Total synthesis of siphonazole and its O-methyl derivative, structurally unusual bis-oxazole natural products
Linder, Jörg; Blake, Alexander J.; Moody, Christopher J.; Organic & Biomolecular Chemistry 6 (2008) 3908–3916; doi:10.1039/b810855b

data_7151009
_publ_section_title
;
 Total synthesis of siphonazole and its O-methyl derivative,
 structurally unusual bis-oxazole natural products
;
_journal_issue                   21
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3908
_journal_page_last               3916
_journal_paper_doi               10.1039/b810855b
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens
'sp2 methyl H atoms from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.634(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3420(10)
_cell_length_b                   5.8896(7)
_cell_length_c                   26.712(3)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.55
_cell_volume                     1312.3(3)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker,2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker,2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL(Bruker, 2001)'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8828
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    'rigid rotor; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.078P)^2^+0.063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.117
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                2520
_reflns_number_total             2986
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b810855b.txt
_cod_data_source_block           dimoxz
_cod_original_cell_volume        1312.3(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151009