Efficient iron-catalyzed direct acylation of amines with carboxylic acids and esters under oxygenated conditions
Obieta, Maria; Urgoitia, Garazi; Herrero, María Teresa; SanMartin, Raul; Catalysis Science & Technology 14 (2024) 478–488; doi:10.1039/D3CY01429K

data_1570631
_publ_section_title
;
 Efficient iron-catalyzed direct acylation of amines with carboxylic acids
 and esters under oxygenated conditions
;
_journal_issue                   2
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              478
_journal_page_last               488
_journal_paper_doi               10.1039/D3CY01429K
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O2'
_chemical_formula_sum            'C17 H19 N O2'
_chemical_formula_weight         269.33
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-07-13T13:43:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.40420(10)
_cell_length_b                   22.6075(4)
_cell_length_c                   23.7568(4)
_cell_measurement_reflns_used    26127
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.278
_cell_measurement_theta_min      2.639
_cell_volume                     2890.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_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   -109.00 -84.00   0.50    3.00    --  -36.99-148.00 139.00   50
  2  \w    -85.00 -27.00   0.50    3.00    --  -36.99 125.00  22.00  116
  3  \w    -64.00 -39.00   0.50    3.00    --  -36.99 148.00-172.00   50
  4  \w     56.00  81.00   0.50    3.00    --   36.99-148.00 139.00   50
  5  \w     41.00  94.00   0.50    3.00    --   36.99-125.00 -55.00  106
  6  \w    102.00 129.00   0.50   12.00    --  111.20 125.00  22.00   54
  7  \w     99.00 124.00   0.50   12.00    --  111.20 148.00-172.00   50
  8  \w     66.00 129.00   0.50   12.00    --  111.20-148.00 139.00  126
  9  \w     72.00 108.00   0.50   12.00    --  111.20-125.00 -55.00   72
 10  \w    -63.00   0.00   0.50    3.00    --  -36.99 -77.00-150.00  126
 11  \w   -114.00 -60.00   0.50    3.00    --  -36.99 -57.00  30.00  108
 12  \w   -111.00  52.00   0.50    3.00    --  -36.99  19.00 -30.00  326
 13  \w   -113.00 -11.00   0.50    3.00    --  -36.99 -57.00 120.00  204
 14  \w    -78.00 -42.00   0.50    3.00    --  -36.99-178.00  60.00   72
 15  \w   -124.00 -93.00   0.50    3.00    --  -36.99-178.00  60.00   62
 16  \w   -110.00 -74.00   0.50    3.00    --  -36.99 -77.00-150.00   72
 17  \w    -46.00 -12.00   0.50    3.00    --   36.99 -38.00  90.00   68
 18  \w     22.00  51.00   0.50    3.00    --   36.99 -38.00  90.00   58
 19  \w    100.00 125.00   0.50    3.00    --   36.99-178.00 -90.00   50
 20  \w     75.00 123.00   0.50    3.00    --   36.99 178.00 150.00   96
 21  \w     63.00  89.00   0.50    3.00    --   36.99-178.00 -90.00   52
 22  \w     53.00  79.00   0.50   12.00    --  111.20-112.00  30.00   52
 23  \w     66.00  92.00   0.50   12.00    --  111.20 178.00 -60.00   52
 24  \w     43.00  70.00   0.50   12.00    --  111.20 -61.00  90.00   54
 25  \w     64.00 146.00   0.50   12.00    --  111.20 178.00 150.00  164
 26  \w     67.00 112.00   0.50   12.00    --  111.20 178.00-120.00   90
 27  \w     30.00  55.00   0.50   12.00    --  111.20 -45.00  60.00   50
 28  \w     43.00  69.00   0.50   12.00    --  111.20-112.00 -60.00   52
 29  \w     27.00 176.00   0.50   12.00    --  111.20  15.00 -60.00  298
 30  \w     84.00 137.00   0.50   12.00    --  111.20  45.00-180.00  106
 31  \w     79.00 106.00   0.50   12.00    --  111.20-112.00 -60.00   54
 32  \w     75.00 103.00   0.50   12.00    --  111.20 -45.00 -60.00   56
 33  \w    112.00 153.00   0.50   12.00    --  111.20 112.00  60.00   82
 34  \w     38.00 102.00   0.50   12.00    --  111.20 -95.00 120.00  128
 35  \w     34.00  71.00   0.50   12.00    --  111.20 -45.00 -60.00   74
 36  \w     85.00 142.00   0.50   12.00    --  111.20 -61.00-180.00  114
 37  \w    105.00 172.00   0.50   12.00    --  111.20  61.00-120.00  134
