# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email hiroyuki.nakamura@gakushuin.ac.jp _publ_contact_author_name 'Hiroyuki Nakamura' _publ_author_name 'Hiroyuki Nakamura' data_compound9 _database_code_depnum_ccdc_archive 'CCDC 829854' #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O3' _chemical_formula_weight 293.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Fdd2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 18.004(3) _cell_length_b 39.249(6) _cell_length_c 8.1408(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5752.6(14) _cell_formula_units_Z 16 _cell_measurement_temperature 123 _cell_measurement_reflns_used 2821 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.13 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9862 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 7939 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3191 _reflns_number_gt 2822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(9) _refine_ls_number_reflns 3191 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0546 _refine_ls_goodness_of_fit_ref 1.675 _refine_ls_restrained_S_all 1.675 _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 0.37388(9) -0.04114(4) 0.54413(19) 0.0177(3) Uani 1 1 d . . . C2 C 0.34359(8) -0.06928(4) 0.6259(2) 0.0219(4) Uani 1 1 d . . . H2 H 0.3001 -0.0668 0.6909 0.026 Uiso 1 1 calc R . . C3 C 0.37757(9) -0.10077(4) 0.6113(2) 0.0242(4) Uani 1 1 d . . . H3 H 0.3571 -0.1200 0.6658 0.029 Uiso 1 1 calc R . . C4 C 0.44151(9) -0.10440(4) 0.5172(2) 0.0270(4) Uani 1 1 d . . . H4 H 0.4645 -0.1261 0.5079 0.032 Uiso 1 1 calc R . . C5 C 0.47172(9) -0.07660(4) 0.4372(2) 0.0252(4) Uani 1 1 d . . . H5 H 0.5157 -0.0791 0.3738 0.030 Uiso 1 1 calc R . . C6 C 0.43756(8) -0.04504(4) 0.4500(2) 0.0218(4) Uani 1 1 d . . . H6 H 0.4579 -0.0260 0.3939 0.026 Uiso 1 1 calc R . . C7 C 0.33729(8) -0.00789(4) 0.55884(19) 0.0183(4) Uani 1 1 d . . . C8 C 0.32050(8) 0.04559(4) 0.47783(19) 0.0194(4) Uani 1 1 d . . . C9 C 0.26866(8) 0.03697(4) 0.6193(2) 0.0185(4) Uani 1 1 d . . . C10 C 0.28181(8) 0.05994(4) 0.7722(2) 0.0196(4) Uani 1 1 d . . . H10 H 0.2436 0.0532 0.8552 0.024 Uiso 1 1 calc R . . C11 C 0.26703(8) 0.09766(4) 0.7303(2) 0.0245(4) Uani 1 1 d . . . H11A H 0.2649 0.1111 0.8332 0.029 Uiso 1 1 calc R . . H11B H 0.3086 0.1066 0.6634 0.029 Uiso 1 1 calc R . . C12 C 0.19595(9) 0.10219(4) 0.6380(2) 0.0270(4) Uani 1 1 d . . . H12 H 0.1752 0.1244 0.6310 0.032 Uiso 1 1 calc R . . C13 C 0.16052(9) 0.07678(4) 0.5657(2) 0.0256(4) Uani 1 1 d . . . H13 H 0.1154 0.0818 0.5103 0.031 Uiso 1 1 calc R . . C14 C 0.18699(8) 0.04040(4) 0.5655(2) 0.0223(4) Uani 1 1 d . . . H14A H 0.1813 0.0309 0.4536 0.027 Uiso 1 1 calc R . . H14B H 0.1554 0.0268 0.6406 0.027 Uiso 1 1 calc R . . C15 C 0.35556(9) 0.05442(4) 0.8512(2) 0.0206(4) Uani 1 1 d . . . C16 C 0.37731(9) 0.04830(4) 1.0053(2) 0.0279(4) Uani 1 1 d . . . H16 H 0.3460 0.0458 1.0985 0.034 Uiso 1 1 calc R . . C17 C 0.45659(9) 