# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Keith Smith' _publ_contact_author_email SMITHK13@CARDIFF.AC.UK _publ_section_title ; One-pot Synthesis of Substituted Isoindolin-1-ones via Lithiation and Substitution of N'-benzyl-N,N-dimethylureas ; loop_ _publ_author_name 'Keith Smith' 'Gamal A. El-Hiti' 'Amany S. Hegazy' # Attachment 'Comp_13_-_CCDC737411.cif' data_ks0804 _database_code_depnum_ccdc_archive 'CCDC 737411' #TrackingRef 'Comp_13_-_CCDC737411.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N O2' _chemical_formula_sum 'C9 H9 N O2' _chemical_formula_weight 163.17 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' O O 0.0106 0.0060 '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' _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 7.2640(5) _cell_length_b 7.8940(6) _cell_length_c 8.3280(8) _cell_angle_alpha 104.845(3) _cell_angle_beta 114.462(4) _cell_angle_gamma 103.622(5) _cell_volume 387.21(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1267 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2379 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1714 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0641P)^2^+0.0804P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1714 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.0708(3) -0.3299(2) 0.2616(2) 0.0281(4) Uani 1 1 d . . . C2 C 0.2111(3) -0.0365(2) 0.2476(2) 0.0246(4) Uani 1 1 d . . . H2A H 0.1170 0.0266 0.1859 0.029 Uiso 1 1 calc R . . H2B H 0.3523 0.0098 0.2510 0.029 Uiso 1 1 calc R . . C3 C 0.2456(2) -0.0056(2) 0.4444(2) 0.0240(4) Uani 1 1 d . . . C4 C 0.1625(2) -0.1774(2) 0.4532(2) 0.0243(4) Uani 1 1 d . . . C5 C 0.1720(3) -0.1898(3) 0.6204(2) 0.0275(4) Uani 1 1 d . . . H5 H 0.1138 -0.3086 0.6247 0.033 Uiso 1 1 calc R . . C6 C 0.2705(3) -0.0205(3) 0.7797(2) 0.0294(4) Uani 1 1 d . . . H6 H 0.2808 -0.0236 0.8963 0.035 Uiso 1 1 calc R . . C7 C 0.3551(3) 0.1546(3) 0.7743(2) 0.0283(4) Uani 1 1 d . . . H7 H 0.4219 0.2681 0.8865 0.034 Uiso 1 1 calc R . . C8 C 0.3425(3) 0.1643(2) 0.6054(2) 0.0259(4) Uani 1 1 d . . . C9 C 0.5053(3) 0.5036(2) 0.7382(3) 0.0390(5) Uani 1 1 d . . . H9A H 0.3905 0.5154 0.7678 0.059 Uiso 1 1 calc R . . H9B H 0.5540 0.6076 0.7027 0.059 Uiso 1 1 calc R . . H9C H 0.6299 0.5098 0.8515 0.059 Uiso 1 1 calc R . . O1 O 0.4200(2) 0.32536(17) 0.58131(17) 0.0327(3) Uani 1 1 d . . . O2 O -0.0179(2) -0.50326(17) 0.21087(18) 0.0369(4) Uani 1 1 d . . . N1 N 0.1020(2) -0.2422(2) 0.1499(2) 0.0286(4) Uani 1 1 d . . . H1 H 0.0599 -0.3043 0.0285 0.034 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 C1 0.0281(9) 0.0283(10) 0.0232(9) 0.0077(7) 0.0133(7) 0.0055(7) C2 0.0257(8) 0.0269(9) 0.0188(8) 0.0082(7) 0.0108(7) 0.0084(7) C3 0.0216(8) 0.0293(9) 0.0189(8) 0.0074(7) 0.0093(7) 0.0102(7) C4 0.0215(8) 0.0282(9) 0.0217(8) 0.0090(7) 0.0109(7) 0.0082(7) C5 0.0272(8) 0.0339(10) 0.0240(9) 0.0136(8) 0.0141(7) 0.0116(7) C6 0.0296(9) 0.0427(11) 0.0214(9) 0.0139(8) 0.0151(7) 0.0170(8) C7 0.0285(9) 0.0320(10) 0.0185(8) 0.0041(7) 0.0105(7) 0.0117(7) C8 0.0249(8) 0.0293(9) 0.0227(8) 0.0092(7) 0.0121(7) 0.0106(7) C9 0.0503(12) 0.0265(11) 0.0331(10) 0.0030(8) 0.0219(10) 0.0117(9) O1 0.0436(7) 0.0245(7) 0.0270(7) 0.0071(5) 0.0191(6) 0.0096(6) O2 0.0486(8) 0.0264(8) 0.0286(7) 0.0066(5) 0.0223(6) 0.0029(6) N1 0.0330(8) 0.0262(8) 0.0179(7) 0.0042(6) 0.0127(6) 0.0030(6) _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 C1 O2 1.237(2) . ? C1 N1 1.352(2) . ? C1 C4 1.482(2) . ? C2 N1 1.452(2) . ? C2 C3 1.496(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.383(2) . ? C3 C8 1.394(2) . ? C4 C5 1.395(2) . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 C7 1.395(2) . ? C6 H6 0.9500 . ? C7 C8 1.395(2) . ? C7 H7 0.9500 . ? C8 O1 1.364(2) . ? C9 O1 1.431(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N1 H1 0.8800 . ? 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 O2 C1 N1 126.01(16) . . ? O2 C1 C4 127.69(16) . . ? N1 C1 C4 106.30(15) . . ? N1 C2 C3 101.46(13) . . ? N1 C2 H2A 111.5 . . ? C3 C2 H2A 111.5 . . ? N1 C2 H2B 111.5 . . ? C3 C2 H2B 111.5 . . ? H2A C2 H2B 109.3 . . ? C4 C3 C8 120.45(16) . . ? C4 C3 C2 110.37(14) . . ? C8 C3 C2 129.18(16) . . ? C3 C4 C5 122.36(16) . . ? C3 C4 C1 107.72(15) . . ? C5 C4 C1 129.93(16) . . ? C6 C5 C4 116.68(17) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 121.7 . . ? C5 C6 C7 122.01(16) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C8 120.49(16) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? O1 C8 C3 115.64(15) . . ? O1 C8 C7 126.35(16) . . ? C3 C8 C7 118.00(16) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 O1 C9 117.37(14) . . ? C1 N1 C2 114.15(14) . . ? C1 N1 H1 122.9 . . ? C2 N1 H1 122.9 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.235 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.054 # Attachment 'Comp_4_-CCDC737415.cif' data_ks0810 _database_code_depnum_ccdc_archive 'CCDC 737415' #TrackingRef 'Comp_4_-CCDC737415.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N O4' _chemical_formula_sum 'C17 H17 N O4' _chemical_formula_weight 299.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _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 7.5240(3) _cell_length_b 9.4100(3) _cell_length_c 11.9960(5) _cell_angle_alpha 83.877(2) _cell_angle_beta 77.311(2) _cell_angle_gamma 68.559(2) _cell_volume 770.92(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2539 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9818 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5071 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3513 _reflns_number_gt 2539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0452P)^2^+0.4323P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3513 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 C1 C 0.2151(3) 0.2870(2) 0.60320(16) 0.0218(4) Uani 1 1 d . . . C2 C 0.2871(3) 0.1307(2) 0.65399(16) 0.0220(4) Uani 1 1 d . . . C3 C 0.1840(3) 0.0471(3) 0.72304(18) 0.0309(5) Uani 1 1 d . . . H3 H 0.0488 0.0855 0.7424 0.037 Uiso 1 1 calc R . . C4 C 0.2911(3) -0.0954(3) 0.76155(19) 0.0333(5) Uani 1 1 d . . . H4 H 0.2260 -0.1533 0.8087 0.040 Uiso 1 1 calc R . . C5 C 0.4939(3) -0.1555(2) 0.73223(17) 0.0285(5) Uani 1 1 d . . . H5 H 0.5616 -0.2526 0.7588 0.034 Uiso 1 1 calc R . . C6 C 0.5950(3) -0.0697(2) 0.66302(16) 0.0224(4) Uani 1 1 d . . . C7 C 0.4880(3) 0.0751(2) 0.62507(15) 0.0201(4) Uani 1 1 d . . . C8 C 0.5583(3) 0.1959(2) 0.55858(16) 0.0197(4) Uani 1 1 d . . . H8 H 0.6344 0.1588 