# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number:207/444 data_s92 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N2 O3' _chemical_formula_weight 284.31 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 7.1760(10) _cell_length_b 17.805(4) _cell_length_c 20.947(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2676.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16412 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _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 16412 _diffrn_reflns_av_R_equivalents 0.1168 _diffrn_reflns_av_sigmaI/netI 0.1167 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3062 _reflns_number_gt 1594 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3062 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _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 0.7079(2) -0.06148(9) 0.89174(8) 0.0294(5) Uani 1 1 d . . . O2 O 0.5439(2) 0.11100(10) 0.71227(9) 0.0310(5) Uani 1 1 d . . . O3 O 0.6570(2) 0.01289(10) 0.65741(8) 0.0303(5) Uani 1 1 d . . . N1 N 0.8375(3) -0.24328(12) 0.73077(10) 0.0238(5) Uani 1 1 d . . . H1 H 0.8796 -0.2861 0.7431 0.029 Uiso 1 1 calc R . . N2 N 0.7362(3) -0.12630(11) 0.73507(10) 0.0218(5) Uani 1 1 d . . . C1 C 0.8179(3) -0.30694(14) 0.87865(12) 0.0239(6) Uani 1 1 d . . . H1A H 0.7649 -0.3259 0.8415 0.029 Uiso 1 1 calc R . . C2 C 0.8766(3) -0.35619(15) 0.92605(13) 0.0282(6) Uani 1 1 d . . . H2 H 0.8631 -0.4077 0.9202 0.034 Uiso 1 1 calc R . . C3 C 0.9549(3) -0.32919(15) 0.98181(13) 0.0284(6) Uani 1 1 d . . . H3 H 0.9954 -0.3622 1.0133 0.034 Uiso 1 1 calc R . . C4 C 0.9723(3) -0.25274(15) 0.99027(12) 0.0253(6) Uani 1 1 d . . . H4 H 1.0246 -0.2343 1.0277 0.030 Uiso 1 1 calc R . . C5 C 0.9130(3) -0.20321(15) 0.94371(12) 0.0233(6) Uani 1 1 d . . . H5 H 0.9233 -0.1518 0.9506 0.028 Uiso 1 1 calc R . . C6 C 0.8372(3) -0.22969(13) 0.88596(12) 0.0204(6) Uani 1 1 d . . . C7 C 0.7863(3) -0.17621(13) 0.83581(12) 0.0198(6) Uani 1 1 d . . . C8 C 0.7904(3) -0.18838(13) 0.77010(12) 0.0205(6) Uani 1 1 d . . . C9 C 0.8096(3) -0.22268(14) 0.66359(12) 0.0243(6) Uani 1 1 d . . . H9A H 0.7089 -0.2515 0.6448 0.029 Uiso 1 1 calc R . . H9B H 0.9223 -0.2309 0.6390 0.029 Uiso 1 1 calc R . . C10 C 0.7605(3) -0.13912(13) 0.66624(11) 0.0209(6) Uani 1 1 d . . . H10A H 0.8604 -0.1085 0.6491 0.025 Uiso 1 1 calc R . . H10B H 0.6465 -0.1286 0.6430 0.025 Uiso 1 1 calc R . . C11 C 0.6990(3) -0.06748(13) 0.77600(11) 0.0185(6) Uani 1 1 d . . . C12 C 0.7309(3) -0.09991(14) 0.84293(12) 0.0216(6) Uani 1 1 d . . . C13 C 0.6435(3) 0.00391(14) 0.76862(12) 0.0227(6) Uani 1 1 d . . . H13 H 0.6237 0.0297 0.8066 0.027 Uiso 1 1 calc R . . C14 C 0.6089(3) 0.04789(15) 0.71115(12) 0.0231(6) Uani 1 1 d . . . C15 C 0.6336(4) 0.05382(15) 0.59785(13) 0.0344(7) Uani 1 1 d . . . H15A H 0.6934 0.1026 0.6005 0.041 Uiso 1 1 calc R . . H15B H 0.5023 0.0613 0.5889 0.041 Uiso 1 1 calc R . . C16 C 0.7220(4) 0.00747(16) 0.54650(13) 0.0357(7) Uani 1 1 d . . . H16A H 0.8497 -0.0022 0.5574 0.054 Uiso 1 1 calc R . . H16B H 0.7167 0.0342 0.5067 0.054 Uiso 1 1 calc R . . H16C H 0.6564 -0.0393 0.5425 0.054 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 0.0403(10) 0.0282(11) 0.0196(11) -0.0030(9) -0.0005(8) 0.0042(8) O2 0.0369(10) 0.0183(11) 0.0377(12) 0.0000(9) -0.0050(8) 0.0027(8) O3 0.0409(10) 0.0262(11) 0.0238(11) 0.0036(9) -0.0004(8) 