0.04617(4) 1.0036(2) 0.0312(4) Uani 1 1 d . . . H17 H 0.4882 0.0420 1.0948 0.037 Uiso 1 1 calc R . . C18 C 0.47711(9) 0.05122(5) 0.8479(2) 0.0317(4) Uani 1 1 d . . . H18 H 0.5271 0.0511 0.8103 0.038 Uiso 1 1 calc R . . N1 N 0.28637(7) 0.00112(3) 0.65796(16) 0.0186(3) Uani 1 1 d . . . O1 O 0.32816(6) 0.07060(3) 0.39672(13) 0.0243(3) Uani 1 1 d . . . O2 O 0.36225(5) 0.01653(3) 0.44627(13) 0.0194(3) Uani 1 1 d . . . O3 O 0.41646(6) 0.05656(3) 0.74972(14) 0.0285(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0171(8) 0.0175(8) 0.0184(9) -0.0004(6) -0.0044(7) 0.0005(7) C2 0.0176(9) 0.0248(9) 0.0231(9) 0.0021(7) -0.0022(7) -0.0018(7) C3 0.0247(9) 0.0169(9) 0.0310(11) 0.0055(7) -0.0015(9) -0.0030(7) C4 0.0271(10) 0.0176(9) 0.0363(11) 0.0002(8) -0.0001(9) 0.0058(7) C5 0.0206(9) 0.0254(10) 0.0295(10) -0.0004(8) 0.0036(8) 0.0022(7) C6 0.0234(9) 0.0192(9) 0.0228(10) 0.0031(7) -0.0032(8) -0.0021(7) C7 0.0193(9) 0.0181(9) 0.0174(9) 0.0025(7) -0.0037(8) -0.0045(7) C8 0.0188(9) 0.0207(9) 0.0187(9) -0.0025(7) -0.0025(8) -0.0014(7) C9 0.0215(9) 0.0147(8) 0.0192(9) 0.0006(7) 0.0014(7) 0.0004(7) C10 0.0191(8) 0.0218(9) 0.0178(9) -0.0012(7) 0.0015(8) -0.0006(7) C11 0.0259(10) 0.0220(9) 0.0256(11) -0.0031(7) 0.0016(9) 0.0009(7) C12 0.0260(10) 0.0218(9) 0.0333(11) 0.0016(8) 0.0019(9) 0.0044(7) C13 0.0208(9) 0.0260(10) 0.0299(10) 0.0022(8) -0.0012(8) 0.0046(7) C14 0.0206(9) 0.0237(9) 0.0227(10) -0.0022(7) -0.0015(8) -0.0018(7) C15 0.0204(9) 0.0201(9) 0.0212(10) -0.0015(7) 0.0055(8) -0.0026(7) C16 0.0291(10) 0.0339(11) 0.0209(10) 0.0011(8) 0.0040(8) -0.0009(8) C17 0.0316(11) 0.0370(11) 0.0250(11) 0.0005(9) -0.0078(9) 0.0016(8) C18 0.0182(10) 0.0459(12) 0.0310(11) -0.0026(9) -0.0032(9) 0.0002(8) N1 0.0198(7) 0.0161(7) 0.0200(8) 0.0011(6) -0.0013(6) -0.0012(6) O1 0.0313(7) 0.0183(6) 0.0233(7) 0.0044(5) 0.0030(6) 0.0002(5) O2 0.0239(6) 0.0152(6) 0.0193(6) 0.0020(4) 0.0029(5) 0.0021(5) O3 0.0212(6) 0.0440(8) 0.0204(7) -0.0014(6) 0.0008(5) -0.0022(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 C1 C6 1.387(2) . ? C1 C2 1.400(2) . ? C1 C7 1.467(2) . ? C2 C3 1.384(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.2715(18) . ? C7 O2 1.4003(17) . ? C8 O1 1.1912(17) . ? C8 O2 1.3897(17) . ? C8 C9 1.520(2) . ? C9 N1 1.4766(18) . ? C9 C14 1.5401(19) . ? C9 C10 1.555(2) . ? C10 C15 1.491(2) . ? C10 C11 1.543(2) . ? C10 H10 1.0000 . ? C11 C12 1.495(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.322(2) . ? C12 H12 0.9500 . ? C13 C14 1.505(2) . ? C13 H13 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.336(2) . ? C15 O3 1.3755(17) . ? C16 C17 1.430(2) . ? C16 H16 0.9500 . ? C17 C18 1.335(2) . ? C17 H17 0.9500 . ? C18 O3 1.3696(19) . ? C18 H18 0.9500 . ? 