# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Hsung, Richard' _publ_contact_author_email rhsung@wisc.edu _publ_section_title ; A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides ; _publ_author_name 'Richard Hsung' # Attachment '12-Major_07029.cif' data_07029 _database_code_depnum_ccdc_archive 'CCDC 680316' #TrackingRef '12-Major_07029.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 07029 _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N O5' _chemical_formula_sum 'C17 H17 N O5' _chemical_formula_weight 315.32 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.419(2) _cell_length_b 12.174(3) _cell_length_c 13.334(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1529.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2896 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9751 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9785 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1562 _reflns_number_gt 1464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.3006P] 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), 1132 Friedel Pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1562 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 1.01136(16) 0.03568(15) 0.83603(11) 0.0484(4) Uani 1 1 d . . . O2 O 0.88764(17) -0.12114(13) 0.81711(12) 0.0462(4) Uani 1 1 d . . . O3 O 0.96010(16) 0.07272(13) 0.54773(11) 0.0438(4) Uani 1 1 d . . . O4 O 0.74487(16) 0.17569(12) 0.90932(11) 0.0416(4) Uani 1 1 d . . . O5 O 0.92090(16) 0.30068(12) 0.89912(11) 0.0381(4) Uani 1 1 d . . . N1 N 0.81482(17) 0.02555(14) 0.73329(12) 0.0304(4) Uani 1 1 d . . . C1 C 0.9144(2) -0.01290(19) 0.79751(15) 0.0367(5) Uani 1 1 d . . . C2 C 0.7685(3) -0.1582(2) 0.7578(2) 0.0517(6) Uani 1 1 d . . . H2A H 0.6867 -0.1760 0.8015 0.062 Uiso 1 1 calc R . . H2B H 0.7943 -0.2246 0.7190 0.062 Uiso 1 1 calc R . . C3 C 0.7317(2) -0.06331(16) 0.68711(16) 0.0327(5) Uani 1 1 d . . . H3 H 0.7697 -0.0793 0.6186 0.039 Uiso 1 1 calc R . . C4 C 0.5754(2) -0.03605(15) 0.68002(15) 0.0291(4) Uani 1 1 d . . . C5 C 0.4954(2) -0.01274(18) 0.76511(16) 0.0359(5) Uani 1 1 d . . . H5 H 0.5382 -0.0156 0.8296 0.043 Uiso 1 1 calc R . . C6 C 0.3535(2) 0.01458(19) 0.75576(18) 0.0423(5) Uani 1 1 d . . . H6 H 0.2991 0.0305 0.8140 0.051 Uiso 1 1 calc R . . C7 C 0.2904(2) 0.01882(17) 0.66256(19) 0.0461(6) Uani 1 1 d . . . H7 H 0.1927 0.0369 0.6566 0.055 Uiso 1 1 calc R . . C8 C 0.3694(3) -0.00311(18) 0.57822(18) 0.0436(6) Uani 1 1 d . . . H8 H 0.3262 0.0004 0.5139 0.052 Uiso 1 1 calc R . . C9 C 0.5114(2) -0.03022(16) 0.58664(16) 0.0349(5) Uani 1 1 d . . . H9 H 0.5655 -0.0449 0.5280 0.042 Uiso 1 1 calc R . . C10 C 0.81983(19) 0.13066(16) 0.68824(14) 0.0290(4) Uani 1 1 d . . . C11 C 0.8838(2) 0.14062(17) 0.58570(15) 0.0331(5) Uani 1 1 d . . . C12 C 0.8279(3) 0.24440(19) 0.53746(16) 0.0420(5) Uani 1 1 d . . . H12A H 0.8149 0.2341 0.4644 0.050 Uiso 1 1 calc R . . H12B H 0.8939 0.3065 0.5487 0.050 Uiso 1 1 calc R . . C13 C 0.6853(2) 0.26535(18) 0.58913(17) 0.0408(5) Uani 1 1 d . . . H13A H 0.6669 0.3451 0.5951 0.049 Uiso 1 1 calc R . . H13B H 0.6068 0.2312 0.5508 0.049 Uiso 1 1 calc R . . C14 C 0.6990(2) 0.21311(16) 0.69200(16) 0.0315(5) Uani 1 1 d . . . H14 H 0.6107 0.1936 0.7297 0.038 Uiso 1 1 calc R . . C15 C 0.8316(2) 0.23695(17) 0.74952(15) 0.0329(5) Uani 1 1 d . . . H15 H 0.8945 0.2952 0.7209 0.040 Uiso 1 1 calc R . . C16 C 0.8255(2) 0.23089(17) 0.86093(16) 0.0336(5) Uani 1 1 d . . . C17 C 0.9188(3) 0.31296(19) 1.00711(15) 0.0457(6) Uani 1 1 d . . . H17A H 0.9699 0.3800 1.0259 0.068 Uiso 1 1 calc R . . H17B H 0.9648 0.2493 1.0382 0.068 Uiso 1 1 calc R . . H17C H 0.8202 0.3179 1.0303 0.068 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 0.0297(8) 0.0792(12) 0.0363(8) -0.0028(8) -0.0058(7) 0.0141(9) O2 0.0470(9) 0.0500(9) 0.0415(9) 0.0155(7) 0.0063(8) 0.0203(8) O3 0.0459(9) 0.0451(9) 0.0403(8) 0.0017(7) 0.0123(8) 0.0026(8) O4 0.0379(8) 0.0501(9) 0.0368(8) -0.0024(7) 0.0072(8) -0.0094(8) O5 0.0407(8) 0.0394(8) 0.0343(8) -0.0033(6) -0.0066(7) -0.0065(7) N1 0.0256(8) 0.0354(9) 0.0301(8) 0.0067(7) -0.0014(7) 0.0033(7) C1 0.0282(11) 0.0551(14) 0.0268(10) 0.0026(10) 0.0042(9) 0.0158(11) C2 0.0443(13) 0.0450(13) 0.0660(16) 0.0197(12) -0.0007(13) 0.0044(12) C3 0.0336(10) 0.0295(10) 0.0350(10) 0.0025(9) 0.0056(10) 0.0008(9) C4 0.0330(10) 0.0218(9) 0.0324(10) 0.0017(8) 0.0030(9) -0.0052(8) C5 0.0330(10) 0.0437(12) 0.0310(11) 0.0020(9) 0.0016(9) -0.0075(10) C6 0.0330(11) 0.0429(12) 0.0511(14) -0.0015(11) 0.0096(10) -0.0056(10) C7 0.0320(12) 0.0353(12) 0.0710(17) 0.0059(12) -0.0093(12) -0.0033(10) C8 0.0504(14) 0.0354(12) 0.0448(13) 0.0068(10) -0.0177(11) -0.0085(10) C9 0.0473(13) 0.0263(10) 0.0311(10) 0.0010(9) -0.0014(10) -0.0066(10) C10 0.0231(9) 0.0329(10) 0.0309(10) 0.0013(9) -0.0018(9) -0.0014(8) C11 0.0295(10) 0.0376(11) 0.0322(10) -0.0003(9) 0.0007(9) -0.0045(9) C12 0.0496(13) 0.0435(12) 0.0330(11) 0.0065(10) -0.0026(11) -0.0004(11) C13 0.0402(12) 0.0369(12) 0.0452(12) 0.0058(10) -0.0113(11) 0.0035(10) C14 0.0245(10) 0.0311(10) 0.0390(11) 0.0010(9) -0.0017(9) -0.0004(8) C15 0.0286(11) 0.0360(11) 0.0342(11) -0.0020(9) 0.0020(9) -0.0069(9) C16 0.0280(10) 0.0355(11) 0.0375(11) -0.0035(9) -0.0005(10) 0.0001(10) C17 0.0608(15) 0.0405(12) 0.0356(12) -0.0049(10) -0.0123(12) -0.0022(12) _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 1.203(3) . ? O2 C1 1.367(3) . ? O2 C2 1.445(3) . ? O3 C11 1.207(2) . ? O4 C16 1.202(2) . ? O5 C16 1.337(2) . ? O5 C17 1.448(2) . ? N1 C1 1.354(3) . ? N1 C10 1.414(3) . ? N1 C3 1.471(3) . ? C2 C3 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.512(3) . ? C3 H3 1.0000 . ? C4 C9 1.385(3) . ? C4 C5 1.391(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7 C8 1.375(3) . ? C7 H7 0.9500 . ? C8 C9 1.383(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.499(3) . ? C10 C14 1.519(3) . ? C10 C15 1.534(3) . ? C11 C12 1.512(3) . ? C12 C13 1.531(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.517(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.494(3) . ? C14 H14 1.0000 . ? C15 C16 1.488(3) . ? C15 H15 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 109.87(17) . . ? C16 O5 C17 115.78(18) . . ? C1 N1 C10 123.94(18) . . ? C1 N1 C3 112.30(17) . . ? C10 N1 C3 120.36(16) . . ? O1 C1 N1 128.8(2) . . ? O1 C1 O2 122.2(2) . . ? N1 C1 O2 109.1(2) . . ? O2 C2 C3 106.09(19) . . ? O2 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? O2 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? N1 C3 C4 112.53(17) . . ? N1 C3 C2 100.18(17) . . ? C4 C3 C2 115.15(18) . . ? N1 C3 H3 109.5 . . ? C4 C3 H3 109.5 . . ? C2 C3 H3 109.5 . . ? C9 C4 C5 119.2(2) . . ? C9 C4 C3 119.38(19) . . ? C5 C4 C3 121.41(19) . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.2(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 120.4(2) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? N1 C10 C11 118.29(17) . . ? N1 C10 C14 123.98(17) . . ? C11 C10 C14 106.14(16) . . ? N1 C10 C15 122.63(16) . . ? C11 C10 C15 112.87(16) . . ? C14 C10 C15 58.60(13) . . ? O3 C11 C10 124.52(19) . . ? O3 C11 C12 126.95(19) . . ? C10 C11 C12 108.40(17) . . ? C11 C12 C13 104.66(17) . . ? C11 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? C11 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? C14 C13 C12 105.24(17) . . ? C14 C13 H13A 110.7 . . ? C12 C13 H13A 110.7 . . ? C14 C13 H13B 110.7 . . ? C12 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 116.95(18) . . ? C15 C14 C10 61.23(13) . . ? C13 C14 C10 108.09(17) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C10 C14 H14 118.9 . . ? C16 C15 C14 118.09(18) . . ? C16 C15 C10 119.13(18) . . ? C14 C15 C10 60.17(12) . . ? C16 C15 H15 116.0 . . ? C14 C15 H15 116.0 . . ? C10 C15 H15 116.0 . . ? O4 C16 O5 125.1(2) . . ? O4 C16 C15 126.0(2) . . ? O5 C16 C15 108.84(18) . