Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_or1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.26 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+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 11.858(2) _cell_length_b 7.7841(11) _cell_length_c 13.3660(11) _cell_angle_alpha 90.000(9) _cell_angle_beta 97.595(11) _cell_angle_gamma 90.000(13) _cell_volume 1222.9(3) _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 2519 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.97 _reflns_number_total 2286 _reflns_number_gt 1455 _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^)+(0.0867P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2286 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 O1 O 0.11999(13) -0.20563(19) 0.46049(11) 0.0652(4) Uani 1 1 d . . . O2 O 0.38844(13) 0.1398(2) 0.35388(12) 0.0701(5) Uani 1 1 d . . . O3 O 0.15309(11) 0.25259(16) 0.26734(9) 0.0539(4) Uani 1 1 d . . . N1 N 0.08262(13) 0.2501(2) 0.35141(11) 0.0483(4) Uani 1 1 d . . . N2 N 0.27411(13) -0.0546(2) 0.42117(12) 0.0528(4) Uani 1 1 d . . . C1 C -0.08440(17) 0.1154(2) 0.24061(14) 0.0526(5) Uani 1 1 d . . . C2 C -0.0708(2) 0.0894(3) 0.14027(16) 0.0743(7) Uani 1 1 d . . . H2 H -0.0010 0.0528 0.1236 0.097 Uiso 1 1 calc R . . C3 C -0.1604(4) 0.1176(4) 0.0649(2) 0.1027(10) Uani 1 1 d . . . H3 H -0.1504 0.0999 -0.0022 0.133 Uiso 1 1 calc R . . C4 C -0.2633(3) 0.1712(4) 0.0881(3) 0.1038(11) Uani 1 1 d . . . H4 H -0.3230 0.1903 0.0368 0.135 Uiso 1 1 calc R . . C5 C -0.2790(2) 0.1969(3) 0.1866(2) 0.0884(9) Uani 1 1 d . . . H5 H -0.3494 0.2327 0.2024 0.115 Uiso 1 1 calc R . . C6 C -0.18965(19) 0.1693(3) 0.26234(18) 0.0685(6) Uani 1 1 d . . . H6 H -0.2005 0.1874 0.3292 0.089 Uiso 1 1 calc R . . C7 C 0.01146(16) 0.0951(2) 0.32593(13) 0.0460(4) Uani 1 1 d . . . H7 H -0.0209 0.0591 0.3864 0.060 Uiso 1 1 calc R . . C8 C 0.02289(18) 0.4133(3) 0.34576(17) 0.0624(6) Uani 1 1 d . . . H8A H -0.0113 0.4334 0.2776 0.087 Uiso 1 1 calc R . . H8B H 0.0757 0.5040 0.3666 0.087 Uiso 1 1 calc R . . H8C H -0.0353 0.4105 0.3894 0.087 Uiso 1 1 calc R . . C9 C 0.10474(15) -0.0320(2) 0.30790(12) 0.0476(5) Uani 1 1 d . . . H9 H 0.0770 -0.1199 0.2581 0.062 Uiso 1 1 calc R . . C10 C 0.19605(17) 0.0822(2) 0.27095(14) 0.0500(5) Uani 1 1 d . . . H10 H 0.2133 0.0451 0.2046 0.065 Uiso 1 1 calc R . . C11 C 0.29910(18) 0.0638(3) 0.35056(15) 0.0532(5) Uani 1 1 d . . . C12 C 0.16236(17) -0.1100(2) 0.40468(14) 0.0500(5) Uani 1 1 d . . . C13 