# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Joaquin Rodriguez Moran' _publ_contact_author_email ROMORAN@USAL.ES _publ_section_title ; Imidazolidinone Intermediates in Prolinamide-Catalyzed Aldol Reactions ; loop_ _publ_author_name 'Joaquin Rodriguez Moran' 'Victoria Alcazar' 'A.F.de Arriba' 'Francisco M. Muniz' 'Cesar Raposo' 'Francisca Sanz' ; L.Simon ; # Attachment 'Base1.cif.txt' data_19fin _database_code_depnum_ccdc_archive 'CCDC 741181' #TrackingRef 'Base1.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N2 O' _chemical_formula_sum 'C14 H18 N2 O' _chemical_formula_weight 230.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7304(3) _cell_length_b 8.9046(2) _cell_length_c 16.6172(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1291.83(7) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6372 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 65.58 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.595 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _vrf_DENSX01_19fin ; PROBLEM: The ratio of the calculated to measured crystal density RESPONSE: We have checked that we have entered the density correctly and that in our calculations we have allowed correctly for all distinct moieties present, including any solvent and all H atoms. ; # end Validation Reply Form _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7935 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.32 _diffrn_reflns_theta_max 65.57 _reflns_number_total 2084 _reflns_number_gt 2049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.1046P] 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 0.0210(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 2084 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration rm 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 -0.00348(10) 0.38301(10) 0.93222(6) 0.0551(3) Uani 1 1 d . . . N1 N -0.25420(11) 0.34637(10) 0.89397(6) 0.0409(2) Uani 1 1 d . . . N2 N -0.36668(12) 0.56363(11) 0.94210(6) 0.0481(3) Uani 1 1 d . . . C1 C -0.13622(14) 0.42467(13) 0.92560(7) 0.0417(3) Uani 1 1 d . . . C2 C -0.19871(14) 0.57641(14) 0.95160(8) 0.0483(3) Uani 1 1 d . . . C3 C -0.16883(19) 0.61526(19) 1.04004(10) 0.0703(4) Uani 1 1 d . . . H3A H -0.1162 0.5338 1.0672 0.084 Uiso 1 1 calc R . . H3B H -0.1080 0.7060 1.0447 0.084 Uiso 1 1 calc R . . C4 C -0.3273(2) 0.6382(2) 1.07444(11) 0.0878(6) Uani 1 1 d . . . H4A H -0.3311 0.6104 1.1308 0.105 Uiso 1 1 calc R . . H4B H -0.3602 0.7417 1.0687 0.105 Uiso 1 1 calc R . . C5 C -0.4238(2) 0.5345(2) 1.02403(9) 0.0715(4) Uani 1 1 d . . . H5A H -0.4083 0.4305 1.0393 0.086 Uiso 1 1 calc R . . H5B H -0.5318 0.5589 1.0286 0.086 Uiso 1 1 calc R . . C6 C -0.39256(14) 0.44418(13) 0.88267(7) 0.0455(3) Uani 1 1 d . . . C7 C -0.38895(19) 0.51208(17) 0.79833(8) 0.0625(4) Uani 1 1 d . . . H7A H -0.4727 0.5810 0.7923 0.094 Uiso 1 1 calc R . . H7B H -0.3978 0.4335 0.7591 0.094 Uiso 1 1 calc R . . H7C H -0.2940 0.5645 0.7906 0.094 Uiso 1 1 calc R . . C8 C -0.54093(16) 0.35893(16) 0.89587(10) 0.0602(4) Uani 