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 C6 C1 C2 119.84(15) . . ? C6 C1 C7 120.94(14) . . ? C2 C1 C7 119.22(15) . . ? C3 C2 C1 119.43(16) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.33(15) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.30(15) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.70(16) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 120.40(15) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N1 C7 O2 117.14(13) . . ? N1 C7 C1 128.55(14) . . ? O2 C7 C1 114.31(13) . . ? O1 C8 O2 120.75(14) . . ? O1 C8 C9 132.40(15) . . ? O2 C8 C9 106.82(13) . . ? N1 C9 C8 103.94(12) . . ? N1 C9 C14 110.49(12) . . ? C8 C9 C14 110.57(13) . . ? N1 C9 C10 110.42(12) . . ? C8 C9 C10 112.57(12) . . ? C14 C9 C10 108.79(12) . . ? C15 C10 C11 112.84(12) . . ? C15 C10 C9 113.37(13) . . ? C11 C10 C9 110.69(13) . . ? C15 C10 H10 106.5 . . ? C11 C10 H10 106.5 . . ? C9 C10 H10 106.5 . . ? C12 C11 C10 111.89(13) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 123.18(15) . . ? C13 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? C12 C13 C14 124.28(16) . . ? C12 C13 H13 117.9 . . ? C14 C13 H13 117.9 . . ? C13 C14 C9 112.64(13) . . ? C13 C14 H14A 109.1 . . ? C9 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C9 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C16 C15 O3 109.96(14) . . ? C16 C15 C10 133.80(15) . . ? O3 C15 C10 116.22(14) . . ? C15 C16 C17 107.10(16) . . ? C15 C16 H16 126.4 . . ? C17 C16 H16 126.4 . . ? C18 C17 C16 106.07(16) . . ? C18 C17 H17 127.0 . . ? C16 C17 H17 127.0 . . ? C17 C18 O3 110.87(15) . . ? C17 C18 H18 124.6 . . ? O3 C18 H18 124.6 . . ? C7 N1 C9 106.59(13) . . ? C8 O2 C7 105.51(11) . . ? C18 O3 C15 105.99(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.180 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.040 #===END data_compound12 _database_code_depnum_ccdc_archive 'CCDC 829855' #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N O3' _chemical_formula_weight 347.40 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 'P2(1)/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 10.6098(13) _cell_length_b 18.036(2) _cell_length_c 9.5122(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.7510(10) _cell_angle_gamma 90.00 _cell_volume 1799.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 7299 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 19451 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4109 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0433P)^2^+0.6240P] 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 4109 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _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 0.09116(11) 0.21225(7) 0.67683(13) 0.0191(2) Uani 1 1 d . . . C2 C 0.04074(12) 0.14783(7) 0.72662(14) 0.0242(3) Uani 1 1 d . . . H2 H 0.0864 0.1223 0.8058 0.029 Uiso 1 1 calc R . . C3 C -0.07578(13) 0.12077(8) 0.66112(15) 0.0300(3) Uani 1 1 d . . . H3 H -0.1095 0.0767 0.6955 0.036 Uiso 1 1 calc R . . C4 C -0.14348(12) 0.15762(8) 0.54564(16) 0.0307(3) Uani 1 1 d . . . H4 H -0.2235 0.1390 0.5013 0.037 Uiso 1 1 calc R . . C5 C -0.09382(13) 0.22149(8) 0.49555(16) 0.0320(3) Uani 1 1 d . . . H5 H -0.1398 0.2468 