The synthesis of the pyranonaphthoquinones dehydroherbarin and anhydrofusarubin using Wacker oxidation methodology as a key step and other unexpected oxidation reactions with ceric ammonium nitrate and salcomine.
Pillay, Adushan; Rousseau, Amanda L.; Fernandes, Manuel A.; de Koning, Charles B.; Organic & biomolecular chemistry 10 (2012) 7809–7819; doi:10.1039/c2ob26126j

data_7152648
_publ_section_title
;
 The synthesis of the pyranonaphthoquinones dehydroherbarin and
 anhydrofusarubin using Wacker oxidation methodology as a key step and
 other unexpected oxidation reactions with ceric ammonium nitrate and
 salcomine.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7809
_journal_page_last               7819
_journal_paper_doi               10.1039/c2ob26126j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C16 H15 N O9'
_chemical_formula_sum            'C16 H15 N O9'
_chemical_formula_weight         365.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.246(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.913(4)
_cell_length_b                   13.475(4)
_cell_length_c                   8.404(3)
_cell_measurement_reflns_used    925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.94
_cell_volume                     1571.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.1022
_diffrn_reflns_av_sigmaI/netI    0.1561
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7954
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.1857
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0354P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1010
_reflns_number_total             2722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26126j.txt
_cod_data_source_block           11m_cdk_adushan4_0s-cmpd17
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152648