1 1 d . . . H8A H -0.5388 0.3114 0.9477 0.090 Uiso 1 1 calc R . . H8B H -0.5523 0.2839 0.8548 0.090 Uiso 1 1 calc R . . H8C H -0.6256 0.4275 0.8934 0.090 Uiso 1 1 calc R . . C9 C -0.23480(14) 0.20326(13) 0.85570(7) 0.0414(3) Uani 1 1 d . . . C10 C -0.15205(17) 0.19243(15) 0.78511(8) 0.0548(3) Uani 1 1 d . . . H10 H -0.1071 0.2774 0.7627 0.066 Uiso 1 1 calc R . . C11 C -0.13637(18) 0.05383(18) 0.74780(9) 0.0645(4) Uani 1 1 d . . . H11 H -0.0807 0.0461 0.7003 0.077 Uiso 1 1 calc R . . C12 C -0.20246(17) -0.07166(16) 0.78062(9) 0.0594(4) Uani 1 1 d . . . H12 H -0.1924 -0.1641 0.7552 0.071 Uiso 1 1 calc R . . C13 C -0.28359(16) -0.06051(14) 0.85125(9) 0.0542(3) Uani 1 1 d . . . H13 H -0.3280 -0.1459 0.8735 0.065 Uiso 1 1 calc R . . C14 C -0.29978(14) 0.07638(13) 0.88954(8) 0.0462(3) Uani 1 1 d . . . H14 H -0.3539 0.0831 0.9376 0.055 Uiso 1 1 calc R . . H2 H -0.1561(18) 0.6510(17) 0.9152(9) 0.058(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0421(5) 0.0599(6) 0.0632(6) -0.0025(4) -0.0052(4) 0.0041(4) N1 0.0398(5) 0.0367(5) 0.0463(5) 0.0000(4) -0.0017(4) 0.0012(4) N2 0.0468(6) 0.0426(5) 0.0549(6) -0.0032(5) -0.0004(5) 0.0038(5) C1 0.0432(6) 0.0419(6) 0.0399(5) 0.0063(5) 0.0001(5) -0.0016(5) C2 0.0474(7) 0.0412(6) 0.0562(7) 0.0006(6) -0.0024(6) -0.0025(5) C3 0.0710(10) 0.0687(9) 0.0711(9) -0.0234(7) -0.0126(8) 0.0052(8) C4 0.0893(12) 0.1047(13) 0.0694(9) -0.0309(10) 0.0033(10) 0.0087(11) C5 0.0657(9) 0.0848(11) 0.0640(8) -0.0115(8) 0.0152(7) -0.0010(8) C6 0.0435(6) 0.0404(6) 0.0525(7) 0.0027(5) -0.0046(5) 0.0047(5) C7 0.0733(10) 0.0593(8) 0.0549(8) 0.0075(6) -0.0129(7) 0.0046(8) C8 0.0429(7) 0.0544(8) 0.0832(10) -0.0008(8) -0.0058(7) 0.0010(6) C9 0.0418(6) 0.0389(6) 0.0436(6) -0.0002(5) -0.0027(5) 0.0026(5) C10 0.0598(8) 0.0524(7) 0.0520(7) 0.0029(6) 0.0113(6) -0.0016(6) C11 0.0694(9) 0.0683(9) 0.0558(7) -0.0113(7) 0.0120(7) 0.0113(8) C12 0.0570(8) 0.0482(7) 0.0731(9) -0.0137(7) -0.0084(7) 0.0097(7) C13 0.0505(7) 0.0410(6) 0.0710(8) 0.0031(6) -0.0033(7) 0.0019(6) C14 0.0455(6) 0.0431(6) 0.0500(6) 0.0055(5) 0.0014(5) 0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2218(14) . ? N1 C1 1.3503(15) . ? N1 C9 1.4342(15) . ? N1 C6 1.5010(15) . ? N2 C6 1.4689(16) . ? N2 C5 1.4730(19) . ? N2 C2 1.4793(16) . ? C1 C2 1.5198(17) . ? C2 C3 1.532(2) . ? C2 H2 0.972(16) . ? C3 C4 1.511(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.505(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.5173(18) . ? C6 C7 1.5267(18) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.3811(18) . ? C9 C14 1.3836(17) . ? C10 C11 1.388(2) . ? C10 H10 0.9300 . ? C11 C12 1.371(2) . ? C11 H11 0.9300 . ? C12 C13 1.374(2) . ? C12 H12 0.9300 . ? C13 C14 1.3823(18) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 C1 N1 C9 122.77(10) . . ? C1 N1 C6 111.28(9) . . ? C9 N1 C6 123.72(9) . . ? C6 N2 C5 116.22(11) . . ? C6 N2 C2 106.26(10) . . ? C5 N2 C2 104.51(11) . . ? O1 C1 N1 127.00(11) . . ? O1 C1 C2 125.79(11) . . ? N1 C1 C2 107.21(10) . . ? N2 C2 C1 104.90(10) . . ? N2 C2 C3 106.77(11) . . ? C1 C2 C3 114.35(11) . . ? N2 C2 H2 111.4(9) . . ? C1 C2 H2 107.1(9) . . ? C3 C2 H2 112.2(9) . . ? C4 C3 C2 103.73(12) . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 102.66(13) . . ? C5 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? C5 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? N2 C5 C4 102.52(13) . . ? N2 C5 H5A 111.3 . . ? C4 C5 H5A 111.3 . . ? N2 C5 H5B 111.3 . . ? C4 C5 H5B 111.3 . . ? H5A C5 H5B 109.2 . . ? N2 C6 N1 102.26(9) . . ? N2 C6 C8 113.35(11) . . ? N1 C6 C8 112.25(10) . . ? N2 C6 C7 109.10(11) . . ? N1 C6 C7 109.15(11) . . ? C8 C6 C7 110.39(12) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 120.17(11) . . ? C10 C9 N1 120.03(11) . . ? C14 C9 N1 119.80(10) . . ? C9 C10 C11 119.55(13) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.37(12) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.86(12) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.63(13) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 119.41(12) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 65.57 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.099 _refine_diff_density_min -0.089 _refine_diff_density_rms 0.022 # Attachment 'Base2.cif.txt' data_invertida #TrackingRef 'Base2.cif.txt' _database_code_depnum_ccdc_archive 'CCDC 741182' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N3 O3, C H2 Cl2' _chemical_formula_sum 'C19 H19 Cl2 N3 O3' _chemical_formula_weight 408.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8341(4) _cell_length_b 8.8407(4) _cell_length_c 11.5844(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.936(3) _cell_angle_gamma 90.00 _cell_volume 994.93(8) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1507 _cell_measurement_theta_min 3.86 _cell_measurement_theta_max 59.58 _exptl_crystal_description Prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 3.142 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _vrf_DENSX01_invertida ; PROBLEM: The ratio of the calculated to measured crystal density RESPONSE: We have checked that we have entered the density correctly and that in our calculations we have allowed correctly for all distinct moieties present, including any solvent and all H atoms. ; # end Validation Reply Form _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5546 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 64.58 _reflns_number_total 2820 _reflns_number_gt 2368 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1124P)^2^+0.2413P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 2820 _refine_ls_number_parameters 252 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1867 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration rm 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 0.7568(5) 0.7230(5) 0.5453(3) 0.0931(12) Uani 1 1 d . . . O2 O 0.9297(4) 0.0978(7) 1.1688(4) 0.1230(19) Uani 1 1 d . . . O3 O 0.7228(4) 0.0572(6) 1.1903(3) 0.1005(13) Uani 1 1 d . . . N1 N 0.7009(3) 0.5352(4) 0.6685(3) 0.0567(8) Uani 1 1 d . . . N2 N 0.6269(3) 0.6825(4) 0.8131(3) 