084(13) C9' 0.0234(16) 0.0395(19) 0.0212(15) 0.0073(13) -0.0104(13) -0.0128(14) C10' 0.0253(17) 0.039(2) 0.038(2) 0.0145(15) -0.0134(15) -0.0128(15) C11' 0.0200(15) 0.0294(17) 0.0306(17) 0.0010(13) -0.0014(13) -0.0077(13) C12' 0.0239(15) 0.0190(14) 0.0202(14) 0.0017(11) -0.0080(12) -0.0085(12) C13' 0.0331(18) 0.0280(17) 0.0209(15) 0.0017(12) -0.0093(14) -0.0065(14) C14' 0.044(2) 0.038(2) 0.0226(16) 0.0029(14) -0.0152(15) -0.0139(16) C15' 0.035(2) 0.047(2) 0.038(2) 0.0120(17) -0.0211(17) -0.0149(17) C16' 0.0228(17) 0.049(2) 0.047(2) 0.0014(18) -0.0106(16) -0.0038(16) C17' 0.0214(16) 0.0365(19) 0.0311(18) -0.0026(14) -0.0050(14) -0.0054(14) C18' 0.0298(16) 0.0191(14) 0.0091(12) 0.0017(10) 0.0006(12) -0.0083(12) C19' 0.0289(17) 0.0293(17) 0.0161(14) 0.0034(12) -0.0053(13) -0.0048(13) C20' 0.042(2) 0.0316(18) 0.0221(16) 0.0066(13) -0.0071(15) -0.0003(15) C21' 0.054(2) 0.0211(16) 0.0232(16) 0.0026(13) 0.0013(16) -0.0088(16) C22' 0.0399(19) 0.0316(18) 0.0208(16) 0.0017(13) 0.0008(14) -0.0186(15) C23' 0.0297(17) 0.0261(16) 0.0166(14) 0.0008(12) 0.0001(13) -0.0095(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 O1 C2 1.370(3) . ? O1 C7A 1.391(3) . ? C2 O2 1.194(4) . ? C2 C3 1.557(4) . ? C3 N3 1.469(4) . ? C3 C3A 1.507(4) . ? C3 C11 1.541(4) . ? N3 P3 1.663(3) . ? N3 H3 0.849(18) . ? P3 O3 1.485(2) . ? P3 C18 1.800(3) . ? P3 C12 1.801(3) . ? C3A C4 1.379(4) . ? C3A C7A 1.391(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 O5 1.389(3) . ? C5 C6 1.409(4) . ? O5 C8 1.446(4) . ? C6 O6 1.357(3) . ? C6 C7 1.388(4) . ? O6 H6 0.841(18) . ? C7 C7A 1.378(4) . ? C7 H7 0.9500 . ? C8 C9 1.479(5) . ? C8 C9A 1.491(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 C10 1.304(6) . ? C9 H9 0.9500 . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C9A C10A 1.308(9) . ? C9A H9A 0.9500 . ? C10A H10C 0.9500 . ? C10A H10D 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.394(4) . ? C12 C17 1.397(4) . ? C13 C14 1.388(4) . ? C13 H13 0.9500 . ? C14 C15 1.377(5) . ? C14 H14 0.9500 . ? C15 C16 1.387(5) . ? C15 H15 0.9500 . ? C16 C17 1.396(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.397(4) . ? C18 C23 1.401(4) . ? C19 C20 1.390(4) . ? C19 H19 0.9500 . ? C20 C21 1.378(4) . ? C20 H20 0.9500 . ? C21 C22 1.397(5) . ? C21 H21 0.9500 . ? C22 C23 1.375(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? O1' C2' 1.379(4) . ? O1' C7A' 1.400(3) . ? C2' O2' 1.192(4) . ? C2' C3' 1.555(4) . ? C3' N3' 1.460(4) . ? C3' C3A' 1.512(4) . ? C3' C11' 1.535(4) . ? N3' P3' 1.647(3) . ? N3' H3' 0.854(18) . ? P3' O3' 1.493(2) . ? P3' C18' 1.800(3) . ? P3' C12' 1.813(3) . ? C3A' C7A' 1.386(4) . ? C3A' C4' 1.394(4) . ? C4' C5' 1.383(4) . ? C4' H4' 0.9500 . ? C5' O5' 1.378(3) . ? C5' C6' 1.427(4) . ? O5' C8' 1.414(4) . ? C6' O6' 1.356(4) . ? C6' C7' 1.395(4) . ? O6' H6' 0.836(19) . ? C7' C7A' 1.376(4) . ? C7' H7' 0.9500 . ? C8' C9' 1.498(4) . ? C8' H8'1 0.9900 . ? C8' H8'2 0.9900 . ? C9' C10' 1.309(5) . ? C9' H9' 0.9500 . ? C10' H10E 0.9500 . ? C10' H10F 0.9500 . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? C12' C17' 1.387(4) . ? C12' C13' 1.400(4) . ? C13' C14' 1.393(5) . ? C13' H13' 0.9500 . ? C14' C15' 1.385(5) . ? C14' H14' 0.9500 . ? C15' C16' 1.379(6) . ? C15' H15' 0.9500 . ? C16' C17' 1.388(5) . ? C16' H16' 0.9500 . ? C17' H17' 0.9500 . ? C18' C19' 1.394(4) . ? C18' C23' 1.407(4) . ? C19' C20' 1.389(5) . ? C19' H19' 0.9500 . ? C20' C21' 1.390(5) . ? C20' H20' 0.9500 . ? C21' C22' 1.397(5) . ? C21' H21' 0.9500 . ? C22' C23' 1.389(5) . ? C22' H22' 0.9500 . ? C23' H23' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C7A 107.6(2) . . ? O2 C2 O1 122.1(3) . . ? O2 C2 C3 127.9(3) . . ? O1 C2 C3 110.1(2) . . ? N3 C3 C3A 115.1(2) . . ? N3 C3 C11 109.4(2) . . ? C3A C3 C11 112.6(2) . . ? N3 C3 C2 110.8(2) . . ? C3A C3 C2 100.6(2) . . ? C11 C3 C2 107.9(2) . . ? C3 N3 P3 123.25(19) . . ? C3 N3 H3 115(2) . . ? P3 N3 H3 119(2) . . ? O3 P3 N3 111.61(12) . . ? O3 P3 C18 112.73(13) . . ? N3 P3 C18 104.52(13) . . ? O3 P3 C12 110.73(13) . . ? N3 P3 C12 109.51(13) . . ? C18 P3 C12 107.48(13) . . ? C4 C3A C7A 119.2(3) . . ? C4 C3A C3 133.3(3) . . ? C7A C3A C3 107.5(3) . . ? C3A C4 C5 118.8(2) . . ? C3A C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 O5 119.6(2) . . ? C4 C5 C6 121.2(3) . . ? O5 C5 C6 119.2(3) . . ? C5 O5 C8 112.6(2) . . ? O6 C6 C7 122.9(2) . . ? O6 C6 C5 116.9(3) . . ? C7 C6 C5 120.2(3) . . ? C6 O6 H6 108(3) . . ? C7A C7 C6 117.0(3) . . ? C7A C7 H7 121.5 . . ? C6 C7 H7 121.5 . . ? C7 C7A C3A 123.5(3) . . ? C7 C7A O1 123.0(2) . . ? C3A C7A O1 113.3(3) . . ? O5 C8 C9 110.0(3) . . ? O5 C8 C9A 108.8(6) . . ? C9 C8 C9A 20.0(6) . . ? O5 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C9A C8 H8A 126.4 . . ? O5 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? C9A C8 H8B 92.2 . . ? H8A C8 H8B 108.2 . . ? O5 C8 H8C 109.9 . . ? C9 C8 H8C 91.4 . . ? C9A C8 H8C 109.9 . . ? H8A C8 H8C 20.2 . . ? H8B C8 H8C 124.4 . . ? O5 C8 H8D 109.9 . . ? C9 C8 H8D 125.1 . . ? C9A C8 H8D 109.9 . . ? H8A C8 H8D 90.2 . . ? H8B C8 H8D 19.7 . . ? H8C C8 H8D 108.3 . . ? C10 C9 C8 123.9(5) . . ? C10 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C10A C9A C8 125.0(13) . . ? C10A C9A H9A 117.5 . . ? C8 C9A H9A 117.5 . . ? C9A C10A H10C 120.0 . . ? C9A C10A H10D 120.0 . . ? H10C C10A H10D 120.0 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 119.2(3) . . ? C13 C12 P3 121.5(2) . . ? C17 C12 P3 119.2(2) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.2(3) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C19 C18 C23 119.2(3) . . ? C19 C18 P3 122.9(2) . . ? C23 C18 P3 117.6(2) . