Rhodium-Catalyzed Annulation of Tertiary AnilineN-Oxides toN-Alkylindoles: Regioselective C–H Activation, Oxygen-Atom Transfer, andN-Dealkylative Cyclization
Li, Bin; Xu, Hong; Wang, Huanan; Wang, Baiquan; ACS Catalysis 6 (2016) 3856–; doi:10.1021/acscatal.6b00311

data_4513884
_publ_section_title
;
 Rhodium-Catalyzed Annulation of Tertiary AnilineN-Oxides
 toN-Alkylindoles: Regioselective C--H Activation, Oxygen-Atom Transfer,
 andN-Dealkylative Cyclization
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3856
_journal_paper_doi               10.1021/acscatal.6b00311
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.445(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.787(2)
_cell_length_b                   12.7131(18)
_cell_length_c                   12.427(2)
_cell_measurement_reflns_used    5683
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1839.1(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       16
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18357
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.4158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3787
_reflns_number_total             4215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b00311_si_002.cif
_cod_data_source_block           m20151017c1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4513884--4513885.cif.
;
_cod_original_cell_volume        1839.2(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4513884