data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Cunningham, D.' 'Fenlon, Julie' 'Heaney, F.' 'McArdle, P.' ; o'Mahony, Colm ; _publ_contact_author_name 'Dr F. Heaney' _publ_contact_author_address ; Department of Chemistry National University of Ireland Maynooth Co. Kildare IRELAND ; _publ_contact_author_email 'CHEMISTRY.DEPARTMENT@MAY.IE' _publ_section_title ; Nitrogen-containing heterocycles, 1,3-dipolar cycloaddition of stabilised nitrones with alkynes; primary cycloadducts, first and second generation rearrangement processes ; data_jf4 _database_code_CSD 168302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N O7' _chemical_formula_weight 347.32 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 ? _symmetry_space_group_name_H-M ? 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 9.023(3) _cell_length_b 11.0408(16) _cell_length_c 16.112(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1605.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9778 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1899 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.95 _reflns_number_total 1823 _reflns_number_gt 1131 _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^)+(0.0716P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 1823 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.5265(3) 0.7280(3) 0.07200(16) 0.0379(7) Uani 1 1 d . . . N1 N 0.4586(4) 0.8282(3) 0.1189(2) 0.0327(8) Uani 1 1 d . . . O5 O 0.8581(3) 0.5735(3) 0.11777(19) 0.0453(8) Uani 1 1 d . . . O2 O 0.3991(3) 0.9218(3) 0.2802(2) 0.0517(9) Uani 1 1 d . . . O4 O 0.6774(4) 0.5221(3) 0.0293(2) 0.0510(9) Uani 1 1 d . . . O7 O 0.8021(3) 0.6748(3) 0.28551(19) 0.0444(8) Uani 1 1 d . . . O6 O 0.9253(3) 0.8304(3) 0.2280(2) 0.0503(9) Uani 1 1 d . . . O1 O 0.6328(4) 0.9509(4) 0.30550(19) 0.0579(10) Uani 1 1 d . . . C1 C 0.5852(4) 0.8794(4) 0.1692(2) 0.0302(10) Uani 1 1 d . . . C2 C 0.6471(4) 0.9882(4) 0.1224(2) 0.0317(10) Uani 1 1 d . . . C3 C 0.5746(5) 1.0983(4) 0.1248(3) 0.0431(12) Uani 1 1 d . . . H3 H 0.4925 1.1073 0.1591 0.056 Uiso 1 1 calc R . . C4 C 0.6207(5) 1.1948(4) 0.0776(3) 0.0479(13) Uani 1 1 d . . . H4 H 0.5710 1.2685 0.0808 0.062 Uiso 1 1 calc R . . C5 C 0.7416(5) 1.1818(4) 0.0255(3) 0.0510(13) Uani 1 1 d . . . H5 H 0.7728 1.2464 -0.0071 0.066 Uiso 1 1 calc R . . C6 C 0.8146(5) 1.0737(4) 0.0221(3) 0.0463(12) Uani 1 1 d . . . H6 H 0.8955 1.0646 -0.0131 0.060 Uiso 1 1 calc R . . C7 C 0.7688(5) 0.9776(4) 0.0708(2) 0.0385(11) Uani 1 1 d . . . H7 H 0.8205 0.9048 0.0689 0.050 Uiso 1 1 calc R . . C8 C 0.5406(5) 0.9202(4) 0.2562(3) 0.0362(10) Uani 1 1 d . . . C9 C 0.2884(5) 0.8762(4) 0.2233(3) 0.0502(13) Uani 1 1 d . . . H9A H 0.2569 0.9413 0.1869 