# 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 _publ_contact_author_name 'Guofu Zhong' _publ_contact_author_address ; Chemistry & Biological Chemistry Nanyang Technological University 21 Nanyang Link Singapore 637371 SINGAPORE ; _publ_contact_author_email GUOFU@NTU.EDU.SG _publ_section_title ; Diastereoselective HOTf-catalyzed three-component one-pot 1,3-dipolar cycloaddition of ?-diazo ester, nitrosobenzene and electron-deficient alkene ; loop_ _publ_author_name 'Guofu Zhong.' 'Yuxuan Hou.' 'Yunbo Lv.' 'Bin Tan.' 'Fei Wang.' ; Zhen-Jiang Xu ; 'Xiaofei Zeng.' 'Di Zhu.' # Attachment 'zgf43.cif' data_zgf43 _database_code_depnum_ccdc_archive 'CCDC 755558' #TrackingRef 'zgf43.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N O7' _chemical_formula_sum 'C16 H19 N O7' _chemical_formula_weight 337.32 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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 9.0084(2) _cell_length_b 19.0142(5) _cell_length_c 19.0720(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3266.80(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5245 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 32.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46347 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 33.29 _reflns_number_total 6257 _reflns_number_gt 4478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.6896P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6257 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.87692(12) 0.07815(5) 0.36372(5) 0.02111(19) Uani 1 1 d . . . C2 C 0.80401(14) 0.09722(6) 0.30194(6) 0.0278(2) Uani 1 1 d . . . H2 H 0.8381 0.1362 0.2753 0.033 Uiso 1 1 calc R . . C3 C 0.68142(15) 0.05894(7) 0.27961(7) 0.0333(3) Uani 1 1 d . . . H3 H 0.6318 0.0719 0.2376 0.040 Uiso 1 1 calc R . . C4 C 0.63102(15) 0.00195(7) 0.31831(8) 0.0361(3) Uani 1 1 d . . . H4 H 0.5461 -0.0236 0.3034 0.043 Uiso 1 1 calc R . . C5 C 0.70537(15) -0.01732(6) 0.37885(7) 0.0333(3) Uani 1 1 d . . . H5 H 0.6714 -0.0565 0.4052 0.040 Uiso 1 1 calc R . . C6 C 0.82914(13) 0.01994(6) 0.40158(6) 0.0266(2) Uani 1 1 d . . . H6 H 0.8807 0.0057 0.4427 0.032 Uiso 1 1 calc R . . C7 C 1.02211(12) 0.14864(5) 0.50039(5) 0.01932(18) Uani 1 1 d . . . H7 H 1.0927 0.1488 0.5408 0.023 Uiso 1 1 calc R . . C8 C 0.86561(12) 0.13335(5) 0.52561(5) 0.02121(19) Uani 1 1 d . . . C9 C 0.72093(18) 0.05685(9) 0.59444(9) 0.0474(4) Uani 1 1 d . . . H9A H 0.6632 0.0964 0.6129 0.071 Uiso 1 1 calc R . . H9B H 0.7330 0.0212 0.6311 0.071 Uiso 1 1 calc R . . H9C H 0.6688 0.0362 0.5543 0.071 Uiso 1 1 calc R . . C10 C 1.03610(11) 0.21658(5) 0.45878(5) 0.01890(18) Uani 1 1 d . . . H10 H 1.1443 0.2281 