Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis
Narobe, Rok; Murugesan, Kathiravan; Schmid, Simon; König, Burkhard; ACS Catalysis  (2021) 809–817; doi:10.1021/acscatal.1c05077

data_4519224
_publ_section_title
;
 Decarboxylative Ritter-Type Amination by Cooperative Iodine
 (I/III)&#x2500;Boron Lewis Acid Catalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              809
_journal_page_last               817
_journal_paper_doi               10.1021/acscatal.1c05077
_journal_year                    2021
_chemical_formula_moiety         'C9 H10 N2 O3'
_chemical_formula_sum            'C9 H10 N2 O3'
_chemical_formula_weight         194.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.162(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6885(2)
_cell_length_b                   9.5916(2)
_cell_length_c                   8.4382(2)
_cell_measurement_reflns_used    6463
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.5440
_cell_measurement_theta_min      3.8110
_cell_volume                     931.18(3)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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     30.00  93.00   0.50    0.25    --   62.53   0.00 -90.00  126
  2  \w     52.00 111.00   0.50    0.80    --   75.27  15.00-180.00  118
  3  \w     59.00 103.00   0.50    0.25    --   62.53  15.00 -30.00   88
  4  \w     47.00 107.00   0.50    0.80    --   75.27   0.00 -60.00  120
  5  \w     68.00 107.00   0.50    0.80    --   75.27   0.00   0.00   78
  6  \w     55.00 105.00   0.50    0.80    --   75.27   0.00  60.00  100
  7  \w     50.00 112.00   0.50    0.80    --   75.27  15.00 120.00  124
  8  \w    -80.00 -36.00   0.50    0.25    --  -68.34   0.00 -30.00   88
  9  \w    -92.00 -37.00   0.50    0.25    --  -68.34   0.00-120.00  110
 10  \w    -70.00 -30.00   0.50    0.25    --  -68.34 113.00-166.00   80
 11  \w    -77.00 -52.00   0.50    0.25    --  -64.16 113.00-166.00   50
 12  \w    -91.00 -41.00   0.50    0.25    --  -68.34 125.00 -90.00  100
 13  \w    -91.00 -34.00   0.50    0.25    --  -68.34 125.00 -30.00  114
 14  \w    -71.00 -45.00   0.50    0.25    --  -64.16 -15.00 120.00   52
 15  \w   -101.00 -76.00   0.50    0.25    --  -64.16 -15.00 120.00   50
 16  \w     58.00  90.00   0.50    0.80    --   75.27-113.00 102.00   64
 17  \w     32.00  58.00   0.50    0.25    --   62.53-125.00 120.00   52
 18  \w     73.00  99.00   0.50    0.80    --   75.27-125.00 -60.00   52
 19  \w     37.00  96.00   0.50    0.25    --   72.38-125.00 -90.00  118
 20  \w     39.00  68.00   0.50    0.80    --   75.27-125.00 -60.00   58
 21  \w     26.00  84.00   0.50    0.25    --   62.53-125.00-120.00  116
 22  \w     24.00  84.00   0.50    0.25    --   62.53-125.00-180.00  120
 23  \w     73.00  99.00   0.50    0.80    --   75.27-125.00-180.00   52
 24  \w     39.00  99.00   0.50    0.80    --   75.27-125.00-150.00  120
 25  \w     43.00  69.00   0.50    0.80    --   75.27-125.00-180.00   52
 26  \w     36.00  98.00   0.50    0.80    --   75.27-125.00 -30.00  124
 27  \w     59.00  99.00   0.50    0.80    --   75.27-125.00  60.00   80
 28  \w     37.00  62.00   0.50    0.25    --   72.38-113.00 102.00   50
 29  \w     24.00  71.00   0.50    0.25    --   62.53-113.00 102.00   94
 30  \w     37.00  97.00   0.50    0.80    --   75.27-125.00 150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054968000
_diffrn_orient_matrix_UB_12      -0.1335604000
_diffrn_orient_matrix_UB_13      -0.1024069000
_diffrn_orient_matrix_UB_21      0.0366695000
_diffrn_orient_matrix_UB_22      0.0842149000
_diffrn_orient_matrix_UB_23      -0.1383073000
_diffrn_orient_matrix_UB_31      0.1286614000
_diffrn_orient_matrix_UB_32      -0.0294939000
_diffrn_orient_matrix_UB_33      0.0692348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10243
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.793
_diffrn_reflns_theta_min         3.842
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0457P)^2^+0.2681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1685
_reflns_number_total             1822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05077_si_002.cif
_cod_data_source_block           u022
_cod_database_code               4519224
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H10 N2 O3'
_chemical_oxdiff_usercomment     Narobe_Koenig_RN-595
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C9(H9), C8(H8), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              94756
_shelx_hkl_checksum              67699
_olex2_date_sample_data_collection 2021-04-01
_olex2_date_sample_submission    2021-02-23
_olex2_submission_original_sample_id RN-595
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.825