0.0067(8) N1 0.0285(11) 0.0207(12) 0.0223(12) -0.0006(10) -0.0014(8) 0.0049(9) N2 0.0292(11) 0.0185(11) 0.0177(12) -0.0014(10) -0.0007(9) 0.0014(8) C1 0.0223(12) 0.0270(16) 0.0224(15) 0.0010(12) -0.0026(10) -0.0004(10) C2 0.0272(13) 0.0239(15) 0.0336(17) 0.0047(13) 0.0020(11) 0.0016(10) C3 0.0275(14) 0.0333(17) 0.0243(16) 0.0090(13) -0.0033(11) 0.0036(11) C4 0.0225(13) 0.0321(16) 0.0214(15) 0.0005(13) -0.0018(10) -0.0003(10) C5 0.0189(11) 0.0238(14) 0.0271(16) 0.0005(12) 0.0038(10) -0.0028(10) C6 0.0146(11) 0.0231(14) 0.0236(15) 0.0013(12) 0.0022(9) -0.0008(9) C7 0.0197(11) 0.0212(14) 0.0184(14) -0.0015(11) -0.0009(10) -0.0012(9) C8 0.0154(12) 0.0203(15) 0.0257(15) 0.0010(12) -0.0006(10) -0.0019(9) C9 0.0233(12) 0.0283(16) 0.0212(15) -0.0004(12) -0.0024(10) 0.0006(10) C10 0.0210(12) 0.0242(15) 0.0177(14) -0.0013(11) 0.0008(10) -0.0013(9) C11 0.0164(11) 0.0203(14) 0.0188(14) -0.0013(11) 0.0001(9) -0.0016(9) C12 0.0184(11) 0.0269(15) 0.0194(15) -0.0029(12) 0.0004(10) -0.0032(10) C13 0.0229(13) 0.0239(15) 0.0212(15) -0.0022(12) -0.0006(10) -0.0011(10) C14 0.0226(12) 0.0204(15) 0.0262(16) -0.0019(12) -0.0017(10) -0.0046(10) C15 0.0440(15) 0.0342(18) 0.0251(17) 0.0076(14) -0.0041(12) 0.0051(12) C16 0.0484(16) 0.0362(18) 0.0225(16) 0.0061(14) 0.0006(12) -0.0032(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 1.241(3) . ? O2 C14 1.217(3) . ? O3 C14 1.332(3) . ? O3 C15 1.455(3) . ? N1 C8 1.322(3) . ? N1 C9 1.468(3) . ? N2 C11 1.379(3) . ? N2 C8 1.383(3) . ? N2 C10 1.470(3) . ? C1 C2 1.390(3) . ? C1 C6 1.391(3) . ? C2 C3 1.383(4) . ? C3 C4 1.378(4) . ? C4 C5 1.382(3) . ? C5 C6 1.407(3) . ? C6 C7 1.464(3) . ? C7 C8 1.394(3) . ? C7 C12 1.423(3) . ? C9 C10 1.530(3) . ? C11 C13 1.341(3) . ? C11 C12 1.534(3) . ? C13 C14 1.457(3) . ? C15 C16 1.497(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 C14 O3 C15 117.42(19) . . ? C8 N1 C9 112.2(2) . . ? C11 N2 C8 109.4(2) . . ? C11 N2 C10 138.6(2) . . ? C8 N2 C10 111.27(19) . . ? C2 C1 C6 121.0(2) . . ? C3 C2 C1 120.5(3) . . ? C4 C3 C2 119.3(2) . . ? C3 C4 C5 120.8(2) . . ? C4 C5 C6 120.8(2) . . ? C1 C6 C5 117.7(2) . . ? C1 C6 C7 122.6(2) . . ? C5 C6 C7 119.7(2) . . ? C8 C7 C12 105.0(2) . . ? C8 C7 C6 127.0(2) . . ? C12 C7 C6 128.0(2) . . ? N1 C8 N2 109.4(2) . . ? N1 C8 C7 137.4(2) . . ? N2 C8 C7 113.2(2) . . ? N1 C9 C10 103.86(19) . . ? N2 C10 C9 102.35(19) . . ? C13 C11 N2 134.9(2) . . ? C13 C11 C12 120.4(2) . . ? N2 C11 C12 104.7(2) . . ? O1 C12 C7 130.5(2) . . ? O1 C12 C11 121.7(2) . . ? C7 C12 C11 107.8(2) . . ? C11 C13 C14 130.9(2) . . ? O2 C14 O3 123.2(2) . . ? O2 C14 C13 123.1(2) . . ? O3 C14 C13 113.7(2) . . ? O3 C15 C16 106.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.068 data_s92-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O' _chemical_formula_weight 266.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.831(2) _cell_length_b 11.534(2) _cell_length_c 13.182(3) _cell_angle_alpha 90.34(3) _cell_angle_beta 92.49(3) _cell_angle_gamma 90.79(3) _cell_volume 1341.