# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yoshimitsu Hashimoto' _publ_contact_author_email hashimoto.y.aj@m.titech.ac.jp loop_ _publ_author_name K.Suzuki Hi.Takikawa # Attachment '- isoxazoline_4.CIF' data_shelxl_4 _database_code_depnum_ccdc_archive 'CCDC 859931' #TrackingRef '- isoxazoline_4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H27 N O8' _chemical_formula_weight 433.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.549(4) _cell_length_b 8.811(4) _cell_length_c 14.226(6) _cell_angle_alpha 88.044(16) _cell_angle_beta 87.180(19) _cell_angle_gamma 85.651(18) _cell_volume 1066.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10501 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4848 _reflns_number_gt 4286 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4848 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.2317 _refine_ls_wR_factor_gt 0.2191 _refine_ls_goodness_of_fit_ref 1.990 _refine_ls_restrained_S_all 1.990 _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 0.00127(15) 0.46861(15) 0.35362(10) 0.0328(3) Uani 1 1 d . . . O2 O -0.04891(14) 0.38962(14) 0.20365(9) 0.0296(3) Uani 1 1 d . . . O3 O 0.20241(17) -0.07384(15) 0.20130(10) 0.0354(3) Uani 1 1 d . . . O4 O 0.30324(13) 0.32518(14) 0.32974(8) 0.0254(3) Uani 1 1 d . . . O5 O 0.71132(15) -0.11829(15) 0.36569(8) 0.0299(3) Uani 1 1 d . . . O6 O 0.53984(16) -0.26541(15) 0.29400(9) 0.0322(3) Uani 1 1 d . . . O7 O 0.50678(15) 0.25599(14) 0.04869(9) 0.0280(3) Uani 1 1 d . . . O8 O 0.89800(15) -0.15172(15) 0.01061(9) 0.0301(3) Uani 1 1 d . . . N1 N 0.44452(16) 0.24147(16) 0.29875(10) 0.0247(3) Uani 1 1 d . . . C1 C 0.03029(19) 0.35233(18) 0.28799(11) 0.0236(4) Uani 1 1 d . . . C2 C -0.0222(2) 0.2074(2) 0.33638(13) 0.0292(4) Uani 1 1 d . . . C3 C 0.0387(2) 0.0713(2) 0.30663(13) 0.0318(4) Uani 1 1 d . . . H1 H -0.0016 -0.0175 0.3354 0.038 Uiso 1 1 calc R . . C4 C 0.16336(19) 0.05099(18) 0.23258(12) 0.0244(4) Uani 1 1 d . . . C5 C 0.24825(18) 0.19076(17) 0.19798(10) 0.0203(3) Uani 1 1 d . . . H2 H 0.2405 0.2086 0.1285 0.024 Uiso 1 1 calc R . . C6 C 0.41874(18) 0.16970(17) 0.22513(11) 0.0206(3) Uani 1 1 d . . . C7 C 0.20095(18) 0.33563(17) 0.25130(11) 0.0210(3) Uani 1 1 d . . . H3 H 0.2243 0.4264 0.2103 0.025 Uiso 1 1 calc R . . C8 C 0.54626(18) 0.07901(17) 0.17422(11) 0.0211(3) Uani 1 1 d . . . C9 C 0.58850(19) 0.12700(18) 0.08115(11) 0.0219(4) Uani 1 1 d . . . C10 C 0.70761(19) 0.04857(19) 0.02895(11) 0.0242(4) Uani 1 1 d . . . H4 H 0.7348 0.0817 -0.0336 0.029 Uiso 1 1 calc R . . C11 C 0.78719(19) -0.07977(19) 0.06942(12) 0.0236(4) Uani 1 1 d . . . C12 C 0.74989(19) -0.12888(19) 0.16105(12) 0.0244(4) Uani 1 1 d . . . H5 H 0.8062 -0.2152 0.1883 0.029 Uiso 1 1 calc R . . C13 C 0.62841(18) -0.04968(18) 0.21268(11) 0.0218(4) Uani 1 1 d . . . C14 C 0.58210(19) -0.11590(18) 0.30791(11) 0.0228(4) Uani 1 1 d . . . H6 H 0.4908 -0.0532 0.3367 0.027 Uiso 1 1 calc R . . C15 C 0.6741(3) -0.1825(2) 0.45734(12) 0.0343(4) Uani 1 1 d . . . H7 H 0.5896 -0.1171 0.4891 0.041 Uiso 1 1 calc R . . H8 H 0.7677 -0.1862 0.4958 0.041 Uiso 1 1 calc R . . C16 C 0.6211(3) -0.3418(2) 0.45012(13) 0.0370(5) Uani 1 1 d . . . H9 H 0.7102 -0.4117 0.4277 0.044 Uiso 1 1 calc R . . H10 H 0.5827 -0.3797 0.5127 0.044 Uiso 1 1 calc R . . C17 C 0.4907(3) -0.3366(3) 0.38160(14) 0.0405(5) Uani 1 1 d . . . H11 H 0.4630 -0.4414 0.3706 0.049 Uiso 1 1 calc R . . H12 H 0.3963 -0.2788 0.4086 0.049 Uiso 1 1 calc R . . C18 C 0.0507(2) 0.6155(2) 0.32442(17) 0.0398(5) Uani 1 1 d . . . H13 H 0.1589 0.6237 0.3423 0.048 Uiso 1 1 calc R . . H14 H -0.0185 0.6948 0.3551 0.048 Uiso 1 1 calc R . . H15 H 0.0453 0.6285 0.2559 0.048 Uiso 1 1 calc R . . C19 C -0.2166(2) 0.3974(3) 0.21157(17) 0.0418(5) Uani 1 1 d . . . H16 H -0.2529 0.2968 0.2009 0.050 Uiso 1 1 calc R . . H17 H -0.2594 0.4709 0.1645 0.050 Uiso 1 1 calc R . . H18 H -0.2526 0.4298 0.2747 0.050 Uiso 1 1 calc R . . C20 C -0.1444(3) 0.2207(3) 0.41667(16) 0.0448(5) Uani 1 1 d . . . H19 H -0.0922 0.2254 0.4762 0.054 Uiso 1 1 calc R . . H20 H -0.2070 0.1319 0.4186 0.054 Uiso 1 1 calc R . . H21 H -0.2132 0.3136 0.4073 0.054 Uiso 1 1 calc R . . C21 C 0.5435(2) 0.3072(2) -0.04580(13) 0.0318(4) Uani 1 1 d . . . H22 H 0.6271 0.3774 -0.0458 0.038 Uiso 1 1 calc R . . H23 H 0.4498 0.3597 -0.0723 0.038 Uiso 1 1 calc R . . H24 H 0.5789 0.2195 -0.0840 0.038 Uiso 1 1 calc R . . C22 C 0.9786(2) -0.2874(2) 0.04458(15) 0.0370(4) Uani 1 1 d . . . H25 H 1.0728 -0.2624 0.0755 0.044 Uiso 1 1 calc R . . H26 H 1.0090 -0.3537 -0.0082 0.044 Uiso 1 1 calc R . . H27 H 0.9097 -0.3400 0.0899 0.044 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 0.0315(7) 0.0311(7) 0.0358(7) -0.0140(6) 0.0046(6) -0.0002(5) O2 0.0219(6) 0.0336(7) 0.0333(7) -0.0007(5) -0.0056(5) 0.0012(5) O3 0.0404(8) 0.0263(6) 0.0398(7) -0.0093(5) 0.0066(6) -0.0059(5) O4 0.0218(6) 0.0303(6) 0.0241(6) -0.0093(5) -0.0023(5) 0.0030(5) O5 0.0341(7) 0.0348(7) 0.0221(6) 0.0035(5) -0.0047(5) -0.0106(5) O6 0.0427(8) 0.0331(7) 0.0230(6) 0.0023(5) -0.0050(5) -0.0166(6) O7 0.0315(7) 0.0260(6) 0.0246(6) 0.0041(5) 0.0025(5) 0.0054(5) O8 0.0295(7) 0.0338(7) 0.0249(6) -0.0036(5) 0.0067(5) 0.0078(5) N1 0.0217(7) 0.0265(7) 0.0257(7) -0.0041(6) -0.0014(5) 0.0013(5) C1 0.0219(8) 0.0243(8) 0.0242(7) -0.0056(6) -0.0007(6) 0.0013(6) C2 0.0268(8) 0.0309(9) 0.0296(8) -0.0018(7) 0.0062(7) -0.0044(7) C3 0.0331(9) 0.0273(8) 0.0343(9) 0.0007(7) 0.0089(8) -0.0060(7) C4 0.0245(8) 0.0239(8) 0.0250(7) -0.0028(6) -0.0001(6) -0.0028(6) C5 0.0194(7) 0.0230(7) 0.0185(7) -0.0007(6) -0.0003(5) -0.0015(5) C6 0.0208(7) 0.0207(7) 0.0202(7) 0.0009(6) -0.0002(6) -0.0018(6) C7 0.0204(7) 0.0201(7) 0.0222(7) -0.0005(6) -0.0008(6) -0.0007(6) C8 0.0201(7) 0.0227(7) 0.0206(7) -0.0008(6) -0.0008(6) -0.0019(6) C9 0.0226(8) 0.0218(7) 0.0213(7) -0.0006(6) -0.0003(6) -0.0016(6) C10 0.0248(8) 0.0263(8) 0.0210(7) 0.0008(6) 0.0030(6) -0.0019(6) C11 0.0206(7) 0.0268(8) 0.0231(8) -0.0048(6) 0.0029(6) 0.0000(6) C12 0.0233(8) 0.0257(8) 0.0233(7) 0.0010(6) -0.0001(6) 0.0020(6) C13 0.0216(8) 0.0234(8) 0.0202(7) -0.0008(6) 0.0000(6) -0.0013(6) C14 0.0232(8) 0.0230(7) 0.0212(7) 0.0005(6) 0.0011(6) 0.0020(6) C15 0.0475(11) 0.0352(10) 0.0211(8) 0.0028(7) -0.0055(7) -0.0086(8) C16 0.0552(12) 0.0306(9) 0.0261(8) 0.0071(7) -0.0058(8) -0.0088(8) C17 0.0512(12) 0.0434(11) 0.0294(9) 0.0082(8) -0.0030(9) -0.0231(9) C18 0.0369(10) 0.0259(9) 0.0569(12) -0.0105(9) -0.0047(9) 0.0013(7) C19 0.0236(9) 0.0518(12) 0.0507(12) -0.0078(10) -0.0077(8) -0.0009(8) C20 0.0473(12) 0.0427(11) 0.0430(11) -0.0058(9) 0.0199(10) -0.0060(9) C21 0.0364(10) 0.0324(9) 0.0254(8) 0.0080(7) -0.0010(7) 0.0008(7) C22 0.0354(10) 0.0340(9) 0.0387(10) -0.0002(8) 0.0079(8) 0.0103(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4095(19) . ? O1 C18 1.434(2) . ? O2 C1 1.423(2) . ? O2 C19 1.429(2) . ? O3 C4 1.217(2) . ? O4 N1 1.4254(19) . ? O4 C7 1.4475(19) . ? O5 C14 1.408(2) . ? O5 C15 1.435(2) . ? O6 C14 1.415(2) . ? O6 C17 1.435(2) . ? O7 C9 1.367(2) . ? O7 C21 1.431(2) . ? O8 C11 1.366(2) . ? O8 C22 1.416(2) . ? N1 C6 1.278(2) . ? C1 C2 1.517(2) . ? C1 C7 1.523(2) . ? C2 C3 1.345(3) . ? C2 C20 1.511(3) . ? C3 C4 1.467(3) . ? C4 C5 1.531(2) . ? C5 C6 1.522(2) . ? C5 C7 1.525(2) . ? C6 C8 1.477(2) . ? C8 C13 1.397(2) . ? C8 C9 1.414(2) . ? C9 C10 1.385(2) . ? C10 C11 1.397(2) . ? C11 C12 1.389(2) . ? C12 C13 1.398(2) . ? C13 C14 1.504(2) . ? C15 C16 1.515(3) . ? C16 C17 1.513(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C18 116.23(15) . . ? C1 O2 C19 116.20(15) . . ? N1 O4 C7 106.77(11) . . ? C14 O5 C15 111.08(14) . . ? C14 O6 C17 110.81(14) . . ? C9 O7 C21 117.29(14) . . ? C11 O8 C22 117.89(15) . . ? C6 N1 O4 109.05(13) . . ? O1 C1 O2 111.11(13) . . ? O1 C1 C2 106.57(14) . . ? O2 C1 C2 112.42(13) . . ? O1 C1 C7 112.84(13) . . ? O2 C1 C7 101.57(13) . . ? C2 C1 C7 112.45(14) . . ? C3 C2 C20 121.65(17) . . ? C3 C2 C1 119.80(16) . . ? C20 C2 C1 118.55(16) . . ? C2 C3 C4 124.19(16) . . ? O3 C4 C3 121.37(15) . . ? O3 C4 C5 120.52(15) . . ? C3 C4 C5 118.07(14) . . ? C6 C5 C7 98.11(12) . . ? C6 C5 C4 109.10(13) . . ? C7 C5 C4 114.94(13) . . ? N1 C6 C8 121.29(14) . . ? N1 C6 C5 112.87(14) . . ? C8 C6 C5 125.84(14) . . ? O4 C7 C1 109.63(13) . . ? O4 C7 C5 103.61(12) . . ? C1 C7 C5 115.21(12) . . ? C13 C8 C9 118.26(15) . . ? C13 C8 C6 124.07(14) . . ? C9 C8 C6 117.66(14) . . ? O7 C9 C10 123.49(15) . . ? O7 C9 C8 115.35(14) . . ? C10 C9 C8 121.14(15) . . ? C9 C10 C11 119.16(15) . . ? O8 C11 C12 124.55(15) . . ? O8 C11 C10 114.27(15) . . ? C12 C11 C10 121.15(15) . . ? C11 C12 C13 119.15(15) . . ? C8 C13 C12 121.13(15) . . ? C8 C13 C14 121.59(14) . . ? C12 C13 C14 117.11(14) . . ? O5 C14 O6 110.76(13) . . ? O5 C14 C13 108.76(13) . . ? O6 C14 C13 107.00(12) . . ? O5 C15 C16 110.74(15) . . ? C17 C16 C15 108.62(16) . . ? O6 C17 C16 110.18(16) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.469 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.091 # Attachment '- isoxazoline_5.cif' data_shelxl_5 _database_code_depnum_ccdc_archive 'CCDC 859932' #TrackingRef '- isoxazoline_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H27 N O8' _chemical_formula_sum 'C22 H27 N O8' _chemical_formula_weight 433.45 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5986(8) _cell_length_b 9.3898(10) _cell_length_c 26.681(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.782(3) _cell_angle_gamma 90.00 _cell_volume 2154.