Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Atkinson, Robert S.' 'Meades, Christopher K.' _publ_contact_author_name 'Dr Robert S Atkinson' _publ_contact_author_address ; Dr Robert S Atkinson Department of Chemistry Leicester University Leicester LE1 7RH UNITED KINGDOM ; data_21 _database_code_CSD 160871 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H12 F3 N3 O' _chemical_formula_weight 307.28 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.012(3) _cell_length_b 7.6090(10) _cell_length_c 15.758(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.890(10) _cell_angle_gamma 90.00 _cell_volume 2769.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 31 _cell_measurement_theta_min 5.11 _cell_measurement_theta_max 12.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method ? _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker P4' _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 1237 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1038 _reflns_number_observed 808 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXL-93 (Sheldrick, 1993)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.1369P)^2^+11.5439P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1037 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_obs 0.0704 _refine_ls_wR_factor_all 0.2323 _refine_ls_wR_factor_obs 0.2078 _refine_ls_goodness_of_fit_all 1.078 _refine_ls_goodness_of_fit_obs 1.135 _refine_ls_restrained_S_all 1.097 _refine_ls_restrained_S_obs 1.135 _refine_ls_shift/esd_max -0.008 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group F1 F 0.1002(3) -0.1170(5) 0.2104(2) 0.076(3) Uani 1 d . . F2 F 0.0681(4) 0.0262(7) 0.3032(3) 0.084(4) Uani 1 d . . F3 F 0.1109(3) -0.2177(5) 0.3397(3) 0.088(4) Uani 1 d . . O1 O 0.2425(4) 0.3810(6) 0.2675(3) 0.065(4) Uani 1 d . . N1 N 0.2036(4) -0.0414(7) 0.3996(3) 0.0376(15) Uiso 1 d . . N2 N 0.1312(4) 0.2203(6) 0.2143(3) 0.0349(15) Uiso 1 d . . N3 N 0.1794(4) 0.1719(6) 0.2857(3) 0.0354(14) Uiso 1 d . . C2 C 0.1687(5) 0.0234(8) 0.3298(4) 0.033(2) Uiso 1 d . . C4 C 0.2333(5) 0.2590(8) 0.3096(4) 0.041(2) Uiso 1 d . . C5 C 0.2708(5) 0.1921(8) 0.3915(4) 0.041(2) Uiso 1 d . . C6 C 0.3242(5) 0.2771(9) 0.4282(4) 0.047(2) Uiso 1 d . . H6A H 0.3349(5) 0.3721(9) 0.3990(4) 0.057 Uiso 1 calc R . C7 C 0.3604(6) 0.2206(9) 0.5067(4) 0.052(2) Uiso 1 d . . H7A H 0.3950(6) 0.2784(9) 0.5320(4) 0.062 Uiso 1 calc R . C8 C 0.3440(5) 0.0743(9) 0.5478(5) 0.050(2) Uiso 1 d . . H8A H 0.3688(5) 0.0350(9) 0.6007(5) 0.060 Uiso 1 calc R . C9 C 0.2938(5) -0.0119(9) 0.5139(4) 0.045(2) Uiso 1 d . . H9A H 0.2847(5) -0.1096(9) 0.5429(4) 0.054 Uiso 1 calc R . C10 C 0.2550(5) 0.0465(8) 0.4340(4) 