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C1 O1 9.3(3) . . . . ? C3 N1 C1 O1 168.5(2) . . . . ? C10 N1 C1 O2 -172.42(17) . . . . ? C3 N1 C1 O2 -13.2(2) . . . . ? C2 O2 C1 O1 -178.0(2) . . . . ? C2 O2 C1 N1 3.7(2) . . . . ? C1 O2 C2 C3 6.6(2) . . . . ? C1 N1 C3 C4 138.98(18) . . . . ? C10 N1 C3 C4 -61.0(2) . . . . ? C1 N1 C3 C2 16.2(2) . . . . ? C10 N1 C3 C2 176.18(18) . . . . ? O2 C2 C3 N1 -13.0(2) . . . . ? O2 C2 C3 C4 -134.0(2) . . . . ? N1 C3 C4 C9 118.4(2) . . . . ? C2 C3 C4 C9 -127.7(2) . . . . ? N1 C3 C4 C5 -59.3(2) . . . . ? C2 C3 C4 C5 54.7(3) . . . . ? C9 C4 C5 C6 0.7(3) . . . . ? C3 C4 C5 C6 178.37(19) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C7 C8 C9 C4 0.3(3) . . . . ? C5 C4 C9 C8 -0.9(3) . . . . ? C3 C4 C9 C8 -178.61(18) . . . . ? C1 N1 C10 C11 94.8(2) . . . . ? C3 N1 C10 C11 -62.7(2) . . . . ? C1 N1 C10 C14 -127.1(2) . . . . ? C3 N1 C10 C14 75.3(2) . . . . ? C1 N1 C10 C15 -55.5(3) . . . . ? C3 N1 C10 C15 146.95(18) . . . . ? N1 C10 C11 O3 -18.0(3) . . . . ? C14 C10 C11 O3 -162.70(19) . . . . ? C15 C10 C11 O3 135.1(2) . . . . ? N1 C10 C11 C12 158.11(18) . . . . ? C14 C10 C11 C12 13.4(2) . . . . ? C15 C10 C11 C12 -48.8(2) . . . . ? O3 C11 C12 C13 150.6(2) . . . . ? C10 C11 C12 C13 -25.4(2) . . . . ? C11 C12 C13 C14 27.1(2) . . . . ? C12 C13 C14 C15 46.8(2) . . . . ? C12 C13 C14 C10 -19.5(2) . . . . ? N1 C10 C14 C15 110.5(2) . . . . ? C11 C10 C14 C15 -107.30(17) . . . . ? N1 C10 C14 C13 -138.11(19) . . . . ? C11 C10 C14 C13 4.1(2) . . . . ? C15 C10 C14 C13 111.38(19) . . . . ? C13 C14 C15 C16 153.93(19) . . . . ? C10 C14 C15 C16 -109.3(2) . . . . ? C13 C14 C15 C10 -96.80(19) . . . . ? N1 C10 C15 C16 -5.2(3) . . . . ? C11 C10 C15 C16 -156.93(18) . . . . ? C14 C10 C15 C16 107.6(2) . . . . ? N1 C10 C15 C14 -112.8(2) . . . . ? C11 C10 C15 C14 95.51(17) . . . . ? C17 O5 C16 O4 -3.4(3) . . . . ? C17 O5 C16 C15 174.02(18) . . . . ? C14 C15 C16 O4 26.7(3) . . . . ? C10 C15 C16 O4 -43.0(3) . . . . ? C14 C15 C16 O5 -150.74(17) . . . . ? C10 C15 C16 O5 139.63(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.109 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.035 # Attachment '14-major_08170a.cif' data_08170a _database_code_depnum_ccdc_archive 'CCDC 763759' #TrackingRef '14-major_08170a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 08170a _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N O3' _chemical_formula_sum 'C15 H15 N O3' _chemical_formula_weight 257.28 _chemical_absolute_configuration rm 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.293(2) _cell_length_b 6.0494(10) _cell_length_c 12.923(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.616(17) _cell_angle_gamma 90.00 _cell_volume 641.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1750 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.14 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9548 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details 'Z. F. Al-Rishad / Prof. R. Hsung - UW' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1573 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.29 _reflns_number_total 1573 _reflns_number_gt 1430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.1059P] 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 0.2(13) _refine_ls_number_reflns 1573 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.60718(17) 0.9895(2) 0.71474(11) 0.0418(4) Uani 1 1 d . . . O2 O 0.64592(17) 0.8035(3) 0.57003(10) 0.0430(4) Uani 1 1 d . . . O3 O 0.99446(16) 0.8463(3) 0.86394(10) 0.0418(4) Uani 1 1 d . . . N1 N 0.72451(17) 0.6442(3) 0.72350(11) 0.0289(3) Uani 1 1 d . . . C1 C 0.6554(2) 0.8267(3) 0.67515(14) 0.0311(4) Uani 1 1 d . . . C2 C 0.7004(2) 0.5849(4) 0.54624(15) 0.0425(5) Uani 1 1 d . . . H2A H 0.7814 0.5939 0.4974 0.051 Uiso 1 1 calc R . . H2B H 0.6071 0.4942 0.5135 0.051 Uiso 1 1 calc R . . C3 C 0.7779(2) 0.4819(3) 0.65110(13) 0.0290(4) Uani 1 1 d . . . H3A H 0.7254 0.3360 0.6606 0.035 Uiso 1 1 calc R . . C4 C 0.9613(2) 0.4527(3) 0.66349(13) 0.0289(4) Uani 1 1 d . . . C5 C 1.0624(2) 0.6178(4) 0.63571(17) 0.0416(5) Uani 1 1 d . . . H5A H 1.0174 0.7546 0.6092 0.050 Uiso 1 1 calc R . . C6 C 1.2299(3) 0.5830(5) 0.6466(2) 0.0516(6) Uani 1 1 d . . . H6A H 1.2990 0.6962 0.6273 0.062 Uiso 1 1 calc R . . C7 C 1.2961(3) 0.3857(4) 0.68519(17) 0.0459(6) Uani 1 1 d . . . H7A H 1.4105 0.3624 0.6918 0.055 Uiso 1 1 calc R . . C8 C 1.1968(3) 0.2222(4) 0.71414(15) 0.0435(5) Uani 1 1 d . . . H8A H 1.2425 0.0867 0.7417 0.052 Uiso 1 1 calc R . . C9 C 1.0292(2) 0.2556(3) 0.70294(14) 0.0355(4) Uani 1 1 d . . . H9A H 0.9607 0.1419 0.7226 0.043 Uiso 1 1 calc R . . C10 C 0.7499(2) 0.6296(3) 0.83444(13) 0.0277(4) Uani 1 1 d . . . C11 C 0.8786(2) 0.7664(3) 0.89719(14) 0.0304(4) Uani 1 1 d . . . C12 C 0.8363(2) 0.7959(4) 1.00608(14) 0.0366(4) Uani 1 1 d . . . H12A H 0.8643 0.9469 1.0324 0.044 Uiso 1 1 calc R . . H12B H 0.8960 0.6876 1.0550 0.044 Uiso 1 1 calc R . . C13 C 0.6522(2) 0.7569(4) 0.99527(15) 0.0425(5) Uani 1 1 d . . . H13A H 0.6242 0.6784 1.0574 0.051 Uiso 1 1 calc R . . H13B H 0.5925 0.8991 0.9877 0.051 Uiso 1 1 calc R . . C14 C 0.6091(2) 0.6164(4) 0.89738(14) 0.0354(4) Uani 1 1 d . . . H14A H 0.4950 0.6213 0.8592 0.043 Uiso 1 1 calc R . . C15 C 0.7087(2) 0.4167(3) 0.88740(15) 0.0355(4) Uani 1 1 d . . . H15A H 0.6583 0.2956 0.8422 0.043 Uiso 1 1 calc R . . H15B H 0.7838 0.3677 0.9500 0.043 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 0.0463(8) 0.0311(8) 0.0480(8) 0.0019(7) 0.0069(6) 0.0066(7) O2 0.0499(8) 0.0484(10) 0.0297(7) 0.0077(7) 0.0023(6) 0.0086(7) O3 0.0410(7) 0.0440(8) 0.0409(7) 0.0012(7) 0.0081(6) -0.0130(7) N1 0.0320(7) 0.0301(9) 0.0250(7) -0.0007(6) 0.0057(6) 0.0025(7) C1 0.0274(8) 0.0327(10) 0.0327(9) 0.0034(8) 0.0029(7) -0.0033(8) C2 0.0398(10) 0.0553(14) 0.0313(10) -0.0049(10) 0.0018(8) 0.0041(10) C3 0.0315(9) 0.0286(9) 0.0278(8) -0.0023(8) 0.0068(7) -0.0030(8) C4 0.0327(9) 0.0302(10) 0.0247(8) -0.0038(7) 0.0071(6) -0.0006(8) C5 0.0387(10) 0.0318(11) 0.0564(12) 0.0028(10) 0.0144(9) 0.0000(9) C6 0.0371(11) 0.0508(15) 0.0706(15) -0.0067(12) 0.0203(10) -0.0086(11) C7 0.0338(10) 0.0596(16) 0.0434(11) -0.0154(11) 0.0032(8) 0.0083(10) C8 0.0493(11) 0.0460(13) 0.0331(10) -0.0021(9) -0.0004(8) 0.0142(10) C9 0.0449(10) 0.0329(10) 0.0289(9) 0.0020(8) 0.0067(7) 0.0024(9) C10 0.0292(8) 0.0289(9) 0.0258(8) 0.0019(7) 0.0070(6) 0.0019(8) C11 0.0343(9) 0.0249(9) 0.0317(9) 0.0026(8) 0.0038(7) 0.0023(8) C12 0.0438(10) 0.0371(11) 0.0285(9) -0.0013(8) 0.0037(7) -0.0013(9) C13 0.0438(11) 0.0535(14) 0.0324(10) -0.0054(10) 0.0133(8) 0.0061(11) C14 0.0294(8) 0.0473(12) 0.0311(9) 0.0002(9) 0.0097(7) -0.0022(9) C15 0.0413(10) 0.0339(11) 0.0316(9) 0.0046(8) 0.0063(7) -0.0078(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 C1 1.206(2) . ? O2 C1 1.356(2) . ? O2 C2 1.445(3) . ? O3 C11 1.210(2) . ? N1 C1 1.353(2) . ? N1 C10 1.420(2) . ? N1 C3 1.470(2) . ? C2 C3 1.542(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(2) . ? C3 H3A 1.0000 . ? C4 C9 1.383(3) . ? C4 C5 1.386(3) . ? C5 C6 1.391(3) . ? C5 H5A 0.9500 . ? C6 C7 1.376(4) . ? C6 H6A 0.9500 . ? C7 C8 1.374(3) . ? C7 H7A 0.9500 . ? C8 C9 1.390(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.491(2) . ? C10 C15 1.522(3) . ? C10 C14 1.522(2) . ? C11 C12 1.511(2) . ? C12 C13 1.530(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.521(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.480(3) . ? C14 H14A 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 109.56(16) . . ? C1 N1 C10 120.37(15) . . ? C1 N1 C3 113.47(14) . . ? C10 N1 C3 126.01(15) . . ? O1 C1 N1 127.97(17) . . ? O1 C1 O2 122.45(18) . . ? N1 C1 O2 109.58(17) . . ? O2 C2 C3 106.57(16) . . ? O2 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? N1 C3 C4 113.83(14) . . ? N1 C3 C2 99.43(15) . . ? C4 C3 C2 114.84(15) . . ? N1 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C9 C4 C5 119.20(17) . . ? C9 C4 C3 119.11(17) . . ? C5 C4 C3 121.69(17) . . ? C4 C5 C6 119.9(2) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C8 C7 C6 119.99(19) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C4 C9 C8 120.61(19) . . ? C4 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? N1 C10 C11 120.04(15) . . ? N1 C10 C15 119.82(16) . . ? C11 C10 C15 114.60(15) . . ? N1 C10 C14 122.20(15) . . ? C11 C10 C14 106.42(14) . . ? C15 C10 C14 58.17(12) . . ? O3 C11 C10 124.77(16) . . ? O3 C11 C12 126.23(17) . . ? C10 C11 C12 108.95(15) . . ? C11 C12 C13 105.35(15) . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 105.59(15) . . ? C14 C13 H13A 110.6 . . ? C12 C13 H13A 110.6 . . ? C14 C13 H13B 110.6 . . ? C12 C13 H13B 110.6 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 117.65(17) . . ? C15 C14 C10 60.90(12) . . ? C13 C14 C10 108.15(16) . . ? C15 C14 H14A 118.7 . . ? C13 C14 H14A 118.7 . . ? C10 C14 H14A 118.7 . . ? C14 C15 C10 60.93(13) . . ? C14 C15 H15A 117.7 . . ? C10 C15 H15A 117.7 . . ? C14 C15 H15B 117.7 . . ? C10 C15 H15B 117.7 . . ? H15A C15 H15B 114.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C1 O1 -0.9(3) . . . . ? C3 N1 C1 O1 -176.55(18) . . . . ? C10 N1 C1 O2 179.17(15) . . . . ? C3 N1 C1 O2 3.5(2) . . . . ? C2 O2 C1 O1 -175.22(17) . . . . ? C2 O2 C1 N1 4.7(2) . . . . ? C1 O2 C2 C3 -10.5(2) . . . . ? C1 N1 C3 C4 113.32(17) . . . . ? C10 N1 C3 C4 -62.1(2) . . . . ? C1 N1 C3 C2 -9.29(18) . . . . ? C10 N1 C3 C2 175.32(17) . . . . ? O2 C2 C3 N1 11.36(18) . . . . ? O2 C2 C3 C4 -110.52(18) . . . . ? N1 C3 C4 C9 111.25(19) . . . . ? C2 C3 C4 C9 -135.05(18) . . . . ? N1 C3 C4 C5 -69.2(2) . . . . ? C2 C3 C4 C5 44.5(2) . . . . ? C9 C4 C5 C6 0.7(3) . . . . ? C3 C4 C5 C6 -178.89(18) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C5 C4 C9 C8 -0.4(3) . . . . ? C3 C4 C9 C8 179.20(17) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C1 N1 C10 C11 -71.6(2) . . . . ? C3 N1 C10 C11 103.5(2) . . . . ? C1 N1 C10 C15 136.03(17) . . . . ? C3 N1 C10 C15 -48.9(2) . . . . ? C1 N1 C10 C14 67.0(2) . . . . ? C3 N1 C10 C14 -117.9(2) . . . . ? N1 C10 C11 O3 -21.2(3) . . . . ? C15 C10 C11 O3 132.49(19) . . . . ? C14 C10 C11 O3 -165.54(18) . . . . ? N1 C10 C11 C12 156.37(16) . . . . ? C15 C10 C11 C12 -49.9(2) . . . . ? C14 C10 C11 C12 12.0(2) . . . . ? O3 C11 C12 C13 155.3(2) . . . . ? C10 C11 C12 C13 -22.2(2) . . . . ? C11 C12 C13 C14 23.3(2) . . . . ? C12 C13 C14 C15 49.6(2) . . . . ? C12 C13 C14 C10 -16.4(2) . . . . ? N1 C10 C14 C15 107.5(2) . . . . ? C11 C10 C14 C15 -109.14(16) . . . . ? N1 C10 C14 C13 -140.39(19) . . . . ? C11 C10 C14 C13 3.0(2) . . . . ? C15 C10 C14 C13 112.11(19) . . . . ? C13 C14 C15 C10 -96.37(18) . . . . ? N1 C10 C15 C14 -111.54(17) . . . . ? C11 C10 C15 C14 94.69(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.142 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.030 # Attachment '17-major_09021a.cif' data_09021a _database_code_depnum_ccdc_archive 'CCDC 763760' #TrackingRef '17-major_09021a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09021a _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O3' _chemical_formula_sum 'C16 H17 N O3' _chemical_formula_weight 271.31 _chemical_absolute_configuration rm 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.821(3) _cell_length_b 5.9677(17) _cell_length_c 29.515(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.257(4) _cell_angle_gamma 90.00 _cell_volume 2076.4(10) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2709 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.02 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9563 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details 'H. Li - Prof. R. Hsung / University of Wisconsin' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20633 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.10 _reflns_number_total 7331 _reflns_number_gt 5739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-97 _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.4637P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.0(9) _refine_ls_number_reflns 7331 _refine_ls_number_parameters 541 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 O1A O 0.30070(16) -0.0954(3) 0.51568(6) 0.0375(5) Uani 1 1 d . . . O2A O 0.13961(15) 0.1033(4) 0.50451(6) 0.0418(5) Uani 1 1 d . . . O3A O 0.34044(15) 0.0003(4) 0.62508(6) 0.0386(5) Uani 1 1 d . . . N1A N 0.28427(16) 0.2637(4) 0.54342(7) 0.0263(5) Uani 1 1 d . . . C1A C 0.2486(2) 0.0773(5) 0.52104(8) 0.0301(7) Uani 1 1 d . . . C2A C 0.1095(2) 0.3362(6) 0.51096(9) 0.0423(8) Uani 1 1 d . . . H2AA H 0.0291 0.3502 0.5178 0.051 Uiso 1 1 calc R . . H2AB H 0.1219 0.4255 0.4835 0.051 Uiso 1 1 calc R . . C3A C 0.1881(2) 0.4125(5) 0.55094(8) 0.0285(6) Uani 1 1 d . . . H3AA H 0.2094 0.5736 0.5479 0.034 Uiso 1 1 calc R . . C4A C 0.3907(2) 0.2640(5) 0.56905(8) 0.0242(6) Uani 1 1 d . . . C5A C 0.4134(2) 0.1004(5) 0.60660(9) 0.0289(6) Uani 1 1 d . . . C6A C 0.5400(2) 0.0737(5) 0.61624(9) 0.0360(7) Uani 1 1 d . . . H6AA H 0.5596 -0.0832 0.6244 0.043 Uiso 1 1 calc R . . H6AB H 0.5685 0.1730 0.6414 0.043 Uiso 1 1 calc R . . C7A C 0.5905(2) 0.1409(5) 0.57154(9) 0.0374(7) Uani 1 1 d . . . H7AA H 0.6636 0.2200 0.5778 0.045 Uiso 1 1 calc R . . H7AB H 0.6032 0.0069 0.5528 0.045 Uiso 1 1 calc R . . C8A C 0.5036(2) 0.2937(5) 0.54761(9) 0.0334(7) Uani 1 1 d . . . H8AA H 0.5025 0.3079 0.5138 0.040 Uiso 1 1 calc R . . C9A C 0.4584(2) 0.4812(5) 0.57367(10) 0.0356(7) Uani 1 1 d . . . H9AA H 0.4283 0.6132 0.5564 0.043 Uiso 1 1 calc R . . H9AB H 0.4972 0.5161 0.6037 0.043 Uiso 1 1 calc R . . C10A C 0.1404(2) 0.3669(5) 0.59684(8) 0.0293(6) Uani 1 1 d . . . H10A H 0.1130 0.2102 0.5973 0.035 Uiso 1 1 calc R . . H10B H 0.2025 0.3823 0.6211 0.035 Uiso 1 1 calc R . . C11A C 0.0444(2) 0.5215(5) 0.60741(8) 0.0266(6) Uani 1 1 d . . . C12A C -0.0681(2) 0.4607(5) 0.59849(9) 0.0359(7) Uani 1 1 d . . . H12A H -0.0860 0.3187 0.5853 0.043 Uiso 1 1 calc R . . C13A C -0.1549(2) 0.6042(6) 0.60854(10) 0.0422(8) Uani 1 1 d . . . H13A H -0.2316 0.5609 0.6019 0.051 Uiso 1 1 calc R . . C14A C -0.1302(2) 0.8092(5) 0.62812(9) 0.0394(7) Uani 1 1 d . . . H14A H -0.1899 0.9072 0.6350 0.047 Uiso 1 1 calc R . . C15A C -0.0189(2) 0.8723(5) 0.63770(9) 0.0365(7) Uani 1 1 d . . . H15A H -0.0016 1.0126 0.6518 0.044 Uiso 1 1 calc R . . C16A C 0.0674(2) 0.7304(5) 0.62676(9) 0.0331(7) Uani 1 1 d . . . H16A H 0.1440 0.7767 0.6326 0.040 Uiso 1 1 calc R . . O1B O 0.55188(16) 0.3914(3) 0.80950(6) 0.0352(5) Uani 1 1 d . . . O2B O 0.70779(16) 0.5853(4) 0.83385(6) 0.0443(5) Uani 1 1 d . . . O3B O 0.57176(16) 0.4946(4) 0.69769(7) 0.0443(5) Uani 1 1 d . . . N1B N 0.58690(17) 0.7472(4) 0.78367(7) 0.0259(5) Uani 1 1 d . . . C1B C 0.6088(2) 0.5599(5) 0.80848(8) 0.0294(6) Uani 1 1 d . . . C2B C 0.7444(3) 0.8168(6) 0.82961(9) 0.0455(8) Uani 1 1 d . . . H2BA H 0.8280 0.8261 0.8293 0.055 Uiso 1 1 calc R . . H2BB H 0.7199 0.9091 0.8550 0.055 Uiso 1 1 calc R . . C3B C 0.6869(2) 0.8929(5) 0.78461(8) 0.0300(6) Uani 1 1 d . . . H3BA H 0.6641 1.0539 0.7862 0.036 Uiso 1 1 calc R . . C4B C 0.4955(2) 0.7518(4) 0.75004(8) 0.0248(6) Uani 1 1 d . . . C5B C 0.4902(2) 0.5901(5) 0.71129(9) 0.0307(6) Uani 1 1 d . . . C6B C 0.3686(2) 0.5605(5) 0.69362(9) 0.0360(7) Uani 1 1 d . . . H6BA H 0.3532 0.4022 0.6852 0.043 Uiso 1 1 calc R . . H6BB H 0.3508 0.6560 0.6666 0.043 Uiso 1 1 calc R . . C7B C 0.2981(2) 0.6311(6) 0.73270(10) 0.0410(8) Uani 1 1 d . . . H7BA H 0.2291 0.7127 0.7209 0.049 Uiso 1 1 calc R . . H7BB H 0.2748 0.4983 0.7498 0.049 Uiso 1 1 calc R . . C8B C 0.3738(2) 0.7814(5) 0.76274(9) 0.0338(7) Uani 1 1 d . . . H8BA H 0.3594 0.7938 0.7956 0.041 Uiso 1 1 calc R . . C9B C 0.4320(2) 0.9688(5) 0.74118(9) 0.0322(6) Uani 1 1 d . . . H9BA H 0.4550 1.0993 0.7604 0.039 Uiso 1 1 calc R . . H9BB H 0.4073 1.0059 0.7093 0.039 Uiso 1 1 calc R . . C10B C 0.7564(2) 0.8525(5) 0.74369(8) 0.0309(6) Uani 1 1 d . . . H10C H 0.7813 0.6940 0.7437 0.037 Uiso 1 1 calc R . . H10D H 0.7077 0.8788 0.7154 0.037 Uiso 1 1 calc R . . C11B C 0.8587(2) 1.0014(5) 0.74388(8) 0.0297(6) Uani 1 1 d . . . C12B C 0.9623(2) 0.9324(5) 0.76422(10) 0.0394(7) Uani 1 1 d . . . H12B H 0.9689 0.7889 0.7781 0.047 Uiso 1 1 calc R . . C13B C 1.0559(3) 1.0704(7) 0.76447(13) 0.0579(10) Uani 1 1 d . . . H13B H 1.1266 1.0219 0.7785 0.069 Uiso 1 1 calc R . . C14B C 1.0467(3) 1.2790(7) 0.74442(14) 0.0658(11) Uani 1 1 d . . . H14B H 1.1108 1.3752 0.7451 0.079 Uiso 1 1 calc R . . C15B C 0.9447(3) 1.3481(6) 0.72335(12) 0.0546(9) Uani 1 1 d . . . H15B H 0.9390 1.4896 0.7086 0.065 Uiso 1 1 calc R . . C16B C 0.8509(2) 1.2109(5) 0.72373(10) 0.0364(7) Uani 1 1 d . . . H16B H 0.7801 1.2607 0.7100 0.044 Uiso 1 1 calc R . . O1C O 0.10494(18) 0.6228(4) 0.85316(7) 0.0445(5) Uani 1 1 d . . . O2C O 0.26979(15) 0.4541(3) 0.84116(6) 0.0382(5) Uani 1 1 d . . . O3C O 0.12722(16) 0.4834(4) 0.97016(7) 0.0488(6) Uani 1 1 d . . . N1C N 0.15000(17) 0.2729(4) 