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 169(2) _cell_measurement_reflns_used 19156 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 169(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19156 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4910 _reflns_number_gt 3719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2004 (Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0746P)^2^+0.4173P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4910 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.68609(14) -0.26005(13) 0.43132(5) 0.0459(3) Uani 1 1 d . . . O2 O 0.9929(2) -0.41337(17) 0.42705(9) 0.0916(7) Uani 1 1 d . . . O3 O 0.97143(13) 0.13560(11) 0.38705(4) 0.0338(3) Uani 1 1 d . . . O4 O 1.10752(12) -0.02499(13) 0.43850(4) 0.0357(3) Uani 1 1 d . . . O5 O 0.44194(16) -0.07115(14) 0.28864(5) 0.0508(4) Uani 1 1 d . . . O6 O 0.65666(16) 0.05044(14) 0.25835(5) 0.0492(3) Uani 1 1 d . . . O7 O 0.39335(15) 0.45825(13) 0.33048(4) 0.0440(3) Uani 1 1 d . . . O8 O 0.64051(14) 0.19908(12) 0.46742(4) 0.0385(3) Uani 1 1 d . . . N1 N 0.60302(16) -0.14776(15) 0.40809(6) 0.0385(3) Uani 1 1 d . . . C1 C 0.8417(2) -0.21050(18) 0.44544(6) 0.0382(4) Uani 1 1 d . . . H1 H 0.8638 -0.2300 0.4817 0.046 Uiso 1 1 calc R . . C2 C 0.9476(2) -0.2974(2) 0.41268(9) 0.0538(5) Uani 1 1 d . . . C3 C 0.9830(2) -0.2373(2) 0.36379(8) 0.0499(5) Uani 1 1 d . . . H3 H 0.9954 -0.2990 0.3359 0.060 Uiso 1 1 calc R . . C4 C 0.99817(19) -0.09807(19) 0.35766(6) 0.0376(4) Uani 1 1 d . . . C5 C 0.98154(17) -0.00485(16) 0.40421(5) 0.0296(3) Uani 1 1 d . . . C6 C 0.84022(17) -0.05000(16) 0.43530(5) 0.0291(3) Uani 1 1 d . . . H6 H 0.8405 0.0030 0.4678 0.035 Uiso 1 1 calc R . . C7 C 0.68312(17) -0.03353(17) 0.40934(5) 0.0291(3) Uani 1 1 d . . . C8 C 0.61398(17) 0.09772(16) 0.38780(5) 0.0286(3) Uani 1 1 d . . . C9 C 0.56145(17) 0.10661(17) 0.33800(5) 0.0304(3) Uani 1 1 d . . . C10 C 0.48684(18) 0.22800(18) 0.32067(6) 0.0337(3) Uani 1 1 d . . . H10 H 0.4497 0.2317 0.2870 0.040 Uiso 1 1 calc R . . C11 C 0.46587(18) 0.34369(17) 0.35172(6) 0.0335(3) Uani 1 1 d . . . C12 C 0.51947(19) 0.33909(17) 0.40136(6) 0.0337(3) Uani 1 1 d . . . H12 H 0.5069 0.4189 0.4228 0.040 Uiso 1 1 calc R . . C13 C 0.59113(18) 0.21636(17) 0.41880(5) 0.0308(3) Uani 1 1 d . . . C14 C 1.0406(3) -0.0299(2) 0.30896(6) 0.0526(5) Uani 1 1 d . . . H14A H 1.1427 0.0156 0.3124 0.063 Uiso 1 1 calc R . . H14B H 0.9624 0.0419 0.2999 0.063 Uiso 1 1 calc R . . H14C H 1.0444 -0.1027 0.2827 0.063 Uiso 1 1 calc R . . C15 C 0.5869(2) -0.01139(18) 0.30072(6) 0.0359(4) Uani 1 1 d . . . H15 H 0.6571 -0.0856 0.3156 0.043 Uiso 1 1 calc R . . C16 C 0.4592(3) -0.1845(2) 0.25286(8) 0.0650(6) Uani 1 1 d . . . H16A H 0.3556 -0.2232 0.2437 0.078 Uiso 1 1 calc R . . H16B H 0.5217 -0.2623 0.2680 0.078 Uiso 1 1 calc R . . C17 C 0.5384(3) -0.1297(2) 0.20651(8) 0.0709(7) Uani 1 1 d . . . H17A H 0.5610 -0.2101 0.1837 0.085 Uiso 1 1 calc R . . H17B H 0.4691 -0.0622 0.1886 0.085 Uiso 1 1 calc R . . C18 C 0.6860(3) -0.0569(3) 0.22121(8) 0.0643(6) Uani 1 1 d . . . H18A H 0.7607 -0.1276 0.2349 0.077 Uiso 1 1 calc R . . H18B H 0.7327 -0.0123 0.1913 0.077 Uiso 1 1 calc R . . C19 C 0.9868(2) 0.24569(19) 0.42370(7) 0.0448(4) Uani 1 1 d . . . H19A H 1.0970 0.2693 0.4285 0.054 Uiso 1 1 calc R . . H19B H 0.9438 0.2129 0.4555 0.054 Uiso 1 1 calc R . . H19C H 0.9301 0.3304 0.4123 0.054 Uiso 1 1 calc R . . C20 C 1.25955(19) -0.0034(2) 0.41806(7) 0.0458(4) Uani 1 1 d . . . H20A H 1.2621 0.0879 0.4003 0.055 Uiso 1 1 calc R . . H20B H 1.2831 -0.0807 0.3947 0.055 Uiso 1 1 calc R . . H20C H 1.3372 -0.0026 0.4453 0.055 Uiso 1 1 calc R . . C21 C 0.3646(3) 0.5784(2) 0.36140(8) 0.0517(5) Uani 1 1 d . . . H21A H 0.3008 0.5496 0.3898 0.062 Uiso 1 1 calc R . . H21B H 0.3096 0.6515 0.3418 0.062 Uiso 1 1 calc R . . H21C H 0.4637 0.6170 0.3739 0.062 Uiso 1 1 calc R . . C22 C 0.6406(2) 0.3213(2) 0.49940(6) 0.0473(5) Uani 1 1 d . . . H22A H 0.7007 0.3979 0.4839 0.057 Uiso 1 1 calc R . . H22B H 0.6879 0.2964 0.5319 0.057 Uiso 1 1 calc R . . H22C H 0.5335 0.3533 0.5043 0.057 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 0.0359(6) 0.0328(6) 0.0690(8) 0.0115(6) -0.0040(6) -0.0027(5) O2 0.0861(13) 0.0387(8) 0.1507(19) 0.0244(10) 0.0297(12) 0.0215(8) O3 0.0409(6) 0.0299(6) 0.0306(5) 0.0028(4) -0.0026(4) -0.0008(5) O4 0.0275(5) 0.0454(7) 0.0342(6) 0.0073(5) -0.0038(4) -0.0005(5) O5 0.0506(8) 0.0503(8) 0.0514(7) -0.0216(6) -0.0046(6) -0.0057(6) O6 0.0625(8) 0.0494(7) 0.0361(6) -0.0118(6) 0.0124(6) 0.0024(7) O7 0.0547(8) 0.0358(6) 0.0411(6) -0.0005(5) -0.0064(5) 0.0159(6) O8 0.0511(7) 0.0370(6) 0.0274(5) -0.0071(5) -0.0056(5) 0.0086(5) N1 0.0339(7) 0.0317(7) 0.0500(8) 0.0016(6) -0.0031(6) 0.0014(6) C1 0.0370(9) 0.0357(9) 0.0419(9) 0.0085(7) -0.0044(7) -0.0002(7) C2 0.0456(11) 0.0293(9) 0.0867(15) 0.0027(9) 0.0057(10) 0.0043(8) C3 0.0452(10) 0.0428(10) 0.0619(12) -0.0164(9) 0.0092(9) 0.0033(9) C4 0.0342(8) 0.0425(9) 0.0362(8) -0.0080(7) 0.0031(6) 0.0034(7) C5 0.0300(7) 0.0303(8) 0.0283(7) 0.0016(6) -0.0027(6) 0.0015(6) C6 0.0296(8) 0.0309(7) 0.0266(7) 0.0005(6) -0.0017(5) 0.0020(6) C7 0.0289(7) 0.0314(7) 0.0272(7) -0.0043(6) 0.0007(5) 0.0009(6) C8 0.0262(7) 0.0302(7) 0.0294(7) -0.0027(6) 0.0004(5) 0.0010(6) C9 0.0292(7) 0.0333(8) 0.0288(7) -0.0043(6) 0.0003(6) -0.0001(7) C10 0.0355(8) 0.0374(9) 0.0280(7) -0.0021(6) -0.0022(6) 0.0038(7) C11 0.0327(8) 0.0321(8) 0.0357(8) 0.0012(6) 0.0002(6) 0.0048(7) C12 0.0364(8) 0.0315(8) 0.0332(8) -0.0062(6) 0.0011(6) 0.0037(7) C13 0.0302(7) 0.0337(8) 0.0283(7) -0.0041(6) -0.0012(6) 0.0010(7) C14 0.0584(12) 0.0669(13) 0.0327(9) -0.0078(9) 0.0070(8) 0.0029(11) C15 0.0410(9) 0.0378(9) 0.0288(7) -0.0056(6) -0.0028(6) 0.0071(7) C16 0.0854(16) 0.0521(12) 0.0573(13) -0.0254(10) -0.0094(11) -0.0062(12) C17 0.125(2) 0.0502(12) 0.0368(10) -0.0155(9) -0.0149(11) 0.0128(13) C18 0.0912(17) 0.0626(14) 0.0395(10) -0.0149(10) 0.0162(10) 0.0144(12) C19 0.0544(11) 0.0336(9) 0.0465(10) -0.0058(8) 0.0016(8) -0.0066(8) C20 0.0294(8) 0.0575(11) 0.0505(10) 0.0095(9) -0.0006(7) 0.0014(8) C21 0.0631(13) 0.0361(10) 0.0558(11) -0.0047(8) -0.0066(9) 0.0166(9) C22 0.0651(12) 0.0435(10) 0.0330(8) -0.0128(7) -0.0059(8) 0.0063(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.4121(18) . ? O1 C1 1.461(2) . ? O2 C2 1.217(2) . ? O3 C5 1.3984(18) . ? O3 C19 1.428(2) . ? O4 C5 1.4209(17) . ? O4 C20 1.4377(19) . ? O5 C15 1.400(2) . ? O5 C16 1.439(2) . ? O6 C15 1.412(2) . ? O6 C18 1.438(2) . ? O7 C11 1.3629(19) . ? O7 C21 1.421(2) . ? O8 C13 1.3691(18) . ? O8 C22 1.4299(19) . ? N1 C7 1.275(2) . ? C1 C2 1.510(3) . ? C1 C6 1.531(2) . ? C1 H1 1.0000 . ? C2 C3 1.457(3) . ? C3 C4 1.325(3) . ? C3 H3 0.9500 . ? C4 C14 1.498(2) . ? C4 C5 1.528(2) . ? C5 C6 1.540(2) . ? C6 C7 1.518(2) . ? C6 H6 1.0000 . ? C7 C8 1.481(2) . ? C8 C9 1.400(2) . ? C8 C13 1.403(2) . ? C9 C10 1.384(2) . ? C9 C15 1.507(2) . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 C12 1.397(2) . ? C12 C13 1.384(2) . ? C12 H12 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15 1.0000 . ? C16 C17 1.510(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.489(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 N1 O1 C1 109.35(12) . . ? C5 O3 C19 116.98(12) . . ? C5 O4 C20 115.22(12) . . ? C15 O5 C16 110.47(15) . . ? C15 O6 C18 110.12(15) . . ? C11 O7 C21 117.86(13) . . ? C13 O8 C22 117.91(13) . . ? C7 N1 O1 110.29(13) . . ? O1 C1 C2 103.65(15) . . ? O1 C1 C6 105.21(13) . . ? C2 C1 C6 115.66(14) . . ? O1 C1 H1 110.6 . . ? C2 C1 H1 110.6 . . ? C6 C1 H1 110.6 . . ? O2 C2 C3 124.0(2) . . ? O2 C2 C1 119.6(2) . . ? C3 C2 C1 116.37(16) . . ? C4 C3 C2 120.98(17) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C14 123.67(17) . . ? C3 C4 C5 117.05(16) . . ? C14 C4 C5 119.15(15) . . ? O3 C5 O4 112.32(12) . . ? O3 C5 C4 106.27(12) . . ? O4 C5 C4 111.60(12) . . ? O3 C5 C6 112.96(12) . . ? O4 C5 C6 102.52(11) . . ? C4 C5 C6 111.31(13) . . ? C7 C6 C1 100.73(13) . . ? C7 C6 C5 115.47(12) . . ? C1 C6 C5 111.18(13) . . ? C7 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? N1 C7 C8 118.43(13) . . ? N1 C7 C6 113.79(14) . . ? C8 C7 C6 127.74(13) . . ? C9 C8 C13 117.79(14) . . ? C9 C8 C7 122.72(13) . . ? C13 C8 C7 119.38(13) . . ? C10 C9 C8 120.55(14) . . ? C10 C9 C15 117.10(13) . . ? C8 C9 C15 122.33(14) . . ? C11 C10 C9 120.76(14) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? O7 C11 C10 115.76(14) . . ? O7 C11 C12 124.18(14) . . ? C10 C11 C12 120.06(15) . . ? C13 C12 C11 118.94(14) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? O8 C13 C12 123.23(13) . . ? O8 C13 C8 114.87(14) . . ? C12 C13 C8 121.88(14) . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 O6 111.54(13) . . ? O5 C15 C9 108.05(13) . . ? O6 C15 C9 107.05(13) . . ? O5 C15 H15 110.0 . . ? O6 C15 H15 110.0 . . ? C9 C15 H15 110.0 . . ? O5 C16 C17 110.09(18) . . ? O5 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? O5 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.2 . . ? C18 C17 C16 109.44(17) . . ? C18 C17 H17A 109.8 . . ? C16 C17 H17A 109.8 . . ? C18 C17 H17B 109.8 . . ? C16 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? O6 C18 C17 110.29(19) . . ? O6 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? O6 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O7 C21 H21A 109.5 . . ? O7 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O7 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O8 C22 H22A 109.5 . . ? O8 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O8 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C1 O1 N1 C7 -4.60(18) . . . . ? N1 O1 C1 C2 -114.24(15) . . . . ? N1 O1 C1 C6 7.62(17) . . . . ? O1 C1 C2 O2 -87.8(2) . . . . ? C6 C1 C2 O2 157.6(2) . . . . ? O1 C1 C2 C3 89.28(19) . . . . ? C6 C1 C2 C3 -25.3(3) . . . . ? O2 C2 C3 C4 -148.0(2) . . . . ? C1 C2 C3 C4 35.0(3) . . . . ? C2 C3 C4 C14 177.50(18) . . . . ? C2 C3 C4 C5 1.7(3) . . . . ? C19 O3 C5 O4 -45.33(18) . . . . ? C19 O3 C5 C4 -167.64(13) . . . . ? C19 O3 C5 C6 70.03(17) . . . . ? C20 O4 C5 O3 -64.04(17) . . . . ? C20 O4 C5 C4 55.19(18) . . . . ? C20 O4 C5 C6 174.42(14) . . . . ? C3 C4 C5 O3 -168.69(16) . . . . ? C14 C4 C5 O3 15.3(2) . . . . ? C3 C4 C5 O4 68.6(2) . . . . ? C14 C4 C5 O4 -107.45(17) . . . . ? C3 C4 C5 C6 -45.3(2) . . . . ? C14 C4 C5 C6 138.67(16) . . . . ? O1 C1 C6 C7 -7.29(15) . . . . ? C2 C1 C6 C7 106.41(17) . . . . ? O1 C1 C6 C5 -130.17(13) . . . . ? C2 C1 C6 C5 -16.5(2) . . . . ? O3 C5 C6 C7 56.04(17) . . . . ? O4 C5 C6 C7 177.15(12) . . . . ? C4 C5 C6 C7 -63.42(17) . . . . ? O3 C5 C6 C1 169.99(12) . . . . ? O4 C5 C6 C1 -68.91(15) . . . . ? C4 C5 C6 C1 50.53(17) . . . . ? O1 N1 C7 C8 -178.57(12) . . . . ? O1 N1 C7 C6 -0.63(18) . . . . ? C1 C6 C7 N1 5.16(17) . . . . ? C5 C6 C7 N1 125.01(15) . . . . ? C1 C6 C7 C8 -177.13(14) . . . . ? C5 C6 C7 C8 -57.3(2) . . . . ? N1 C7 C8 C9 -57.3(2) . . . . ? C6 C7 C8 C9 125.05(16) . . . . ? N1 C7 C8 C13 118.87(16) . . . . ? C6 C7 C8 C13 -58.7(2) . . . . ? C13 C8 C9 C10 -1.2(2) . . . . ? C7 C8 C9 C10 175.02(14) . . . . ? C13 C8 C9 C15 176.90(14) . . . . ? C7 C8 C9 C15 -6.8(2) . . . . ? C8 C9 C10 C11 1.5(2) . . . . ? C15 C9 C10 C11 -176.78(14) . . . . ? C21 O7 C11 C10 178.03(16) . . . . ? C21 O7 C11 C12 -2.8(2) . . . . ? C9 C10 C11 O7 178.93(14) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? O7 C11 C12 C13 179.82(15) . . . . ? C10 C11 C12 C13 -1.0(2) . . . . ? C22 O8 C13 C12 -10.4(2) . . . . ? C22 O8 C13 C8 171.62(14) . . . . ? C11 C12 C13 O8 -176.67(15) . . . . ? C11 C12 C13 C8 1.2(2) . . . . ? C9 C8 C13 O8 177.96(13) . . . . ? C7 C8 C13 O8 1.6(2) . . . . ? C9 C8 C13 C12 -0.1(2) . . . . ? C7 C8 C13 C12 -176.49(14) . . . . ? C16 O5 C15 O6 62.4(2) . . . . ? C16 O5 C15 C9 179.76(16) . . . . ? C18 O6 C15 O5 -62.6(2) . . . . ? C18 O6 C15 C9 179.39(16) . . . . ? C10 C9 C15 O5 -69.60(18) . . . . ? C8 C9 C15 O5 112.19(17) . . . . ? C10 C9 C15 O6 50.66(19) . . . . ? C8 C9 C15 O6 -127.55(16) . . . . ? C15 O5 C16 C17 -57.1(2) . . . . ? O5 C16 C17 C18 52.9(3) . . . . ? C15 O6 C18 C17 58.0(2) . . . . ? C16 C17 C18 O6 -53.