0.037(2) Uiso 1 d . . C11 C 0.1085(7) -0.0708(10) 0.2952(4) 0.082(7) Uani 1 d . . C12 C 0.1411(6) 0.2766(8) 0.1289(4) 0.048(5) Uani 1 d . . H12A H 0.1814(6) 0.2817(8) 0.1263(4) 0.057 Uiso 1 calc R . C13 C 0.1233(7) 0.4072(9) 0.1864(5) 0.081(7) Uani 1 d . . H13A H 0.1526(7) 0.4911(9) 0.2180(5) 0.097 Uiso 1 calc R . C14 C 0.0607(8) 0.4697(11) 0.1592(6) 0.098(8) Uani 1 d . . H14A H 0.0489(8) 0.4964(11) 0.2119(6) 0.117 Uiso 1 calc R . H14B H 0.0584(8) 0.5776(11) 0.1256(6) 0.117 Uiso 1 calc R . C15 C 0.0204(7) 0.3427(14) 0.1065(6) 0.115(8) Uani 1 d . . H15A H 0.0080(7) 0.2655(14) 0.1469(6) 0.138 Uiso 1 calc R . H15B H -0.0136(7) 0.4067(14) 0.0734(6) 0.138 Uiso 1 calc R . C16 C 0.0396(10) 0.2334(17) 0.0449(9) 0.096(15) Uani 1 d . . H16A H 0.0122(10) 0.1737(17) 0.0014(9) 0.116 Uiso 1 calc R . C17 C 0.0976(9) 0.2149(15) 0.0488(6) 0.078(13) Uani 1 d . . H17A H 0.1088(9) 0.1650(15) 0.0022(6) 0.093 Uiso 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 F1 0.139(10) 0.042(2) 0.035(2) -0.005(2) 0.005(3) -0.021(3) F2 0.121(12) 0.066(3) 0.058(3) -0.001(2) 0.014(4) -0.009(4) F3 0.142(11) 0.054(3) 0.053(2) 0.018(2) 0.001(3) -0.024(3) O1 0.079(12) 0.052(3) 0.050(3) 0.019(2) -0.007(4) -0.012(4) C11 0.164(21) 0.032(4) 0.037(3) 0.003(3) 0.003(6) -0.005(7) C12 0.052(17) 0.049(4) 0.034(3) 0.011(3) -0.003(5) 0.002(5) C13 0.149(23) 0.033(4) 0.044(4) 0.010(3) 0.000(6) -0.021(6) C14 0.151(24) 0.048(5) 0.069(5) 0.005(4) -0.013(8) -0.015(8) C15 0.155(26) 0.088(7) 0.080(6) 0.023(6) -0.006(9) -0.021(9) C16 0.110(41) 0.057(6) 0.087(7) -0.010(5) -0.032(13) -0.026(12) C17 0.135(38) 0.055(5) 0.037(4) 0.006(3) 0.013(9) -0.028(11) _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 F1 C11 1.344(8) . ? F2 C11 1.253(15) . ? F3 C11 1.312(8) . ? O1 C4 1.197(8) . ? N1 C2 1.284(9) . ? N1 C10 1.378(12) . ? N2 N3 1.424(9) . ? N2 C13 1.485(9) . ? N2 C12 1.493(10) . ? N3 C2 1.386(9) . ? N3 C4 1.411(13) . ? C2 C11 1.57(2) . ? C4 C5 1.449(11) . ? C5 C10 1.399(10) . ? C5 C6 1.410(15) . ? C6 C7 1.372(11) . ? C7 C8 1.397(11) . ? C8 C9 1.348(14) . ? C9 C10 1.418(10) . ? C12 C17 1.478(15) . ? C12 C13 1.486(13) . ? C13 C14 1.52(2) . ? C14 C15 1.46(2) . ? C15 C16 1.45(2) . ? C16 C17 1.38(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 C2 N1 C10 117.0(7) . . ? N3 N2 C13 119.5(7) . . ? N3 N2 C12 119.4(9) . . ? C13 N2 C12 59.9(5) . . ? C2 N3 C4 122.0(7) . . ? C2 N3 N2 112.7(8) . . ? C4 N3 N2 125.3(5) . . ? N1 C2 N3 125.2(9) . . ? N1 C2 C11 116.3(7) . . ? N3 C2 C11 118.4(7) . . ? O1 C4 N3 120.9(8) . . ? O1 C4 C5 127.0(10) . . ? N3 C4 C5 112.0(7) . . ? C10 C5 C6 120.1(7) . . ? C10 C5 C4 121.3(9) . . ? C6 C5 C4 118.5(7) . . ? C7 C6 C5 120.4(8) . . ? C6 C7 C8 118.6(10) . . ? C9 