# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Pedro Merino' 'Elena Cerrada' 'Mariano Laguna' 'Jose A. Lopez' 'Ana Moreno' 'Tomas Tejero' _publ_contact_author_name 'Dr Pedro Merino' _publ_contact_author_address ; Quimica Organica Universidad de Zaragoza Facultad de Ciencias Edificio D. Planta 3 Campus San Francisco Zaragoza Aragon E-50009 SPAIN ; _publ_contact_author_email PMERINO@POSTA.UNIZAR.ES _publ_section_title ; An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosides ; data_piri3lam _database_code_CSD 208653 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 Br2 N2 O Zn' _chemical_formula_sum 'C13 H12 Br2 N2 O Zn' _chemical_formula_weight 437.44 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2668(7) _cell_length_b 8.1141(9) _cell_length_c 12.9245(15) _cell_angle_alpha 87.864(9) _cell_angle_beta 80.786(9) _cell_angle_gamma 84.422(9) _cell_volume 748.50(14) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 72 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 20.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 6.971 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.315 _exptl_absorpt_correction_T_max 0.894 _exptl_absorpt_process_details ; Azimuthal psi-scans of 12 reflections at 10\% intervals. Data corrected with the program: XPREP, SHELXTL v. 5 (Siemens), calculated with the treatment for thin plates (principal face: 0 0 1, minimum glancing angle: 1\%) ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3256 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2540 _reflns_number_gt 2084 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.2253P] 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 2540 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Zn Zn 0.38951(8) 0.23421(6) 0.30578(5) 0.02914(18) Uani 1 1 d . . . Br1 Br 0.52509(7) -0.04072(6) 0.32116(5) 0.04028(19) Uani 1 1 d . . . Br2 Br 0.58308(8) 0.44957(6) 0.27905(5) 0.0446(2) Uani 1 1 d . . . N1 N 0.1746(5) 0.2669(4) 0.4283(3) 0.0246(8) Uani 1 1 d . . . C1 C 0.2019(7) 0.3305(6) 0.5186(4) 0.0303(11) Uani 1 1 d . . . H1 H 0.3193 0.3701 0.5226 0.036 Uiso 1 1 calc R . . C2 C 0.0639(7) 0.3399(6) 0.6061(4) 0.0336(11) Uani 1 1 d . . . H2 H 0.0867 0.3862 0.6688 0.040 Uiso 1 1 calc R . . C3 C -0.1051(7) 0.2824(6) 0.6021(4) 0.0342(12) Uani 1 1 d . . . H3 H -0.2002 0.2866 0.6619 0.041 Uiso 1 1 calc R . . C4 C -0.1353(7) 0.2177(6) 0.5092(4) 0.0325(11) Uani 1 1 d . . . H4 H -0.2515 0.1766 0.5043 0.039 Uiso 1 1 calc R . . C5 C 0.0058(6) 0.2141(5) 0.4242(4) 0.0268(10) Uani 1 1 d . . . C6 C -0.0359(6) 0.1502(5) 0.3282(4) 0.0254(10) Uani 1 1 d . . . H6 H -0.1418 0.0883 0.3354 0.030 Uiso 1 1 calc R . . N2 N 0.0530(5) 0.1670(4) 0.2338(3) 0.0254(9) Uani 1 1 d . . . O O 0.2084(5) 0.2399(4) 0.2051(3) 0.0326(8) Uani 1 1 d . . . C7 C -0.0195(7) 0.1008(6) 0.1429(4) 0.0311(11) Uani 1 1 d . . . H7A