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(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 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _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 21333 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.00 _reflns_number_total 4182 _reflns_number_gt 3035 _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 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4182 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1873 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _refine_ls_shift/su_max 0.328 _refine_ls_shift/su_mean 0.042 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4300(2) 0.03576(14) 0.85569(14) 0.0313(5) Uani 1 d . . . O2 O 0.0475(2) 0.53356(14) 0.86206(14) 0.0313(5) Uani 1 d . . . N1 N 0.2884(3) -0.32631(19) 0.94032(17) 0.0289(6) Uani 1 d . . . H1 H 0.236(3) -0.381(3) 0.921(2) 0.037(9) Uiso 1 d . . . N2 N 0.3676(2) -0.15187(17) 0.88808(16) 0.0248(5) Uani 1 d . . . N3 N 0.1991(3) 0.17049(19) 0.93414(17) 0.0286(6) Uani 1 d . . . H3 H 0.254(4) 0.116(3) 0.910(2) 0.050(10) Uiso 1 d . . . N4 N 0.1129(2) 0.34534(17) 0.88843(16) 0.0253(5) Uani 1 d . . . C1 C 0.2898(3) -0.1269(2) 0.9818(2) 0.0300(7) Uani 1 d . . . H1A H 0.2203 -0.0629 0.9728 0.036 Uiso 1 calc R . . H1B H 0.3614 -0.1092 1.0378 0.036 Uiso 1 calc R . . C2 C 0.2045(3) -0.2418(2) 0.9987(2) 0.0296(7) Uani 1 d . . . H2A H 0.2064 -0.2617 1.0701 0.036 Uiso 1 calc R . . H2B H 0.0999 -0.2375 0.9734 0.036 Uiso 1 calc R . . C3 C 0.3649(3) -0.2672(2) 0.86601(19) 0.0250(6) Uani 1 d . . . C4 C 0.4336(3) -0.3110(2) 0.78305(19) 0.0258(6) Uani 1 d . . . C5 C 0.4281(3) -0.4387(2) 0.76296(19) 0.0261(6) Uani 1 d . . . C6 C 0.5177(3) -0.5140(2) 0.8208(2) 0.0336(7) Uani 1 d . . . H6 H 0.5838 -0.4843 0.8716 0.040 Uiso 1 calc R . . C7 C 0.5101(4) -0.6330(2) 0.8037(2) 0.0373(7) Uani 1 d . . . H7 H 0.5711 -0.6820 0.8429 0.045 Uiso 1 calc R . . C8 C 0.4126(3) -0.6788(2) 0.7289(2) 0.0358(7) Uani 1 d . . . H8 H 0.4075 -0.7585 0.7175 0.043 Uiso 1 calc R . . C9 C 0.3224(3) -0.6048(2) 0.6710(2) 0.0340(7) Uani 1 d . . . H9 H 0.2566 -0.6349 0.6201 0.041 Uiso 1 calc R . . C10 C 0.3299(3) -0.4866(2) 0.68842(19) 0.0299(7) Uani 1 d . . . H10 H 0.2678 -0.4381 0.6494 0.036 Uiso 1 calc R . . C11 C 0.5061(3) -0.2283(2) 0.71922(19) 0.0255(6) Uani 1 d . . . C12 C 0.5077(3) -0.1117(2) 0.74232(19) 0.0261(6) Uani 1 d . . . C13 C 0.4364(3) -0.0686(2) 0.82971(19) 0.0251(6) Uani 1 d . . . C14 C 0.5758(3) -0.0199(2) 0.6755(2) 0.0319(7) Uani 1 d . . . H14A H 0.4945 0.0257 0.6450 0.038 Uiso 1 calc R . . H14B H 0.6396 0.0317 0.7176 0.038 Uiso 1 calc R . . C15 C 0.6690(3) -0.0689(2) 0.5919(2) 0.0352(7) Uani 1 d . . . H15A H 0.6791 -0.0111 0.5394 0.042 Uiso 1 calc R . . H15B H 0.7697 -0.0863 0.6194 0.042 Uiso 1 calc R . . C16 C 0.5972(4) -0.1774(2) 0.5459(2) 0.0376(7) Uani 1 d . . . H16A H 0.6588 -0.2057 0.4921 0.045 Uiso 1 calc R . . H16B H 0.4977 -0.1597 0.5163 0.045 Uiso 1 calc R . . C17 C 0.5819(3) -0.2716(2) 0.6265(2) 0.0319(7) Uani 1 d . . . H17A H 0.5234 -0.3364 0.5973 0.038 Uiso 1 calc R . . H17B H 0.6819 -0.2996 0.6463 0.038 Uiso 1 calc R . . C18 C 0.2058(3) 0.3689(2) 0.9813(2) 0.0306(7) Uani 1 d . . . H18A H 0.1433 0.3875 1.0378 0.037 Uiso 1 calc R . . H18B H 0.2774 0.4320 0.9718 0.037 Uiso 1 calc R . . C19 C 0.2873(3) 0.2537(2) 0.9985(2) 0.0299(7) Uani 1 d . . . H19A H 0.3913 0.2591 0.9780 0.036 Uiso 1 calc R . . H19B H 0.2869 0.2314 1.0693 0.036 Uiso 1 calc R . . C20 C 0.1124(3) 0.2314(2) 0.86221(19) 0.0251(6) Uani 1 d . . . C21 C 0.0348(3) 0.1900(2) 0.77746(19) 0.0259(6) Uani 1 d . . . C22 C 0.0404(3) 0.0634(2) 0.75177(19) 0.0270(6) Uani 1 d . . . C23 C -0.0329(3) -0.0187(2) 