#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/72/1507250.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507250 loop_ _publ_author_name 'Bode, Jeffrey W.' 'Hachisu, Yoshifumi' 'Matsuura, Tomoo' 'Suzuki, Keisuke' _publ_section_title ; Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. ; _journal_issue 4 _journal_name_full 'Organic letters' _journal_page_first 391 _journal_page_last 394 _journal_paper_doi 10.1021/ol027283f _journal_volume 5 _journal_year 2003 _chemical_formula_moiety 'C17 H17 N O5' _chemical_formula_sum 'C17 H17 N O5' _chemical_formula_weight 315.32 _chemical_name_systematic ? _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXL-97 and manual edit' _cell_angle_alpha 90.00 _cell_angle_beta 104.998(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.7495(16) _cell_length_b 15.552(3) _cell_length_c 8.5599(11) _cell_measurement_reflns_used 8741 _cell_measurement_temperature 223(2) _cell_measurement_theta_max 68.23 _cell_measurement_theta_min 4.82 _cell_volume 1510.9(4) _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'teXsan (Rigaku, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _diffrn_ambient_temperature 223(2) _diffrn_detector_area_resol_mean 10 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method 'Oscillation Photograph' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku ratating anode Ultrax18' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8741 _diffrn_reflns_theta_full 68.23 _diffrn_reflns_theta_max 68.23 _diffrn_reflns_theta_min 4.82 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.331 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_extinction_coef 0.0045(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 1379 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0451 _refine_ls_shift/su_max '> 0.001' _refine_ls_shift/su_mean '> 0.001' _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.5637P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.1145 _reflns_number_gt 1343 _reflns_number_total 1379 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol027283fsi20021115_100334.cif _cod_data_source_block shelxl _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 1507250 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' 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 O1 O 0.9702(3) 0.8737(2) 1.4008(4) 0.0790(9) Uani 1 1 d . H1 H 0.962(6) 0.936(4) 1.396(8) 0.119 Uiso 1 1 d . O2 O 0.8395(2) 1.09277(16) 1.2169(3) 0.0571(7) Uani 1 1 d . O3 O 0.5856(2) 0.94128(15) 0.8110(3) 0.0502(6) Uani 1 1 d . O4 O 0.4648(3) 1.08184(19) 0.5802(3) 0.0668(8) Uani 1 1 d . O5 O 0.3328(2) 1.05882(18) 0.7234(3) 0.0568(6) Uani 1 1 d . N1 N 0.8756(3) 1.0065(2) 1.2440(4) 0.0570(8) Uani 1 1 d . C1 C 0.8979(3) 0.8279(3) 1.2797(4) 0.0566(9) Uani 1 1 d . C2 C 0.9069(4) 0.7384(3) 1.2926(6) 0.0686(11) Uani 1 1 d . H2 H 0.9625 0.7134 1.3801 0.082 Uiso 1 1 calc R C3 C 0.8362(4) 0.6872(3) 1.1799(6) 0.0688(11) Uani 1 1 d . H3 H 0.8430 0.6272 1.1902 0.083 Uiso 1 1 calc R C4 C 0.7546(4) 0.7222(2) 1.0506(6) 0.0680(11) Uani 1 1 d . H4 H 0.7049 0.6863 0.9742 0.082 Uiso 1 1 calc R C5 C 