# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Xiaodong Shi' _publ_contact_author_email XIAODONG.SHI@MAIL.WVU.EDU _publ_section_title ; One-Pot Cascade Michael-Michael-Aldol Condensation for Diastereo-Selective Synthesis of Nitro-Substituted Cyclohexanes ; loop_ _publ_author_name 'Xiaodong Shi' 'Novruz G Akhmedov' 'Yunfeng Chen' 'Jeffrey Petersen' 'Xiaohua Sun' 'Cheng Zhong' # Attachment '7g-ms38ccd-728930.cif' data_ms38ccd _database_code_depnum_ccdc_archive 'CCDC 728930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 N O4' _chemical_formula_weight 241.28 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 6.8860(4) _cell_length_b 9.8204(6) _cell_length_c 10.8548(7) _cell_angle_alpha 107.871(1) _cell_angle_beta 103.942(1) _cell_angle_gamma 101.569(1) _cell_volume 647.41(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3382 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4406 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2811 _reflns_number_gt 2318 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.0627P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2811 _refine_ls_number_parameters 187 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1766 _refine_ls_wR_factor_gt 0.1662 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.3619(2) 0.63011(16) 1.01309(11) 0.0806(4) Uani 1 1 d . . . O2 O 0.6372(2) 0.73238(17) 0.97990(13) 0.0859(4) Uani 1 1 d . . . O3 O 0.17775(18) 0.35066(13) 0.48752(9) 0.0655(3) Uani 1 1 d . . . H3 H 0.0549 0.3005 0.4626 0.098 Uiso 1 1 calc R . . O4 O -0.1626(2) 0.21279(17) 0.54793(13) 0.0888(5) Uani 1 1 d . . . N1 N 0.4502(2) 0.67265(14) 0.94189(11) 0.0573(3) Uani 1 1 d . A . C1 C 0.3166(2) 0.65695(15) 0.79683(12) 0.0489(3) Uani 1 1 d D . . C2 C 0.4489(2) 0.62748(17) 0.70272(14) 0.0564(4) Uani 1 1 d . A . H2A H 0.3780 0.6326 0.6162 0.068 Uiso 1 1 calc R . . H2B H 0.5822 0.7057 0.7437 0.068 Uiso 1 1 calc R . . C3 C 0.4893(2) 0.47605(18) 0.67563(15) 0.0572(4) Uani 1 1 d . . . H3A H 0.5731 0.4747 0.7608 0.069 Uiso 1 1 calc R A . H3B H 0.5693 0.4628 0.6128 0.069 Uiso 1 1 calc R . . C4 C 0.2883(2) 0.34621(16) 0.61565(13) 0.0520(3) Uani 1 1 d . A . C5 C 0.1624(2) 0.37284(15) 0.71599(12) 0.0475(3) Uani 1 1 d . . . H5 H 0.2450 0.3710 0.8024 0.057 Uiso 1 1 calc R A . C6 C 0.11966(19) 0.52526(15) 0.74619(13) 0.0492(3) Uani 1 1 d . A . H6A H 0.0253 0.5245 0.6635 0.059 Uiso 1 1 calc R . . H6B H 0.0496 0.5393 0.8147 0.059 Uiso 1 1 calc R . . C7 C 0.2754(14) 0.8067(7) 0.8211(9) 0.063(3) Uani 0.564(18) 1 d PD A 1 C8 C 0.3564(18) 0.9117(13) 0.7811(11) 0.078(2) Uani 0.564(18) 1 d PD A 1 H8A H 0.4496 0.8973 0.7324 0.093 Uiso 0.564(18) 1 calc PR A 1 H8B H 0.3205 1.0005 0.8014 0.093 Uiso 0.564(18) 1 calc PR A 1 C9 C 0.1217(14) 0.8449(10) 0.8959(13) 0.095(3) Uani 0.564(18) 1 d PD A 1 H9A H 0.1420 0.8121 0.9715 0.142 Uiso 0.564(18) 1 calc PR A 1 H9B H -0.0190 0.7955 0.8342 0.142 Uiso 0.564(18) 1 calc PR A 1 H9C H 0.1449 0.9513 0.9292 0.142 Uiso 0.564(18) 1 calc PR A 1 C7' C 0.2647(16) 0.8082(8) 0.8241(12) 0.055(4) Uani 0.436(18) 1 d PD A 2 C8' C 0.0936(18) 0.8173(15) 0.8557(15) 0.101(4) Uani 0.436(18) 1 d PD A 2 H8C H 0.0582 0.9062 0.8721 0.122 Uiso 0.436(18) 1 calc PR A 2 H8D H 0.0082 0.7348 0.8615 0.122 Uiso 0.436(18) 1 calc PR A 2 C9' C 0.4259(19) 0.9244(15) 0.8085(15) 0.080(3) Uani 0.436(18) 1 d PD A 2 H9D H 0.4196 0.8948 0.7144 0.120 Uiso 0.436(18) 1 calc PR A 2 H9E H 0.5629 0.9335 0.8641 0.120 Uiso 0.436(18) 1 calc PR A 2 H9F H 0.3979 1.0191 0.8371 0.120 Uiso 0.436(18) 1 calc PR A 2 C10 C 0.3353(3) 0.1976(2) 0.5931(2) 0.0737(5) Uani 1 1 d . . . H10A H 0.2069 0.1170 0.5466 0.110 Uiso 1 1 calc R A . H10B H 0.4023 0.1936 0.6799 0.110 Uiso 1 1 calc R . . H10C H 0.4266 0.1880 0.5387 0.110 Uiso 1 1 calc R . . C11 C -0.0466(2) 0.25186(17) 0.66331(15) 0.0582(4) Uani 1 1 d . A . C12 C -0.1053(3) 0.1855(3) 0.7597(2) 0.0966(7) Uani 1 1 d . . . H12A H -0.2400 0.1114 0.7143 0.145 Uiso 1 1 calc R A . H12B H -0.1116 0.2628 0.8370 0.145 Uiso 1 1 calc R . . H12C H -0.0025 0.1395 0.7902 0.145 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 0.0952(9) 0.1058(10) 0.0461(6) 0.0373(6) 0.0202(6) 0.0302(7) O2 0.0608(7) 0.1031(10) 0.0690(7) 0.0302(7) -0.0078(5) 0.0106(6) O3 0.0746(7) 0.0803(8) 0.0400(5) 0.0243(5) 0.0136(5) 0.0229(6) O4 0.0668(8) 0.0986(10) 0.0688(8) 0.0255(7) -0.0006(6) -0.0063(7) N1 0.0638(8) 0.0597(7) 0.0422(6) 0.0183(5) 0.0062(5) 0.0200(6) C1 0.0519(7) 0.0559(7) 0.0375(6) 0.0203(5) 0.0084(5) 0.0160(6) C2 0.0548(8) 0.0643(8) 0.0518(7) 0.0264(6) 0.0189(6) 0.0117(6) C3 0.0505(7) 0.0732(9) 0.0553(7) 0.0281(7) 0.0225(6) 0.0214(6) C4 0.0554(8) 0.0607(8) 0.0440(6) 0.0223(6) 0.0156(5) 0.0222(6) C5 0.0465(7) 0.0561(7) 0.0407(6) 0.0228(5) 0.0094(5) 0.0151(5) C6 0.0460(7) 0.0590(8) 0.0440(6) 0.0211(5) 0.0128(5) 0.0179(6) C7 0.061(5) 0.074(5) 0.041(4) 0.018(3) 0.005(3) 0.011(3) C8 0.091(5) 0.067(3) 0.087(5) 0.038(4) 0.034(4) 0.027(3) C9 0.108(5) 0.067(4) 0.137(7) 0.040(5) 0.073(6) 0.041(3) C7' 0.075(7) 0.038(4) 0.051(6) 0.019(4) 0.008(4) 0.027(4) C8' 0.110(5) 0.065(4) 0.113(6) 0.014(4) 0.010(5) 0.056(4) C9' 0.096(7) 0.051(3) 0.083(5) 0.028(3) 0.016(5) 0.013(4) C10 0.0784(11) 0.0687(10) 0.0800(11) 0.0256(8) 0.0294(9) 0.0337(9) C11 0.0520(8) 0.0601(8) 0.0624(8) 0.0255(7) 0.0154(6) 0.0162(6) C12 0.0657(11) 0.1225(17) 0.1127(16) 0.0768(15) 0.0235(10) 0.0057(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 O1 N1 1.2102(17) . ? O2 N1 1.2102(17) . ? O3 C4 1.4341(15) . ? O4 C11 1.2058(19) . ? N1 C1 1.5638(15) . ? C1 C7 1.510(6) . ? C1 C6 1.5215(19) . ? C1 C2 1.5262(19) . ? C1 C7' 1.554(5) . ? C2 C3 1.521(2) . ? C3 C4 1.521(2) . ? C4 C10 1.518(2) . ? C4 C5 1.5422(18) . ? C5 C11 1.5199(19) . ? C5 C6 1.5351(18) . ? C7 C8 1.313(7) . ? C7 C9 1.518(8) . ? C7' C8' 1.316(9) . ? C7' C9' 1.504(9) . ? C11 C12 1.483(2) . ? 