0.8101(2) 0.0334(7) Uani 1 d . . . H23 H -0.0893 0.0053 0.8641 0.040 Uiso 1 calc R . . C24 C -0.0223(3) -0.1365(2) 0.7880(2) 0.0378(8) Uani 1 d . . . H24 H -0.0722 -0.1905 0.8272 0.045 Uiso 1 calc R . . C25 C 0.0613(3) -0.1733(2) 0.7087(2) 0.0384(8) Uani 1 d . . . H25 H 0.0688 -0.2521 0.6945 0.046 Uiso 1 calc R . . C26 C 0.1342(3) -0.0926(2) 0.6501(2) 0.0376(7) Uani 1 d . . . H26 H 0.1906 -0.1170 0.5961 0.045 Uiso 1 calc R . . C27 C 0.1232(3) 0.0245(2) 0.6717(2) 0.0313(7) Uani 1 d . . . H27 H 0.1723 0.0781 0.6318 0.038 Uiso 1 calc R . . C28 C -0.0461(3) 0.2738(2) 0.71655(19) 0.0262(6) Uani 1 d . . . C29 C -0.0446(3) 0.3896(2) 0.74343(19) 0.0276(6) Uani 1 d . . . C30 C 0.0371(3) 0.4300(2) 0.83256(19) 0.0255(6) Uani 1 d . . . C31 C -0.1217(3) 0.4821(2) 0.6797(2) 0.0326(7) Uani 1 d . . . H31A H -0.0444 0.5312 0.6513 0.039 Uiso 1 calc R A 1 H31B H -0.1803 0.5302 0.7236 0.039 Uiso 1 calc R A 1 C32 C -0.2260(6) 0.4359(3) 0.5934(3) 0.0446(10) Uani 0.80 d P B 1 H32A H -0.3247 0.4182 0.6194 0.053 Uiso 0.80 calc PR B 1 H32B H -0.2390 0.4955 0.5422 0.053 Uiso 0.80 calc PR B 1 C33 C -0.1659(12) 0.3300(4) 0.5456(5) 0.040(2) Uani 0.74(2) d P B 1 H33A H -0.0738 0.3503 0.5119 0.048 Uiso 0.74(2) calc PR B 1 H33B H -0.2393 0.3015 0.4942 0.048 Uiso 0.74(2) calc PR B 1 C32' C -0.1423(17) 0.4395(10) 0.5675(10) 0.016(3) Uiso 0.20 d P B 2 H32A H -0.0448 0.4280 0.5380 0.019 Uiso 0.20 calc PR B 2 H32B H -0.1994 0.4949 0.5266 0.019 Uiso 0.20 calc PR B 2 C33' C -0.233(3) 0.3197(11) 0.5748(16) 0.031(4) Uiso 0.26(2) d P B 2 H33A H -0.3208 0.3295 0.6160 0.037 Uiso 0.26(2) calc PR B 2 H33B H -0.2690 0.2940 0.5076 0.037 Uiso 0.26(2) calc PR B 2 C34 C -0.1315(3) 0.2336(2) 0.6207(2) 0.0368(7) Uani 1 d . . . H34A H -0.0724 0.1751 0.5878 0.044 Uiso 1 calc R C 1 H34B H -0.2262 0.1974 0.6389 0.044 Uiso 1 calc R C 1 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 0.0338(12) 0.0205(10) 0.0396(12) -0.0016(8) 0.0016(9) 0.0005(8) O2 0.0329(12) 0.0196(10) 0.0410(12) -0.0047(8) -0.0016(9) -0.0006(8) N1 0.0322(14) 0.0217(13) 0.0328(14) 0.0002(10) 0.0030(11) -0.0063(10) N2 0.0254(13) 0.0205(11) 0.0284(13) -0.0008(9) -0.0002(10) -0.0007(9) N3 0.0324(14) 0.0221(12) 0.0310(14) -0.0014(10) -0.0023(10) 0.0053(10) N4 0.0264(13) 0.0221(12) 0.0274(13) -0.0020(9) -0.0003(10) 0.0000(9) C1 0.0329(16) 0.0267(14) 0.0305(16) -0.0026(11) 0.0029(12) 0.0005(11) C2 0.0303(17) 0.0265(15) 0.0322(16) 0.0011(12) 0.0031(12) 0.0007(11) C3 0.0258(15) 0.0211(14) 0.0274(15) -0.0005(11) -0.0055(12) -0.0003(11) C4 0.0254(15) 0.0224(14) 0.0291(15) 0.0000(11) -0.0036(12) 0.0008(11) C5 0.0307(16) 0.0203(13) 0.0276(15) 0.0006(11) 0.0045(12) 0.0005(11) C6 0.0343(17) 0.0278(16) 0.0385(17) 0.0012(12) -0.0031(13) 0.0038(12) C7 0.0447(19) 0.0251(15) 0.0425(18) 0.0068(13) 0.0031(14) 0.0108(13) C8 0.0457(19) 0.0207(15) 0.0417(18) -0.0039(12) 0.0111(15) 0.0004(12) C9 0.0352(17) 0.0305(16) 0.0359(17) -0.0068(12) 0.0005(13) -0.0028(12) C10 0.0322(17) 0.0267(15) 0.0305(16) 0.0000(12) -0.0013(12) 0.0027(11) C11 0.0271(15) 0.0221(14) 0.0271(15) 0.0009(11) -0.0015(11) 0.0026(11) C12 0.0248(15) 0.0227(14) 0.0309(16) 0.0013(11) 0.0002(12) 0.0001(11) C13 0.0246(15) 0.0188(14) 0.0312(16) 0.0000(11) -0.0050(12) 0.0005(10) C14 0.0340(17) 0.0251(15) 0.0368(17) 0.0013(12) 0.0027(13) 0.0000(11) C15 0.0388(18) 0.0291(16) 0.0380(18) 0.0061(12) 