Palladium-Catalyzed C-H Arylation of Indoles at the C7 Position.
Yang, Youqing; Qiu, Xiaodong; Zhao, Yue; Mu, Yucheng; Shi, Zhuangzhi; Journal of the American Chemical Society 138 (2016) 495–498; doi:10.1021/jacs.5b11569

data_4124885
_publ_section_title
;
 Palladium-Catalyzed C-H Arylation of Indoles at the C7 Position.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              495
_journal_page_last               498
_journal_paper_doi               10.1021/jacs.5b11569
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C12 H16 N O P'
_chemical_formula_weight         221.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.787(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9522(13)
_cell_length_b                   7.8417(7)
_cell_length_c                   11.3721(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1163.22(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7387
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.123
_exptl_absorpt_coefficient_mu    0.210
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0601
_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^)+(0.1284P)^2^+3.5761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1864
_reflns_number_total             2016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b11569_si_002.cif
_cod_data_source_block           1_a
_cod_database_code               4124885
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              80614
_shelx_hkl_checksum              6053