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.403 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.096 # Attachment '- nitrile_9a.cif' data_shelxl_9a _database_code_depnum_ccdc_archive 'CCDC 859933' #TrackingRef '- nitrile_9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O4' _chemical_formula_sum 'C13 H15 N O4' _chemical_formula_weight 249.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8683(12) _cell_length_b 9.2342(15) _cell_length_c 10.5078(19) _cell_angle_alpha 111.922(4) _cell_angle_beta 90.897(4) _cell_angle_gamma 96.504(4) _cell_volume 613.06(18) _cell_formula_units_Z 2 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used 5877 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5877 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2771 _reflns_number_gt 2189 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2004 (Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0851P)^2^+0.0154P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2771 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 0.77451(15) 0.18201(10) 0.90728(9) 0.0298(2) Uani 1 1 d . . . O2 O 0.88556(17) 0.61881(14) 0.68805(11) 0.0451(3) Uani 1 1 d . . . O3 O 0.60611(17) 0.72739(12) 0.77502(10) 0.0392(3) Uani 1 1 d . . . O4 O 0.76855(14) 0.70485(9) 1.22945(8) 0.0296(2) Uani 1 1 d . . . N1 N 0.7288(2) 0.17715(13) 0.58095(12) 0.0385(3) Uani 1 1 d . . . C1 C 0.76438(17) 0.33833(13) 0.94135(12) 0.0215(3) Uani 1 1 d . . . C2 C 0.74158(17) 0.38433(13) 0.82850(12) 0.0208(3) Uani 1 1 d . . . C3 C 0.72531(17) 0.54184(13) 0.85258(12) 0.0203(3) Uani 1 1 d . . . C4 C 0.73234(17) 0.65203(13) 0.98576(12) 0.0215(3) Uani 1 1 d . . . H4 H 0.7199 0.7588 1.0020 0.026 Uiso 1 1 calc R . . C5 C 0.75785(17) 0.60487(14) 1.09550(12) 0.0218(3) Uani 1 1 d . . . C6 C 0.77383(17) 0.44825(14) 1.07399(12) 0.0225(3) Uani 1 1 d . . . H6 H 0.7910 0.4177 1.1499 0.027 Uiso 1 1 calc R . . C7 C 0.73536(19) 0.26860(13) 0.69153(13) 0.0253(3) Uani 1 1 d . . . C8 C 0.70030(19) 0.59198(13) 0.73287(12) 0.0248(3) Uani 1 1 d . . . H8 H 0.6183 0.5057 0.6567 0.030 Uiso 1 1 calc R . . C9 C 0.8683(3) 0.6604(3) 0.5686(2) 0.0636(6) Uani 1 1 d . . . H9A H 0.7947 0.5712 0.4920 0.076 Uiso 1 1 calc R . . H9B H 1.0007 0.6825 0.5389 0.076 Uiso 1 1 calc R . . C10 C 0.7628(3) 0.80361(19) 0.60288(18) 0.0551(5) Uani 1 1 d . . . H10A H 0.8453 0.8966 0.6700 0.066 Uiso 1 1 calc R . . H10B H 0.7379 0.8247 0.5187 0.066 Uiso 1 1 calc R . . C11 C 0.5737(3) 0.77575(19) 0.66194(16) 0.0495(5) Uani 1 1 d . . . H11A H 0.5110 0.8735 0.6942 0.059 Uiso 1 1 calc R . . H11B H 0.4840 0.6931 0.5901 0.059 Uiso 1 1 calc R . . C12 C 0.7796(2) 0.12600(15) 1.01710(15) 0.0336(3) Uani 1 1 d . . . H12A H 0.8951 0.1804 1.0797 0.040 Uiso 1 1 calc R . . H12B H 0.7870 0.0125 0.9794 0.040 Uiso 1 1 calc R . . H12C H 0.6604 0.1467 1.0674 0.040 Uiso 1 1 calc R . . C13 C 0.7590(3) 0.86778(15) 1.25597(14) 0.0369(3) Uani 1 1 d . . . H13A H 0.8683 0.9082 1.2146 0.044 Uiso 1 1 calc R . . H13B H 0.7679 0.9276 1.3554 0.044 Uiso 1 1 calc R . . H13C H 0.6344 0.8789 1.2161 0.044 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 0.0428(6) 0.0208(4) 0.0288(5) 0.0120(4) 0.0042(4) 0.0064(4) O2 0.0424(6) 0.0696(7) 0.0450(6) 0.0418(6) 0.0200(5) 0.0207(5) O3 0.0573(7) 0.0408(6) 0.0318(5) 0.0213(4) 0.0103(5) 0.0278(5) O4 0.0440(6) 0.0239(4) 0.0189(4) 0.0053(3) 0.0024(4) 0.0058(4) N1 0.0563(8) 0.0287(6) 0.0275(6) 0.0063(4) 0.0036(5) 0.0082(5) C1 0.0198(6) 0.0205(5) 0.0266(6) 0.0112(4) 0.0035(4) 0.0039(4) C2 0.0202(6) 0.0207(5) 0.0211(6) 0.0077(4) 0.0023(4) 0.0021(4) C3 0.0180(6) 0.0220(5) 0.0223(6) 0.0100(4) 0.0016(4) 0.0028(4) C4 0.0222(6) 0.0190(5) 0.0232(6) 0.0075(4) 0.0009(4) 0.0039(4) C5 0.0187(6) 0.0258(6) 0.0202(6) 0.0080(4) 0.0027(4) 0.0025(4) C6 0.0216(6) 0.0271(6) 0.0226(6) 0.0135(5) 0.0025(4) 0.0030(4) C7 0.0301(7) 0.0217(5) 0.0258(6) 0.0105(5) 0.0027(5) 0.0040(5) C8 0.0325(7) 0.0204(5) 0.0214(6) 0.0078(4) -0.0006(5) 0.0038(5) C9 0.0809(14) 0.0891(14) 0.0518(11) 0.0546(10) 0.0325(10) 0.0330(11) C10 0.0938(15) 0.0429(9) 0.0389(8) 0.0287(7) 0.0017(9) 0.0038(9) C11 0.0816(13) 0.0435(8) 0.0355(8) 0.0227(7) 0.0011(8) 0.0291(8) C12 0.0453(8) 0.0255(6) 0.0367(7) 0.0187(5) 0.0058(6) 0.0070(5) C13 0.0587(10) 0.0247(6) 0.0241(6) 0.0054(5) 0.0067(6) 0.0050(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 1.3617(14) . ? O1 C12 1.4315(15) . ? O2 C8 1.3917(17) . ? O2 C9 1.4500(18) . ? O3 C8 1.3989(14) . ? O3 C11 1.4392(16) . ? O4 C5 1.3601(13) . ? O4 C13 1.4336(15) . ? N1 C7 1.1499(17) . ? C1 C6 1.3794(16) . ? C1 C2 1.4130(16) . ? C2 C3 1.3981(16) . ? C2 C7 1.4334(16) . ? C3 C4 1.3855(16) . ? C3 C8 1.5074(16) . ? C4 C5 1.3914(16) . ? C4 H4 0.9500 . ? C5 C6 1.3954(16) . ? C6 H6 0.9500 . ? C8 H8 1.0000 . ? C9 C10 1.508(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.486(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 O1 C12 117.41(9) . . ? C8 O2 C9 110.03(12) . . ? C8 O3 C11 110.67(10) . . ? C5 O4 C13 117.00(9) . . ? O1 C1 C6 124.78(11) . . ? O1 C1 C2 114.91(10) . . ? C6 C1 C2 120.31(10) . . ? C3 C2 C1 119.36(10) . . ? C3 C2 C7 121.27(10) . . ? C1 C2 C7 119.37(10) . . ? C4 C3 C2 120.39(10) . . ? C4 C3 C8 119.85(10) . . ? C2 C3 C8 119.76(10) . . ? C3 C4 C5 119.38(10) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O4 C5 C4 123.53(10) . . ? O4 C5 C6 115.23(10) . . ? C4 C5 C6 121.24(10) . . ? C1 C6 C5 119.29(11) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C2 178.96(13) . . ? O2 C8 O3 111.66(11) . . ? O2 C8 C3 108.00(10) . . ? O3 C8 C3 109.11(9) . . ? O2 C8 H8 109.3 . . ? O3 C8 H8 109.3 . . ? C3 C8 H8 109.3 . . ? O2 C9 C10 109.92(14) . . ? O2 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O2 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C9 109.30(14) . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? O3 C11 C10 110.35(14) . . ? O3 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? O3 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C12 O1 C1 C6 5.21(18) . . . . ? C12 O1 C1 C2 -174.46(11) . . . . ? O1 C1 C2 C3 178.60(10) . . . . ? C6 C1 C2 C3 -1.09(17) . . . . ? O1 C1 C2 C7 -1.33(16) . . . . ? C6 C1 C2 C7 178.98(11) . . . . ? C1 C2 C3 C4 0.29(17) . . . . ? C7 C2 C3 C4 -179.78(11) . . . . ? C1 C2 C3 C8 -179.81(10) . . . . ? C7 C2 C3 C8 0.13(18) . . . . ? C2 C3 C4 C5 0.68(17) . . . . ? C8 C3 C4 C5 -179.23(11) . . . . ? C13 O4 C5 C4 -2.09(18) . . . . ? C13 O4 C5 C6 178.07(11) . . . . ? C3 C4 C5 O4 179.29(11) . . . . ? C3 C4 C5 C6 -0.88(18) . . . . ? O1 C1 C6 C5 -178.76(11) . . . . ? C2 C1 C6 C5 0.89(18) . . . . ? O4 C5 C6 C1 179.93(10) . . . . ? C4 C5 C6 C1 0.09(18) . . . . ? C3 C2 C7 N1 -24(8) . . . . ? C1 C2 C7 N1 156(8) . . . . ? C9 O2 C8 O3 -62.69(16) . . . . ? C9 O2 C8 C3 177.35(12) . . . . ? C11 O3 C8 O2 62.64(16) . . . . ? C11 O3 C8 C3 -178.06(12) . . . . ? C4 C3 C8 O2 96.32(13) . . . . ? C2 C3 C8 O2 -83.59(13) . . . . ? C4 C3 C8 O3 -25.24(15) . . . . ? C2 C3 C8 O3 154.86(11) . . . . ? C8 O2 C9 C10 57.6(2) . . . . ? O2 C9 C10 C11 -53.1(2) . . . . ? C8 O3 C11 C10 -57.42(17) . . . . ? C9 C10 C11 O3 52.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.364 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.057 # Attachment '- isoxazole_8c.CIF' data_shelxl_8c _database_code_depnum_ccdc_archive 'CCDC 859934' #TrackingRef '- isoxazole_8c.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O8' _chemical_formula_sum 'C21 H23 N O8' _chemical_formula_weight 417.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.301(5) _cell_length_b 8.437(4) _cell_length_c 23.760(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.05(4) _cell_angle_gamma 90.00 _cell_volume 2033.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19165 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9492 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19165 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4651 _reflns_number_gt 3884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2002 (Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4651 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.262 _refine_ls_restrained_S_all 1.262 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20195(11) -0.00484(13) 0.60006(5) 0.0270(3) Uani 1 1 d . . . O2 O 0.01781(12) -0.09703(14) 0.67035(5) 0.0309(3) Uani 1 1 d . . . O3 O -0.09875(11) -0.02858(15) 0.57988(5) 0.0298(3) Uani 1 1 d . . . O4 O 0.10783(13) 0.50278(14) 0.64889(6) 0.0356(3) Uani 1 1 d . . . O5 O 0.62955(11) 0.72887(14) 0.57609(5) 0.0303(3) Uani 1 1 d . . . O6 O 0.20643(12) 0.46736(15) 0.52529(5) 0.0298(3) Uani 1 1 d . . . O7 O 0.44386(11) 0.31248(14) 0.71900(5) 0.0245(3) Uani 1 1 d . . . O8 O 0.66254(11) 0.29314(15) 0.70654(5) 0.0268(3) Uani 1 1 d . . . N1 N 0.30844(13) 0.09332(16) 0.59069(6) 0.0262(3) Uani 1 1 d . . . C1 C 0.11260(14) 0.08843(18) 0.61801(6) 0.0219(3) Uani 1 1 d . . . C2 C -0.01604(14) 0.02383(18) 0.62998(7) 0.0231(3) Uani 1 1 d . . . C3 C -0.09180(15) 0.1575(2) 0.65143(7) 0.0272(3) Uani 1 1 d . . . H1 H -0.1758 0.1331 0.6605 0.033 Uiso 1 1 calc R . . C4 C -0.05050(16) 0.3065(2) 0.65864(7) 0.0278(3) Uani 1 1 d . . . H2 H -0.1043 0.3800 0.6743 0.033 Uiso 1 1 calc R . . C5 C 0.07545(15) 0.36435(19) 0.64355(6) 0.0241(3) Uani 1 1 d . . . C6 C 0.15329(14) 0.24103(18) 0.62182(6) 0.0211(3) Uani 1 1 d . . . C7 C 0.27814(14) 0.23735(18) 0.60385(6) 0.0211(3) Uani 1 1 d . . . C8 C 0.36985(14) 0.36784(17) 0.59716(6) 0.0205(3) Uani 1 1 d . . . C9 C 0.49528(14) 0.37841(17) 0.63076(6) 