C2/C4 Regioselective Heteroarylation of Indoles by Tuning C–H Metalation Modes
Chen, Shuyou; Zhang, Min; Su, Rongchuan; Chen, Xingyu; Feng, Boya; Yang, Yudong; You, Jingsong; ACS Catalysis 9 (2019) 6372–; doi:10.1021/acscatal.9b01273

data_4514796
_publ_section_title
;
 C2/C4 Regioselective Heteroarylation of Indoles by Tuning C--H Metalation
 Modes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6372
_journal_paper_doi               10.1021/acscatal.9b01273
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1896(2)
_cell_length_b                   13.9891(6)
_cell_length_c                   17.8940(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1799.71(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6058
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.606
_diffrn_reflns_theta_min         4.943
_exptl_absorpt_coefficient_mu    0.616
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             704
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0582
_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^)+(0.1080P)^2^+0.1330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.693
_reflns_number_gt                2886
_reflns_number_total             3076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01273_si_003.cif
_cod_data_source_block           ylp-xx
_cod_original_cell_volume        1799.70(12)
_cod_database_code               4514796
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              18196
_shelx_hkl_checksum              14531