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 N1 O1 122.89(13) . . ? O2 N1 C1 118.18(12) . . ? O1 N1 C1 118.86(12) . . ? C7 C1 C6 114.0(4) . . ? C7 C1 C2 112.5(3) . . ? C6 C1 C2 110.40(11) . . ? C7 C1 C7' 2.9(7) . . ? C6 C1 C7' 111.6(4) . . ? C2 C1 C7' 115.2(4) . . ? C7 C1 N1 103.6(4) . . ? C6 C1 N1 108.25(10) . . ? C2 C1 N1 107.58(11) . . ? C7' C1 N1 103.3(4) . . ? C3 C2 C1 113.16(11) . . ? C2 C3 C4 112.73(11) . . ? O3 C4 C10 110.22(12) . . ? O3 C4 C3 106.03(11) . . ? C10 C4 C3 111.12(12) . . ? O3 C4 C5 110.91(11) . . ? C10 C4 C5 110.72(12) . . ? C3 C4 C5 107.73(11) . . ? C11 C5 C6 108.11(10) . . ? C11 C5 C4 112.17(11) . . ? C6 C5 C4 112.30(10) . . ? C1 C6 C5 113.61(10) . . ? C8 C7 C1 126.7(8) . . ? C8 C7 C9 113.8(8) . . ? C1 C7 C9 119.4(6) . . ? C8' C7' C9' 129.8(10) . . ? C8' C7' C1 118.0(8) . . ? C9' C7' C1 112.1(8) . . ? O4 C11 C12 120.99(16) . . ? O4 C11 C5 121.31(14) . . ? C12 C11 C5 117.69(14) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.267 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.047 # Attachment '4a-ms53ccd-728931.cif' data_ms53ccd _database_code_depnum_ccdc_archive 'CCDC 728931' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N O4' _chemical_formula_weight 289.32 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' 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.4068(11) _cell_length_b 6.3085(5) _cell_length_c 16.3698(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.3340(10) _cell_angle_gamma 90.00 _cell_volume 1472.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5018 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9842 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3351 _reflns_number_gt 2425 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.3489P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3351 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1454 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.89119(12) -0.0994(2) 0.44160(11) 0.0748(5) Uani 1 1 d . . . O2 O 0.91668(10) 0.1783(2) 0.37402(10) 0.0707(5) Uani 1 1 d . . . O3 O 0.78703(9) 0.4614(2) 0.63701(8) 0.0585(4) Uani 1 1 d . . . H3O H 0.7895 0.4717 0.6872 0.088 Uiso 1 1 calc R . . O4 O 0.72677(13) -0.0045(3) 0.68805(10) 0.0883(6) Uani 1 1 d . . . N1 N 0.87266(10) 0.0811(2) 0.41939(9) 0.0464(4) Uani 1 1 d . . . C1 C 0.78648(11) 0.1907(2) 0.44764(9) 0.0370(3) Uani 1 1 d . . . C2 C 0.76343(12) 0.0815(3) 0.52592(9) 0.0413(4) Uani 1 1 d . . . H2A H 0.7544 -0.0686 0.5147 0.050 Uiso 1 1 calc R . . H2B H 0.7047 0.1380 0.5389 0.050 Uiso 1 1 calc R . . C3 C 0.83865(12) 0.1081(3) 0.60167(10) 0.0430(4) Uani 1 1 d . . . H3 H 0.8947 0.0302 0.5914 0.052 Uiso 1 1 calc R . . C4 C 0.86673(11) 0.3445(3) 0.61852(10) 0.0428(4) Uani 1 1 d . . . C5 C 0.89238(12) 0.4395(3) 0.53971(10) 0.0431(4) Uani 1 1 d . . . H5A H 0.9478 0.3683 0.5260 0.052 Uiso 1 1 calc R . . H5B H 0.9080 0.5879 0.5492 0.052 Uiso 1 1 calc R . . C6 C 0.81418(12) 0.4220(2) 0.46659(10) 0.0423(4) Uani 1 1 d . . . H6A H 0.8348 0.4856 0.4183 0.051 Uiso 1 1 calc R . . H6B H 0.7598 0.5001 0.4787 0.051 Uiso 1 1 calc R . . C7 C 0.70555(12) 0.1651(3) 0.37630(10) 0.0419(4) Uani 1 1 d . . . C8 C 0.70867(16) 0.0358(4) 0.31309(13) 0.0660(6) Uani 1 1 d . . . H8A H 0.6568 0.0228 0.2723 0.079 Uiso 1 1 calc R . . H8B H 0.7627 -0.0422 0.3094 0.079 Uiso 1 1 calc R . . C9 C 0.61814(12) 0.2899(3) 0.38166(10) 0.0448(4) Uani 1 1 d . . . C10 C 0.60751(15) 0.4936(3) 0.34967(13) 0.0599(5) Uani 1 1 d . . . H10 H 0.6565 0.5562 0.3272 0.072 Uiso 1 1 calc R . . C11 C 0.52464(18) 0.6047(4) 0.35089(16) 0.0770(7) Uani 1 1 d . . . H11 H 0.5186 0.7412 0.3293 0.092 Uiso 1 1 calc R . . C12 C 0.45211(17) 0.5156(5) 0.38335(15) 0.0831(8) Uani 1 1 d . . . H12 H 0.3967 0.5908 0.3840 0.100 Uiso 1 1 calc R . . C13 C 0.46107(15) 0.3142(5) 0.41509(14) 0.0785(7) Uani 1 1 d . . . H13 H 0.4115 0.2529 0.4371 0.094 Uiso 1 1 calc R . . C14 C 0.54358(13) 0.2012(4) 0.41455(12) 0.0596(5) Uani 1 1 d . . . H14 H 0.5490 0.0650 0.4364 0.071 Uiso 1 1 calc R . . C15 C 0.80511(16) 0.0135(4) 0.67691(12) 0.0632(6) Uani 1 1 d . . . H15 H 0.8510 -0.0352 0.7185 0.076 Uiso 1 1 calc R . . C16 C 0.94914(14) 0.3655(4) 0.68837(12) 0.0594(5) Uani 1 1 d . . . H16A H 0.9667 0.5119 0.6952 0.089 Uiso 1 1 calc R . . H16B H 1.0015 0.2851 0.6750 0.089 Uiso 1 1 calc R . . H16C H 0.9310 0.3126 0.7387 0.089 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 0.0910(12) 0.0567(8) 0.0827(11) 0.0069(7) 0.0323(9) 0.0282(8) O2 0.0683(9) 0.0781(9) 0.0758(10) -0.0042(8) 0.0448(8) -0.0081(7) O3 0.0491(8) 0.0781(9) 0.0506(7) -0.0127(7) 0.0150(6) 0.0134(6) O4 0.0806(12) 0.1322(16) 0.0572(9) 0.0211(10) 0.0267(8) -0.0234(11) N1 0.0471(8) 0.0512(8) 0.0433(8) -0.0038(6) 0.0153(6) 0.0017(6) C1 0.0398(8) 0.0385(7) 0.0350(7) 0.0014(6) 0.0130(6) 0.0009(6) C2 0.0435(9) 0.0466(8) 0.0355(8) 0.0042(6) 0.0110(6) -0.0051(7) C3 0.0391(8) 0.0532(9) 0.0375(8) 0.0071(7) 0.0082(6) 0.0007(7) C4 0.0350(8) 0.0561(9) 0.0386(8) -0.0036(7) 0.0102(6) 0.0014(7) C5 0.0424(9) 0.0435(8) 0.0445(9) -0.0015(7) 0.0105(7) -0.0051(7) C6 0.0502(9) 0.0379(7) 0.0398(8) 0.0019(6) 0.0104(7) -0.0013(7) C7 0.0466(9) 0.0454(8) 0.0349(8) 0.0019(7) 0.0100(6) -0.0035(7) C8 0.0624(12) 0.0812(14) 0.0526(12) -0.0208(10) 0.0023(9) 0.0046(11) C9 0.0430(9) 0.0568(10) 0.0339(8) -0.0043(7) 0.0040(6) -0.0023(7) C10 0.0557(11) 0.0640(11) 0.0592(12) 0.0043(9) 0.0052(9) 0.0048(9) C11 0.0754(16) 0.0773(14) 0.0718(15) -0.0097(12) -0.0115(12) 0.0248(12) C12 