0.065 Uiso 1 1 calc R . . H9B H 0.2027 0.8494 0.2546 0.065 Uiso 1 1 calc R . . C10 C 0.3444(5) 0.7730(4) 0.1715(3) 0.0369(10) Uani 1 1 d . . . H10 H 0.3882 0.7105 0.2070 0.048 Uiso 1 1 calc R . . C11 C 0.2220(5) 0.7195(5) 0.1191(3) 0.0522(13) Uani 1 1 d . . . H11A H 0.1824 0.7809 0.0832 0.073 Uiso 1 1 calc R . . H11B H 0.1448 0.6894 0.1545 0.073 Uiso 1 1 calc R . . H11C H 0.2610 0.6543 0.0863 0.073 Uiso 1 1 calc R . . C12 C 0.6514(4) 0.6944(4) 0.1152(2) 0.0326(10) Uani 1 1 d . . . C13 C 0.6893(4) 0.7726(4) 0.1738(2) 0.0306(10) Uani 1 1 d . . . C14 C 0.7259(5) 0.5863(4) 0.0814(3) 0.0352(10) Uani 1 1 d . . . C15 C 0.9490(5) 0.4744(4) 0.0883(3) 0.0504(13) Uani 1 1 d . . . H15A H 0.8928 0.4006 0.0900 0.071 Uiso 1 1 calc R . . H15B H 1.0349 0.4667 0.1230 0.071 Uiso 1 1 calc R . . H15C H 0.9794 0.4903 0.0322 0.071 Uiso 1 1 calc R . . C16 C 0.8203(5) 0.7640(4) 0.2312(3) 0.0344(10) Uani 1 1 d . . . C17 C 0.9281(6) 0.6501(5) 0.3387(3) 0.0593(15) Uani 1 1 d . . . H17A H 1.0078 0.6177 0.3060 0.083 Uiso 1 1 calc R . . H17B H 0.9002 0.5924 0.3804 0.083 Uiso 1 1 calc R . . H17C H 0.9598 0.7238 0.3648 0.083 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 O3 0.0262(14) 0.0546(18) 0.0329(14) -0.0111(15) 0.0005(14) 0.0030(15) N1 0.0259(16) 0.0416(19) 0.0307(16) -0.0065(16) 0.0003(16) 0.0006(17) O5 0.0336(16) 0.0434(17) 0.0589(19) -0.0174(17) -0.0019(17) 0.0080(15) O2 0.0367(17) 0.068(2) 0.0502(19) -0.0199(18) 0.0130(16) -0.0016(17) O4 0.0449(18) 0.0504(18) 0.058(2) -0.0204(18) -0.0013(18) -0.0021(17) O7 0.0400(17) 0.0468(17) 0.0463(17) 0.0123(16) -0.0176(16) -0.0054(15) O6 0.0300(16) 0.056(2) 0.065(2) 0.0095(19) -0.0084(16) -0.0107(16) O1 0.046(2) 0.090(3) 0.0380(17) -0.0202(19) -0.0080(17) 0.004(2) C1 0.022(2) 0.033(2) 0.035(2) -0.0035(19) -0.0064(19) 0.0022(19) C2 0.026(2) 0.041(2) 0.028(2) -0.0060(19) -0.011(2) 0.002(2) C3 0.043(3) 0.038(2) 0.048(3) -0.007(2) -0.006(2) 0.002(2) C4 0.057(3) 0.031(2) 0.056(3) 0.002(2) -0.013(3) 0.004(2) C5 0.050(3) 0.055(3) 0.048(3) 0.010(3) -0.012(3) -0.018(3) C6 0.037(2) 0.060(3) 0.043(2) 0.009(2) -0.002(2) -0.012(3) C7 0.033(2) 0.043(2) 0.039(2) 0.000(2) -0.002(2) -0.002(2) C8 0.041(3) 0.038(2) 0.031(2) -0.004(2) 0.002(3) 0.005(2) C9 0.030(2) 0.057(3) 0.064(3) -0.013(3) 0.009(3) -0.001(2) C10 0.029(2) 0.041(2) 0.041(2) 0.004(2) 0.002(2) 0.002(2) C11 0.030(2) 0.065(3) 0.061(3) -0.012(3) -0.001(2) -0.014(2) C12 0.024(2) 0.039(2) 0.035(2) 0.004(2) -0.003(2) 0.0008(19) C13 0.023(2) 0.033(2) 0.037(2) 0.000(2) 0.0026(19) -0.0018(19) C14 0.030(2) 0.040(2) 0.036(2) -0.001(2) 0.006(2) -0.004(2) C15 0.043(3) 0.045(3) 0.064(3) -0.010(2) 0.004(3) 0.013(2) C16 0.029(2) 0.034(2) 0.039(2) -0.004(2) -0.005(2) 0.004(2) C17 