Palladium and Copper Cocatalyzed Tandem N-H/C-H Bond Functionalization: Synthesis of CF3-Containing Indolo- and Pyrrolo[2,1-a]isoquinolines
Lei-Lei Sun; Zhi-Yong Liao; Ri-Yuan Tang; Chen-Liang Deng; Xing-Guo Zhang; Journal of Organic Chemistry 77 (2012) 2850–2856; doi:10.1021/jo3000404

data_4027080
_publ_section_title
;
 Palladium and Copper Cocatalyzed Tandem N-H/C-H Bond Functionalization:
 Synthesis of CF3-Containing Indolo- and Pyrrolo[2,1-a]isoquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2850
_journal_page_last               2856
_journal_paper_doi               10.1021/jo3000404
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C18 H12 F3 N O'
_chemical_formula_sum            'C18 H12 F3 N O'
_chemical_formula_weight         315.29
_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                 99.641(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2933(7)
_cell_length_b                   10.0821(9)
_cell_length_c                   17.0581(13)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      3.15
_cell_volume                     1406.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10500
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0825P)^2^+0.0148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1980
_reflns_number_total             2585
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3000404_si_002.cif
_cod_data_source_block           mo_20110826b_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027080