0.88212(7) 0.0266(5) Uani 1 1 d . . . C1C C 0.1669(2) 0.4628(5) 0.85897(9) 0.0303(6) Uani 1 1 d . . . C2C C 0.3223(3) 0.2431(6) 0.85228(10) 0.0442(8) Uani 1 1 d . . . H2CA H 0.4003 0.2663 0.8661 0.053 Uiso 1 1 calc R . . H2CB H 0.3263 0.1508 0.8246 0.053 Uiso 1 1 calc R . . C3C C 0.2499(2) 0.1270(5) 0.88583(8) 0.0263(6) Uani 1 1 d . . . H3CA H 0.2291 -0.0271 0.8748 0.032 Uiso 1 1 calc R . . C4C C 0.0532(2) 0.2540(5) 0.90805(8) 0.0252(6) Uani 1 1 d . . . C5C C 0.0480(2) 0.3937(5) 0.94964(9) 0.0302(6) Uani 1 1 d . . . C6C C -0.0750(2) 0.4119(5) 0.96001(9) 0.0333(7) Uani 1 1 d . . . H6CA H -0.0909 0.5616 0.9725 0.040 Uiso 1 1 calc R . . H6CB H -0.0939 0.2964 0.9823 0.040 Uiso 1 1 calc R . . C7C C -0.1434(2) 0.3755(6) 0.91469(9) 0.0385(7) Uani 1 1 d . . . H7CA H -0.1624 0.5204 0.8997 0.046 Uiso 1 1 calc R . . H7CB H -0.2146 0.2935 0.9191 0.046 Uiso 1 1 calc R . . C8C C -0.0656(2) 0.2368(5) 0.88654(9) 0.0326(7) Uani 1 1 d . . . H8CA H -0.0775 0.2429 0.8527 0.039 Uiso 1 1 calc R . . C9C C -0.0116(2) 0.0355(5) 0.90777(10) 0.0348(7) Uani 1 1 d . . . H9CA H 0.0119 -0.0851 0.8874 0.042 Uiso 1 1 calc R . . H9CB H -0.0390 -0.0168 0.9368 0.042 Uiso 1 1 calc R . . C10C C 0.3058(2) 0.1166(6) 0.93390(9) 0.0395(7) Uani 1 1 d . . . H10E H 0.3139 0.2709 0.9460 0.047 Uiso 1 1 calc R . . H10F H 0.2557 0.0330 0.9533 0.047 Uiso 1 1 calc R . . C11C C 0.4209(2) 0.0063(5) 0.93683(8) 0.0315(6) Uani 1 1 d . . . C12C C 0.5125(2) 0.1108(5) 0.95988(9) 0.0319(6) Uani 1 1 d . . . H12C H 0.5024 0.2531 0.9734 0.038 Uiso 1 1 calc R . . C13C C 0.6184(2) 0.0120(6) 0.96350(9) 0.0391(7) Uani 1 1 d . . . H13C H 0.6800 0.0861 0.9797 0.047 Uiso 1 1 calc R . . C14C C 0.6353(2) -0.1928(6) 0.94380(9) 0.0408(8) Uani 1 1 d . . . H14C H 0.7083 -0.2603 0.9463 0.049 Uiso 1 1 calc R . . C15C C 0.5463(3) -0.2988(5) 0.92055(10) 0.0405(8) Uani 1 1 d . . . H15C H 0.5579 -0.4391 0.9064 0.049 Uiso 1 1 calc R . . C16C C 0.4392(2) -0.2028(5) 0.91750(9) 0.0382(7) Uani 1 1 d . . . H16C H 0.3775 -0.2802 0.9021 0.046 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 O1A 0.0404(11) 0.0367(12) 0.0363(11) -0.0078(9) 0.0101(9) 0.0031(10) O2A 0.0321(11) 0.0579(15) 0.0351(11) -0.0128(10) -0.0004(9) 0.0047(10) O3A 0.0384(11) 0.0408(12) 0.0376(11) 0.0125(10) 0.0092(9) -0.0040(10) N1A 0.0226(11) 0.0294(13) 0.0275(11) 0.0013(10) 0.0064(9) 0.0020(10) C1A 0.0293(15) 0.0403(19) 0.0210(13) 0.0006(13) 0.0046(11) -0.0014(14) C2A 0.0376(17) 0.063(2) 0.0261(15) 0.0053(15) 0.0045(12) 0.0152(15) C3A 0.0283(14) 0.0278(16) 0.0303(14) 0.0070(12) 0.0090(11) 0.0066(12) C4A 0.0232(13) 0.0245(14) 0.0259(13) -0.0019(11) 0.0078(10) -0.0011(11) C5A 0.0344(15) 0.0248(15) 0.0275(14) -0.0042(12) 0.0024(12) -0.0033(13) C6A 0.0349(16) 0.0354(18) 0.0368(16) -0.0054(13) -0.0032(12) 0.0009(14) C7A 0.0274(15) 0.0435(19) 0.0420(17) -0.0067(14) 0.0066(13) -0.0009(13) C8A 0.0279(15) 0.0432(18) 0.0302(14) 0.0003(14) 0.0098(11) -0.0027(13) C9A 0.0378(16) 0.0279(16) 0.0423(16) 0.0007(14) 0.0099(13) -0.0031(13) C10A 0.0303(14) 0.0315(16) 0.0267(14) 0.0020(12) 0.0058(11) 0.0023(12) C11A 0.0280(14) 0.0318(16) 0.0204(13) 0.0037(12) 0.0049(10) 0.0022(12) C12A 0.0322(16) 0.0412(18) 0.0350(15) -0.0074(14) 0.0063(12) -0.0003(14) C13A 0.0281(16) 0.053(2) 0.0458(18) -0.0018(16) 0.0070(13) -0.0004(15) C14A 0.0374(17) 0.0424(19) 0.0400(16) 0.0033(15) 0.0146(13) 0.0103(14) C15A 0.0436(18) 0.0314(17) 0.0359(16) -0.0040(13) 0.0130(13) -0.0004(14) C16A 0.0271(15) 0.0389(18) 0.0342(15) 0.0014(14) 0.0084(12) -0.0037(13) O1B 0.0385(11) 0.0330(12) 0.0347(11) 0.0051(9) 0.0063(8) -0.0073(10) O2B 0.0367(11) 0.0643(16) 0.0306(10) 0.0099(10) -0.0057(9) -0.0103(11) O3B 0.0411(12) 0.0508(14) 0.0413(11) -0.0187(11) 0.0049(9) 0.0040(11) N1B 0.0277(11) 0.0279(13) 0.0222(11) -0.0013(10) 0.0035(9) -0.0064(10) C1B 0.0310(15) 0.0370(18) 0.0208(13) 0.0005(12) 0.0054(11) -0.0007(14) C2B 0.0454(18) 0.063(2) 0.0276(15) -0.0038(15) -0.0009(13) -0.0266(16) C3B 0.0318(15) 0.0311(16) 0.0276(14) -0.0058(12) 0.0049(11) -0.0107(13) C4B 0.0247(13) 0.0247(14) 0.0253(13) 0.0019(12) 0.0044(10) -0.0031(12) C5B 0.0371(16) 0.0275(16) 0.0270(14) 0.0039(12) 0.0004(12) -0.0041(13) C6B 0.0439(17) 0.0281(16) 0.0345(15) 0.0013(13) -0.0084(12) -0.0052(13) C7B 0.0292(15) 0.053(2) 0.0403(17) 0.0096(15) 0.0003(13) -0.0069(14) C8B 0.0264(14) 0.0455(18) 0.0306(14) 0.0039(14) 0.0090(11) -0.0017(14) C9B 0.0356(15) 0.0301(16) 0.0311(14) 0.0004(13) 0.0048(12) 0.0012(13) C10B 0.0325(15) 0.0343(17) 0.0265(14) -0.0009(12) 0.0068(11) -0.0066(12) C11B 0.0301(15) 0.0331(16) 0.0264(14) -0.0069(13) 0.0069(11) -0.0047(13) C12B 0.0338(16) 0.0420(19) 0.0427(17) -0.0078(14) 0.0052(13) -0.0007(14) C13B 0.0278(17) 0.073(3) 0.073(2) -0.026(2) 0.0051(15) -0.0049(18) C14B 0.045(2) 0.065(3) 0.091(3) -0.024(2) 0.027(2) -0.029(2) C15B 0.058(2) 0.042(2) 0.068(2) -0.0105(18) 0.0356(18) -0.0125(17) C16B 0.0360(16) 0.0341(18) 0.0412(16) -0.0044(14) 0.0159(13) -0.0032(14) O1C 0.0543(13) 0.0342(12) 0.0460(12) 0.0052(10) 0.0115(10) 0.0067(11) O2C 0.0414(12) 0.0359(13) 0.0393(11) 0.0048(10) 0.0160(9) -0.0026(10) O3C 0.0307(11) 0.0672(15) 0.0478(12) -0.0246(12) -0.0015(9) 0.0037(11) N1C 0.0259(11) 0.0296(13) 0.0250(11) 0.0011(10) 0.0061(9) 0.0030(10) C1C 0.0334(15) 0.0281(17) 0.0294(14) -0.0044(13) 0.0034(12) -0.0018(13) C2C 0.0433(17) 0.0441(19) 0.0481(18) 0.0094(16) 0.0237(14) 0.0075(15) C3C 0.0239(13) 0.0286(15) 0.0270(13) -0.0042(12) 0.0066(11) 0.0006(12) C4C 0.0223(13) 0.0285(15) 0.0251(13) 0.0007(12) 0.0038(10) 0.0028(12) C5C 0.0314(15) 0.0332(16) 0.0256(14) 0.0001(13) -0.0001(12) 0.0063(13) C6C 0.0326(15) 0.0389(18) 0.0294(14) 0.0038(13) 0.0091(12) 0.0073(13) C7C 0.0258(15) 0.054(2) 0.0358(16) 0.0007(15) 0.0037(12) 0.0031(14) C8C 0.0279(15) 0.0421(18) 0.0273(14) -0.0015(14) -0.0011(11) 0.0011(14) C9C 0.0331(16) 0.0311(17) 0.0410(16) -0.0046(14) 0.0086(12) -0.0079(13) C10C 0.0336(16) 0.057(2) 0.0284(15) 0.0023(15) 0.0057(12) 0.0128(15) C11C 0.0319(15) 0.0414(17) 0.0222(13) 0.0005(13) 0.0081(11) 0.0070(13) C12C 0.0354(16) 0.0316(16) 0.0295(15) 0.0021(13) 0.0076(12) 0.0030(13) C13C 0.0322(16) 0.053(2) 0.0333(15) 0.0085(15) 0.0097(12) -0.0045(15) C14C 0.0333(16) 0.059(2) 0.0318(15) 0.0096(16) 0.0130(13) 0.0161(16) C15C 0.053(2) 0.0349(18) 0.0359(16) 0.0017(14) 0.0155(15) 0.0140(15) C16C 0.0382(17) 0.045(2) 0.0313(15) -0.0024(14) 0.0046(12) 0.0001(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 O1A C1A 1.217(3) . ? O2A C1A 1.352(3) . ? O2A C2A 1.450(4) . ? O3A C5A 1.212(3) . ? N1A C1A 1.346(4) . ? N1A C4A 1.419(3) . ? N1A C3A 1.473(3) . ? C2A C3A 1.516(4) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C3A C10A 1.530(3) . ? C3A H3AA 1.0000 . ? C4A C5A 1.486(4) . ? C4A C9A 1.524(4) . ? C4A C8A 1.529(3) . ? C5A C6A 1.511(4) . ? C6A C7A 1.541(4) . ? C6A H6AA 0.9900 . ? C6A H6AB 0.9900 . ? C7A C8A 1.509(4) . ? C7A H7AA 0.9900 . ? C7A H7AB 0.9900 . ? C8A C9A 1.480(4) . ? C8A H8AA 1.0000 . ? C9A H9AA 0.9900 . ? C9A H9AB 0.9900 . ? C10A C11A 1.513(3) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C12A 1.384(4) . ? C11A C16A 1.390(4) . ? C12A C13A 1.385(4) . ? C12A H12A 0.9500 . ? C13A C14A 1.375(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.377(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.383(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? O1B C1B 1.212(3) . ? O2B C1B 1.350(3) . ? O2B C2B 1.456(4) . ? O3B C5B 1.214(3) . ? N1B C1B 1.350(4) . ? N1B C4B 1.412(3) . ? N1B C3B 1.466(3) . ? C2B C3B 1.516(4) . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C3B C10B 1.530(3) . ? C3B H3BA 1.0000 . ? C4B C5B 1.494(4) . ? C4B C9B 1.510(4) . ? C4B C8B 1.524(3) . ? C5B C6B 1.503(4) . ? C6B C7B 1.532(4) . ? C6B H6BA 0.9900 . ? C6B H6BB 0.9900 . ? C7B C8B 1.508(4) . ? C7B H7BA 0.9900 . ? C7B H7BB 0.9900 . ? C8B C9B 1.481(4) . ? C8B H8BA 1.0000 . ? C9B H9BA 0.9900 . ? C9B H9BB 0.9900 . ? C10B C11B 1.500(4) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C16B 1.385(4) . ? C11B C12B 1.386(4) . ? C12B C13B 1.379(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.379(6) . ? C13B H13B 0.9500 . ? C14B C15B 1.379(5) . ? C14B H14B 0.9500 . ? C15B C16B 1.379(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? O1C C1C 1.207(3) . ? O2C C1C 1.362(3) . ? O2C C2C 1.431(4) . ? O3C C5C 1.202(3) . ? N1C C1C 1.346(3) . ? N1C C4C 1.427(3) . ? N1C C3C 1.465(3) . ? C2C C3C 1.523(4) . ? C2C H2CA 0.9900 . ? C2C H2CB 0.9900 . ? C3C C10C 1.521(4) . ? C3C H3CA 1.0000 . ? C4C C5C 1.489(4) . ? C4C C8C 1.502(3) . ? C4C C9C 1.512(4) . ? C5C C6C 1.512(4) . ? C6C C7C 1.526(4) . ? C6C H6CA 0.9900 . ? C6C H6CB 0.9900 . ? C7C C8C 1.528(4) . ? C7C H7CA 0.9900 . ? C7C H7CB 0.9900 . ? C8C C9C 1.478(4) . ? C8C H8CA 1.0000 . ? C9C H9CA 0.9900 . ? C9C H9CB 0.9900 . ? C10C C11C 1.508(4) . ? C10C H10E 0.9900 . ? C10C H10F 0.9900 . ? C11C C12C 1.384(4) . ? C11C C16C 1.395(4) . ? C12C C13C 1.380(4) . ? C12C H12C 0.9500 . ? C13C C14C 1.375(4) . ? C13C H13C 0.9500 . ? C14C C15C 1.368(4) . ? C14C H14C 0.9500 . ? C15C C16C 1.387(4) . ? C15C H15C 0.9500 . ? C16C H16C 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 C1A O2A C2A 107.4(2) . . ? C1A N1A C4A 119.7(2) . . ? C1A N1A C3A 110.8(2) . . ? C4A N1A C3A 125.7(2) . . ? O1A C1A N1A 128.4(2) . . ? O1A C1A O2A 121.9(3) . . ? N1A C1A O2A 109.7(2) . . ? O2A C2A C3A 104.4(2) . . ? O2A C2A H2AA 110.9 . . ? C3A C2A H2AA 110.9 . . ? O2A C2A H2AB 110.9 . . ? C3A C2A H2AB 110.9 . . ? H2AA C2A H2AB 108.9 . . ? N1A C3A C2A 97.8(2) . . ? N1A C3A C10A 111.4(2) . . ? C2A C3A C10A 113.1(2) . . ? N1A C3A H3AA 111.3 . . ? C2A C3A H3AA 111.3 . . ? C10A C3A H3AA 111.3 . . ? N1A C4A C5A 120.0(2) . . ? N1A C4A C9A 119.2(2) . . ? C5A C4A C9A 115.3(2) . . ? N1A C4A C8A 123.1(2) . . ? C5A C4A C8A 105.7(2) . . ? C9A C4A C8A 57.99(17) . . ? O3A C5A C4A 124.4(2) . . ? O3A C5A C6A 126.3(3) . . ? C4A C5A C6A 109.3(2) . . ? C5A C6A C7A 104.6(2) . . ? C5A C6A H6AA 110.8 . . ? C7A C6A H6AA 110.8 . . ? C5A C6A H6AB 110.8 . . ? C7A C6A H6AB 110.8 . . ? H6AA C6A H6AB 108.9 . . ? C8A C7A C6A 105.3(2) . . ? C8A C7A H7AA 110.7 . . ? C6A C7A H7AA 110.7 . . ? C8A C7A H7AB 110.7 . . ? C6A C7A H7AB 110.7 . . ? H7AA C7A H7AB 108.8 . . ? C9A C8A C7A 118.2(2) . . ? C9A C8A C4A 60.85(17) . . ? C7A C8A C4A 108.7(2) . . ? C9A C8A H8AA 118.4 . . ? C7A C8A H8AA 118.4 . . ? C4A C8A H8AA 118.4 . . ? C8A C9A C4A 61.15(17) . . ? C8A C9A H9AA 117.7 . . ? C4A C9A H9AA 117.7 . . ? C8A C9A H9AB 117.7 . . ? C4A C9A H9AB 117.7 . . ? H9AA C9A H9AB 114.8 . . ? C11A C10A C3A 113.9(2) . . ? C11A C10A H10A 108.8 . . ? C3A C10A H10A 108.8 . . ? C11A C10A H10B 108.8 . . ? C3A C10A H10B 108.8 . . ? H10A C10A H10B 107.7 . . ? C12A C11A C16A 118.0(2) . . ? C12A C11A C10A 121.7(3) . . ? C16A C11A C10A 120.3(2) . . ? C11A C12A C13A 120.9(3) . . ? C11A C12A H12A 119.6 . . ? C13A C12A H12A 119.6 . . ? C14A C13A C12A 120.2(3) . . ? C14A C13A H13A 119.9 . . ? C12A C13A H13A 119.9 . . ? C13A C14A C15A 119.9(3) . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C14A C15A C16A 119.7(3) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C15A C16A C11A 121.3(3) . . ? C15A C16A H16A 119.3 . . ? C11A C16A H16A 119.3 . . ? C1B O2B C2B 108.1(2) . . ? C1B N1B C4B 120.2(2) . . ? C1B N1B C3B 111.0(2) . . ? C4B N1B C3B 125.1(2) . . ? O1B C1B N1B 128.0(2) . . ? O1B C1B O2B 122.6(3) . . ? N1B C1B O2B 109.3(2) . . ? O2B C2B C3B 104.0(2) . . ? O2B C2B H2BA 110.9 . . ? C3B C2B H2BA 110.9 . . ? O2B C2B H2BB 110.9 . . ? C3B C2B H2BB 110.9 . . ? H2BA C2B H2BB 109.0 . . ? N1B C3B C2B 98.5(2) . . ? N1B C3B C10B 111.8(2) . . ? C2B C3B C10B 114.3(2) . . ? N1B C3B H3BA 110.6 . . ? C2B C3B H3BA 110.6 . . ? C10B C3B H3BA 110.6 . . ? N1B C4B C5B 120.8(2) . . ? N1B C4B C9B 118.9(2) . . ? C5B C4B C9B 115.4(2) . . ? N1B C4B C8B 121.1(2) . . ? C5B C4B C8B 106.1(2) . . ? C9B C4B C8B 58.46(17) . . ? O3B C5B C4B 124.6(2) . . ? O3B C5B C6B 126.3(3) . . ? C4B C5B C6B 109.1(2) . . ? C5B C6B C7B 105.4(2) . . ? C5B C6B H6BA 110.7 . . ? C7B C6B H6BA 110.7 . . ? C5B C6B H6BB 110.7 . . ? C7B C6B H6BB 110.7 . . ? H6BA C6B H6BB 108.8 . . ? C8B C7B C6B 105.9(2) . . ? C8B C7B H7BA 110.6 . . ? C6B C7B H7BA 110.6 . . ? C8B C7B H7BB 110.6 . . ? C6B C7B H7BB 110.6 . . ? H7BA C7B H7BB 108.7 . . ? C9B C8B C7B 118.1(2) . . ? C9B C8B C4B 60.31(17) . . ? C7B C8B C4B 108.4(2) . . ? C9B C8B H8BA 118.6 . . ? C7B C8B H8BA 118.6 . . ? C4B C8B H8BA 118.6 . . ? C8B C9B C4B 61.23(18) . . ? C8B C9B H9BA 117.6 . . ? C4B C9B H9BA 117.6 . . ? C8B C9B H9BB 117.6 . . ? C4B C9B H9BB 117.6 . . ? H9BA C9B H9BB 114.8 . . ? C11B C10B C3B 112.6(2) . . ? C11B C10B H10C 109.1 . . ? C3B C10B H10C 109.1 . . ? C11B C10B H10D 109.1 . . ? C3B C10B H10D 109.1 . . ? H10C C10B H10D 107.8 . . ? C16B C11B C12B 118.9(3) . . ? C16B C11B C10B 120.4(3) . . ? C12B C11B C10B 120.7(3) . . ? C13B C12B C11B 120.5(3) . . ? C13B C12B H12B 119.8 . . ? C11B C12B H12B 119.8 . . ? C14B C13B C12B 120.0(3) . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? C15B C14B C13B 120.1(3) . . ? C15B C14B H14B 119.9 . . ? C13B C14B H14B 119.9 . . ? C14B C15B C16B 119.7(4) . . ? C14B C15B H15B 120.1 . . ? C16B C15B H15B 120.1 . . ? C15B C16B C11B 120.8(3) . . ? C15B C16B H16B 119.6 . . ? C11B C16B H16B 119.6 . . ? C1C O2C C2C 109.3(2) . . ? C1C N1C C4C 119.6(2) . . ? C1C N1C C3C 112.9(2) . . ? C4C N1C C3C 125.9(2) . . ? O1C C1C N1C 128.8(2) . . ? O1C C1C O2C 121.7(3) . . ? N1C C1C O2C 109.5(2) . . ? O2C C2C C3C 107.1(2) . . ? O2C C2C H2CA 110.3 . . ? C3C C2C H2CA 110.3 . . ? O2C C2C H2CB 110.3 . . ? C3C C2C H2CB 110.3 . . ? H2CA C2C H2CB 108.5 . . ? N1C C3C C10C 112.7(2) . . ? N1C C3C C2C 99.8(2) . . ? C10C C3C C2C 113.5(2) . . ? N1C C3C H3CA 110.2 . . ? C10C C3C H3CA 110.2 . . ? C2C C3C H3CA 110.2 . . ? N1C C4C C5C 118.8(2) . . ? N1C C4C C8C 122.7(2) . . ? C5C C4C C8C 107.0(2) . . ? N1C C4C C9C 119.4(2) . . ? C5C C4C C9C 115.8(2) . . ? C8C C4C C9C 58.71(18) . . ? O3C C5C C4C 125.9(2) . . ? O3C C5C C6C 126.2(2) . . ? C4C C5C C6C 107.8(2) . . ? C5C C6C C7C 105.5(2) . . ? C5C C6C H6CA 110.6 . . ? C7C C6C H6CA 110.6 . . ? C5C C6C H6CB 110.6 . . ? C7C C6C H6CB 110.6 . . ? H6CA C6C H6CB 108.8 . . ? C6C C7C C8C 104.6(2) . . ? C6C C7C H7CA 110.8 . . ? C8C C7C H7CA 110.8 . . ? C6C C7C H7CB 110.8 . . ? C8C C7C H7CB 110.8 . . ? H7CA C7C H7CB 108.9 . . ? C9C C8C C4C 61.00(17) . . ? C9C C8C C7C 117.9(2) . . ? C4C C8C C7C 108.4(2) . . ? C9C C8C H8CA 118.6 . . ? C4C C8C H8CA 118.6 . . ? C7C C8C H8CA 118.6 . . ? C8C C9C C4C 60.29(18) . . ? C8C C9C H9CA 117.7 . . ? C4C C9C H9CA 117.7 . . ? C8C C9C H9CB 117.7 . . ? C4C C9C H9CB 117.7 . . ? H9CA C9C H9CB 114.9 . . ? C11C C10C C3C 113.5(2) . . ? C11C C10C H10E 108.9 . . ? C3C C10C H10E 108.9 . . ? C11C C10C H10F 108.9 . . ? C3C C10C H10F 108.9 . . ? H10E C10C H10F 107.7 . . ? C12C C11C C16C 117.7(3) . . ? C12C C11C C10C 120.1(3) . . ? C16C C11C C10C 122.2(3) . . ? C13C C12C C11C 121.2(3) . . ? C13C C12C H12C 119.4 . . ? C11C C12C H12C 119.4 . . ? C14C C13C C12C 120.4(3) . . ? C14C C13C H13C 119.8 . . ? C12C C13C H13C 119.8 . . ? C15C C14C C13C 119.5(3) . . ? C15C C14C H14C 120.2 . . ? C13C C14C H14C 120.2 . . ? C14C C15C C16C 120.4(3) . . ? C14C C15C H15C 119.8 . . ? C16C C15C H15C 119.8 . . ? C15C C16C C11C 120.8(3) . . ? C15C C16C H16C 119.6 . . ? C11C C16C H16C 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4A N1A C1A O1A -7.7(4) . . . . ? C3A N1A C1A O1A -166.9(3) . . . . ? C4A N1A C1A O2A 171.3(2) . . . . ? C3A N1A C1A O2A 12.1(3) . . . . ? C2A O2A C1A O1A -171.7(2) . . . . ? C2A O2A C1A N1A 9.2(3) . . . . ? C1A O2A C2A C3A -25.8(3) . . . . ? C1A N1A C3A C2A -26.3(3) . . . . ? C4A N1A C3A C2A 176.0(2) . . . . ? C1A N1A C3A C10A 92.3(3) . . . . ? C4A N1A C3A C10A -65.4(3) . . . . ? O2A C2A C3A N1A 30.0(2) . . . . ? O2A C2A C3A C10A -87.3(3) . . . . ? C1A N1A C4A C5A -58.5(3) . . . . ? C3A N1A C4A C5A 97.4(3) . . . . ? C1A N1A C4A C9A 148.8(2) . . . . ? C3A N1A C4A C9A -55.2(3) . . . . ? C1A N1A C4A C8A 80.0(3) . . . . ? C3A N1A C4A C8A -124.1(3) . . . . ? N1A C4A C5A O3A -19.0(4) . . . . ? C9A C4A C5A O3A 134.6(3) . . . . ? C8A C4A C5A O3A -163.8(3) . . . . ? N1A C4A C5A C6A 158.7(2) . . . . ? C9A C4A C5A C6A -47.6(3) . . . . ? C8A C4A C5A C6A 13.9(3) . . . . ? O3A C5A C6A C7A 153.5(3) . . . . ? C4A C5A C6A C7A -24.2(3) . . . . ? C5A C6A C7A C8A 24.6(3) . . . . ? C6A C7A C8A C9A 49.6(3) . . . . ? C6A C7A C8A C4A -16.7(3) . . . . ? N1A C4A C8A C9A 106.2(3) . . . . ? C5A C4A C8A C9A -110.4(2) . . . . ? N1A C4A C8A C7A -141.3(3) . . . . ? C5A C4A C8A C7A 