C8 C7 122.5(8) . . ? C8 C9 C10 120.0(7) . . ? N1 C10 C5 121.9(6) . . ? N1 C10 C9 119.8(7) . . ? C5 C10 C9 118.3(8) . . ? F2 C11 F3 111.8(12) . . ? F2 C11 F1 110.3(9) . . ? F3 C11 F1 106.4(6) . . ? F2 C11 C2 111.2(7) . . ? F3 C11 C2 107.5(9) . . ? F1 C11 C2 109.6(11) . . ? C17 C12 C13 118.6(12) . . ? C17 C12 N2 115.3(10) . . ? C13 C12 N2 59.8(5) . . ? N2 C13 C12 60.3(5) . . ? N2 C13 C14 114.8(11) . . ? C12 C13 C14 117.7(8) . . ? C15 C14 C13 113.9(10) . . ? C16 C15 C14 118.6(16) . . ? C17 C16 C15 122.1(15) . . ? C16 C17 C12 118.2(14) . . ? _refine_diff_density_max 0.268 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.060 data_33 _database_code_CSD 160872 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H25 N3 O2' _chemical_formula_sum 'C20 H25 N3 O2' _chemical_formula_weight 339.43 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 10.242(2) _cell_length_b 10.242(2) _cell_length_c 17.385(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1823.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 5.40 _cell_measurement_theta_max 12.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker P4' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 2357 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1779 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0534P)^2^+0.2562P] 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 -1.5(19) _refine_ls_number_reflns 1779 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0909 _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 O1 O -0.05400(18) 0.4206(2) 0.09431(13) 0.0467(5) Uani 1 1 d . . . O2 O 0.43346(18) 0.2104(2) 0.21509(13) 0.0487(5) Uani 1 1 d . . . H2 H 0.4022 0.1636 0.2486 0.073 Uiso 1 1 calc R . . N1 N 0.1611(2) 0.1757(2) 0.22936(14) 0.0394(6) Uani 1 1 d . . . N2 N 0.2081(2) 0.4147(2) 0.07628(14) 0.0375(5) Uani 1 1 d . . . N3 N 0.1421(2) 0.3365(2) 0.13298(13) 0.0359(5) Uani 1 1 d . . . C1 C 0.3502(3) 0.2101(3) 0.14959(18) 0.0438(7) Uani 1 1 d . . . H1B H 0.3798 0.2808 0.1158 0.053 Uiso 1 1 calc R . . C2 C 0.2119(3) 0.2426(3) 0.17354(16) 0.0365(6) Uani 1 1 d . . . C3 C 0.3566(3) 0.0817(3) 0.10192(19) 0.0492(8) Uani 1 1 d . . . C4 C 0.0061(3) 0.3448(3) 0.13642(17) 0.0374(6) Uani 1 1 d . . . C5 C -0.0523(3) 0.2626(3) 0.19481(17) 0.0356(6) Uani 1 1 d . . . C6 C -0.1890(3) 0.2608(3) 0.2051(2) 0.0441(7) Uani 1 1 d . . . H6A H -0.2430 0.3084 0.1725 0.053 Uiso 1 1 calc R . . C7 C -0.2417(3) 0.1881(3) 0.2639(2) 0.0513(9) Uani 1 1 d . . . H7A H -0.3317 0.1863 0.2708 0.062 Uiso 1 1 calc R . . C8 C -0.1620(3) 0.1174(3) 0.3129(2) 0.0484(8) Uani 1 1 d . . . H8A H -0.1991 0.0703 0.3531 0.058 Uiso 1 1 calc R . . C9 C -0.0284(3) 0.1158(3) 0.30318(18) 0.0430(7) Uani 