0.7461(3) 0.8104(2) 1.0335(5) 0.0547(8) Uani 1 1 d . H5 H 0.6919 0.8339 0.9431 0.066 Uiso 1 1 calc R C6 C 0.8162(3) 0.8657(2) 1.1475(4) 0.0473(8) Uani 1 1 d . C7 C 0.8011(3) 0.9591(2) 1.1358(4) 0.0460(7) Uani 1 1 d . C8 C 0.7132(3) 1.0144(2) 1.0332(4) 0.0424(7) Uani 1 1 d . C9 C 0.7429(3) 1.0948(2) 1.0940(4) 0.0475(7) Uani 1 1 d . C10 C 0.6834(3) 1.1766(2) 1.0447(5) 0.0528(8) Uani 1 1 d . H10A H 0.7419 1.2210 1.0418 0.063 Uiso 1 1 calc R H10B H 0.6405 1.1940 1.1236 0.063 Uiso 1 1 calc R C11 C 0.5980(3) 1.1681(2) 0.8787(4) 0.0512(8) Uani 1 1 d . H11 H 0.6444 1.1653 0.7973 0.061 Uiso 1 1 calc R C12 C 0.5284(3) 1.0833(2) 0.8702(4) 0.0449(7) Uani 1 1 d . H12 H 0.4852 1.0843 0.9553 0.054 Uiso 1 1 calc R C13 C 0.6097(3) 1.0044(2) 0.8974(4) 0.0420(7) Uani 1 1 d . C14 C 0.5156(4) 1.2455(3) 0.8392(6) 0.0650(10) Uani 1 1 d . H14A H 0.4624 1.2382 0.7326 0.097 Uiso 1 1 calc R H14B H 0.5617 1.2974 0.8409 0.097 Uiso 1 1 calc R H14C H 0.4704 1.2500 0.9189 0.097 Uiso 1 1 calc R C15 C 0.4403(3) 1.0737(2) 0.7079(4) 0.0484(8) Uani 1 1 d . C16 C 0.2411(4) 1.0545(3) 0.5700(5) 0.0693(11) Uani 1 1 d . H16A H 0.2437 1.1060 0.5051 0.083 Uiso 1 1 calc R H16B H 0.2534 1.0040 0.5078 0.083 Uiso 1 1 calc R C17 C 0.1274(4) 1.0486(4) 0.6089(7) 0.0984(18) Uani 1 1 d . H17A H 0.0649 1.0451 0.5097 0.148 Uiso 1 1 calc R H17B H 0.1158 1.0991 0.6695 0.148 Uiso 1 1 calc R H17C H 0.1259 0.9975 0.6735 0.148 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 0.075(2) 0.0678(18) 0.0754(18) 0.0078(15) -0.0143(15) 0.0043(16) O2 0.0508(15) 0.0472(13) 0.0650(16) -0.0038(11) 0.0000(12) -0.0032(11) O3 0.0562(14) 0.0440(12) 0.0477(12) -0.0024(10) 0.0082(10) 0.0034(10) O4 0.0704(18) 0.0817(19) 0.0494(15) 0.0078(12) 0.0173(13) 0.0119(14) O5 0.0450(14) 0.0709(15) 0.0502(13) -0.0033(11) 0.0046(10) 0.0005(11) N1 0.0495(17) 0.0486(16) 0.0659(18) 0.0031(13) 0.0025(14) 0.0022(13) C1 0.051(2) 0.062(2) 0.0553(19) 0.0089(17) 0.0108(16) 0.0070(18) C2 0.067(3) 0.061(2) 0.077(3) 0.022(2) 0.016(2) 0.019(2) C3 0.074(3) 0.0469(19) 0.086(3) 0.0095(19) 0.022(2) 0.0074(19) C4 0.072(3) 0.048(2) 0.081(3) 0.0003(18) 0.012(2) 0.0057(19) C5 0.053(2) 0.0501(18) 0.059(2) 0.0043(16) 0.0110(16) 0.0083(16) C6 0.0434(19) 0.0471(17) 0.0540(18) 0.0067(14) 0.0171(15) 0.0060(14) C7 0.0418(17) 0.0470(17) 0.0503(17) 0.0033(15) 0.0141(13) 0.0012(14) C8 0.0384(16) 0.0410(16) 0.0475(17) 0.0010(13) 0.0105(12) 0.0026(12) C9 0.0441(18) 0.0453(17) 0.0527(18) -0.0022(14) 0.0118(15) -0.0022(14) C10 0.052(2) 0.0403(17) 0.064(2) -0.0008(15) 0.0117(16) -0.0018(15) C11 0.052(2) 0.0430(18) 0.058(2) 0.0041(14) 0.0134(16) 0.0045(15) C12 0.0440(18) 0.0450(17) 0.0464(17) 0.0018(13) 0.0133(14) 0.0029(13) C13 0.0405(16) 0.0426(17) 0.0431(16) 0.0048(12) 0.0109(13) 0.0013(13) C14 0.064(2) 0.0460(18) 0.079(3) 0.0064(18) 0.008(2) 0.0128(18) C15 0.048(2) 0.0433(16) 0.052(2) 0.0048(13) 0.0091(15) 0.0091(14) C16 0.062(3) 0.072(3) 0.060(2) -0.0040(18) -0.0095(19) 0.005(2) C17 0.050(3) 0.140(5) 0.093(3) -0.007(3) -0.003(2) -0.012(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 H1 117(4) C9 O2 N1 108.1(2) C15 O5 C16 114.6(3) C7 N1 O2 107.4(3) O1 C1 