Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered N-Alkoxyamides with Air: Facile Access to Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones
Chen, Fei; Lai, Sheng-Qiang; Zhu, Fei-Fei; Meng, Qiang; Jiang, Yu; Yu, Wei; Han, Bing; ACS Catalysis 8 (2018) 8925–; doi:10.1021/acscatal.8b02445

data_4515709
_publ_section_title
;
 Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered
 N-Alkoxyamides with Air: Facile Access to
 Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8925
_journal_paper_doi               10.1021/acscatal.8b02445
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C17 H12 N2 O4'
_chemical_formula_sum            'C17 H12 N2 O4'
_chemical_formula_weight         308.29
_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     direct
_audit_creation_date             2018-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.472(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8554(3)
_cell_length_b                   18.0992(7)
_cell_length_c                   11.1588(4)
_cell_measurement_reflns_used    2602
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      69.8400
_cell_measurement_theta_min      3.9690
_cell_volume                     1383.26(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.966
_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      1.00  47.50   1.50    1.50    --   54.00 -99.00  90.00   31
  2  \w     37.00 140.50   1.50    1.50    --  108.00 -91.00  60.00   69
  3  \w     69.00 130.50   1.50    1.50    --  108.00 -63.00  30.00   41
  4  \w     88.00 178.00   1.50    1.50    --  108.00  38.00-120.00   60
  5  \w    136.00 176.50   1.50    1.50    --  108.00  50.00-180.00   27
  6  \w    103.00 143.50   1.50    1.50    --  108.00 111.00 -90.00   27
  7  \w     90.00 117.00   1.50    1.50    --  108.00  50.00-150.00   18
  8  \w     86.00 113.00   1.50    1.50    --  108.00  50.00-180.00   18
  9  \w     44.00  69.50   1.50    1.50    --    0.00  57.00-120.00   17
 10  \w    -16.00  11.00   1.50    1.50    --    0.00  57.00-120.00   18
 11  \w    -19.00 101.00   1.50    1.50    --   54.00   0.00  60.00   80
 12  \w     42.00  69.00   1.50    1.50    --    0.00  77.00  90.00   18
 13  \w     69.00 111.00   1.50    1.50    --   54.00-125.00-150.00   28
 14  \w     25.00  67.00   1.50    1.50    --   54.00-125.00-150.00   28
 15  \w    -28.00  -1.00   1.50    1.50    --    0.00  77.00  90.00   18
 16  \w    101.00 128.00   1.50    1.50    --  108.00 111.00  60.00   18
 17  \w    139.00 170.50   1.50    1.50    --  108.00 111.00  60.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2043486000
_diffrn_orient_matrix_UB_12      -0.0354638000
_diffrn_orient_matrix_UB_13      0.0111866000
_diffrn_orient_matrix_UB_21      0.0888439000
_diffrn_orient_matrix_UB_22      0.0756679000
_diffrn_orient_matrix_UB_23      0.0343609000
_diffrn_orient_matrix_UB_31      -0.0297763000
_diffrn_orient_matrix_UB_32      -0.0164601000
_diffrn_orient_matrix_UB_33      0.1333722000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4482
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.615
_diffrn_reflns_theta_min         4.887
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0957P)^2^+0.7272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2216
_reflns_number_total             2524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02445_si_002.cif
_cod_data_source_block           chfei_0307
_cod_original_cell_volume        1383.27(10)
_cod_database_code               4515709
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.25
_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:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_olex2_date_sample_data_collection 2018-03-07
_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 4.256
_oxdiff_exptl_absorpt_empirical_full_min 0.709