# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Christopher Moody' 'Alexander J. Blake' 'Jorg Linder' _publ_contact_author_name 'Christopher Moody' _publ_contact_author_email C.J.MOODY@NOTTINGHAM.AC.UK _publ_section_title ; Total synthesis of siphonazole and its O-methyl derivative, structurally unusual bis-oxazole natural products ; data_dimoxz _database_code_depnum_ccdc_archive 'CCDC 693019' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N O4' _chemical_formula_sum 'C15 H15 N O4' _chemical_formula_weight 273.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M '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 8.3420(10) _cell_length_b 5.8896(7) _cell_length_c 26.712(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.634(2) _cell_angle_gamma 90.00 _cell_volume 1312.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2182 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.3 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8828 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2986 _reflns_number_gt 2520 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker,2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker,2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL(Bruker, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; ; _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^)+(0.078P)^2^+0.063P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens ;sp2 methyl H atoms from delta-F; others placed geometrically ; _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2986 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.122 _refine_ls_wR_factor_gt 0.117 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 0.18910(10) 0.98414(15) -0.08847(3) 0.0294(2) Uani 1 1 d . . . C2 C 0.19471(15) 1.0573(2) -0.03967(5) 0.0295(3) Uani 1 1 d . . . N3 N 0.11851(13) 1.24483(19) -0.03244(4) 0.0324(3) Uani 1 1 d . . . C4 C 0.05730(15) 1.3024(2) -0.07956(4) 0.0283(3) Uani 1 1 d . . . C5 C 0.10060(14) 1.1438(2) -0.11354(5) 0.0268(3) Uani 1 1 d . . . C6 C 0.28215(15) 0.9153(2) -0.00399(5) 0.0323(3) Uani 1 1 d . . . H6 H 0.3299 0.7773 -0.0146 0.039 Uiso 1 1 calc R . . C7 C 0.29476(15) 0.9827(2) 0.04495(5) 0.0313(3) Uani 1 1 d . . . H7 H 0.2465 1.1227 0.0540 0.038 Uiso 1 1 calc R . . C8 C 0.37803(14) 0.8529(2) 0.08459(4) 0.0266(3) Uani 1 1 d . . . C9 C 0.36646(14) 0.9315(2) 0.13407(4) 0.0244(3) Uani 1 1 d . . . H9 H 0.3064 1.0649 0.1408 0.029 Uiso 1 1 calc R . . C10 C 0.44114(13) 0.8175(2) 0.17301(4) 0.0227(3) Uani 1 1 d . . . C11 C 0.53281(14) 0.62189(19) 0.16314(4) 0.0233(3) Uani 1 1 d . . . C12 C 0.54404(15) 0.5437(2) 0.11448(5) 0.0277(3) Uani 1 1 d . . . H12 H 0.6049 0.4112 0.1076 0.033 Uiso 1 1 calc R . . C13 C 0.46670(16) 0.6581(2) 0.07557(5) 0.0308(3) Uani 1 1 d . . . H13 H 0.4747 0.6020 0.0423 0.037 Uiso 1 1 calc