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_4118766
_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         'C26 H24 Br N5 O4 S'
_chemical_formula_sum            'C26 H24 Br N5 O4 S'
_chemical_formula_weight         582.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.154(2)
_cell_angle_beta                 96.555(2)
_cell_angle_gamma                108.720(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8826(10)
_cell_length_b                   10.1582(12)
_cell_length_c                   15.4847(18)
_cell_measurement_reflns_used    4655
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.067
_cell_measurement_theta_min      2.673
_cell_volume                     1280.5(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      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12267
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    1.730
_exptl_absorpt_correction_T_max  0.8740
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+0.4005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                4840
_reflns_number_total             6187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307277w_si_002.cif
_cod_data_source_block           jub4s
_cod_database_code               4118766