0.0538(13) 0.132(2) 0.0598(14) -0.0355(15) -0.0056(11) 0.0272(15) C13 0.0429(11) 0.139(2) 0.0552(12) -0.0191(15) 0.0109(9) -0.0090(13) C14 0.0495(11) 0.0835(14) 0.0462(10) -0.0030(9) 0.0088(8) -0.0108(10) C15 0.0644(13) 0.0815(14) 0.0431(10) 0.0177(10) 0.0060(9) -0.0135(11) C16 0.0506(11) 0.0798(13) 0.0460(10) -0.0034(9) 0.0004(8) -0.0064(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 O1 N1 1.213(2) . ? O2 N1 1.2109(19) . ? O3 C4 1.433(2) . ? O4 C15 1.175(3) . ? N1 C1 1.549(2) . ? C1 C6 1.532(2) . ? C1 C2 1.533(2) . ? C1 C7 1.535(2) . ? C2 C3 1.533(2) . ? C3 C15 1.510(2) . ? C3 C4 1.559(2) . ? C4 C5 1.516(2) . ? C4 C16 1.530(2) . ? C5 C6 1.524(2) . ? C7 C8 1.323(3) . ? C7 C9 1.499(2) . ? C9 C10 1.387(3) . ? C9 C14 1.387(3) . ? C10 C11 1.387(3) . ? C11 C12 1.361(4) . ? C12 C13 1.371(4) . ? C13 C14 1.387(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 O2 N1 O1 123.17(16) . . ? O2 N1 C1 118.07(14) . . ? O1 N1 C1 118.72(14) . . ? C6 C1 C2 109.89(13) . . ? C6 C1 C7 113.67(13) . . ? C2 C1 C7 110.85(13) . . ? C6 C1 N1 106.80(13) . . ? C2 C1 N1 109.21(13) . . ? C7 C1 N1 106.21(12) . . ? C1 C2 C3 114.43(13) . . ? C15 C3 C2 110.14(14) . . ? C15 C3 C4 109.83(15) . . ? C2 C3 C4 112.48(13) . . ? O3 C4 C5 106.12(14) . . ? O3 C4 C16 110.86(14) . . ? C5 C4 C16 110.07(14) . . ? O3 C4 C3 109.52(13) . . ? C5 C4 C3 108.46(13) . . ? C16 C4 C3 111.62(15) . . ? C4 C5 C6 113.33(14) . . ? C5 C6 C1 111.66(13) . . ? C8 C7 C9 119.59(16) . . ? C8 C7 C1 123.50(16) . . ? C9 C7 C1 116.88(13) . . ? C10 C9 C14 118.08(18) . . ? C10 C9 C7 120.82(16) . . ? C14 C9 C7 121.00(17) . . ? C11 C10 C9 120.7(2) . . ? C12 C11 C10 120.5(2) . . ? C11 C12 C13 119.7(2) . . ? C12 C13 C14 120.5(2) . . ? C13 C14 C9 120.5(2) . . ? O4 C15 C3 126.39(19) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.305 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.046 # Attachment '7a-ms54ccd-728932.cif' data_ms54ccd _database_code_depnum_ccdc_archive 'CCDC 728932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 N O4' _chemical_formula_weight 303.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 11.6190(11) _cell_length_b 12.2992(12) _cell_length_c 11.3746(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1625.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6689 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10526 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3623 _reflns_number_gt 3086 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.0897P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3623 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.32263(12) 0.54749(13) 0.2369(2) 0.0858(5) Uani 1 1 d . . . O2 O 0.19031(15) 0.42960(12) 0.26068(18) 0.0812(5) Uani 1 1 d . . . O3 O 0.17381(11) 0.74105(12) -0.08264(13) 0.0662(4) Uani 1 1 d . . . H3O H 0.2051 0.8006 -0.0883 0.099 Uiso 1 1 calc R . . O4 O 0.21178(14) 0.94128(13) 0.04204(16) 0.0782(5) Uani 1 1 d . . . N1 N 0.22247(13) 0.51933(13) 0.23239(17) 0.0556(4) Uani 1 1 d . . . C1 C 0.13060(13) 0.60107(14) 0.18521(15) 0.0449(4) Uani 1 1 d . . . C2 C 0.18651(13) 0.71247(14) 0.17200(16) 0.0432(3) Uani 1 1 d . . . H2A H 0.2557 0.7064 0.1247 0.052 Uiso 1 1 calc R . . H2B H 0.2080 0.7403 0.2487 0.052 Uiso 1 1 calc R . . C3 C 0.10148(12) 0.79067(14) 0.11281(15) 0.0428(3) Uani 1 1 d . . . H3 H 0.0302 0.7900 0.1589 0.051 Uiso 1 1 calc R . . C4 C 0.07173(15) 0.75121(16) -0.01352(16) 0.0511(4) Uani 1 1 d . . . C5 C 0.02140(16) 0.63791(17) -0.00359(17) 0.0560(4) Uani 1 1 d . . . H5A H 0.0073 0.6099 -0.0820 0.067 Uiso 1 1 calc R . . H5B H -0.0521 0.6424 0.0366 0.067 Uiso 1 1 calc R . . C6 C 0.09914(16) 0.55769(16) 0.06264(17) 0.0550(4) Uani 1 1 d . . . H6A H 0.1689 0.5456 0.0177 0.066 Uiso 1 1 calc R . . H6B H 0.0598 0.4885 0.0706 0.066 Uiso 1 1 calc R . . C7 C 0.03234(13) 0.60231(13) 0.27470(15) 0.0441(3) Uani 1 1 d . . . C8 C -0.06549(16) 0.54897(18) 0.2570(2) 0.0620(5) Uani 1 1 d . . . H8A H -0.1245 0.5536 0.3120 0.074 Uiso 1 1 calc R . . H8B H -0.0750 0.5070 0.1897 0.074 Uiso 1 1 calc R . . C9 C 0.04696(13) 0.66953(14) 0.38306(15) 0.0447(3) Uani 1 1 d . . . C10 C -0.03200(15) 0.75012(17) 0.4090(2) 0.0631(5) Uani 1 1 d . . . H10 H -0.0942 0.7613 0.3589 0.076 Uiso 1 1 calc R . . C11 C -0.0202(2) 0.8146(2) 0.5081(3) 0.0813(7) Uani 1 1 d . . . H11 H -0.0739 0.8688 0.5237 0.098 Uiso 1 1 calc R . . C12 C 0.0709(2) 0.7986(2) 0.5839(2) 0.0791(7) Uani 1 1 d . . . H12 H 0.0792 0.8420 0.6503 0.095 Uiso 1 1 calc R . . C13 C 0.14898(19) 0.7184(2) 0.5603(2) 0.0724(6) Uani 1 1 d . . . H13 H 0.2098 0.7066 0.6119 0.087 Uiso 1 1 calc R . . C14 C 0.13884(16) 0.65419(16) 0.46035(19) 0.0576(5) Uani 1 1 d . . . H14 H 0.1935 0.6008 0.4449 0.069 Uiso 1 1 calc R . . C15 C 0.15127(14) 0.90490(15) 0.11924(18) 0.0511(4) Uani 1 1 d . . . C16 C 0.12487(17) 0.96968(17) 0.2265(2) 0.0656(5) Uani 1 1 d . . . H16A H 0.1703 1.0349 0.2265 0.098 Uiso 1 1 calc R . . H16B H 0.1426 0.9275 0.2952 0.098 Uiso 1 1 calc R . . H16C H 0.0447 0.9884 0.2270 0.098 Uiso 1 1 calc R . . C17 C -0.01398(18) 0.8279(2) -0.0725(2) 0.0698(6) Uani 1 1 d . . . H17A H 0.0206 0.8983 -0.0818 0.105 Uiso 1 1 calc R . . H17B H -0.0816 0.8342 -0.0244 0.105 Uiso 1 1 calc R . . H17C H -0.0348 0.7995 -0.1481 0.105 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 0.0512(7) 0.0755(10) 0.1305(16) 0.0006(10) -0.0156(9) 0.0131(7) O2 0.0849(10) 0.0548(8) 0.1041(14) 0.0172(8) -0.0078(9) 0.0134(7) O3 0.0649(7) 0.0847(10) 0.0491(8) -0.0005(7) 0.0140(7) -0.0039(7) O4 0.0850(9) 0.0720(9) 0.0775(11) 0.0120(8) 0.0188(9) -0.0255(8) N1 0.0578(8) 0.0484(8) 0.0605(9) -0.0046(7) -0.0071(7) 0.0117(7) C1 0.0441(7) 0.0440(9) 