Enantioselective α-Aminophosphonate Functionalization of Indole Ring through an Organocatalyzed Friedel-Crafts Reaction.
Maestro, Aitor; Martinez de Marigorta, Edorta; Palacios, Francisco; Vicario, Javier; The Journal of organic chemistry 84 (2019) 1094–1102; doi:10.1021/acs.joc.8b02843

data_4035963
_publ_section_title
;
 Enantioselective \a-Aminophosphonate Functionalization of Indole Ring
 through an Organocatalyzed Friedel-Crafts Reaction.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1094
_journal_page_last               1102
_journal_paper_doi               10.1021/acs.joc.8b02843
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H26 F1 N2 O4 P1'
_chemical_formula_sum            'C22 H26 F N2 O4 P'
_chemical_formula_weight         432.42
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-21T12:21:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.2663(2)
_cell_length_b                   27.2663(2)
_cell_length_c                   12.3982(2)
_cell_measurement_reflns_used    33123
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.695
_cell_measurement_theta_min      3.879
_cell_measurement_wavelength     1.54184
_cell_volume                     9217.46(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -112.00 -84.00   1.00    1.00    --  -41.33 -99.00  90.00   28
  2  \w   -112.00 -85.00   1.00    1.00    --  -41.33 -99.00 120.00   27
  3  \w     26.00 109.00   1.00    1.00    --   41.33  45.00-161.00   83
  4  \w     20.00 113.00   1.00    1.00    --   41.33  57.00 120.00   93
  5  \w     34.00  59.00   1.00    4.00    --  108.36 -45.00 150.00   25
  6  \w     38.00  64.00   1.00    4.00    --  108.36 -45.00 120.00   26
  7  \w     41.00  76.00   1.00    4.00    --  108.36 -45.00 -60.00   35
  8  \w     34.00  63.00   1.00    4.00    --  108.36 -30.00 150.00   29
  9  \w     73.00 157.00   1.00    4.00    --  108.36 125.00  30.00   84
 10  \w     75.00 158.00   1.00    4.00    --  108.36  77.00 120.00   83
 11  \w    104.00 130.00   1.00    4.00    --  108.36  45.00-161.00   26
 12  \w     31.00  57.00   1.00    4.00    --  108.36 -30.00 -90.00   26
 13  \w     76.00 158.00   1.00    4.00    --  108.36 128.00  66.00   82
 14  \w     41.00  77.00   1.00    4.00    --  108.36 -45.00 -30.00   36
 15  \w   -107.00 -81.00   1.00    1.00    --  -41.33 -99.00-180.00   26
 16  \w     15.00  91.00   1.00    1.00    --   41.33  38.00 -60.00   76
 17  \w     14.00  92.00   1.00    1.00    --   41.33-125.00  30.00   78
 18  \w   -157.00-128.00   1.00    4.00    --  -83.00-125.00  30.00   29
 19  \w   -121.00 -81.00   1.00    4.00    --  -83.00-125.00 -90.00   40
 20  \w     60.00 142.00   1.00    4.00    --  108.36 -77.00 -30.00   82
 21  \w    103.00 129.00   1.00    4.00    --  108.36 -77.00  90.00   26
 22  \w     39.00  75.00   1.00    4.00    --  108.36 -77.00  90.00   36
 23  \w     32.00  64.00   1.00    4.00    --  108.36 -30.00-180.00   32
 24  \w     43.00 100.00   1.00    4.00    --  108.36 -94.00-120.00   57
 25  \w     78.00 130.00   1.00    4.00    --  108.36 125.00 -60.00   52
 26  \w    110.00 157.00   1.00    4.00    --  108.36  45.00  30.00   47
 27  \w     74.00 117.00   1.00    4.00    --  108.36-125.00   0.00   43
 28  \w     47.00  74.00   1.00    4.00    --  108.36 -45.00   0.00   27
 29  \w     58.00 109.00   1.00    4.00    --  108.36 -94.00 150.00   51
 30  \w     90.00 117.00   1.00    4.00    --  108.36-125.00 120.00   27
 31  \w   -124.00 -79.00   1.00    1.00    --  -41.33 -99.00   0.00   45
 32  \w   -119.00  -8.00   1.00    1.00    --  -41.33 -76.00-126.00  111
 33  \w   -120.00  -8.00   1.00    1.00    --  -41.33 -77.00 -60.00  112
 34  \w   -120.00  -8.00   1.00    1.00    --  -41.33 -77.00 150.00  112
 35  \w      2.00  99.00   1.00    1.00    --   41.33-125.00 -60.00   97
 36  \w     15.00 117.00   1.00    1.00    --   41.33  38.00  30.00  102
 37  \w    -33.00  71.00   1.00    1.00    --   41.33 -57.00 120.00  104
 38  \w      8.00 120.00   1.00    1.00    --   41.33  77.00  30.00  112
 39  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00 -30.00  113
 40  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00  90.00  113
 41  \w   -157.00 -53.00   1.00    4.00    --  -83.00 -61.00   0.00  104
 42  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00-150.00  113
 43  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00 150.00  113
 44  \w   -162.00 -49.00   1.00    4.00    --  -83.00 -77.00 -90.00  113
 45  \w     78.00 158.00   1.00    4.00    --  108.36  61.00-180.00   80
 46  \w     81.00 158.00   1.00    4.00    --  108.36  45.00-120.00   77
 47  \w     78.00 158.00   1.00    4.00    --  108.36  30.00 -60.00   80
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0175513
_diffrn_orient_matrix_UB_12      0.021364
_diffrn_orient_matrix_UB_13      -0.1084395
_diffrn_orient_matrix_UB_21      0.0263628
_diffrn_orient_matrix_UB_22      -0.0417499
_diffrn_orient_matrix_UB_23      -0.0603194
_diffrn_orient_matrix_UB_31      -0.0467816
_diffrn_orient_matrix_UB_32      -0.031523
_diffrn_orient_matrix_UB_33      0.0067145
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            81960
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         3.917
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+10.4793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                3972
_reflns_number_total             4361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02843_si_002.cif
_cod_data_source_block           a20170100_am1651
_cod_original_cell_volume        9217.42(17)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4035963