Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts.
Hashimoto, Yoshimitsu; Takada, Akiomi; Takikawa, Hiroshi; Suzuki, Keisuke; Organic & biomolecular chemistry 10 (2012) 6003–6009; doi:10.1039/c2ob25423a

data_7152490
_publ_section_title
;
 Synthesis of isoxazoles en route to semi-aromatized polyketides:
 dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6003
_journal_page_last               6009
_journal_paper_doi               10.1039/c2ob25423a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C22 H25 N O9'
_chemical_formula_sum            'C22 H25 N O9'
_chemical_formula_weight         447.43
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.852(10)
_cell_angle_beta                 83.715(8)
_cell_angle_gamma                89.902(11)
_cell_formula_units_Z            2
_cell_length_a                   7.3141(14)
_cell_length_b                   11.871(3)
_cell_length_c                   12.579(2)
_cell_measurement_reflns_used    6823
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.09
_cell_measurement_theta_min      1.80
_cell_volume                     1036.8(4)
_computing_cell_refinement       'DENZO HKL2000 (W.Minor)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'DENZO HKL2000 (W.Minor)'
_computing_molecular_graphics    'ORTEP-3 for windows(Farrugia,1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area detector system'
_diffrn_measurement_method       \wscan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13525
_diffrn_reflns_theta_full        32.09
_diffrn_reflns_theta_max         32.09
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SCALEPACK
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flatplate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0591P)^2^+0.3668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                5888
_reflns_number_total             6823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25423a.txt
_cod_data_source_block           s1
_cod_database_code               7152490