H 0.0042 0.1764 0.0814 0.037 Uiso 1 1 calc R . . H7B H -0.1565 0.0952 0.1609 0.037 Uiso 1 1 calc R . . C8 C 0.0743(7) -0.0687(6) 0.1161(4) 0.0302(11) Uani 1 1 d . . . C9 C 0.2621(8) -0.0912(7) 0.0754(5) 0.0525(16) Uani 1 1 d . . . H9 H 0.3346 0.0010 0.0636 0.063 Uiso 1 1 calc R . . C10 C 0.3436(10) -0.2484(9) 0.0521(7) 0.071(2) Uani 1 1 d . . . H10 H 0.4736 -0.2646 0.0255 0.085 Uiso 1 1 calc R . . C11 C 0.2386(12) -0.3831(8) 0.0669(6) 0.067(2) Uani 1 1 d . . . H11 H 0.2962 -0.4908 0.0494 0.080 Uiso 1 1 calc R . . C12 C 0.0527(11) -0.3617(7) 0.1065(5) 0.0542(17) Uani 1 1 d . . . H12 H -0.0193 -0.4542 0.1171 0.065 Uiso 1 1 calc R . . C13 C -0.0310(9) -0.2040(7) 0.1314(4) 0.0428(14) Uani 1 1 d . . . H13 H -0.1606 -0.1886 0.1590 0.051 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 Zn 0.0238(3) 0.0280(3) 0.0357(3) -0.0056(2) -0.0013(2) -0.0064(2) Br1 0.0303(3) 0.0267(3) 0.0613(4) -0.0016(2) 0.0017(3) -0.0047(2) Br2 0.0359(3) 0.0330(3) 0.0670(4) -0.0023(2) -0.0070(3) -0.0149(2) N1 0.025(2) 0.0220(18) 0.027(2) -0.0031(15) -0.0031(17) -0.0037(15) C1 0.031(3) 0.029(2) 0.033(3) -0.003(2) -0.009(2) -0.005(2) C2 0.042(3) 0.027(2) 0.033(3) -0.003(2) -0.008(2) -0.002(2) C3 0.039(3) 0.031(3) 0.030(3) -0.001(2) 0.002(2) -0.004(2) C4 0.032(3) 0.034(3) 0.033(3) -0.003(2) -0.003(2) -0.009(2) C5 0.027(2) 0.020(2) 0.033(3) -0.0051(18) -0.004(2) -0.0017(18) C6 0.022(2) 0.027(2) 0.029(3) -0.0065(19) -0.005(2) -0.0054(18) N2 0.025(2) 0.0215(18) 0.031(2) -0.0076(16) -0.0062(18) 0.0001(15) O 0.0318(19) 0.0389(19) 0.0291(19) -0.0006(15) -0.0043(15) -0.0141(15) C7 0.035(3) 0.031(3) 0.029(3) -0.009(2) -0.012(2) -0.002(2) C8 0.039(3) 0.030(2) 0.023(3) -0.0100(19) -0.009(2) -0.002(2) C9 0.043(3) 0.043(3) 0.071(5) -0.025(3) -0.005(3) 0.001(3) C10 0.050(4) 0.057(4) 0.103(6) -0.033(4) -0.002(4) 0.012(3) C11 0.092(6) 0.038(4) 0.070(5) -0.018(3) -0.020(4) 0.020(4) C12 0.094(5) 0.026(3) 0.040(3) -0.004(2) 0.003(4) -0.012(3) C13 0.060(4) 0.037(3) 0.029(3) -0.009(2) 0.004(3) -0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn O 1.990(3) . ? Zn N1 2.043(4) . ? Zn Br2 2.3300(8) . ? Zn Br1 2.3641(8) . ? N1 C1 1.345(6) . ? N1 C5 1.348(6) . ? C1 C2 1.386(7) . ? C1 H1 0.9500 . ? C2 C3 1.364(7) . ? C2 H2 0.9500 . ? C3 C4 1.385(7) . ? C3 H3 0.9500 . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 C6 1.449(6) . ? C6 N2 1.295(6) . ? C6 H6 0.9500 . ? N2 O 1.320(5) . ? N2 C7 1.498(6) . ? C7 C8 1.501(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.379(8) . ? C8 C13 1.388(8) . ? C9 C10 1.376(8) . ? C9 H9 0.9500 . ? C10 C11 1.384(11) . ? C10 H10 0.9500 . ? C11 C12 1.362(10) . ? C11 H11 0.9500 . ? C12 C13 1.389(8) . ? C12 H12 0.9500 . ? C13 H13 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 O Zn N1 90.73(15) . . ? O Zn Br2 113.43(10) . . ? N1 Zn Br2 114.39(10) . . ? O Zn Br1 108.69(10) . . ? N1 Zn