0.0053(13) -0.0006(12) C16 0.047(2) 0.0343(16) 0.0317(17) 0.0019(12) 0.0074(14) 0.0037(13) C17 0.0371(18) 0.0245(15) 0.0343(17) -0.0007(12) 0.0025(13) 0.0034(12) C18 0.0335(17) 0.0283(15) 0.0294(16) -0.0049(11) -0.0030(12) -0.0005(11) C19 0.0300(17) 0.0286(15) 0.0309(16) -0.0007(12) -0.0024(12) 0.0010(12) C20 0.0256(15) 0.0203(14) 0.0300(16) 0.0001(11) 0.0068(12) 0.0006(11) C21 0.0279(16) 0.0202(13) 0.0297(16) -0.0029(11) 0.0020(12) -0.0009(11) C22 0.0298(16) 0.0230(14) 0.0275(16) -0.0010(11) -0.0048(12) 0.0010(11) C23 0.0366(17) 0.0286(16) 0.0350(17) 0.0025(12) 0.0015(13) -0.0014(12) C24 0.0433(19) 0.0247(15) 0.0446(19) 0.0085(13) -0.0042(15) -0.0071(13) C25 0.0398(19) 0.0233(15) 0.051(2) -0.0078(13) -0.0106(15) 0.0033(13) C26 0.0379(18) 0.0344(17) 0.0406(18) -0.0100(13) 0.0035(14) 0.0016(13) C27 0.0327(17) 0.0264(15) 0.0346(17) -0.0002(12) 0.0009(13) -0.0021(12) C28 0.0275(16) 0.0226(14) 0.0285(15) 0.0007(11) 0.0041(12) -0.0018(11) C29 0.0273(16) 0.0252(15) 0.0301(16) -0.0004(11) 0.0007(12) 0.0002(11) C30 0.0242(15) 0.0217(14) 0.0308(15) -0.0012(11) 0.0045(12) -0.0012(11) C31 0.0400(18) 0.0219(14) 0.0360(17) 0.0025(12) 0.0009(13) 0.0022(12) C32 0.060(3) 0.035(2) 0.038(2) 0.0023(17) -0.011(2) 0.0033(19) C33 0.050(5) 0.033(2) 0.035(3) -0.0021(19) -0.009(3) 0.001(2) C34 0.0436(19) 0.0285(16) 0.0372(18) -0.0013(13) -0.0083(14) -0.0032(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 C13 1.252(3) . ? O2 C30 1.255(3) . ? N1 C3 1.390(3) . ? N1 C2 1.467(3) . ? N2 C3 1.360(3) . ? N2 C13 1.385(3) . ? N2 C1 1.469(3) . ? N3 C20 1.393(3) . ? N3 C19 1.470(3) . ? N4 C20 1.357(3) . ? N4 C30 1.388(3) . ? N4 C18 1.466(3) . ? C1 C2 1.538(3) . ? C3 C4 1.371(4) . ? C4 C11 1.438(4) . ? C4 C5 1.495(3) . ? C5 C10 1.389(4) . ? C5 C6 1.392(4) . ? C6 C7 1.390(4) . ? C7 C8 1.378(4) . ? C8 C9 1.386(4) . ? C9 C10 1.381(4) . ? C11 C12 1.377(3) . ? C11 C17 1.505(4) . ? C12 C13 1.427(4) . ? C12 C14 1.516(3) . ? C14 C15 1.515(4) . ? C15 C16 1.508(4) . ? C16 C17 1.533(4) . ? C18 C19 1.532(4) . ? C20 C21 1.365(4) . ? C21 C28 1.438(4) . ? C21 C22 1.499(3) . ? C22 C27 1.385(4) . ? C22 C23 1.393(4) . ? C23 C24 1.392(4) . ? C24 C25 1.375(4) . ? C25 C26 1.383(4) . ? C26 C27 1.384(4) . ? C28 C29 1.379(3) . ? C28 C34 1.510(4) . ? C29 C30 1.424(4) . ? C29 C31 1.513(4) . ? C31 C32 1.522(5) . ? C31 C32' 1.559(13) . ? C32 C33 1.486(7) . ? C33 C34 1.518(6) . ? C32' C33' 1.60(2) . ? C33' C34 1.466(14) . ? 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 C3 N1 C2 108.4(2) . . ? C3 N2 C13 124.1(2) . . ? C3 N2 C1 111.6(2) . . ? C13 N2 C1 124.3(2) . . ? C20 N3 C19 108.8(2) . . ? C20 N4 C30 123.9(2) . . ? C20 N4 C18 112.0(2) . . ? C30 N4 C18 124.0(2) . . ? N2 C1 C2 101.7(2) . . ? N1 C2 C1 103.6(2) . . ? N2 C3 C4 121.8(2) . . ? N2 C3 N1 109.3(2) . . ? C4 C3 N1 128.9(2) . . ? C3 C4 C11 116.6(2) . . ? C3 C4 C5 119.5(2) . . ? C11 C4 C5 123.9(2) . . ? C10 C5 C6 117.7(2) . . ? C10 C5 C4 121.3(2) . . ? C6 C5 C4 121.0(2) . . ? C7 C6 C5 121.0(3) . . ? C8 C7 C6 120.4(3) . . ? C7 C8 C9 119.2(2) . . ? C10 C9 C8 120.2(3) . . ? C9 C10 C5 121.4(2) . . ? C12 C11 C4 121.0(2) . . ? C12 C11 C17 120.3(2) . . ? C4 C11 C17 118.7(2) . . ? C11 C12 C13 121.3(2) . . ? C11 C12 C14 123.4(2) . . ? C13 C12 C14 115.2(2) . . ? O1 C13 N2 119.1(2) . . ? O1 C13 C12 125.7(2) . . ? N2 C13 C12 115.2(2) . . ? C15 C14 C12 113.8(2) . . ? C16 C15 