C 0.3555(2) -0.1079(3) 0.50625(18) 0.0755(7) Uani 1 1 d . . . H13A H 0.3605 -0.0213 0.5578 0.106 Uiso 1 1 calc R . . H13B H 0.4288 -0.1233 0.4845 0.106 Uiso 1 1 calc R . . H13C H 0.3311 -0.2142 0.5327 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0728(9) 0.0571(9) 0.0665(9) 0.0176(7) 0.0117(7) -0.0100(7) O2 0.0615(10) 0.0731(11) 0.0780(10) 0.0114(8) 0.0179(8) -0.0082(8) O3 0.0598(8) 0.0439(7) 0.0616(8) 0.0062(6) 0.0214(6) 0.0014(6) N1 0.0521(9) 0.0464(9) 0.0479(8) -0.0084(7) 0.0118(7) -0.0021(7) N2 0.0522(10) 0.0533(10) 0.0542(9) 0.0084(7) 0.0114(7) 0.0033(8) C1 0.0607(12) 0.0464(11) 0.0485(11) 0.0011(8) -0.0004(9) -0.0099(9) C2 0.0969(18) 0.0756(15) 0.0466(11) -0.0008(10) -0.0051(12) -0.0063(14) C3 0.146(3) 0.095(2) 0.0569(15) 0.0063(14) -0.0256(18) -0.016(2) C4 0.119(3) 0.0706(18) 0.103(2) 0.0156(16) -0.057(2) -0.0157(18) C5 0.0651(15) 0.0728(17) 0.117(2) 0.0095(16) -0.0252(16) -0.0075(13) C6 0.0600(13) 0.0692(15) 0.0729(14) 0.0030(11) -0.0036(12) -0.0084(11) C7 0.0530(11) 0.0462(10) 0.0394(9) -0.0003(8) 0.0087(8) -0.0057(9) C8 0.0629(13) 0.0494(12) 0.0750(14) -0.0134(10) 0.0097(11) 0.0016(10) C9 0.0614(12) 0.0408(10) 0.0415(9) -0.0050(8) 0.0098(8) -0.0039(9) C10 0.0629(12) 0.0454(10) 0.0445(10) 0.0009(8) 0.0175(9) 0.0046(9) C11 0.0566(12) 0.0490(11) 0.0574(12) 0.0023(9) 0.0209(10) 0.0030(10) C12 0.0623(12) 0.0382(10) 0.0511(11) 0.0003(8) 0.0135(9) 0.0016(9) C13 0.0649(14) 0.0852(17) 0.0755(15) 0.0248(13) 0.0061(12) 0.0082(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.209(2) . ? O2 C11 1.209(2) . ? O3 C10 1.419(2) . ? O3 N1 1.4864(19) . ? N1 C8 1.452(2) . ? N1 C7 1.486(2) . ? N2 C11 1.379(3) . ? N2 C12 1.383(3) . ? N2 C13 1.451(3) . ? C1 C6 1.383(3) . ? C1 C2 1.387(3) . ? C1 C7 1.508(3) . ? C2 C3 1.381(4) . ? C3 C4 1.363(5) . ? C4 C5 1.369(5) . ? C5 C6 1.383(3) . ? C7 C9 1.527(3) . ? C9 C12 1.508(3) . ? C9 C10 1.532(3) . ? C10 C11 1.517(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 C10 O3 N1 101.38(12) . . ? C8 N1 C7 116.12(15) . . ? C8 N1 O3 105.58(14) . . ? C7 N1 O3 101.32(12) . . ? C11 N2 C12 112.80(17) . . ? C11 N2 C13 123.12(18) . . ? C12 N2 C13 124.01(17) . . ? C6 C1 C2 118.07(19) . . ? C6 C1 C7 118.92(17) . . ? C2 C1 C7 122.94(19) . . ? C3 C2 C1 120.4(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C5 120.2(3) . . ? C4 C5 C6 119.6(3) . . ? C5 C6 C1 121.3(2) . . ? N1 C7 C1 115.90(15) . . ? N1 C7 C9 99.27(14) . . ? C1 C7 C9 115.96(15) . . ? C12 C9 C7 112.40(14) . . ? C12 