0.4832 0.024 Uiso 1 1 calc R . . C9 C 0.9066(3) -0.2588(3) 0.6731(2) 0.0375(6) Uani 1 1 d . . . H9A H 0.8774 -0.2611 0.7552 0.056 Uiso 1 1 calc R . . H9B H 1.0423 -0.2746 0.6468 0.056 Uiso 1 1 calc R . . H9C H 0.8769 -0.3381 0.6457 0.056 Uiso 1 1 calc R . . C10 C 0.6774(3) 0.2512(2) 0.62221(16) 0.0217(4) Uani 1 1 d . . . H10 H 0.8000 0.1670 0.6270 0.026 Uiso 1 1 calc R . . C11 C 0.5706(3) 0.2997(2) 0.74238(16) 0.0215(4) Uani 1 1 d . . . C12 C 0.5876(3) 0.1938(2) 0.83348(17) 0.0258(4) Uani 1 1 d . . . H12 H 0.6722 0.0938 0.8207 0.031 Uiso 1 1 calc R . . C13 C 0.4821(3) 0.2337(2) 0.94246(17) 0.0280(5) Uani 1 1 d . . . H13 H 0.4952 0.1609 1.0020 0.034 Uiso 1 1 calc R . . C14 C 0.3561(3) 0.3834(2) 0.96254(17) 0.0273(5) Uani 1 1 d . . . C15 C 0.3384(3) 0.4913(2) 0.87379(18) 0.0285(5) Uani 1 1 d . . . H15 H 0.2554 0.5917 0.8871 0.034 Uiso 1 1 calc R . . C16 C 0.4455(3) 0.4489(2) 0.76442(17) 0.0265(5) Uani 1 1 d . . . H16 H 0.4330 0.5219 0.7051 0.032 Uiso 1 1 calc R . . C17 C 0.1370(3) 0.5686(3) 1.09920(19) 0.0371(6) Uani 1 1 d . . . H17A H 0.2176 0.6301 1.0825 0.056 Uiso 1 1 calc R . . H17B H 0.0778 0.5743 1.1789 0.056 Uiso 1 1 calc R . . H17C H 0.0373 0.6054 1.0542 0.056 Uiso 1 1 calc R . . O1 O 0.0450(2) 0.37467(16) 0.61120(12) 0.0284(3) Uani 1 1 d . . . O2 O 0.7916(2) -0.11306(15) 0.63091(12) 0.0292(4) Uani 1 1 d . . . O3 O 0.7209(2) 0.37137(16) 0.55327(12) 0.0266(3) Uani 1 1 d . . . H3A H 0.8183 0.3795 0.5676 0.040 Uiso 1 1 calc R . . O4 O 0.2535(2) 0.41330(18) 1.07237(12) 0.0362(4) Uani 1 1 d . . . N1 N 0.3741(2) 0.31693(18) 0.54696(13) 0.0223(4) Uani 1 1 d . . . H1 H 0.3677 0.4000 0.5077 0.027 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 C1 0.0250(10) 0.0231(10) 0.0197(9) -0.0028(8) -0.0069(8) -0.0093(8) C2 0.0269(10) 0.0216(10) 0.0200(9) 0.0002(8) -0.0076(8) -0.0101(8) C3 0.0292(11) 0.0337(12) 0.0331(11) 0.0053(9) -0.0083(9) -0.0155(10) C4 0.0400(13) 0.0328(12) 0.0340(12) 0.0125(10) -0.0103(10) -0.0230(10) C5 0.0401(12) 0.0198(10) 0.0289(11) 0.0061(8) -0.0124(9) -0.0127(9) C6 0.0287(10) 0.0191(9) 0.0196(9) -0.0016(8) -0.0063(8) -0.0075(8) C7 0.0266(10) 0.0173(9) 0.0183(9) -0.0006(7) -0.0066(8) -0.0086(8) C8 0.0225(10) 0.0185(9) 0.0175(9) 0.0008(7) -0.0045(7) -0.0063(8) C9 0.0357(13) 0.0264(11) 0.0378(13) 0.0047(10) -0.0074(10) 0.0022(10) C10 0.0221(9) 0.0210(9) 0.0237(10) 0.0045(8) -0.0052(8) -0.0105(8) C11 0.0241(10) 0.0218(10) 0.0226(10) -0.0007(8) -0.0056(8) -0.0120(8) C12 0.0311(11) 0.0221(10) 0.0262(10) 0.0002(8) -0.0098(8) -0.0095(9) C13 0.0387(12) 0.0279(11) 0.0212(10) 0.0041(8) -0.0090(9) -0.0157(10) C14 0.0324(11) 0.0318(11) 0.0210(10) -0.0022(9) -0.0035(8) -0.0156(9) C15 0.0337(12) 0.0240(10) 0.0278(11) -0.0012(8) -0.0031(9) -0.0116(9) C16 0.0362(12) 0.0230(10) 0.0219(10) 0.0029(8) -0.0050(9) -0.0135(9) C17 0.0406(13) 0.0408(13) 0.0288(11) -0.0100(10) 0.0018(10) -0.0157(11) O1 0.0249(8) 0.0277(8) 0.0321(8) -0.0004(6) -0.0088(6) -0.0067(6) O2 0.0277(8) 0.0205(7) 0.0318(8) 0.0029(6) -0.0033(6) -0.0021(6) O3 0.0263(8) 0.0271(8) 0.0299(8) 0.0068(6) -0.0072(6) -0.0147(6) O4 0.0472(10) 0.0371(9) 0.0211(8) -0.0030(7) 0.0015(7) -0.0151(8) N1 0.0256(9) 0.0194(8) 0.0224(8) 0.0042(7) -0.0071(7) -0.0084(7) _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 C1 O1 1.232(2) . ? C1 N1 1.348(2) . ? C1 C2 1.483(3) . ? C2 C7 1.382(3) . ? C2 C3 1.390(3) . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 H4 0.9300 . ? C5 C6 1.396(3) . ? C5 H5 0.9300 . ? C6 O2 1.358(2) . ? C6 C7 1.392(3) . ? C7 C8 1.506(3) . ? C8 N1 1.461(2) . ? C8 C10 1.544(3) . ? C8 H8 0.9800 . ? C9 O2 1.436(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O3 1.422(2) . ? C10 C11 1.515(3) . ? C10 H10 0.9800 . ? C11 C16 1.390(3) . ? C11 C12 1.392(3) . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 C14 1.392(3) . ? C13 H13 0.9300 . ? C14 O4 1.373(2) . ? C14 C15 1.384(3) . ? C15 C16 1.393(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O4 1.431(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O3 H3A 0.8200 . ? N1 H1 0.8600 . ? 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 O1 C1 N1 126.01(19) . . ? O1 C1 C2 127.69(18) . . ? N1 C1 C2 106.29(17) . . ? C7 C2 C3 121.98(19) . . ? C7 C2 C1 108.27(17) . . ? C3 C2 C1 129.72(19) . . ? C4 C3 C2 117.1(2) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? C3 C4 C5 122.2(2) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C4 C5 C6 119.93(19) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O2 C6 C7 116.07(17) . . ? O2 C6 C5 125.75(18) . . ? C7 C6 C5 118.16(18) . . ? C2 C7 C6 120.64(18) . . ? C2 C7 C8 109.82(16) . . ? C6 C7 C8 129.41(18) . . ? N1 C8 C7 101.28(14) . . ? N1 C8 C10 111.33(15) . . ? C7 C8 C10 113.04(15) . . ? N1 C8 H8 110.3 . . ? C7 C8 H8 110.3 . . ? C10 C8 H8 110.3 . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 C11 112.75(15) . . ? O3 C10 C8 106.44(15) . . ? C11 C10 C8 112.10(15) . . ? O3 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C8 C10 H10 108.5 . . ? C16 C11 C12 117.88(18) . . ? C16 C11 C10 121.28(18) . . ? C12 C11 C10 120.76(17) . . ? C13 C12 C11 121.68(19) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 119.54(19) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? O4 C14 C15 123.99(19) . . ? O4 C14 C13 116.08(18) . . ? C15 C14 C13 119.92(18) . . ? C14 C15 C16 119.72(19) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 121.24(19) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 O2 C9 117.45(16) . . ? C10 O3 H3A 109.5 . . ? C14 O4 C17 117.80(17) . . ? C1 N1 C8 114.12(16) . . ? C1 N1 H1 122.9 . . ? C8 N1 H1 122.9 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.506 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.055 # Attachment 'Comp_9.cif' data_ks0912 _database_code_depnum_ccdc_archive 'CCDC 762623' #TrackingRef 'Comp_9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N O2, C4 H8 O2' _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 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 7.5698(6) _cell_length_b 9.2785(8) _cell_length_c 12.2934(10) _cell_angle_alpha 78.473(4) _cell_angle_beta 82.365(4) _cell_angle_gamma 70.596(3) _cell_volume 795.91(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1954 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 27.