0.0193(3) Uani 1 1 d . . . C10 C 0.58105(14) 0.49764(17) 0.62159(6) 0.0207(3) Uani 1 1 d . . . H3 H 0.6676 0.5012 0.6433 0.025 Uiso 1 1 calc R . . C11 C 0.53985(15) 0.61251(18) 0.58030(6) 0.0217(3) Uani 1 1 d . . . C12 C 0.41483(15) 0.60703(18) 0.54705(6) 0.0224(3) Uani 1 1 d . . . H4 H 0.3873 0.6858 0.5189 0.027 Uiso 1 1 calc R . . C13 C 0.33083(15) 0.48386(18) 0.55575(6) 0.0221(3) Uani 1 1 d . . . C14 C -0.0916(2) -0.1757(2) 0.68861(9) 0.0399(4) Uani 1 1 d . . . H5 H -0.1141 -0.1206 0.7219 0.048 Uiso 1 1 calc R . . H6 H -0.0675 -0.2856 0.6989 0.048 Uiso 1 1 calc R . . H7 H -0.1678 -0.1743 0.6575 0.048 Uiso 1 1 calc R . . C15 C -0.0519(2) -0.1620(2) 0.55184(9) 0.0408(4) Uani 1 1 d . . . H8 H 0.0010 -0.1246 0.5240 0.049 Uiso 1 1 calc R . . H9 H -0.1272 -0.2232 0.5321 0.049 Uiso 1 1 calc R . . H10 H 0.0025 -0.2293 0.5802 0.049 Uiso 1 1 calc R . . C16 C 0.58456(17) 0.8624(2) 0.54111(8) 0.0337(4) Uani 1 1 d . . . H11 H 0.5975 0.8423 0.5018 0.040 Uiso 1 1 calc R . . H12 H 0.6347 0.9567 0.5560 0.040 Uiso 1 1 calc R . . H13 H 0.4907 0.8799 0.5415 0.040 Uiso 1 1 calc R . . C17 C 0.16448(17) 0.5766(2) 0.48018(7) 0.0335(4) Uani 1 1 d . . . H14 H 0.1229 0.6683 0.4951 0.040 Uiso 1 1 calc R . . H15 H 0.1008 0.5249 0.4504 0.040 Uiso 1 1 calc R . . H16 H 0.2408 0.6120 0.4640 0.040 Uiso 1 1 calc R . . C18 C 0.53026(14) 0.26963(17) 0.68183(6) 0.0201(3) Uani 1 1 d . . . H17 H 0.5154 0.1566 0.6697 0.024 Uiso 1 1 calc R . . C19 C 0.46707(17) 0.2184(2) 0.77037(7) 0.0297(4) Uani 1 1 d . . . H18 H 0.4478 0.1056 0.7608 0.036 Uiso 1 1 calc R . . H19 H 0.4078 0.2536 0.7966 0.036 Uiso 1 1 calc R . . C20 C 0.60916(18) 0.2358(2) 0.79941(7) 0.0302(4) Uani 1 1 d . . . H20 H 0.6256 0.3458 0.8135 0.036 Uiso 1 1 calc R . . H21 H 0.6277 0.1632 0.8326 0.036 Uiso 1 1 calc R . . C21 C 0.69787(16) 0.1971(2) 0.75723(7) 0.0306(4) Uani 1 1 d . . . H22 H 0.7908 0.2176 0.7747 0.037 Uiso 1 1 calc R . . H23 H 0.6892 0.0835 0.7469 0.037 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 0.0230(5) 0.0209(5) 0.0385(6) -0.0034(4) 0.0093(5) -0.0004(4) O2 0.0265(6) 0.0295(6) 0.0360(6) 0.0083(5) 0.0035(5) -0.0026(5) O3 0.0236(6) 0.0333(6) 0.0308(6) -0.0068(5) -0.0006(5) -0.0051(5) O4 0.0340(7) 0.0245(6) 0.0478(8) -0.0091(5) 0.0059(6) -0.0003(5) O5 0.0215(5) 0.0314(6) 0.0375(6) 0.0136(5) 0.0035(5) -0.0045(5) O6 0.0255(6) 0.0360(6) 0.0238(5) 0.0070(5) -0.0069(4) -0.0050(5) O7 0.0230(5) 0.0298(6) 0.0222(5) 0.0085(4) 0.0076(4) 0.0054(4) O8 0.0175(5) 0.0378(6) 0.0243(5) 0.0118(5) 0.0014(4) 0.0007(4) N1 0.0210(6) 0.0253(6) 0.0332(7) -0.0016(5) 0.0075(5) -0.0030(5) C1 0.0194(7) 0.0232(7) 0.0226(7) -0.0010(5) 0.0024(5) 0.0004(5) C2 0.0196(7) 0.0239(7) 0.0249(7) 0.0004(6) 0.0010(6) -0.0021(6) C3 0.0204(7) 0.0339(8) 0.0275(7) -0.0002(6) 0.0046(6) 0.0021(6) C4 0.0233(7) 0.0321(8) 0.0277(8) -0.0038(6) 0.0039(6) 0.0052(6) C5 0.0225(7) 0.0256(7) 0.0226(7) -0.0043(6) -0.0006(5) 0.0027(6) C6 0.0196(7) 0.0227(7) 0.0198(7) -0.0010(5) 0.0001(5) -0.0003(5) C7 0.0198(7) 0.0246(7) 0.0181(6) 0.0001(5) 0.0006(5) -0.0008(5) C8 0.0208(7) 0.0221(7) 0.0188(6) -0.0003(5) 0.0037(5) -0.0013(5) C9 0.0199(7) 0.0215(7) 0.0168(6) 0.0004(5) 0.0037(5) 0.0016(5) C10 0.0181(6) 0.0249(7) 0.0190(6) 0.0007(5) 0.0032(5) 0.0003(5) C11 0.0209(7) 0.0243(7) 0.0211(6) 0.0019(6) 0.0073(5) -0.0019(5) C12 0.0242(7) 0.0249(7) 0.0182(6) 0.0038(5) 0.0037(5) 0.0017(6) C13 0.0212(7) 0.0270(7) 0.0166(6) -0.0003(5) -0.0005(5) 0.0001(6) C14 0.0358(9) 0.0409(10) 0.0439(10) 0.0126(8) 0.0092(8) -0.0071(8) C15 0.0406(10) 0.0387(10) 0.0422(10) -0.0167(8) 0.0044(8) -0.0072(8) C16 0.0285(8) 0.0307(8) 0.0421(9) 0.0141(7) 0.0062(7) -0.0044(7) C17 0.0253(8) 0.0436(10) 0.0290(8) 0.0110(7) -0.0029(6) 0.0036(7) C18 0.0188(7) 0.0216(7) 0.0195(6) 0.0019(5) 0.0023(5) 0.0011(5) C19 0.0309(8) 0.0355(9) 0.0246(7) 0.0115(6) 0.0101(6) 0.0041(7) C20 0.0365(9) 0.0336(8) 0.0189(7) 0.0074(6) 0.0006(6) -0.0007(7) C21 0.0235(8) 0.0383(9) 0.0277(8) 0.0140(7) -0.0016(6) 0.0029(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 1.3361(19) . ? O1 N1 1.4227(17) . ? O2 C2 1.402(2) . ? O2 C14 1.439(2) . ? O3 C2 1.4087(19) . ? O3 C15 1.434(2) . ? O4 C5 1.215(2) . ? O5 C11 1.3638(19) . ? O5 C16 1.429(2) . ? O6 C13 1.3644(19) . ? O6 C17 1.423(2) . ? O7 C18 1.4060(19) . ? O7 C19 1.4407(18) . ? O8 C18 1.4006(18) . ? O8 C21 1.4443(19) . ? N1 C7 1.306(2) . ? C1 C6 1.352(2) . ? C1 C2 1.505(2) . ? C2 C3 1.510(2) . ? C3 C4 1.328(2) . ? C4 C5 1.487(2) . ? C5 C6 1.462(2) . ? C6 C7 1.424(2) . ? C7 C8 1.477(2) . ? C8 C9 1.398(2) . ? C8 C13 1.396(2) . ? C9 C10 1.381(2) . ? C9 C18 1.514(2) . ? C10 C11 1.392(2) . ? C11 C12 1.389(2) . ? C12 C13 1.391(2) . ? C19 C20 1.513(2) . ? C20 C21 1.505(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 N1 107.46(12) . . ? C2 O2 C14 115.31(13) . . ? C2 O3 C15 115.86(14) . . ? C11 O5 C16 117.09(13) . . ? C13 O6 C17 117.86(13) . . ? C18 O7 C19 111.15(12) . . ? C18 O8 C21 110.81(12) . . ? C7 N1 O1 106.33(13) . . ? O1 C1 C6 111.06(14) . . ? O1 C1 C2 121.68(14) . . ? C6 C1 C2 127.24(14) . . ? O2 C2 O3 113.04(13) . . ? O2 C2 C1 105.70(12) . . ? O3 C2 C1 112.13(13) . . ? O2 C2 C3 113.20(14) . . ? O3 C2 C3 104.34(13) . . ? C1 C2 C3 108.49(13) . . ? C4 C3 C2 125.28(15) . . ? C3 C4 C5 123.56(15) . . ? O4 C5 C6 124.30(15) . . ? O4 C5 C4 121.70(15) . . ? C6 C5 C4 114.00(14) . . ? C1 C6 C7 104.17(13) . . ? C1 C6 C5 121.24(14) . . ? C7 C6 C5 134.51(14) . . ? N1 C7 C6 110.98(14) . . ? N1 C7 C8 118.92(14) . . ? C6 C7 C8 130.08(14) . . ? C9 C8 C13 118.77(13) . . ? C9 C8 C7 122.05(13) . . ? C13 C8 C7 119.17(13) . . ? C10 C9 C8 120.62(13) . . ? C10 C9 C18 119.91(13) . . ? C8 C9 C18 119.08(13) . . ? C9 C10 C11 119.58(14) . . ? O5 C11 C12 123.71(14) . . ? O5 C11 C10 115.20(13) . . ? C12 C11 C10 121.08(14) . . ? C13 C12 C11 118.65(13) . . ? O6 C13 C12 123.26(13) . . ? O6 C13 C8 115.50(13) . . ? C12 C13 C8 121.23(14) . . ? O8 C18 O7 112.11(12) . . ? O8 C18 C9 109.16(12) . . ? O7 C18 C9 105.03(11) . . ? O7 C19 C20 109.69(13) . . ? C21 C20 C19 109.06(14) . . ? O8 C21 C20 109.85(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.526 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.065 # Attachment '- isoxazole_8b.CIF' data_s1 _database_code_depnum_ccdc_archive 'CCDC 859935' #TrackingRef '- isoxazole_8b.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H25 N O9' _chemical_formula_sum 'C22 H25 N O9' _chemical_formula_weight 447.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3141(14) _cell_length_b 11.871(3) _cell_length_c 12.579(2) _cell_angle_alpha 72.852(10) _cell_angle_beta 83.715(8) _cell_angle_gamma 89.902(11) _cell_volume 1036.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6823 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 32.09 _exptl_crystal_description flatplate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details SCALEPACK _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP area detector system' _diffrn_measurement_method \wscan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13525 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 32.09 _reflns_number_total 6823 _reflns_number_gt 5888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'DENZO HKL2000 (W.Minor)' _computing_data_reduction 'DENZO HKL2000 (W.Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for windows(Farrugia,1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0591P)^2^+0.3668P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6823 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _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 H19A H 0.120(2) 0.6678(13) 0.2461(13) 0.023(3) Uiso 1 1 d . . . O8 O 0.26729(11) 0.78474(7) 0.12832(7) 0.02517(17) Uani 1 1 d . . . O3 O 0.22393(11) 1.12969(7) 0.37333(7) 0.02436(16) Uani 1 1 d . . . O4 O 0.30924(11) 1.24779(7) 0.14886(7) 0.02382(16) Uani 1 1 d . . . O2 O 0.05092(11) 1.07661(7) 0.25520(7) 0.02388(16) Uani 1 1 d . . . O1 O 0.19680(12) 0.86852(7) 0.42396(7) 0.02602(17) Uani 1 1 d . . . O7 O 0.70741(13) 0.38001(7) 0.23389(8) 0.03054(19) Uani 1 1 d . . . O5 O 0.64779(12) 0.91061(8) 0.12984(8) 0.03115(19) Uani 1 1 d . . . O9 O 0.17305(13) 0.60239(8) 0.11794(8) 0.03150(19) Uani 1 1 d . . . C1 C 0.28484(14) 0.94541(9) 0.33205(8) 0.01951(18) Uani 1 1 d . . . C11 C 0.46864(14) 0.66480(8) 0.31571(8) 0.01969(18) Uani 1 1 d . . . O6 O 0.68399(13) 0.67036(8) 0.43741(8) 0.0318(2) Uani 1 1 d . . . C5 C 0.52436(14) 0.95603(9) 0.17519(9) 0.02108(18) Uani 1 1 d . . . C16 C 0.39470(14) 0.61386(9) 0.24176(8) 0.02015(18) Uani 1 1 d . . . C4 C 0.48261(15) 1.08131(9) 0.13201(9) 0.02194(19) Uani 1 1 d . . . H4 H 0.5503 1.1275 0.0644 0.026 Uiso 1 1 calc R . . C6 C 0.40946(14) 0.89094(8) 0.27821(8) 0.01879(17) Uani 1 1 d . . . C19 C 0.22535(15) 0.66597(10) 0.18859(9) 0.0230(2) Uani 1 1 d . . . C3 C 0.35281(14) 1.13388(9) 0.18383(8) 0.01957(18) Uani 1 1 d . . . C12 C 0.62214(15) 0.61527(9) 0.36667(9) 0.02138(19) Uani 1 1 d . . . N1 N 0.26247(14) 0.75390(8) 0.42814(8) 0.02599(19) Uani 1 1 d . . . C14 C 0.63181(16) 0.47072(9) 0.26764(9) 0.0227(2) Uani 1 1 d . . . C13 C 0.70495(15) 0.51773(9) 0.34360(9) 0.0232(2) Uani 1 1 d . . . H13 H 0.8089 0.4842 0.3789 0.028 Uiso 1 1 calc R . . C9 C 0.40729(17) 1.31865(10) 0.04543(10) 0.0271(2) Uani 1 1 d . . . H9A H 0.5374 1.3260 0.0551 0.041 Uiso 1 1 calc R . . H9B H 0.3550 1.3971 0.0240 0.041 Uiso 1 1 calc R . . H9C H 0.3963 1.2810 -0.0134 0.041 Uiso 1 1 calc R . . C15 C 0.47473(16) 0.51648(9) 0.21889(9) 0.0234(2) Uani 1 1 d . . . H15 H 0.4228 0.4809 0.1701 0.028 Uiso 1 1 calc R . . C10 C 0.38610(14) 0.76913(9) 0.34107(8) 0.01950(18) Uani 1 1 d . . . C2 C 0.22624(14) 1.07137(8) 0.29083(8) 0.01875(18) Uani 1 1 d . . . C18 C 0.88123(19) 0.33897(11) 0.27087(11) 0.0321(3) Uani 1 1 d . . . H18A H 0.9699 0.4057 0.2514 0.048 Uiso 1 1 calc R . . H18B H 0.9268 0.2805 0.2342 0.048 Uiso 1 1 calc R . . H18C H 0.8655 0.3028 0.3522 0.048 Uiso 1 1 calc R . . C7 C -0.09983(17) 1.02173(12) 0.33734(11) 0.0326(3) Uani 1 1 d . . . H7A H -0.0975 0.9360 0.3518 0.049 Uiso 1 1 calc R . . H7B H -0.2162 1.0507 0.3093 0.049 Uiso 1 1 calc R . . H7C H -0.0886 1.0411 0.4069 0.049 Uiso 1 1 calc R . . C17 C 0.82598(18) 0.61748(12) 0.50218(11) 0.0323(3) Uani 1 1 d . . . H17A H 0.7896 0.5356 0.5438 0.048 Uiso 1 1 calc R . . H17B H 0.8467 0.6613 0.5550 0.048 Uiso 1 1 calc R . . H17C H 0.9396 