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 119.9(3) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 120.2(3) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? C2' O1' C7A' 108.1(2) . . ? O2' C2' O1' 122.3(3) . . ? O2' C2' C3' 127.5(3) . . ? O1' C2' C3' 110.2(2) . . ? N3' C3' C3A' 114.8(2) . . ? N3' C3' C11' 108.3(2) . . ? C3A' C3' C11' 113.7(2) . . ? N3' C3' C2' 111.3(2) . . ? C3A' C3' C2' 100.4(2) . . ? C11' C3' C2' 108.1(3) . . ? C3' N3' P3' 120.7(2) . . ? C3' N3' H3' 114(2) . . ? P3' N3' H3' 120(2) . . ? O3' P3' N3' 112.39(13) . . ? O3' P3' C18' 115.47(12) . . ? N3' P3' C18' 103.47(13) . . ? O3' P3' C12' 109.68(14) . . ? N3' P3' C12' 108.40(13) . . ? C18' P3' C12' 107.00(14) . . ? C7A' C3A' C4' 118.5(3) . . ? C7A' C3A' C3' 108.6(2) . . ? C4' C3A' C3' 132.8(3) . . ? C5' C4' C3A' 119.8(3) . . ? C5' C4' H4' 120.1 . . ? C3A' C4' H4' 120.1 . . ? O5' C5' C4' 125.5(3) . . ? O5' C5' C6' 114.1(3) . . ? C4' C5' C6' 120.4(3) . . ? C5' O5' C8' 116.8(2) . . ? O6' C6' C7' 123.3(3) . . ? O6' C6' C5' 116.9(3) . . ? C7' C6' C5' 119.8(3) . . ? C6' O6' H6' 106(3) . . ? C7A' C7' C6' 117.6(3) . . ? C7A' C7' H7' 121.2 . . ? C6' C7' H7' 121.2 . . ? C7' C7A' C3A' 123.8(3) . . ? C7' C7A' O1' 123.7(3) . . ? C3A' C7A' O1' 112.4(3) . . ? O5' C8' C9' 108.8(3) . . ? O5' C8' H8'1 109.9 . . ? C9' C8' H8'1 109.9 . . ? O5' C8' H8'2 109.9 . . ? C9' C8' H8'2 109.9 . . ? H8'1 C8' H8'2 108.3 . . ? C10' C9' C8' 125.8(3) . . ? C10' C9' H9' 117.1 . . ? C8' C9' H9' 117.1 . . ? C9' C10' H10E 120.0 . . ? C9' C10' H10F 120.0 . . ? H10E C10' H10F 120.0 . . ? C3' C11' H11D 109.5 . . ? C3' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C3' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C17' C12' C13' 119.7(3) . . ? C17' C12' P3' 120.0(2) . . ? C13' C12' P3' 120.3(2) . . ? C14' C13' C12' 119.5(3) . . ? C14' C13' H13' 120.3 . . ? C12' C13' H13' 120.3 . . ? C15' C14' C13' 119.9(3) . . ? C15' C14' H14' 120.1 . . ? C13' C14' H14' 120.1 . . ? C16' C15' C14' 120.9(3) . . ? C16' C15' H15' 119.6 . . ? C14' C15' H15' 119.6 . . ? C15' C16' C17' 119.5(3) . . ? C15' C16' H16' 120.3 . . ? C17' C16' H16' 120.3 . . ? C12' C17' C16' 120.6(3) . . ? C12' C17' H17' 119.7 . . ? C16' C17' H17' 119.7 . . ? C19' C18' C23' 120.0(3) . . ? C19' C18' P3' 120.6(2) . . ? C23' C18' P3' 119.3(2) . . ? C20' C19' C18' 120.5(3) . . ? C20' C19' H19' 119.8 . . ? C18' C19' H19' 119.8 . . ? C19' C20' C21' 119.2(3) . . ? C19' C20' H20' 120.4 . . ? C21' C20' H20' 120.4 . . ? C20' C21' C22' 121.1(3) . . ? C20' C21' H21' 119.5 . . ? C22' C21' H21' 119.5 . . ? C23' C22' C21' 119.7(3) . . ? C23' C22' H22' 120.2 . . ? C21' C22' H22' 120.2 . . ? C22' C23' C18' 119.5(3) . . ? C22' C23' H23' 120.2 . . ? C18' C23' H23' 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A O1 C2 O2 -172.0(3) . . . . ? C7A O1 C2 C3 8.0(3) . . . . ? O2 C2 C3 N3 48.4(4) . . . . ? O1 