C14 111.7(2) . . ? C15 C16 C17 110.8(2) . . ? C11 C17 C16 112.4(2) . . ? N4 C18 C19 102.4(2) . . ? N3 C19 C18 104.1(2) . . ? N4 C20 C21 122.1(2) . . ? N4 C20 N3 109.3(2) . . ? C21 C20 N3 128.6(2) . . ? C20 C21 C28 116.5(2) . . ? C20 C21 C22 119.6(2) . . ? C28 C21 C22 124.0(2) . . ? C27 C22 C23 118.2(2) . . ? C27 C22 C21 120.9(2) . . ? C23 C22 C21 120.9(2) . . ? C24 C23 C22 120.5(3) . . ? C25 C24 C23 120.4(3) . . ? C24 C25 C26 119.6(3) . . ? C25 C26 C27 120.0(3) . . ? C22 C27 C26 121.3(3) . . ? C29 C28 C21 121.1(2) . . ? C29 C28 C34 119.9(2) . . ? C21 C28 C34 118.9(2) . . ? C28 C29 C30 121.0(2) . . ? C28 C29 C31 123.3(2) . . ? C30 C29 C31 115.6(2) . . ? O2 C30 N4 119.0(2) . . ? O2 C30 C29 125.6(2) . . ? N4 C30 C29 115.3(2) . . ? C29 C31 C32 114.6(2) . . ? C29 C31 C32' 109.7(5) . . ? C32 C31 C32' 31.2(5) . . ? C33 C32 C31 112.3(4) . . ? C32 C33 C34 113.4(6) . . ? C31 C32' C33' 104.3(11) . . ? C34 C33' C32' 108.3(13) . . ? C33 C34 C28 113.9(3) . . ? C33 C34 C33' 28.4(7) . . ? C28 C34 C33' 114.7(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.282 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.070 data_s92-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 N2 O4' _chemical_formula_weight 420.49 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0117(5) _cell_length_b 10.6661(8) _cell_length_c 12.2753(9) _cell_angle_alpha 65.331(3) _cell_angle_beta 65.329(4) _cell_angle_gamma 62.908(3) _cell_volume 1119.42(13) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used na _cell_measurement_theta_min na _cell_measurement_theta_max na _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type 'Empirical, SORTAV' _exptl_absorpt_correction_T_min 0.9916 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean '9.091 pixels/mm' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count na _diffrn_standards_interval_time na _diffrn_standards_decay_% na _diffrn_reflns_number 8067 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.1198 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 23.25 _reflns_number_total 3169 _reflns_number_gt 1568 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; ? ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _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^)+(0.0480P)^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 SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3169 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1396 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 O1 O 0.8439(2) 0.3568(3) 0.3073(2) 0.0636(8) Uani 1 1 d . . . N1 N 1.1696(3) 0.5842(3) 0.0080(3) 0.0496(8) Uani 1 1 d . . . O4 O 1.2665(2) 0.2695(3) -0.0316(3) 0.0671(8) Uani 1 1 d . . . O3 O 1.3308(3) 0.2511(3) 0.1277(2) 0.0631(8) Uani 1 1 d . . . N2 N 1.2853(3) 0.7457(3) -0.1162(3) 0.0559(9) Uani 1 1 d . . . O2 O 1.0484(3) 0.2000(3) 0.2217(3) 0.0797(9) Uani 1 1 d . . . C6 C 1.7401(3) 0.6370(4) -0.4716(4) 0.0498(10) Uani 1 1 d . . . C18 C 1.1398(3) 0.4564(4) 0.0738(3) 0.0466(10) Uani 1 1 d . . . C17 C 1.0645(3) 0.7231(4) 0.0330(4) 0.0555(10) Uani 1 1 d . . . H17A H 1.0439 0.7207 0.1186 0.067 Uiso 1 1 calc R . . H17B H 0.9768 0.7459 0.0165 0.067 Uiso 1 1 calc R . . C14 C 1.4270(3) 0.4951(4) -0.1227(3) 0.0500(10) Uani 1 1 d . . . H14A H 1.4060 0.4489 -0.1629 0.060 Uiso 1 1 calc R . . H14B H 1.4586 0.4207 -0.0513 0.060 Uiso 