0.055(3) 0.058(3) 0.065(3) 0.012(3) -0.033(3) 0.002(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 O3 C12 1.375(5) . ? O3 N1 1.473(4) . ? N1 C10 1.467(5) . ? N1 C1 1.511(5) . ? O5 C14 1.337(5) . ? O5 C15 1.447(5) . ? O2 C8 1.334(5) . ? O2 C9 1.446(6) . ? O4 C14 1.182(5) . ? O7 C16 1.328(5) . ? O7 C17 1.449(5) . ? O6 C16 1.199(5) . ? O1 C8 1.199(5) . ? C1 C13 1.510(5) . ? C1 C2 1.524(6) . ? C1 C8 1.526(6) . ? C2 C3 1.381(6) . ? C2 C7 1.382(6) . ? C3 C4 1.372(6) . ? C4 C5 1.385(7) . ? C5 C6 1.365(7) . ? C6 C7 1.384(6) . ? C9 C10 1.499(6) . ? C10 C11 1.510(6) . ? C12 C13 1.325(5) . ? C12 C14 1.474(6) . ? C13 C16 1.503(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 C12 O3 N1 106.5(3) . . ? C10 N1 O3 106.1(3) . . ? C10 N1 C1 112.1(3) . . ? O3 N1 C1 104.0(3) . . ? C14 O5 C15 116.2(3) . . ? C8 O2 C9 118.2(4) . . ? C16 O7 C17 115.6(3) . . ? C13 C1 N1 101.8(3) . . ? C13 C1 C2 114.3(3) . . ? N1 C1 C2 107.9(3) . . ? C13 C1 C8 110.4(3) . . ? N1 C1 C8 113.8(3) . . ? C2 C1 C8 108.6(3) . . ? C3 C2 C7 117.9(4) . . ? C3 C2 C1 120.4(4) . . ? C7 C2 C1 121.4(4) . . ? C4 C3 C2 121.6(4) . . ? C3 C4 C5 119.6(4) . . ? C6 C5 C4 119.7(4) . . ? C5 C6 C7 120.2(4) . . ? C2 C7 C6 120.9(4) . . ? O1 C8 O2 117.9(4) . . ? O1 C8 C1 120.6(4) . . ? O2 C8 C1 121.5(4) . . ? O2 C9 C10 112.6(4) . . ? N1 C10 C9 104.0(3) . . ? N1 C10 C11 110.7(3) . . ? C9 C10 C11 111.2(4) . . ? C13 C12 O3 113.4(4) . . ? C13 C12 C14 132.3(4) . . ? O3 C12 C14 113.9(3) . . ? C12 C13 C16 126.9(4) . . ? C12 C13 C1 108.2(3) . . ? C16 C13 C1 124.7(3) . . ? O4 C14 O5 125.4(4) . . ? O4 C14 C12 125.4(4) . . ? O5 C14 C12 109.3(4) . . ? O6 C16 O7 125.5(4) . . ? O6 C16 C13 123.7(4) . . ? O7 C16 C13 110.8(4) . . ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.829 _refine_diff_density_max 0.254 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.061 data_jf5 _database_code_CSD 168303 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N O8' _chemical_formula_weight 325.27 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y-1/2, -z' _cell_length_a 9.917(2) _cell_length_b 11.620(3) _cell_length_c 13.983(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.40(2) _cell_angle_gamma 90.00 _cell_volume 1537.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9838 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2094 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 21.97 _reflns_number_total 1880 _reflns_number_gt 1231 _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^)+(0.0569P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1880 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O8 O 0.01038(19) 0.01773(14) 0.36906(13) 0.0454(5) Uani 1 1 d . . . N1 N -0.1041(2) 