0.4561 0.023 Uiso 1 1 calc R . . C11 C 0.95799(12) 0.28149(5) 0.48507(5) 0.02161(19) Uani 1 1 d . . . C12 C 0.93685(15) 0.35671(7) 0.58274(7) 0.0331(3) Uani 1 1 d . . . H12A H 1.0075 0.3921 0.5659 0.050 Uiso 1 1 calc R . . H12B H 0.9406 0.3546 0.6341 0.050 Uiso 1 1 calc R . . H12C H 0.8364 0.3695 0.5678 0.050 Uiso 1 1 calc R . . C13 C 0.98704(12) 0.19540(5) 0.38521(5) 0.02010(18) Uani 1 1 d . . . H13 H 0.8805 0.2081 0.3777 0.024 Uiso 1 1 calc R . . C14 C 1.08452(14) 0.23069(6) 0.32974(6) 0.0268(2) Uani 1 1 d . . . C15 C 1.0897(2) 0.27391(8) 0.21307(6) 0.0497(4) Uani 1 1 d . . . H15A H 1.0541 0.2563 0.1672 0.060 Uiso 1 1 calc R . . H15B H 1.1977 0.2648 0.2161 0.060 Uiso 1 1 calc R . . C16 C 1.0617(3) 0.34986(10) 0.21830(10) 0.0669(6) Uani 1 1 d . . . H16A H 0.9546 0.3586 0.2160 0.100 Uiso 1 1 calc R . . H16B H 1.1112 0.3741 0.1795 0.100 Uiso 1 1 calc R . . H16C H 1.1006 0.3675 0.2630 0.100 Uiso 1 1 calc R . . N1 N 1.00605(10) 0.11777(5) 0.38258(4) 0.02071(17) Uani 1 1 d . . . O1 O 1.06537(9) 0.09621(4) 0.44975(4) 0.02187(15) Uani 1 1 d . . . O2 O 0.75675(9) 0.16245(4) 0.50340(4) 0.02883(18) Uani 1 1 d . . . O3 O 0.86539(10) 0.08154(5) 0.57228(5) 0.0338(2) Uani 1 1 d . . . O4 O 0.89504(11) 0.32298(5) 0.44771(5) 0.0339(2) Uani 1 1 d . . . O5 O 0.97541(9) 0.28857(4) 0.55395(4) 0.02515(17) Uani 1 1 d . . . O6 O 1.20783(12) 0.25074(8) 0.33981(6) 0.0585(4) Uani 1 1 d . . . O7 O 1.01314(13) 0.23691(6) 0.26961(4) 0.0452(3) 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 C1 0.0200(5) 0.0196(4) 0.0238(4) -0.0035(3) 0.0015(4) 0.0005(3) C2 0.0290(6) 0.0294(5) 0.0250(5) -0.0017(4) -0.0021(4) -0.0031(4) C3 0.0307(6) 0.0362(6) 0.0331(6) -0.0080(4) -0.0068(5) -0.0031(5) C4 0.0272(6) 0.0314(6) 0.0499(7) -0.0124(5) -0.0018(5) -0.0062(5) C5 0.0323(6) 0.0205(5) 0.0471(7) -0.0031(4) 0.0048(5) -0.0048(4) C6 0.0285(6) 0.0187(5) 0.0326(5) -0.0004(4) 0.0017(4) 0.0010(4) C7 0.0185(5) 0.0193(4) 0.0202(4) 0.0009(3) -0.0018(3) 0.0028(3) C8 0.0236(5) 0.0184(4) 0.0216(4) 0.0006(3) 0.0022(4) 0.0018(4) C9 0.0427(9) 0.0445(8) 0.0548(8) 0.0173(6) 0.0205(7) -0.0047(6) C10 0.0174(4) 0.0191(4) 0.0202(4) 0.0014(3) -0.0010(3) -0.0004(3) C11 0.0205(5) 0.0183(4) 0.0260(5) 0.0007(3) -0.0015(4) -0.0018(3) C12 0.0336(7) 0.0266(5) 0.0390(6) -0.0117(4) 0.0015(5) 0.0007(5) C13 0.0213(5) 0.0190(4) 0.0200(4) 0.0022(3) -0.0011(3) -0.0005(3) C14 0.0309(6) 0.0259(5) 0.0236(5) 0.0044(4) 0.0024(4) -0.0004(4) C15 0.0880(13) 0.0419(8) 0.0192(5) 0.0046(5) 0.0042(6) -0.0233(8) C16 0.0974(16) 0.0482(10) 0.0551(10) 0.0245(8) 0.0031(10) -0.0068(10) N1 0.0222(4) 0.0204(4) 0.0195(4) 0.0009(3) -0.0011(3) 0.0007(3) O1 0.0215(4) 0.0212(3) 0.0229(3) 0.0006(2) -0.0017(3) 