Unique reactivity of anti- and syn-acetoxypyranones en route to oxidopyrylium intermediates leading to a cascade process.
Woodall, Erica L.; Simanis, Justin A.; Hamaker, Christopher G.; Goodell, John R.; Mitchell, T. Andrew; Organic letters 15 (2013) 3270–3273; doi:10.1021/ol4012986

data_1556185
_publ_section_title
;
 Unique reactivity of anti- and syn-acetoxypyranones en route to
 oxidopyrylium intermediates leading to a cascade process.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3270
_journal_page_last               3273
_journal_paper_doi               10.1021/ol4012986
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H17 Br1 O4'
_chemical_formula_sum            'C17 H17 Br O4'
_chemical_formula_weight         365.22
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2013-03-12T15:59:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                78.9278(17)
_cell_angle_beta                 79.0335(19)
_cell_angle_gamma                82.9068(19)
_cell_formula_units_Z            2
_cell_length_a                   6.1044(2)
_cell_length_b                   9.3857(3)
_cell_length_c                   14.7205(5)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0682
_cell_measurement_theta_min      2.4244
_cell_measurement_wavelength     0.71073
_cell_volume                     809.27(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20167
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    2.554
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0280P)^2^+1.2357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                2959
_reflns_number_total             3204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4012986_si_003.cif
_cod_data_source_block           ch63
_cod_database_code               1556185