C9 C10 104.52(15) . . ? C7 C9 C10 103.45(14) . . ? O3 C10 C11 111.36(15) . . ? O3 C10 C9 106.70(14) . . ? C11 C10 C9 104.89(14) . . ? O2 C11 N2 124.6(2) . . ? O2 C11 C10 126.87(18) . . ? N2 C11 C10 108.49(17) . . ? O1 C12 N2 124.14(18) . . ? O1 C12 C9 126.79(19) . . ? N2 C12 C9 109.07(16) . . ? _diffrn_measured_fraction_theta_max 0.777 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.777 _refine_diff_density_max 0.209 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.090 data_cb2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N4 O7' _chemical_formula_weight 484.50 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, -y, -z' _cell_length_a 10.628(5) _cell_length_b 11.108(3) _cell_length_c 11.442(5) _cell_angle_alpha 71.62(3) _cell_angle_beta 74.82(4) _cell_angle_gamma 85.00(3) _cell_volume 1237.1(9) _cell_formula_units_Z 2 _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 5872 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.97 _reflns_number_total 5418 _reflns_number_gt 2569 _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^)+(0.1602P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5418 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.0836 _refine_ls_wR_factor_ref 0.2502 _refine_ls_wR_factor_gt 0.2190 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 N1 N 0.3883(2) 0.4800(2) 0.2001(3) 0.0452(6) Uani 1 1 d . . . N2 N 0.1658(2) 0.2862(2) 0.2461(3) 0.0468(7) Uani 1 1 d . . . N3 N 0.5848(2) 0.3747(2) 0.2059(2) 0.0453(6) Uani 1 1 d . . . N4 N 0.5979(2) 0.1502(2) 0.2751(3) 0.0476(7) Uani 1 1 d . . . O1 O 0.7769(2) 0.2786(2) 0.2124(3) 0.0628(7) Uani 1 1 d . . . O2 O 0.4163(2) 0.0290(2) 0.3435(3) 0.0640(7) Uani 1 1 d . . . O3 O 0.3565(3) 0.3226(3) 0.5297(3) 0.0816(9) Uani 1 1 d . . . O4 O 0.1948(2) 0.4609(2) 0.5563(2) 0.0651(7) Uani 1 1 d . . . O5 O 0.0533(2) 0.3604(2) 0.2971(2) 0.0592(6) Uani 1 1 d . . . O6 O 0.2229(3) 0.2222(3) -0.0306(3) 0.0929(10) Uani 1 1 d . . . O7 O 0.0374(3) 0.3148(3) -0.0664(3) 0.0903(10) Uani 1 1 d . . . C1 C 0.4636(3) 0.5976(3) 0.1641(4) 0.0605(10) Uani 1 1 d . . . H1A H 0.5172 0.6133 0.0780 0.079 Uiso 1 1 calc R . . H1B H 0.5213 0.5862 0.2200 0.079 Uiso 1 1 calc R . . C2 C 0.3773(3) 0.7113(3) 0.1718(4) 0.0526(8) Uani 1 1 d . . . C3 C 0.3936(4) 0.8196(3) 0.0710(4) 0.0702(11) Uani 1 1 d . . . H3 H 0.4557 0.8207 -0.0037 0.091 Uiso 1 1 calc R . . C4 C 0.3204(5) 0.9273(4) 0.0769(5) 0.0834(13) Uani 1 1 d . . . H4 H 0.3309 0.9987 0.0058 0.108 