0.6191 0.4525 0.048 Uiso 1 1 calc R . . C8 C 0.40210(18) 1.14747(11) 0.40366(11) 0.0311(2) Uani 1 1 d . . . H8A H 0.4671 1.0731 0.4192 0.047 Uiso 1 1 calc R . . H8B H 0.3888 1.1742 0.4706 0.047 Uiso 1 1 calc R . . H8C H 0.4724 1.2072 0.3419 0.047 Uiso 1 1 calc R . . C22 C 0.00836(19) 0.64982(12) 0.06998(13) 0.0373(3) Uani 1 1 d . . . H22A H -0.0955 0.6368 0.1302 0.045 Uiso 1 1 calc R . . H22B H -0.0223 0.6077 0.0167 0.045 Uiso 1 1 calc R . . C21 C 0.03332(18) 0.78096(12) 0.00933(11) 0.0332(3) Uani 1 1 d . . . H21A H 0.1209 0.7935 -0.0592 0.040 Uiso 1 1 calc R . . H21B H -0.0860 0.8137 -0.0130 0.040 Uiso 1 1 calc R . . C20 C 0.10566(18) 0.84297(11) 0.08552(11) 0.0322(3) Uani 1 1 d . . . H20A H 0.1371 0.9265 0.0436 0.039 Uiso 1 1 calc R . . H20B H 0.0103 0.8409 0.1484 0.039 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 O8 0.0261(4) 0.0214(3) 0.0287(4) -0.0055(3) -0.0115(3) 0.0044(3) O3 0.0283(4) 0.0251(4) 0.0232(4) -0.0131(3) -0.0016(3) 0.0056(3) O4 0.0288(4) 0.0171(3) 0.0233(4) -0.0032(3) -0.0010(3) 0.0039(3) O2 0.0198(3) 0.0264(4) 0.0240(4) -0.0053(3) -0.0025(3) 0.0037(3) O1 0.0331(4) 0.0205(3) 0.0207(3) -0.0028(3) 0.0039(3) 0.0080(3) O7 0.0370(5) 0.0237(4) 0.0368(5) -0.0164(3) -0.0090(4) 0.0114(3) O5 0.0276(4) 0.0272(4) 0.0374(5) -0.0121(3) 0.0088(3) 0.0040(3) O9 0.0363(5) 0.0264(4) 0.0355(5) -0.0096(3) -0.0184(4) 0.0004(3) C1 0.0226(4) 0.0182(4) 0.0176(4) -0.0053(3) -0.0021(3) 0.0043(3) C11 0.0229(4) 0.0162(4) 0.0206(4) -0.0056(3) -0.0046(3) 0.0047(3) O6 0.0356(5) 0.0318(4) 0.0396(5) -0.0219(4) -0.0219(4) 0.0160(3) C5 0.0209(4) 0.0203(4) 0.0230(4) -0.0087(3) 0.0000(4) 0.0015(3) C16 0.0227(4) 0.0185(4) 0.0190(4) -0.0043(3) -0.0045(3) 0.0021(3) C4 0.0231(5) 0.0194(4) 0.0217(4) -0.0053(3) 0.0022(4) 0.0006(3) C6 0.0197(4) 0.0179(4) 0.0195(4) -0.0067(3) -0.0023(3) 0.0034(3) C19 0.0243(5) 0.0239(5) 0.0205(4) -0.0050(4) -0.0060(4) 0.0017(4) C3 0.0228(4) 0.0171(4) 0.0187(4) -0.0051(3) -0.0026(3) 0.0020(3) C12 0.0243(5) 0.0193(4) 0.0229(4) -0.0084(3) -0.0073(4) 0.0052(3) N1 0.0329(5) 0.0186(4) 0.0240(4) -0.0036(3) -0.0005(4) 0.0082(3) C14 0.0293(5) 0.0156(4) 0.0234(4) -0.0063(3) -0.0024(4) 0.0038(3) C13 0.0262(5) 0.0187(4) 0.0258(5) -0.0072(4) -0.0065(4) 0.0070(4) C9 0.0320(6) 0.0209(4) 0.0248(5) -0.0019(4) -0.0011(4) -0.0010(4) C15 0.0288(5) 0.0204(4) 0.0226(4) -0.0082(4) -0.0053(4) 0.0030(4) C10 0.0217(4) 0.0181(4) 0.0197(4) -0.0060(3) -0.0056(3) 0.0049(3) C2 0.0211(4) 0.0178(4) 0.0177(4) -0.0062(3) -0.0013(3) 0.0042(3) C18 0.0380(6) 0.0251(5) 0.0346(6) -0.0106(4) -0.0051(5) 0.0137(5) C7 0.0211(5) 0.0364(6) 0.0358(6) -0.0056(5) 0.0019(4) 0.0012(4) C17 0.0313(6) 0.0376(6) 0.0338(6) -0.0151(5) -0.0166(5) 0.0110(5) C8 0.0368(6) 0.0326(6) 0.0298(5) -0.0161(5) -0.0099(5) 0.0030(5) C22 0.0343(6) 0.0366(6) 0.0398(7) -0.0041(5) -0.0197(5) -0.0057(5) C21 0.0306(6) 0.0362(6) 0.0302(6) -0.0024(5) -0.0137(5) -0.0013(5) C20 0.0305(6) 0.0304(6) 0.0362(6) -0.0072(5) -0.0146(5) 0.0094(4) _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 O8 C19 1.4060(14) . ? O8 C20 1.4430(14) . ? O3 C2 1.4058(12) . ? O3 C8 1.4302(15) . ? O4 C3 1.3424(12) . ? O4 C9 1.4377(14) . ? O2 C2 1.3994(13) . ? O2 C7 1.4366(15) . ? O1 C1 1.3420(13) . ? O1 N1 1.4303(12) . ? O7 C14 1.3644(13) . ? O7 C18 1.4365(15) . ? O5 C5 1.2240(13) . ? O9 C19 1.4060(14) . ? O9 C22 1.4452(15) . ? C1 C6 1.3522(14) . ? C1 C2 1.5092(14) . ? C11 C12 1.3965(14) . ? C11 C16 1.4022(14) . ? C11 C10 1.4792(14) . ? O6 C12 1.3624(13) . ? O6 C17 1.4205(14) . ? C5 C6 1.4684(15) . ? C5 C4 1.4690(15) . ? C16 C15 1.3852(14) . ? C16 C19 1.5162(15) . ? C4 C3 1.3484(14) . ? C4 H4 0.9500 . ? C6 C10 1.4291(14) . ? C19 H19A 1.002(15) . ? C3 C2 1.5362(14) . ? C12 C13 1.3960(14) . ? N1 C10 1.3103(14) . ? C14 C13 1.3921(15) . ? C14 C15 1.3953(15) . ? C13 H13 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C15 H15 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C22 C21 1.5195(19) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C21 C20 1.5063(18) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 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 C19 O8 C20 110.77(9) . . ? C2 O3 C8 113.80(8) . . ? C3 O4 C9 116.64(9) . . ? C2 O2 C7 117.41(9) . . ? C1 O1 N1 107.38(8) . . ? C14 O7 C18 117.65(9) . . ? C19 O9 C22 110.22(10) . . ? O1 C1 C6 111.18(9) . . ? O1 C1 C2 121.48(9) . . ? C6 C1 C2 126.82(9) . . ? C12 C11 C16 119.15(9) . . ? C12 C11 C10 119.68(9) . . ? C16 C11 C10 121.17(9) . . ? C12 O6 C17 118.35(9) . . ? O5 C5 C6 122.94(10) . . ? O5 C5 C4 122.40(10) . . ? C6 C5 C4 114.64(9) . . ? C15 C16 C11 120.17(9) . . ? C15 C16 C19 120.72(9) . . ? C11 C16 C19 119.10(9) . . ? C3 C4 C5 123.10(10) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C1 C6 C10 104.11(9) . . ? C1 C6 C5 121.78(9) . . ? C10 C6 C5 134.02(9) . . ? O9 C19 O8 110.98(9) . . ? O9 C19 C16 110.25(9) . . ? O8 C19 C16 108.05(9) . . ? O9 C19 H19A 110.1(9) . . ? O8 C19 H19A 105.3(9) . . ? C16 C19 H19A 112.0(9) . . ? O4 C3 C4 125.81(10) . . ? O4 C3 C2 109.01(8) . . ? C4 C3 C2 125.15(9) . . ? O6 C12 C13 123.75(9) . . ? O6 C12 C11 115.03(9) . . ? C13 C12 C11 121.21(9) . . ? C10 N1 O1 106.06(8) . . ? O7 C14 C13 123.61(10) . . ? O7 C14 C15 115.32(10) . . ? C13 C14 C15 121.05(9) . . ? C14 C13 C12 118.51(10) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? O4 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C16 C15 C14 119.83(10) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N1 C10 C6 111.17(9) . . ? N1 C10 C11 119.31(9) . . ? C6 C10 C11 129.33(9) . . ? O2 C2 O3 108.35(8) . . ? O2 C2 C1 111.05(8) . . ? O3 C2 C1 112.38(8) . . ? O2 C2 C3 103.95(8) . . ? O3 C2 C3 112.82(8) . . ? C1 C2 C3 108.00(8) . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O9 C22 C21 111.33(10) . . ? O9 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? O9 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C20 C21 C22 109.46(10) . . ? C20 C21 H21A 109.8 . . ? C22 C21 H21A 109.8 . . ? C20 C21 H21B 109.8 . . ? C22 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? O8 C20 C21 109.07(10) . . ? O8 C20 H20A 109.9 . . ? C21 C20 H20A 109.9 . . ? O8 C20 H20B 109.9 . . ? C21 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? 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 N1 O1 C1 C6 -2.80(12) . . . . ? N1 O1 C1 C2 169.46(9) . . . . ? C12 C11 C16 C15 -0.73(16) . . . . ? C10 C11 C16 C15 179.74(10) . . . . ? C12 C11 C16 C19 178.57(10) . . . . ? C10 C11 C16 C19 -0.96(15) . . . . ? O5 C5 C4 C3 -176.85(11) . . . . ? C6 C5 C4 C3 1.70(15) . . . . ? O1 C1 C6 C10 3.24(12) . . . . ? C2 C1 C6 C10 -168.51(10) . . . . ? O1 C1 C6 C5 -179.81(9) . . . . ? C2 C1 C6 C5 8.44(17) . . . . ? O5 C5 C6 C1 174.12(11) . . . . ? C4 C5 C6 C1 -4.42(15) . . . . ? O5 C5 C6 C10 -10.00(19) . . . . ? C4 C5 C6 C10 171.46(11) . . . . ? C22 O9 C19 O8 -62.07(13) . . . . ? C22 O9 C19 C16 178.24(9) . . . . ? C20 O8 C19 O9 65.17(12) . . . . ? C20 O8 C19 C16 -173.84(9) . . . . ? C15 C16 C19 O9 -0.52(14) . . . . ? C11 C16 C19 O9 -179.81(9) . . . . ? C15 C16 C19 O8 -121.96(11) . . . . ? C11 C16 C19 O8 58.75(13) . . . . ? C9 O4 C3 C4 1.63(16) . . . . ? C9 O4 C3 C2 -176.48(9) . . . . ? C5 C4 C3 O4 179.63(10) . . . . ? C5 C4 C3 C2 -2.56(17) . . . . ? C17 O6 C12 C13 -8.21(18) . . . . ? C17 O6 C12 C11 172.88(11) . . . . ? C16 C11 C12 O6 -179.79(10) . . . . ? C10 C11 C12 O6 -0.25(15) . . . . ? C16 C11 C12 C13 1.27(16) . . . . ? C10 C11 C12 C13 -179.19(10) . . . . ? C1 O1 N1 C10 1.07(12) . . . . ? C18 O7 C14 C13 -6.16(17) . . . . ? C18 O7 C14 C15 172.68(10) . . . . ? O7 C14 C13 C12 176.12(10) . . . . ? C15 C14 C13 C12 -2.65(17) . . . . ? O6 C12 C13 C14 -178.44(11) . . . . ? C11 C12 C13 C14 0.40(17) . . . . ? C11 C16 C15 C14 -1.47(16) . . . . ? C19 C16 C15 C14 179.24(10) . . . . ? O7 C14 C15 C16 -175.66(10) . . . . ? C13 C14 C15 C16 3.21(17) . . . . ? O1 N1 C10 C6 0.94(12) . . . . ? O1 N1 C10 C11 -174.45(9) . . . . ? C1 C6 C10 N1 -2.56(12) . . . . ? C5 C6 C10 N1 -178.95(11) . . . . ? C1 C6 C10 C11 172.24(10) . . . . ? C5 C6 C10 C11 -4.15(19) . . . . ? C12 C11 C10 N1 -86.50(13) . . . . ? C16 C11 C10 N1 93.03(13) . . . . ? C12 C11 C10 C6 99.06(13) . . . . ? C16 C11 C10 C6 -81.40(15) . . . . ? C7 O2 C2 O3 -61.36(12) . . . . ? C7 O2 C2 C1 62.52(12) . . . . ? C7 O2 C2 C3 178.41(9) . . . . ? C8 O3 C2 O2 -170.32(9) . . . . ? C8 O3 C2 C1 66.60(12) . . . . ? C8 O3 C2 C3 -55.79(12) . . . . ? O1 C1 C2 O2 -65.66(12) . . . . ? C6 C1 C2 O2 105.31(12) . . . . ? O1 C1 C2 O3 55.88(13) . . . . ? C6 C1 C2 O3 -133.14(11) . . . . ? O1 C1 C2 C3 -179.03(9) . . . . ? C6 C1 C2 C3 -8.06(14) . . . . ? O4 C3 C2 O2 65.12(10) . . . . ? C4 C3 C2 O2 -113.01(11) . . . . ? O4 C3 C2 O3 -52.04(11) . . . . ? C4 C3 C2 O3 129.84(11) . . . . ? O4 C3 C2 C1 -176.86(8) . . . . ? C4 C3 C2 C1 5.02(14) . . . . ? C19 O9 C22 C21 55.39(15) . . . . ? O9 C22 C21 C20 -51.16(16) . . . . ? C19 O8 C20 C21 -59.76(13) . . . . ? C22 C21 C20 O8 52.41(15) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 32.09 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.445 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.053 # Attachment '- isoxazole_8i.CIF' data_shelxl_8i _database_code_depnum_ccdc_archive 'CCDC 859936' #TrackingRef '- isoxazole_8i.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O8' _chemical_formula_sum 'C21 H23 N O8' _chemical_formula_weight 417.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.467(6) _cell_length_b 9.266(3) _cell_length_c 15.337(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.767(16) _cell_angle_gamma 90.00 _cell_volume 2041.