Cobalt-catalyzed enantioselective directed C-h alkylation of indole with styrenes.
Lee, Pin-Sheng; Yoshikai, Naohiko; Organic letters 17 (2015) 22–25; doi:10.1021/ol503119z

data_1518455
_publ_section_title
;
 Cobalt-catalyzed enantioselective directed C-h alkylation of indole with
 styrenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              22
_journal_page_last               25
_journal_paper_doi               10.1021/ol503119z
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ref
_chemical_formula_sum            'C29 H37 N3 O4'
_chemical_formula_weight         491.61
_chemical_name_systematic
;
tert-butyl 3-((E)-(((S)-2-(methoxymethyl)pyrrolidin-1-yl)imino)methyl)
-2-((R)-1-phenylethyl)-1H-indole-1-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7880(4)
_cell_length_b                   16.0615(10)
_cell_length_c                   20.7023(12)
_cell_measurement_reflns_used    1348
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      20.1888
_cell_measurement_theta_min      3.0689
_cell_volume                     2589.6(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.1070
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11213
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                4159
_reflns_number_total             6157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503119z_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1518455.cif.'
_cod_database_code               1518455
_shelx_res_checksum              40429
_shelx_hkl_checksum              46513