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_1570630
_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         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.3
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-28T12:24:41-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.23281(4)
_cell_length_b                   11.33461(9)
_cell_length_c                   22.6110(2)
_cell_measurement_reflns_used    11719
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.391
_cell_measurement_theta_min      3.877
_cell_volume                     1341.100(19)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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   -116.00 -18.00   1.00    1.00    --  -42.13 -38.00   0.00   98
  2  \w   -116.00 -18.00   1.00    1.00    --  -42.13 -38.00 -60.00   98
  3  \w    -30.00  70.00   1.00    1.00    --   42.13 -57.00-120.00  100
  4  \w    -20.00  83.00   1.00    1.00    --   42.13 -99.00 150.00  103
  5  \w      2.00  98.00   1.00    1.00    --   42.13-125.00-150.00   96
  6  \w     35.00 118.00   1.00    1.00    --  107.93-125.00  60.00   83
  7  \w     80.00 158.00   1.00    1.00    --  107.93  30.00 -90.00   78
  8  \w     25.00 110.00   1.00    1.00    --  107.93 -94.00  90.00   85
  9  \w     35.00 118.00   1.00    1.00    --  107.93-125.00 -90.00   83
 10  \w     36.00 137.00   1.00    1.00    --  107.93 -61.00   0.00  101
 11  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00  90.00   37
 12  \w     82.00 158.00   1.00    1.00    --  107.93  45.00 -30.00   76
 13  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00 -30.00   37
 14  \w     32.00 141.00   1.00    1.00    --  107.93 -77.00  90.00  109
 15  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00 -60.00   37
 16  \w     35.00 118.00   1.00    1.00    --  107.93-125.00 -30.00   83
 17  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00 120.00   37
 18  \w     55.00 158.00   1.00    1.00    --  107.93  15.00 120.00  103
 19  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00 150.00   37
 20  \w     36.00 137.00   1.00    1.00    --  107.93 -61.00-120.00  101
 21  \w   -118.00 -10.00   1.00    1.00    --  -42.13 -77.00 120.00  108
 22  \w   -118.00 -46.00   1.00    1.00    --  -42.13 -77.00 -90.00   72
 23  \w   -115.00 -14.00   1.00    1.00    --  -42.13 -57.00-180.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2924024
_diffrn_orient_matrix_UB_12      0.015658
_diffrn_orient_matrix_UB_13      -0.0016663
_diffrn_orient_matrix_UB_21      -0.0004995
_diffrn_orient_matrix_UB_22      -0.0298542
_diffrn_orient_matrix_UB_23      -0.066485
_diffrn_orient_matrix_UB_31      -0.0347125
_diffrn_orient_matrix_UB_32      -0.1316018
_diffrn_orient_matrix_UB_33      0.0148982
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14622
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.997
_diffrn_reflns_theta_min         4.363
_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    0.664
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.76
_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    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.745
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_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 
 (100%). 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(6).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0427P)^2^+0.1690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2433
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy01429k2.cif
_cod_data_source_block           a20190015_ia32ca2t150k
_cod_depositor_comments
'Adding full bibliography for 1570630--1570631.cif.'
_cod_original_cell_volume        1341.10(2)
_cod_database_code               1570630