# 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 'Qian Zhang' _publ_contact_author_email ZHANGQ651@NENU.EDU.CN _publ_section_title ; Ag-Containing All Carbon 1,3-Dipoles: Generation and Diastereospecific Cycloaddition for Furo[3,2-b]-beta/gamma-lactams ; loop_ _publ_author_name 'Qian Zhang.' 'Qun Liu.' 'Zhikun Ni.' 'Zhiguo Zhang.' # Attachment '6c.cif' # Supplementary Material (ESI) for Chemical Communications # This journal is ?The Royal Society of Chemistry 2009 #============================================================ data_6c _database_code_depnum_ccdc_archive 'CCDC 740389' #TrackingRef '6c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 Cl1 N1 O2' _chemical_formula_weight 297.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.718(5) _cell_length_b 5.683(5) _cell_length_c 14.780(5) _cell_angle_alpha 90.000 _cell_angle_beta 92.722(5) _cell_angle_gamma 90.000 _cell_volume 1402.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.149 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616.0 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8028 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.0909 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 28.36 _reflns_number_total 3505 _reflns_number_gt 1864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3208 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1894 _refine_ls_wR_factor_gt 0.1654 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.16264(5) -0.03270(17) 0.67322(6) 0.0657(4) Uani 1 1 d . . . N1 N 0.81957(13) 0.1147(4) 0.57841(15) 0.0380(6) Uani 1 1 d . . . O2 O 0.65705(12) 0.3046(4) 0.62676(15) 0.0563(6) Uani 1 1 d . . . O1 O 0.79561(13) 0.4697(4) 0.49925(16) 0.0567(6) Uani 1 1 d . . . C14 C 0.63678(15) 0.1111(5) 0.48100(18) 0.0361(6) Uani 1 1 d . . . C13 C 0.69613(16) 0.1715(5) 0.5578(2) 0.0409(7) Uani 1 1 d . . . C12 C 0.90123(15) 0.0812(5) 0.60020(17) 0.0337(6) Uani 1 1 d . . . C11 C 0.77651(16) 0.2907(5) 0.5357(2) 0.0404(7) Uani 1 1 d . . . C10 C 0.92628(17) -0.1201(5) 0.64603(19) 0.0401(7) Uani 1 1 d . . . H10A H 0.8889 -0.2320 0.6621 0.048 Uiso 1 1 calc R . . C9 C 1.03799(16) 0.2118(5) 0.59781(19) 0.0427(7) Uani 1 1 d . . . H9A H 1.0757 0.3221 0.5812 0.051 Uiso 1 1 calc R . . C8 C 0.64614(17) -0.0916(5) 0.4304(2) 0.0463(8) Uani 1 1 d . . . H8A H 0.6894 -0.1913 0.4430 0.056 Uiso 1 1 calc R . . C7 C 1.06175(16) 0.0121(5) 0.64412(18) 0.0388(7) Uani 1 1 d . . . C6 C 1.00697(17) -0.1551(5) 0.66803(19) 0.0411(7) Uani 1 1 d . . . H6A H 1.0240 -0.2904 0.6987 0.049 Uiso 1 1 calc R . . C5 C 0.57222(18) 0.2580(5) 0.4604(2) 0.0500(8) Uani 1 1 d . . . H5A H 0.5659 0.3960 0.4931 0.060 Uiso 1 1 calc R . . C15 C 0.95740(16) 0.2476(5) 0.57611(19) 0.0402(7) Uani 1 1 d . . . H15A H 0.9408 0.3831 0.5453 0.048 Uiso 1 1 calc R . . C16 C 0.74773(16) -0.0178(5) 0.60816(19) 0.0416(7) Uani 1 1 d . . . H16A H 0.7417 -0.1793 0.5855 0.050 Uiso 1 1 calc R . . C4 