0.32089(18) 0.16345(15) 0.0383(6) Uani 1 1 d . . . O1 O -0.3303(2) 0.07919(18) 0.09242(14) 0.0550(6) Uani 1 1 d . . . O6 O 0.25903(19) 0.14637(17) 0.36589(13) 0.0530(6) Uani 1 1 d . . . O5 O 0.1765(2) 0.25194(17) 0.47015(14) 0.0566(6) Uani 1 1 d . . . O3 O 0.1965(2) 0.45850(17) 0.33601(14) 0.0585(6) Uani 1 1 d . . . O4 O 0.0093(2) 0.54097(17) 0.22735(15) 0.0603(6) Uani 1 1 d . . . O2 O -0.3124(2) 0.22897(19) 0.00077(14) 0.0665(7) Uani 1 1 d . . . O7 O -0.0691(2) -0.04839(17) 0.21190(14) 0.0603(6) Uani 1 1 d . . . C1 C -0.1411(3) 0.2075(2) 0.16171(18) 0.0375(7) Uani 1 1 d . . . C2 C -0.2663(3) 0.1649(3) 0.08473(19) 0.0463(8) Uani 1 1 d . . . C3 C -0.2223(4) 0.3242(3) -0.0108(2) 0.0647(9) Uani 1 1 d . . . H3A H -0.2725 0.3705 -0.0682 0.084 Uiso 1 1 calc R . . H3B H -0.1382 0.2937 -0.0235 0.084 Uiso 1 1 calc R . . C4 C -0.1800(3) 0.3986(2) 0.08101(19) 0.0481(8) Uani 1 1 d . . . H4 H -0.1141 0.4576 0.0722 0.063 Uiso 1 1 calc R . . C5 C 0.0099(3) 0.3417(2) 0.24615(18) 0.0367(7) Uani 1 1 d . . . C6 C 0.0464(2) 0.2378(2) 0.29623(17) 0.0352(7) Uani 1 1 d . . . C7 C -0.0479(3) 0.1531(2) 0.24355(17) 0.0352(7) Uani 1 1 d . . . C8 C -0.3025(3) 0.4573(3) 0.1051(2) 0.0716(10) Uani 1 1 d . . . H8A H -0.3670 0.4002 0.1150 0.100 Uiso 1 1 calc R . . H8B H -0.3506 0.5067 0.0506 0.100 Uiso 1 1 calc R . . H8C H -0.2674 0.5022 0.1651 0.100 Uiso 1 1 calc R . . C9 C 0.0834(3) 0.4514(3) 0.2743(2) 0.0436(7) Uani 1 1 d . . . C10 C 0.0801(4) 0.6510(3) 0.2459(3) 0.0873(12) Uani 1 1 d . . . H10A H 0.1059 0.6680 0.3162 0.122 Uiso 1 1 calc R . . H10B H 0.0178 0.7097 0.2091 0.122 Uiso 1 1 calc R . . H10C H 0.1635 0.6482 0.2246 0.122 Uiso 1 1 calc R . . C11 C 0.1664(3) 0.2164(2) 0.3880(2) 0.0398(7) Uani 1 1 d . . . C12 C 0.3692(3) 0.1009(3) 0.4507(2) 0.0714(10) Uani 1 1 d . . . H12A H 0.4333 0.1616 0.4813 0.100 Uiso 1 1 calc R . . H12B H 0.4198 0.0415 0.4281 0.100 Uiso 1 1 calc R . . H12C H 0.3275 0.0696 0.4987 0.100 Uiso 1 1 calc R . . C13 C -0.0405(3) 0.0304(2) 0.27049(19) 0.0394(7) Uani 1 1 d . . . C14 C 0.0339(4) -0.0985(3) 0.4069(2) 0.0716(10) Uani 1 1 d . . . H14A H -0.0543 -0.1393 0.3893 0.100 Uiso 1 1 calc R . . H14B H 0.0734 -0.0968 0.4785 0.100 Uiso 1 1 calc R . . H14C H 0.0982 -0.1367 0.3780 0.100 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 O8 0.0587(12) 0.0367(11) 0.0370(11) 0.0036(9) 0.0084(9) 0.0044(9) N1 0.0330(13) 0.0433(15) 0.0343(13) 0.0072(11) 0.0033(11) 0.0034(11) O1 0.0454(13) 0.0646(15) 0.0485(12) -0.0049(10) 0.0044(10) -0.0123(11) O6 0.0372(11) 0.0743(14) 0.0436(11) 0.0111(10) 0.0061(9) 0.0147(11) O5 0.0610(14) 0.0633(14) 0.0358(11) -0.0068(10) -0.0004(10) -0.0012(11) O3 0.0556(13) 0.0549(13) 0.0560(13) 0.0005(11) 0.0028(11) -0.0106(12) O4 