Total Synthesis of (\±)-Communesin F via a Cycloaddition with Indol-2-one
Johannes Belmar; Raymond L. Funk; Journal of the American Chemical Society 134 (2012) 16941–16943; doi:10.1021/ja307277w

data_4118767
_publ_section_title
;
 Total Synthesis of (\+-)-Communesin F via a Cycloaddition with
 Indol-2-one
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16941
_journal_page_last               16943
_journal_paper_doi               10.1021/ja307277w
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C30 H37 N3 O4'
_chemical_formula_sum            'C30 H37 N3 O4'
_chemical_formula_weight         503.63
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.079(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.598(6)
_cell_length_b                   14.092(5)
_cell_length_c                   12.888(4)
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.143
_cell_measurement_theta_min      2.648
_cell_volume                     2797.4(17)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20706
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0651P)^2^+0.0397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                3606
_reflns_number_total             6875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307277w_si_003.cif
_cod_data_source_block           jub5m
_cod_original_cell_volume        2797.4(16)
_cod_database_code               4118767