C 0.52640(19) -0.0004(6) 0.3420(2) 0.0536(8) Uani 1 1 d . . . H4A H 0.4891 -0.0384 0.2956 0.064 Uiso 1 1 calc R . . C17 C 0.72897(19) 0.0204(6) 0.7039(2) 0.0555(9) Uani 1 1 d . . . H17A H 0.7483 -0.0688 0.7530 0.067 Uiso 1 1 calc R . . C3 C 0.5903(2) -0.1447(6) 0.3606(2) 0.0538(8) Uani 1 1 d . . . H3A H 0.5965 -0.2800 0.3263 0.065 Uiso 1 1 calc R . . C2 C 0.51722(18) 0.1994(6) 0.3913(2) 0.0551(9) Uani 1 1 d . . . H2A H 0.4736 0.2973 0.3784 0.066 Uiso 1 1 calc R . . C1 C 0.6807(2) 0.2010(7) 0.7079(2) 0.0636(10) Uani 1 1 d . . . H1A H 0.6632 0.2565 0.7628 0.076 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 Cl1 0.0382(4) 0.0770(7) 0.0811(7) -0.0027(5) -0.0042(4) 0.0150(4) N1 0.0327(12) 0.0342(13) 0.0472(14) 0.0036(11) 0.0032(10) 0.0005(9) O2 0.0451(12) 0.0615(15) 0.0622(15) -0.0245(12) 0.0012(11) 0.0070(10) O1 0.0486(13) 0.0325(12) 0.0886(17) 0.0141(12) -0.0017(11) 0.0020(9) C14 0.0312(13) 0.0342(15) 0.0431(16) -0.0009(12) 0.0054(12) -0.0018(11) C13 0.0350(14) 0.0359(15) 0.0517(18) -0.0114(13) 0.0026(13) 0.0011(11) C12 0.0342(14) 0.0318(15) 0.0352(15) -0.0034(12) 0.0045(12) 0.0027(11) C11 0.0395(15) 0.0299(15) 0.0515(18) -0.0038(13) -0.0017(13) 0.0027(12) C10 0.0410(16) 0.0341(15) 0.0454(17) 0.0025(13) 0.0057(13) -0.0017(12) C9 0.0365(15) 0.0440(17) 0.0486(18) 0.0046(14) 0.0099(13) -0.0017(12) C8 0.0405(16) 0.0416(18) 0.0565(19) -0.0061(14) -0.0015(14) 0.0024(13) C7 0.0351(14) 0.0431(16) 0.0381(15) -0.0010(13) 0.0015(12) 0.0094(12) C6 0.0462(17) 0.0362(16) 0.0409(16) 0.0047(13) 0.0015(13) 0.0091(12) C5 0.0479(17) 0.0427(18) 0.059(2) -0.0036(15) 0.0020(15) 0.0111(14) C15 0.0431(16) 0.0359(16) 0.0420(16) 0.0066(13) 0.0060(13) 0.0041(12) C16 0.0345(15) 0.0396(16) 0.0507(18) -0.0014(14) 0.0024(13) -0.0054(12) C4 0.0417(17) 0.071(2) 0.0471(18) 0.0031(17) -0.0043(14) -0.0108(16) C17 0.0407(17) 0.077(2) 0.0488(19) 0.0026(18) 0.0043(14) -0.0102(17) C3 0.057(2) 0.0489(19) 0.055(2) -0.0099(16) -0.0038(16) -0.0052(15) C2 0.0414(17) 0.071(2) 0.053(2) 0.0044(18) -0.0033(15) 0.0127(16) C1 0.0443(18) 0.100(3) 0.047(2) -0.022(2) 0.0064(15) -0.0060(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.739(3) . ? N1 C11 1.369(3) . ? N1 C12 1.401(3) . ? N1 C16 1.501(3) . ? O2 C1 1.377(4) . ? O2 C13 1.450(4) . ? O1 C11 1.201(3) . ? C14 C5 1.387(4) . ? C14 C8 1.387(4) . ? C14 C13 1.511(4) . ? C13 C11 1.554(4) . ? C13 C16 1.548(4) . ? C12 C10 1.384(4) . ? C12 C15 1.391(4) . ? C10 C6 1.387(4) . ? C9 C15 1.385(4) . ? C9 C7 1.375(4) . ? C8 C3 1.391(4) . ? C7 C6 1.377(4) . ? C5 C2 1.382(4) . ? C16 C17 1.480(4) . ? C4 C3 1.364(5) . ? C4 C2 1.362(5) . ? C17 C1 1.309(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C12 133.7(2) . . ? C11 N1 C16 95.2(2) . . ? C12 N1 C16 130.5(2) . . ? C1 O2 C13 105.6(2) . . ? C5 C14 C8 119.2(3) . . ? C5 C14 C13 120.3(3) . . ? C8 C14 C13 120.4(2) . . ? O2 C13 C14 110.2(2) . . ? O2 C13 C11 110.1(2) . . ? C14 C13 C11 