Stereochemical Assignment of C-24 and C-25 of Amarasterone A, a Putative Biosynthetic Intermediate of Cyasterone.
Hirayama, Yui; Okuzumi, Keiko; Masubuti, Hironori; Uekusa, Hidehiro; Girault, Jean-Pierre; Fujimoto, Yoshinori; The Journal of organic chemistry 79 (2014) 5471–5477; doi:10.1021/jo5005108

data_4029591
_publ_section_title
;
 Stereochemical Assignment of C-24 and C-25 of Amarasterone A,
 a&#x00A0;Putative Biosynthetic Intermediate of Cyasterone.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5471
_journal_page_last               5477
_journal_paper_doi               10.1021/jo5005108
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H52 O4, C H4 O'
_chemical_formula_sum            'C31 H56 O5'
_chemical_formula_weight         508.75
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.3800(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7540(4)
_cell_length_b                   6.03911(17)
_cell_length_c                   19.9264(7)
_cell_measurement_reflns_used    8450
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.57
_cell_measurement_theta_min      3.48
_cell_volume                     1528.03(8)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17466
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.179
_diffrn_reflns_theta_min         3.481
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.11(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5124
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0973P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.835
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                3166
_reflns_number_total             5124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5005108_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4029591--4029592.cif.'
_cod_database_code               4029591
_shelx_estimated_absorpt_t_min   0.852
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-3
_shelx_res_checksum              35253
_shelx_hkl_checksum              47030