Br1 106.62(11) . . ? Br2 Zn Br1 119.19(3) . . ? C1 N1 C5 117.8(4) . . ? C1 N1 Zn 120.7(3) . . ? C5 N1 Zn 121.3(3) . . ? N1 C1 C2 121.9(5) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 119.8(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 118.8(5) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.9(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.7(4) . . ? N1 C5 C6 120.8(4) . . ? C4 C5 C6 116.5(4) . . ? N2 C6 C5 128.2(4) . . ? N2 C6 H6 115.9 . . ? C5 C6 H6 115.9 . . ? C6 N2 O 126.9(4) . . ? C6 N2 C7 120.3(4) . . ? O N2 C7 112.8(4) . . ? N2 O Zn 118.0(3) . . ? N2 C7 C8 110.6(4) . . ? N2 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C13 119.8(5) . . ? C9 C8 C7 121.0(5) . . ? C13 C8 C7 119.2(5) . . ? C10 C9 C8 119.4(6) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 120.8(7) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.1(6) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.7(6) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 120.1(6) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.731 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.121 data_piri2 _database_code_CSD 208654 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C52 H50 Ag2 N4 O2 P2 2+), 2(Cl O4 -)' _chemical_formula_sum 'C52 H50 Ag2 Cl2 N4 O10 P2' _chemical_formula_weight 1239.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 '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 10.978(2) _cell_length_b 11.643(2) _cell_length_c 12.334(2) _cell_angle_alpha 100.930(10) _cell_angle_beta 100.53(2) _cell_angle_gamma 111.470(10) _cell_volume 1384.5(4) _cell_formula_units_Z 1 _cell_measurement_temperature 253(2)? _cell_measurement_reflns_used 38 _cell_measurement_theta_min 9.682 _cell_measurement_theta_max 25.035 _exptl_crystal_description block _exptl_crystal_colour 'light gray' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.490 _exptl_absorpt_correction_T_max 0.596 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 16.83 _diffrn_reflns_number 9501 _diffrn_reflns_av_R_equivalents 0.1011 _diffrn_reflns_av_sigmaI/netI 0.1302 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4771 _reflns_number_gt 2665 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+2.2932P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4771 _refine_ls_number_parameters 270 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Ag Ag -0.02826(7) 0.53106(7) 0.13547(6) 0.0486(3) Uani 1 1 d . . . N1 N -0.0521(7) 0.3214(7) 0.0827(6) 0.0483(18) Uani 1 1 d . . . C1 C -0.1776(10) 0.2345(9) 0.0638(9) 0.059(3) Uani 1 1 d . . . H1 H -0.2480 0.2609 0.0507 0.080(9) Uiso 1 1 calc R . . C2 C -0.2119(11) 0.1076(10) 0.0621(10) 0.076(3) Uani 1 1 d . . . H2 H -0.3022 0.0511 0.0488 0.080(9) Uiso 1 1 calc R . . C3 C -0.1091(13) 0.0672(10) 0.0805(10) 0.079(3) Uani 1 1 d . . . H3 H -0.1275 -0.0174 