Rhodium(II)-Catalyzed Regioselective Remote C–H Alkylation of Protic Indoles
Kong, Lingheng; Han, Xi; Chen, Haohua; Sun, Huaming; Lan, Yu; Li, Xingwei; ACS Catalysis  (2021) 4929–4935; doi:10.1021/acscatal.1c01052

data_4518667
_publ_section_title
;
 Rhodium(II)-Catalyzed Regioselective Remote C--H Alkylation of Protic
 Indoles
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4929
_journal_page_last               4935
_journal_paper_doi               10.1021/acscatal.1c01052
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 Br N O'
_chemical_formula_sum            'C22 H18 Br N O'
_chemical_formula_weight         392.28
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.456(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0333(3)
_cell_length_b                   29.8691(15)
_cell_length_c                   9.4917(5)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      68.270
_cell_measurement_theta_min      2.959
_cell_volume                     1676.41(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20171
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         2.959
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.404
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0823 after correction.
The Ratio of minimum to maximum transmission is 0.6583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.283
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0731
_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^)+12.1442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2961
_reflns_number_total             2977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01052_si_002.cif
_cod_data_source_block           s_pl
_cod_database_code               4518667
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.428
_shelx_estimated_absorpt_t_min   0.281
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C3(H3), C6(H6), C10(H10), C14(H14), C15(H15), C17(H17),
 C21(H21)
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_shelx_res_checksum              91136
_shelx_hkl_checksum              51506
_olex2_submission_special_instructions 'No special instructions were received'