R . . C14 C 0.07237(16) 1.1129(2) -0.16756(5) 0.0335(3) Uani 1 1 d . . . H14A H 0.1738 1.1298 -0.1853 0.050 Uiso 1 1 calc R . . H14B H -0.0041 1.2275 -0.1796 0.050 Uiso 1 1 calc R . . H14C H 0.0286 0.9610 -0.1737 0.050 Uiso 1 1 calc R . . C15 C -0.03994(17) 1.5071(2) -0.08629(5) 0.0346(3) Uani 1 1 d . . . H15 H -0.0673 1.5903 -0.0571 0.042 Uiso 1 1 calc R . . O16 O -0.08837(12) 1.57899(16) -0.12633(4) 0.0376(3) Uani 1 1 d . . . O17 O 0.43622(10) 0.87913(14) 0.22224(3) 0.0278(2) Uani 1 1 d . . . C18 C 0.33451(15) 1.0655(2) 0.23476(5) 0.0299(3) Uani 1 1 d . . . H18A H 0.3415 1.0941 0.2709 0.045 Uiso 1 1 calc R . . H18B H 0.2235 1.0290 0.2254 0.045 Uiso 1 1 calc R . . H18C H 0.3688 1.2013 0.2166 0.045 Uiso 1 1 calc R . . O19 O 0.60578(10) 0.52625(15) 0.20399(3) 0.0280(2) Uani 1 1 d . . . C20 C 0.71230(15) 0.3416(2) 0.19451(5) 0.0297(3) Uani 1 1 d . . . H20A H 0.7574 0.2862 0.2263 0.045 Uiso 1 1 calc R . . H20B H 0.7993 0.3934 0.1729 0.045 Uiso 1 1 calc R . . H20C H 0.6534 0.2186 0.1778 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0333(5) 0.0316(5) 0.0232(5) 0.0016(4) -0.0054(4) 0.0078(4) C2 0.0294(6) 0.0373(7) 0.0219(6) 0.0034(5) -0.0004(5) 0.0040(5) N3 0.0362(6) 0.0384(6) 0.0227(5) 0.0025(4) 0.0010(4) 0.0091(5) C4 0.0276(6) 0.0339(6) 0.0233(6) 0.0037(5) 0.0006(5) 0.0047(5) C5 0.0250(6) 0.0295(6) 0.0259(6) 0.0043(5) -0.0031(5) 0.0034(5) C6 0.0325(7) 0.0396(7) 0.0247(6) 0.0052(5) -0.0030(5) 0.0082(6) C7 0.0307(7) 0.0381(7) 0.0252(6) 0.0037(5) -0.0008(5) 0.0064(5) C8 0.0264(6) 0.0318(6) 0.0214(6) 0.0023(5) -0.0014(4) 0.0016(5) C9 0.0240(6) 0.0250(6) 0.0242(6) 0.0007(5) -0.0004(5) 0.0024(4) C10 0.0230(6) 0.0254(6) 0.0198(5) -0.0018(4) -0.0004(4) -0.0030(4) C11 0.0232(6) 0.0259(6) 0.0208(6) 0.0026(4) -0.0029(4) -0.0009(4) C12 0.0309(6) 0.0278(6) 0.0241(6) -0.0023(5) -0.0011(5) 0.0064(5) C13 0.0367(7) 0.0364(7) 0.0191(6) -0.0023(5) -0.0013(5) 0.0060(5) C14 0.0402(7) 0.0329(7) 0.0271(6) -0.0003(5) -0.0107(5) 0.0078(5) C15 0.0383(7) 0.0352(7) 0.0304(7) 0.0029(6) 0.0042(5) 0.0111(6) O16 0.0406(6) 0.0376(5) 0.0344(5) 0.0081(4) -0.0004(4) 0.0102(4) O17 0.0320(5) 0.0306(5) 0.0207(4) -0.0050(3) -0.0033(3) 0.0046(3) C18 0.0314(7) 0.0308(6) 0.0276(6) -0.0085(5) 0.0010(5) 0.0012(5) O19 0.0329(5) 0.0306(5) 0.0205(4) 0.0016(3) -0.0035(3) 0.0077(3) C20 0.0325(7) 0.0298(6) 0.0268(6) 0.0029(5) -0.0028(5) 0.0072(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 C5 1.3665(14) . ? O1 C2 1.3732(15) . ? C2 N3 1.2898(16) . ? C2 C6 1.4576(17) . ? N3 C4 1.3949(16) . ? C4 C5 1.3542(18) . ? C4 C15 1.4634(17) . ? C5 C14 1.4706(17) . ? C6 C7 1.3691(19) . ? C6 H6 0.9500 . ? C7 C8 1.4738(17) . ? C7 H7 0.9500 . ? C8 C13 1.3876(17) . ? C8 C9 1.4045(17) . ? C9 C10 1.3807(16) . ? C9 H9 0.9500 . ? C10 O17 1.3653(14) . ? C10 C11 1.4092(16) . ? C11 O19 1.3653(14) . ? C11 C12 