0.0807 0.080(9) Uiso 1 1 calc R . . C4 C 0.0202(11) 0.1546(10) 0.0985(9) 0.065(3) Uani 1 1 d . . . H4 H 0.0912 0.1288 0.1103 0.080(9) Uiso 1 1 calc R . . C5 C 0.0500(9) 0.2829(8) 0.0998(7) 0.045(2) Uani 1 1 d . . . C6 C 0.1917(9) 0.3682(9) 0.1204(8) 0.050(2) Uani 1 1 d . . . H6 H 0.2582 0.3249 0.1425 0.080(9) Uiso 1 1 d R . . N2 N 0.2368(7) 0.4818(8) 0.1053(6) 0.0461(18) Uani 1 1 d . A . O1 O 0.1664(6) 0.5440(5) 0.0705(5) 0.0456(14) Uani 1 1 d . . . C7 C 0.3898(8) 0.5593(10) 0.1245(10) 0.063(3) Uani 1 1 d D . . H7A H 0.4011 0.5872 0.0414 0.080(9) Uiso 1 1 d R A . H7B H 0.4369 0.4934 0.1488 0.080(9) Uiso 1 1 d R . . C8A C 0.444(2) 0.6856(15) 0.2123(17) 0.056(7) Uiso 0.58(7) 1 d PGD A 1 C9A C 0.443(2) 0.687(2) 0.3252(19) 0.108(9) Uiso 0.58(7) 1 d PG A 1 C10A C 0.497(2) 0.804(3) 0.410(2) 0.120(11) Uiso 0.58(7) 1 d PG A 1 C11A C 0.552(2) 0.919(2) 0.382(3) 0.113(11) Uiso 0.58(7) 1 d PG A 1 C12A C 0.553(2) 0.9169(15) 0.269(3) 0.108(10) Uiso 0.58(7) 1 d PG A 1 C13A C 0.499(2) 0.8004(17) 0.184(2) 0.091(8) Uiso 0.58(7) 1 d PG A 1 C8B C 0.440(2) 0.6676(19) 0.2288(16) 0.052(10) Uiso 0.42(7) 1 d PGD A 2 C9B C 0.451(2) 0.653(3) 0.3391(18) 0.071(11) Uiso 0.42(7) 1 d PG A 2 C10B C 0.511(3) 0.761(3) 0.4337(17) 0.095(13) Uiso 0.42(7) 1 d PG A 2 C11B C 0.560(3) 0.884(3) 0.418(2) 0.104(14) Uiso 0.42(7) 1 d PG A 2 C12B C 0.548(3) 0.8977(19) 0.308(3) 0.084(12) Uiso 0.42(7) 1 d PG A 2 C13B C 0.489(3) 0.790(2) 0.213(2) 0.057(9) Uiso 0.42(7) 1 d PG A 2 P P -0.0704(2) 0.6841(2) 0.25660(19) 0.0415(6) Uani 1 1 d D . . C15A C -0.0876(15) 0.6520(13) 0.3913(8) 0.035(4) Uiso 0.54(3) 1 d PGD B 1 C16A C -0.2112(14) 0.5784(14) 0.4077(10) 0.061(6) Uiso 0.54(3) 1 d PG B 1 C17A C -0.2149(16) 0.5478(14) 0.5109(12) 0.088(8) Uiso 0.54(3) 1 d PG B 1 C18A C -0.0949(19) 0.5906(16) 0.5978(9) 0.061(6) Uiso 0.54(3) 1 d PG B 1 C19A C 0.0287(16) 0.6642(16) 0.5814(9) 0.076(7) Uiso 0.54(3) 1 d PG B 1 C20A C 0.0324(14) 0.6949(14) 0.4782(10) 0.054(6) Uiso 0.54(3) 1 d PG B 1 C15B C -0.041(2) 0.6730(18) 0.4031(8) 0.048(6) Uiso 0.46(3) 1 d PGD B 2 C16B C -0.152(2) 0.5962(18) 0.4335(13) 0.077(8) Uiso 0.46(3) 1 d PG B 2 C17B C -0.135(2) 0.574(2) 0.5408(15) 0.108(11) Uiso 0.46(3) 1 d PG B 2 C18B C -0.006(3) 0.628(2) 0.6176(11) 0.071(8) Uiso 0.46(3) 1 d PG B 2 C19B C 0.106(2) 0.705(2) 0.5872(12) 0.091(10) Uiso 0.46(3) 1 d PG B 2 C20B C 0.088(2) 0.7273(18) 0.4799(13) 0.075(8) Uiso 0.46(3) 1 d PG B 2 C21 C 0.0479(8) 0.8499(7) 0.2868(7) 0.042(2) Uani 1 1 d D B . C22 C 0.0297(11) 0.9504(9) 0.3505(9) 0.067(3) Uani 1 1 d . . . H22 H -0.0429 0.9337 0.3829 0.080(9) Uiso 1 1 calc R B . C23 C 0.1197(14) 1.0767(10) 0.3661(10) 0.082(4) Uani 1 1 d . B . H23 H 0.1047 1.1440 0.4064 0.080(9) Uiso 1 1 calc R . . C24 C 0.2290(13) 1.1031(11) 0.3234(11) 0.083(4) Uani 1 1 d . . . H24 H 0.2892 1.1881 0.3364 0.080(9) Uiso 1 1 calc R B . C25 C 0.2516(10) 1.0074(11) 