0.0550(8) Uani 1 1 d . . . N3 N 0.8076(4) 0.1193(5) 1.1416(3) 0.0698(10) Uani 1 1 d . . . C1 C 0.7083(5) 0.6816(5) 0.6309(3) 0.0639(11) Uani 1 1 d . . . C2 C 0.6439(5) 0.7807(5) 0.7136(3) 0.0620(10) Uani 1 1 d . . . C3 C 0.7324(6) 0.9159(6) 0.7638(4) 0.0853(15) Uani 1 1 d . . . H3A H 0.8180 0.9201 0.7321 0.102 Uiso 1 1 calc R . . H3B H 0.6834 1.0106 0.7471 0.102 Uiso 1 1 calc R . . C4 C 0.7586(6) 0.8845(7) 0.8931(5) 0.0874(15) Uani 1 1 d . . . H4A H 0.8505 0.9166 0.9270 0.105 Uiso 1 1 calc R . . H4B H 0.6923 0.9374 0.9323 0.105 Uiso 1 1 calc R . . C5 C 0.7437(5) 0.7194(5) 0.9043(4) 0.0680(11) Uani 1 1 d . . . H5A H 0.8265 0.6672 0.8907 0.082 Uiso 1 1 calc R . . H5B H 0.7239 0.6926 0.9811 0.082 Uiso 1 1 calc R . . C6 C 0.6218(4) 0.5280(5) 0.7673(3) 0.0506(8) Uani 1 1 d . . . C7 C 0.6732(4) 0.4123(5) 0.8596(3) 0.0517(8) Uani 1 1 d . . . C8 C 0.5831(4) 0.3657(5) 0.9340(4) 0.0589(10) Uani 1 1 d . . . H8 H 0.4925 0.3995 0.9213 0.071 Uiso 1 1 calc R . . C9 C 0.6270(4) 0.2694(5) 1.0268(3) 0.0609(10) Uani 1 1 d . . . H9 H 0.5668 0.2379 1.0764 0.073 Uiso 1 1 calc R . . C10 C 0.7600(4) 0.2223(5) 1.0433(3) 0.0539(9) Uani 1 1 d . . . C11 C 0.8522(4) 0.2643(5) 0.9707(3) 0.0577(9) Uani 1 1 d . . . H11 H 0.9426 0.2299 0.9844 0.069 Uiso 1 1 calc R . . C12 C 0.8078(4) 0.3581(5) 0.8777(3) 0.0559(9) Uani 1 1 d . . . H12 H 0.8679 0.3854 0.8268 0.067 Uiso 1 1 calc R . . C13 C 0.7269(5) 0.4057(5) 0.6015(3) 0.0616(10) Uani 1 1 d . . . C14 C 0.6308(6) 0.2909(6) 0.5801(4) 0.0778(13) Uani 1 1 d . . . H14 H 0.5473 0.2984 0.6080 0.093 Uiso 1 1 calc R . . C15 C 0.6592(8) 0.1644(7) 0.5169(5) 0.101(2) Uani 1 1 d . . . H15 H 0.5955 0.0862 0.5031 0.121 Uiso 1 1 calc R . . C16 C 0.7853(11) 0.1559(10) 0.4741(5) 0.116(3) Uani 1 1 d . . . H16 H 0.8049 0.0720 0.4312 0.139 Uiso 1 1 calc R . . C17 C 0.8782(8) 0.2697(10) 0.4953(5) 0.107(2) Uani 1 1 d . . . H17 H 0.9607 0.2638 0.4657 0.129 Uiso 1 1 calc R . . C18 C 0.8518(6) 0.3941(7) 0.5600(4) 0.0862(15) Uani 1 1 d . . . H18 H 0.9175 0.4701 0.5759 0.103 Uiso 1 1 calc R . . C19 C 0.7907(8) 0.6517(16) 0.2873(6) 0.144(4) Uani 1 1 d . . . H19A H 0.8138 0.6312 0.3703 0.173 Uiso 1 1 calc R . . H19B H 0.7921 0.7605 0.2767 0.173 Uiso 1 1 calc R . . Cl1 Cl 0.6297(2) 0.5868(6) 0.2393(2) 0.1790(14) Uani 1 1 d . . . Cl2 Cl 0.9120(2) 0.5725(5) 0.2172(2) 0.1740(14) Uani 1 1 d . . . H2 H 0.544(5) 0.797(6) 0.670(4) 0.074(13) Uiso 1 1 d . . . H6 H 0.532(5) 0.505(5) 0.741(3) 0.047(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.138(3) 0.080(2) 0.0736(19) 0.0122(17) 0.055(2) -0.003(2) O2 0.079(2) 0.161(5) 0.131(3) 0.072(3) 0.023(2) 0.031(3) O3 0.092(2) 0.121(4) 0.091(2) 0.035(2) 0.021(2) -0.003(2) N1 0.0663(19) 0.0554(19) 0.0529(15) -0.0034(15) 0.0238(14) -0.0016(16) N2 0.0584(18) 0.0532(19) 0.0562(16) -0.0033(13) 0.0178(13) 0.0014(14) N3 0.071(2) 0.078(3) 0.063(2) 0.0113(18) 0.0192(17) 0.010(2) C1 0.076(3) 0.066(3) 0.053(2) 0.0040(18) 0.0212(18) -0.003(2) C2 0.079(3) 0.054(2) 0.0557(19) 0.0039(18) 0.0170(19) 0.001(2) C3 0.112(4) 0.061(3) 0.088(3) -0.008(3) 0.030(3) -0.017(3) C4 