SmI~2~-Promoted Radical Addition Reactions with N-(2-Indolylacyl)oxazolidinones: Synthesis of Bisindole Compounds
Karl B. Lindsay; Francesc Ferrando; Kasper L. Christensen; Jacob Overgaard; Tomàs Roca; M.-Lluïsa Bennasar; Troels Skrydstrup; Journal of Organic Chemistry 72 (2007) 4181–4188; doi:10.1021/jo070273d

data_4022928
_publ_contact_author             'Farrugia, Louis J.'
_publ_contact_author_email       louis@chem.gla.ac.uk
_publ_section_title
;
 SmI~2~-Promoted Radical Addition Reactions with
 N-(2-Indolylacyl)oxazolidinones: Synthesis of Bisindole Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4181
_journal_page_last               4188
_journal_paper_doi               10.1021/jo070273d
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H24 N2 O6'
_chemical_formula_sum            'C34 H24 N2 O6'
_chemical_formula_weight         556.55
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      13
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-11T12:35:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.187(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.717(2)
_cell_length_b                   5.1567(9)
_cell_length_c                   18.788(3)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_measurement_wavelength     0.71073
_cell_volume                     1288.4(4)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.716
_diffrn_measured_fraction_theta_max 0.716
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1500
_diffrn_reflns_theta_full        21.8
_diffrn_reflns_theta_max         21.8
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                686
_reflns_number_total             1110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070273dsi20070208_060036.cif
_cod_data_source_block           06jo0034_01
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4022928