Pd-Catalyzed Intramolecular Heck Reaction, C(sp(2))-H Activation, 1,4-Pd Migration, and Aminopalladation: Chemoselective Synthesis of Dihydroindeno[1,2,3-kl]acridines and 3-Arylindoles.
Gu, Zheng-Yang; Liu, Cheng-Guo; Wang, Shun-Yi; Ji, Shun-Jun; Organic letters 18 (2016) 2379–2382; doi:10.1021/acs.orglett.6b00843

data_1543235
_publ_section_title
;
 Pd-Catalyzed Intramolecular Heck Reaction, C(sp(2))-H Activation, 1,4-Pd
 Migration, and Aminopalladation: Chemoselective Synthesis of
 Dihydroindeno[1,2,3-kl]acridines and 3-Arylindoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2379
_journal_page_last               2382
_journal_paper_doi               10.1021/acs.orglett.6b00843
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-31
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.2222(6)
_cell_length_b                   12.0292(4)
_cell_length_c                   19.1416(8)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3130
_cell_measurement_theta_min      3.3630
_cell_volume                     3274.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -13.00   27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000   30.0000 40

  2 omega -102.00  -57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889 -178.0000 -180.0000 45

  3 omega   -2.00   31.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   77.0000 -150.0000 33

  4 omega  -51.00   13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -77.0000  120.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0009162000
_diffrn_orient_matrix_UB_12      -0.0560904000
_diffrn_orient_matrix_UB_13      0.0114723000
_diffrn_orient_matrix_UB_21      0.0333605000
_diffrn_orient_matrix_UB_22      0.0128695000
_diffrn_orient_matrix_UB_23      0.0263117000
_diffrn_orient_matrix_UB_31      -0.0370545000
_diffrn_orient_matrix_UB_32      0.0129523000
_diffrn_orient_matrix_UB_33      0.0234178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12732
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0558P)^2^+0.1993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2320
_reflns_number_total             3340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00843_si_003.cif
_cod_data_source_block           g150804a
_cod_depositor_comments
'Adding full bibliography for 1543235--1543236.cif.'
_cod_database_code               1543235
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_date_sample_data_collection 2015-08-04
_olex2_submission_special_instructions 'No special instructions were received'