1.3830(17) . ? C12 C13 1.3912(17) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O16 1.2153(16) . ? C15 H15 0.9500 . ? O17 C18 1.4294(14) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O19 C20 1.4287(14) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C5 O1 C2 105.18(9) . . ? N3 C2 O1 113.53(11) . . ? N3 C2 C6 129.59(12) . . ? O1 C2 C6 116.87(11) . . ? C2 N3 C4 104.42(10) . . ? C5 C4 N3 109.86(11) . . ? C5 C4 C15 129.61(12) . . ? N3 C4 C15 120.53(11) . . ? C4 C5 O1 107.02(11) . . ? C4 C5 C14 134.58(12) . . ? O1 C5 C14 118.40(11) . . ? C7 C6 C2 119.38(12) . . ? C7 C6 H6 120.3 . . ? C2 C6 H6 120.3 . . ? C6 C7 C8 124.50(12) . . ? C6 C7 H7 117.8 . . ? C8 C7 H7 117.8 . . ? C13 C8 C9 118.57(11) . . ? C13 C8 C7 123.50(11) . . ? C9 C8 C7 117.93(11) . . ? C10 C9 C8 120.90(11) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? O17 C10 C9 125.33(11) . . ? O17 C10 C11 114.81(10) . . ? C9 C10 C11 119.85(11) . . ? O19 C11 C12 125.42(11) . . ? O19 C11 C10 115.20(10) . . ? C12 C11 C10 119.37(11) . . ? C11 C12 C13 120.35(12) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 120.94(11) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C5 C14 H14A 109.5 . . ? C5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O16 C15 C4 124.99(13) . . ? O16 C15 H15 117.5 . . ? C4 C15 H15 117.5 . . ? C10 O17 C18 116.99(9) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C11 O19 C20 116.42(9) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C5 O1 C2 N3 0.13(14) . . . . ? C5 O1 C2 C6 179.53(11) . . . . ? O1 C2 N3 C4 -0.04(15) . . . . ? C6 C2 N3 C4 -179.35(14) . . . . ? C2 N3 C4 C5 -0.07(15) . . . . ? C2 N3 C4 C15 179.11(12) . . . . ? N3 C4 C5 O1 0.15(14) . . . . ? C15 C4 C5 O1 -178.94(12) . . . . ? N3 C4 C5 C14 179.85(13) . . . . ? C15 C4 C5 C14 0.8(3) . . . . ? C2 O1 C5 C4 -0.16(13) . . . . ? C2 O1 C5 C14 -179.92(11) . . . . ? N3 C2 C6 C7 -2.2(2) . . . . ? O1 C2 C6 C7 178.52(12) . . . . ? C2 C6 C7 C8 179.19(12) . . . . ? C6 C7 C8 C13 6.6(2) . . . . ? C6 C7 C8 C9 -173.36(12) . . . . ? C13 C8 C9 C10 -0.19(18) . . . . ? C7 C8 C9 C10 179.79(11) . . . . ? C8 C9 C10 O17 -179.54(10) . . . . ? C8 C9 C10 C11 1.17(18) . . . . ? O17 C10 C11 O19 -1.38(15) . . . . ? C9 C10 C11 O19 177.98(10) . . . . ? O17 C10 C11 C12 179.30(11) . . . . ? C9 C10 C11 C12 -1.34(17) . . . . ? O19 C11 C12 C13 -178.70(11) . . . . ? C10 C11 C12 C13 0.53(19) . . . . ? C9 C8 C13 C12 -0.63(19) . . . . ? C7 C8 C13 C12 179.39(12) . . . . ? C11 C12 C13 C8 0.5(2) . . . . ? C5 C4 C15 O16 -6.5(2) . . . . ? N3 C4 C15 O16 174.45(13) . . . . ? C9 C10 O17 C18 5.56(17) . . . . ? C11 C10 O17 C18 -175.12(10) . . . . ? C12 C11 O19 C20 5.34(17) . . . . ? C10 C11 O19 C20 -173.92(10) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.30 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.06 #===END of CIF