Synthesis of Balsaminone A, a Naturally Occurring Pentacyclic Dinaphthofuran Quinone
Jalindar Padwal; William Lewis; Christopher J. Moody; Journal of Organic Chemistry 76 (2011) 8082–8087; doi:10.1021/jo201395n

data_4026625
_publ_section_title
;
 Synthesis of Balsaminone A, a Naturally Occurring Pentacyclic
 Dinaphthofuran Quinone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8082
_journal_page_last               8087
_journal_paper_doi               10.1021/jo201395n
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C22 H12 O5'
_chemical_formula_sum            'C22 H12 O5'
_chemical_formula_weight         356.32
_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           'enCIFer editing of SHELXL-97 created file'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.5720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4920(2)
_cell_length_b                   24.5859(6)
_cell_length_c                   7.0468(2)
_cell_measurement_reflns_used    8001
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.39
_cell_volume                     1576.20(7)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    ' ? '
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Bruker SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w AND \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15367
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.8967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                3404
_reflns_number_total             3596
_reflns_threshold_expression     >2I\s(I)
_cod_data_source_file            jo201395n_si_002.cif
_cod_data_source_block           jpcjmb
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026625
_nottingham_internal_coll_name   JPCJMB
_nottingham_internal_coll_number 9134
_nottingham_internal_coll_client JP/CJM
_nottingham_internal_coll_type   CUSTOM
_nottingham_internal_coll_frame_time 30s
_nottingham_internal_coll_frame_width '0.36 and 0.5 DEGREE'
_nottingham_internal_coll_frame_method '\w AND \f SCANS'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   4/2/2010
_nottingham_internal_process_user WL
_nottingham_internal_process_date 8/2/2010
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 8/2/2010
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 8/2/2010
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 10/2/2010