1 1 d . . . H9A H 0.0242 0.0680 0.3365 0.052 Uiso 1 1 calc R . . C10 C 0.0279(2) 0.1868(3) 0.24246(17) 0.0362(6) Uani 1 1 d . . . C11 C 0.2686(4) 0.0966(4) 0.0315(2) 0.0618(9) Uani 1 1 d . . . H11A H 0.2726 0.0185 0.0011 0.093 Uiso 1 1 calc R . . H11B H 0.2977 0.1695 0.0013 0.093 Uiso 1 1 calc R . . H11C H 0.1803 0.1112 0.0479 0.093 Uiso 1 1 calc R . . C12 C 0.4985(3) 0.0654(4) 0.0756(2) 0.0686(11) Uani 1 1 d . . . H12A H 0.5067 -0.0136 0.0463 0.103 Uiso 1 1 calc R . . H12B H 0.5545 0.0611 0.1198 0.103 Uiso 1 1 calc R . . H12C H 0.5231 0.1386 0.0443 0.103 Uiso 1 1 calc R . . C13 C 0.3159(3) -0.0384(3) 0.1476(2) 0.0573(9) Uani 1 1 d . . . H13A H 0.3240 -0.1146 0.1159 0.086 Uiso 1 1 calc R . . H13B H 0.2269 -0.0290 0.1639 0.086 Uiso 1 1 calc R . . H13C H 0.3712 -0.0472 0.1919 0.086 Uiso 1 1 calc R . . C14 C 0.1811(3) 0.5569(3) 0.0863(2) 0.0474(7) Uani 1 1 d . . . H14A H 0.1218 0.5773 0.1290 0.057 Uiso 1 1 calc R . . C15 C 0.1544(3) 0.6327(3) 0.0139(2) 0.0559(9) Uani 1 1 d . . . H15A H 0.0680 0.6092 -0.0042 0.067 Uiso 1 1 calc R . . H15B H 0.1523 0.7248 0.0270 0.067 Uiso 1 1 calc R . . C16 C 0.2482(3) 0.6149(4) -0.0513(2) 0.0612(9) Uani 1 1 d . . . H16A H 0.2114 0.6549 -0.0970 0.073 Uiso 1 1 calc R . . H16B H 0.2575 0.5223 -0.0615 0.073 Uiso 1 1 calc R . . C17 C 0.3834(4) 0.6728(3) -0.0372(2) 0.0617(9) Uani 1 1 d . . . H17A H 0.4254 0.6883 -0.0863 0.074 Uiso 1 1 calc R . . H17B H 0.3737 0.7565 -0.0117 0.074 Uiso 1 1 calc R . . C18 C 0.4691(4) 0.5877(3) 0.0104(2) 0.0597(9) Uani 1 1 d . . . H18A H 0.5565 0.5843 -0.0041 0.072 Uiso 1 1 calc R . . C19 C 0.4365(3) 0.5160(4) 0.0709(2) 0.0564(9) Uani 1 1 d . . . H19A H 0.5032 0.4651 0.0912 0.068 Uiso 1 1 calc R . . C20 C 0.3099(3) 0.5052(3) 0.11071(19) 0.0483(7) Uani 1 1 d . . . H20A H 0.3184 0.4963 0.1666 0.058 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 0.0408(11) 0.0524(12) 0.0468(13) -0.0010(11) -0.0075(10) 0.0095(9) O2 0.0338(10) 0.0649(13) 0.0476(12) 0.0186(12) -0.0035(10) -0.0049(9) N1 0.0318(11) 0.0501(13) 0.0362(13) 0.0036(11) 0.0042(11) 0.0039(10) N2 0.0378(12) 0.0431(12) 0.0316(12) 0.0046(11) 0.0018(10) 0.0025(10) N3 0.0344(11) 0.0431(12) 0.0302(12) 0.0002(10) 0.0029(10) 0.0026(10) C1 0.0330(15) 0.0578(18) 0.0404(16) 0.0155(15) 0.0028(14) 0.0051(13) C2 0.0342(14) 0.0436(15) 0.0317(15) 0.0013(13) -0.0008(12) 0.0015(12) C3 0.0396(16) 0.065(2) 0.0425(17) 0.0067(17) 0.0082(15) 0.0155(14) C4 0.0367(14) 0.0388(14) 0.0365(15) -0.0122(13) -0.0052(13) 0.0066(11) C5 0.0323(13) 0.0363(13) 0.0382(15) -0.0114(12) 0.0002(12) 0.0012(11) C6 0.0321(14) 0.0434(15) 0.0566(19) -0.0146(15) -0.0018(15) 0.0013(12) C7 0.0308(15) 0.0505(17) 0.073(2) -0.0171(18) 0.0094(16) -0.0021(13) C8 