A versatile and practical method for regioselective synthesis of polysubstituted furanonaphthoquinones.
Wu, Zong-Ze; Jang, Yeong-Jiunn; Lee, Chia-Jui; Lee, Yen-Te; Lin, Wenwei; Organic & biomolecular chemistry 11 (2013) 828–834; doi:10.1039/c2ob26986d

data_7152787
_publ_section_title
;
 A versatile and practical method for regioselective synthesis of
 polysubstituted furanonaphthoquinones.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              828
_journal_page_last               834
_journal_paper_doi               10.1039/c2ob26986d
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C29 H36 Br O3 P'
_chemical_formula_sum            'C29 H36 Br O3 P'
_chemical_formula_weight         543.46
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.554(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.116(4)
_cell_length_b                   12.7605(19)
_cell_length_c                   21.907(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     5877.6(16)
_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    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1298
_diffrn_reflns_av_sigmaI/netI    0.1448
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17718
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                2369
_reflns_number_total             5221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26986d.txt
_cod_data_source_block           a11571a
_cod_original_cell_volume        5877.5(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7152787