C2 C3 N3 -131.6(2) . . . . ? O2 C2 C3 C3A 170.6(3) . . . . ? O1 C2 C3 C3A -9.5(3) . . . . ? O2 C2 C3 C11 -71.3(4) . . . . ? O1 C2 C3 C11 108.6(3) . . . . ? C3A C3 N3 P3 -43.4(3) . . . . ? C11 C3 N3 P3 -171.3(2) . . . . ? C2 C3 N3 P3 69.9(3) . . . . ? C3 N3 P3 O3 -13.7(3) . . . . ? C3 N3 P3 C18 -135.9(2) . . . . ? C3 N3 P3 C12 109.2(2) . . . . ? N3 C3 C3A C4 -51.5(4) . . . . ? C11 C3 C3A C4 74.8(4) . . . . ? C2 C3 C3A C4 -170.6(3) . . . . ? N3 C3 C3A C7A 126.4(3) . . . . ? C11 C3 C3A C7A -107.3(3) . . . . ? C2 C3 C3A C7A 7.3(3) . . . . ? C7A C3A C4 C5 0.6(4) . . . . ? C3 C3A C4 C5 178.3(3) . . . . ? C3A C4 C5 O5 179.4(2) . . . . ? C3A C4 C5 C6 0.8(4) . . . . ? C4 C5 O5 C8 102.6(3) . . . . ? C6 C5 O5 C8 -78.7(3) . . . . ? C4 C5 C6 O6 179.5(3) . . . . ? O5 C5 C6 O6 0.9(4) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? O5 C5 C6 C7 179.8(2) . . . . ? O6 C6 C7 C7A 179.7(3) . . . . ? C5 C6 C7 C7A 0.8(4) . . . . ? C6 C7 C7A C3A 0.6(4) . . . . ? C6 C7 C7A O1 -175.3(3) . . . . ? C4 C3A C7A C7 -1.3(5) . . . . ? C3 C3A C7A C7 -179.5(3) . . . . ? C4 C3A C7A O1 174.9(2) . . . . ? C3 C3A C7A O1 -3.3(3) . . . . ? C2 O1 C7A C7 173.2(3) . . . . ? C2 O1 C7A C3A -3.1(3) . . . . ? C5 O5 C8 C9 175.4(3) . . . . ? C5 O5 C8 C9A -163.5(7) . . . . ? O5 C8 C9 C10 117.4(5) . . . . ? C9A C8 C9 C10 27.3(19) . . . . ? O5 C8 C9A C10A -104.6(17) . . . . ? C9 C8 C9A C10A -7.5(14) . . . . ? O3 P3 C12 C13 172.7(2) . . . . ? N3 P3 C12 C13 49.2(3) . . . . ? C18 P3 C12 C13 -63.7(3) . . . . ? O3 P3 C12 C17 -9.0(3) . . . . ? N3 P3 C12 C17 -132.5(2) . . . . ? C18 P3 C12 C17 114.5(3) . . . . ? C17 C12 C13 C14 -0.2(5) . . . . ? P3 C12 C13 C14 178.1(3) . . . . ? C12 C13 C14 C15 -0.1(5) . . . . ? C13 C14 C15 C16 0.5(5) . . . . ? C14 C15 C16 C17 -0.6(5) . . . . ? C15 C16 C17 C12 0.3(5) . . . . ? C13 C12 C17 C16 0.1(5) . . . . ? P3 C12 C17 C16 -178.2(3) . . . . ? O3 P3 C18 C19 113.3(2) . . . . ? N3 P3 C18 C19 -125.3(2) . . . . ? C12 P3 C18 C19 -9.0(3) . . . . ? O3 P3 C18 C23 -60.8(3) . . . . ? N3 P3 C18 C23 60.6(2) . . . . ? C12 P3 C18 C23 176.9(2) . . . . ? C23 C18 C19 C20 -0.1(4) . . . . ? P3 C18 C19 C20 -174.1(2) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C19 C20 C21 C22 0.6(5) . . . . ? C20 C21 C22 C23 -1.0(5) . . . . ? C21 C22 C23 C18 0.8(5) . . . . ? C19 C18 C23 C22 -0.3(4) . . . . ? P3 C18 C23 C22 174.0(2) . . . . ? C7A' O1' C2' O2' -178.2(3) . . . . ? C7A' O1' C2' C3' 4.3(3) . . . . ? O2' C2' C3' N3' 55.5(4) . . . . ? O1' C2' C3' N3' -127.2(3) . . . . ? O2' C2' C3' C3A' 177.4(3) . . . . ? O1' C2' C3' C3A' -5.2(3) . . . . ? O2' C2' C3' C11' -63.3(4) . . . . ? O1' C2' C3' C11' 114.0(3) . . . . ? C3A' C3' N3' P3' -49.4(3) . . . . ? C11' C3' N3' P3' -177.6(2) . . . . ? C2' C3' N3' P3' 63.8(3) . . . . ? C3' N3' P3' O3' -27.6(3) . . . . ? C3' N3' P3' C18' -152.8(2) . . . . ? C3' N3' P3' C12' 