Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone
Matthew A. Boone; Rongbiao Tong; Frank E. McDonald; Sheri Lense; Rui Cao; Kenneth I. Hardcastle; Journal of the American Chemical Society 132 (2010) 5300–5308; doi:10.1021/ja1006806

data_4102238
_publ_section_title
;
 Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of
 ent-Abudinol B and Reassessment of the Structure of Muzitone
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5300
_journal_page_last               5308
_journal_paper_doi               10.1021/ja1006806
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C45.50 H59 Br2 O6'
_chemical_formula_sum            'C45.5 H59 Br2 O6'
_chemical_formula_weight         861.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8790(4)
_cell_length_b                   20.7162(7)
_cell_length_c                   24.1069(8)
_cell_measurement_reflns_used    7900
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      65.51
_cell_measurement_theta_min      8.34
_cell_volume                     4434.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17742
_diffrn_reflns_theta_full        66.70
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         8.34
_exptl_absorpt_coefficient_mu    2.666
_exptl_absorpt_correction_T_max  0.5916
_exptl_absorpt_correction_T_min  0.3610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_platon_squeeze_details
;

 A.L. Spek (1990) Acta Cryst. A46, C34 "PLATON-A Multipurpose 
 Crystallographic Tool," Utrecht University, Utrecht, The
 Netherlands, A.L. Spek (2006)

;
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+2.7756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1651
_reflns_number_gt                5333
_reflns_number_total             6314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1006806_si_002.cif
_cod_data_source_block           49
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C45.50 H59 Br2 O6'
_cod_database_code               4102238