0.0466(9) -0.0012(7) -0.0059(7) 0.0030(6) C2 0.0393(6) 0.0474(8) 0.0430(8) -0.0011(7) -0.0007(6) -0.0013(6) C3 0.0392(6) 0.0462(8) 0.0429(9) 0.0041(7) 0.0024(6) -0.0007(6) C4 0.0496(8) 0.0668(11) 0.0370(9) 0.0063(8) 0.0004(7) -0.0036(8) C5 0.0587(9) 0.0688(12) 0.0403(9) -0.0034(8) -0.0085(7) -0.0064(8) C6 0.0650(9) 0.0514(10) 0.0485(10) -0.0087(8) -0.0054(8) -0.0022(8) C7 0.0438(7) 0.0439(7) 0.0445(9) 0.0077(7) -0.0054(6) 0.0015(6) C8 0.0544(9) 0.0726(12) 0.0590(12) 0.0085(9) -0.0065(8) -0.0144(9) C9 0.0443(7) 0.0485(8) 0.0414(8) 0.0082(7) 0.0004(6) 0.0007(7) C10 0.0517(9) 0.0787(13) 0.0591(12) -0.0006(11) 0.0008(9) 0.0183(9) C11 0.0810(14) 0.0879(17) 0.0749(15) -0.0156(13) 0.0104(13) 0.0260(13) C12 0.0868(14) 0.0927(17) 0.0578(13) -0.0201(12) 0.0047(11) 0.0045(12) C13 0.0695(11) 0.0961(16) 0.0515(12) -0.0061(11) -0.0132(10) 0.0074(11) C14 0.0554(9) 0.0672(12) 0.0503(10) 0.0000(9) -0.0071(8) 0.0147(9) C15 0.0450(7) 0.0481(9) 0.0602(11) 0.0076(8) -0.0003(7) -0.0005(7) C16 0.0622(10) 0.0518(10) 0.0829(14) -0.0086(10) 0.0059(10) -0.0029(8) C17 0.0677(11) 0.0861(14) 0.0554(12) 0.0185(11) -0.0095(10) 0.0021(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 O1 N1 1.215(2) . ? O2 N1 1.209(2) . ? O3 C4 1.429(2) . ? O4 C15 1.211(2) . ? N1 C1 1.561(2) . ? C1 C2 1.524(2) . ? C1 C7 1.530(2) . ? C1 C6 1.537(3) . ? C2 C3 1.534(2) . ? C3 C15 1.521(2) . ? C3 C4 1.556(3) . ? C4 C5 1.515(3) . ? C4 C17 1.527(3) . ? C5 C6 1.535(3) . ? C7 C8 1.328(2) . ? C7 C9 1.494(2) . ? C9 C10 1.382(2) . ? C9 C14 1.396(2) . ? C10 C11 1.386(4) . ? C11 C12 1.379(4) . ? C12 C13 1.367(3) . ? C13 C14 1.389(3) . ? C15 C16 1.489(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 O2 N1 O1 123.03(16) . . ? O2 N1 C1 117.90(15) . . ? O1 N1 C1 119.05(16) . . ? C2 C1 C7 112.01(14) . . ? C2 C1 C6 108.91(14) . . ? C7 C1 C6 115.44(13) . . ? C2 C1 N1 108.74(12) . . ? C7 C1 N1 106.74(14) . . ? C6 C1 N1 104.53(14) . . ? C1 C2 C3 109.41(12) . . ? C15 C3 C2 108.23(13) . . ? C15 C3 C4 114.65(14) . . ? C2 C3 C4 110.66(15) . . ? O3 C4 C5 106.32(16) . . ? O3 C4 C17 110.73(16) . . ? C5 C4 C17 110.44(15) . . ? O3 C4 C3 110.56(13) . . ? C5 C4 C3 107.68(14) . . ? C17 C4 C3 110.96(17) . . ? C4 C5 C6 113.61(15) . . ? C5 C6 C1 111.22(15) . . ? C8 C7 C9 119.72(17) . . ? C8 C7 C1 122.23(17) . . ? C9 C7 C1 118.01(13) . . ? C10 C9 C14 118.06(18) . . ? C10 C9 C7 119.81(16) . . ? C14 C9 C7 122.13(15) . . ? C9 C10 C11 121.22(19) . . ? C12 C11 C10 120.2(2) . . ? C13 C12 C11 119.3(2) . . ? C12 C13 C14 121.0(2) . . ? C13 C14 C9 120.22(18) . . ? O4 C15 C16 121.07(18) . . ? O4 C15 C3 121.83(19) . . ? C16 C15 C3 117.08(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.243 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.034 # Attachment '7f-ms93ccd-728933.cif' data_ms93ccd _database_code_depnum_ccdc_archive 'CCDC 728933' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 N O4' _chemical_formula_weight 405.48 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 9.6784(6) _cell_length_b 14.8547(10) _cell_length_c 16.1677(11) _cell_angle_alpha 84.2340(10) _cell_angle_beta 75.4250(10) _cell_angle_gamma 72.6650(10) _cell_volume 2146.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7308 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 15150 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0757 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.54 _reflns_number_total 9495 _reflns_number_gt 6743 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0964P)^2^+0.2843P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9495 _refine_ls_number_parameters 633 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1950 _refine_ls_wR_factor_gt 0.1752 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.071 _refine_ls_shift/su_mean 0.005 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 0.81341(5) 0.86536(3) 1.01231(4) 0.05037(15) Uani 1 1 d . . . H1 H 0.7978 0.8941 0.9680 0.076 Uiso 1 1 calc R . . O2 O 0.83563(7) 0.85063(4) 0.84186(4) 0.07116(19) Uani 1 1 d . . . O3 O 0.83633(6) 0.51615(4) 1.00155(4) 0.05913(17) Uani 1 1 d . . . O4 O 0.85808(7) 0.51498(4) 1.13076(4) 0.0668(2) Uani 1 1 d . . . O5 O 0.30667(5) 1.04008(4) 0.70262(5) 0.0734(2) Uani 1 1 d . . . H5 H 0.2622 1.0634 0.7492 0.110 Uiso 1 1 calc R . . O6 O 0.03539(6) 1.09998(4) 0.81071(4) 0.06639(17) Uani 1 1 d . . . O7 O 0.19031(11) 0.88219(7) 0.46276(5) 0.1135(3) Uani 1 1 d . . . O8 O -0.00775(7) 0.90328(5) 0.56197(4) 0.0779(2) Uani 1 1 d . . . N1 N 0.81267(6) 0.55512(4) 1.06887(4) 0.04615(17) Uani 1 1 d . . . N2 N 0.12468(8) 0.88885(5) 0.53810(4) 0.0624(2) Uani 1 1 d . . . C1 C 0.92082(7) 0.77556(5) 0.99206(5) 0.04192(18) Uani 1 1 d . . . C2 C 0.86364(7) 0.71887(4) 0.93945(4) 0.03918(17) Uani 1 1 d . . . H2 H 0.9365 0.6569 0.9283 0.047 Uiso 1 1 calc R . . C3 C 0.71293(7) 0.70436(5) 0.98976(4) 0.04155(18) Uani 1 1 d . . . H3A H 0.6382 0.7651 0.9953 0.050 Uiso 1 1 calc R . . H3B H 0.6837 0.6650 0.9569 0.050 Uiso 1 1 calc R . . C4 C 0.71373(7) 0.65924(5) 1.07871(4) 0.04073(18) Uani 1 1 d . . . C5 C 0.78213(7) 0.70985(5) 1.12827(5) 0.04527(19) Uani 1 1 d . . . H5A H 0.7965 0.6739 1.1804 0.054 Uiso 1 1 calc R . . H5B H 0.7130 0.7712 1.1443 0.054 Uiso 1 1 calc R . . C6 C 0.93131(7) 0.72332(5) 1.07749(5) 0.04515(18) Uani 1 1 d . . . H6A H 0.9663 0.7584 1.1113 0.054 Uiso 1 1 calc R . . H6B H 1.0039 0.6620 1.0671 0.054 Uiso 1 1 calc R . . C7 C 1.07355(7) 0.78828(5) 0.94604(5) 0.04578(19) Uani 1 1 d . . . C8 C 1.19325(9) 0.71151(7) 0.91614(7) 0.0706(3) Uani 1 1 d . . . H8 H 1.1802 0.6515 0.9213 0.085 Uiso 1 1 calc R . . C9 C 1.33286(10) 0.72345(8) 0.87848(8) 0.0870(4) Uani 