Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.
Gutierrez, Elisa G.; Wong, Casey J.; Sahin, Aziza H.; Franz, Annaliese K.; Organic letters 13 (2011) 5754–5757; doi:10.1021/ol202329s

data_1502527
_publ_section_title
;
 Enantioselective and regioselective indium(III)-catalyzed addition of
 pyrroles to isatins.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5754
_journal_page_last               5757
_journal_paper_doi               10.1021/ol202329s
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H13 Cl N2 O2'
_chemical_formula_sum            'C14 H13 Cl N2 O2'
_chemical_formula_weight         276.71
_chemical_name_common
(S)-5-chloro-1-methyl-3-hydroxy-3-(1-methyl-1H-pyrrol-2-yl)-indolin-2-one
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.296(2)
_cell_length_b                   12.430(5)
_cell_length_c                   20.001(8)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      2.6
_cell_volume                     1316.7(9)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       \w
_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  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16828
_diffrn_reflns_theta_full        31.26
_diffrn_reflns_theta_max         31.26
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.126
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+1.4821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                3398
_reflns_number_total             4001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202329s_si_002.cif
_cod_data_source_block           NT93
_cod_original_cell_volume        1316.6(9)
_cod_database_code               1502527