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4991 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.21 _reflns_number_total 3467 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0791P)^2^+0.5844P] 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 SHELXL _refine_ls_extinction_coef 0.137(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3467 _refine_ls_number_parameters 238 _refine_ls_number_restraints 77 _refine_ls_R_factor_all 0.1491 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2035 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_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_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 C1 C 0.7616(5) 0.2346(4) 0.3902(3) 0.0329(8) Uani 1 1 d . . . C2 C 0.6810(4) 0.4029(4) 0.3460(3) 0.0288(8) Uani 1 1 d . . . C3 C 0.7695(5) 0.5058(4) 0.2856(3) 0.0333(8) Uani 1 1 d . . . H3 H 0.9008 0.4739 0.2664 0.040 Uiso 1 1 calc R . . C4 C 0.6581(5) 0.6568(4) 0.2546(3) 0.0377(9) Uani 1 1 d . . . H4 H 0.7144 0.7301 0.2129 0.045 Uiso 1 1 calc R . . C5 C 0.4652(5) 0.7046(4) 0.2828(3) 0.0333(8) Uani 1 1 d . . . H5 H 0.3923 0.8093 0.2602 0.040 Uiso 1 1 calc R . . C6 C 0.3786(5) 0.5995(4) 0.3438(3) 0.0303(8) Uani 1 1 d . . . C7 C 0.4905(4) 0.4466(4) 0.3747(3) 0.0272(7) Uani 1 1 d . . . C8 C 0.4343(4) 0.3089(3) 0.4364(3) 0.0277(7) Uani 1 1 d . . . H8 H 0.3800 0.3271 0.5130 0.033 Uiso 1 1 calc R . . C9 C 0.0725(5) 0.7887(4) 0.3425(3) 0.0467(10) Uani 1 1 d . . . H9A H 0.1161 0.8611 0.3713 0.070 Uiso 1 1 calc R . . H9B H -0.0568 0.7979 0.3723 0.070 Uiso 1 1 calc R . . H9C H 0.0767 0.8132 0.2611 0.070 Uiso 1 1 calc R . . C10 C 0.2949(4) 0.2702(4) 0.3757(3) 0.0282(8) Uani 1 1 d . . . H10 H 0.1729 0.3563 0.3756 0.034 Uiso 1 1 calc R . . C11 C 0.3625(4) 0.2501(4) 0.2568(3) 0.0292(8) Uani 1 1 d . . . C12 C 0.4781(5) 0.1079(4) 0.2307(3) 0.0347(8) Uani 1 1 d . . . H12 H 0.5142 0.0214 0.2886 0.042 Uiso 1 1 calc R . . C13 C 0.5415(5) 0.0908(5) 0.1213(3) 0.0444(10) Uani 1 1 d . . . H13 H 0.6184 -0.0074 0.1045 0.053 Uiso 1 1 calc R . . C14 C 0.4930(6) 0.2158(5) 0.0373(3) 0.0491(10) Uani 1 1 d . . . H14 H 0.5380 0.2044 -0.0374 0.059 Uiso 1 1 calc R . . C15 C 0.3790(6) 0.3581(5) 0.0611(3) 0.0466(10) Uani 1 1 d . . . H15 H 0.3449 0.4440 0.0027 0.056 Uiso 1 1 calc R . . C16 C 0.3137(5) 0.3763(4) 0.1706(3) 0.0370(9) Uani 1 1 d . . . H16 H 0.2359 0.4746 0.1866 0.044 Uiso 1 1 calc R . . C17 C -0.0361(13) 0.2594(8) 0.0360(9) 0.061(2) Uani 0.50 1 d PDU . . H17A H -0.0340 0.3073 0.0998 0.092 Uiso 0.50 1 calc PR . . H17B H -0.1616 0.3014 0.0080 0.092 Uiso 0.50 1 calc PR . . H17C H 0.0563 0.2818 -0.0229 0.092 Uiso 0.50 1 calc PR . . C18 C 0.0142(12) 0.0760(7) 0.0740(5) 0.052(2) Uani 0.50 1 d PDU . . H18A H 0.1425 0.0297 0.0999 0.063 Uiso 0.50 1 calc PR . . H18B H -0.0767 0.0499 0.1340 0.063 Uiso 0.50 1 calc PR . . C19 C 0.0223(11) -0.1365(5) 0.0011(5) 0.048(2) Uani 0.50 1 d PDU . . C20 C 0.0187(12) -0.1944(10) -0.1063(6) 0.052(2) Uani 0.50 1 d PDU . . H20A H 0.0005 -0.1079 -0.1687 0.078 Uiso 0.50 1 calc PR . . H20B H -0.0848 -0.2378 -0.0992 0.078 Uiso 0.50 1 calc PR . . H20C H 0.1379 -0.2747 -0.1200 0.078 Uiso 0.50 1 calc PR . . N1 N 0.6158(4) 0.1878(3) 0.4423(2) 0.0301(7) Uani 1 1 d . . . H1 H 0.6296 0.0924 0.4768 0.036 Uiso 1 1 calc R . . O1 O 0.9262(3) 0.1523(3) 0.3816(2) 0.0409(7) Uani 1 1 d . . . O2 O 0.1922(3) 0.6326(3) 0.3761(2) 0.0387(7) Uani 1 1 d . . . O3 O 0.2662(3) 0.1329(2) 0.44083(19) 0.0321(6) Uani 1 1 d . . . H3A H 0.1587 0.1311 0.4324 0.048 Uiso 1 1 calc R . . O4 O 0.0008(12) 0.0250(5) -0.0259(3) 0.0394(15) Uani 0.50 1 d PDU . . O5 O 0.0422(9) -0.2145(6) 0.0868(4) 0.0610(16) Uani 0.50 1 d PDU . . 