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_7152788
_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         'C24 H13 Br O3'
_chemical_formula_sum            'C24 H13 Br O3'
_chemical_formula_weight         429.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                112.907(2)
_cell_angle_beta                 101.682(2)
_cell_angle_gamma                94.195(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8383(3)
_cell_length_b                   10.9083(4)
_cell_length_c                   12.0674(6)
_cell_measurement_reflns_used    4631
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     917.43(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_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      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5114
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.263
_exptl_absorpt_correction_T_max  0.4963
_exptl_absorpt_correction_T_min  0.2852
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0589
_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^)+(0.1109P)^2^+0.4722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                2015
_reflns_number_total             3094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26986d.txt
_cod_data_source_block           11631
_cod_database_code               7152788