Uiso 1 1 calc R . . C5 C 0.2328(5) 0.9291(4) 0.1869(5) 0.0790(13) Uani 1 1 d . . . H5 H 0.1865 1.0029 0.1928 0.103 Uiso 1 1 calc R . . C6 C 0.2135(4) 0.8215(4) 0.2888(5) 0.0782(12) Uani 1 1 d . . . H6 H 0.1508 0.8211 0.3629 0.102 Uiso 1 1 calc R . . C7 C 0.2868(4) 0.7129(3) 0.2825(4) 0.0668(10) Uani 1 1 d . . . H7 H 0.2749 0.6409 0.3531 0.087 Uiso 1 1 calc R . . C8 C 0.2865(3) 0.4952(3) 0.1304(3) 0.0480(8) Uani 1 1 d . . . H8A H 0.3209 0.5484 0.0440 0.062 Uiso 1 1 calc R . . H8B H 0.2136 0.5403 0.1692 0.062 Uiso 1 1 calc R . . C9 C 0.2352(3) 0.3739(3) 0.1250(3) 0.0426(7) Uani 1 1 d . . . H9 H 0.3110 0.3277 0.0901 0.055 Uiso 1 1 calc R . . C10 C 0.2405(3) 0.2488(3) 0.3473(3) 0.0431(7) Uani 1 1 d . . . C11 C 0.3871(3) 0.2498(3) 0.2913(3) 0.0399(7) Uani 1 1 d . . . C12 C 0.4545(3) 0.3671(3) 0.2304(3) 0.0414(7) Uani 1 1 d . . . C13 C 0.6471(3) 0.2660(3) 0.2331(3) 0.0458(7) Uani 1 1 d . . . C14 C 0.8517(4) 0.1644(4) 0.2448(5) 0.0875(15) Uani 1 1 d . . . H14A H 0.8178 0.1177 0.3325 0.123 Uiso 1 1 calc R . . H14B H 0.9411 0.1857 0.2311 0.123 Uiso 1 1 calc R . . H14C H 0.8461 0.1135 0.1923 0.123 Uiso 1 1 calc R . . C15 C 0.4689(3) 0.1449(3) 0.3008(3) 0.0422(7) Uani 1 1 d . . . C16 C 0.5015(4) -0.0803(3) 0.3602(5) 0.0766(13) Uani 1 1 d . . . H16A H 0.5487 -0.0868 0.2786 0.107 Uiso 1 1 calc R . . H16B H 0.4505 -0.1555 0.4069 0.107 Uiso 1 1 calc R . . H16C H 0.5618 -0.0714 0.4064 0.107 Uiso 1 1 calc R . . C17 C 0.1834(3) 0.1216(3) 0.4404(3) 0.0588(9) Uani 1 1 d . . . H17A H 0.0911 0.1308 0.4716 0.082 Uiso 1 1 calc R . . H17B H 0.2237 0.0964 0.5104 0.082 Uiso 1 1 calc R . . H17C H 0.1996 0.0581 0.3974 0.082 Uiso 1 1 calc R . . C18 C 0.2582(3) 0.3725(3) 0.5059(3) 0.0534(8) Uani 1 1 d . . . C19 C 0.2564(5) 0.4985(5) 0.6379(5) 0.0889(14) Uani 1 1 d . . . H19A H 0.2778 0.4243 0.7003 0.124 Uiso 1 1 calc R . . H19B H 0.1978 0.5514 0.6798 0.124 Uiso 1 1 calc R . . H19C H 0.3346 0.5446 0.5877 0.124 Uiso 1 1 calc R . . C20 C 0.1957(3) 0.3486(3) 0.4160(3) 0.0468(8) Uani 1 1 d . . . C21 C 0.1494(3) 0.4064(3) 0.0319(3) 0.0524(8) Uani 1 1 d . . . H21A H 0.0617 0.4239 0.0754 0.068 Uiso 1 1 calc R . . H21B H 0.1820 0.4829 -0.0361 0.068 Uiso 1 1 calc R . . C22 C 0.1444(4) 0.3038(3) -0.0238(3) 0.0584(9) Uani 1 1 d . . . C23 C 0.0220(7) 0.2232(6) -0.1259(8) 0.150(3) Uani 1 1 d . . . H23A H 0.0754 0.2462 -0.2114 0.210 Uiso 1 1 calc R . . H23B H -0.0677 0.2209 -0.1272 0.210 Uiso 1 1 calc R . . H23C H 0.0479 0.1410 -0.0790 0.210 Uiso 