Visible light-induced N-radicals 5-exo/6-endo cyclization of alkenyl amide: facile access to isoindolinones/isoquinolinones
Lei, ZhenYao; Hu, Kui; He, Yuanxiang; Geng, Shu; Zou, Shuai; Chen, Lina; Li, Pan; Ding, ZhiJun; Huang, Feng; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00317A

data_7158544
_publ_section_title
;
 Visible light-induced N-radicals 5-exo/6-endo cyclization of alkenyl
 amide: facile access to isoindolinones/isoquinolinones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00317A
_journal_year                    2022
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-04-12
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2021-12-03 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.751(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3322(12)
_cell_length_b                   11.6410(19)
_cell_length_c                   12.031(3)
_cell_measurement_reflns_used    941
_cell_measurement_temperature    119(2)
_cell_measurement_theta_max      27.3840
_cell_measurement_theta_min      4.8910
_cell_volume                     1019.8(3)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8242
_diffrn_measurement_details
;
  1 omega  -29.00    4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070   37.0000 -180.0000 33

  2 omega   -9.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   77.0000  -90.0000 89

  3 omega   -6.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   77.0000   60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0140767000
_diffrn_orient_matrix_UB_12      0.0518745000
_diffrn_orient_matrix_UB_13      -0.0308094000
_diffrn_orient_matrix_UB_21      0.0638173000
_diffrn_orient_matrix_UB_22      0.0283448000
_diffrn_orient_matrix_UB_23      0.0396355000
_diffrn_orient_matrix_UB_31      0.0722195000
_diffrn_orient_matrix_UB_32      -0.0149192000
_diffrn_orient_matrix_UB_33      -0.0316373000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4091
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94144
_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            Colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.1357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                1495
_reflns_number_total             1958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00317a2.cif
_cod_data_source_block           exp_7641
_cod_database_code               7158544
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07