0.4164 0.038 Uiso 1 1 calc R . . C6 C 0.02317(12) 0.24884(8) 0.56045(14) 0.0254(3) Uani 1 1 d . . . H6 H 0.0569 0.2927 0.5252 0.030 Uiso 1 1 calc R . . C8 C 0.21521(11) 0.24098(7) 0.75439(12) 0.0176(2) Uani 1 1 d . . . C9 C 0.39439(11) 0.32713(6) 0.75321(12) 0.0172(2) Uani 1 1 d . . . C10 C 0.44630(11) 0.37269(7) 0.63432(12) 0.0186(2) Uani 1 1 d . . . H10 H 0.4538 0.3375 0.5547 0.022 Uiso 1 1 calc R . . C11 C 0.57869(12) 0.40444(7) 0.68265(12) 0.0203(3) Uani 1 1 d . . . C12 C 0.68497(12) 0.36722(7) 0.64816(14) 0.0245(3) Uani 1 1 d . . . H12 H 0.6740 0.3214 0.5985 0.029 Uiso 1 1 calc R . . C13 C 0.80676(13) 0.39630(8) 0.68552(15) 0.0311(3) Uani 1 1 d . . . H13 H 0.8782 0.3702 0.6613 0.037 Uiso 1 1 calc R . . C14 C 0.82483(14) 0.46315(8) 0.75795(15) 0.0322(3) Uani 1 1 d . . . H14 H 0.9082 0.4829 0.7831 0.039 Uiso 1 1 calc R . . C15 C 0.72058(14) 0.50067(8) 0.79317(14) 0.0294(3) Uani 1 1 d . . . H15 H 0.7323 0.5465 0.8427 0.035 Uiso 1 1 calc R . . C16 C 0.59837(13) 0.47178(7) 0.75663(13) 0.0245(3) Uani 1 1 d . . . H16 H 0.5275 0.4979 0.7820 0.029 Uiso 1 1 calc R . . C17 C 0.34748(12) 0.43226(7) 0.57484(13) 0.0228(3) Uani 1 1 d . . . H17A H 0.3917 0.4716 0.5286 0.027 Uiso 1 1 calc R . . H17B H 0.2839 0.4093 0.5007 0.027 Uiso 1 1 calc R . . C18 C 0.27867(13) 0.46728(7) 0.68439(14) 0.0280(3) Uani 1 1 d . . . H18 H 0.2258 0.5089 0.6567 0.034 Uiso 1 1 calc R . . C19 C 0.28708(13) 0.44367(7) 0.81738(14) 0.0274(3) Uani 1 1 d . . . H19 H 0.2405 0.4693 0.8799 0.033 Uiso 1 1 calc R . . C20 C 0.36674(12) 0.37825(7) 0.87405(13) 0.0211(3) Uani 1 1 d . . . H20A H 0.3213 0.3499 0.9401 0.025 Uiso 1 1 calc R . . H20B H 0.4483 0.3960 0.9281 0.025 Uiso 1 1 calc R . . C21 C 0.49436(11) 0.26866(6) 0.80943(12) 0.0174(2) Uani 1 1 d . . . C22 C 0.58856(13) 0.15664(7) 0.75288(15) 0.0274(3) Uani 1 1 d . . . H22A H 0.6722 0.1807 0.7726 0.041 Uiso 1 1 calc R . . H22B H 0.5873 0.1223 0.6728 0.041 Uiso 1 1 calc R . . H22C H 0.5725 0.1291 0.8372 0.041 Uiso 1 1 calc R . . N1 N 0.27667(9) 0.29131(6) 0.68522(11) 0.0175(2) Uani 1 1 d . . . O1 O 0.25720(8) 0.22016(5) 0.87644(9) 0.0220(2) Uani 1 1 d . . . O2 O 0.57013(8) 0.27485(5) 0.91628(9) 0.0230(2) Uani 1 1 d . . . O3 O 0.49121(8) 0.21207(5) 0.71777(9) 0.0214(2) Uani 1 1 d . . . H1N H 0.2564(14) 0.2934(8) 0.5927(17) 0.024(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0160(6) 0.0224(6) 0.0192(6) -0.0021(5) 0.0037(4) 0.0021(4) C2 0.0233(6) 0.0241(6) 0.0251(7) 0.0009(5) 0.0032(5) -0.0002(5) C3 0.0261(7) 0.0277(7) 0.0368(8) -0.0015(6) 0.0065(6) -0.0065(5) C4 0.0173(6) 0.0386(8) 0.0354(8) -0.0084(6) 0.0016(5) -0.0041(5) C5 0.0210(6) 0.0407(8) 0.0319(8) 0.0040(6) -0.0040(5) 0.0024(6) C6 0.0196(6) 0.0285(7) 0.0272(7) 0.0046(5) 0.0012(5) 0.0001(5) C8 0.0171(5) 0.0186(6) 0.0172(6) -0.0009(4) 0.0034(4) 0.0024(4) C9 0.0192(6) 0.0177(6) 0.0142(6) 0.0004(4) 0.0015(4) -0.0012(4) C10 0.0229(6) 0.0175(6) 0.0153(6) 0.0006(4) 0.0026(4) -0.0019(4) C11 0.0257(6) 0.0196(6) 