1 1 calc R . . C24 C 0.0869(3) 0.3999(3) 0.3856(3) 0.0546(9) Uani 1 1 d . . . H24 H 0.0376 0.4583 0.4219 0.071 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 N1 0.0455(15) 0.0321(13) 0.0582(16) -0.0100(12) -0.0184(12) 0.0033(11) N2 0.0386(14) 0.0474(15) 0.0538(16) -0.0153(12) -0.0127(12) 0.0068(11) N3 0.0428(14) 0.0376(13) 0.0529(16) -0.0082(11) -0.0148(12) 0.0025(11) N4 0.0435(15) 0.0393(14) 0.0603(17) -0.0112(12) -0.0207(13) 0.0083(11) O1 0.0393(12) 0.0476(13) 0.0917(19) -0.0085(12) -0.0168(12) 0.0058(10) O2 0.0513(14) 0.0329(12) 0.108(2) -0.0144(12) -0.0311(13) 0.0077(10) O3 0.0819(19) 0.098(2) 0.091(2) -0.0523(17) -0.0521(16) 0.0501(17) O4 0.0617(15) 0.0819(18) 0.0691(16) -0.0448(14) -0.0268(12) 0.0244(13) O5 0.0410(12) 0.0732(16) 0.0691(16) -0.0303(13) -0.0180(11) 0.0157(11) O6 0.130(3) 0.0647(18) 0.116(3) -0.0514(18) -0.069(2) 0.0379(18) O7 0.086(2) 0.091(2) 0.123(3) -0.0418(19) -0.063(2) -0.0012(16) C1 0.0493(19) 0.0369(17) 0.090(3) -0.0133(17) -0.0170(18) 0.0021(14) C2 0.055(2) 0.0362(17) 0.074(2) -0.0187(16) -0.0276(18) 0.0024(14) C3 0.078(3) 0.043(2) 0.082(3) -0.0122(19) -0.019(2) 0.0062(18) C4 0.107(4) 0.042(2) 0.102(4) -0.012(2) -0.042(3) 0.013(2) C5 0.093(3) 0.049(2) 0.116(4) -0.038(3) -0.052(3) 0.024(2) C6 0.073(3) 0.078(3) 0.102(3) -0.052(3) -0.026(2) 0.008(2) C7 0.081(3) 0.048(2) 0.073(3) -0.0176(19) -0.024(2) 0.0056(18) C8 0.0500(18) 0.0379(16) 0.055(2) -0.0111(14) -0.0170(15) 0.0056(13) C9 0.0457(17) 0.0389(15) 0.0471(18) -0.0149(13) -0.0190(14) 0.0088(13) C10 0.0407(16) 0.0419(16) 0.0440(17) -0.0075(13) -0.0133(13) 0.0012(13) C11 0.0417(16) 0.0354(15) 0.0415(16) -0.0103(13) -0.0111(13) 0.0033(12) C12 0.0465(17) 0.0378(16) 0.0427(17) -0.0136(13) -0.0164(13) 0.0067(13) C13 0.0438(17) 0.0432(17) 0.0496(18) -0.0113(14) -0.0158(14) 0.0064(13) C14 0.047(2) 0.059(2) 0.141(4) -0.005(2) -0.031(2) 0.0112(18) C15 0.0461(17) 0.0350(15) 0.0474(18) -0.0079(13) -0.0220(14) 0.0044(13) C16 0.069(3) 0.0339(17) 0.132(4) -0.017(2) -0.047(3) 0.0123(17) C17 0.055(2) 0.052(2) 0.057(2) -0.0036(16) -0.0062(16) -0.0022(16) C18 0.056(2) 0.057(2) 0.0464(19) -0.0185(16) -0.0119(16) 0.0122(16) C19 0.094(3) 0.114(4) 0.089(3) -0.066(3) -0.038(3) 0.021(3) C20 0.0452(18) 0.0485(18) 0.0442(18) -0.0154(14) -0.0082(14) 0.0087(14) C21 0.064(2) 0.0468(18) 0.0512(19) -0.0139(15) -0.0264(16) 0.0080(16) C22 0.074(2) 0.0447(19) 0.055(2) -0.0040(16) -0.0270(18) -0.0018(17) C23 0.202(7) 0.125(5) 0.187(7) -0.071(5) -0.123(6) -0.013(5) C24 