 38  \w    104.00 144.00   0.50   12.00    --  111.20 178.00 -60.00   80
 39  \w     35.00 149.00   0.50   12.00    --  111.20 -77.00-120.00  228
 40  \w     42.00  75.00   0.50   12.00    --  111.20 -61.00-180.00   66
 41  \w     81.00 107.00   0.50   12.00    --  111.20 -61.00  90.00   52
 42  \w     82.00 137.00   0.50   12.00    --  111.20 -45.00  60.00  110
 43  \w    137.00 176.00   0.50   12.00    --  111.20  61.00 120.00   78
 44  \w    103.00 129.00   0.50   12.00    --  111.20 112.00 -60.00   52
 45  \w     82.00 134.00   0.50   12.00    --  111.20  61.00 120.00  104
 46  \w    -84.00 -43.00   0.50    3.00    --  -36.99 178.00-120.00   82
 47  \w     89.00 114.00   0.50    3.00    --   36.99  57.00  30.00   50
 48  \w     65.00  90.00   0.50    3.00    --   36.99 178.00  30.00   50
 49  \w     29.00  55.00   0.50    3.00    --   36.99  57.00  30.00   52
 50  \w    105.00 131.00   0.50   12.00    --  111.20  61.00   0.00   52
 51  \w    112.00 138.00   0.50   12.00    --  111.20 112.00  30.00   52
 52  \w    131.00 161.00   0.50   12.00    --  111.20 112.00 120.00   60
 53  \w    153.00 178.00   0.50   12.00    --  111.20  61.00   0.00   50
 54  \w     93.00 119.00   0.50   12.00    --  111.20  77.00 -60.00   52
 55  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00-120.00  234
 56  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  90.00  234
 57  \w   -126.00 -41.00   0.50    3.00    --  -36.99-178.00 -90.00  170
 58  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00   0.00  234
 59  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 120.00  234
 60  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  60.00  234
 61  \w   -114.00  -7.00   0.50    3.00    --  -36.99 -57.00-120.00  214
 62  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 -60.00  234
 63  \w   -120.00   1.00   0.50    3.00    --  -36.99 -38.00   0.00  242
 64  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 -30.00  234
 65  \w   -120.00   1.00   0.50    3.00    --  -36.99 -38.00  60.00  242
 66  \w   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  30.00  234
 67  \w     63.00 125.00   0.50    3.00    --   36.99 178.00  60.00  124
 68  \w     63.00 125.00   0.50    3.00    --   36.99 178.00-120.00  124
 69  \w     59.00 178.00   0.50   12.00    --  111.20  30.00  60.00  238
 70  \w     59.00 115.00   0.50   12.00    --  111.20  30.00 -60.00  112
 71  \w     79.00 178.00   0.50   12.00    --  111.20  61.00 150.00  198
 72  \w     59.00 178.00   0.50   12.00    --  111.20  30.00   0.00  238
 73  \w     59.00 178.00   0.50   12.00    --  111.20  30.00 120.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0088143
_diffrn_orient_matrix_UB_12      -0.0650537
_diffrn_orient_matrix_UB_13      0.0190709
_diffrn_orient_matrix_UB_21      0.0346755
_diffrn_orient_matrix_UB_22      0.019849
_diffrn_orient_matrix_UB_23      0.0622701
_diffrn_orient_matrix_UB_31      -0.2838119
_diffrn_orient_matrix_UB_32      0.0044287
_diffrn_orient_matrix_UB_33      0.0011155
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51265
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.994
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (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            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (99%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.02(10)
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     807
_refine_ls_number_reflns         10736
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0996P)^2^+0.2720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                9216
_reflns_number_total             10736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy01429k2.cif
_cod_data_source_block           b20230143_o342m2remducu
_cod_depositor_comments
'Adding full bibliography for 1570630--1570631.cif.'
_cod_database_code               1570631