0.0154(6) 0.0030(5) 0.0020(5) -0.0047(5) C12 0.0279(7) 0.0221(6) 0.0234(7) -0.0006(5) 0.0037(5) -0.0039(5) C13 0.0249(7) 0.0336(8) 0.0347(8) 0.0009(6) 0.0040(6) -0.0027(6) C14 0.0287(7) 0.0330(7) 0.0326(8) 0.0030(6) -0.0026(6) -0.0117(6) C15 0.0404(8) 0.0231(7) 0.0227(7) 0.0002(5) -0.0014(6) -0.0101(6) C16 0.0319(7) 0.0198(6) 0.0217(6) 0.0004(5) 0.0037(5) -0.0034(5) C17 0.0276(6) 0.0206(6) 0.0194(6) 0.0040(5) 0.0010(5) 0.0000(5) C18 0.0318(7) 0.0231(7) 0.0282(7) 0.0012(5) 0.0014(5) 0.0083(5) C19 0.0328(7) 0.0251(7) 0.0248(7) -0.0035(5) 0.0057(5) 0.0077(5) C20 0.0267(6) 0.0210(6) 0.0157(6) -0.0008(5) 0.0035(5) 0.0012(5) C21 0.0182(6) 0.0180(6) 0.0165(6) 0.0010(4) 0.0042(4) -0.0035(4) C22 0.0273(7) 0.0235(7) 0.0309(7) -0.0021(5) 0.0028(5) 0.0068(5) N1 0.0179(5) 0.0213(5) 0.0128(5) 0.0010(4) 0.0002(4) -0.0011(4) O1 0.0227(4) 0.0257(5) 0.0172(4) 0.0036(3) 0.0017(3) -0.0012(3) O2 0.0230(5) 0.0238(5) 0.0204(5) 0.0006(3) -0.0024(3) -0.0004(3) O3 0.0219(4) 0.0196(4) 0.0220(5) -0.0023(3) 0.0011(3) 0.0023(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 C2 1.3919(18) . ? C1 C6 1.3924(17) . ? C1 C8 1.4998(16) . ? C2 C3 1.3858(18) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 C6 1.3899(19) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 O1 1.2369(14) . ? C8 N1 1.3464(15) . ? C9 N1 1.4662(15) . ? C9 C21 1.5333(16) . ? C9 C20 1.5362(16) . ? C9 C10 1.5643(16) . ? C10 C11 1.5218(16) . ? C10 C17 1.5470(17) . ? C10 H10 1.0000 . ? C11 C12 1.3937(18) . ? C11 C16 1.4033(17) . ? C12 C13 1.3897(18) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.381(2) . ? C14 H14 0.9500 . ? C15 C16 1.3915(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.4997(18) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.3248(19) . ? C18 H18 0.9500 . ? C19 C20 1.5029(17) . ? C19 H19 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O2 1.2013(14) . ? C21 O3 1.3394(14) . ? C22 O3 1.4398(15) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1N 0.874(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.12(11) . . ? C2 C1 C8 118.36(11) . . ? C6 C1 C8 122.49(11) . . ? C3 C2 C1 120.25(12) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.42(13) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.60(12) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.30(13) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.30(12) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O1 C8 N1 122.09(11) . . ? O1 C8 C1 121.38(11) . . ? N1 C8 C1 116.52(10) . . ? N1 C9 C21 110.39(9) . . ? N1 C9 C20 110.34(10) . . ? C21 C9 C20 110.64(9) . . ? N1 C9 C10 106.41(9) . . ? C21 C9 C10 108.21(9) . . ? C20 C9 C10 110.73(9) . . ? C11 C10 C17 113.09(10) . . ? C11 C10 C9 112.93(9) . . ? C17 C10 C9 109.62(10) . . ? C11 C10 H10 106.9 . . ? C17 C10 H10 106.9 . . ? C9 C10 H10 106.9 . . ? C12 C11 C16 118.10(11) . . ? C12 C11 C10 119.36(11) . . ? C16 C11 C10 122.49(11) . . ? C13 C12 C11 