0.0506(19) 0.066(2) 0.051(2) -0.0298(17) -0.0107(16) 0.0174(16) _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 N1 C12 1.374(4) . ? N1 C8 1.473(4) . ? N1 C1 1.479(4) . ? N2 C9 1.467(4) . ? N2 O5 1.488(3) . ? N2 C10 1.504(4) . ? N3 C13 1.313(4) . ? N3 C12 1.344(4) . ? N4 C13 1.325(4) . ? N4 C15 1.327(4) . ? O1 C13 1.350(4) . ? O1 C14 1.435(4) . ? O2 C15 1.340(4) . ? O2 C16 1.444(4) . ? O3 C18 1.194(4) . ? O4 C18 1.338(4) . ? O4 C19 1.445(5) . ? O5 C24 1.358(4) . ? O6 C22 1.184(4) . ? O7 C22 1.332(5) . ? O7 C23 1.432(6) . ? C1 C2 1.506(4) . ? C2 C3 1.365(5) . ? C2 C7 1.379(5) . ? C3 C4 1.379(5) . ? C4 C5 1.360(7) . ? C5 C6 1.366(7) . ? C6 C7 1.390(5) . ? C8 C9 1.522(4) . ? C9 C21 1.518(4) . ? C10 C11 1.521(4) . ? C10 C20 1.528(4) . ? C10 C17 1.537(4) . ? C11 C15 1.385(4) . ? C11 C12 1.423(4) . ? C18 C20 1.459(5) . ? C20 C24 1.324(4) . ? C21 C22 1.481(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 C12 N1 C8 120.6(2) . . ? C12 N1 C1 117.1(3) . . ? C8 N1 C1 112.3(2) . . ? C9 N2 O5 105.2(2) . . ? C9 N2 C10 114.3(2) . . ? O5 N2 C10 103.8(2) . . ? C13 N3 C12 115.7(3) . . ? C13 N4 C15 115.2(3) . . ? C13 O1 C14 117.1(3) . . ? C15 O2 C16 118.8(3) . . ? C18 O4 C19 115.7(3) . . ? C24 O5 N2 106.9(2) . . ? C22 O7 C23 116.3(4) . . ? N1 C1 C2 112.5(3) . . ? C3 C2 C7 118.0(3) . . ? C3 C2 C1 120.3(4) . . ? C7 C2 C1 121.5(3) . . ? C2 C3 C4 121.8(4) . . ? C5 C4 C3 120.0(4) . . ? C4 C5 C6 119.4(4) . . ? C5 C6 C7 120.5(4) . . ? C2 C7 C6 120.3(4) . . ? N1 C8 C9 116.4(2) . . ? N2 C9 C21 109.4(3) . . ? N2 C9 C8 116.8(3) . . ? C21 C9 C8 109.7(3) . . ? N2 C10 C11 112.1(2) . . ? N2 C10 C20 102.2(2) . . ? C11 C10 C20 112.8(3) . . ? N2 C10 C17 106.2(3) . . ? C11 C10 C17 115.6(3) . . ? C20 C10 C17 106.7(3) . . ? C15 C11 C12 113.4(3) . . ? C15 C11 C10 126.4(3) . . ? C12 C11 C10 120.1(2) . . ? N3 C12 N1 116.3(3) . . ? N3 C12 C11 122.3(3) . . ? N1 C12 C11 121.3(3) . . ? N3 C13 N4 127.9(3) . . ? N3 C13 O1 113.6(3) . . ? N4 C13 O1 118.5(3) . . ? N4 C15 O2 116.6(3) . . ? N4 C15 C11 124.4(3) . . ? O2 C15 C11 118.9(3) . . ? O3 C18 O4 123.2(3) . . ? O3 C18 C20 124.7(3) . . ? O4 C18 C20 112.1(3) . . ? C24 C20 C18 127.8(3) . . ? C24 C20 C10 107.2(3) . . ? C18 C20 C10 124.9(3) . . ? C22 C21 C9 113.1(3) . . ? O6 C22 O7 123.5(4) . . ? O6 C22 C21 126.0(4) . . ? O7 C22 C21 110.5(3) . . ? C20 C24 O5 114.5(3) . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.393 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.088