2.1(3) . . . . ? C9A C4A C8A C7A 112.5(3) . . . . ? C7A C8A C9A C4A -96.7(3) . . . . ? N1A C4A C9A C8A -112.9(2) . . . . ? C5A C4A C9A C8A 93.3(2) . . . . ? N1A C3A C10A C11A 177.6(2) . . . . ? C2A C3A C10A C11A -73.4(3) . . . . ? C3A C10A C11A C12A 95.6(3) . . . . ? C3A C10A C11A C16A -84.7(3) . . . . ? C16A C11A C12A C13A 0.1(4) . . . . ? C10A C11A C12A C13A 179.8(3) . . . . ? C11A C12A C13A C14A -0.8(4) . . . . ? C12A C13A C14A C15A 0.1(4) . . . . ? C13A C14A C15A C16A 1.2(4) . . . . ? C14A C15A C16A C11A -1.9(4) . . . . ? C12A C11A C16A C15A 1.3(4) . . . . ? C10A C11A C16A C15A -178.4(2) . . . . ? C4B N1B C1B O1B -8.4(4) . . . . ? C3B N1B C1B O1B -168.0(3) . . . . ? C4B N1B C1B O2B 172.0(2) . . . . ? C3B N1B C1B O2B 12.4(3) . . . . ? C2B O2B C1B O1B -171.5(3) . . . . ? C2B O2B C1B N1B 8.1(3) . . . . ? C1B O2B C2B C3B -24.2(3) . . . . ? C1B N1B C3B C2B -25.8(3) . . . . ? C4B N1B C3B C2B 175.9(3) . . . . ? C1B N1B C3B C10B 94.7(3) . . . . ? C4B N1B C3B C10B -63.6(3) . . . . ? O2B C2B C3B N1B 28.7(3) . . . . ? O2B C2B C3B C10B -90.0(3) . . . . ? C1B N1B C4B C5B -59.1(3) . . . . ? C3B N1B C4B C5B 97.4(3) . . . . ? C1B N1B C4B C9B 146.8(2) . . . . ? C3B N1B C4B C9B -56.6(3) . . . . ? C1B N1B C4B C8B 78.3(3) . . . . ? C3B N1B C4B C8B -125.2(3) . . . . ? N1B C4B C5B O3B -22.8(4) . . . . ? C9B C4B C5B O3B 132.1(3) . . . . ? C8B C4B C5B O3B -165.7(3) . . . . ? N1B C4B C5B C6B 155.2(2) . . . . ? C9B C4B C5B C6B -49.9(3) . . . . ? C8B C4B C5B C6B 12.3(3) . . . . ? O3B C5B C6B C7B 156.3(3) . . . . ? C4B C5B C6B C7B -21.6(3) . . . . ? C5B C6B C7B C8B 22.3(3) . . . . ? C6B C7B C8B C9B 50.4(3) . . . . ? C6B C7B C8B C4B -15.2(3) . . . . ? N1B C4B C8B C9B 106.9(3) . . . . ? C5B C4B C8B C9B -110.3(2) . . . . ? N1B C4B C8B C7B -140.7(3) . . . . ? C5B C4B C8B C7B 2.1(3) . . . . ? C9B C4B C8B C7B 112.4(3) . . . . ? C7B C8B C9B C4B -96.2(3) . . . . ? N1B C4B C9B C8B -110.7(2) . . . . ? C5B C4B C9B C8B 93.9(2) . . . . ? N1B C3B C10B C11B 179.6(2) . . . . ? C2B C3B C10B C11B -69.6(3) . . . . ? C3B C10B C11B C16B -88.6(3) . . . . ? C3B C10B C11B C12B 91.3(3) . . . . ? C16B C11B C12B C13B 0.2(4) . . . . ? C10B C11B C12B C13B -179.7(3) . . . . ? C11B C12B C13B C14B 0.1(5) . . . . ? C12B C13B C14B C15B -1.3(5) . . . . ? C13B C14B C15B C16B 2.2(5) . . . . ? C14B C15B C16B C11B -1.9(4) . . . . ? C12B C11B C16B C15B 0.8(4) . . . . ? C10B C11B C16B C15B -179.4(3) . . . . ? C4C N1C C1C O1C -7.2(4) . . . . ? C3C N1C C1C O1C -173.7(3) . . . . ? C4C N1C C1C O2C 173.1(2) . . . . ? C3C N1C C1C O2C 6.5(3) . . . . ? C2C O2C C1C O1C -178.1(3) . . . . ? C2C O2C C1C N1C 1.6(3) . . . . ? C1C O2C C2C C3C -8.6(3) . . . . ? C1C N1C C3C C10C 109.7(3) . . . . ? C4C N1C C3C C10C -55.8(3) . . . . ? C1C N1C C3C C2C -11.0(3) . . . . ? C4C N1C C3C C2C -176.5(2) . . . . ? O2C C2C C3C N1C 11.3(3) . . . . ? O2C C2C C3C C10C -108.9(3) . . . . ? C1C N1C C4C C5C -68.9(3) . . . . ? C3C N1C C4C C5C 95.7(3) . . . . ? C1C N1C C4C C8C 69.6(3) . . . . ? C3C N1C C4C C8C -125.7(3) . . . . ? C1C N1C C4C C9C 139.4(3) . . . . ? C3C N1C C4C C9C -56.0(3) . . . . ? N1C C4C C5C O3C -18.7(4) . . . . ? C8C C4C C5C O3C -163.1(3) . . . . ? C9C C4C C5C O3C 134.0(3) . . . . ? N1C C4C C5C C6C 158.5(2) . . . . ? C8C C4C C5C C6C 14.2(3) . . . . ? C9C C4C C5C C6C -48.7(3) . . . . ? O3C C5C C6C C7C 152.4(3) . . . . ? C4C C5C C6C C7C -24.8(3) . . . . ? C5C C6C C7C C8C 25.3(3) . . . . ? N1C C4C C8C C9C 107.0(3) . . . . ? C5C C4C C8C C9C -110.3(2) . . . . ? N1C C4C C8C C7C -140.6(3) . . . . ? C5C C4C C8C C7C 2.0(3) . . . . ? C9C C4C C8C C7C 112.3(3) . . . . ? C6C C7C C8C C9C 49.2(3) . . . . ? C6C C7C C8C C4C -17.0(3) . . . . ? C7C C8C C9C C4C -96.5(3) . . . . ? N1C C4C C9C C8C -112.5(2) . . . . ? C5C C4C C9C C8C 94.9(2) . . . . ? N1C C3C C10C C11C -168.4(2) . . . . ? C2C C3C C10C C11C -55.9(4) . . . . ? C3C C10C C11C C12C 130.0(3) . . . . ? C3C C10C C11C C16C -51.0(4) . . . . ? C16C C11C C12C C13C 0.2(4) . . . . ? C10C C11C C12C C13C 179.2(2) . . . . ? C11C C12C C13C C14C 0.6(4) . . . . ? C12C C13C C14C C15C -0.1(4) . . . . ? C13C C14C C15C C16C -1.2(4) . . . . ? C14C C15C C16C C11C 2.0(4) . . . . ? C12C C11C C16C C15C -1.4(4) . . . . ? C10C C11C C16C C15C 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.170 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.041 # Attachment '20-major_cmc0772a.cif' data_cmc0772a _database_code_depnum_ccdc_archive 'CCDC 763761' #TrackingRef '20-major_cmc0772a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CMC0772a _chemical_melting_point ? _chemical_formula_moiety 'C21 H19 N O3' _chemical_formula_sum 'C21 H19 N O3' _chemical_formula_weight 333.37 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0020 0.0020 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.959(2) _cell_length_b 6.0746(12) _cell_length_c 12.943(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.432(3) _cell_angle_gamma 90.00 _cell_volume 841.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3390 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 13.21 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.009 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9993 _exptl_absorpt_correction_T_max 0.9999 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details 'Z. F. Al-Rashid / Prof. R. Hsung' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.41328 _diffrn_radiation_type ? _diffrn_radiation_source 'APS 15-ID-B' _diffrn_radiation_monochromator Double-diamond _diffrn_measurement_device_type 'Bruker-AXS APEX-II' _diffrn_measurement_method 'Phi-scans fixed Chi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14159 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 14.96 _reflns_number_total 1715 _reflns_number_gt 1401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.2619P] 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(3) _refine_ls_number_reflns 1715 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.40781(19) 0.5584(4) 0.45930(15) 0.0257(5) Uani 1 1 d . . . O2 O 0.42844(18) 0.3352(4) 0.32316(15) 0.0228(5) Uani 1 1 d . . . O3 O 0.1072(2) 0.5487(5) 0.44828(16) 0.0305(6) Uani 1 1 d . . . N1 N 0.3020(2) 0.2254(5) 0.42671(17) 0.0188(6) Uani 1 1 d . . . C1 C 0.3807(3) 0.3888(6) 0.4094(2) 0.0202(7) Uani 1 1 d . . . C2 C 0.4018(3) 0.1029(6) 0.2978(2) 0.0216(8) Uani 1 1 d . . . H2A H 0.4734 0.0123 0.3365 0.026 Uiso 1 1 calc R . . C3 C 0.2842(2) 0.0529(6) 0.3447(2) 0.0188(6) Uani 1 1 d . . . H3A H 0.2928 -0.0957 0.3788 0.023 Uiso 1 1 calc R . . C4 C 0.3857(2) 0.0618(6) 0.1809(2) 0.0196(7) Uani 1 1 d . . . C5 C 0.3353(3) 0.2242(6) 0.1061(2) 0.0215(7) Uani 1 1 d . . . H5A H 0.3169 0.3669 0.1286 0.026 Uiso 1 1 calc R . . C6 C 0.3128(3) 0.1731(6) -0.0017(2) 0.0238(8) Uani 1 1 d . . . H6A H 0.2780 0.2819 -0.0522 0.029 Uiso 1 1 calc R . . C7 C 0.3404(3) -0.0337(7) -0.0364(2) 0.0236(8) Uani 1 1 d . . . H7A H 0.3246 -0.0656 -0.1099 0.028 Uiso 1 1 calc R . . C8 C 0.3914(3) -0.1945(6) 0.0375(2) 0.0247(8) Uani 1 1 d . . . H8A H 0.4107 -0.3361 0.0143 0.030 Uiso 1 1 calc R . . C9 C 0.4141(3) -0.1465(6) 0.1461(2) 0.0218(7) Uani 1 1 d . . . H9A H 0.4489 -0.2559 0.1963 0.026 Uiso 1 1 calc R . . C10 C 0.1605(2) 0.0675(6) 0.2645(2) 0.0179(6) Uani 1 1 d . . . C11 C 0.0924(3) 0.2622(6) 0.2448(2) 0.0222(8) Uani 1 1 d . . . H11A H 0.1201 0.3897 0.2856 0.027 Uiso 1 1 calc R . . C12 C -0.0167(3) 0.2718(6) 0.1653(2) 0.0246(8) Uani 1 1 d . . . H12A H -0.0630 0.4050 0.1528 0.029 Uiso 1 1 calc R . . C13 C -0.0574(3) 0.0850(7) 0.1042(2) 0.0269(8) Uani 1 1 d . . . H13A H -0.1303 0.0921 0.0491 0.032 Uiso 1 1 calc R . . C14 C 0.0089(3) -0.1106(6) 0.1242(2) 0.0261(8) Uani 1 1 d . . . H14A H -0.0191 -0.2378 0.0832 0.031 Uiso 1 1 calc R . . C15 C 0.1168(3) -0.1205(6) 0.2046(2) 0.0222(7) Uani 1 1 d . . . H15A H 0.1610 -0.2554 0.2188 0.027 Uiso 1 1 calc R . . C16 C 0.2387(3) 0.2367(6) 0.5132(2) 0.0205(7) Uani 1 1 d . . . C17 C 0.1500(3) 0.4213(6) 0.5198(2) 0.0221(7) Uani 1 1 d . . . C18 C 0.1302(3) 0.4357(7) 0.6320(2) 0.0277(8) Uani 1 1 d . . . H18A H 0.0559 0.3497 0.6397 0.033 Uiso 1 1 calc R . . H18B H 0.1190 0.5905 0.6519 0.033 Uiso 1 1 calc R . . C19 C 0.2505(3) 0.3372(7) 0.7008(2) 0.0300(8) Uani 1 1 d . . . H19A H 0.3112 0.4551 0.7285 0.036 Uiso 1 1 calc R . . H19B H 0.2313 0.2546 0.7613 0.036 Uiso 1 1 calc R . . C20 C 0.3035(3) 0.1832(6) 0.6280(2) 0.0254(8) Uani 1 1 d . . . H20A H 0.3949 0.1490 0.6448 0.031 Uiso 1 1 calc R . . C21 C 0.2147(3) 0.0207(7) 0.5667(2) 0.0288(8) Uani 1 1 d . . . H21A H 0.1327 0.0024 0.5860 0.035 Uiso 1 1 calc R . . H21B H 0.2500 -0.1159 0.5434 0.035 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 0.0333(11) 0.0183(17) 0.0237(11) -0.0042(10) 0.0024(8) -0.0038(10) O2 0.0299(11) 0.0172(16) 0.0218(10) -0.0004(9) 0.0065(9) -0.0048(10) O3 0.0431(13) 0.0173(16) 0.0285(11) 0.0009(10) 0.0018(9) 0.0108(11) N1 0.0243(12) 0.0154(18) 0.0169(12) -0.0013(11) 0.0046(9) -0.0019(11) C1 0.0270(15) 0.014(2) 0.0185(14) 0.0010(13) 0.0014(12) 0.0041(13) C2 0.0251(15) 0.019(2) 0.0188(14) -0.0020(13) 0.0008(11) 0.0007(13) C3 0.0253(14) 0.0108(19) 0.0194(14) -0.0006(13) 0.0031(11) -0.0009(13) C4 0.0195(14) 0.018(2) 0.0218(14) 0.0009(14) 0.0045(11) -0.0012(14) C5 0.0275(15) 0.014(2) 0.0231(14) -0.0006(13) 0.0059(12) -0.0005(13) C6 0.0263(15) 0.025(2) 0.0190(14) 0.0041(13) 0.0024(12) 0.0020(14) C7 0.0256(16) 0.025(2) 0.0201(15) -0.0028(13) 0.0056(12) -0.0027(13) C8 0.0236(14) 0.023(2) 0.0277(15) -0.0049(13) 0.0061(12) -0.0012(13) C9 0.0243(15) 0.015(2) 0.0254(15) 0.0033(14) 0.0043(12) 0.0030(13) C10 0.0240(14) 0.012(2) 0.0189(14) -0.0003(12) 0.0075(11) -0.0041(13) C11 0.0295(16) 0.014(2) 0.0217(15) -0.0002(13) 0.0026(12) -0.0030(13) C12 0.0282(16) 0.018(2) 0.0266(16) 0.0039(13) 0.0033(12) -0.0006(13) C13 0.0286(16) 0.026(3) 0.0241(15) 0.0041(14) 0.0015(12) -0.0066(15) C14 0.0291(16) 0.026(3) 0.0238(15) -0.0029(14) 0.0070(13) -0.0099(15) C15 0.0305(15) 0.013(2) 0.0249(15) 0.0003(13) 0.0092(12) -0.0027(13) C16 0.0243(14) 0.019(2) 0.0173(14) 0.0002(13) 0.0038(11) -0.0009(13) C17 0.0236(15) 0.017(2) 0.0239(15) -0.0045(14) 0.0023(12) -0.0013(13) C18 0.0317(16) 0.026(2) 0.0262(16) -0.0023(15) 0.0086(13) 0.0009(15) C19 0.0344(17) 0.033(3) 0.0226(15) -0.0051(15) 0.0049(13) 0.0006(16) C20 0.0343(16) 0.024(2) 0.0166(13) 0.0026(13) 0.0034(12) 0.0050(14) C21 0.0412(18) 0.018(3) 0.0290(17) 0.0032(14) 0.0120(14) -0.0009(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 1.219(4) . ? O2 C1 1.370(3) . ? O2 C2 1.464(4) . ? O3 C17 1.220(4) . ? N1 C1 1.365(4) . ? N1 C16 1.440(3) . ? N1 C3 1.474(4) . ? C2 C4 1.506(4) . ? C2 C3 1.569(4) . ? C2 H2A 1.0000 . ? C3 C10 1.522(4) . ? C3 H3A 1.0000 . ? C4 C9 1.400(5) . ? C4 C5 1.409(5) . ? C5 C6 1.399(4) . ? C5 H5A 0.9500 . ? C6 C7 1.388(5) . ? C6 H6A 0.9500 . ? C7 C8 1.396(5) . ? C7 H7A 0.9500 . ? C8 C9 1.405(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.393(5) . ? C10 C15 1.405(5) . ? C11 C12 1.400(4) . ? C11 H11A 0.9500 . ? C12 C13 1.401(5) . ? C12 H12A 0.9500 . ? C13 C14 1.387(6) . ? C13 H13A 0.9500 . ? C14 C15 1.399(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.499(5) . ? C16 C21 1.532(5) . ? C16 C20 1.536(4) . ? C17 C18 1.516(4) . ? C18 C19 1.544(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.529(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.489(5) . ? C20 H20A 1.0000 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 108.6(2) . . ? C1 N1 C16 121.4(3) . . ? C1 N1 C3 112.9(2) . . ? C16 N1 C3 125.6(3) . . ? O1 C1 N1 128.2(3) . . ? O1 C1 O2 122.7(3) . . ? N1 C1 O2 109.1(3) . . ? O2 C2 C4 111.1(3) . . ? O2 C2 C3 103.9(2) . . ? C4 C2 C3 115.3(2) . . ? O2 C2 H2A 108.8 . . ? C4 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? N1 C3 C10 114.2(3) . . ? N1 C3 C2 98.6(2) . . ? C10 C3 C2 114.2(2) . . ? N1 C3 H3A 109.8 . . ? C10 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C9 C4 C5 119.6(3) . . ? C9 C4 C2 119.1(3) . . ? C5 C4 C2 121.2(3) . . ? C6 C5 C4 119.2(3) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C7 C6 C5 121.3(3) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C4 C9 C8 120.4(3) . . ? C4 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C11 C10 C15 118.9(3) . . ? C11 C10 C3 122.6(3) . . ? C15 C10 C3 118.5(3) . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 C10 120.6(3) . . ? C14 C15 H15A 119.7 . . ? C10 C15 H15A 119.7 . . ? N1 C16 C17 120.4(3) . . ? N1 C16 C21 118.0(3) . . ? C17 C16 C21 116.0(3) . . ? N1 C16 C20 122.8(2) . . ? C17 C16 C20 105.9(3) . . ? C21 C16 C20 58.1(2) . . ? O3 C17 C16 125.4(3) . . ? O3 C17 C18 125.4(3) . . ? C16 C17 C18 109.0(3) . . ? C17 C18 C19 104.5(3) . . ? C17 C18 H18A 110.9 . . ? C19 C18 H18A 110.9 . . ? C17 C18 H18B 110.9 . . ? C19 C18 H18B 110.9 . . ? H18A C18 H18B 108.9 . . ? C20 C19 C18 105.7(2) . . ? C20 C19 H19A 110.6 . . ? C18 C19 H19A 110.6 . . ? C20 C19 H19B 110.6 . . ? C18 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? C21 C20 C19 116.3(3) . . ? C21 C20 C16 60.8(2) . . ? C19 C20 C16 108.0(3) . . ? C21 C20 H20A 119.2 . . ? C19 C20 H20A 119.2 . . ? C16 C20 H20A 119.2 . . ? C20 C21 C16 61.1(2) . . ? C20 C21 H21A 117.7 . . ? C16 C21 H21A 117.7 . . ? C20 C21 H21B 117.7 . . ? C16 C21 H21B 117.7 . . ? H21A C21 H21B 114.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C1 O1 -0.6(5) . . . . ? C3 N1 C1 O1 175.4(3) . . . . ? C16 N1 C1 O2 179.5(2) . . . . ? C3 N1 C1 O2 -4.5(3) . . . . ? C2 O2 C1 O1 166.6(3) . . . . ? C2 O2 C1 N1 -13.5(3) . . . . ? C1 O2 C2 C4 149.3(2) . . . . ? C1 O2 C2 C3 24.6(3) . . . . ? C1 N1 C3 C10 -102.9(3) . . . . ? C16 N1 C3 C10 72.9(4) . . . . ? C1 N1 C3 C2 18.6(3) . . . . ? C16 N1 C3 C2 -165.6(3) . . . . ? O2 C2 C3 N1 -24.8(3) . . . . ? C4 C2 C3 N1 -146.6(3) . . . . ? O2 C2 C3 C10 96.7(3) . . . . ? C4 C2 C3 C10 -25.1(4) . . . . ? O2 C2 C4 C9 152.2(2) . . . . ? C3 C2 C4 C9 -89.9(3) . . . . ? O2 C2 C4 C5 -31.8(4) . . . . ? C3 C2 C4 C5 86.1(4) . . . . ? C9 C4 C5 C6 1.0(4) . . . . ? C2 C4 C5 C6 -175.0(3) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C5 C4 C9 C8 -0.7(4) . . . . ? C2 C4 C9 C8 175.4(3) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? N1 C3 C10 C11 22.7(4) . . . . ? C2 C3 C10 C11 -89.7(3) . . . . ? N1 C3 C10 C15 -160.6(3) . . . . ? C2 C3 C10 C15 87.0(3) . . . . ? C15 C10 C11 C12 -1.1(4) . . . . ? C3 C10 C11 C12 175.7(3) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? C11 C12 C13 C14 1.5(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C13 C14 C15 C10 -1.2(4) . . . . ? C11 C10 C15 C14 2.0(4) . . . . ? C3 C10 C15 C14 -174.9(2) . . . . ? C1 N1 C16 C17 60.9(4) . . . . ? C3 N1 C16 C17 -114.5(3) . . . . ? C1 N1 C16 C21 -146.5(3) . . . . ? C3 N1 C16 C21 38.0(4) . . . . ? C1 N1 C16 C20 -78.2(4) . . . . ? C3 N1 C16 C20 106.3(4) . . . . ? N1 C16 C17 O3 13.6(5) . . . . ? C21 C16 C17 O3 -139.4(3) . . . . ? C20 C16 C17 O3 158.8(3) . . . . ? N1 C16 C17 C18 -161.9(3) . . . . ? C21 C16 C17 C18 45.1(4) . . . . ? C20 C16 C17 C18 -16.7(4) . . . . ? O3 C17 C18 C19 -149.4(4) . . . . ? C16 C17 C18 C19 26.1(4) . . . . ? C17 C18 C19 C20 -24.9(4) . . . . ? C18 C19 C20 C21 -50.4(4) . . . . ? C18 C19 C20 C16 15.3(4) . . . . ? N1 C16 C20 C21 -104.8(4) . . . . ? C17 C16 C20 C21 111.1(3) . . . . ? N1 C16 C20 C19 144.6(3) . . . . ? C17 C16 C20 C19 0.5(4) . . . . ? C21 C16 C20 C19 -110.6(3) . . . . ? C19 C20 C21 C16 96.8(3) . . . . ? N1 C16 C21 C20 113.1(3) . . . . ? C17 C16 C21 C20 -93.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 14.96 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.167 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.045 # Attachment '30-Major_07221.cif' data_07221 _database_code_depnum_ccdc_archive 'CCDC 680317' #TrackingRef '30-Major_07221.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 07221 _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N O3' _chemical_formula_sum 'C16 H17 N O3' _chemical_formula_weight 271.31 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.2183(9) _cell_length_b 10.4772(9) _cell_length_c 12.5802(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1346.