Photoredox-Catalysed Formal [3+2] Cycloaddition of N-Aryl α-Amino with Isoquinoline N-Oxides
Liu, Xiangyuan; Yin, Yanli; Jiang, Zhiyong; Chemical Communications  (2019) –; doi:10.1039/C9CC06249A

data_7124106
_publ_section_title
;
 Photoredox-Catalysed Formal [3+2] Cycloaddition of N-Aryl \a-Amino with
 Isoquinoline N-Oxides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06249A
_journal_year                    2019
_chemical_formula_moiety         'C21 H23 Br N2 O3'
_chemical_formula_sum            'C21 H23 Br N2 O3'
_chemical_formula_weight         431.32
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-11 deposited with the CCDC.    2019-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.320(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1042(3)
_cell_length_b                   6.24720(17)
_cell_length_c                   22.4658(7)
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9820
_cell_measurement_theta_min      5.8460
_cell_volume                     2119.29(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   22.00   50.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 56

  2 omega   14.00   43.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 58

  3 omega   16.00  100.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   60.0000 168

  4 omega   44.00   93.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 98

  5 omega   67.00  111.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 88

  6 omega   39.00   87.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 96

  7 omega   96.00  164.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 136

  8 omega   70.00  104.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 68

  9 omega   34.00   61.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -120.0000 54

 10 omega   41.00  115.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 148

 11 omega   45.00   90.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 90

 12 omega   44.00   69.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 50

 13 omega   47.00  119.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 144

 14 omega   37.00   76.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 78

 15 omega   37.00   77.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 80

 16 omega  -33.00   -8.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 50

 17 omega  -94.00   -5.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 178

 18 omega  -11.00   36.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -120.0000 94

 19 omega  -60.00  -23.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -120.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0378557000
_diffrn_orient_matrix_UB_12      -0.0139542000
_diffrn_orient_matrix_UB_13      0.0629866000
_diffrn_orient_matrix_UB_21      0.0919011000
_diffrn_orient_matrix_UB_22      0.0543717000
_diffrn_orient_matrix_UB_23      0.0270434000
_diffrn_orient_matrix_UB_31      -0.0230279000
_diffrn_orient_matrix_UB_32      0.2401154000
_diffrn_orient_matrix_UB_33      -0.0024964000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7829
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.564
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0722P)^2^+0.5726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3012
_reflns_number_total             3786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06249a2.cif
_cod_data_source_block           lvy2694
_cod_original_cell_volume        2119.30(10)
_cod_database_code               7124106
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N3Cl2
_shelx_estimated_absorpt_t_max   0.765
_shelx_estimated_absorpt_t_min   0.616
_reflns_odcompleteness_completeness 99.86
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1-C2
 1.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1A)
4. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'