0.2622(10) 0.074(3) Uani 1 1 d . B . H25 H 0.3268 1.0266 0.2330 0.080(9) Uiso 1 1 calc R . . C26 C 0.1619(9) 0.8800(10) 0.2428(8) 0.058(3) Uani 1 1 d . . . H26 H 0.1773 0.8142 0.2005 0.080(9) Uiso 1 1 calc R B . C14 C -0.2359(9) 0.6856(10) 0.2001(11) 0.078(4) Uani 1 1 d . B . H14A H -0.3060 0.6000 0.1795 0.13(3) Uiso 1 1 calc R . . H14B H -0.2352 0.7168 0.1334 0.13(3) Uiso 1 1 calc R . . H14C H -0.2533 0.7408 0.2577 0.13(3) Uiso 1 1 calc R . . Cl Cl 0.5081(3) 0.2709(3) 0.1604(3) 0.0758(9) Uani 1 1 d . . . O2 O 0.4757(10) 0.3298(10) 0.2543(9) 0.119(3) Uani 1 1 d . . . O3 O 0.6090(9) 0.3646(7) 0.1311(8) 0.100(3) Uani 1 1 d . . . O4 O 0.5457(11) 0.1746(11) 0.1779(15) 0.192(7) Uani 1 1 d . . . O5 O 0.3856(9) 0.2195(10) 0.0722(11) 0.139(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag 0.0537(5) 0.0515(4) 0.0439(4) 0.0012(3) 0.0122(3) 0.0320(3) N1 0.036(4) 0.048(4) 0.057(5) 0.003(4) 0.011(4) 0.020(4) C1 0.046(6) 0.057(6) 0.077(7) 0.008(5) 0.026(5) 0.025(5) C2 0.059(7) 0.053(7) 0.101(9) 0.007(6) 0.034(6) 0.010(6) C3 0.099(9) 0.043(6) 0.097(9) 0.012(6) 0.033(7) 0.030(7) C4 0.076(7) 0.056(6) 0.079(8) 0.026(6) 0.018(6) 0.042(6) C5 0.056(6) 0.049(5) 0.039(5) 0.010(4) 0.015(4) 0.033(5) C6 0.045(5) 0.054(6) 0.056(6) 0.012(5) 0.011(4) 0.030(5) N2 0.033(4) 0.062(5) 0.047(4) 0.008(4) 0.011(3) 0.027(4) O1 0.046(3) 0.051(3) 0.044(3) 0.011(3) 0.014(3) 0.025(3) C7 0.034(5) 0.080(7) 0.091(8) 0.026(6) 0.027(5) 0.035(5) P 0.0386(12) 0.0416(13) 0.0481(14) 0.0073(11) 0.0192(11) 0.0198(11) C21 0.046(5) 0.049(5) 0.035(5) 0.012(4) 0.014(4) 0.023(4) C22 0.084(7) 0.048(6) 0.069(7) 0.001(5) 0.040(6) 0.026(6) C23 0.112(10) 0.036(6) 0.078(8) -0.008(5) 0.021(8) 0.023(6) C24 0.077(8) 0.051(7) 0.101(10) 0.021(7) 0.026(7) 0.004(6) C25 0.054(6) 0.058(7) 0.091(9) 0.025(6) 0.030(6) -0.006(6) C26 0.053(6) 0.070(7) 0.057(6) 0.020(5) 0.023(5) 0.027(6) C14 0.037(5) 0.057(6) 0.129(11) 0.008(7) 0.010(6) 0.023(5) Cl 0.0601(17) 0.0581(16) 0.128(3) 0.0367(18) 0.0524(19) 0.0270(14) O2 0.120(7) 0.142(8) 0.121(8) 0.045(7) 0.076(7) 0.059(7) O3 0.111(6) 0.068(5) 0.137(8) 0.040(5) 0.080(6) 0.026(5) O4 0.144(9) 0.164(10) 0.43(2) 0.222(14) 0.180(12) 0.122(8) O5 0.079(6) 0.117(8) 0.185(11) -0.011(7) 0.013(7) 0.037(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 Ag N1 2.306(7) . ? Ag P 2.338(2) . ? Ag O1 2.381(5) . ? Ag O1 2.510(6) 2_565 ? N1 C1 1.323(11) . ? N1 C5 1.349(10) . ? C1 C2 1.380(14) . ? C2 C3 1.372(15) . ? C3 C4 1.358(14) . ? C4 C5 1.403(12) . ? C5 C6 1.448(12) . ? C6 N2 1.295(11) . ? N2 O1 1.309(8) . ? N2 C7 1.535(11) . ? O1 Ag 2.510(6) 2_565 ? C7 C8B 1.471(13) . ? C7 C8A 1.487(13) . ? C8A C9A 1.3900 . ? C8A C13A 1.3900 . ? C9A C10A 1.3900 . ? C10A C11A 1.3900 . ? C11A C12A 1.3900 . ? C12A C13A 1.3900 . ? C8B C9B 1.3900 . ? C8B C13B 1.3900 . ? C9B C10B 1.3900 . ? C10B C11B 1.3900 . ? C11B C12B 1.3900 . ? C12B