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2898 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.42 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9552 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15960 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1771 _reflns_number_gt 1673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.3511P] 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), 1298 Friedel Pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1771 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.30883(12) 0.60403(14) -0.09433(9) 0.0320(3) Uani 1 1 d . . . O2 O 0.46247(12) 0.46805(13) -0.03559(10) 0.0302(3) Uani 1 1 d . . . O3 O 0.14694(11) 0.48036(11) 0.09905(10) 0.0263(3) Uani 1 1 d . . . N1 N 0.37911(13) 0.60690(13) 0.08122(10) 0.0198(3) Uani 1 1 d . . . C1 C 0.37427(16) 0.56409(17) -0.02225(13) 0.0243(3) Uani 1 1 d . . . C2 C 0.53130(16) 0.44648(16) 0.06305(13) 0.0246(3) Uani 1 1 d . . . H2A H 0.6208 0.4825 0.0597 0.030 Uiso 1 1 calc R . . H2B H 0.5376 0.3540 0.0785 0.030 Uiso 1 1 calc R . . C3 C 0.44989(15) 0.51458(15) 0.14829(12) 0.0201(3) Uani 1 1 d . . . H3A H 0.3863 0.4531 0.1804 0.024 Uiso 1 1 calc R . . C4 C 0.53018(14) 0.57597(15) 0.23526(12) 0.0184(3) Uani 1 1 d . . . C5 C 0.63152(15) 0.66096(15) 0.21114(12) 0.0206(3) Uani 1 1 d . . . H5A H 0.6498 0.6814 0.1391 0.025 Uiso 1 1 calc R . . C6 C 0.70568(16) 0.71574(16) 0.29155(13) 0.0224(3) Uani 1 1 d . . . H6A H 0.7744 0.7733 0.2745 0.027 Uiso 1 1 calc R . . C7 C 0.67903(17) 0.68609(16) 0.39721(13) 0.0249(3) Uani 1 1 d . . . H7A H 0.7307 0.7222 0.4523 0.030 Uiso 1 1 calc R . . C8 C 0.57730(17) 0.60414(16) 0.42208(13) 0.0257(4) Uani 1 1 d . . . H8A H 0.5583 0.5855 0.4943 0.031 Uiso 1 1 calc R . . C9 C 0.50271(16) 0.54885(14) 0.34174(12) 0.0215(3) Uani 1 1 d . . . H9A H 0.4331 0.4926 0.3593 0.026 Uiso 1 1 calc R . . C10 C 0.26602(15) 0.66970(15) 0.12401(12) 0.0185(3) Uani 1 1 d . . . C11 C 0.24363(18) 0.80838(15) 0.09135(14) 0.0264(4) Uani 1 1 d . . . H11A H 0.3077 0.8477 0.0422 0.032 Uiso 1 1 calc R . . H11B H 0.1521 0.8372 0.0816 0.032 Uiso 1 1 calc R . . C12 C 0.28809(17) 0.77909(15) 0.20177(13) 0.0237(3) Uani 1 1 d . . . H12A H 0.3817 0.7997 0.2175 0.028 Uiso 1 1 calc R . . C13 C 0.19550(17) 0.78918(18) 0.29490(14) 0.0284(4) Uani 1 1 d . . . H13A H 0.2006 0.8764 0.3249 0.034 Uiso 1 1 calc R . . H13B H 0.2233 0.7285 0.3509 0.034 Uiso 1 1 calc R . . C14 C 0.05412(17) 0.76068(18) 0.26388(14) 0.0280(4) Uani 1 1 d . . . H14A H -0.0014 0.7631 0.3284 0.034 Uiso 1 1 calc R . . H14B H 0.0227 0.8279 0.2148 0.034 Uiso 1 1 calc R . . C15 C 0.03936(16) 0.63087(17) 0.21039(14) 0.0280(4) Uani 1 1 d . . . H15A H 0.0268 0.5662 0.2668 0.034 Uiso 1 1 calc R . . H15B H -0.0418 0.6326 0.1675 0.034 Uiso 1 1 calc R . . C16 C 0.14933(15) 0.58585(15) 0.13938(12) 0.0197(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 O1 0.0296(6) 0.0457(7) 0.0206(5) 0.0028(6) -0.0023(5) 0.0027(6) O2 0.0292(6) 0.0376(7) 0.0240(6) -0.0075(5) -0.0027(5) 0.0062(6) O3 0.0246(6) 0.0235(6) 0.0307(6) -0.0046(5) -0.0023(5) -0.0043(5) N1 0.0177(6) 0.0218(6) 0.0199(6) 0.0023(5) -0.0011(5) 0.0000(5) C1 0.0210(7) 0.0291(8) 0.0227(7) 0.0005(7) 0.0023(6) -0.0024(7) C2 0.0230(8) 0.0253(8) 0.0255(8) -0.0034(6) -0.0039(6) 0.0014(7) C3 0.0178(7) 0.0192(7) 0.0235(7) 0.0024(6) -0.0006(6) -0.0015(6) C4 0.0166(7) 0.0185(7) 0.0201(7) 0.0009(6) -0.0004(6) 0.0033(6) C5 0.0181(7) 0.0235(7) 0.0203(7) 0.0016(6) 0.0017(6) 0.0004(6) C6 0.0167(7) 0.0230(8) 0.0274(8) -0.0020(7) 0.0009(6) 0.0008(6) C7 0.0256(8) 0.0258(8) 0.0234(8) -0.0037(6) -0.0051(7) 0.0037(7) C8 0.0319(8) 0.0261(8) 0.0192(7) 0.0013(6) 0.0024(7) 0.0048(7) C9 0.0207(7) 0.0197(7) 0.0240(8) 0.0037(6) 0.0033(6) 0.0012(6) C10 0.0174(7) 0.0190(7) 0.0192(7) 0.0007(6) -0.0007(6) 0.0001(6) C11 0.0280(8) 0.0192(7) 0.0319(8) 0.0053(7) -0.0016(7) -0.0008(7) C12 0.0210(7) 0.0199(7) 0.0302(8) -0.0036(7) -0.0039(7) -0.0002(6) C13 0.0251(8) 0.0318(9) 0.0283(8) -0.0110(7) -0.0041(7) 0.0019(7) C14 0.0223(8) 0.0338(9) 0.0279(8) -0.0054(7) -0.0018(7) 0.0044(7) C15 0.0223(8) 0.0336(9) 0.0283(8) -0.0047(7) 0.0043(7) -0.0051(7) C16 0.0187(7) 0.0228(7) 0.0176(6) 0.0029(6) -0.0044(6) -0.0011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.202(2) . ? O2 C1 1.361(2) . ? O2 C2 1.444(2) . ? O3 C16 1.2164(19) . ? N1 C1 1.378(2) . ? N1 C10 1.435(2) . ? N1 C3 1.473(2) . ? C2 C3 1.533(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(2) . ? C3 H3A 1.0000 . ? C4 C9 1.398(2) . ? C4 C5 1.399(2) . ? C5 C6 1.388(2) . ? C5 H5A 0.9500 . ? C6 C7 1.392(2) . ? C6 H6A 0.9500 . ? C7 C8 1.384(3) . ? C7 H7A 0.9500 . ? C8 C9 1.392(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C16 1.494(2) . ? C10 C12 1.524(2) . ? C10 C11 1.527(2) . ? C11 C12 1.493(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.510(2) . ? C12 H12A 1.0000 . ? C13 C14 1.526(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.525(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.511(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 109.40(12) . . ? C1 N1 C10 118.35(13) . . ? C1 N1 C3 110.18(13) . . ? C10 N1 C3 118.79(12) . . ? O1 C1 O2 122.19(15) . . ? O1 C1 N1 128.28(16) . . ? O2 C1 N1 109.48(14) . . ? O2 C2 C3 105.31(12) . . ? O2 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? O2 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? N1 C3 C4 113.69(13) . . ? N1 C3 C2 99.86(12) . . ? C4 C3 C2 114.20(13) . . ? N1 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C9 C4 C5 119.07(14) . . ? C9 C4 C3 119.88(14) . . ? C5 C4 C3 121.05(13) . . ? C6 C5 C4 120.61(15) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 119.79(16) . . ? C5 C6 H6A 120.1 . . ? C7 C6 H6A 120.1 . . ? C8 C7 C6 120.08(16) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C9 120.35(15) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C8 C9 C4 120.08(15) . . ? C8 C9 H9A 120.0 . . ? C4 C9 H9A 120.0 . . ? N1 C10 C16 114.95(13) . . ? N1 C10 C12 117.82(13) . . ? C16 C10 C12 118.52(13) . . ? N1 C10 C11 117.13(14) . . ? C16 C10 C11 118.34(14) . . ? C12 C10 C11 58.62(11) . . ? C12 C11 C10 60.57(10) . . ? C12 C11 H11A 117.7 . . ? C10 C11 H11A 117.7 . . ? C12 C11 H11B 117.7 . . ? C10 C11 H11B 117.7 . . ? H11A C11 H11B 114.8 . . ? C11 C12 C13 121.12(15) . . ? C11 C12 C10 60.81(10) . . ? C13 C12 C10 117.27(14) . . ? C11 C12 H12A 115.5 . . ? C13 C12 H12A 115.5 . . ? C10 C12 H12A 115.5 . . ? C12 C13 C14 112.40(14) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 112.40(15) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 117.76(14) . . ? C16 C15 H15A 107.9 . . ? C14 C15 H15A 107.9 . . ? C16 C15 H15B 107.9 . . ? C14 C15 H15B 107.9 . . ? H15A C15 H15B 107.2 . . ? O3 C16 C10 119.77(14) . . ? O3 C16 C15 121.02(14) . . ? C10 C16 C15 119.11(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O2 C1 O1 176.54(16) . . . . ? C2 O2 C1 N1 -0.90(18) . . . . ? C10 N1 C1 O1 26.4(3) . . . . ? C3 N1 C1 O1 167.76(17) . . . . ? C10 N1 C1 O2 -156.40(13) . . . . ? C3 N1 C1 O2 -15.00(18) . . . . ? C1 O2 C2 C3 15.40(17) . . . . ? C1 N1 C3 C4 144.93(14) . . . . ? C10 N1 C3 C4 -73.86(17) . . . . ? C1 N1 C3 C2 22.89(16) . . . . ? C10 N1 C3 C2 164.09(13) . . . . ? O2 C2 C3 N1 -22.31(15) . . . . ? O2 C2 C3 C4 -143.99(13) . . . . ? N1 C3 C4 C9 118.89(16) . . . . ? C2 C3 C4 C9 -127.40(16) . . . . ? N1 C3 C4 C5 -60.54(19) . . . . ? C2 C3 C4 C5 53.2(2) . . . . ? C9 C4 C5 C6 1.3(2) . . . . ? C3 C4 C5 C6 -179.27(15) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 -1.2(2) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C7 C8 C9 C4 -0.1(2) . . . . ? C5 C4 C9 C8 -1.2(2) . . . . ? C3 C4 C9 C8 179.33(15) . . . . ? C1 N1 C10 C16 68.05(18) . . . . ? C3 N1 C10 C16 -70.02(17) . . . . ? C1 N1 C10 C12 -144.70(14) . . . . ? C3 N1 C10 C12 77.23(18) . . . . ? C1 N1 C10 C11 -77.73(18) . . . . ? C3 N1 C10 C11 144.20(14) . . . . ? N1 C10 C11 C12 -107.56(15) . . . . ? C16 C10 C11 C12 107.84(15) . . . . ? C10 C11 C12 C13 -106.01(17) . . . . ? N1 C10 C12 C11 106.39(16) . . . . ? C16 C10 C12 C11 -107.54(16) . . . . ? N1 C10 C12 C13 -141.39(15) . . . . ? C16 C10 C12 C13 4.7(2) . . . . ? C11 C10 C12 C13 112.22(17) . . . . ? C11 C12 C13 C14 30.4(2) . . . . ? C10 C12 C13 C14 -40.4(2) . . . . ? C12 C13 C14 C15 55.2(2) . . . . ? C13 C14 C15 C16 -35.1(2) . . . . ? N1 C10 C16 O3 -13.1(2) . . . . ? C12 C10 C16 O3 -160.11(14) . . . . ? C11 C10 C16 O3 132.24(16) . . . . ? N1 C10 C16 C15 163.32(14) . . . . ? C12 C10 C16 C15 16.3(2) . . . . ? C11 C10 C16 C15 -51.3(2) . . . . ? C14 C15 C16 O3 175.92(15) . . . . ? C14 C15 C16 C10 -0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.234 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.035