Palladium-Catalyzed Oxidative Arylacetoxylation of Alkenes: Synthesis of Indole and Indoline Derivatives
Karnakanti, Shuklachary; Zang, Zhong-Lin; Zhao, Sheng; Shao, Pan-Lin; Hu, Ping; He, Yun; Chem. Commun.  (2017) –; doi:10.1039/C7CC06448A

data_7120693
_publ_section_title
;
 Palladium-Catalyzed Oxidative Arylacetoxylation of Alkenes: Synthesis of
 Indole and Indoline Derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06448A
_journal_year                    2017
_chemical_formula_moiety         'C23 H17 Cl N2 O3'
_chemical_formula_sum            'C23 H17 Cl N2 O3'
_chemical_formula_weight         404.83
_chemical_name_systematic
'(5-chloro-1-picolinoyl-1H-indol-3-yl)(phenyl)methyl acetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.018(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6917(10)
_cell_length_b                   7.5033(7)
_cell_length_c                   27.151(2)
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7700
_cell_measurement_theta_min      3.4260
_cell_volume                     1971.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -77.00   49.00   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000    0.0000 180

  2 omega  -21.00   24.50   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -30.0000 65

  3 omega   35.00   84.70   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5294  178.0000  120.0000 71

  4 omega   23.00   57.30   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5294 -104.0000  131.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0018451000
_diffrn_orient_matrix_UB_12      -0.0262993000
_diffrn_orient_matrix_UB_13      0.0250992000
_diffrn_orient_matrix_UB_21      0.0732109000
_diffrn_orient_matrix_UB_22      -0.0038048000
_diffrn_orient_matrix_UB_23      0.0003572000
_diffrn_orient_matrix_UB_31      0.0035612000
_diffrn_orient_matrix_UB_32      0.0907461000
_diffrn_orient_matrix_UB_33      0.0072944000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10239
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       solid
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.2740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             4036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06448a2.cif
_cod_data_source_block           170713_s1_wz
_cod_database_code               7120693
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'