C13B 1.3900 . ? P C15A 1.798(7) . ? P C21 1.808(7) . ? P C15B 1.814(8) . ? P C14 1.832(9) . ? C15A C16A 1.3900 . ? C15A C20A 1.3900 . ? C16A C17A 1.3900 . ? C17A C18A 1.3900 . ? C18A C19A 1.3900 . ? C19A C20A 1.3900 . ? C15B C16B 1.3900 . ? C15B C20B 1.3900 . ? C16B C17B 1.3900 . ? C17B C18B 1.3900 . ? C18B C19B 1.3900 . ? C19B C20B 1.3900 . ? C21 C22 1.380(11) . ? C21 C26 1.408(11) . ? C22 C23 1.391(14) . ? C23 C24 1.353(15) . ? C24 C25 1.351(15) . ? C25 C26 1.392(13) . ? Cl O4 1.369(8) . ? Cl O3 1.400(7) . ? Cl O2 1.403(9) . ? Cl O5 1.406(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag P 146.9(2) . . ? N1 Ag O1 75.4(2) . . ? P Ag O1 131.76(15) . . ? N1 Ag O1 78.4(2) . 2_565 ? P Ag O1 115.28(14) . 2_565 ? O1 Ag O1 88.66(19) . 2_565 ? C1 N1 C5 117.7(8) . . ? C1 N1 Ag 114.1(6) . . ? C5 N1 Ag 125.5(6) . . ? N1 C1 C2 124.9(9) . . ? C3 C2 C1 118.2(10) . . ? C4 C3 C2 117.8(10) . . ? C3 C4 C5 121.9(9) . . ? N1 C5 C4 119.5(8) . . ? N1 C5 C6 123.2(8) . . ? C4 C5 C6 117.3(8) . . ? N2 C6 C5 126.1(8) . . ? C6 N2 O1 128.0(7) . . ? C6 N2 C7 120.7(7) . . ? O1 N2 C7 111.3(7) . . ? N2 O1 Ag 119.7(5) . . ? N2 O1 Ag 118.8(4) . 2_565 ? Ag O1 Ag 91.34(19) . 2_565 ? C8B C7 C8A 12.3(12) . . ? C8B C7 N2 108.5(12) . . ? C8A C7 N2 112.4(10) . . ? C9A C8A C13A 120.0 . . ? C9A C8A C7 118.7(14) . . ? C13A C8A C7 121.3(14) . . ? C10A C9A C8A 120.0 . . ? C9A C10A C11A 120.0 . . ? C12A C11A C10A 120.0 . . ? C11A C12A C13A 120.0 . . ? C12A C13A C8A 120.0 . . ? C9B C8B C13B 120.0 . . ? C9B C8B C7 123.7(14) . . ? C13B C8B C7 116.0(14) . . ? C10B C9B C8B 120.0 . . ? C9B C10B C11B 120.0 . . ? C12B C11B C10B 120.0 . . ? C11B C12B C13B 120.0 . . ? C12B C13B C8B 120.0 . . ? C15A P C21 107.9(5) . . ? C15A P C15B 14.6(6) . . ? C21 P C15B 97.5(7) . . ? C15A P C14 100.4(6) . . ? C21 P C14 103.4(4) . . ? C15B P C14 113.4(8) . . ? C15A P Ag 113.9(4) . . ? C21 P Ag 116.4(3) . . ? C15B P Ag 111.8(6) . . ? C14 P Ag 113.2(4) . . ? C16A C15A C20A 120.0 . . ? C16A C15A P 123.3(7) . . ? C20A C15A P 116.5(7) . . ? C17A C16A C15A 120.0 . . ? C16A C17A C18A 120.0 . . ? C19A C18A C17A 120.0 . . ? C20A C19A C18A 120.0 . . ? C19A C20A C15A 120.0 . . ? C16B C15B C20B 120.0 . . ? C16B C15B P 117.0(11) . . ? C20B C15B P 122.8(11) . . ? C17B C16B C15B 120.0 . . ? C16B C17B C18B 120.0 . . ? C19B C18B C17B 120.0 . . ? C20B C19B C18B 120.0 . . ? C19B C20B C15B 120.0 . . ? C22 C21 C26 117.9(8) . . ? C22 C21 P 122.3(7) . . ? C26 C21 P 119.8(6) . . ? C21 C22 C23 120.0(9) . . ? C24 C23 C22 120.9(10) . . ? C25 C24 C23 120.8(10) . . ? C24 C25 C26 119.8(10) . . ? C25 C26 C21 120.6(9) . . ? O4 Cl O3 111.2(5) . . ? O4 Cl O2 113.6(8) . . ? O3 Cl O2 109.3(5) . . ? O4 Cl O5 109.8(8) . . ? O3 Cl O5 109.4(7) . . ? O2 Cl O5 103.1(6) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.724 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.112