Fully Substituted Carbon Centers by Diastereoselective Spirocyclization: Stereoselective Synthesis of (+)-Lepadiformine C
Matthew A. Perry; Matthew D. Morin; Brian W. Slafer; Scott A. Wolckenhauer; Scott D. Rychnovsky; Journal of the American Chemical Society 132 (2010) 9591–9593; doi:10.1021/ja104250b

data_4102680
_publ_section_title
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 Fully Substituted Carbon Centers by Diastereoselective Spirocyclization:
 Stereoselective Synthesis of (+)-Lepadiformine C
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9591
_journal_page_last               9593
_journal_paper_doi               10.1021/ja104250b
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_sum            'C21 H39 N O3'
_chemical_formula_weight         353.53
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.397(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.177(2)
_cell_length_b                   9.864(2)
_cell_length_c                   12.207(3)
_cell_measurement_reflns_used    6855
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.29
_cell_volume                     1070.3(4)
_computing_cell_refinement       'Bruker SMART APEX2/SAINT'
_computing_data_collection       'Bruker SMART APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10734
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.014(6)
_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   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1071P)^2^+0.0668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                3613
_reflns_number_total             4058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104250b_si_002.cif
_cod_data_source_block           sdr22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4102680