Rh(i)-catalysed imine-directed C–H functionalization via the oxidative [3 + 2] cycloaddition of benzylamine derivatives with maleimides
Das, Amrita; Chatani, Naoto; Chemical Communications  (2022) –; doi:10.1039/D1CC06622F

data_7129497
_publ_section_title
;
 Rh(i)-catalysed imine-directed C--H functionalization via the oxidative
 [3 + 2] cycloaddition of benzylamine derivatives with maleimides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06622F
_journal_year                    2022
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-10 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.871(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6645(3)
_cell_length_b                   6.15540(10)
_cell_length_c                   20.4618(5)
_cell_measurement_reflns_used    8927
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.3460
_cell_measurement_theta_min      4.4250
_cell_volume                     1757.88(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -66.00  21.00   0.50    0.36    --  -42.80  23.00 127.00  174
  2  \w    -60.00 -34.00   0.50    1.44    -- -106.00 103.00 179.82   52
  3  \w    -73.00 -47.00   0.50    1.44    -- -106.00 125.00 120.00   52
  4  \w    -70.00 -34.00   0.50    1.44    -- -106.00  77.00 150.00   72
  5  \w   -108.00 -82.00   0.50    1.44    -- -106.00  77.00 150.00   52
  6  \w   -116.00 -90.00   0.50    1.44    -- -106.00 125.00 120.00   52
  7  \w   -125.00 -74.00   0.50    1.44    -- -106.00 137.00  34.57  102
  8  \w    -89.00 -55.00   0.50    1.44    -- -106.00 125.00 -60.00   68
  9  \w    -69.00 -44.00   0.50    1.44    -- -106.00 125.00 -90.00   50
 10  \w    -87.00 -61.00   0.50    1.44    -- -106.00  77.00 -60.00   52
 11  \w    -63.00 -37.00   0.50    1.44    -- -106.00  57.00 -60.00   52
 12  \w    -89.00 -63.00   0.50    1.44    -- -106.00  37.00 -30.00   52
 13  \w   -120.00 -83.00   0.50    1.44    -- -106.00 -19.00  30.00   74
 14  \w   -121.00 -95.00   0.50    1.44    -- -106.00  37.00 -30.00   52
 15  \w   -122.00 -96.00   0.50    1.44    -- -106.00  57.00  30.00   52
 16  \w   -132.00 -64.00   0.50    1.44    -- -106.00  23.00 127.00  136
 17  \w    -93.00 -68.00   0.50    0.36    --  -42.80 -23.00 -37.00   50
 18  \w   -127.00 -87.00   0.50    1.44    -- -106.00  47.00 -82.82   80
 19  \w   -100.00 -33.00   0.50    1.44    -- -106.00  57.00-120.00  134
 20  \w    -93.00 -52.00   0.50    0.36    --  -42.80 125.00-150.00   82
 21  \w    -45.00 -10.00   0.50    0.36    --  -42.80 125.00-150.00   70
 22  \w    -63.00  31.00   0.50    0.36    --  -42.80  57.00-180.00  188
 23  \w     -8.00  18.00   0.50    0.36    --   42.80 -23.00 -37.00   52
 24  \w     26.00  51.00   0.50    1.44    --   76.50 -23.00 -37.00   50
 25  \w     60.00  85.00   0.50    0.36    --   42.80  23.00 127.00   50
 26  \w     78.00 103.00   0.50    1.44    --   76.50  23.00 127.00   50
 27  \w    -95.00 -65.00   0.50    1.44    -- -106.00  77.00-120.00   60
 28  \w   -135.00 -98.00   0.50    1.44    -- -106.00  77.00-120.00   74
 29  \w   -131.00 -57.00   0.50    1.44    -- -106.00  77.00 -90.00  148
 30  \w   -138.00-112.00   0.50    1.44    -- -106.00 -19.00-150.00   52
 31  \w   -176.00-118.00   0.50    1.44    -- -106.00 -23.00 -37.00  116
 32  \w   -173.00-146.00   0.50    1.44    -- -106.00 -19.00-150.00   54
 33  \w   -175.00 -83.00   0.50    1.44    -- -106.00 -37.00-120.00  184
 34  \w   -112.00 -70.00   0.50    0.36    --  -42.80-125.00 -90.00   84
 35  \w   -134.00-106.00   0.50    1.44    -- -106.00 -37.00  90.00   56
 36  \w   -118.00 -92.00   0.50    1.44    -- -106.00 -99.00  90.00   52
 37  \w   -153.00 -89.00   0.50    1.44    -- -106.00 -57.00  90.00  128
 38  \w   -154.00-116.00   0.50    1.44    -- -106.00 -37.00 120.00   76
 39  \w   -176.00-129.00   0.50    1.44    -- -106.00 -19.00  30.00   94
 40  \w   -164.00-139.00   0.50    1.44    -- -106.00 -99.00  90.00   50
 41  \w   -173.00-123.00   0.50    1.44    -- -106.00 -37.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0358986000
_diffrn_orient_matrix_UB_12      -0.0516890000
_diffrn_orient_matrix_UB_13      -0.0615742000
_diffrn_orient_matrix_UB_21      -0.1032171000
_diffrn_orient_matrix_UB_22      -0.0536210000
_diffrn_orient_matrix_UB_23      -0.0439276000
_diffrn_orient_matrix_UB_31      -0.0154201000
_diffrn_orient_matrix_UB_32      0.2389816000
_diffrn_orient_matrix_UB_33      -0.0231847000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.146
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0496P)^2^+0.5107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3180
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06622f2.cif
_cod_data_source_block           exp_1619
_cod_database_code               7129497
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H17 N3 O2'
_chemical_oxdiff_usercomment     amrira-727_20210830_Cu
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C14(H14), C22(H22), C18(H18), C19(H19), C10(H10),
 C17(H17), C13(H13), C23(H23), C12(H12), C25(H25), C11(H11), C24(H24)
;
_shelx_res_checksum              80484
_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 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.647