1 1 d . . . H9 H 1.4123 0.6713 0.8587 0.104 Uiso 1 1 calc R . . C10 C 1.35449(9) 0.81150(8) 0.87021(7) 0.0777(3) Uani 1 1 d . . . H10 H 1.4477 0.8193 0.8444 0.093 Uiso 1 1 calc R . . C11 C 1.23726(9) 0.88767(7) 0.90035(6) 0.0691(2) Uani 1 1 d . . . H11 H 1.2514 0.9474 0.8956 0.083 Uiso 1 1 calc R . . C12 C 1.09750(8) 0.87664(5) 0.93787(5) 0.0551(2) Uani 1 1 d . . . H12 H 1.0188 0.9291 0.9578 0.066 Uiso 1 1 calc R . . C13 C 0.84218(7) 0.76757(5) 0.85421(5) 0.04570(19) Uani 1 1 d . . . C14 C 0.82758(8) 0.71437(6) 0.78487(5) 0.0511(2) Uani 1 1 d . . . C15 C 0.78885(12) 0.76555(7) 0.71311(6) 0.0757(3) Uani 1 1 d . . . H15 H 0.7697 0.8308 0.7107 0.091 Uiso 1 1 calc R . . C16 C 0.77878(16) 0.72027(10) 0.64579(7) 0.1073(5) Uani 1 1 d . . . H16 H 0.7528 0.7547 0.5980 0.129 Uiso 1 1 calc R . . C17 C 0.80734(16) 0.62357(10) 0.64944(7) 0.1099(5) Uani 1 1 d . . . H17 H 0.8007 0.5930 0.6037 0.132 Uiso 1 1 calc R . . C18 C 0.84555(13) 0.57171(8) 0.71980(7) 0.0862(4) Uani 1 1 d . . . H18 H 0.8650 0.5064 0.7215 0.103 Uiso 1 1 calc R . . C19 C 0.85492(10) 0.61693(6) 0.78800(5) 0.0610(3) Uani 1 1 d . . . H19 H 0.8795 0.5821 0.8360 0.073 Uiso 1 1 calc R . . C20 C 0.55931(7) 0.65034(5) 1.12569(5) 0.0473(2) Uani 1 1 d . . . C21 C 0.47953(9) 0.61112(8) 1.07691(7) 0.0801(3) Uani 1 1 d . . . H21A H 0.5483 0.5554 1.0479 0.096 Uiso 1 1 calc R . . H21B H 0.4481 0.6573 1.0336 0.096 Uiso 1 1 calc R . . C22 C 0.34391(10) 0.58494(8) 1.13225(8) 0.0905(4) Uani 1 1 d . . . H22A H 0.2830 0.5761 1.0961 0.109 Uiso 1 1 calc R . . H22B H 0.3760 0.5259 1.1631 0.109 Uiso 1 1 calc R . . C23 C 0.25376(9) 0.66050(7) 1.19454(8) 0.0779(3) Uani 1 1 d . . . H23A H 0.2206 0.7193 1.1637 0.093 Uiso 1 1 calc R . . H23B H 0.1664 0.6435 1.2280 0.093 Uiso 1 1 calc R . . C24 C 0.34368(10) 0.67353(8) 1.25293(7) 0.0787(3) Uani 1 1 d . . . H24A H 0.3525 0.6216 1.2946 0.094 Uiso 1 1 calc R . . H24B H 0.2919 0.7314 1.2837 0.094 Uiso 1 1 calc R . . C25 C 0.49781(9) 0.67794(6) 1.20560(6) 0.0603(3) Uani 1 1 d . . . H25 H 0.5522 0.7011 1.2338 0.072 Uiso 1 1 calc R . . C26 C 0.21130(7) 1.06816(5) 0.64423(6) 0.0518(2) Uani 1 1 d . . . C27 C 0.07480(6) 1.02951(5) 0.67724(4) 0.04032(17) Uani 1 1 d . . . H27 H 0.0126 1.0474 0.6355 0.048 Uiso 1 1 calc R . . C28 C 0.12326(7) 0.92071(5) 0.68675(4) 0.04210(18) Uani 1 1 d . . . H28A H 0.1766 0.9028 0.7320 0.051 Uiso 1 1 calc R . . H28B H 0.0349 0.8989 0.7040 0.051 Uiso 1 1 calc R . . C29 C 0.22212(8) 0.87075(5) 0.60530(5) 0.0492(2) Uani 1 1 d . A . C30 C 0.35123(9) 0.91324(6) 0.56925(7) 0.0717(3) Uani 1 1 d . . . H30A H 0.4195 0.8957 0.6068 0.086 Uiso 1 1 calc R . . H30B H 0.4048 0.8869 0.5138 0.086 Uiso 1 1 calc R . . C31 C 0.30065(9) 1.02053(6) 0.55954(7) 0.0695(3) Uani 1 1 d . . . H31A H 0.2397 1.0380 0.5179 0.083 Uiso 1 1 calc R . . H31B H 0.3873 1.0435 0.5379 0.083 Uiso 1 1 calc R . . C32 C 0.17153(8) 1.17490(5) 0.62867(5) 0.0551(2) Uani 1 1 d . . . C33 C 0.04609(10) 1.22590(6) 0.60107(7) 0.0684(3) Uani 1 1 d . . . H33 H -0.0212 1.1951 0.5946 0.082 Uiso 1 1 calc R . . C34 C 0.01809(13) 1.32193(7) 0.58276(8) 0.0827(4) Uani 1 1 d . . . H34 H -0.0673 1.3550 0.5644 0.099 Uiso 1 1 calc R . . C35 C 0.11731(13) 1.36814(7) 0.59183(7) 0.0891(4) Uani 1 1 d . . . H35 H 0.0992 1.4326 0.5800 0.107 Uiso 1 1 calc R . . C36 C 0.24318(13) 1.31791(8) 0.61847(9) 0.1014(4) Uani 1 1 d . . . H36 H 0.3115 1.3485 0.6236 0.122 Uiso 1 1 calc R . . C37 C 0.26924(10) 1.22357(7) 0.63750(8) 0.0830(3) Uani 1 1 d . . . H37 H 0.3540 1.1912 0.6568 0.100 Uiso 1 1 calc R . . C38 C -0.01896(7) 1.06898(5) 0.76306(4) 0.04267(18) Uani 1 1 d . . . C39 C -0.17565(7) 1.06507(5) 0.79219(4) 0.04068(18) Uani 1 1 d . . . C40 C -0.24683(9) 1.08022(5) 0.87818(5) 0.0524(2) Uani 1 1 d . . . H40 H -0.1972 1.0946 0.9152 0.063 Uiso 1 1 calc R . . C41 C -0.38990(9) 1.07406(6) 0.90864(6) 0.0676(3) Uani 1 1 d . . . H41 H -0.4359 1.0831 0.9663 0.081 Uiso 1 1 calc R . . C42 C -0.46482(9) 1.05465(7) 0.85447(7) 0.0706(3) Uani 1 1 d . . . H42 H -0.5616 1.0507 0.8755 0.085 Uiso 1 1 calc R . . C43 C -0.39768(8) 1.04075(6) 0.76852(6) 0.0627(3) Uani 1 1 d . . . H43 H -0.4498 1.0286 0.7318 0.075 Uiso 1 1 calc R . . C44 C -0.25195(7) 1.04505(5) 0.73732(5) 0.0472(2) Uani 1 1 d . . . H44 H -0.2057 1.0346 0.6799 0.057 Uiso 1 1 calc R . . C45 C 0.27217(8) 0.76327(6) 0.61659(5) 0.0544(2) Uani 1 1 d D . . C46 C 0.2016(3) 0.71741(19) 0.67372(19) 0.0883(10) Uani 0.33 1 d PDU A 1 H46A H 0.1142 0.7511 0.7098 0.106 Uiso 0.33 1 calc PR A 1 C47 C 0.2503(4) 0.6136(2) 0.6862(3) 0.1263(14) Uani 0.33 1 d PDU A 1 H47A H 0.1770 0.5872 0.6744 0.152 Uiso 0.33 1 calc PR A 1 H47B H 0.2542 0.5987 0.7455 0.152 Uiso 0.33 1 calc PR A 1 C48 C 0.3993(3) 0.5679(2) 0.6304(2) 0.0916(13) Uani 0.33 1 d PDU A 1 H48A H 0.4236 0.4996 0.6336 0.110 Uiso 0.33 1 calc PR A 1 H48B H 0.4784 0.5880 0.6428 0.110 Uiso 0.33 1 calc PR A 1 C49 C 0.3641(8) 0.6082(3) 0.5461(3) 0.162(3) Uani 0.33 1 d PDU A 1 H49A H 0.4526 0.5849 0.5012 0.194 Uiso 0.33 1 calc PR A 1 H49B H 0.2877 0.5830 0.5367 0.194 Uiso 0.33 1 calc PR A 1 C50 C 0.3128(8) 0.7133(3) 0.5354(3) 0.190(3) Uani 0.33 1 d PDU A 1 H50A H 0.3914 0.7344 0.4960 0.228 Uiso 0.33 1 calc PR A 1 H50B H 0.2271 0.7303 0.5103 0.228 Uiso 0.33 1 calc PR A 1 C46A C 0.1686(3) 0.7115(2) 0.6394(3) 0.1044(15) Uani 0.33 1 d PDU A 2 H46B H 0.0681 0.7412 0.6605 0.125 Uiso 0.33 1 calc PR A 2 C47A C 0.2236(3) 0.6063(2) 0.6292(3) 0.1094(15) Uani 0.33 1 d PDU A 2 H47C H 0.2517 0.5925 0.5689 0.131 Uiso 0.33 1 calc PR A 2 H47D H 0.1439 0.5786 0.6565 0.131 Uiso 0.33 1 calc PR A 2 C48A C 0.3557(4) 0.5627(2) 0.6681(3) 0.0933(13) Uani 0.33 1 d PDU A 2 H48C H 0.3270 0.5735 0.7291 