0.0058(3) O2 0.0210(4) 0.0272(4) 0.0383(4) 0.0041(3) 0.0024(3) 0.0042(3) O3 0.0322(5) 0.0332(5) 0.0360(4) 0.0157(3) 0.0062(4) 0.0014(4) O4 0.0421(5) 0.0235(4) 0.0362(4) 0.0019(3) -0.0097(4) 0.0082(4) O5 0.0274(4) 0.0227(4) 0.0253(4) -0.0035(3) 0.0006(3) 0.0009(3) O6 0.0297(6) 0.1008(10) 0.0449(6) 0.0347(6) -0.0004(4) -0.0155(6) O7 0.0676(7) 0.0455(6) 0.0225(4) 0.0109(4) -0.0090(4) -0.0292(5) _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 C1 C6 1.3900(15) . ? C1 C2 1.3968(16) . ? C1 N1 1.4317(14) . ? C2 C3 1.3895(17) . ? C3 C4 1.388(2) . ? C4 C5 1.384(2) . ? C5 C6 1.3903(17) . ? C7 O1 1.4416(12) . ? C7 C8 1.5177(15) . ? C7 C10 1.5213(14) . ? C8 O2 1.2030(13) . ? C8 O3 1.3277(13) . ? C9 O3 1.4465(17) . ? C10 C11 1.5065(14) . ? C10 C13 1.5253(14) . ? C11 O4 1.2048(13) . ? C11 O5 1.3298(12) . ? C12 O5 1.4495(14) . ? C13 N1 1.4868(14) . ? C13 C14 1.5299(15) . ? C14 O6 1.1900(16) . ? C14 O7 1.3200(14) . ? C15 O7 1.4608(16) . ? C15 C16 1.469(3) . ? N1 O1 1.4473(11) . ? 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 C6 C1 C2 119.95(10) . . ? C6 C1 N1 122.69(10) . . ? C2 C1 N1 117.22(9) . . ? C3 C2 C1 119.77(11) . . ? C4 C3 C2 120.40(12) . . ? C5 C4 C3 119.48(11) . . ? C4 C5 C6 120.88(12) . . ? C1 C6 C5 119.48(11) . . ? O1 C7 C8 109.33(8) . . ? O1 C7 C10 102.43(7) . . ? C8 C7 C10 113.88(8) . . ? O2 C8 O3 125.18(10) . . ? O2 C8 C7 123.88(9) . . ? O3 C8 C7 110.85(9) . . ? C11 C10 C7 118.90(8) . . ? C11 C10 C13 112.78(8) . . ? C7 C10 C13 103.39(8) . . ? O4 C11 O5 124.99(10) . . ? O4 C11 C10 124.01(9) . . ? O5 C11 C10 110.89(8) . . ? N1 C13 C10 105.06(8) . . ? N1 C13 C14 110.25(9) . . ? C10 C13 C14 110.74(9) . . ? O6 C14 O7 124.49(11) . . ? O6 C14 C13 124.38(10) . . ? O7 C14 C13 111.12(10) . . ? O7 C15 C16 110.00(15) . . ? C1 N1 O1 111.92(8) . . ? C1 N1 C13 115.92(8) . . ? O1 N1 C13 107.09(7) . . ? C7 O1 N1 107.30(7) . . ? C8 O3 C9 115.98(10) . . ? C11 O5 C12 115.88(9) . . ? C14 O7 C15 117.03(12) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 33.29 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.362 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.061 # Attachment 'zgf51.cif' data_zgf51 _database_code_depnum_ccdc_archive 'CCDC 755559' #TrackingRef 'zgf51.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration unk _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 N2 O6' _chemical_formula_sum 'C25 H22 N2 O6' _chemical_formula_weight 446.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.8851(3) _cell_length_b 12.8368(5) _cell_length_c 19.7416(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2251.65(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2916 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 21.