1 1 calc R . . C13 C 1.5457(3) 0.5547(4) -0.2140(3) 0.0499(10) Uani 1 1 d . . . H13A H 1.5698 0.5955 -0.1715 0.060 Uiso 1 1 calc R . . H13B H 1.5107 0.6342 -0.2818 0.060 Uiso 1 1 calc R . . C7 C 1.7697(3) 0.4837(4) -0.3887(3) 0.0473(10) Uani 1 1 d . . . C19 C 1.0135(3) 0.4550(4) 0.1592(3) 0.0526(10) Uani 1 1 d . . . H19 H 0.9467 0.5433 0.1745 0.063 Uiso 1 1 calc R . . C12 C 1.6803(3) 0.4421(4) -0.2692(4) 0.0477(10) Uani 1 1 d . . . C15 C 1.2945(3) 0.6130(4) -0.0785(3) 0.0479(10) Uani 1 1 d . . . C1 C 1.7144(3) 0.7540(5) -0.4329(4) 0.0599(11) Uani 1 1 d . . . H1 H 1.7137 0.7381 -0.3522 0.072 Uiso 1 1 calc R . . C16 C 1.1400(3) 0.8331(4) -0.0593(4) 0.0622(11) Uani 1 1 d . . . H16A H 1.0912 0.8999 -0.1228 0.075 Uiso 1 1 calc R . . H16B H 1.1423 0.8899 -0.0161 0.075 Uiso 1 1 calc R . . C11 C 1.7167(3) 0.2950(4) -0.2018(4) 0.0626(11) Uani 1 1 d . . . H11 H 1.6584 0.2664 -0.1222 0.075 Uiso 1 1 calc R . . C10 C 1.8375(4) 0.1897(4) -0.2498(4) 0.0698(12) Uani 1 1 d . . . H10 H 1.8593 0.0916 -0.2033 0.084 Uiso 1 1 calc R . . C8 C 1.8912(3) 0.3759(5) -0.4351(4) 0.0606(11) Uani 1 1 d . . . H8 H 1.9508 0.4026 -0.5144 0.073 Uiso 1 1 calc R . . C20 C 0.9763(4) 0.3224(5) 0.2287(4) 0.0566(11) Uani 1 1 d . . . C21 C 0.7903(4) 0.2374(4) 0.3870(4) 0.0661(12) Uani 1 1 d . . . H21A H 0.8547 0.1622 0.4359 0.079 Uiso 1 1 calc R . . H21B H 0.7803 0.1937 0.3374 0.079 Uiso 1 1 calc R . . C5 C 1.7422(3) 0.6664(5) -0.5940(4) 0.0612(11) Uani 1 1 d . . . H5 H 1.7598 0.5900 -0.6227 0.073 Uiso 1 1 calc R . . C2 C 1.6897(4) 0.8944(5) -0.5139(5) 0.0719(13) Uani 1 1 d . . . H2 H 1.6717 0.9721 -0.4865 0.086 Uiso 1 1 calc R . . C3 C 1.6915(4) 0.9207(5) -0.6335(5) 0.0748(14) Uani 1 1 d . . . H3 H 1.6743 1.0156 -0.6870 0.090 Uiso 1 1 calc R . . C22 C 0.6484(4) 0.3022(4) 0.4711(4) 0.0733(13) Uani 1 1 d . . . H22A H 0.6613 0.3339 0.5269 0.110 Uiso 1 1 calc R . . H22B H 0.6031 0.2295 0.5187 0.110 Uiso 1 1 calc R . . H22C H 0.5900 0.3846 0.4216 0.110 Uiso 1 1 calc R . . C9 C 1.9248(4) 0.2312(5) -0.3664(5) 0.0710(13) Uani 1 1 d . . . H9 H 2.0068 0.1614 -0.3989 0.085 Uiso 1 1 calc R . . C4 C 1.7187(4) 0.8069(6) -0.6733(4) 0.0733(13) Uani 1 1 d . . . H4 H 1.7215 0.8239 -0.7549 0.088 Uiso 1 1 calc R . . C23 C 1.2511(4) 0.3153(4) 0.0494(4) 0.0507(10) Uani 1 1 d . . . C24 C 1.4474(4) 0.1111(5) 0.1190(5) 0.0912(15) Uani 1 1 d . . . H24A H 1.4824 0.1055 0.0338 0.109 Uiso 1 1 calc R . . H24B H 1.5250 0.1062 0.1407 0.109 Uiso 1 1 calc R . . C25 C 1.4004(5) -0.0105(5) 0.2012(5) 0.1131(18) Uani 1 1 d . . . H25A H 1.3620 -0.0029 0.2851 0.170 Uiso 1 1 calc R . . H25B H 1.4793 -0.1005 0.1976 0.170 Uiso 1 1 calc R . . H25C H 1.3283 -0.0097 0.1761 0.170 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 0.0597(15) 0.0601(18) 0.0627(18) -0.0195(15) 0.0097(13) -0.0359(14) N1 0.0428(16) 0.0385(19) 0.058(2) -0.0162(17) -0.0007(14) -0.0162(15) O4 0.0612(15) 0.080(2) 0.072(2) -0.0427(18) 0.0007(13) -0.0314(14) O3 0.0608(15) 0.0494(18) 0.066(2) -0.0132(15) -0.0167(14) -0.0122(14) N2 0.0496(17) 0.047(2) 0.058(2) -0.0139(18) 0.0004(14) -0.0200(16) O2 0.0674(17) 0.058(2) 0.097(2) -0.0313(18) 0.0085(15) -0.0285(16) C6 0.0350(18) 0.055(3) 0.057(3) -0.026(2) 0.0030(17) -0.0187(18) C18 0.045(2) 0.051(3) 0.045(2) -0.018(2) -0.0039(18) -0.0205(19) C17 0.048(2) 0.047(3) 0.063(3) -0.016(2) -0.0052(18) -0.0175(19) C14 0.0445(19) 