0.096(4) 0.070(3) 0.094(3) -0.013(3) 0.007(3) -0.007(3) C5 0.075(3) 0.066(3) 0.061(2) -0.0074(19) 0.0069(19) 0.000(2) C6 0.048(2) 0.056(2) 0.0506(18) -0.0035(16) 0.0162(15) -0.0050(17) C7 0.0497(19) 0.056(2) 0.0520(17) -0.0062(17) 0.0171(14) -0.0062(17) C8 0.0483(19) 0.064(2) 0.068(2) 0.0023(19) 0.0210(16) -0.0020(18) C9 0.063(2) 0.063(2) 0.062(2) 0.0021(18) 0.0258(17) -0.0036(19) C10 0.056(2) 0.055(2) 0.0523(17) 0.0007(16) 0.0139(15) 0.0014(16) C11 0.052(2) 0.058(2) 0.066(2) 0.0014(18) 0.0187(16) 0.0029(18) C12 0.0493(19) 0.065(2) 0.0572(19) 0.0023(17) 0.0213(15) -0.0043(17) C13 0.081(3) 0.063(3) 0.0436(17) -0.0029(18) 0.0178(16) 0.010(2) C14 0.102(4) 0.067(3) 0.061(2) -0.008(2) 0.003(2) 0.005(3) C15 0.149(6) 0.069(3) 0.076(3) -0.012(3) -0.011(3) 0.007(4) C16 0.175(8) 0.102(5) 0.071(3) -0.017(3) 0.019(4) 0.049(6) C17 0.130(5) 0.110(5) 0.090(3) -0.004(4) 0.046(4) 0.040(5) C18 0.091(3) 0.099(4) 0.078(3) 0.001(3) 0.040(2) 0.022(3) C19 0.113(5) 0.227(12) 0.096(4) -0.031(6) 0.029(4) 0.020(6) Cl1 0.1038(13) 0.269(4) 0.167(2) -0.050(2) 0.0291(13) -0.0025(19) Cl2 0.1108(14) 0.282(4) 0.1375(16) -0.035(2) 0.0443(12) 0.0270(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 O1 C1 1.222(5) . ? O2 N3 1.208(5) . ? O3 N3 1.209(5) . ? N1 C1 1.370(6) . ? N1 C13 1.428(6) . ? N1 C6 1.482(5) . ? N2 C6 1.463(5) . ? N2 C5 1.471(6) . ? N2 C2 1.473(6) . ? N3 C10 1.476(6) . ? C1 C2 1.508(6) . ? C2 C3 1.539(7) . ? C2 H2 1.04(5) . ? C3 C4 1.506(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.475(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.509(6) . ? C6 H6 0.91(4) . ? C7 C8 1.391(5) . ? C7 C12 1.393(6) . ? C8 C9 1.386(6) . ? C8 H8 0.9300 . ? C9 C10 1.358(6) . ? C9 H9 0.9300 . ? C10 C11 1.380(6) . ? C11 C12 1.375(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.383(7) . ? C13 C18 1.391(7) . ? C14 C15 1.388(8) . ? C14 H14 0.9300 . ? C15 C16 1.407(12) . ? C15 H15 0.9300 . ? C16 C17 1.355(12) . ? C16 H16 0.9300 . ? C17 C18 1.378(10) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 Cl1 1.695(10) . ? C19 Cl2 1.695(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? 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 C1 N1 C13 124.2(3) . . ? C1 N1 C6 110.2(3) . . ? C13 N1 C6 123.0(3) . . ? C6 N2 C5 116.5(3) . . ? C6 N2 C2 105.6(3) . . ? C5 N2 C2 105.1(3) . . ? O2 N3 O3 122.4(4) . . ? O2 N3 C10 118.9(4) . . ? O3 N3 C10 118.7(4) . . ? O1 C1 N1 126.0(4) . . ? O1 C1 C2 126.6(4) . . ? N1 C1 C2 107.4(3) . . ? N2 C2 C1 105.3(4) . . ? N2 C2 C3 106.8(3) . . ? C1 C2 C3 115.0(4) . . ? N2 C2 H2 104(3) . . ? C1 C2 H2 103(3) . . ? C3 C2 H2 121(3) . . ? C4 C3 C2 103.4(4) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 105.4(4) . . ? C5 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? C5 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? N2 C5 C4 103.5(4) . . ? N2 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? N2 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.0 . . ? N2 C6 N1 104.3(3) . . ? N2 C6 C7 112.8(3) . . ? N1 C6 C7 114.7(3) . . ? N2 C6 H6 108(3) . . ? N1 C6 H6 110(2) . . ? C7 C6 H6 107(3) . . ? C8 C7 C12 119.1(4) . . ? C8 C7 C6 117.7(3) . . ? C12 C7 C6 123.1(3) . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 118.3(3) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 122.8(4) . . ? C9 C10 N3 118.8(3) . . ? C11 C10 N3 118.4(3) . . ? C12 C11 C10 118.7(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C7 120.3(3) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C14 C13 C18 120.0(5) . . ? C14 C13 N1 120.7(4) . . ? C18 C13 N1 119.3(5) . . ? C13 C14 C15 119.9(6) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 119.3(7) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 120.2(6) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.8(7) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C13 119.9(7) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? Cl1 C19 Cl2 113.2(6) . . ? Cl1 C19 H19A 108.9 . . ? Cl2 C19 H19A 108.9 . . ? Cl1 C19 H19B 108.9 . . ? Cl2 C19 H19B 108.9 . . ? H19A C19 H19B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 64.58 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.465 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.048 # Attachment 'Base3.cif.txt' data_19r _database_code_depnum_ccdc_archive 'CCDC 741183' #TrackingRef 'Base3.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N3 O3' _chemical_formula_sum 'C18 H17 N3 O3' _chemical_formula_weight 323.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall P2ac2ab 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 6.6712(2) _cell_length_b 14.9403(4) _cell_length_c 15.7482(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1569.62(7) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.780 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9894 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.62 _diffrn_reflns_theta_max 64.85 _reflns_number_total 2441 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.1560P] 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 0.0108(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 2441 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration rm 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 -0.09533(15) 0.03590(8) 0.68760(8) 0.0604(3) Uani 1 1 d . . . O2 O 0.5680(3) -0.20987(11) 1.05205(10) 0.1122(7) Uani 1 1 d . . . O3 O 0.8489(3) -0.13816(12) 1.05132(10) 0.1049(6) Uani 1 1 d . . . N1 N 0.25127(15) 0.02706(8) 0.69470(7) 0.0397(3) Uani 1 1 d . . . N2 N 0.31477(18) 0.15087(8) 0.78022(7) 0.0425(3) Uani 1 1 d . . . N3 N 0.6813(3) -0.15215(11) 1.02450(9) 0.0781(5) Uani 1 1 d . . . C1 C 0.0662(2) 0.05936(10) 0.71599(9) 0.0434(3) Uani 1 1 d . . . C2 C 0.0992(2) 0.13070(10) 0.78357(9) 0.0436(3) Uani 1 1 d . . . C3 C -0.0123(3) 0.21843(11) 0.76667(11) 0.0575(4) Uani 1 1 d . . . H3A H -0.1129 0.2105 0.7228 0.069 Uiso 1 1 calc R . . H3B H -0.0773 0.2399 0.8179 0.069 Uiso 1 1 calc R . . C4 C 0.1477(3) 0.28270(12) 0.73806(13) 0.0705(5) Uani 1 1 d . . . H4A H 0.1763 0.3261 0.7823 0.085 Uiso 1 1 calc R . . H4B H 0.1053 0.3144 0.6874 0.085 Uiso 1 1 