C2 116.3(4) O1 C1 C6 123.7(3) C2 C1 C6 120.0(4) C3 C2 C1 120.5(4) C3 C2 H2 119.7 C1 C2 H2 119.7 C2 C3 C4 120.8(4) C2 C3 H3 119.6 C4 C3 H3 119.6 C3 C4 C5 119.6(4) C3 C4 H4 120.2 C5 C4 H4 120.2 C4 C5 C6 121.6(4) C4 C5 H5 119.2 C6 C5 H5 119.2 C5 C6 C1 117.4(3) C5 C6 C7 121.5(3) C1 C6 C7 121.0(3) N1 C7 C8 109.4(3) N1 C7 C6 117.3(3) C8 C7 C6 133.2(3) C9 C8 C7 103.9(3) C9 C8 C13 118.8(3) C7 C8 C13 137.4(3) O2 C9 C8 111.2(3) O2 C9 C10 119.6(3) C8 C9 C10 129.2(3) C9 C10 C11 110.2(3) C9 C10 H10A 109.6 C11 C10 H10A 109.6 C9 C10 H10B 109.6 C11 C10 H10B 109.6 H10A C10 H10B 108.1 C10 C11 C14 111.5(3) C10 C11 C12 109.4(3) C14 C11 C12 111.4(3) C10 C11 H11 108.1 C14 C11 H11 108.1 C12 C11 H11 108.1 C15 C12 C13 108.2(3) C15 C12 C11 110.9(3) C13 C12 C11 112.0(3) C15 C12 H12 108.6 C13 C12 H12 108.6 C11 C12 H12 108.6 O3 C13 C8 125.8(3) O3 C13 C12 121.0(3) C8 C13 C12 113.2(3) C11 C14 H14A 109.5 C11 C14 H14B 109.5 H14A C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 O4 C15 O5 124.5(3) O4 C15 C12 123.8(3) O5 C15 C12 111.7(3) C17 C16 O5 107.5(4) C17 C16 H16A 110.2 O5 C16 H16A 110.2 C17 C16 H16B 110.2 O5 C16 H16B 110.2 H16A C16 H16B 108.5 C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.360(5) O1 H1 0.97(6) O2 C9 1.334(4) O2 N1 1.408(4) O3 C13 1.217(4) O4 C15 1.207(5) O5 C15 1.324(5) O5 C16 1.469(5) N1 C7 1.322(5) C1 C2 1.398(6) C1 C6 1.409(5) C2 C3 1.356(7) C2 H2 0.9400 C3 C4 1.375(6) C3 H3 0.9400 C4 C5 1.380(6) C4 H4 0.9400 C5 C6 1.397(5) C5 H5 0.9400 C6 C7 1.465(5) C7 C8 1.452(5) C8 C9 1.364(5) C8 C13 1.457(5) C9 C10 1.460(5) C10 C11 1.519(5) C10 H10A 0.9800 C10 H10B 0.9800 C11 C14 1.526(5) C11 C12 1.543(5) C11 H11 0.9900 C12 C15 1.509(5) C12 C13 1.535(4) C12 H12 0.9900 C14 H14A 0.9700 C14 H14B 0.9700 C14 H14C 0.9700 C16 C17 1.461(7) C16 H16A 0.9800 C16 H16B 0.9800 C17 H17A 0.9700 C17 H17B 0.9700 C17 H17C 0.9700 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 N1 0.97(6) 1.80(7) 2.555(4) 132(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 C9 O2 N1 C7 0.8(4) O1 C1 C2 C3 178.2(4) C6 C1 C2 C3 -1.0(6) C1 C2 C3 C4 0.2(7) C2 C3 C4 C5 1.2(7) C3 C4 C5 C6 -1.9(7) C4 C5 C6 C1 1.1(5) C4 C5 C6 C7 -175.4(4) O1 C1 C6 C5 -178.9(4) C2 C1 C6 C5 0.3(5) O1 C1 C6 C7 -2.3(5) C2 C1 C6 C7 176.9(4) O2 N1 C7 C8 0.2(4) O2 N1 C7 C6 -175.8(3) C5 C6 C7 N1 -176.4(3) C1 C6 C7 N1 7.2(5) C5 C6 C7 C8 8.7(6) C1 C6 C7 C8 -167.7(3) N1 C7 C8 C9 -1.2(4) C6 C7 C8 C9 174.1(4) N1 C7 C8 C13 -179.2(3) C6 C7 C8 C13 -4.0(6) N1 O2 C9 C8 -1.6(4) N1 O2 C9 C10 177.3(3) C7 C8 C9 O2 1.7(4) C13 C8 C9 O2 -179.8(3) C7 C8 C9 C10 -177.0(4) C13 C8 C9 C10 1.5(5) O2 C9 C10 C11 164.8(3) C8 C9 C10 C11 -16.6(5) C9 C10 C11 C14 167.7(3) C9 C10 C11 C12 44.0(4) C10 C11 C12 C15 178.6(3) C14 C11 C12 C15 54.8(4) C10 C11 C12 C13 -60.5(4) C14 C11 C12 C13 175.8(3) C9 C8 C13 O3 164.6(3) C7 C8 C13 O3 -17.5(6) C9 C8 C13 C12 -15.7(4) C7 C8 C13 C12 162.1(4) C15 C12 C13 O3 -12.4(4) C11 C12 C13 O3 -135.0(3) C15 C12 C13 C8 167.9(3) C11 C12 C13 C8 45.3(4) C16 O5 C15 O4 -1.4(5) C16 O5 C15 C12 176.2(3) C13 C12 C15 O4 -72.5(4) C11 C12 C15 O4 50.7(5) C13 C12 C15 O5 110.0(3) C11 C12 C15 O5 -126.9(3) C15 O5 C16 C17 -173.1(4)