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 C1 0.030(2) 0.0329(19) 0.040(2) -0.0083(16) -0.0067(15) -0.0120(16) C2 0.0302(18) 0.0273(18) 0.0315(18) -0.0061(14) -0.0069(14) -0.0102(14) C3 0.0333(18) 0.037(2) 0.0337(19) -0.0029(15) -0.0042(15) -0.0166(16) C4 0.044(2) 0.037(2) 0.037(2) 0.0005(16) -0.0054(16) -0.0222(18) C5 0.046(2) 0.0214(17) 0.0347(19) -0.0006(14) -0.0128(16) -0.0127(16) C6 0.0336(19) 0.0283(18) 0.0305(18) -0.0080(15) -0.0060(15) -0.0083(15) C7 0.0281(17) 0.0271(17) 0.0279(17) -0.0054(14) -0.0028(13) -0.0099(14) C8 0.0273(17) 0.0245(17) 0.0307(18) -0.0022(14) -0.0052(14) -0.0077(14) C9 0.039(2) 0.031(2) 0.060(3) -0.0067(19) -0.0064(19) 0.0027(17) C10 0.0286(17) 0.0218(17) 0.0332(18) 0.0010(14) -0.0053(14) -0.0090(14) C11 0.0265(17) 0.0317(19) 0.0332(19) -0.0017(15) -0.0069(14) -0.0143(15) C12 0.040(2) 0.0304(19) 0.036(2) -0.0015(15) -0.0048(16) -0.0158(16) C13 0.048(2) 0.047(2) 0.044(2) -0.0138(19) 0.0009(18) -0.0203(19) C14 0.055(3) 0.065(3) 0.036(2) -0.011(2) 0.0004(18) -0.029(2) C15 0.053(2) 0.062(3) 0.031(2) 0.0101(18) -0.0151(18) -0.032(2) C16 0.038(2) 0.033(2) 0.042(2) 0.0024(16) -0.0134(17) -0.0158(16) C17 0.055(5) 0.063(6) 0.067(6) -0.012(5) -0.005(5) -0.020(4) C18 0.044(4) 0.051(5) 0.064(5) -0.028(4) 0.003(4) -0.009(4) C19 0.042(4) 0.049(5) 0.055(5) -0.017(4) 0.002(4) -0.015(4) C20 0.052(5) 0.056(5) 0.054(5) -0.008(4) -0.009(4) -0.025(4) N1 0.0305(15) 0.0228(14) 0.0365(16) 0.0019(12) -0.0114(12) -0.0084(12) O1 0.0258(14) 0.0367(14) 0.0604(17) -0.0106(12) -0.0090(11) -0.0066(11) O2 0.0291(14) 0.0273(13) 0.0550(16) -0.0083(11) -0.0007(11) -0.0025(11) O3 0.0265(12) 0.0296(13) 0.0396(14) 0.0054(10) -0.0063(10) -0.0129(10) O4 0.048(3) 0.027(4) 0.041(4) 0.002(3) -0.012(4) -0.010(3) O5 0.083(4) 0.053(3) 0.036(3) 0.003(3) -0.009(3) -0.011(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 C1 O1 1.230(4) . ? C1 N1 1.355(4) . ? C1 C2 1.491(5) . ? C2 C7 1.379(4) . ? C2 C3 1.386(5) . ? C3 C4 1.380(5) . ? C4 C5 1.395(5) . ? C5 C6 1.395(5) . ? C6 O2 1.362(4) . ? C6 C7 1.395(4) . ? C7 C8 1.509(4) . ? C8 N1 1.457(4) . ? C8 C10 1.539(4) . ? C9 O2 1.442(4) . ? C10 O3 1.429(4) . ? C10 C11 1.510(5) . ? C11 C12 1.391(5) . ? C11 C16 1.397(5) . ? C12 C13 1.389(5) . ? C13 C14 1.373(6) . ? C14 C15 1.379(6) . ? C15 C16 1.393(5) . ? C17 C18 1.599(8) . ? C18 O4 1.4275(11) . ? C19 O5 1.149(6) . ? C19 O4 1.4266(11) . ? C19 C20 1.528(7) . ? 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 O1 C1 N1 125.9(3) . . ? O1 C1 C2 127.9(3) . . ? N1 C1 C2 106.2(3) . . ? C7 C2 C3 122.5(3) . . ? C7 C2 C1 107.9(3) . . ? C3 C2 C1 129.6(3) . . ? C4 C3 C2 117.0(3) . . ? C3 C4 C5 121.8(3) . . ? C6 C5 C4 120.4(3) . . ? O2 C6 C5 125.6(3) . . ? O2 C6 C7 116.4(3) . . ? C5 C6 C7 118.0(3) . . ? C2 C7 C6 120.3(3) . . ? C2 C7 C8 110.4(3) . . ? C6 C7 C8 129.3(3) . . ? N1 C8 C7 101.2(3) . . ? N1 C8 C10 112.4(2) . . ? C7 C8 C10 113.1(3) . . ? O3 C10 C11 112.0(2) . . ? O3 C10 C8 105.9(2) . . ? C11 C10 C8 113.0(3) . . ? C12 C11 C16 118.6(3) . . ? C12 C11 C10 121.2(3) . . ? C16 C11 C10 120.2(3) . . ? C13 C12 C11 