119.0(2) . . ? O2 C13 C16 106.5(2) . . ? C14 C13 C16 122.3(2) . . ? C11 C13 C16 86.3(2) . . ? C10 C12 N1 119.6(2) . . ? C10 C12 C15 119.6(2) . . ? N1 C12 C15 120.8(2) . . ? O1 C11 N1 132.9(3) . . ? O1 C11 C13 135.6(3) . . ? N1 C11 C13 91.5(2) . . ? C6 C10 C12 120.1(3) . . ? C15 C9 C7 119.4(3) . . ? C14 C8 C3 119.4(3) . . ? C6 C7 C9 121.2(3) . . ? C6 C7 Cl1 119.0(2) . . ? C9 C7 Cl1 119.9(2) . . ? C7 C6 C10 119.5(3) . . ? C14 C5 C2 120.1(3) . . ? C9 C15 C12 120.2(3) . . ? C17 C16 N1 114.5(2) . . ? C17 C16 C13 102.7(3) . . ? N1 C16 C13 86.9(2) . . ? C3 C4 C2 120.0(3) . . ? C1 C17 C16 108.5(3) . . ? C4 C3 C8 120.7(3) . . ? C4 C2 C5 120.6(3) . . ? C17 C1 O2 116.6(3) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.290 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.047 # Attachment '2j.cif' # Supplementary Material (ESI) for Chemical Communications # This journal is ?The Royal Society of Chemistry 2009 data_2j _database_code_depnum_ccdc_archive 'CCDC 740390' #TrackingRef '2j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N1 O3' _chemical_formula_weight 347.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6160(8) _cell_length_b 22.393(2) _cell_length_c 10.5250(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.881(2) _cell_angle_gamma 90.00 _cell_volume 1794.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.149 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736.0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9719 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.69 _reflns_number_total 3413 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0511P)^2^+0.2092P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3400 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.15716(16) 0.05296(6) 0.37592(12) 0.0489(4) Uani 1 1 d . . . O2 O 0.17281(19) 0.30993(6) 0.12186(14) 0.0595(4) Uani 1 1 d . . . O3 O 0.63837(17) -0.03149(6) 0.27497(15) 0.0628(4) Uani 1 1 d . . . N1 N 0.36181(19) -0.02495(6) 0.18379(15) 0.0425(4) Uani 1 1 d . . . C19 C 0.2291(2) 0.13201(8) 0.22824(17) 0.0379(4) Uani 1 1 d . . . C3 C 0.3955(3) -0.18910(9) 0.14710(19) 0.0449(5) Uani 1 1 d . . . C5 C 0.3441(2) -0.08353(8) 0.13395(17) 0.0398(4) Uani 1 1 d . . . C17 C 0.2727(3) 0.21362(9) 0.0828(2) 0.0459(5) Uani 1 1 d . . . C18 C 0.2952(2) 0.15475(9) 0.11535(19) 0.0442(5) Uani 1 1 d . . . C4 C 0.4217(2) -0.13230(8) 0.19453(18) 0.0429(5) Uani 1 1 d . . . C2 C 0.2917(2) -0.20006(9) 0.04009(18) 0.0445(5) Uani 1 1 d . . . C9 C 0.4576(2) 0.05546(8) 0.30444(17) 0.0394(4) Uani 1 1 d . . . C11 C 0.2214(2) 0.02024(8) 0.16802(19) 0.0410(4) Uani 1 1 d . . . C14 C 0.1385(3) 0.17082(9) 0.30561(19) 0.0461(5) Uani 1 1 d . . . C16 C 0.1835(2) 0.25223(8) 0.16223(19) 0.0434(5) Uani 1 1 d . . . C15 C 0.1147(3) 0.23046(9) 0.27326(19) 0.0490(5) Uani 1 1 d . . . C10 C 0.2686(2) 0.06829(8) 0.26791(16) 0.0388(4) Uani 1 1 d . . . C8 C 0.5014(2) -0.00443(8) 0.25562(19) 