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13265 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2225 _reflns_number_gt 1544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+3.3910P] 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 SHELXL _refine_ls_extinction_coef 0.0084(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2225 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1533 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C1 C -0.2243(8) 0.2233(5) 0.2743(3) 0.0597(17) Uani 1 1 d . . . H1 H -0.1432 0.1817 0.2620 0.072 Uiso 1 1 calc R . . C2 C -0.3474(7) 0.1784(5) 0.3050(3) 0.0625(17) Uani 1 1 d . . . H2 H -0.3503 0.1071 0.3132 0.075 Uiso 1 1 calc R . . C3 C -0.4643(8) 0.2404(6) 0.3231(3) 0.0630(17) Uani 1 1 d . . . C4 C -0.4664(8) 0.3447(6) 0.3102(4) 0.0708(19) Uani 1 1 d . . . H4 H -0.5486 0.3853 0.3225 0.085 Uiso 1 1 calc R . . C5 C -0.3434(7) 0.3883(5) 0.2785(3) 0.0619(17) Uani 1 1 d . . . H5 H -0.3437 0.4591 0.2685 0.074 Uiso 1 1 calc R . . C6 C -0.2191(7) 0.3284(4) 0.2614(3) 0.0496(14) Uani 1 1 d . . . C7 C -0.0881(6) 0.3792(4) 0.2291(3) 0.0452(13) Uani 1 1 d . . . H7 H -0.1043 0.4546 0.2264 0.054 Uiso 1 1 calc R . . C8 C 0.0682(7) 0.3561(4) 0.2609(3) 0.0475(14) Uani 1 1 d . . . H8 H 0.0628 0.2920 0.2878 0.057 Uiso 1 1 calc R . . C9 C 0.1210(7) 0.4461(4) 0.3058(3) 0.0523(15) Uani 1 1 d . . . C10 C 0.0323(7) 0.4742(4) 0.3663(3) 0.0517(15) Uani 1 1 d . . . C11 C -0.0563(8) 0.4035(5) 0.4005(3) 0.0610(17) Uani 1 1 d . . . H11 H -0.0614 0.3348 0.3858 0.073 Uiso 1 1 calc R . . C12 C -0.1381(9) 0.4350(6) 0.4571(3) 0.079(2) Uani 1 1 d . . . H12 H -0.1976 0.3870 0.4801 0.095 Uiso 1 1 calc R . . C13 C -0.1317(10) 0.5355(7) 0.4792(4) 0.085(2) Uani 1 1 d . . . H13 H -0.1859 0.5556 0.5173 0.103 Uiso 1 1 calc R . . C14 C -0.0462(10) 0.6063(6) 0.4456(3) 0.077(2) Uani 1 1 d . . . H14 H -0.0449 0.6753 0.4599 0.092 Uiso 1 1 calc R . . C15 C 0.0393(9) 0.5763(5) 0.3900(3) 0.0656(18) Uani 1 1 d . . . H15 H 0.1014 0.6245 0.3687 0.079 Uiso 1 1 calc R . . C16 C 0.1721(7) 0.3388(4) 0.1992(3) 0.0511(14) Uani 1 1 d . . . H16 H 0.2522 0.3912 0.1996 0.061 Uiso 1 1 calc R . . C17 C 0.2414(8) 0.2315(5) 0.1966(3) 0.0554(15) Uani 1 1 d . . . C18 C 0.4319(9) 0.1349(5) 0.1385(4) 0.074(2) Uani 1 1 d . . . H18A H 0.3622 0.0794 0.1273 0.089 Uiso 1 1 calc R . . H18B H 0.4870 0.1152 0.1789 0.089 Uiso 1 1 calc R . . C19 C 0.5383(11) 0.1535(7) 0.0809(4) 0.120(4) Uani 1 1 d . . . H19A H 0.4820 0.1676 0.0404 0.180 Uiso 1 1 calc R . . H19B H 0.5995 0.0928 0.0742 0.180 Uiso 1 1 calc R . . H19C H 0.6015 0.2120 0.0912 0.180 Uiso 1 1 calc R . . C20 C 0.0922(7) 0.4508(4) 