0.112 Uiso 0.33 1 calc PR A 2 H48D H 0.3895 0.4951 0.6599 0.112 Uiso 0.33 1 calc PR A 2 C49A C 0.4765(3) 0.6047(2) 0.6275(3) 0.1088(16) Uani 0.33 1 d PDU A 2 H49C H 0.5258 0.5768 0.5722 0.131 Uiso 0.33 1 calc PR A 2 H49D H 0.5491 0.5893 0.6623 0.131 Uiso 0.33 1 calc PR A 2 C50A C 0.4253(3) 0.71030(18) 0.6152(3) 0.0820(11) Uani 0.33 1 d PDU A 2 H50C H 0.4538 0.7368 0.6586 0.098 Uiso 0.33 1 calc PR A 2 H50D H 0.4847 0.7253 0.5606 0.098 Uiso 0.33 1 calc PR A 2 C46B C 0.2427(6) 0.7209(2) 0.6896(3) 0.1142(18) Uani 0.33 1 d PDU A 3 H46C H 0.1828 0.7565 0.7364 0.137 Uiso 0.33 1 calc PR A 3 C47B C 0.3016(10) 0.6160(3) 0.7019(3) 0.198(4) Uani 0.33 1 d PDU A 3 H47E H 0.2271 0.5931 0.7433 0.238 Uiso 0.33 1 calc PR A 3 H47F H 0.3892 0.6025 0.7250 0.238 Uiso 0.33 1 calc PR A 3 C48B C 0.3416(5) 0.5640(2) 0.6199(3) 0.1122(17) Uani 0.33 1 d PDU A 3 H48E H 0.3899 0.4976 0.6284 0.135 Uiso 0.33 1 calc PR A 3 H48F H 0.2535 0.5701 0.5991 0.135 Uiso 0.33 1 calc PR A 3 C49B C 0.4445(5) 0.6096(2) 0.5593(3) 0.1254(19) Uani 0.33 1 d PDU A 3 H49E H 0.5393 0.5898 0.5754 0.150 Uiso 0.33 1 calc PR A 3 H49F H 0.4611 0.5855 0.5030 0.150 Uiso 0.33 1 calc PR A 3 C50B C 0.3988(4) 0.7134(2) 0.5522(3) 0.1058(14) Uani 0.33 1 d PDU A 3 H50E H 0.4833 0.7352 0.5536 0.127 Uiso 0.33 1 calc PR A 3 H50F H 0.3765 0.7315 0.4967 0.127 Uiso 0.33 1 calc PR A 3 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 0.0534(2) 0.0346(2) 0.0575(3) -0.0064(2) -0.0066(2) -0.00765(19) O2 0.1108(4) 0.0418(3) 0.0685(3) 0.0146(2) -0.0361(3) -0.0257(3) O3 0.0716(3) 0.0400(2) 0.0595(3) -0.0105(2) -0.0057(3) -0.0116(2) O4 0.0730(3) 0.0507(3) 0.0642(3) 0.0116(3) -0.0178(3) -0.0020(3) O5 0.04484(19) 0.0738(3) 0.1125(4) -0.0039(3) -0.0280(2) -0.0246(2) O6 0.0665(2) 0.0884(3) 0.0567(3) -0.0219(2) -0.0136(2) -0.0345(2) O7 0.1679(6) 0.1376(6) 0.0412(3) 0.0060(4) -0.0060(4) -0.0708(5) O8 0.0796(3) 0.0812(4) 0.0757(4) -0.0176(3) -0.0330(3) -0.0093(3) N1 0.0446(2) 0.0379(3) 0.0512(3) 0.0032(2) -0.0049(2) -0.0113(2) N2 0.0996(4) 0.0500(3) 0.0403(3) 0.0009(3) -0.0126(3) -0.0292(3) C1 0.0408(3) 0.0333(3) 0.0491(4) -0.0038(3) -0.0066(3) -0.0090(2) C2 0.0409(2) 0.0314(3) 0.0416(3) -0.0009(2) -0.0064(2) -0.0076(2) C3 0.0405(2) 0.0379(3) 0.0453(3) -0.0008(3) -0.0093(2) -0.0103(2) C4 0.0392(2) 0.0350(3) 0.0438(3) -0.0022(3) -0.0039(2) -0.0088(2) C5 0.0491(3) 0.0446(3) 0.0400(3) -0.0041(3) -0.0056(3) -0.0133(3) C6 0.0464(3) 0.0443(3) 0.0475(3) -0.0047(3) -0.0114(3) -0.0152(2) C7 0.0466(3) 0.0443(3) 0.0482(4) 0.0020(3) -0.0106(3) -0.0171(2) C8 0.0528(4) 0.0542(4) 0.0946(7) -0.0019(5) 0.0023(4) -0.0163(3) C9 0.0496(4) 0.0880(7) 0.1078(8) -0.0022(6) 0.0049(5) -0.0157(4) C10 0.0595(3) 0.1125(6) 0.0695(5) 0.0171(5) -0.0110(4) -0.0466(3) C11 0.0772(3) 0.0836(4) 0.0660(5) 0.0135(4) -0.0225(3) -0.0519(3) C12 0.0640(3) 0.0535(4) 0.0571(4) 0.0009(3) -0.0168(3) -0.0290(3) C13 0.0478(3) 0.0392(3) 0.0473(4) 0.0040(3) -0.0089(3) -0.0117(2) C14 0.0575(3) 0.0523(4) 0.0408(4) 0.0023(3) -0.0074(3) -0.0161(3) C15 0.1092(6) 0.0675(5) 0.0515(4) 0.0105(4) -0.0262(4) -0.0241(5) C16 0.1741(9) 0.1037(8) 0.0558(5) 0.0085(5) -0.0478(6) -0.0427(7) C17 0.1805(9) 0.1111(8) 0.0558(5) -0.0123(5) -0.0311(6) -0.0615(7) C18 0.1334(7) 0.0716(5) 0.0575(5) -0.0132(4) -0.0111(5) -0.0405(5) C19 0.0815(4) 0.0547(4) 0.0447(4) -0.0034(3) -0.0073(4) -0.0217(3) C20 0.0422(3) 0.0428(3) 0.0525(4) 0.0026(3) -0.0043(3) -0.0126(2) C21 0.0609(3) 0.1094(6) 0.0777(6) -0.0205(5) 0.0020(4) -0.0450(3) C22 0.0653(4) 0.1048(6) 0.1067(8) -0.0206(6) 0.0046(5) -0.0466(4) C23 0.0490(3) 0.0704(5) 0.1042(8) 0.0046(5) 0.0019(4) -0.0209(3) C24 0.0626(4) 0.0841(6) 0.0726(6) -0.0009(5) 0.0135(4) -0.0208(4) C25 0.0539(3) 0.0667(5) 0.0549(4) -0.0030(4) 0.0005(3) -0.0197(3) C26 0.0386(2) 0.0516(3) 0.0669(5) -0.0069(3) -0.0017(3) -0.0225(2) C27 0.0343(2) 0.0477(3) 0.0416(3) -0.0047(3) -0.0043(2) -0.0182(2) C28 0.0387(2) 0.0477(3) 0.0410(3) -0.0020(3) -0.0048(2) -0.0175(2) C29 0.0490(3) 0.0464(3) 0.0479(4) -0.0031(3) 0.0009(3) -0.0169(3) C30 0.0510(3) 0.0561(4) 0.0922(6) -0.0154(4) 0.0223(4) -0.0200(3) C31 0.0521(3) 0.0576(4) 0.0859(6) -0.0139(4) 0.0251(4) -0.0268(3) C32 0.0546(3) 0.0543(4) 0.0557(4) -0.0121(3) 0.0062(3) -0.0269(3) C33 0.0637(4) 0.0490(4) 0.0884(6) -0.0061(4) -0.0034(4) -0.0204(3) C34 0.0912(6) 0.0557(5) 0.0863(7) -0.0055(5) 0.0022(6) -0.0168(5) C35 0.1445(8) 0.0527(4) 0.0666(6) -0.0100(4) 0.0077(6) -0.0470(4) C36 0.1455(6) 0.0845(5) 0.1025(8) 0.0021(5) -0.0278(6) -0.0770(4) C37 0.0972(4) 0.0757(5) 0.0970(7) 0.0059(5) -0.0253(5) -0.0561(3) C38 0.0428(2) 0.0462(3) 0.0414(3) -0.0049(3) -0.0093(2) -0.0154(2) C39 0.0392(3) 0.0364(3) 0.0409(3) 0.0005(3) -0.0036(2) -0.0077(2) C40 0.0592(4) 0.0413(4) 0.0449(4) -0.0041(3) 0.0000(3) -0.0062(3) C41 0.0610(4) 0.0534(4) 0.0614(5) -0.0006(4) 0.0196(4) -0.0048(4) C42 0.0386(3) 0.0596(5) 0.0932(7) 0.0090(5) 0.0090(4) -0.0075(3) C43 0.0404(3) 0.0617(4) 0.0856(6) 0.0092(4) -0.0179(3) -0.0146(3) C44 0.0386(2) 0.0537(4) 0.0487(4) 0.0045(3) -0.0098(3) -0.0144(2) C45 0.0550(3) 0.0455(4) 0.0568(4) -0.0055(3) -0.0015(3) -0.0137(3) C46 0.0800(15) 0.0561(14) 0.0724(16) 0.0217(12) 0.0438(13) 0.0058(13) C47 0.0873(17) 0.0633(16) 0.156(3) 0.0457(17) 0.0600(18) -0.0026(14) C48 0.0693(15) 0.0375(13) 0.142(3) 0.0203(16) -0.0045(18) -0.0003(12) C49 0.262(6) 0.059(2) 0.113(3) -0.023(2) -0.019(4) 0.015(3) C50 0.343(6) 0.065(2) 0.129(3) -0.0439(19) -0.124(3) 0.063(3) C46A 0.0627(12) 0.0546(15) 0.201(4) 0.012(2) -0.0403(18) -0.0207(11) C47A 0.0822(14) 0.0513(14) 0.210(4) 0.016(2) -0.0568(19) -0.0281(11) C48A 0.111(2) 0.0693(17) 0.101(3) 0.0221(17) -0.0200(19) -0.0389(15) C49A 0.0604(14) 