0.0437(5) Uani 1 1 d . . . C6 C 0.2403(3) -0.09374(9) 0.02639(19) 0.0489(5) Uani 1 1 d . . . C13 C 0.0242(3) 0.01794(9) 0.3266(2) 0.0520(5) Uani 1 1 d . . . C21 C 0.6020(3) 0.10203(10) 0.3095(2) 0.0504(5) Uani 1 1 d . . . C7 C 0.2141(3) -0.15116(9) -0.01780(19) 0.0507(5) Uani 1 1 d . . . C12 C 0.0458(2) -0.00081(9) 0.2106(2) 0.0487(5) Uani 1 1 d . . . C1 C 0.2670(4) -0.26232(12) -0.0112(3) 0.0649(7) Uani 1 1 d . . . C25 C 0.5377(3) 0.07565(11) 0.4289(2) 0.0547(6) Uani 1 1 d . . . C20 C 0.0873(4) 0.35235(11) 0.2013(3) 0.0680(7) Uani 1 1 d . . . H1 H 0.139(3) -0.1586(9) -0.0939(19) 0.057(6) Uiso 1 1 d . . . H4 H 0.494(2) -0.1254(8) 0.2683(18) 0.049(5) Uiso 1 1 d . . . H13 H 0.359(3) 0.1277(9) 0.0615(18) 0.054(6) Uiso 1 1 d . . . H15 H 0.091(3) 0.1545(10) 0.386(2) 0.072(7) Uiso 1 1 d . . . H10 H 0.464(3) 0.0994(10) 0.482(2) 0.066(7) Uiso 1 1 d . . . H6 H -0.032(3) -0.0279(9) 0.1648(19) 0.061(6) Uiso 1 1 d . . . H7 H -0.068(3) 0.0111(9) 0.388(2) 0.067(7) Uiso 1 1 d . . . H11 H 0.609(3) 0.0456(10) 0.473(2) 0.064(6) Uiso 1 1 d . . . H2 H 0.191(2) -0.0604(9) -0.0192(18) 0.053(6) Uiso 1 1 d . . . H8 H 0.717(3) 0.0885(9) 0.2768(17) 0.053(6) Uiso 1 1 d . . . H14 H 0.050(3) 0.2574(10) 0.330(2) 0.066(6) Uiso 1 1 d . . . H9 H 0.569(3) 0.1426(10) 0.2905(19) 0.064(6) Uiso 1 1 d . . . H3 H 0.448(2) -0.2209(9) 0.1906(17) 0.046(5) Uiso 1 1 d . . . H12 H 0.315(2) 0.2288(9) 0.0048(19) 0.056(6) Uiso 1 1 d . . . H16 H -0.038(4) 0.3403(10) 0.214(2) 0.081(8) Uiso 1 1 d . . . H17 H 0.149(3) 0.3544(11) 0.290(3) 0.093(9) Uiso 1 1 d . . . H18 H 0.103(3) 0.3887(12) 0.158(2) 0.083(8) Uiso 1 1 d . . . H5 H 0.223(2) 0.0370(8) 0.0829(18) 0.043(5) Uiso 1 1 d . . . H20 H 0.197(5) -0.2629(16) -0.076(3) 0.147(15) Uiso 1 1 d . . . H24 H 0.371(5) -0.2768(16) -0.034(3) 0.148(15) Uiso 1 1 d . . . H23 H 0.231(5) -0.2886(18) 0.047(4) 0.158(16) Uiso 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 O1 0.0454(8) 0.0523(9) 0.0493(8) 0.0093(6) 0.0083(6) -0.0039(6) O2 0.0739(10) 0.0339(8) 0.0709(10) 0.0026(7) 0.0082(8) 0.0103(7) O3 0.0360(8) 0.0481(9) 0.1037(12) -0.0056(8) -0.0146(7) 0.0042(6) N1 0.0376(8) 0.0356(9) 0.0541(9) -0.0025(7) -0.0056(7) 0.0018(7) C19 0.0346(9) 0.0367(10) 0.0423(10) -0.0014(8) 0.0011(8) 0.0011(7) C3 0.0465(11) 0.0400(12) 0.0482(11) 0.0029(10) 0.0039(9) 0.0056(9) C5 0.0371(10) 0.0367(11) 0.0457(10) -0.0002(9) 0.0022(8) -0.0007(8) C17 0.0482(11) 0.0418(12) 0.0481(12) 0.0058(10) 0.0081(9) 0.0056(9) C18 0.0466(11) 0.0388(11) 0.0475(11) -0.0002(9) 0.0100(9) 0.0086(9) C4 0.0428(10) 0.0427(12) 0.0432(11) -0.0008(9) -0.0022(9) 0.0016(9) C2 0.0433(10) 0.0416(11) 0.0488(11) -0.0037(9) 0.0064(9) -0.0027(9) C9 0.0380(10) 0.0352(10) 0.0451(11) 0.0031(8) -0.0030(8) -0.0030(8) C11 0.0401(10) 0.0348(10) 0.0480(11) 0.0048(9) -0.0045(8) 0.0035(8) C14 0.0515(12) 0.0430(12) 0.0440(11) -0.0009(9) 0.0067(9) 0.0038(9) C16 0.0423(10) 0.0335(11) 0.0543(12) -0.0024(9) -0.0024(9) 