120.81(12) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.51(13) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.42(13) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.41(13) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.75(13) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C18 C17 C10 114.38(10) . . ? C18 C17 H17A 108.7 . . ? C10 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C10 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 123.98(12) . . ? C19 C18 H18 118.0 . . ? C17 C18 H18 118.0 . . ? C18 C19 C20 123.19(12) . . ? C18 C19 H19 118.4 . . ? C20 C19 H19 118.4 . . ? C19 C20 C9 111.33(10) . . ? C19 C20 H20A 109.4 . . ? C9 C20 H20A 109.4 . . ? C19 C20 H20B 109.4 . . ? C9 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? O2 C21 O3 124.67(11) . . ? O2 C21 C9 124.72(11) . . ? O3 C21 C9 110.47(9) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C8 N1 C9 121.66(10) . . ? C8 N1 H1N 117.2(10) . . ? C9 N1 H1N 119.2(10) . . ? C21 O3 C22 115.60(9) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.328 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.040 #===END data_compound13 _database_code_depnum_ccdc_archive 'CCDC 829856' #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 N O3' _chemical_formula_weight 321.36 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.149(6) _cell_length_b 7.5081(15) _cell_length_c 15.387(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.300(2) _cell_angle_gamma 90.00 _cell_volume 3215.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 123 _cell_measurement_reflns_used 1889 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9911 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8747 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3605 _reflns_number_gt 2614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0438P)^2^+1.5367P] 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 3605 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.08391(6) 0.6330(2) 0.45398(11) 0.0179(3) Uani 1 1 d . . . C2 C 0.04245(6) 0.5758(2) 0.38799(11) 0.0219(4) Uani 1 1 d . . . H2 H 0.0451 0.5044 0.3387 0.026 Uiso 1 1 calc R . . C3 C -0.00260(6) 0.6225(2) 0.39399(12) 0.0247(4) Uani 1 1 d . . . H3 H -0.0307 0.5823 0.3492 0.030 Uiso 1 1 calc R . . C4 C -0.00639(6) 0.7280(2) 0.46552(12) 0.0259(4) Uani 1 1 d . . . H4 H -0.0372 0.7619 0.4692 0.031 Uiso 1 1 calc R . . C5 C 0.03461(6) 0.7841(2) 0.53167(12) 0.0255(4) Uani 1 1 d . . . H5 H 0.0318 0.8562 0.5806 0.031 Uiso 1 1 calc R . . C6 C 0.07974(6) 0.7356(2) 0.52678(11) 0.0209(4) Uani 1 1 d . . . H6 H 0.1077 0.7722 0.5730 0.025 Uiso 1 1 calc R . . C7 C 0.13300(6) 0.5840(2) 0.44913(11) 0.0168(3) Uani 1 1 d . . . C8 C 0.17828(5) 0.4985(2) 0.33918(10) 0.0166(3) Uani 1 1 d . . . C9 C 0.19081(5) 0.3046(2) 0.37675(10) 0.0165(3) Uani 1 1 d . . . H9 H 0.1963 0.3116 0.4440 0.020 Uiso 1 1 calc R . . C10 C 0.23784(5) 0.2341(2) 0.36358(11) 0.0200(4) Uani 1 1 d . . . H10A H 0.2481 0.1267 0.4017 0.024 Uiso 1 1 calc R . . H10B