0.0628(18) 0.196(4) 0.010(2) -0.0389(19) -0.0028(14) C50A 0.0497(10) 0.0501(13) 0.147(3) 0.0160(16) -0.0297(13) -0.0165(9) C46B 0.193(4) 0.0471(17) 0.081(2) 0.0004(16) -0.029(3) -0.005(2) C47B 0.404(10) 0.0398(18) 0.073(2) 0.0005(17) -0.023(4) 0.025(4) C48B 0.142(3) 0.0505(15) 0.141(4) -0.012(2) -0.008(3) -0.0399(17) C49B 0.131(3) 0.0547(19) 0.133(3) -0.005(2) 0.046(3) -0.003(2) C50B 0.097(2) 0.0432(14) 0.118(3) 0.0185(16) 0.042(2) 0.0051(15) _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 1.4344(7) . ? O2 C13 1.2151(9) . ? O3 N1 1.2224(9) . ? O4 N1 1.2228(9) . ? O5 C26 1.4308(11) . ? O6 C38 1.2254(10) . ? O7 N2 1.2224(10) . ? O8 N2 1.2007(10) . ? N1 C4 1.5571(8) . ? N2 C29 1.5646(12) . ? C1 C6 1.5259(10) . ? C1 C7 1.5359(9) . ? C1 C2 1.5483(11) . ? C2 C13 1.5231(10) . ? C2 C3 1.5462(9) . ? C3 C4 1.5253(10) . ? C4 C5 1.5265(11) . ? C4 C20 1.5343(9) . ? C5 C6 1.5300(9) . ? C7 C8 1.3849(10) . ? C7 C12 1.3875(11) . ? C8 C9 1.3911(13) . ? C9 C10 1.3734(17) . ? C10 C11 1.3684(12) . ? C11 C12 1.3869(11) . ? C13 C14 1.4918(12) . ? C14 C19 1.3897(12) . ? C14 C15 1.3916(12) . ? C15 C16 1.3733(18) . ? C16 C17 1.3776(19) . ? C17 C18 1.3748(17) . ? C18 C19 1.3823(15) . ? C20 C25 1.3287(12) . ? C20 C21 1.4915(14) . ? C21 C22 1.5225(14) . ? C22 C23 1.4955(15) . ? C23 C24 1.4956(17) . ? C24 C25 1.5129(12) . ? C26 C32 1.5265(11) . ? C26 C31 1.5354(12) . ? C26 C27 1.5477(10) . ? C27 C38 1.5184(9) . ? C27 C28 1.5460(9) . ? C28 C29 1.5296(10) . ? C29 C30 1.5262(12) . ? C29 C45 1.5304(11) . ? C30 C31 1.5257(12) . ? C32 C33 1.3798(12) . ? C32 C37 1.3905(14) . ? C33 C34 1.3861(14) . ? C34 C35 1.3780(19) . ? C35 C36 1.3726(17) . ? C36 C37 1.3653(14) . ? C38 C39 1.4875(9) . ? C39 C44 1.3907(11) . ? C39 C40 1.3952(10) . ? C40 C41 1.3753(12) . ? C41 C42 1.3678(16) . ? C42 C43 1.3854(14) . ? C43 C44 1.3918(10) . ? C45 C46 1.272(3) . ? C45 C46B 1.288(4) . ? C45 C46A 1.396(3) . ? C45 C50B 1.451(3) . ? C45 C50A 1.452(2) . ? C45 C50 1.479(4) . ? C46 C47 1.481(4) . ? C47 C48 1.496(4) . ? C48 C49 1.510(6) . ? C49 C50 1.498(5) . ? C46A C47A 1.504(4) . ? C47A C48A 1.509(5) . ? C48A C49A 1.468(5) . ? C49A C50A 1.506(4) . ? C46B C47B 1.503(5) . ? C47B C48B 1.507(6) . ? C48B C49B 1.480(6) . ? C49B C50B 1.473(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 N1 O4 123.06(6) . . ? O3 N1 C4 119.05(6) . . ? O4 N1 C4 117.82(6) . . ? O8 N2 O7 123.15(9) . . ? O8 N2 C29 119.68(6) . . ? O7 N2 C29 117.04(8) . . ? O1 C1 C6 105.94(5) . . ? O1 C1 C7 110.63(6) . . ? C6 C1 C7 109.47(6) . . ? O1 C1 C2 109.75(5) . . ? C6 C1 C2 108.24(6) . . ? C7 C1 C2 112.56(6) . . ? C13 C2 C3 107.87(6) . . ? C13 C2 C1 112.49(6) . . ? C3 C2 C1 110.72(5) . . ? C4 C3 C2 114.60(6) . . ? C3 C4 C5 110.59(6) . . ? C3 C4 C20 111.50(6) . . ? C5 C4 C20 114.45(6) . . ? C3 C4 N1 108.50(5) . . ? C5 C4 N1 107.56(5) . . ? C20 C4 N1 103.79(5) . . ? C4 C5 C6 113.19(6) . . ? C1 C6 C5 112.62(6) . . ? C8 C7 C12 118.12(7) . . ? C8 C7 C1 121.11(7) . . ? C12 C7 C1 120.67(6) . . ? C7 C8 C9 120.53(9) . . ? C10 C9 C8 120.65(9) . . ? C11 C10 C9 119.25(8) . . ? C10 C11 C12 120.60(9) . . ? C11 C12 C7 120.84(7) . . ? O2 C13 C14 118.95(7) . . ? O2 C13 C2 120.45(7) . . ? C14 C13 C2 120.60(6) . . ? C19 C14 C15 119.29(9) . . ? C19 C14 C13 123.06(7) . . ? C15 C14 C13 117.62(8) . . ? C16 C15 C14 120.41(10) . . ? C15 C16 C17 119.69(11) . . ? C18 C17 C16 120.81(12) . . ? C17 C18 C19 119.77(11) . . ? C18 C19 C14 120.01(8) . . ? C25 C20 C21 121.32(7) . . ? C25 C20 C4 121.72(8) . . ? C21 C20 C4 116.94(7) . . ? C20 C21 C22 113.82(9) . . ? C23 C22 C21 110.69(10) . . ? C24 C23 C22 110.65(8) . . ? C23 C24 C25 112.60(9) . . ? C20 C25 C24 123.27(9) . . ? O5 C26 C32 110.34(7) . . ? O5 C26 C31 106.49(6) . . ? C32 C26 C31 108.48(7) . . ? O5 C26 C27 109.42(6) . . ? C32 C26 C27 114.05(5) . . ? C31 C26 C27 107.74(7) . . ? C38 C27 C28 108.08(5) . . ? C38 C27 C26 112.39(6) . . ? C28 C27 C26 111.14(5) . . ? C29 C28 C27 114.09(6) . . ? C30 C29 C28 110.14(7) . . ? C30 C29 C45 113.22(6) . . ? C28 C29 C45 113.32(6) . . ? C30 C29 N2 108.07(7) . . ? C28 C29 N2 107.27(5) . . ? C45 C29 N2 104.35(7) . . ? C31 C30 C29 112.91(6) . . ? C30 C31 C26 112.48(8) . . ? C33 C32 C37 117.42(8) . . ? C33 C32 C26 123.10(8) . . ? C37 C32 C26 119.37(7) . . ? C32 C33 C34 121.49(10) . . ? C35 C34 C33 119.74(11) . . ? C36 C35 C34 119.25(10) . . ? C37 C36 C35 120.77(12) . . ? C36 C37 C32 121.32(10) . . ? O6 C38 C39 119.34(6) . . ? O6 C38 C27 120.57(6) . . ? C39 C38 C27 119.99(6) . . ? C44 C39 C40 119.18(7) . . ? C44 C39 C38 122.41(6) . . ? C40 C39 C38 118.40(7) . . ? C41 C40 C39 120.45(9) . . ? C42 C41 C40 120.22(8) . . ? C41 C42 C43 120.54(8) . . ? C42 C43 C44 119.71(9) . . ? C39 C44 C43 119.87(7) . . ? C46 C45 C46B 24.4(3) . . ? C46 C45 C46A 31.3(3) . . ? C46B C45 C46A 55.4(3) . . ? C46 C45 C50B 120.11(18) . . ? C46B C45 C50B 117.5(2) . . ? C46A C45 C50B 109.4(2) . . ? C46 C45 C50A 101.26(19) . . ? C46B C45 C50A 84.3(3) . . ? C46A C45 C50A 115.64(17) . . ? C50B C45 C50A 44.7(2) . . ? C46 C45 C50 107.5(3) . . ? C46B C45 C50 121.6(3) . . ? C46A C45 C50 82.6(3) . . ? C50B C45 C50 37.4(3) . . ? C50A C45 C50 79.6(3) . . ? C46 C45 C29 123.44(13) . . ? C46B C45 C29 122.43(17) . . ? C46A C45 C29 121.04(12) . . ? C50B C45 C29 116.16(14) . . ? C50A C45 C29 122.87(13) . . ? C50 C45 C29 113.31(16) . . ? C45 C46 C47 123.9(2) . . ? C46 C47 C48 113.4(3) . . ? C47 C48 C49 97.1(3) . . ? C50 C49 C48 117.8(4) . . ? C45 C50 C49 113.4(3) . . ? C45 C46A C47A 118.4(2) . . ? C46A C47A C48A 111.6(4) . . ? C49A C48A C47A 109.7(3) . . ? C48A C49A C50A 113.8(2) . . ? C45 C50A C49A 123.8(2) . . ? C45 C46B C47B 122.4(3) . . ? C46B C47B C48B 