0.051(3) 0.047(2) -0.013(2) -0.0038(16) -0.0190(18) C13 0.0413(18) 0.056(3) 0.050(2) -0.018(2) -0.0023(16) -0.0221(18) C7 0.0359(18) 0.051(3) 0.057(3) -0.022(2) -0.0024(18) -0.0189(18) C19 0.052(2) 0.050(3) 0.051(3) -0.019(2) 0.0011(18) -0.0233(19) C12 0.0348(18) 0.051(3) 0.062(3) -0.023(2) -0.0092(18) -0.0157(18) C15 0.042(2) 0.052(3) 0.046(2) -0.011(2) -0.0037(17) -0.0225(19) C1 0.056(2) 0.063(3) 0.058(3) -0.024(3) 0.0062(19) -0.031(2) C16 0.050(2) 0.053(3) 0.073(3) -0.023(2) 0.0014(19) -0.0209(19) C11 0.046(2) 0.054(3) 0.071(3) -0.014(3) -0.0083(19) -0.015(2) C10 0.051(2) 0.052(3) 0.097(4) -0.015(3) -0.023(2) -0.013(2) C8 0.045(2) 0.070(3) 0.067(3) -0.032(3) 0.0001(19) -0.022(2) C20 0.051(2) 0.059(3) 0.060(3) -0.022(3) -0.001(2) -0.027(2) C21 0.076(2) 0.066(3) 0.057(3) -0.012(2) -0.001(2) -0.045(2) C5 0.057(2) 0.072(3) 0.058(3) -0.030(3) 0.000(2) -0.028(2) C2 0.064(2) 0.063(3) 0.080(4) -0.028(3) 0.007(2) -0.032(2) C3 0.052(2) 0.058(3) 0.082(4) -0.003(3) -0.008(2) -0.017(2) C22 0.065(2) 0.084(3) 0.071(3) -0.023(3) 0.002(2) -0.043(2) C9 0.045(2) 0.063(3) 0.103(4) -0.036(3) -0.015(2) -0.010(2) C4 0.065(3) 0.075(4) 0.064(3) -0.014(3) -0.005(2) -0.028(3) C23 0.046(2) 0.056(3) 0.049(3) -0.018(2) 0.005(2) -0.030(2) C24 0.090(3) 0.064(3) 0.096(4) -0.021(3) -0.011(3) -0.022(3) C25 0.110(4) 0.081(4) 0.129(5) -0.034(4) -0.011(3) -0.033(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 O1 C20 1.351(4) . ? O1 C21 1.446(4) . ? N1 C18 1.373(4) . ? N1 C15 1.417(4) . ? N1 C17 1.466(4) . ? O4 C23 1.202(4) . ? O3 C23 1.331(4) . ? O3 C24 1.470(4) . ? N2 C15 1.261(4) . ? N2 C16 1.473(4) . ? O2 C20 1.199(4) . ? C6 C1 1.387(5) . ? C6 C5 1.394(5) . ? C6 C7 1.489(5) . ? C18 C19 1.350(4) . ? C18 C23 1.499(5) . ? C17 C16 1.531(4) . ? C14 C15 1.497(4) . ? C14 C13 1.519(4) . ? C13 C12 1.522(4) . ? C7 C8 1.395(5) . ? C7 C12 1.403(4) . ? C19 C20 1.457(5) . ? C12 C11 1.388(5) . ? C1 C2 1.385(5) . ? C11 C10 1.384(5) . ? C10 C9 1.371(5) . ? C8 C9 1.372(5) . ? C21 C22 1.500(5) . ? C5 C4 1.378(5) . ? C2 C3 1.369(6) . ? C3 C4 1.358(6) . ? C24 C25 1.432(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 C20 O1 C21 117.0(3) . . ? C18 N1 C15 132.4(3) . . ? C18 N1 C17 119.8(2) . . ? C15 N1 C17 107.5(3) . . ? C23 O3 C24 119.3(3) . . ? C15 N2 C16 108.8(3) . . ? C1 C6 C5 117.5(4) . . ? C1 C6 C7 122.3(4) . . ? C5 C6 C7 120.1(4) . . ? C19 C18 N1 121.8(3) . . ? C19 C18 C23 119.5(3) . . ? N1 C18 C23 118.7(3) . . ? N1 C17 C16 102.2(2) . . ? C15 C14 C13 112.1(3) . . ? C14 C13 C12 114.7(3) . . ? C8 C7 C12 118.8(3) . . ? C8 C7 C6 117.6(3) . . ? C12 C7 C6 123.6(3) . . ? C18 C19 C20 123.5(3) . . ? C11 C12 C7 118.5(3) . . ? C11 C12 C13 120.3(3) . . ? C7 C12 C13 121.2(3) . . ? N2 C15 N1 114.9(3) . . ? N2 C15 C14 122.5(3) . . ? N1 C15 C14 122.6(3) . . ? C2 C1 C6 120.4(4) . . ? N2 C16 C17 106.2(3) . . ? C10 C11 C12 121.8(4) . . ? C9 C10 C11 119.4(4) . . ? C9 C8 C7 121.5(4) . . ? O2 C20 O1 123.2(3) . . ? O2 C20 C19 127.5(3) . . ? O1 C20 C19 109.3(3) . . ? O1 C21 C22 106.4(3) . . ? C4 C5 C6 121.1(4) . . ? C3 C2 C1 121.0(4) . . ? C4 C3 C2 119.3(4) . . ? C10 C9 C8 120.0(4) . . ? C3 C4 C5 120.7(5) . . ? O4 C23 O3 125.5(4) . . ? O4 C23 C18 124.0(4) . . ? O3 C23 C18 110.5(4) . . ? C25 C24 O3 110.9(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.217 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.038