H 0.2319 0.1986 0.2992 0.024 Uiso 1 1 calc R . . C11 C 0.27737(6) 0.3690(2) 0.38815(11) 0.0234(4) Uani 1 1 d . . . H11 H 0.3096 0.3282 0.4010 0.028 Uiso 1 1 calc R . . C12 C 0.26993(6) 0.5422(2) 0.39291(11) 0.0239(4) Uani 1 1 d . . . H12 H 0.2973 0.6179 0.4091 0.029 Uiso 1 1 calc R . . C13 C 0.22146(5) 0.6272(2) 0.37455(11) 0.0199(4) Uani 1 1 d . . . H13A H 0.2187 0.7232 0.3291 0.024 Uiso 1 1 calc R . . H13B H 0.2193 0.6834 0.4315 0.024 Uiso 1 1 calc R . . C14 C 0.16047(5) 0.5009(2) 0.23444(11) 0.0164(3) Uani 1 1 d . . . C15 C 0.14865(5) 0.1785(2) 0.33993(11) 0.0176(3) Uani 1 1 d . . . C16 C 0.14263(6) 0.0806(2) 0.25997(11) 0.0210(4) Uani 1 1 d . . . H16 H 0.1661 0.0886 0.2286 0.025 Uiso 1 1 calc R . . C17 C 0.10287(6) -0.0280(2) 0.22575(12) 0.0244(4) Uani 1 1 d . . . H17 H 0.0995 -0.0940 0.1715 0.029 Uiso 1 1 calc R . . C18 C 0.06800(6) -0.0412(2) 0.26986(12) 0.0261(4) Uani 1 1 d . . . H18 H 0.0405 -0.1137 0.2455 0.031 Uiso 1 1 calc R . . C19 C 0.07366(6) 0.0527(2) 0.35007(12) 0.0258(4) Uani 1 1 d . . . H19 H 0.0500 0.0437 0.3811 0.031 Uiso 1 1 calc R . . C20 C 0.11380(6) 0.1596(2) 0.38511(11) 0.0216(4) Uani 1 1 d . . . H20 H 0.1176 0.2211 0.4408 0.026 Uiso 1 1 calc R . . H1H H 0.1123(7) 0.591(3) 0.3192(14) 0.033(5) Uiso 1 1 d . . . N1 N 0.13675(5) 0.56536(18) 0.36511(9) 0.0167(3) Uani 1 1 d . . . O1 O 0.16776(4) 0.56110(16) 0.51868(7) 0.0205(3) Uani 1 1 d . . . O2 O 0.12076(4) 0.55148(16) 0.19137(8) 0.0242(3) Uani 1 1 d . . . O3 O 0.19314(4) 0.44528(16) 0.19667(7) 0.0207(3) Uani 1 1 d . . . H3A H 0.1814 0.4453 0.1398 0.031 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 0.0191(8) 0.0195(9) 0.0160(8) 0.0042(7) 0.0067(6) 0.0017(7) C2 0.0225(9) 0.0257(9) 0.0181(8) 0.0027(7) 0.0070(7) 0.0008(7) C3 0.0194(9) 0.0296(10) 0.0237(9) 0.0071(8) 0.0039(7) 0.0000(7) C4 0.0193(9) 0.0311(10) 0.0301(10) 0.0106(8) 0.0114(7) 0.0090(7) C5 0.0303(10) 0.0251(10) 0.0251(9) 0.0031(8) 0.0143(7) 0.0060(8) C6 0.0224(8) 0.0237(9) 0.0171(8) 0.0014(7) 0.0067(6) 0.0019(7) C7 0.0204(8) 0.0152(8) 0.0154(8) -0.0005(6) 0.0062(6) -0.0013(6) C8 0.0147(8) 0.0217(9) 0.0134(8) -0.0010(6) 0.0042(6) -0.0003(6) C9 0.0164(8) 0.0208(9) 0.0120(7) 0.0014(6) 0.0036(6) 0.0005(6) C10 0.0172(8) 0.0240(9) 0.0185(8) 0.0017(7) 0.0047(6) 0.0025(7) C11 0.0153(8) 0.0353(10) 0.0192(9) 0.0025(7) 0.0046(6) 0.0008(7) C12 0.0184(8) 0.0357(11) 0.0171(8) -0.0001(7) 0.0045(6) -0.0076(7) C13 0.0222(9) 0.0225(9) 0.0153(8) -0.0028(7) 0.0064(6) -0.0043(7) C14 0.0181(8) 0.0156(8) 0.0158(8) -0.0003(6) 0.0055(6) -0.0030(6) C15 0.0173(8) 0.0175(8) 0.0175(8) 0.0038(6) 0.0043(6) 0.0018(6) C16 0.0230(9) 0.0226(9) 0.0184(9) 0.0001(7) 0.0075(7) 0.0001(7) C17 0.0288(9) 0.0213(9) 0.0207(9) -0.0010(7) 0.0038(7) -0.0009(7) C18 0.0222(9) 0.0208(10) 0.0327(10) 0.0023(8) 0.0041(7) -0.0049(7) C19 0.0230(9) 0.0267(10) 0.0306(10) 0.0032(8) 0.0124(7) -0.0017(8) C20 0.0230(9) 0.0229(9) 0.0202(9) 0.0024(7) 0.0087(7) -0.0001(7) N1 0.0164(7) 0.0217(7) 0.0117(7) 