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19140 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9397 _exptl_absorpt_correction_T_max 0.9793 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19140 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4652 _reflns_number_gt 4017 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2002 (Burla, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4652 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.2092 _refine_ls_goodness_of_fit_ref 1.795 _refine_ls_restrained_S_all 1.795 _refine_ls_shift/su_max 0.001 _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 0.31229(9) 0.13060(14) 0.27973(7) 0.0236(3) Uani 1 1 d . . . O2 O 0.38697(9) 0.04181(14) 0.45815(9) 0.0285(3) Uani 1 1 d . . . O3 O 0.26208(9) -0.08769(13) 0.40142(7) 0.0246(3) Uani 1 1 d . . . O4 O 0.11119(10) 0.41353(16) 0.41428(9) 0.0329(4) Uani 1 1 d . . . O5 O 0.04937(9) 0.28149(14) 0.18805(9) 0.0282(3) Uani 1 1 d . . . O6 O 0.19984(11) 0.82426(15) 0.16530(10) 0.0379(4) Uani 1 1 d . . . O7 O 0.32859(10) 0.55186(15) 0.33195(8) 0.0292(3) Uani 1 1 d . . . O8 O 0.36832(10) 0.55323(16) 0.18926(9) 0.0352(4) Uani 1 1 d . . . N1 N 0.28033(11) 0.24359(16) 0.21936(9) 0.0225(3) Uani 1 1 d . . . C1 C 0.27098(11) 0.14877(18) 0.35228(10) 0.0189(4) Uani 1 1 d . . . C2 C 0.29046(12) 0.05042(18) 0.43010(10) 0.0209(4) Uani 1 1 d . . . C3 C 0.23762(14) 0.1052(2) 0.50313(11) 0.0260(4) Uani 1 1 d . . . H1 H 0.2451 0.0540 0.5572 0.031 Uiso 1 1 calc R . . C4 C 0.18146(13) 0.2196(2) 0.49720(11) 0.0258(4) Uani 1 1 d . . . H2 H 0.1513 0.2443 0.5469 0.031 Uiso 1 1 calc R . . C5 C 0.16340(12) 0.31043(19) 0.41758(11) 0.0223(4) Uani 1 1 d . . . C6 C 0.21463(11) 0.26478(18) 0.34549(10) 0.0181(4) Uani 1 1 d . . . C7 C 0.22316(11) 0.32134(17) 0.26030(10) 0.0177(3) Uani 1 1 d . . . C8 C 0.17216(12) 0.44529(18) 0.21611(10) 0.0190(4) Uani 1 1 d . . . C9 C 0.08018(12) 0.41955(19) 0.17992(10) 0.0214(4) Uani 1 1 d . . . C10 C 0.02770(13) 0.5306(2) 0.13832(12) 0.0279(4) Uani 1 1 d . . . H3 H -0.0346 0.5134 0.1135 0.033 Uiso 1 1 calc R . . C11 C 0.06653(14) 0.6667(2) 0.13307(12) 0.0297(4) Uani 1 1 d . . . H4 H 0.0305 0.7425 0.1046 0.036 Uiso 1 1 calc R . . C12 C 0.15745(14) 0.69321(19) 0.16904(11) 0.0258(4) Uani 1 1 d . . . C13 C 0.21122(12) 0.58198(19) 0.21135(10) 0.0210(4) Uani 1 1 d . . . C14 C 0.42757(17) 0.1694(3) 0.49750(18) 0.0484(6) Uani 1 1 d . . . H5 H 0.4497 0.2306 0.4522 0.058 Uiso 1 1 calc R . . H6 H 0.4801 0.1434 0.5410 0.058 Uiso 1 1 calc R . . H7 H 0.3809 0.2219 0.5265 0.058 Uiso 1 1 calc R . . C15 C 0.26182(15) -0.1947(2) 0.46880(13) 0.0309(4) Uani 1 1 d . . . H8 H 0.3227 -0.2421 0.4778 0.037 Uiso 1 1 calc R . . H9 H 0.2135 -0.2666 0.4511 0.037 Uiso 1 1 calc R . . H10 H 0.2490 -0.1485 0.5236 0.037 Uiso 1 1 calc R . . C16 C -0.04069(14) 0.2470(2) 0.14510(14) 0.0331(5) Uani 1 1 d . . . H11 H -0.0874 0.2645 0.1852 0.040 Uiso 1 1 calc R . . H12 H -0.0423 0.1452 0.1277 0.040 Uiso 1 1 calc R . . H13 H -0.0542 0.3077 0.0928 0.040 Uiso 1 1 calc R . . C17 C 0.1430(2) 0.9442(2) 0.1358(2) 0.0593(8) Uani 1 1 d . . . H14 H 0.1407 0.9529 0.0719 0.071 Uiso 1 1 calc R . . H15 H 0.1693 1.0326 0.1637 0.071 Uiso 1 1 calc R . . H16 H 0.0800 0.9295 0.1515 0.071 Uiso 1 1 calc R . . C18 C 0.31029(13) 0.61307(19) 0.24762(11) 0.0245(4) Uani 1 1 d . . . H17 H 0.3202 0.7198 0.2514 0.029 Uiso 1 1 calc R . . C19 C 0.42156(15) 0.5861(3) 0.36867(14) 0.0403(5) Uani 1 1 d . . . H18 H 0.4342 0.5437 0.4281 0.048 Uiso 1 1 calc R . . H19 H 0.4288 0.6921 0.3740 0.048 Uiso 1 1 calc R . . C20 C 0.49039(16) 0.5267(3) 0.31002(18) 0.0479(6) Uani 1 1 d . . . H20 H 0.5542 0.5588 0.3319 0.058 Uiso 1 1 calc R . . H21 H 0.4891 0.4199 0.3107 0.058 Uiso 1 1 calc R . . C21 C 0.46407(16) 0.5808(3) 0.21811(17) 0.0467(6) Uani 1 1 d . . . H22 H 0.4760 0.6859 0.2160 0.056 Uiso 1 1 calc R . . H23 H 0.5032 0.5326 0.1780 0.056 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 0.0255(7) 0.0258(7) 0.0203(6) 0.0035(5) 0.0052(5) 0.0079(5) O2 0.0238(7) 0.0277(7) 0.0315(7) 0.0021(5) -0.0069(5) 0.0052(5) O3 0.0336(7) 0.0192(6) 0.0205(6) 0.0002(5) 0.0006(5) 0.0004(5) O4 0.0370(8) 0.0326(8) 0.0307(7) 0.0038(6) 0.0100(6) 0.0151(6) O5 0.0229(7) 0.0250(7) 0.0349(7) 0.0048(5) -0.0043(5) -0.0050(5) O6 0.0503(10) 0.0175(7) 0.0437(8) 0.0052(6) -0.0035(7) -0.0035(6) O7 0.0271(7) 0.0372(8) 0.0219(6) -0.0006(5) -0.0025(5) -0.0074(6) O8 0.0276(8) 0.0487(9) 0.0307(7) -0.0072(6) 0.0096(6) -0.0091(6) N1 0.0263(8) 0.0229(8) 0.0188(7) 0.0050(5) 0.0046(5) 0.0046(6) C1 0.0177(8) 0.0219(8) 0.0169(7) -0.0005(6) 0.0012(5) 0.0007(6) C2 0.0225(9) 0.0205(9) 0.0189(8) 0.0011(6) -0.0011(6) 0.0027(6) C3 0.0357(10) 0.0277(9) 0.0147(8) 0.0027(6) 0.0030(6) 0.0037(7) C4 0.0345(10) 0.0276(9) 0.0163(8) 0.0002(7) 0.0075(6) 0.0030(7) C5 0.0227(8) 0.0235(9) 0.0213(8) -0.0001(6) 0.0043(6) 0.0030(6) C6 0.0169(8) 0.0208(8) 0.0160(7) -0.0002(6) -0.0001(5) 0.0001(6) C7 0.0170(7) 0.0180(8) 0.0178(7) -0.0002(6) 0.0004(5) -0.0026(6) C8 0.0221(9) 0.0201(8) 0.0148(7) 0.0007(6) 0.0021(6) 0.0016(6) C9 0.0217(9) 0.0224(9) 0.0200(8) 0.0017(6) 0.0015(6) 0.0006(6) C10 0.0231(9) 0.0318(10) 0.0275(9) 0.0058(7) -0.0021(7) 0.0039(7) C11 0.0341(10) 0.0265(10) 0.0280(9) 0.0052(7) 0.0017(7) 0.0096(8) C12 0.0360(10) 0.0201(9) 0.0214(8) 0.0013(7) 0.0046(7) 0.0001(7) C13 0.0246(9) 0.0207(8) 0.0179(7) -0.0013(6) 0.0033(6) -0.0013(6) C14 0.0342(12) 0.0359(12) 0.0689(16) -0.0047(11) -0.0205(11) -0.0023(9) C15 0.0408(11) 0.0227(9) 0.0291(9) 0.0044(7) 0.0042(8) 0.0000(8) C16 0.0248(10) 0.0363(11) 0.0362(10) 0.0007(8) -0.0043(7) -0.0090(8) C17 0.085(2) 0.0203(11) 0.0656(17) 0.0085(10) -0.0210(15) 0.0017(11) C18 0.0280(9) 0.0213(8) 0.0239(8) -0.0017(7) 0.0020(6) -0.0054(7) C19 0.0324(12) 0.0500(13) 0.0354(11) -0.0048(9) -0.0087(8) -0.0087(9) C20 0.0246(11) 0.0492(14) 0.0677(15) -0.0035(12) -0.0040(10) -0.0025(9) C21 0.0273(11) 0.0584(15) 0.0563(14) -0.0073(12) 0.0127(10) -0.0127(10) _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 1.334(2) . ? O1 N1 1.4375(18) . ? O2 C2 1.414(2) . ? O2 C14 1.422(3) . ? O3 C2 1.399(2) . ? O3 C15 1.432(2) . ? O4 C5 1.215(2) . ? O5 C9 1.365(2) . ? O5 C16 1.425(2) . ? O6 C12 1.365(2) . ? O6 C17 1.424(3) . ? O7 C18 1.408(2) . ? O7 C19 1.431(2) . ? O8 C18 1.411(2) . ? O8 C21 1.427(3) . ? N1 C7 1.311(2) . ? C1 C6 1.346(2) . ? C1 C2 1.502(2) . ? C2 C3 1.516(2) . ? C3 C4 1.332(3) . ? C4 C5 1.481(2) . ? C5 C6 1.464(2) . ? C6 C7 1.426(2) . ? C7 C8 1.485(2) . ? C8 C13 1.392(2) . ? C8 C9 1.400(2) . ? C9 C10 1.389(2) . ? C10 C11 1.386(3) . ? C11 C12 1.387(3) . ? C12 C13 1.403(3) . ? C13 C18 1.503(2) . ? C19 C20 1.521(4) . ? C20 C21 1.502(4) . ? 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 O1 N1 107.67(12) . . ? C2 O2 C14 115.21(14) . . ? C2 O3 C15 115.58(13) . . ? C9 O5 C16 117.28(14) . . ? C12 O6 C17 117.53(18) . . ? C18 O7 C19 109.76(15) . . ? C18 O8 C21 111.19(16) . . ? C7 N1 O1 105.36(13) . . ? O1 C1 C6 111.29(14) . . ? O1 C1 C2 121.71(15) . . ? C6 C1 C2 126.98(15) . . ? O3 C2 O2 106.66(13) . . ? O3 C2 C1 106.54(13) . . ? O2 C2 C1 111.24(14) . . ? O3 C2 C3 112.55(15) . . ? O2 C2 C3 111.09(14) . . ? C1 C2 C3 108.69(14) . . ? C4 C3 C2 124.91(15) . . ? C3 C4 C5 123.75(16) . . ? O4 C5 C6 124.27(16) . . ? O4 C5 C4 121.98(16) . . ? C6 C5 C4 113.75(15) . . ? C1 C6 C7 104.32(14) . . ? C1 C6 C5 121.89(15) . . ? C7 C6 C5 133.76(16) . . ? N1 C7 C6 111.36(15) . . ? N1 C7 C8 120.92(14) . . ? C6 C7 C8 127.61(15) . . ? C13 C8 C9 120.44(15) . . ? C13 C8 C7 123.00(15) . . ? C9 C8 C7 116.55(15) . . ? O5 C9 C10 124.73(16) . . ? O5 C9 C8 115.37(15) . . ? C10 C9 C8 119.89(17) . . ? C11 C10 C9 119.82(18) . . ? C10 C11 C12 120.65(17) . . ? O6 C12 C11 123.42(17) . . ? O6 C12 C13 116.46(17) . . ? C11 C12 C13 120.11(17) . . ? C8 C13 C12 119.08(16) . . ? C8 C13 C18 122.02(15) . . ? C12 C13 C18 118.87(16) . . ? O7 C18 O8 111.28(16) . . ? O7 C18 C13 109.30(14) . . ? O8 C18 C13 107.61(14) . . ? O7 C19 C20 109.71(17) . . ? C21 C20 C19 108.8(2) . . ? O8 C21 C20 111.16(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.629 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.067 data_shelxl_2a _database_code_depnum_ccdc_archive 'CCDC 874422' #TrackingRef '- Nitrileoxide_2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O5' _chemical_formula_sum 'C13 H15 N O5' _chemical_formula_weight 265.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4243(18) _cell_length_b 8.6769(16) _cell_length_c 9.1730(17) _cell_angle_alpha 108.968(5) _cell_angle_beta 103.816(6) _cell_angle_gamma 94.519(6) _cell_volume 606.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 169(2) _cell_measurement_reflns_used 6003 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9459 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 169(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6003 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2747 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2004 (Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0669P)^2^+0.0774P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2747 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.21767(11) 0.47909(10) 0.80480(9) 0.0261(2) Uani 1 1 d . . . O2 O 0.47281(13) 0.07639(13) 0.68033(13) 0.0427(3) Uani 1 1 d . . . O3 O 0.19262(10) 0.18386(9) 0.21324(10) 0.0246(2) Uani 1 1 d . . . O4 O 0.35792(10) 0.38830(9) 0.17587(9) 0.0249(2) Uani 1 1 d . . . O5 O 0.11045(11) 0.83170(10) 0.50253(10) 0.0268(2) Uani 1 1 d . . . N1 N 0.40652(12) 0.18183(12) 0.63553(12) 0.0262(2) Uani 1 1 d . . . C1 C 0.21714(13) 0.52257(13) 0.67471(13) 0.0205(2) Uani 1 1 d . . . C2 C 0.27910(13) 0.41315(13) 0.55833(13) 0.0197(2) Uani 1 1 d . . . C3 C 0.27965(13) 0.44429(13) 0.41848(12) 0.0193(2) Uani 1 1 d . . . C4 C 0.22792(13) 0.58588(13) 0.39727(13) 0.0207(2) Uani 1 1 d . . . H4 H 0.2330 0.6093 0.3041 0.025 Uiso 1 1 calc R . . C5 C 0.16857(13) 0.69311(13) 0.51416(13) 0.0206(2) Uani 1 1 d . . . C6 C 0.16147(13) 0.66121(13) 0.65243(13) 0.0216(2) Uani 1 1 d . . . H6 H 0.1189 0.7340 0.7303 0.026 Uiso 1 1 calc R . . C7 C 0.34407(14) 0.27652(14) 0.59073(13) 0.0236(2) Uani 1 1 d . . . C8 C 0.32777(13) 0.31736(13) 0.28623(12) 0.0199(2) Uani 1 1 d . . . H8 H 0.4296 0.2782 0.3330 0.024 Uiso 1 1 calc R . . C9 C 0.23099(15) 0.05354(14) 0.08879(14) 0.0278(3) Uani 1 1 d . . . H9A H 0.1356 -0.0386 0.0372 0.033 Uiso 1 1 calc R . . H9B H 0.3280 0.0107 0.1363 0.033 Uiso 1 1 calc R . . C10 C 0.26877(16) 0.11876(15) -0.03582(14) 0.0290(3) Uani 1 1 d . . . H10A H 0.3058 0.0325 -0.1153 0.035 Uiso 1 1 calc R . . H10B H 0.1677 0.1487 -0.0933 0.035 Uiso 1 1 calc R . . C11 C 0.40392(16) 0.26960(14) 0.04791(14) 0.0276(3) Uani 1 1 d . . . H11A H 0.5091 0.2363 0.0924 0.033 Uiso 1 1 calc R . . H11B H 0.4215 0.3205 -0.0304 0.033 Uiso 1 1 calc R . . C12 C 0.16613(16) 0.58999(15) 0.93175(14) 0.0285(3) Uani 1 1 d . . . H12A H 0.0514 0.6029 0.8903 0.034 Uiso 1 1 calc R . . H12B H 0.2386 0.6979 0.9740 0.034 Uiso 1 1 calc R . . H12C H 0.1731 0.5451 1.0178 0.034 Uiso 1 1 calc R . . C13 C 0.11895(16) 0.87260(14) 0.36513(15) 0.0290(3) Uani 1 1 d . . . H13A H 0.2346 