calc R . . C5 C 0.3306(3) 0.22628(10) 0.71971(11) 0.0579(4) Uani 1 1 d . . . H5A H 0.3293 0.2049 0.6615 0.070 Uiso 1 1 calc R . . H5B H 0.4526 0.2601 0.7292 0.070 Uiso 1 1 calc R . . C6 C 0.4070(2) 0.06822(9) 0.74872(8) 0.0390(3) Uani 1 1 d . . . C7 C 0.46997(19) 0.00878(9) 0.82213(9) 0.0394(3) Uani 1 1 d . . . C8 C 0.6464(2) 0.02943(11) 0.86428(9) 0.0496(4) Uani 1 1 d . . . H8 H 0.7195 0.0795 0.8477 0.060 Uiso 1 1 calc R . . C9 C 0.7154(2) -0.02273(12) 0.93019(10) 0.0568(4) Uani 1 1 d . . . H9 H 0.8350 -0.0089 0.9576 0.068 Uiso 1 1 calc R . . C10 C 0.6047(3) -0.09501(10) 0.95436(9) 0.0549(4) Uani 1 1 d . . . C11 C 0.4278(3) -0.11654(10) 0.91637(11) 0.0624(4) Uani 1 1 d . . . H11 H 0.3529 -0.1651 0.9354 0.075 Uiso 1 1 calc R . . C12 C 0.3614(2) -0.06483(10) 0.84888(10) 0.0536(4) Uani 1 1 d . . . H12 H 0.2427 -0.0798 0.8214 0.064 Uiso 1 1 calc R . . C13 C 0.2956(2) -0.03981(9) 0.63364(8) 0.0411(3) Uani 1 1 d . . . C14 C 0.4873(2) -0.07580(11) 0.63026(11) 0.0556(4) Uani 1 1 d . . . H14 H 0.5846 -0.0570 0.6686 0.067 Uiso 1 1 calc R . . C15 C 0.5332(3) -0.13975(12) 0.56973(11) 0.0675(5) Uani 1 1 d . . . H15 H 0.6612 -0.1644 0.5683 0.081 Uiso 1 1 calc R . . C16 C 0.3927(3) -0.16735(11) 0.51177(10) 0.0655(5) Uani 1 1 d . . . H16 H 0.4253 -0.2099 0.4709 0.079 Uiso 1 1 calc R . . C17 C 0.2041(3) -0.13156(11) 0.51473(10) 0.0608(5) Uani 1 1 d . . . H17 H 0.1087 -0.1499 0.4753 0.073 Uiso 1 1 calc R . . C18 C 0.1530(2) -0.06862(10) 0.57525(9) 0.0513(4) Uani 1 1 d . . . H18 H 0.0235 -0.0456 0.5770 0.062 Uiso 1 1 calc R . . H2 H 0.062(2) 0.1066(9) 0.8397(10) 0.044(4) Uiso 1 1 d . . . H6 H 0.528(2) 0.0790(10) 0.7143(9) 0.042(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0366(5) 0.0764(7) 0.0681(7) -0.0106(6) -0.0058(5) -0.0042(5) O2 0.1932(19) 0.0750(9) 0.0686(9) 0.0223(8) -0.0199(11) 0.0067(12) O3 0.1202(14) 0.1222(13) 0.0724(9) 0.0016(9) -0.0338(9) 0.0516(12) N1 0.0352(6) 0.0434(6) 0.0404(6) -0.0034(5) -0.0035(5) -0.0017(5) N2 0.0435(6) 0.0395(6) 0.0444(6) -0.0002(5) 0.0007(5) -0.0040(5) N3 0.1197(15) 0.0684(10) 0.0461(8) -0.0027(8) -0.0089(10) 0.0329(11) C1 0.0373(7) 0.0481(8) 0.0447(7) 0.0039(7) -0.0010(6) -0.0022(7) C2 0.0397(7) 0.0494(8) 0.0418(7) 0.0021(6) 0.0028(6) 0.0001(7) C3 0.0617(10) 0.0580(9) 0.0529(9) -0.0043(8) 0.0021(8) 0.0128(8) C4 0.0738(12) 0.0489(9) 0.0889(13) 0.0062(9) -0.0064(10) 0.0035(9) C5 0.0656(10) 0.0449(8) 0.0633(9) 0.0089(8) 0.0085(8) -0.0038(8) C6 0.0348(7) 0.0431(7) 0.0392(7) -0.0011(6) -0.0001(6) -0.0046(6) C7 0.0373(7) 0.0425(7) 0.0385(7) -0.0047(6) 0.0008(6) 0.0011(6) C8 0.0381(7) 0.0643(9) 0.0464(7) 0.0020(7) -0.0010(7) -0.0027(7) C9 0.0481(8) 0.0771(11) 0.0450(8) -0.0041(8) -0.0063(7) 0.0095(9) C10 0.0743(11) 0.0523(9) 0.0382(7) -0.0031(7) -0.0045(8) 0.0208(8) C11 0.0886(13) 0.0443(8) 0.0543(9) 0.0050(7) -0.0017(10) -0.0067(9) C12 0.0590(9) 0.0470(8) 0.0550(8) 0.0027(7) -0.0084(7) -0.0095(8) C13 0.0475(8) 0.0396(7) 0.0363(7) 0.0027(6) -0.0039(6) -0.0015(6) C14 0.0500(8) 0.0632(9) 0.0537(9) -0.0135(8) -0.0057(7) 0.0052(8) C15 0.0702(11) 