Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles.
Ramella, Vincenzo; He, Zhiheng; Daniliuc, Constantin G.; Studer, Armido; Organic letters 17 (2015) 664–667; doi:10.1021/ol503689r

data_1518650
_publ_section_title
;
 Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              664
_journal_page_last               667
_journal_paper_doi               10.1021/ol503689r
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C25 H22 Cl N O4'
_chemical_formula_weight         435.89
_space_group_IT_number           2
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_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                73.585(1)
_cell_angle_beta                 78.745(1)
_cell_angle_gamma                86.593(1)
_cell_formula_units_Z            2
_cell_length_a                   8.5929(2)
_cell_length_b                   9.9207(3)
_cell_length_c                   13.6227(6)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      4.08
_cell_volume                     1092.53(6)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0000P)^2^+1.5939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                2961
_reflns_number_total             3752
_reflns_threshold_expression     >2sigma(I)
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_cod_data_source_block           stu7851
_cod_depositor_comments
'Adding full bibliography for 1518649--1518650.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1518650