0.0001(5) 0.0036(5) 0.0019(6) O1 0.0187(6) 0.0297(7) 0.0123(6) -0.0006(5) 0.0035(4) 0.0022(5) O2 0.0230(6) 0.0326(7) 0.0152(6) -0.0009(5) 0.0027(5) 0.0061(5) O3 0.0202(6) 0.0318(7) 0.0110(5) -0.0004(5) 0.0058(4) 0.0002(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 C1 C6 1.394(2) . ? C1 C2 1.395(2) . ? C1 C7 1.500(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.2477(18) . ? C7 N1 1.337(2) . ? C8 N1 1.4709(19) . ? C8 C14 1.539(2) . ? C8 C13 1.552(2) . ? C8 C9 1.569(2) . ? C9 C15 1.521(2) . ? C9 C10 1.538(2) . ? C9 H9 1.0000 . ? C10 C11 1.496(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.324(3) . ? C11 H11 0.9500 . ? C12 C13 1.499(2) . ? C12 H12 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O2 1.2110(19) . ? C14 O3 1.3225(18) . ? C15 C16 1.399(2) . ? C15 C20 1.398(2) . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.388(3) . ? C18 H18 0.9500 . ? C19 C20 1.389(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? N1 H1H 0.86(2) . ? O3 H3A 0.8400 . ? 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 C6 C1 C2 119.43(15) . . ? C6 C1 C7 119.17(14) . . ? C2 C1 C7 121.39(14) . . ? C3 C2 C1 120.36(16) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 119.83(16) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.12(16) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.32(16) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.93(16) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 N1 122.40(14) . . ? O1 C7 C1 122.31(14) . . ? N1 C7 C1 115.29(14) . . ? N1 C8 C14 103.38(12) . . ? N1 C8 C13 109.85(13) . . ? C14 C8 C13 110.22(13) . . ? N1 C8 C9 109.69(12) . . ? C14 C8 C9 111.46(13) . . ? C13 C8 C9 111.90(12) . . ? C15 C9 C10 112.92(13) . . ? C15 C9 C8 111.50(12) . . ? C10 C9 C8 112.97(12) . . ? C15 C9 H9 106.3 . . ? C10 C9 H9 106.3 . . ? C8 C9 H9 106.3 . . ? C11 C10 C9 112.53(14) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 123.53(15) . . ? C12 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? C11 C12 C13 124.67(15) . . ? C11 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? C12 C13 C8 114.94(14) . . ? C12 C13 H13A 108.5 . . ? C8 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C8 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? O2 C14 O3 123.68(14) . . ? O2 C14 C8 123.13(14) . . ? O3 C14 C8 113.18(13) . . ? C16 C15 C20 117.67(15) . . ? C16 C15 C9 122.07(14) . . ? C20 C15 C9 120.25(14) . . ? C17 C16 C15 121.02(15) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C16 120.58(16) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.32(16) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C20 120.16(16) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 121.21(16) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? C7 N1 C8 127.49(14) . . ? C7 N1 H1H 118.8(13) . . ? C8 N1 H1H 113.6(13) . . ? C14 O3 H3A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.282 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.047