112.6(4) . . ? C49B C48B C47B 104.8(4) . . ? C50B C49B C48B 117.5(3) . . ? C45 C50B C49B 117.2(3) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.243 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 # Attachment '8b-ms94ccd-728934.cif' data_ms94ccd _database_code_depnum_ccdc_archive 'CCDC 728934' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O2' _chemical_formula_weight 241.28 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6259(5) _cell_length_b 12.9816(10) _cell_length_c 14.3547(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.478(1) _cell_angle_gamma 90.00 _cell_volume 1214.13(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5949 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7958 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2705 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.2069P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2705 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4339(2) 0.69850(10) 0.32853(8) 0.0695(4) Uani 1 1 d . . . O2 O 0.62167(17) 0.85409(9) 0.47488(9) 0.0650(3) Uani 1 1 d . . . N1 N 0.35405(16) 0.73982(8) 0.47422(7) 0.0392(3) Uani 1 1 d . . . C1 C 0.19482(17) 0.71723(9) 0.53112(8) 0.0345(3) Uani 1 1 d . . . C2 C 0.0130(2) 0.68115(11) 0.45413(9) 0.0447(3) Uani 1 1 d . . . H2A H -0.0650 0.6274 0.4784 0.054 Uiso 1 1 calc R . . H2B H -0.0780 0.7381 0.4322 0.054 Uiso 1 1 calc R . . C3 C 0.1155(3) 0.64027(12) 0.37440(10) 0.0554(4) Uani 1 1 d . . . H3A H 0.1349 0.5663 0.3801 0.066 Uiso 1 1 calc R . . H3B H 0.0317 0.6552 0.3132 0.066 Uiso 1 1 calc R . . C4 C 0.3192(2) 0.69418(11) 0.38449(9) 0.0474(3) Uani 1 1 d . . . C5 C 0.4785(2) 0.82268(11) 0.50794(10) 0.0438(3) Uani 1 1 d . . . C6 C 0.3962(2) 0.86598(11) 0.59116(10) 0.0463(3) Uani 1 1 d . . . H6A H 0.3930 0.9407 0.5890 0.056 Uiso 1 1 calc R . . H6B H 0.4798 0.8443 0.6505 0.056 Uiso 1 1 calc R . . C7 C 0.17922(19) 0.82191(10) 0.58048(9) 0.0394(3) Uani 1 1 d . . . H7A H 0.0803 0.8666 0.5419 0.047 Uiso 1 1 calc R . . H7B H 0.1397 0.8127 0.6418 0.047 Uiso 1 1 calc R . . C8 C 0.26374(18) 0.62973(9) 0.60135(8) 0.0352(3) Uani 1 1 d . . . C9 C 0.4198(2) 0.56923(12) 0.59092(10) 0.0505(3) Uani 1 1 d . . . H9A H 0.4566 0.5144 0.6322 0.061 Uiso 1 1 calc R . . H9B H 0.4922 0.5817 0.5423 0.061 Uiso 1 1 calc R . . C10 C 0.14528(18) 0.61102(9) 0.67910(8) 0.0361(3) Uani 1 1 d . . . C11 C -0.0532(2) 0.64911(11) 0.67665(10) 0.0437(3) Uani 1 1 d . . . H11 H -0.1168 0.6869 0.6245 0.052 Uiso 1 1 calc R . . C12 C -0.1564(2) 0.63114(12) 0.75122(11) 0.0505(4) Uani 1 1 d . . . H12 H -0.2874 0.6579 0.7490 0.061 Uiso 1 1 calc R . . C13 C -0.0656(2) 0.57395(12) 0.82829(10) 0.0518(4) Uani 1 1 d . . . H13 H -0.1361 0.5610 0.8775 0.062 Uiso 1 1 calc R . . C14 C 0.1302(2) 0.53593(12) 0.83232(10) 0.0531(4) Uani 1 1 d . . . H14 H 0.1919 0.4972 0.8843 0.064 Uiso 1 1 calc R . . C15 C 0.2345(2) 0.55536(11) 0.75911(9) 0.0462(3) Uani 1 1 d . . . H15 H 0.3677 0.5307 0.7633 0.055 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 0.0943(9) 0.0734(8) 0.0498(6) -0.0046(5) 0.0368(6) 0.0049(7) O2 0.0547(6) 0.0668(8) 0.0820(8) -0.0050(6) 0.0353(6) -0.0122(5) N1 0.0462(6) 0.0383(5) 0.0361(5) -0.0020(4) 0.0156(4) -0.0006(4) C1 0.0367(5) 0.0345(6) 0.0335(6) -0.0017(4) 0.0093(4) 0.0003(4) C2 0.0446(7) 0.0451(7) 0.0414(7) 0.0002(5) 0.0001(5) -0.0022(5) C3 0.0715(9) 0.0522(8) 0.0395(7) -0.0099(6) 0.0021(6) -0.0026(7) C4 0.0681(9) 0.0408(7) 0.0353(6) -0.0010(5) 0.0150(6) 0.0078(6) C5 0.0420(6) 0.0421(7) 0.0495(7) 0.0004(5) 0.0141(5) -0.0002(5) C6 0.0498(7) 0.0422(7) 0.0488(7) -0.0100(6) 0.0136(6) -0.0065(5) C7 0.0446(6) 0.0342(6) 0.0418(6) -0.0034(5) 0.0143(5) 0.0013(5) C8 0.0378(6) 0.0343(6) 0.0335(6) -0.0022(4) 0.0064(4) -0.0008(4) C9 0.0577(8) 0.0510(8) 0.0453(7) 0.0047(6) 0.0159(6) 0.0163(6) C10 0.0388(6) 0.0334(6) 0.0368(6) -0.0017(4) 0.0085(4) -0.0044(4) C11 0.0413(6) 0.0442(7) 0.0466(7) 0.0007(5) 0.0102(5) -0.0016(5) C12 0.0437(7) 0.0507(8) 0.0613(9) -0.0074(6) 0.0204(6) -0.0056(6) C13 0.0611(8) 0.0517(8) 0.0479(8) -0.0042(6) 0.0238(6) -0.0156(6) C14 0.0625(8) 0.0556(9) 0.0421(7) 0.0083(6) 0.0123(6) -0.0069(7) C15 0.0444(7) 0.0506(8) 0.0438(7) 0.0063(6) 0.0085(5) -0.0004(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 C4 1.2035(18) . ? O2 C5 1.2065(16) . ? N1 C5 1.3877(17) . ? N1 C4 1.3983(17) . ? N1 C1 1.4763(14) . ? C1 C8 1.5322(17) . ? C1 C7 1.5446(16) . ? C1 C2 1.5515(17) . ? C2 C3 1.528(2) . ? C3 C4 1.504(2) . ? C5 C6 1.5090(18) . ? C6 C7 1.5289(18) . ? C8 C9 1.3283(18) . ? C8 C10 1.4965(15) . ? C10 C15 1.3943(18) . ? C10 C11 1.3993(18) . ? C11 C12 1.3908(18) . ? C12 C13 1.377(2) . ? C13 C14 1.379(2) . ? C14 C15 1.3823(18) . ? 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 C5 N1 C4 129.64(11) . . ? C5 N1 C1 113.58(10) . . ? C4 N1 C1 114.23(11) . . ? N1 C1 C8 110.72(9) . . ? N1 C1 C7 101.14(9) . . ? C8 C1 C7 112.78(10) . . ? N1 C1 C2 101.90(9) . . ? C8 C1 C2 110.17(10) . . ? C7 C1 C2 118.96(10) . . ? C3 C2 C1 104.19(11) . . ? C4 C3 C2 106.22(11) . . ? O1 C4 N1 125.20(15) . . ? O1 C4 C3 128.47(14) . . ? N1 C4 C3 106.33(11) . . ? O2 C5 N1 125.78(13) . . ? O2 C5 C6 127.49(14) . . ? N1 C5 C6 106.71(10) . . ? C5 C6 C7 104.46(10) . . ? C6 C7 C1 103.60(9) . . ? C9 C8 C10 120.84(12) . . ? C9 C8 C1 120.61(11) . . ? C10 C8 C1 118.50(10) . . ? C15 C10 C11 117.37(11) . . ? C15 C10 C8 119.80(11) . . ? C11 C10 C8 122.81(11) . . ? C12 C11 C10 120.85(13) . . ? C13 C12 C11 120.32(13) . . ? C12 C13 C14 119.79(12) . . ? C13 C14 C15 119.98(13) . . ? C14 C15 C10 121.65(13) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.264 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.048