0.0700(11) 0.0622(10) -0.0160(9) 0.0010(9) 0.0171(9) C16 0.0950(14) 0.0530(9) 0.0485(9) -0.0102(8) -0.0029(10) 0.0064(10) C17 0.0863(13) 0.0487(8) 0.0474(8) -0.0037(7) -0.0207(9) -0.0034(9) C18 0.0592(9) 0.0463(8) 0.0485(8) -0.0004(7) -0.0152(7) 0.0007(8) _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 C1 1.2185(17) . ? O2 N3 1.226(2) . ? O3 N3 1.213(2) . ? N1 C1 1.3670(17) . ? N1 C13 1.4180(17) . ? N1 C6 1.4768(17) . ? N2 C6 1.4661(18) . ? N2 C2 1.4703(19) . ? N2 C5 1.4793(19) . ? N3 C10 1.487(2) . ? C1 C2 1.522(2) . ? C2 C3 1.530(2) . ? C2 H2 0.987(15) . ? C3 C4 1.505(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.511(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.5170(19) . ? C6 H6 0.988(14) . ? C7 C12 1.383(2) . ? C7 C8 1.3860(19) . ? C8 C9 1.377(2) . ? C8 H8 0.9300 . ? C9 C10 1.363(2) . ? C9 H9 0.9300 . ? C10 C11 1.362(3) . ? C11 C12 1.387(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.388(2) . ? C13 C18 1.392(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9300 . ? C15 C16 1.372(3) . ? C15 H15 0.9300 . ? C16 C17 1.368(3) . ? C16 H16 0.9300 . ? C17 C18 1.382(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 C1 N1 C13 127.12(11) . . ? C1 N1 C6 110.30(11) . . ? C13 N1 C6 122.50(10) . . ? C6 N2 C2 104.48(11) . . ? C6 N2 C5 113.18(11) . . ? C2 N2 C5 104.41(12) . . ? O3 N3 O2 124.49(19) . . ? O3 N3 C10 118.4(2) . . ? O2 N3 C10 117.1(2) . . ? O1 C1 N1 127.39(13) . . ? O1 C1 C2 125.85(13) . . ? N1 C1 C2 106.75(11) . . ? N2 C2 C1 105.05(11) . . ? N2 C2 C3 107.08(12) . . ? C1 C2 C3 114.07(13) . . ? N2 C2 H2 110.8(9) . . ? C1 C2 H2 109.5(8) . . ? C3 C2 H2 110.2(8) . . ? C4 C3 C2 104.69(13) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 105.91(14) . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? N2 C5 C4 104.14(13) . . ? N2 C5 H5A 110.9 . . ? C4 C5 H5A 110.9 . . ? N2 C5 H5B 110.9 . . ? C4 C5 H5B 110.9 . . ? H5A C5 H5B 108.9 . . ? N2 C6 N1 104.50(11) . . ? N2 C6 C7 110.58(11) . . ? N1 C6 C7 112.96(11) . . ? N2 C6 H6 113.1(9) . . ? N1 C6 H6 109.2(8) . . ? C7 C6 H6 106.7(8) . . ? C12 C7 C8 118.43(14) . . ? C12 C7 C6 123.54(12) . . ? C8 C7 C6 118.03(12) . . ? C9 C8 C7 121.27(15) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 118.54(15) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 122.29(15) . . ? C11 C10 N3 119.24(17) . . ? C9 C10 N3 118.46(17) . . ? C10 C11 C12 118.84(16) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C7 C12 C11 120.60(15) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C18 119.01(13) . . ? C14 C13 N1 119.42(12) . . ? C18 C13 N1 121.55(12) . . ? C15 C14 C13 119.85(15) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.96(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 119.24(15) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 121.11(16) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 119.82(15) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 64.85 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.100 _refine_diff_density_min -0.089 _refine_diff_density_rms 0.025