0.1043(3) 0.0508(15) Uani 1 1 d . . . C21 C 0.2318(9) 0.4703(5) 0.0743(3) 0.0653(19) Uani 1 1 d . . . H21 H 0.3105 0.4232 0.0793 0.078 Uiso 1 1 calc R . . C22 C 0.2515(9) 0.5588(6) 0.0376(3) 0.073(2) Uani 1 1 d . . . H22 H 0.3451 0.5722 0.0184 0.088 Uiso 1 1 calc R . . C23 C 0.1367(10) 0.6287(6) 0.0283(4) 0.075(2) Uani 1 1 d . . . H23 H 0.1518 0.6883 0.0024 0.090 Uiso 1 1 calc R . . C24 C -0.0015(9) 0.6097(5) 0.0578(4) 0.075(2) Uani 1 1 d . . . H24 H -0.0795 0.6574 0.0525 0.090 Uiso 1 1 calc R . . C25 C -0.0241(8) 0.5206(5) 0.0947(3) 0.0610(17) Uani 1 1 d . . . H25 H -0.1182 0.5072 0.1134 0.073 Uiso 1 1 calc R . . N1 N -0.5949(7) 0.1912(6) 0.3571(3) 0.0801(19) Uani 1 1 d . . . N2 N 0.0772(6) 0.3538(4) 0.1383(2) 0.0523(12) Uani 1 1 d . . . O1 O -0.5956(7) 0.0974(5) 0.3648(3) 0.111(2) Uani 1 1 d . . . O2 O -0.6981(7) 0.2505(5) 0.3754(3) 0.104(2) Uani 1 1 d . . . O3 O -0.0748(5) 0.3362(3) 0.16208(19) 0.0560(11) Uani 1 1 d . . . O4 O 0.2322(5) 0.4978(3) 0.2901(2) 0.0677(13) Uani 1 1 d . . . O5 O 0.2083(6) 0.1581(3) 0.2297(2) 0.0736(14) Uani 1 1 d . . . O6 O 0.3504(5) 0.2320(3) 0.1499(2) 0.0693(13) 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 C1 0.061(4) 0.051(3) 0.067(4) -0.002(3) 0.012(4) -0.006(3) C2 0.063(4) 0.062(4) 0.063(4) 0.010(3) 0.004(4) -0.018(4) C3 0.053(4) 0.082(5) 0.054(4) 0.002(3) 0.007(3) -0.012(4) C4 0.051(4) 0.075(5) 0.086(5) -0.008(4) 0.009(4) 0.001(4) C5 0.050(4) 0.055(4) 0.080(5) 0.000(3) 0.001(3) -0.001(3) C6 0.048(4) 0.047(3) 0.053(3) -0.005(3) 0.004(3) -0.001(3) C7 0.042(3) 0.043(3) 0.050(3) 0.000(3) -0.004(3) -0.004(3) C8 0.058(4) 0.039(3) 0.045(3) -0.002(3) 0.003(3) -0.002(3) C9 0.060(4) 0.044(3) 0.052(3) 0.001(3) 0.000(3) 0.002(3) C10 0.060(4) 0.054(3) 0.042(3) 0.000(3) 0.009(3) -0.001(3) C11 0.069(4) 0.064(4) 0.050(3) -0.002(3) -0.001(4) -0.008(4) C12 0.089(6) 0.093(5) 0.055(4) 0.004(4) 0.005(4) -0.007(5) C13 0.094(6) 0.099(6) 0.064(5) -0.006(5) 0.013(4) 0.014(5) C14 0.105(6) 0.066(4) 0.059(4) -0.014(4) 0.003(4) 0.018(5) C15 0.083(5) 0.054(4) 0.060(4) -0.002(3) -0.009(4) 0.008(4) C16 0.059(4) 0.046(3) 0.049(3) 0.001(3) -0.003(3) 0.002(3) C17 0.064(4) 0.052(3) 0.050(3) -0.007(3) 0.003(3) 0.010(3) C18 0.086(5) 0.063(4) 0.074(4) -0.003(4) 0.010(4) 0.034(4) C19 0.132(9) 0.117(7) 0.111(7) 0.007(6) 0.049(6) 0.056(7) C20 0.062(4) 0.050(3) 0.041(3) 0.001(3) -0.003(3) -0.002(3) C21 0.076(5) 0.063(4) 0.057(4) 0.006(3) 0.011(4) 0.004(4) C22 0.075(5) 0.079(5) 0.065(4) 0.012(4) 0.012(4) -0.001(4) C23 0.090(6) 0.067(4) 0.068(4) 0.022(4) 0.000(4) 0.000(4) C24 0.080(6) 0.069(4) 0.075(5) 0.017(4) -0.008(4) 0.011(4) C25 0.058(4) 0.064(4) 0.061(4) 0.010(3) -0.003(3) 0.008(3) N1 0.053(4) 0.121(6) 