0.0440(16) 0.0438(16) 0.057(2) -0.0096(16) 0.0156(16) -0.0066(14) C9 0.0391(15) 0.0466(16) 0.0432(17) -0.0034(14) 0.0045(14) -0.0018(12) C10 0.0347(14) 0.0371(14) 0.0367(15) -0.0077(12) 0.0045(12) 0.0009(11) C11 0.066(2) 0.077(2) 0.0425(18) -0.0016(18) 0.0024(18) 0.0159(18) C12 0.055(2) 0.088(3) 0.062(2) 0.013(2) 0.0226(19) 0.0245(19) C13 0.059(2) 0.058(2) 0.055(2) -0.0016(18) 0.0061(18) 0.0103(16) C14 0.0530(18) 0.0432(16) 0.0458(18) -0.0050(15) 0.0073(15) 0.0013(13) C15 0.0548(19) 0.0430(16) 0.070(2) 0.0087(18) 0.0061(18) 0.0085(15) C16 0.065(2) 0.063(2) 0.056(2) 0.0167(19) 0.0008(18) -0.0009(16) C17 0.073(2) 0.0476(18) 0.065(2) 0.0076(18) 0.013(2) -0.0082(16) C18 0.0533(19) 0.059(2) 0.067(2) 0.002(2) 0.0068(19) -0.0160(16) C19 0.0456(17) 0.065(2) 0.059(2) 0.0065(19) -0.0051(16) -0.0122(15) C20 0.0539(18) 0.0533(17) 0.0379(16) 0.0005(15) -0.0034(14) -0.0068(14) _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 C4 1.232(3) . ? O2 C1 1.422(4) . ? N1 C2 1.297(4) . ? N1 C10 1.388(3) . ? N2 N3 1.439(3) . ? N2 C14 1.493(4) . ? N2 C20 1.518(4) . ? N3 C2 1.390(3) . ? N3 C4 1.397(3) . ? C1 C2 1.513(4) . ? C1 C3 1.556(5) . ? C3 C13 1.522(5) . ? C3 C11 1.528(5) . ? C3 C12 1.533(4) . ? C4 C5 1.448(4) . ? C5 C10 1.401(4) . ? C5 C6 1.412(4) . ? C6 C7 1.375(5) . ? C7 C8 1.384(5) . ? C8 C9 1.379(4) . ? C9 C10 1.406(4) . ? C14 C20 1.484(4) . ? C14 C15 1.504(5) . ? C15 C16 1.497(5) . ? C16 C17 1.527(5) . ? C17 C18 1.489(5) . ? C18 C19 1.325(5) . ? C19 C20 1.473(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 C2 N1 C10 118.3(2) . . ? N3 N2 C14 112.1(2) . . ? N3 N2 C20 113.1(2) . . ? C14 N2 C20 59.02(19) . . ? C2 N3 C4 122.3(2) . . ? C2 N3 N2 119.4(2) . . ? C4 N3 N2 117.6(2) . . ? O2 C1 C2 109.9(2) . . ? O2 C1 C3 113.8(2) . . ? C2 C1 C3 111.8(2) . . ? N1 C2 N3 122.6(2) . . ? N1 C2 C1 117.7(2) . . ? N3 C2 C1 119.6(2) . . ? C13 C3 C11 109.7(3) . . ? C13 C3 C12 109.1(3) . . ? C11 C3 C12 109.3(3) . . ? C13 C3 C1 113.2(3) . . ? C11 C3 C1 108.5(3) . . ? C12 C3 C1 106.9(3) . . ? O1 C4 N3 120.8(3) . . ? O1 C4 C5 125.2(2) . . ? N3 C4 C5 114.0(2) . . ? C10 C5 C6 119.9(3) . . ? C10 C5 C4 119.6(2) . . ? C6 C5 C4 120.4(3) . . ? C7 C6 C5 119.4(3) . . ? C6 C7 C8 120.6(3) . . ? C9 C8 C7 121.0(3) . . ? C8 C9 C10 119.5(3) . . ? N1 C10 C5 121.7(3) . . ? N1 C10 C9 118.9(3) . . ? C5 C10 C9 119.4(2) . . ? C20 C14 N2 61.33(18) . . ? C20 C14 C15 125.8(3) . . ? N2 C14 C15 116.0(3) . . ? C16 C15 C14 117.0(3) . . ? C15 C16 C17 114.4(3) . . ? C18 C17 C16 113.4(3) . . ? C19 C18 C17 128.1(3) . . ? C18 C19 C20 129.5(3) . . ? C19 C20 C14 128.4(3) . . ? C19 C20 N2 117.7(3) . . ? C14 C20 N2 59.65(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.029