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_4102240
_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         'C44 H56 N2 O12'
_chemical_formula_sum            'C44 H56 N2 O12'
_chemical_formula_weight         804.91
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.926(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.924(14)
_cell_length_b                   7.236(6)
_cell_length_c                   39.64(3)
_cell_measurement_reflns_used    141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.43
_cell_measurement_theta_min      8.29
_cell_volume                     4796(7)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.836
_diffrn_measured_fraction_theta_max 0.836
_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  0.1748
_diffrn_reflns_av_sigmaI/netI    0.2372
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            27071
_diffrn_reflns_theta_full        66.42
_diffrn_reflns_theta_max         66.42
_diffrn_reflns_theta_min         8.29
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.8895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_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         0.287
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_coef       0.00022(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1047
_refine_ls_number_reflns         11876
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.0905
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                3968
_reflns_number_total             11876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1006806_si_004.cif
_cod_data_source_block           B103_7_189
_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_database_code               4102240