93.8(2) . . . . ? N3' C3' C3A' C7A' 123.7(3) . . . . ? C11' C3' C3A' C7A' -110.9(3) . . . . ? C2' C3' C3A' C7A' 4.2(3) . . . . ? N3' C3' C3A' C4' -59.5(4) . . . . ? C11' C3' C3A' C4' 65.9(4) . . . . ? C2' C3' C3A' C4' -178.9(3) . . . . ? C7A' C3A' C4' C5' -0.3(4) . . . . ? C3' C3A' C4' C5' -176.9(3) . . . . ? C3A' C4' C5' O5' 176.1(3) . . . . ? C3A' C4' C5' C6' -1.7(4) . . . . ? C4' C5' O5' C8' 10.3(4) . . . . ? C6' C5' O5' C8' -171.8(3) . . . . ? O5' C5' C6' O6' 3.6(4) . . . . ? C4' C5' C6' O6' -178.3(3) . . . . ? O5' C5' C6' C7' -176.2(3) . . . . ? C4' C5' C6' C7' 1.9(4) . . . . ? O6' C6' C7' C7A' -179.8(3) . . . . ? C5' C6' C7' C7A' 0.0(4) . . . . ? C6' C7' C7A' C3A' -2.1(4) . . . . ? C6' C7' C7A' O1' 179.8(3) . . . . ? C4' C3A' C7A' C7' 2.3(4) . . . . ? C3' C3A' C7A' C7' 179.6(3) . . . . ? C4' C3A' C7A' O1' -179.4(2) . . . . ? C3' C3A' C7A' O1' -2.1(3) . . . . ? C2' O1' C7A' C7' 176.8(3) . . . . ? C2' O1' C7A' C3A' -1.5(3) . . . . ? C5' O5' C8' C9' -170.6(2) . . . . ? O5' C8' C9' C10' -4.1(4) . . . . ? O3' P3' C12' C17' -11.8(3) . . . . ? N3' P3' C12' C17' -134.8(3) . . . . ? C18' P3' C12' C17' 114.2(3) . . . . ? O3' P3' C12' C13' 170.2(2) . . . . ? N3' P3' C12' C13' 47.1(3) . . . . ? C18' P3' C12' C13' -63.9(3) . . . . ? C17' C12' C13' C14' -1.4(5) . . . . ? P3' C12' C13' C14' 176.7(2) . . . . ? C12' C13' C14' C15' 0.9(5) . . . . ? C13' C14' C15' C16' 0.7(5) . . . . ? C14' C15' C16' C17' -1.7(6) . . . . ? C13' C12' C17' C16' 0.4(5) . . . . ? P3' C12' C17' C16' -177.7(3) . . . . ? C15' C16' C17' C12' 1.2(5) . . . . ? O3' P3' C18' C19' -78.7(3) . . . . ? N3' P3' C18' C19' 44.5(3) . . . . ? C12' P3' C18' C19' 158.9(2) . . . . ? O3' P3' C18' C23' 97.9(2) . . . . ? N3' P3' C18' C23' -138.8(2) . . . . ? C12' P3' C18' C23' -24.5(3) . . . . ? C23' C18' C19' C20' 0.0(4) . . . . ? P3' C18' C19' C20' 176.6(2) . . . . ? C18' C19' C20' C21' 0.1(5) . . . . ? C19' C20' C21' C22' -0.3(5) . . . . ? C20' C21' C22' C23' 0.5(5) . . . . ? C21' C22' C23' C18' -0.4(5) . . . . ? C19' C18' C23' C22' 0.2(4) . . . . ? P3' C18' C23' C22' -176.5(2) . . . . ? 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 N3' H3' O5 0.854(18) 2.15(2) 2.969(3) 161(3) . O6 H6 O3 0.841(18) 1.790(19) 2.630(3) 176(4) 2_766 O6' H6' O3' 0.836(19) 1.869(19) 2.703(3) 176(4) 2_677 N3 H3 O5' 0.849(18) 2.86(2) 3.678(3) 161(3) 1_545 C7 H7 O3 0.95 2.57 3.212(3) 125.1 2_766 C7' H7' O3' 0.95 2.51 3.190(4) 128.6 2_677 C11 H11B O2 0.98 2.59 3.385(4) 138.1 2_666 C20 H20 O6 0.95 2.53 3.450(4) 162.2 1_545 C20' H20' O2' 0.95 2.52 3.462(4) 174.4 2_767 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.732 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.100 #============================================================================== #_eof # End of Crystallographic Information File