0.0037(8) C15 0.0568(12) 0.0432(12) 0.0473(12) -0.0089(10) 0.0068(10) 0.0095(10) C10 0.0363(10) 0.0374(10) 0.0427(10) 0.0027(8) 0.0030(8) -0.0011(8) C8 0.0336(10) 0.0392(11) 0.0583(12) 0.0040(9) -0.0014(8) -0.0027(8) C6 0.0515(12) 0.0423(12) 0.0528(12) 0.0029(10) -0.0082(9) 0.0023(9) C13 0.0356(11) 0.0460(13) 0.0743(16) 0.0163(11) 0.0021(11) -0.0016(9) C21 0.0451(12) 0.0418(12) 0.0641(14) 0.0044(11) -0.0063(10) -0.0084(10) C7 0.0528(12) 0.0515(13) 0.0474(12) -0.0039(10) -0.0066(10) -0.0035(10) C12 0.0358(10) 0.0390(11) 0.0711(15) 0.0061(11) -0.0092(10) -0.0006(9) C1 0.0715(18) 0.0474(14) 0.0758(19) -0.0132(14) -0.0018(15) -0.0031(13) C25 0.0550(13) 0.0580(14) 0.0509(13) 0.0000(12) -0.0102(11) -0.0059(11) C20 0.0723(18) 0.0339(13) 0.098(2) -0.0096(14) 0.0053(15) 0.0063(12) _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 C13 1.376(2) . ? O1 C10 1.470(2) . ? O2 C16 1.362(2) . ? O2 C20 1.429(3) . ? O3 C8 1.221(2) . ? N1 C8 1.374(2) . ? N1 C5 1.418(2) . ? N1 C11 1.480(2) . ? C19 C14 1.383(2) . ? C19 C18 1.394(3) . ? C19 C10 1.516(2) . ? C3 C4 1.380(3) . ? C3 C2 1.388(3) . ? C5 C6 1.390(3) . ? C5 C4 1.392(2) . ? C17 C18 1.372(3) . ? C17 C16 1.388(3) . ? C2 C7 1.381(3) . ? C2 C1 1.506(3) . ? C9 C8 1.476(3) . ? C9 C25 1.506(3) . ? C9 C10 1.512(2) . ? C9 C21 1.516(3) . ? C11 C12 1.494(3) . ? C11 C10 1.543(3) . ? C14 C15 1.390(3) . ? C16 C15 1.377(3) . ? C6 C7 1.381(3) . ? C13 C12 1.304(3) . ? C21 C25 1.479(3) . ? 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 C13 O1 C10 105.78(15) . . ? C16 O2 C20 118.27(18) . . ? C8 N1 C5 125.53(15) . . ? C8 N1 C11 112.63(14) . . ? C5 N1 C11 121.76(14) . . ? C14 C19 C18 117.56(17) . . ? C14 C19 C10 121.88(16) . . ? C18 C19 C10 120.40(16) . . ? C4 C3 C2 122.28(19) . . ? C6 C5 C4 118.46(18) . . ? C6 C5 N1 120.20(17) . . ? C4 C5 N1 121.26(16) . . ? C18 C17 C16 120.56(19) . . ? C17 C18 C19 121.23(18) . . ? C3 C4 C5 119.96(18) . . ? C7 C2 C3 116.88(18) . . ? C7 C2 C1 121.7(2) . . ? C3 C2 C1 121.4(2) . . ? C8 C9 C25 118.99(17) . . ? C8 C9 C10 107.68(14) . . ? C25 C9 C10 122.39(17) . . ? C8 C9 C21 117.99(17) . . ? C25 C9 C21 58.61(13) . . ? C10 C9 C21 124.45(16) . . ? N1 C11 C12 113.54(15) . . ? N1 C11 C10 103.89(14) . . ? C12 C11 C10 102.46(16) . . ? C19 C14 C15 121.61(19) . . ? O2 C16 C15 125.37(17) . . ? O2 C16 C17 115.49(17) . . ? C15 C16 C17 119.14(18) . . ? C16 C15 C14 119.88(18) . . ? O1 C10 C9 108.53(13) . . ? O1 C10 C19 108.58(14) . . ? C9 C10 C19 115.66(14) . . ? O1 C10 C11 103.48(14) . . ? C9 C10 C11 104.58(14) . . ? C19 C10 C11 115.19(14) . . ? O3 C8 N1 125.29(18) . . ? O3 C8 C9 126.17(17) . . ? N1 C8 C9 108.54(15) . . ? C7 C6 C5 120.31(19) . . ? C12 C13 O1 115.72(19) . . ? C25 C21 C9 60.37(13) . . ? C6 C7 C2 122.09(19) . . ? C13 C12 C11 107.80(18) . . ? C21 C25 C9 61.03(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.190 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.032