120.9(3) . . ? C14 C13 C12 120.0(4) . . ? C13 C14 C15 120.2(4) . . ? C14 C15 C16 120.3(4) . . ? C15 C16 C11 120.1(3) . . ? O4 C18 C17 102.6(5) . . ? O5 C19 O4 128.0(5) . . ? O5 C19 C20 123.9(5) . . ? O4 C19 C20 108.1(5) . . ? C1 N1 C8 114.3(3) . . ? C6 O2 C9 117.5(3) . . ? C19 O4 C18 107.61(11) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.504 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.061 # Attachment 'Comp_10.cif' data_ks0910 _database_code_depnum_ccdc_archive 'CCDC 762624' #TrackingRef 'Comp_10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 N O3' _chemical_formula_sum 'C15 H21 N O3' _chemical_formula_weight 263.33 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 Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.7517(5) _cell_length_b 13.5852(7) _cell_length_c 11.0154(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.266(3) _cell_angle_gamma 90.00 _cell_volume 1453.15(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1942 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9950 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5380 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3240 _reflns_number_gt 1942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0634P)^2^+0.7003P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3240 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1349 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.1875(3) 0.43755(18) 0.4924(2) 0.0284(6) Uani 1 1 d . . . C2 C 0.3293(3) 0.39884(18) 0.5141(2) 0.0280(6) Uani 1 1 d . . . C3 C 0.4007(3) 0.33829(19) 0.4403(2) 0.0332(7) Uani 1 1 d . . . H3 H 0.3585 0.3134 0.3654 0.040 Uiso 1 1 calc R . . C4 C 0.5353(3) 0.31575(19) 0.4799(3) 0.0343(7) Uani 1 1 d . . . H4 H 0.5864 0.2737 0.4320 0.041 Uiso 1 1 calc R . . C5 C 0.5980(3) 0.35361(19) 0.5894(2) 0.0326(7) Uani 1 1 d . . . H5 H 0.6916 0.3387 0.6139 0.039 Uiso 1 1 calc R . . C6 C 0.5237(3) 0.41304(19) 0.6624(2) 0.0294(6) Uani 1 1 d . . . C7 C 0.3880(3) 0.43521(18) 0.6244(2) 0.0265(6) Uani 1 1 d . . . C8 C 0.2834(3) 0.49812(19) 0.6828(2) 0.0266(6) Uani 1 1 d . . . H8 H 0.3185 0.5672 0.6911 0.032 Uiso 1 1 calc R . . C9 C 0.2413(3) 0.46207(18) 0.8087(2) 0.0266(6) Uani 1 1 d . . . C10 C 0.1139(3) 0.51682(19) 0.8437(2) 0.0283(6) Uani 1 1 d . . . H10A H 0.0959 0.4965 0.9270 0.034 Uiso 1 1 calc R . . H10B H 0.0339 0.4957 0.7878 0.034 Uiso 1 1 calc R . . C11 C 0.1220(3) 0.62922(19) 0.8403(2) 0.0298(6) Uani 1 1 d . . . H11A H 0.2142 0.6501 0.8762 0.036 Uiso 1 1 calc R . . H11B H 0.1116 0.6513 0.7543 0.036 Uiso 1 1 calc R . . C12 C 0.0135(3) 0.6789(2) 0.9086(3) 0.0365(7) Uani 1 1 d . . . H12A H -0.0786 0.6573 0.8732 0.044 Uiso 1 1 calc R . . H12B H 0.0246 0.6573 0.9947 0.044 Uiso 1 1 calc R . . C13 C 0.0200(3) 0.7899(2) 0.9046(3) 0.0446(8) Uani 1 1 d . . . H13A H 0.1128 0.8118 0.9341 0.067 Uiso 1 1 calc R . . H13B H -0.0468 0.8175 0.9565 0.067 Uiso 1 1 calc R . . H13C H -0.0019 0.8124 0.8205 0.067 Uiso 1 1 calc R . . C14 C 0.2164(3) 0.35154(19) 0.8074(3) 0.0359(7) Uani 1 1 d . . . H14A H 0.3023 0.3172 0.7947 0.054 Uiso 1 1 calc R . . H14B H 0.1461 0.3350 0.7412 0.054 Uiso 1 1 calc R . . H14C H 0.1848 0.3311 0.8855 0.054 Uiso 1 1 calc R . . C15 C 0.7187(3) 0.4401(2) 0.8102(3) 0.0415(7) Uani 