0.0697(14) 0.0392(12) 0.0676(14) 0.0033(11) 0.0139(11) 0.0047(12) O2 0.0574(14) 0.0791(16) 0.0442(13) 0.0129(12) -0.0132(11) -0.0090(12) O7 0.0778(16) 0.0478(13) 0.0452(12) -0.0110(11) 0.0028(11) -0.0032(12) C1 0.0345(16) 0.0458(19) 0.0309(15) 0.0020(13) 0.0079(13) -0.0008(14) C2 0.0404(18) 0.059(2) 0.0326(17) 0.0008(16) 0.0010(14) 0.0044(17) C3 0.068(2) 0.074(2) 0.0414(18) 0.0144(17) -0.0010(16) -0.0041(19) C4 0.0391(17) 0.0579(18) 0.0407(17) 0.0173(15) 0.0020(14) 0.0061(15) C5 0.0322(15) 0.0417(17) 0.0349(15) -0.0019(14) 0.0078(13) 0.0007(14) C6 0.0301(16) 0.0401(16) 0.0323(14) 0.0008(13) 0.0047(12) 0.0014(13) C7 0.0356(16) 0.0378(17) 0.0316(15) -0.0004(13) 0.0092(13) 0.0004(13) C8 0.054(2) 0.078(2) 0.082(2) 0.026(2) 0.0184(18) 0.0220(19) C9 0.0490(19) 0.0439(19) 0.0394(17) 0.0008(15) 0.0155(15) 0.0036(17) C10 0.128(3) 0.042(2) 0.085(3) 0.0017(19) 0.021(2) -0.010(2) C11 0.0347(16) 0.0430(17) 0.0387(17) 0.0024(14) 0.0064(14) -0.0031(15) C12 0.0440(19) 0.099(3) 0.061(2) 0.026(2) -0.0008(17) 0.0263(18) C13 0.0339(15) 0.0486(19) 0.0328(16) -0.0014(15) 0.0054(13) -0.0011(14) C14 0.108(3) 0.0437(19) 0.056(2) 0.0126(16) 0.014(2) 0.0112(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 O8 C13 1.327(3) . ? O8 C14 1.444(3) . ? N1 C1 1.366(3) . ? N1 C5 1.376(3) . ? N1 C4 1.480(3) . ? O1 C2 1.203(3) . ? O6 C11 1.331(3) . ? O6 C12 1.450(3) . ? O5 C11 1.196(3) . ? O3 C9 1.196(3) . ? O4 C9 1.328(3) . ? O4 C10 1.444(3) . ? O2 C2 1.349(3) . ? O2 C3 1.462(3) . ? O7 C13 1.204(3) . ? C1 C7 1.390(3) . ? C1 C2 1.465(4) . ? C3 C4 1.500(4) . ? C4 C8 1.516(4) . ? C5 C6 1.388(3) . ? C5 C9 1.463(4) . ? C6 C7 1.404(3) . ? C6 C11 1.488(3) . ? C7 C13 1.471(4) . ? 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 O8 C14 117.0(2) . . ? C1 N1 C5 109.5(2) . . ? C1 N1 C4 120.2(2) . . ? C5 N1 C4 130.3(2) . . ? C11 O6 C12 115.8(2) . . ? C9 O4 C10 115.9(2) . . ? C2 O2 C3 117.1(2) . . ? N1 C1 C7 108.4(2) . . ? N1 C1 C2 120.2(2) . . ? C7 C1 C2 131.3(3) . . ? O1 C2 O2 118.9(3) . . ? O1 C2 C1 124.6(3) . . ? O2 C2 C1 116.4(3) . . ? O2 C3 C4 111.4(2) . . ? N1 C4 C3 105.2(2) . . ? N1 C4 C8 110.8(2) . . ? C3 C4 C8 114.3(3) . . ? N1 C5 C6 107.2(2) . . ? N1 C5 C9 126.6(2) . . ? C6 C5 C9 126.1(2) . . ? C5 C6 C7 108.2(2) . . ? C5 C6 C11 127.0(2) . . ? C7 C6 C11 124.8(2) . . ? C1 C7 C6 106.7(2) . . ? C1 C7 C13 128.4(2) . . ? C6 C7 C13 124.8(2) . . ? O3 C9 O4 124.3(3) . . ? O3 C9 C5 122.5(3) . . ? O4 C9 C5 113.1(2) . . ? O5 C11 O6 124.7(2) . . ? O5 C11 C6 125.9(3) . . ? O6 C11 C6 109.3(2) . . ? O7 C13 O8 124.2(3) . . ? O7 C13 C7 125.4(2) . . ? O8 C13 C7 110.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.137 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.043