Caeruleanone A, a Rotenoid with a New Arrangement of the D-Ring from the Fruits of Millettia caerulea.
Bueno Pérez, Lynette; Pan, Li; Muñoz Acuña, Ulyana; Li, Jie; Chai, Hee-Byung; Gallucci, Judith C.; Ninh, Tran Ngoc; Carcache de Blanco, Esperanza J.; Soejarto, Djaja D.; Kinghorn, A. Douglas; Organic letters 16 (2014) 1462–1465; doi:10.1021/ol500266z

data_1513828
_publ_section_title
;
 Caeruleanone A, a Rotenoid with a New Arrangement of the D-Ring from the
 Fruits of Millettia caerulea.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1462
_journal_page_last               1465
_journal_paper_doi               10.1021/ol500266z
_journal_volume                  16
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H30 O7'
_chemical_formula_sum            'C28 H30 O7'
_chemical_formula_weight         478.52
_chemical_name_common            'Kinghorn 1937'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-03-20T16:36:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.1420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6740(2)
_cell_length_b                   18.0944(3)
_cell_length_c                   21.0316(3)
_cell_measurement_reflns_used    8813
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      1.018
_cell_measurement_wavelength     0.71073
_cell_volume                     4819.77(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.276265E-1
_diffrn_orient_matrix_UB_12      0.512766E-1
_diffrn_orient_matrix_UB_13      0.67712E-2
_diffrn_orient_matrix_UB_21      -0.51775E-1
_diffrn_orient_matrix_UB_22      0.79575E-2
_diffrn_orient_matrix_UB_23      0.340728E-1
_diffrn_orient_matrix_UB_31      0.528234E-1
_diffrn_orient_matrix_UB_32      -0.19018E-1
_diffrn_orient_matrix_UB_33      0.325134E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            81260
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.49
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.8600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.114
_reflns_number_gt                6013
_reflns_number_total             8509
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol500266z_si_001.cif
_cod_data_source_block           Kinghorn1937
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1513828