1 1 d . . . H15A H 0.7401 0.3698 0.8193 0.062 Uiso 1 1 calc R . . H15B H 0.7405 0.4734 0.8886 0.062 Uiso 1 1 calc R . . H15C H 0.7737 0.4688 0.7491 0.062 Uiso 1 1 calc R . . N1 N 0.1669(2) 0.49494(15) 0.58935(18) 0.0290(5) Uani 1 1 d . . . H1 H 0.0900 0.5276 0.5956 0.035 Uiso 1 1 calc R . . O1 O 0.1037(2) 0.42242(14) 0.40318(16) 0.0349(5) Uani 1 1 d . . . O2 O 0.57539(19) 0.45208(14) 0.77193(16) 0.0365(5) Uani 1 1 d . . . O3 O 0.34724(19) 0.48755(13) 0.90182(15) 0.0312(5) Uani 1 1 d . . . H3A H 0.4244 0.4727 0.8788 0.047 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 C1 0.0326(16) 0.0261(13) 0.0273(15) 0.0013(11) 0.0062(12) -0.0009(12) C2 0.0323(16) 0.0245(13) 0.0277(15) 0.0031(11) 0.0048(11) -0.0020(11) C3 0.0417(18) 0.0280(14) 0.0304(15) -0.0022(11) 0.0058(12) 0.0001(13) C4 0.0406(18) 0.0250(14) 0.0389(16) -0.0009(11) 0.0115(13) 0.0052(12) C5 0.0332(17) 0.0293(15) 0.0358(16) 0.0035(12) 0.0061(12) 0.0054(12) C6 0.0341(16) 0.0269(14) 0.0271(15) 0.0013(11) 0.0018(12) -0.0015(12) C7 0.0300(16) 0.0217(12) 0.0283(14) 0.0014(10) 0.0050(11) -0.0007(11) C8 0.0277(15) 0.0253(13) 0.0269(14) 0.0005(10) 0.0022(11) -0.0008(11) C9 0.0295(15) 0.0236(13) 0.0269(14) -0.0016(10) 0.0032(11) -0.0012(11) C10 0.0303(16) 0.0308(14) 0.0245(14) -0.0001(11) 0.0068(11) -0.0020(12) C11 0.0321(16) 0.0271(13) 0.0308(15) -0.0010(11) 0.0065(12) 0.0024(12) C12 0.0350(17) 0.0321(15) 0.0438(17) -0.0040(13) 0.0109(13) 0.0034(13) C13 0.050(2) 0.0336(16) 0.0499(18) -0.0059(13) 0.0053(15) 0.0102(15) C14 0.0456(18) 0.0249(14) 0.0390(17) -0.0008(11) 0.0135(13) -0.0005(13) C15 0.0304(17) 0.0515(19) 0.0418(18) -0.0029(14) -0.0018(13) 0.0026(14) N1 0.0268(13) 0.0325(12) 0.0279(12) -0.0027(9) 0.0041(9) 0.0060(10) O1 0.0357(12) 0.0384(11) 0.0296(11) -0.0038(8) -0.0017(9) 0.0019(9) O2 0.0299(11) 0.0451(12) 0.0339(11) -0.0057(9) 0.0002(8) 0.0032(9) O3 0.0305(11) 0.0362(11) 0.0270(10) -0.0015(8) 0.0027(8) 0.0030(9) _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 C1 O1 1.237(3) . ? C1 N1 1.352(3) . ? C1 C2 1.478(4) . ? C2 C7 1.386(4) . ? C2 C3 1.388(4) . ? C3 C4 1.379(4) . ? C4 C5 1.399(4) . ? C5 C6 1.389(4) . ? C6 O2 1.371(3) . ? C6 C7 1.384(4) . ? C7 C8 1.518(4) . ? C8 N1 1.462(3) . ? C8 C9 1.561(4) . ? C9 O3 1.430(3) . ? C9 C14 1.521(3) . ? C9 C10 1.527(4) . ? C10 C11 1.530(4) . ? C11 C12 1.512(4) . ? C12 C13 1.510(4) . ? C15 O2 1.432(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 O1 C1 N1 126.1(2) . . ? O1 C1 C2 127.5(2) . . ? N1 C1 C2 106.4(2) . . ? C7 C2 C3 122.4(3) . . ? C7 C2 C1 108.6(2) . . ? C3 C2 C1 128.9(2) . . ? C4 C3 C2 117.4(3) . . ? C3 C4 C5 121.3(3) . . ? C6 C5 C4 120.2(3) . . ? O2 C6 C7 116.5(2) . . ? O2 C6 C5 124.4(2) . . ? C7 C6 C5 119.1(2) . . ? C6 C7 C2 119.6(2) . . ? C6 C7 C8 130.9(2) . . ? C2 C7 C8 109.4(2) . . ? N1 C8 C7 101.15(19) . . ? N1 C8 C9 111.5(2) . . ? C7 C8 C9 116.2(2) . . ? O3 C9 C14 110.5(2) . . ? O3 C9 C10 104.64(19) . . ? C14 C9 C10 110.5(2) . . ? O3 C9 C8 109.2(2) . . ? C14 C9 C8 110.9(2) . . ? C10 C9 C8 110.9(2) . . ? C9 C10 C11 115.8(2) . . ? C12 C11 C10 113.2(2) . . ? C13 C12 C11 113.5(2) . . ? C1 N1 C8 114.3(2) . . ? C6 O2 C15 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.245 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.063