0.8873 0.3624 0.035 Uiso 1 1 calc R . . H13B H 0.0755 0.9754 0.3716 0.035 Uiso 1 1 calc R . . H13C H 0.0526 0.7831 0.2673 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 0.0378(5) 0.0261(4) 0.0188(4) 0.0099(3) 0.0126(3) 0.0081(3) O2 0.0484(6) 0.0515(6) 0.0497(6) 0.0363(5) 0.0204(5) 0.0301(5) O3 0.0252(4) 0.0196(4) 0.0270(4) 0.0034(3) 0.0106(3) 0.0032(3) O4 0.0345(5) 0.0229(4) 0.0200(4) 0.0071(3) 0.0132(3) 0.0054(3) O5 0.0336(5) 0.0250(4) 0.0288(4) 0.0131(3) 0.0140(4) 0.0134(3) N1 0.0293(5) 0.0315(5) 0.0238(5) 0.0140(4) 0.0109(4) 0.0112(4) C1 0.0208(5) 0.0226(5) 0.0173(5) 0.0069(4) 0.0048(4) 0.0010(4) C2 0.0197(5) 0.0198(5) 0.0185(5) 0.0062(4) 0.0042(4) 0.0034(4) C3 0.0171(5) 0.0216(5) 0.0178(5) 0.0056(4) 0.0045(4) 0.0030(4) C4 0.0214(5) 0.0234(5) 0.0180(5) 0.0083(4) 0.0054(4) 0.0042(4) C5 0.0191(5) 0.0197(5) 0.0228(5) 0.0078(4) 0.0051(4) 0.0038(4) C6 0.0226(5) 0.0214(5) 0.0197(5) 0.0044(4) 0.0078(4) 0.0037(4) C7 0.0263(6) 0.0251(6) 0.0201(5) 0.0085(4) 0.0069(4) 0.0051(4) C8 0.0195(5) 0.0225(5) 0.0178(5) 0.0074(4) 0.0048(4) 0.0048(4) C9 0.0295(6) 0.0205(6) 0.0286(6) 0.0019(5) 0.0086(5) 0.0057(4) C10 0.0311(6) 0.0311(6) 0.0193(5) 0.0024(5) 0.0048(5) 0.0103(5) C11 0.0344(6) 0.0297(6) 0.0204(5) 0.0062(5) 0.0134(5) 0.0081(5) C12 0.0341(6) 0.0333(6) 0.0212(5) 0.0091(5) 0.0139(5) 0.0074(5) C13 0.0361(7) 0.0263(6) 0.0300(6) 0.0148(5) 0.0104(5) 0.0119(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3626(13) . ? O1 C12 1.4315(13) . ? O2 N1 1.2381(13) . ? O3 C8 1.4178(13) . ? O3 C9 1.4426(13) . ? O4 C8 1.4041(13) . ? O4 C11 1.4433(13) . ? O5 C5 1.3596(13) . ? O5 C13 1.4316(14) . ? N1 C7 1.1424(15) . ? C1 C6 1.3827(15) . ? C1 C2 1.4138(14) . ? C2 C3 1.3953(15) . ? C2 C7 1.4308(15) . ? C3 C4 1.3915(14) . ? C3 C8 1.5118(14) . ? C4 C5 1.3950(15) . ? C4 H4 0.9500 . ? C5 C6 1.3967(16) . ? C6 H6 0.9500 . ? C8 H8 1.0000 . ? C9 C10 1.5146(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5143(17) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 O1 C12 117.59(9) . . ? C8 O3 C9 110.00(8) . . ? C8 O4 C11 110.67(8) . . ? C5 O5 C13 117.29(8) . . ? C7 N1 O2 178.44(12) . . ? O1 C1 C6 124.68(10) . . ? O1 C1 C2 114.79(9) . . ? C6 C1 C2 120.53(10) . . ? C3 C2 C1 119.24(10) . . ? C3 C2 C7 122.18(10) . . ? C1 C2 C7 118.54(9) . . ? C4 C3 C2 120.46(9) . . ? C4 C3 C8 120.36(9) . . ? C2 C3 C8 119.08(9) . . ? C3 C4 C5 119.36(10) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O5 C5 C4 123.92(10) . . ? O5 C5 C6 115.00(9) . . ? C4 C5 C6 121.07(10) . . ? C1 C6 C5 119.26(10) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C2 171.24(12) . . ? O4 C8 O3 111.44(9) . . ? O4 C8 C3 109.47(8) . . ? O3 C8 C3 106.34(8) . . ? O4 C8 H8 109.8 . . ? O3 C8 H8 109.8 . . ? C3 C8 H8 109.8 . . ? O3 C9 C10 109.98(9) . . ? O3 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O3 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C9 108.79(9) . . ? C11 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? C11 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? O4 C11 C10 110.11(9) . . ? O4 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? O4 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.2 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C12 O1 C1 C6 -3.90(16) . . . . ? C12 O1 C1 C2 176.22(9) . . . . ? O1 C1 C2 C3 178.28(9) . . . . ? C6 C1 C2 C3 -1.60(16) . . . . ? O1 C1 C2 C7 -3.63(15) . . . . ? C6 C1 C2 C7 176.48(10) . . . . ? C1 C2 C3 C4 3.31(16) . . . . ? C7 C2 C3 C4 -174.70(10) . . . . ? C1 C2 C3 C8 -173.20(9) . . . . ? C7 C2 C3 C8 8.79(16) . . . . ? C2 C3 C4 C5 -2.76(16) . . . . ? C8 C3 C4 C5 173.70(9) . . . . ? C13 O5 C5 C4 -3.14(16) . . . . ? C13 O5 C5 C6 178.38(10) . . . . ? C3 C4 C5 O5 -177.91(10) . . . . ? C3 C4 C5 C6 0.48(16) . . . . ? O1 C1 C6 C5 179.50(10) . . . . ? C2 C1 C6 C5 -0.63(16) . . . . ? O5 C5 C6 C1 179.73(9) . . . . ? C4 C5 C6 C1 1.20(17) . . . . ? O2 N1 C7 C2 -171(4) . . . . ? C3 C2 C7 N1 131.6(7) . . . . ? C1 C2 C7 N1 -46.4(8) . . . . ? C11 O4 C8 O3 -62.55(11) . . . . ? C11 O4 C8 C3 -179.90(8) . . . . ? C9 O3 C8 O4 62.95(11) . . . . ? C9 O3 C8 C3 -177.82(8) . . . . ? C4 C3 C8 O4 17.28(13) . . . . ? C2 C3 C8 O4 -166.21(9) . . . . ? C4 C3 C8 O3 -103.24(11) . . . . ? C2 C3 C8 O3 73.27(12) . . . . ? C8 O3 C9 C10 -58.50(12) . . . . ? O3 C9 C10 C11 54.01(12) . . . . ? C8 O4 C11 C10 57.65(12) . . . . ? C9 C10 C11 O4 -53.31(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.235 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.077 # Attachment '- Nitrileoxide_2c.cif' data_shelxl_2c _database_code_depnum_ccdc_archive 'CCDC 874423' #TrackingRef '- Nitrileoxide_2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O5' _chemical_formula_sum 'C13 H15 N O5' _chemical_formula_weight 265.26 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 orthorohmbic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 13.0620(11) _cell_length_b 12.0982(8) _cell_length_c 16.2166(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2562.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 169(2) _cell_measurement_reflns_used 23309 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 0.9487 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 169(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23309 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2912 _reflns_number_gt 2304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2004 (Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0638P)^2^+0.5373P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2912 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1169 _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 -0.06556(8) 0.16977(10) 0.71797(7) 0.0492(3) Uani 1 1 d . . . O2 O 0.15926(12) 0.01815(13) 0.84921(8) 0.0709(4) Uani 1 1 d . . . O3 O 0.21718(8) -0.06721(8) 0.60222(8) 0.0474(3) Uani 1 1 d . . . O4 O 0.29643(7) 0.10216(8) 0.58227(7) 0.0420(3) Uani 1 1 d . . . O5 O 0.12580(10) 0.11434(10) 0.41709(7) 0.0541(3) Uani 1 1 d . . . N1 N 0.13277(10) 0.04342(10) 0.77843(8) 0.0416(3) Uani 1 1 d . . . C1 C -0.02666(11) 0.15798(11) 0.64036(9) 0.0369(3) Uani 1 1 d . . . C2 C 0.06846(10) 0.10289(10) 0.63579(8) 0.0312(3) Uani 1 1 d . . . C3 C 0.11812(11) 0.08752(10) 0.56009(8) 0.0324(3) Uani 1 1 d . . . C4 C 0.07170(12) 0.12879(11) 0.48870(9) 0.0377(3) Uani 1 1 d . . . C5 C -0.02319(12) 0.18027(11) 0.49318(10) 0.0434(4) Uani 1 1 d . . . H5 H -0.0551 0.2059 0.4441 0.052 Uiso 1 1 calc R . . C6 C -0.07205(11) 0.19473(12) 0.56849(11) 0.0425(4) Uani 1 1 d . . . H6 H -0.1370 0.2300 0.5706 0.051 Uiso 1 1 calc R . . C7 C 0.11199(10) 0.06565(11) 0.71211(9) 0.0352(3) Uani 1 1 d . . . C8 C 0.22000(11) 0.02966(11) 0.55417(9) 0.0348(3) Uani 1 1 d . . . H8 H 0.2338 0.0097 0.4954 0.042 Uiso 1 1 calc R . . C9 C 0.31196(13) -0.12697(13) 0.59442(13) 0.0548(5) Uani 1 1 d . . . H9A H 0.3212 -0.1508 0.5365 0.066 Uiso 1 1 calc R . . H9B H 0.3097 -0.1939 0.6295 0.066 Uiso 1 1 calc R . . C10 C 0.39976(12) -0.05629(13) 0.61975(11) 0.0464(4) Uani 1 1 d . . . H10A H 0.4650 -0.0948 0.6080 0.056 Uiso 1 1 calc R . . H10B H 0.3963 -0.0416 0.6797 0.056 Uiso 1 1 calc R . . C11 C 0.39577(12) 0.05120(14) 0.57292(14) 0.0567(5) Uani 1 1 d . . . H11A H 0.4494 0.1018 0.5939 0.068 Uiso 1 1 calc R . . H11B H 0.4094 0.0373 0.5138 0.068 Uiso 1 1 calc R . . C12 C -0.16096(14) 0.22694(17) 0.72534(13) 0.0637(5) Uani 1 1 d . . . H12A H -0.1547 0.3007 0.7008 0.076 Uiso 1 1 calc R . . H12B H -0.1791 0.2340 0.7837 0.076 Uiso 1 1 calc R . . H12C H -0.2145 0.1854 0.6965 0.076 Uiso 1 1 calc R . . C13 C 0.08504(17) 0.16026(17) 0.34375(11) 0.0630(5) Uani 1 1 d . . . H13A H 0.0151 0.1330 0.3355 0.076 Uiso 1 1 calc R . . H13B H 0.1277 0.1385 0.2968 0.076 Uiso 1 1 calc R . . H13C H 0.0840 0.2410 0.3483 0.076 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 0.0342(6) 0.0556(7) 0.0577(7) 0.0003(5) 0.0085(5) 0.0092(5) O2 0.0798(10) 0.0881(10) 0.0448(7) 0.0161(6) -0.0196(6) -0.0035(8) O3 0.0369(6) 0.0219(5) 0.0832(9) 0.0061(5) 0.0104(5) 0.0019(4) O4 0.0320(5) 0.0251(5) 0.0688(7) 0.0045(4) -0.0011(5) -0.0008(4) O5 0.0720(8) 0.0539(7) 0.0363(6) 0.0028(5) -0.0014(5) 0.0051(6) N1 0.0396(7) 0.0434(7) 0.0418(8) 0.0008(5) -0.0040(5) 0.0012(5) C1 0.0309(7) 0.0287(6) 0.0510(9) 0.0010(6) -0.0010(6) -0.0036(5) C2 0.0301(7) 0.0240(6) 0.0396(7) -0.0009(5) -0.0036(5) -0.0033(5) C3 0.0354(7) 0.0228(6) 0.0389(7) -0.0022(5) -0.0038(6) -0.0043(5) C4 0.0470(8) 0.0265(6) 0.0397(8) 0.0005(5) -0.0059(6) -0.0066(6) C5 0.0455(9) 0.0304(7) 0.0544(9) 0.0102(6) -0.0183(7) -0.0065(6) C6 0.0297(7) 0.0332(7) 0.0646(10) 0.0056(7) -0.0080(7) -0.0017(6) C7 0.0318(7) 0.0336(7) 0.0401(8) -0.0037(6) 0.0007(6) 0.0014(5) C8 0.0398(8) 0.0297(7) 0.0347(7) -0.0040(5) 0.0008(5) 0.0010(6) C9 0.0467(9) 0.0267(7) 0.0909(14) 0.0036(7) 0.0154(9) 0.0087(6) C10 0.0391(8) 0.0399(8) 0.0602(10) 0.0102(7) 0.0056(7) 0.0108(6) C11 0.0333(8) 0.0391(8) 0.0977(15) 0.0186(9) 0.0073(8) 0.0019(6) C12 0.0384(9) 0.0679(12) 0.0847(14) 0.0049(10) 0.0182(9) 0.0140(8) C13 0.0798(14) 0.0696(12) 0.0397(10) 0.0111(8) -0.0120(8) -0.0249(10) _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 1.3647(19) . ? O1 C12 1.4302(19) . ? O2 N1 1.2371(17) . ? O3 C8 1.4077(17) . ? O3 C9 1.4392(18) . ? O4 C8 1.4048(17) . ? O4 C11 1.4446(19) . ? O5 C4 1.3706(19) . ? O5 C13 1.416(2) . ? N1 C7 1.1415(18) . ? C1 C6 1.381(2) . ? C1 C2 1.4119(19) . ? C2 C3 1.4007(19) . ? C2 C7 1.435(2) . ? C3 C4 1.399(2) . ? C3 C8 1.5068(19) . ? C4 C5 1.389(2) . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 H8 1.0000 . ? C9 C10 1.488(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.507(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 O1 C12 116.87(13) . . ? C8 O3 C9 110.31(11) . . ? C8 O4 C11 109.74(11) . . ? C4 O5 C13 117.88(15) . . ? C7 N1 O2 177.37(16) . . ? O1 C1 C6 125.78(14) . . ? O1 C1 C2 115.18(12) . . ? C6 C1 C2 119.04(14) . . ? C3 C2 C1 121.08(13) . . ? C3 C2 C7 122.06(12) . . ? C1 C2 C7 116.85(12) . . ? C4 C3 C2 118.50(13) . . ? C4 C3 C8 119.73(13) . . ? C2 C3 C8 121.77(12) . . ? O5 C4 C5 124.16(14) . . ? O5 C4 C3 115.61(14) . . ? C5 C4 C3 120.23(14) . . ? C6 C5 C4 120.83(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 120.27(14) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N1 C7 C2 168.87(15) . . ? O4 C8 O3 111.03(12) . . ? O4 C8 C3 108.47(10) . . ? O3 C8 C3 109.17(11) . . ? O4 C8 H8 109.4 . . ? O3 C8 H8 109.4 . . ? C3 C8 H8 109.4 . . ? O3 C9 C10 110.48(12) . . ? O3 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O3 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 109.27(14) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? O4 C11 C10 110.27(13) . . ? O4 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? O4 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C12 O1 C1 C6 -1.1(2) . . . . ? C12 O1 C1 C2 178.90(13) . . . . ? O1 C1 C2 C3 -178.49(12) . . . . ? C6 C1 C2 C3 1.53(19) . . . . ? O1 C1 C2 C7 0.43(17) . . . . ? C6 C1 C2 C7 -179.55(12) . . . . ? C1 C2 C3 C4 0.46(18) . . . . ? C7 C2 C3 C4 -178.40(12) . . . . ? C1 C2 C3 C8 179.55(12) . . . . ? C7 C2 C3 C8 0.69(19) . . . . ? C13 O5 C4 C5 3.7(2) . . . . ? C13 O5 C4 C3 -176.41(13) . . . . ? C2 C3 C4 O5 177.88(11) . . . . ? C8 C3 C4 O5 -1.22(18) . . . . ? C2 C3 C4 C5 -2.22(19) . . . . ? C8 C3 C4 C5 178.68(12) . . . . ? O5 C4 C5 C6 -178.11(13) . . . . ? C3 C4 C5 C6 2.0(2) . . . . ? O1 C1 C6 C5 178.24(13) . . . . ? C2 C1 C6 C5 -1.8(2) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? O2 N1 C7 C2 -169(3) . . . . ? C3 C2 C7 N1 178.5(7) . . . . ? C1 C2 C7 N1 -0.4(8) . . . . ? C11 O4 C8 O3 63.29(16) . . . . ? C11 O4 C8 C3 -176.75(12) . . . . ? C9 O3 C8 O4 -63.28(16) . . . . ? C9 O3 C8 C3 177.18(13) . . . . ? C4 C3 C8 O4 103.79(14) . . . . ? C2 C3 C8 O4 -75.28(15) . . . . ? C4 C3 C8 O3 -135.09(13) . . . . ? C2 C3 C8 O3 45.83(16) . . . . ? C8 O3 C9 C10 57.87(19) . . . . ? O3 C9 C10 C11 -52.8(2) . . . . ? C8 O4 C11 C10 -58.00(19) . . . . ? C9 C10 C11 O4 53.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.211 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.039 # Attachment '- isoxazole_8g.CIF' data_shelxl_8g _database_code_depnum_ccdc_archive 'CCDC 874424' #TrackingRef '- isoxazole_8g.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H25 N O8' _chemical_formula_sum 'C22 H25 N O8' _chemical_formula_weight 431.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.573(6) _cell_length_b 8.394(5) _cell_length_c 18.258(12) _cell_angle_alpha 87.48(2) _cell_angle_beta 83.12(3) _cell_angle_gamma 69.44(3) _cell_volume 1078.9(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10631 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector System' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10631 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4874 _reflns_number_gt 3723 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SIR-2002 (Burla, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4874 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1636 _refine_ls_R_factor_gt 0.1503 _refine_ls_wR_factor_ref 0.4465 _refine_ls_wR_factor_gt 0.4440 _refine_ls_goodness_of_fit_ref 2.821 _refine_ls_restrained_S_all 2.821 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6825(7) -0.0226(5) 0.6418(2) 0.0372(10) Uani 1 1 d . . . O2 O 0.5670(7) -0.2283(5) 0.5465(2) 0.0405(11) Uani 1 1 d . . . O3 O 0.8427(7) -0.3952(5) 0.5849(2) 0.0416(11) Uani 1 1 d . . . O4 O 0.5047(6) -0.3070(5) 0.8402(2) 0.0371(10) Uani 1 1 d . . . O5 O 0.8937(6) -0.1379(5) 0.8454(2) 0.0386(10) Uani 1 1 d . . . O6 O 0.2435(6) 0.3671(5) 0.9644(2) 0.0392(10) Uani 1 1 d . . . O7 O 0.2252(6) 0.1012(5) 0.7942(2) 0.0397(10) Uani 1 1 d . . . O8 O 0.2527(7) 0.3680(5) 0.7790(3) 0.0426(11) Uani 1 1 d . . . N9 N 0.6636(8) 0.0760(6) 0.7069(2) 0.0349(11) Uani 1 1 d . . . C1 C 0.6443(8) -0.1620(7) 0.6633(3) 0.0292(11) Uani 1 1 d . . . C2 C 0.6537(9) -0.2973(7) 0.6094(3) 0.0320(12) Uani 1 1 d . . . C3 C 0.5736(9) -0.4256(7) 0.6497(3) 0.0323(12) Uani 1 1 d . . . C4 C 0.5258(9) -0.4231(7) 0.7219(3) 0.0348(12) Uani 1 1 d . . . H1 H 0.4789 -0.5084 0.7423 0.042 Uiso 1 1 calc R . . C5 C 0.5399(8) -0.2977(7) 0.7731(3) 0.0289(11) Uani 1 1 d . . . C6 C 0.5989(8) -0.1634(7) 0.7368(3) 0.0294(11) Uani 1 1 d . . . C7 C 0.6123(7) -0.0093(7) 0.7613(3) 0.0280(11) Uani 1 1 d . . . C8 C 0.5867(7) 0.0558(7) 0.8381(3) 0.0280(11) Uani 1 1 d . . . C9 C 0.7407(8) -0.0100(7) 0.8792(3) 0.0305(12) Uani 1 1 d . . . C10 C 0.7295(8) 0.0523(7) 0.9492(3) 0.0333(12) Uani 1 1 d . . . H2 H 0.8340 0.0072 0.9773 0.040 Uiso 1 1 calc R . . C11 C 0.5649(9) 0.1817(7) 0.9789(3) 0.0347(12) Uani 1 1 d . . . H3 H 0.5593 0.2262 1.0264 0.042 Uiso 1 1 calc R . . C12 C 0.4130(8) 0.2434(7) 0.9394(3) 0.0319(12) Uani 1 1 d . . . C13 C 0.4170(8) 0.1790(7) 0.8676(3) 0.0290(11) Uani 1 1 d . . . C14 C 0.2423(8) 0.2411(7) 0.8297(3) 0.0319(12) Uani 1 1 d . . . H4 H 0.1297 0.2893 0.8671 0.038 Uiso 1 1 calc R . . C15 C 0.0576(10) 0.1511(9) 0.7576(4) 0.0454(15) Uani 1 1 d . . . H5 H -0.0557 0.1930 0.7942 0.055 Uiso 1 1 calc R . . H6 H 0.0514 0.0517 0.7322 0.055 Uiso 1 1 calc R . . C16 C 0.0589(11) 0.2880(9) 0.7027(4) 0.0491(16) Uani 1 1 d . . . H7 H -0.0624 0.3293 0.6805 0.059 Uiso 1 1 calc R . . H8 H 0.1634 0.2423 0.6627 0.059 Uiso 1 1 calc R . . C17 C 0.0852(12) 0.4330(9) 0.7405(5) 0.0549(19) Uani 1 1 d . . . H9 H 0.0994 0.5188 0.7036 0.066 Uiso 1 1 calc R . . H10 H -0.0276 0.4886 0.7760 0.066 Uiso 1 1 calc R . . C18 C 0.3728(11) -0.1200(10) 0.5604(4) 0.0500(16) Uani 1 1 d . . . H11 H 0.2906 -0.1880 0.5609 0.060 Uiso 1 1 calc R . . H12 H 0.3424 -0.0333 0.5216 0.060 Uiso 1 1 calc R . . H13 H 0.3522 -0.0644 0.6084 0.060 Uiso 1 1 calc R . . C19 C 0.9532(13) -0.3051(10) 0.5454(5) 0.060(2) Uani 1 1 d . . . H14 H 0.9409 -0.3057 0.4926 0.072 Uiso 1 1 calc R . . H15 H 1.0868 -0.3605 0.5535 0.072 Uiso 1 1 calc R . . H16 H 0.9077 -0.1874 0.5630 0.072 Uiso 1 1 calc R . . C20 C 0.5560(12) -0.5592(8) 0.6009(3) 0.0467(17) Uani 1 1 d . . . H17 H 0.4310 -0.5176 0.5828 0.056 Uiso 1 1 calc R . . H18 H 0.5708 -0.6640 0.6293 0.056 Uiso 1 1 calc R . . H19 H 0.6550 -0.5824 0.5589 0.056 Uiso 1 1 calc R . . C21 C 1.0564(9) -0.2061(8) 0.8843(4) 0.0434(15) Uani 1 1 d . . . H20 H 1.1421 -0.1425 0.8710 0.052 Uiso 1 1 calc R . . H21 H 1.1221 -0.3261 0.8712 0.052 Uiso 1 1 calc R . . H22 H 1.0167 -0.1967 0.9375 0.052 Uiso 1 1 calc R . . C22 C 0.2377(9) 0.4451(8) 1.0328(3) 0.0391(14) Uani 1 1 d . . . H23 H 0.1963 0.3813 1.0734 0.047 Uiso 1 1 calc R . . H24 H 0.1482 0.5625 1.0331 0.047 Uiso 1 1 calc R . . H25 H 0.3644 0.4452 1.0389 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.048(3) 0.038(2) 0.0293(19) -0.0013(17) 0.0013(17) -0.0219(19) O2 0.051(3) 0.040(2) 0.035(2) 0.0064(18) -0.0124(18) -0.021(2) O3 0.040(2) 0.042(2) 0.039(2) -0.0058(19) 0.0068(18) -0.0132(19) O4 0.040(2) 0.048(2) 0.0286(19) 0.0048(17) -0.0031(16) -0.0229(19) O5 0.026(2) 0.039(2) 0.043(2) -0.0061(18) -0.0072(16) -0.0010(17) O6 0.030(2) 0.045(2) 0.035(2) -0.0082(19) -0.0049(16) -0.0021(18) O7 0.038(2) 0.034(2) 0.055(3) 0.0058(19) -0.0208(19) -0.0174(18) O8 0.041(2) 0.038(2) 0.057(3) 0.016(2) -0.023(2) -0.0203(19) N9 0.041(3) 0.034(2) 0.032(2) -0.007(2) -0.002(2) -0.017(2) C1 0.030(3) 0.032(2) 0.031(2) 0.003(2) -0.006(2) -0.016(2) C2 0.039(3) 0.032(3) 0.031(3) -0.001(2) -0.002(2) -0.020(2) C3 0.039(3) 0.028(2) 0.035(3) 0.000(2) -0.007(2) -0.017(2) C4 0.038(3) 0.035(3) 0.037(3) 0.002(2) -0.009(2) -0.017(2) C5 0.026(3) 0.036(3) 0.027(2) 0.001(2) -0.0029(19) -0.013(2) C6 0.025(2) 0.032(3) 0.031(3) -0.001(2) -0.002(2) -0.009(2) C7 0.022(2) 0.032(2) 0.030(2) 0.004(2) -0.0057(19) -0.009(2) C8 0.022(2) 0.032(2) 0.032(3) -0.003(2) -0.0026(19) -0.011(2) C9 0.025(3) 0.027(2) 0.038(3) -0.002(2) -0.001(2) -0.009(2) C10 0.028(3) 0.037(3) 0.038(3) 0.001(2) -0.010(2) -0.014(2) C11 0.036(3) 0.038(3) 0.031(3) -0.002(2) -0.008(2) -0.012(2) C12 0.026(3) 0.031(3) 0.036(3) -0.007(2) -0.001(2) -0.007(2) C13 0.026(3) 0.031(2) 0.032(3) 0.001(2) -0.004(2) -0.012(2) C14 0.026(3) 0.036(3) 0.033(3) -0.002(2) -0.004(2) -0.010(2) C15 0.034(3) 0.048(3) 0.063(4) 0.002(3) -0.017(3) -0.020(3) C16 0.041(4) 0.061(4) 0.045(3) 0.009(3) -0.024(3) -0.012(3) C17 0.053(4) 0.047(3) 0.069(5) 0.020(3) -0.035(4) -0.017(3) C18 0.043(4) 0.058(4) 0.052(4) 0.010(3) -0.018(3) -0.018(3) C19 0.057(5) 0.063(4) 0.064(5) -0.016(4) 0.024(4) -0.033(4) C20 0.074(5) 0.042(3) 0.035(3) -0.004(3) -0.008(3) -0.033(3) C21 0.026(3) 0.044(3) 0.058(4) 0.000(3) -0.013(3) -0.007(2) C22 0.028(3) 0.047(3) 0.038(3) -0.014(3) -0.001(2) -0.007(2) _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 1.333(7) . ? O1 N9 1.443(6) . ? O2 C2 1.394(7) . ? O2 C18 1.430(9) . ? O3 C2 1.406(7) . ? O3 C19 1.431(8) . ? O4 C5 1.227(6) . ? O5 C9 1.375(6) . ? O5 C21 1.424(8) . ? O6 C12 1.378(6) . ? O6 C22 1.424(7) . ? O7 C14 1.418(7) . ? O7 C15 1.427(8) . ? O8 C14 1.397(7) . ? O8 C17 1.447(8) . ? N9 C7 1.301(7) . ? C1 C6 1.346(7) . ? C1 C2 1.513(7) . ? C2 C3 1.533(7) . ? C3 C4 1.322(8) . ? C3 C20 1.514(7) . ? C4 C5 1.477(7) . ? C5 C6 1.459(8) . ? C6 C7 1.427(8) . ? C7 C8 1.493(7) . ? C8 C9 1.396(8) . ? C8 C13 1.400(7) . ? C9 C10 1.383(8) . ? C10 C11 1.402(8) . ? C11 C12 1.364(9) . ? C12 C13 1.433(7) . ? C13 C14 1.485(8) . ? C15 C16 1.493(10) . ? C16 C17 1.509(10) . ? 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 O1 N9 107.6(4) . . ? C2 O2 C18 114.7(5) . . ? C2 O3 C19 116.0(5) . . ? C9 O5 C21 117.2(5) . . ? C12 O6 C22 116.4(4) . . ? C14 O7 C15 111.5(4) . . ? C14 O8 C17 111.8(5) . . ? C7 N9 O1 105.3(4) . . ? O1 C1 C6 111.3(5) . . ? O1 C1 C2 122.3(4) . . ? C6 C1 C2 126.4(5) . . ? O2 C2 O3 106.4(4) . . ? O2 C2 C1 112.4(5) . . ? O3 C2 C1 111.2(5) . . ? O2 C2 C3 113.4(5) . . ? O3 C2 C3 104.1(4) . . ? C1 C2 C3 109.1(4) . . ? C4 C3 C20 121.9(5) . . ? C4 C3 C2 123.2(5) . . ? C20 C3 C2 114.9(5) . . ? C3 C4 C5 125.0(5) . . ? O4 C5 C6 123.4(5) . . ? O4 C5 C4 122.5(5) . . ? C6 C5 C4 114.1(5) . . ? C1 C6 C7 104.1(5) . . ? C1 C6 C5 121.6(5) . . ? C7 C6 C5 134.1(5) . . ? N9 C7 C6 111.8(4) . . ? N9 C7 C8 119.0(5) . . ? C6 C7 C8 129.1(5) . . ? C9 C8 C13 121.2(5) . . ? C9 C8 C7 117.0(4) . . ? C13 C8 C7 121.8(5) . . ? O5 C9 C10 125.1(5) . . ? O5 C9 C8 115.1(5) . . ? C10 C9 C8 119.8(5) . . ? C9 C10 C11 120.4(5) . . ? C12 C11 C10 119.8(5) . . ? C11 C12 O6 124.2(5) . . ? C11 C12 C13 121.5(5) . . ? O6 C12 C13 114.3(5) . . ? C8 C13 C12 117.2(5) . . ? C8 C13 C14 123.7(5) . . ? C12 C13 C14 119.0(5) . . ? O8 C14 O7 111.2(4) . . ? O8 C14 C13 109.6(5) . . ? O7 C14 C13 108.4(4) . . ? O7 C15 C16 110.0(5) . . ? C15 C16 C17 109.5(5) . . ? O8 C17 C16 109.3(5) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.535 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.123