An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones.
Meck, Christine; Mohd, Noushad; Murelli, Ryan P.; Organic letters 14 (2012) 5988–5991; doi:10.1021/ol302892g

data_1556127
_publ_section_title
;
 An oxidopyrylium cyclization/ring-opening route to polysubstituted
 \a-hydroxytropolones.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5988
_journal_page_last               5991
_journal_paper_doi               10.1021/ol302892g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H12 O7'
_chemical_formula_sum            'C12 H12 O7'
_chemical_formula_weight         268.22
_chemical_name_common            brkrm02
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                91.356(2)
_cell_angle_beta                 108.391(2)
_cell_angle_gamma                92.720(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8732(9)
_cell_length_b                   7.9554(9)
_cell_length_c                   9.7428(11)
_cell_measurement_reflns_used    4059
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      37.29
_cell_measurement_theta_min      2.20
_cell_volume                     577.93(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13373
_diffrn_reflns_theta_full        33.73
_diffrn_reflns_theta_max         33.73
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.1212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                3397
_reflns_number_total             4580
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302892g_si_001.cif
_cod_data_source_block           brkrm02
_cod_database_code               1556127