Revised Stereochemistry of Ficifolidione and Its Biological Activities against Insects and Cells
Nishiwaki, Hisashi; Fujiwara, Satomi; Wukirsari, Tuti; Iwamoto, Hiroyuki; Mori, Shigeki; Nishi, Kosuke; Sugahara, Takuya; Yamauchi, Satoshi; Shuto, Yoshihiro; Journal of Natural Products  (2014) 141212125500007–; doi:10.1021/np5006746

data_1518414
_publ_section_title
;
 Revised Stereochemistry of Ficifolidione and Its Biological Activities
 against Insects and Cells
;
_journal_name_full               'Journal of Natural Products'
_journal_page_first              141212125500007
_journal_paper_doi               10.1021/np5006746
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H38 O3'
_chemical_formula_sum            'C25 H38 O3'
_chemical_formula_weight         386.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.273(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4672(15)
_cell_length_b                   6.4647(9)
_cell_length_c                   17.515(2)
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      4.42
_cell_volume                     1131.7(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20967
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.155
_diffrn_reflns_theta_min         4.424
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                3052
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           20120528
_cod_original_cell_volume        1131.8(3)
_cod_database_code               1518414
_shelx_estimated_absorpt_t_min   0.849
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014-3
_shelx_res_checksum              84794
_shelx_hkl_checksum              4060