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_4519222
_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         'C22 H17 I N2 O8'
_chemical_formula_sum            'C22 H17 I N2 O8'
_chemical_formula_weight         564.27
_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             2021-04-07
_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                 93.192(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3457(3)
_cell_length_b                   8.1316(3)
_cell_length_c                   21.5494(8)
_cell_measurement_reflns_used    14783
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      66.7480
_cell_measurement_theta_min      4.0740
_cell_volume                     2159.99(12)
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -69.00 -42.00   1.00    4.00    --  -43.66 102.00 166.00   27
  2  \w     -7.00  60.00   1.00    4.00    --   43.66-102.00  63.00   67
  3  \w     95.00 120.00   1.00   14.00    --   86.50 102.00 166.00   25
  4  \w     20.00  45.00   1.00   14.00    --   86.50-102.00  63.00   25
  5  \w   -105.00 -78.00   1.00   14.00    --  -90.00 102.00 166.00   27
  6  \w   -156.00-129.00   1.00   14.00    --  -90.00-102.00  63.00   27
  7  \w     13.00 121.00   1.00    4.00    --   43.66  19.00   0.00  108
  8  \w    -24.00  22.00   1.00    4.00    --   43.66 -37.00-180.00   46
  9  \w     43.00 113.00   1.00    4.00    --   43.66  37.00-180.00   70
 10  \w   -116.00 -89.00   1.00   14.00    --  -90.00  61.00-180.00   27
 11  \w    -55.00 -30.00   1.00   14.00    --  -90.00 125.00  60.00   25
 12  \w    -64.00 -23.00   1.00   14.00    --  -90.00  61.00-180.00   41
 13  \w    -61.00 -36.00   1.00   14.00    --  -90.00 125.00 -30.00   25
 14  \w   -173.00-128.00   1.00   14.00    --  -90.00 -94.00 -90.00   45
 15  \w   -104.00 -58.00   1.00   14.00    --  -90.00 125.00-180.00   46
 16  \w   -111.00 -71.00   1.00   14.00    --  -90.00 125.00  60.00   40
 17  \w   -110.00 -20.00   1.00   14.00    --  -90.00   0.00-120.00   90
 18  \w   -116.00 -21.00   1.00   14.00    --  -90.00  61.00   0.00   95
 19  \w   -162.00-114.00   1.00   14.00    --  -90.00-125.00 -60.00   48
 20  \w   -111.00 -46.00   1.00   14.00    --  -90.00  30.00 -60.00   65
 21  \w    -75.00 -50.00   1.00   14.00    --  -90.00 125.00-120.00   25
 22  \w   -112.00 -80.00   1.00   14.00    --  -90.00 125.00-120.00   32
 23  \w   -146.00-103.00   1.00   14.00    --  -90.00 -77.00-150.00   43
 24  \w   -108.00 -62.00   1.00   14.00    --  -90.00 125.00 -60.00   46
 25  \w   -100.00 -36.00   1.00   14.00    --  -90.00 125.00-150.00   64
 26  \w   -110.00 -61.00   1.00   14.00    --  -90.00 125.00 150.00   49
 27  \w    -93.00 -64.00   1.00   14.00    --  -90.00 125.00 -30.00   29
 28  \w   -170.00-131.00   1.00   14.00    --  -90.00   0.00-120.00   39
 29  \w   -163.00-108.00   1.00   14.00    --  -90.00 -77.00 -60.00   55
 30  \w   -146.00-111.00   1.00   14.00    --  -90.00-125.00-120.00   35
 31  \w    -91.00 -66.00   1.00   14.00    --  -90.00 125.00  90.00   25
 32  \w    -58.00 -31.00   1.00   14.00    --  -90.00 125.00  90.00   27
 33  \w   -113.00 -75.00   1.00   14.00    --  -90.00  61.00 -90.00   38
 34  \w    -60.00 -33.00   1.00   14.00    --  -90.00  61.00 -90.00   27
 35  \w   -111.00 -63.00   1.00   14.00    --  -90.00 125.00   0.00   48
 36  \w   -102.00 -30.00   1.00   14.00    --  -90.00  45.00-180.00   72
 37  \w   -116.00 -39.00   1.00   14.00    --  -90.00  30.00  30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0073607000
_diffrn_orient_matrix_UB_12      -0.1726500000
_diffrn_orient_matrix_UB_13      0.0289117000
_diffrn_orient_matrix_UB_21      0.0285338000
_diffrn_orient_matrix_UB_22      -0.0778213000
_diffrn_orient_matrix_UB_23      -0.0621890000
_diffrn_orient_matrix_UB_31      0.1214142000
_diffrn_orient_matrix_UB_32      0.0076360000
_diffrn_orient_matrix_UB_33      0.0205594000
_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  0.0852
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25044
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.118
_diffrn_reflns_theta_max         67.118
_diffrn_reflns_theta_min         4.109
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.124
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.650
_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_density_diffrn    1.735
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.933
_refine_diff_density_min         -1.947
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0965P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3499
_reflns_number_total             3829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05077_si_003.cif
_cod_data_source_block           u035
_cod_database_code               4519222
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H17 I N2 O8'
_chemical_oxdiff_usercomment     Narobe_Koenig_RN-590
_shelx_estimated_absorpt_t_max   0.408
_shelx_estimated_absorpt_t_min   0.195
_reflns_odcompleteness_completeness 99.14
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C10(H10), C2(H2), C14(H14), C18(H18), C22(H22), C6(H6), C3(H3),
 C19(H19), C12(H12), C13(H13), C5(H5), C11(H11)
;
_shelx_res_checksum              2707
_shelx_hkl_checksum              87281
_olex2_date_sample_data_collection 2021-04-06
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.928
_oxdiff_exptl_absorpt_empirical_full_min 0.366