Chemoselective N-H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid.
Cai, Yue; Gu, Qing; You, Shu-Li; Organic & biomolecular chemistry 16 (2018) 6146–6154; doi:10.1039/c8ob01863d

data_7156358
_publ_section_title
;
 Chemoselective N-H functionalization of indole derivatives via the
 Reissert-type reaction catalyzed by a chiral phosphoric acid.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6146
_journal_page_last               6154
_journal_paper_doi               10.1039/c8ob01863d
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H29 N3 O4'
_chemical_formula_weight         447.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-06-25 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.9210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9053(2)
_cell_length_b                   29.8896(7)
_cell_length_c                   10.0393(2)
_cell_measurement_reflns_used    8770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      131.856
_cell_measurement_theta_min      5.914
_cell_volume                     2442.69(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_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  0.1106
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34541
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.468
_diffrn_reflns_theta_min         2.957
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 2591 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0131(14)
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         8568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1123P)^2^+0.2302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1981
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6835
_reflns_number_total             8568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01863d2.cif
_cod_data_source_block           cu_d8v18305_0m
_cod_depositor_comments          'Adding full bibliography for 7156358.cif.'
_cod_database_code               7156358
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.924
_shelxl_version_number           2013-4
_shelx_res_checksum              85379