0.067(4) 0.007(4) 0.000(3) -0.017(4) N2 0.055(3) 0.055(3) 0.047(3) -0.002(2) 0.007(2) -0.001(3) O1 0.081(4) 0.128(5) 0.124(5) 0.057(4) -0.007(4) -0.020(4) O2 0.070(4) 0.148(5) 0.094(4) -0.020(4) 0.019(3) -0.023(4) O3 0.060(3) 0.055(2) 0.053(2) -0.001(2) 0.002(2) -0.009(2) O4 0.064(3) 0.059(2) 0.080(3) -0.012(2) 0.010(3) -0.014(2) O5 0.105(4) 0.050(2) 0.066(3) 0.010(2) 0.006(3) 0.009(3) O6 0.074(3) 0.055(3) 0.079(3) 0.001(2) 0.016(3) 0.018(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 C1 C6 1.373(8) . ? C1 C2 1.378(8) . ? C2 C3 1.356(9) . ? C3 C4 1.363(9) . ? C3 N1 1.482(8) . ? C4 C5 1.378(9) . ? C5 C6 1.388(8) . ? C6 C7 1.479(8) . ? C7 O3 1.439(6) . ? C7 C8 1.553(7) . ? C8 C9 1.530(8) . ? C8 C16 1.543(8) . ? C9 O4 1.229(7) . ? C9 C10 1.476(8) . ? C10 C11 1.378(8) . ? C10 C15 1.394(8) . ? C11 C12 1.393(9) . ? C12 C13 1.363(10) . ? C13 C14 1.358(10) . ? C14 C15 1.389(9) . ? C16 N2 1.482(7) . ? C16 C17 1.510(8) . ? C17 O5 1.183(7) . ? C17 O6 1.336(7) . ? C18 O6 1.458(7) . ? C18 C19 1.497(10) . ? C20 C25 1.381(8) . ? C20 C21 1.398(9) . ? C20 N2 1.421(7) . ? C21 C22 1.358(8) . ? C22 C23 1.372(10) . ? C23 C24 1.380(10) . ? C24 C25 1.371(8) . ? N1 O1 1.214(8) . ? N1 O2 1.244(8) . ? N2 O3 1.447(6) . ? 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 C6 C1 C2 121.3(6) . . ? C3 C2 C1 118.6(6) . . ? C2 C3 C4 122.6(6) . . ? C2 C3 N1 118.0(6) . . ? C4 C3 N1 119.4(7) . . ? C3 C4 C5 118.2(6) . . ? C4 C5 C6 121.1(6) . . ? C1 C6 C5 118.2(6) . . ? C1 C6 C7 122.7(6) . . ? C5 C6 C7 119.1(5) . . ? O3 C7 C6 106.9(4) . . ? O3 C7 C8 103.0(4) . . ? C6 C7 C8 116.4(4) . . ? C9 C8 C16 112.5(5) . . ? C9 C8 C7 111.3(5) . . ? C16 C8 C7 104.1(4) . . ? O4 C9 C10 120.1(5) . . ? O4 C9 C8 120.5(5) . . ? C10 C9 C8 119.3(5) . . ? C11 C10 C15 118.6(6) . . ? C11 C10 C9 122.8(5) . . ? C15 C10 C9 118.6(6) . . ? C10 C11 C12 120.1(6) . . ? C13 C12 C11 120.6(7) . . ? C14 C13 C12 120.0(7) . . ? C13 C14 C15 120.5(7) . . ? C14 C15 C10 120.1(7) . . ? N2 C16 C17 108.8(5) . . ? N2 C16 C8 106.3(5) . . ? C17 C16 C8 113.8(5) . . ? O5 C17 O6 124.4(6) . . ? O5 C17 C16 127.2(6) . . ? O6 C17 C16 108.4(5) . . ? O6 C18 C19 107.2(6) . . ? C25 C20 C21 119.3(6) . . ? C25 C20 N2 124.3(6) . . ? C21 C20 N2 116.1(6) . . ? C22 C21 C20 119.4(7) . . ? C21 C22 C23 121.5(7) . . ? C22 C23 C24 119.3(6) . . ? C25 C24 C23 120.1(7) . . ? C24 C25 C20 120.3(7) . . ? O1 N1 O2 124.6(7) . . ? O1 N1 C3 118.8(8) . . ? O2 N1 C3 116.6(7) . . ? C20 N2 O3 112.2(5) . . ? C20 N2 C16 116.3(5) . . ? O3 N2 C16 104.3(4) . . ? C7 O3 N2 108.3(4) . . ? C17 O6 C18 117.5(5) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.237 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.061